10-Q

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

Form 10-Q

(Mark One)

☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the quarterly period ended September 30, 2023

or

☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the transition period from____________to____________

Commission File Number: 001-39658

ROOT, INC.

(Exact name of Registrant as specified in its charter)

Delaware	84-2717903
(State or other jurisdiction of incorporation or organization)	(I.R.S. Employer Identification Number)
80 E. Rich Street, Suite 500 Columbus, Ohio	43215
(Address of principal executive offices)	(Zip Code)

(866) 980-9431

(Registrant’s telephone number, including area code)

N/A

(Former name, former address and former fiscal year if changed since last report)

Securities registered pursuant to Section 12(b) of the Act:

Title of each class	Trading Symbol(s)	Name of each exchange on which registered
Class A common stock, $0.0001 par value per share	ROOT	The Nasdaq Stock Market LLC

Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes ☒ No ☐

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). Yes ☒ No ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

Large accelerated filer ☐	Accelerated filer ☒
Non-accelerated filer ☐	Smaller reporting company ☒
	Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act). Yes ☐ No ☒

As of October 27, 2023, the number of outstanding shares of the registrant’s Class A common stock, par value $0.0001 per share, was 9.6 million and the number of outstanding shares of the registrant’s Class B common stock, par value $0.0001 per share, was 5.0 million.

TABLE OF CONTENTS

		Page
Special Note Regarding Forward-Looking Statements
	Part I. Financial Information	1
Item 1.	Condensed Consolidated Balance Sheets - Unaudited	1
	Condensed Consolidated Statements of Operations and Comprehensive Loss - Unaudited	2
	Condensed Consolidated Statements of Redeemable Convertible Preferred Stock and Stockholders’ Equity - Unaudited	3
	Condensed Consolidated Statements of Cash Flows - Unaudited	5
	Notes to Condensed Consolidated Financial Statements - Unaudited	6
Item 2.	Management's Discussion and Analysis of Financial Condition and Results of Operations	23
Item 3.	Quantitative and Qualitative Disclosures About Market Risk	42
Item 4.	Controls and Procedures	43
	Part II. Other Information	44
Item 1.	Legal Proceedings	44
Item 1A.	Risk Factors	45
Item 2.	Unregistered Sales of Equity Securities, Use of Proceeds, and Issuer Purchases of Equity Securities	46
Item 3.	Defaults Upon Senior Securities	47
Item 4.	Mine Safety Disclosures	48
Item 5.	Other Information	49
Item 6.	Exhibits	50
	Signatures	52

SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

This Quarterly Report on Form 10-Q contains forward-looking statements about us and our industry that involve substantial risks and uncertainties. All statements other than statements of historical facts contained in this Quarterly Report on Form 10-Q are forward-looking statements. In some cases, you can identify forward-looking statements because they contain words such as “anticipate,” “believe,” “contemplate,” “continue,” “could,” “estimate,” “expect,” “intend,” “may,” “path,” “plan,” “potential,” “predict,” “project,” “should,” “target,” “will” or “would” or the negative of these words or other similar terms or expressions. These forward-looking statements include, but are not limited to, statements concerning the following:

•our ability to retain existing customers, acquire new customers and expand our customer reach;

•our expectations regarding our future financial performance, including total revenue, gross profit/(loss), net income/(loss), direct contribution, adjusted EBITDA, net loss and loss adjustment expense, or LAE, ratio, net expense ratio, net combined ratio, gross loss ratio, marketing costs and costs of customer acquisition, gross LAE ratio, gross expense ratio, gross combined ratio, quota share levels, changes in unencumbered cash balances and expansion of our new and renewal premium base;

•our ability to realize profits, acquire customers, retain customers, contract with additional partners to utilize the product, or achieve other benefits from our embedded insurance offering;

•our ability to expand our distribution channels through additional partnership relationships, digital media and referrals;

•our ability to drive a significant long-term competitive advantage through our partnership with Carvana and other partnerships;

•our ability to develop embedded products for our new embedded insurance partners;

•the impact of supply chain disruptions, increasing inflation, a recession and/or disruptions to properly functioning financial and capital markets and interest rates on our business and financial condition;

•our ability to reduce operating losses and extend our capital runway;

•our goal to be licensed in all states in the United States and the timing of obtaining additional licenses and launching in new states;

•the accuracy and efficiency of our telematics and behavioral data, and our ability to gather and leverage additional data;

•our ability to materially improve retention rates and our ability to realize benefits from retaining customers;

•our ability to underwrite risks accurately and charge profitable rates;

•our ability to maintain our business model and improve our capital and marketing efficiency;

•our ability to drive improved conversion and decrease the cost of customer acquisition;

•our ability to maintain and enhance our brand and reputation;

•our ability to effectively manage the growth of our business;

•our ability to raise additional capital efficiently or at all;

•our ability to improve our product offerings, introduce new products and expand into additional insurance lines;

•our ability to cross sell our products and attain greater value from each customer;

•our lack of operating history and ability to attain profitability;

•our ability to compete effectively with existing competitors and new market entrants in our industry;

•future performance of the markets in which we operate;

•our ability to operate a “capital-efficient” business and obtain and maintain desirable levels of reinsurance;

•the effect of further reductions in the utilization of reinsurance, which would result in retention of more premium and losses and could cause our capital requirements to increase;

•our ability to realize economies of scale;

•our ability to attract, motivate and retain key personnel, or hire personnel, and to offer competitive compensation and benefits;

•our ability to deliver a vertically integrated customer experience;

•our ability to develop products that utilize our telematics to drive better customer satisfaction and retention;

•our ability to protect our intellectual property and any costs associated therewith;

•our ability to develop an autonomous claims experience;

•our ability to take rate action early and react to changing environments;

•our ability to meet risk-based capital requirements;

•our ability to realize the benefits anticipated from our Texas county mutual fronting arrangement;

•our ability to expand domestically;

•our ability to stay in compliance with laws and regulations that currently apply or become applicable to our business;

•the impact of litigation or other losses;

•the effect of increasing interest rates on our available cash and our ability to maintain compliance with our credit agreement;

•our ability to maintain proper and effective internal control over financial reporting and remediate existing deficiencies;

•our ability to continue to meet the Nasdaq Stock Market listing standards; and

•the growth rates of the markets in which we compete.

You should not rely on forward-looking statements as predictions of future events. The outcome of the events described in these forward-looking statements is subject to risks, uncertainties and other factors described under the heading “Risk Factors” and elsewhere in this Quarterly Report on Form 10-Q. Moreover, we operate in a very competitive and rapidly changing environment. New risks and uncertainties emerge from time to time, and it is not possible for us to predict all risks and uncertainties that could have an impact on the forward-looking statements contained herein. The results, events and circumstances reflected in the forward-looking statements may not be achieved or occur, and actual results, events or circumstances could differ materially from those described in the forward-looking statements.

The forward-looking statements made in this Quarterly Report on Form 10-Q relate only to events as of the date on which the statements are made and we undertake no obligation to update them to reflect events or circumstances after the date of this Quarterly Report on Form 10-Q or to reflect new information or the occurrence of unanticipated events, except as required by law.

Unless the context otherwise indicates, references in this report to the terms “Root,” “the Company,” “we,” “our” and “us” refer to Root, Inc. and its subsidiaries.

We may announce material business and financial information to our investors using our investor relations website (ir.joinroot.com). We therefore encourage investors and others interested in Root to review the information that we make available on our website, in addition to following our filings with the Securities and Exchange Commission, or SEC, webcasts, press releases and conference calls.

Part I.  Financial Information

Item 1.  Financial Statements

ROOT, INC. AND SUBSIDIARIES
CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED
	As of
	September 30,		December 31,
	2023		2022
	(in millions, except par value)
Assets
Investments:
Fixed maturities available-for-sale, at fair value (amortized cost: $171.1 and $134.2 at September 30, 2023 and December 31, 2022, respectively)	$	164.5	$	128.4
Short-term investments (amortized cost: $2.6 and $0.4 at September 30, 2023 and December 31, 2022, respectively)	2.6		0.4
Other investments	4.4		4.4
Total investments	171.5		133.2
Cash and cash equivalents	635.3		762.1
Restricted cash	1.0		1.0
Premiums receivable, net of allowance of $2.7 and $2.8 at September 30, 2023 and December 31, 2022, respectively	187.9		111.9
Reinsurance recoverable and receivable, net of allowance of $2.9 and $0.2 at September 30, 2023 and December 31, 2022, respectively	137.7		148.8
Prepaid reinsurance premiums	36.1		74.2
Other assets	70.7		81.7
Total assets	$	1,240.2	$	1,312.9
Liabilities, Redeemable Convertible Preferred Stock and Stockholders’ Equity
Liabilities:
Loss and loss adjustment expense reserves	$	256.5	$	287.4
Unearned premiums	218.9		136.5
Long-term debt and warrants	298.3		295.4
Reinsurance premiums payable	71.8		119.8
Accounts payable and accrued expenses	47.8		39.7
Other liabilities	57.8		45.0
Total liabilities	951.1		923.8
Commitments and Contingencies (Note 11)
Redeemable convertible preferred stock, $0.0001 par value, 100.0 shares authorized, 14.1 shares issued and outstanding at September 30, 2023 and December 31, 2022 (liquidation preference of $126.5)	112.0		112.0
Stockholders’ equity:
Class A common stock, $0.0001 par value, 1,000.0 shares authorized, 9.5 and 9.2 shares issued and outstanding at September 30, 2023 and December 31, 2022, respectively	—		—
Class B common stock, $0.0001 par value, 269.0 shares authorized, 5.0 shares issued and outstanding at September 30, 2023 and December 31, 2022	—		—
Additional paid-in capital	1,874.9		1,850.7
Accumulated other comprehensive loss	(6.6)		(5.8)
Accumulated loss	(1,691.2)		(1,567.8)
Total stockholders’ equity	177.1		277.1
Total liabilities, redeemable convertible preferred stock and stockholders’ equity	$	1,240.2	$	1,312.9

See Notes to Condensed Consolidated Financial Statements - Unaudited

1

ROOT, INC. AND SUBSIDIARIES
CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS - UNAUDITED
	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(in millions, except per share data)
Revenues:
Net premiums earned	$	100.0	$	68.6	$	223.9	$	221.6
Net investment income	9.0		0.9		22.5		2.2
Net realized gains on investments	—		—		—		1.1
Fee income	6.2		3.8		13.2		13.1
Other income	0.1		0.4		0.6		1.5
Total revenues	115.3		73.7		260.2		239.5
Operating expenses:
Loss and loss adjustment expenses	85.8		80.9		208.6		273.3
Sales and marketing	13.1		8.1		22.8		44.8
Other insurance expense (benefit)	18.3		1.1		22.2		(5.7)
Technology and development	11.1		14.3		32.4		46.1
General and administrative	21.0		26.4		63.2		96.4
Total operating expenses	149.3		130.8		349.2		454.9
Operating loss	(34.0)		(57.1)		(89.0)		(215.4)
Interest expense	(11.8)		(9.3)		(34.4)		(24.0)
Loss before income tax expense	(45.8)		(66.4)		(123.4)		(239.4)
Income tax expense	—		—		—		—
Net loss	(45.8)		(66.4)		(123.4)		(239.4)
Other comprehensive loss:
Changes in net unrealized losses on investments	(0.7)		(2.3)		(0.8)		(7.3)
Comprehensive loss	$	(46.5)	$	(68.7)	$	(124.2)	$	(246.7)
Loss per common share: basic and diluted (both Class A and B)	$	(3.16)	$	(4.71)	$	(8.57)	$	(17.10)
Weighted-average common shares outstanding: basic and diluted (both Class A and B)	14.5		14.1		14.4		14.0

See Notes to Condensed Consolidated Financial Statements - Unaudited

2

ROOT, INC. AND SUBSIDIARIES
CONDENSED CONSOLIDATED STATEMENTS OF REDEEMABLE CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS’ EQUITY - UNAUDITED
	Redeemable Convertible Preferred Stock			Class A and Class B Common Stock				Additional Paid-in Capital		Accumulated Other Comprehensive Loss		Accumulated Loss		Total Stockholders' Equity
	Shares	Amount		Class A Shares	Class B Shares	Amount
				(in millions)
Balance—June 30, 2023	14.1	$	112.0	9.4	5.0	$	—	$	1,865.7	$	(5.9)	$	(1,645.4)	$	214.4
Net loss	—	—		—	—	—		—		—		(45.8)		(45.8)
Other comprehensive loss	—	—		—	—	—		—		(0.7)		—		(0.7)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	—	—		0.1	—	—		—		—		—		—
Common stock—share-based compensation expense	—	—		—	—	—		4.7		—		—		4.7
Warrant compensation expense	—	—		—	—	—		5.0		—		—		5.0
Warrant issuance costs	—	—		—	—	—		(0.5)		—		—		(0.5)
Balance—September 30, 2023	14.1	$	112.0	9.5	5.0	$	—	$	1,874.9	$	(6.6)	$	(1,691.2)	$	177.1
Balance—January 1, 2023	14.1	$	112.0	9.2	5.0	$	—	$	1,850.7	$	(5.8)	$	(1,567.8)	$	277.1
Net loss	—	—		—	—	—		—		—		(123.4)		(123.4)
Other comprehensive loss	—	—		—	—	—		—		(0.8)		—		(0.8)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	—	—		0.3	—	—		—		—		—		—
Common stock—share-based compensation expense	—	—		—	—	—		12.4		—		—		12.4
Warrant compensation expense	—	—		—	—	—		13.3		—		—		13.3
Warrant issuance costs	—	—		—	—	—		(1.5)		—		—		(1.5)
Balance—September 30, 2023	14.1	$	112.0	9.5	5.0	$	—	$	1,874.9	$	(6.6)	$	(1,691.2)	$	177.1

3

ROOT, INC. AND SUBSIDIARIES
CONDENSED CONSOLIDATED STATEMENTS OF REDEEMABLE CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS’ EQUITY - UNAUDITED
	Redeemable Convertible Preferred Stock			Class A and Class B Common Stock				Additional Paid-in Capital		Accumulated Other Comprehensive (Loss) Income		Accumulated Loss		Total Stockholders' Equity
	Shares	Amount		Class A Shares	Class B Shares	Amount
				(in millions)
Balance—June 30, 2022	14.1	$	112.0	8.9	5.2	$	—	$	1,829.0	$	(4.6)	$	(1,443.1)	$	381.3
Net loss	—	—		—	—	—		—		—		(66.4)		(66.4)
Other comprehensive loss	—	—		—	—	—		—		(2.3)		—		(2.3)
Conversion of Class B to Class A	—	—		0.2	(0.2)	—		—		—		—		—
Common stock—share-based compensation expense	—	—		—	—	—		7.8		—		—		7.8
Warrant compensation expense	—	—		—	—	—		1.5		—		—		1.5
Warrant issuance costs	—	—		—	—	—		(0.1)		—		—		(0.1)
Balance—September 30, 2022	14.1	$	112.0	9.1	5.0	$	—	$	1,838.2	$	(6.9)	$	(1,509.5)	$	321.8
Balance—January 1, 2022	14.1	$	112.0	7.9	6.1	$	—	$	1,806.1	$	0.4	$	(1,270.1)	$	536.4
Net loss	—	—		—	—	—		—		—		(239.4)		(239.4)
Other comprehensive loss	—	—		—	—	—		—		(7.3)		—		(7.3)
Conversion of Class B to Class A	—	—		1.1	(1.1)	—		—		—		—		—
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	—	—		0.1	—	—		0.4		—		—		0.4
Reclassification of early-exercised stock options from liabilities	—	—		—	—	—		0.1		—		—		0.1
Common stock—share-based compensation expense	—	—		—	—	—		21.8		—		—		21.8
Warrant compensation expense	—	—		—	—	—		10.3		—		—		10.3
Warrant issuance costs	—	—		—	—	—		(1.1)		—		—		(1.1)
Term Loan warrants issued	—	—		—	—	—		0.6		—		—		0.6
Balance—September 30, 2022	14.1	$	112.0	9.1	5.0	$	—	$	1,838.2	$	(6.9)	$	(1,509.5)	$	321.8

See Notes to Condensed Consolidated Financial Statements - Unaudited

4

ROOT, INC. AND SUBSIDIARIES
CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - UNAUDITED
	Nine Months Ended September 30,
	2023		2022
	(in millions)
Cash flows from operating activities:
Net loss	$	(123.4)	$	(239.4)
Adjustments to reconcile net loss to net cash used in operating activities:
Share-based compensation	12.4		21.8
Warrant compensation expense	13.3		10.3
Depreciation and amortization	8.2		9.5
Bad debt expense	10.6		13.7
Net realized gains on investments	—		(1.1)
Gain on lease modification	(0.3)		(0.2)
Changes in operating assets and liabilities:
Premiums receivable	(83.9)		4.5
Reinsurance recoverable and receivable	8.5		19.0
Prepaid reinsurance premiums	38.1		14.6
Other assets	10.6		(2.0)
Losses and loss adjustment expenses reserves	(30.9)		(26.0)
Unearned premiums	82.4		(22.8)
Reinsurance premiums payable	(48.0)		8.8
Accounts payable and accrued expenses	9.6		17.5
Other liabilities	13.1		7.9
Net cash used in operating activities	(79.7)		(163.9)
Cash flows from investing activities:
Purchases of investments	(61.7)		(30.8)
Proceeds from maturities, call and pay downs of investments	22.3		26.7
Sales of investments	0.5		7.1
Capitalization of internally developed software	(7.1)		(7.4)
Purchases of fixed assets	(0.2)		—
Purchases of indefinite-lived intangible assets and transaction costs	—		(1.3)
Net cash used in investing activities	(46.2)		(5.7)
Cash flows from financing activities:
Proceeds from exercise of stock options and restricted stock units, net of tax (withholding)/proceeds	(0.9)		0.3
Proceeds from issuance of debt and related warrants, net of issuance costs	—		286.0
Payment of preferred stock and related warrants issuance costs	—		(3.0)
Net cash (used in) provided by financing activities	(0.9)		283.3
Net (decrease) increase in cash, cash equivalents and restricted cash	(126.8)		113.7
Cash, cash equivalents and restricted cash at beginning of period	763.1		707.0
Cash, cash equivalents and restricted cash at end of period	$	636.3	$	820.7

See Notes to Condensed Consolidated Financial Statements - Unaudited

5

ROOT, INC. AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS - UNAUDITED

1.NATURE OF BUSINESS

Root, Inc. is a holding company which, directly or indirectly, maintains 100% ownership of each of its subsidiaries, including, among others, Root Insurance Company and Root Property & Casualty Insurance Company, both Ohio-domiciled insurance companies, and Root Reinsurance Company, Ltd., a Cayman Islands-domiciled reinsurance company, together with Root, Inc., “we,” “us” or “our.”

We were formed in 2015 and began writing personal auto insurance in July 2016. We are a technology company operating primarily a direct-to-consumer model with the majority of our personal insurance customers acquired through mobile applications and our embedded platform. We offer auto and renters insurance products underwritten by Root Insurance Company and Root Property & Casualty Insurance Company.

2.BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

Basis of Presentation—In our opinion, all adjustments necessary for a fair presentation of the condensed consolidated financial statements have been included. All such adjustments are of a normal and recurring nature. These condensed consolidated financial statements are unaudited and, accordingly, should be read in conjunction with the consolidated financial statements and related notes included in the Annual Report on Form 10-K for the year ended December 31, 2022 filed with the Securities and Exchange Commission, or SEC, on February 22, 2023.

Basis of Consolidation—The unaudited condensed consolidated financial statements include the accounts of Root, Inc. and its subsidiaries, all of which are wholly owned. These financial statements have been prepared in accordance with accounting principles generally accepted in the United States, or GAAP. All intercompany accounts and transactions have been eliminated.

Use of Estimates—The preparation of the unaudited condensed consolidated financial statements requires management to make certain estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the unaudited condensed consolidated financial statements and the reported amounts of revenue and expenses during the reporting period. Actual results could differ from those estimates. Significant estimates reflected in our unaudited condensed consolidated financial statements include, but are not limited to, reserves for loss and loss adjustment expense, or LAE, valuation allowances for income taxes and allowance for expected credit losses on premium receivables and reinsurance recoverables.

Revision of Previously Issued Financial Statements—During the fourth quarter of 2022, we identified errors in our first, second and third quarter financial statements for 2022 and revised the quarterly presentation of certain sales and marketing and general and administrative expenses on our condensed consolidated statements of operations and comprehensive loss related to the purported misappropriation of funds by a senior marketing employee. The errors did not impact periods prior to 2022.

In accordance with SEC Staff Accounting Bulletin, or SAB, No. 99, Materiality, and SAB No. 108, Considering the Effects of Prior Year Misstatements when Quantifying Misstatements in Current Year Financial Statements, we assessed the materiality of these errors on our financial statements and concluded the errors were not material to the unaudited interim financial statements for the three and nine months ended September 30, 2022.

6

The following tables present the effect of the revision on the condensed consolidated statements of operations and comprehensive loss for the three and nine months ended September 30, 2022, condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity and condensed consolidated statement of cash flows as of and for the nine months ended September 30, 2022.

	Three Months Ended September 30, 2022 (unaudited)						Nine Months Ended September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected		As reported		Adjustments		As Corrected
	(in millions, except per share amounts)
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing	$	5.7	$	2.4	$	8.1	$	45.8	$	(1.0)	$	44.8
General and administrative	26.4		—		26.4		86.3		10.1		96.4
Total operating expenses	128.4		2.4		130.8		445.8		9.1		454.9
Operating loss	(54.7)		(2.4)		(57.1)		(206.3)		(9.1)		(215.4)
Loss before income tax expense	(64.0)		(2.4)		(66.4)		(230.3)		(9.1)		(239.4)
Net loss	(64.0)		(2.4)		(66.4)		(230.3)		(9.1)		(239.4)
Comprehensive loss	$	(66.3)	$	(2.4)	$	(68.7)	$	(237.6)	$	(9.1)	$	(246.7)
Weighted-average common shares outstanding: basic and diluted (both Class A and B)	14.1				14.1		14.0				14.0
Loss per common share: basic and diluted (both Class A and B)	$	(4.54)			$	(4.71)	$	(16.45)			$	(17.10)

	As of September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected
	(in millions)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Accumulated loss	$	(1,500.4)	$	(9.1)	$	(1,509.5)
Total stockholders’ equity	$	330.9	$	(9.1)	$	321.8

	Nine Months Ended September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected
	(in millions)
Condensed consolidated statement of cash flows:
Net loss	$	(230.3)	$	(9.1)	$	(239.4)
Other assets	(11.1)		9.1		(2.0)
Net cash used in operating activities	$	(163.9)	$	—	$	(163.9)

7

Cash, Cash Equivalents and Restricted Cash—The following table provides a reconciliation of cash, cash equivalents and restricted cash reported within the condensed consolidated balance sheets that sum to the total of the same such amount in the condensed consolidated statements of cash flows:

	As of
	September 30,		December 31,
	2023		2022
	(dollars in millions)
Cash and cash equivalents	$	635.3	$	762.1
Restricted cash	1.0		1.0
Total cash, cash equivalents and restricted cash shown in the condensed consolidated statements of cash flows	$	636.3	$	763.1

Performance-Based Restricted Stock Units—During the third quarter of 2023, we granted 0.4 million performance-based restricted stock units, or PSUs, to certain key employees as part of our equity compensation plan. The PSUs are expected to vest over a derived service period of one to four-years and are dependent upon the fulfillment of both a service condition and the achievement of stock-price goals during the performance period, with the latter being classified as a market condition according to Accounting Standard Codification 718, Stock Compensation. The service condition with respect to the four tranches of PSUs will be met in installments on April 1, 2024, and each of the subsequent three anniversaries of that date, or Vesting Date Requirement, subject to the individual’s continued service through such dates. Stock price goals must be met on or after the respective tranche’s Vesting Date Requirement and are based on the average closing price per share of our Class A common stock over a consecutive 45 day trading period. Any tranche of PSUs with respect to which the stock price goal has not been met as of April 1, 2028 (the final day of the performance period) will be forfeited as of such date.

The PSU compensation expense is recognized based on the grant date fair value of the award, which was determined by simulating Root’s stock prices using a Monte Carlo simulation in a risk-neutral framework, assuming a Geometric Brownian Motion. The simulation is repeated 100,000 times, and the average of the discounted values for each tranche is the grant date fair value for that tranche. The median time to vest is the derived service period.

Employing a Monte Carlo simulation requires a range of inputs for each uncertain variable, and establishing linkage between the assumptions, if necessary. Inputs and assumptions used in our analysis included our stock price at grant date, exercise prices, the term of the PSUs, equity volatility, risk-free rate and dividend yield. Equity volatility was derived using a blended volatility assumption of 50% weight on Root’s historical volatility calculated from daily stock returns since IPO from the grant date and a 50% weight based on Root’s term matched simple average peer volatility as of the valuation date because our company-specific volatility is not sufficient by itself at the time of grant.

The expense is recognized via a graded vesting method over the derived service period. In the event that both the service condition and market condition are met earlier, expense would be accelerated. If the service condition is not achieved, previously recognized compensation cost for the associated tranche is reversed. In the event that the market conditions are never achieved before the expiration date, but the service condition is met, the respective compensation costs remain recognized.

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3.INVESTMENTS

The amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities at September 30, 2023 and December 31, 2022 are as follows:

	September 30, 2023
	Amortized Cost		Allowance for Expected Credit Losses		Gross Unrealized Gains		Gross Unrealized Losses		Fair Value
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	16.8	$	—	$	—	$	(0.4)	$	16.4
Municipal securities	25.6		—		—		(1.3)		24.3
Corporate debt securities	69.4		—		—		(2.9)		66.5
Residential mortgage-backed securities	12.3		—		—		(0.5)		11.8
Commercial mortgage-backed securities	31.0		—		—		(1.3)		29.7
Other debt obligations	16.0		—		—		(0.2)		15.8
Total fixed maturities	171.1		—		—		(6.6)		164.5
Short-term investments	2.6		—		—		—		2.6
Total	$	173.7	$	—	$	—	$	(6.6)	$	167.1
	December 31, 2022
	Amortized Cost		Allowance for Expected Credit Losses		Gross Unrealized Gains		Gross Unrealized Losses		Fair Value
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	11.3	$	—	$	—	$	(0.3)	$	11.0
Municipal securities	21.4		—		—		(1.2)		20.2
Corporate debt securities	60.5		—		—		(2.7)		57.8
Residential mortgage-backed securities	5.5		—		—		(0.3)		5.2
Commercial mortgage-backed securities	24.4		—		—		(1.2)		23.2
Other debt obligations	11.1		—		0.1		(0.2)		11.0
Total fixed maturities	134.2		—		0.1		(5.9)		128.4
Short-term investments	0.4		—		—		—		0.4
Total	$	134.6	$	—	$	0.1	$	(5.9)	$	128.8

Management reviewed the available-for-sale securities at each balance sheet date to consider whether it was necessary to recognize a credit loss as of September 30, 2023 and December 31, 2022. We do not intend to sell the investments and it is not more likely than not that we will be required to sell the security before recovery. Management concluded that the available-for-sale securities’ unrealized losses were due to non-credit related factors and, therefore, there was no allowance for credit loss as of September 30, 2023 and December 31, 2022.

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The following tables reflect the gross unrealized losses and fair value of short-term investments and available-for-sale fixed maturity securities, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at September 30, 2023 and December 31, 2022:

	September 30, 2023
	Less than 12 Months				12 Months or More				Total
	Fair Value		Unrealized Loss		Fair Value		Unrealized Loss		Fair Value		Unrealized Loss
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	10.2	$	(0.2)	$	6.2	$	(0.2)	$	16.4	$	(0.4)
Municipal securities	7.9		(0.2)		15.7		(1.1)		23.6		(1.3)
Corporate debt securities	27.1		(0.8)		39.3		(2.1)		66.4		(2.9)
Residential mortgage-backed securities	8.5		(0.2)		2.7		(0.3)		11.2		(0.5)
Commercial mortgage-backed securities	13.5		(0.4)		15.8		(0.9)		29.3		(1.3)
Other debt obligations	9.5		(0.1)		3.8		(0.1)		13.3		(0.2)
Total fixed maturities	76.7		(1.9)		83.5		(4.7)		160.2		(6.6)
Short-term investments	1.1		—		—		—		1.1		—
Total	$	77.8	$	(1.9)	$	83.5	$	(4.7)	$	161.3	$	(6.6)
	December 31, 2022
	Less than 12 Months				12 Months or More				Total
	Fair Value		Unrealized Loss		Fair Value		Unrealized Loss		Fair Value		Unrealized Loss
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	6.9	$	(0.1)	$	4.1	$	(0.2)	$	11.0	$	(0.3)
Municipal securities	11.5		(0.5)		8.2		(0.7)		19.7		(1.2)
Corporate debt securities	45.3		(1.6)		11.5		(1.1)		56.8		(2.7)
Residential mortgage-backed securities	2.2		—		1.9		(0.3)		4.1		(0.3)
Commercial mortgage-backed securities	18.3		(0.8)		4.6		(0.4)		22.9		(1.2)
Other debt obligations	6.8		(0.2)		—		—		6.8		(0.2)
Total fixed maturities	91.0		(3.2)		30.3		(2.7)		121.3		(5.9)
Short-term investments	0.1		—		—		—		0.1		—
Total	$	91.1	$	(3.2)	$	30.3	$	(2.7)	$	121.4	$	(5.9)

Other Investments

As of September 30, 2023 and December 31, 2022, other investments related to our private equity investments were $4.4 million. There were no realized gains or losses for the three and nine months ended September 30, 2023. We recognized zero and $1.2 million of realized gains for the three and nine months ended September 30, 2022, respectively. We recorded the gain on sale of our private equity investments within net realized gains on investments in our condensed consolidated statements of operations and comprehensive loss. There were no unrealized gains and losses or impairment losses recognized on private equity investments for the three and nine months ended September 30, 2023 and 2022.

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The following table reflects the gross and net realized gains and losses on short-term investments, available-for-sale fixed maturities and other investments that have been included in the condensed consolidated statements of operations and comprehensive loss for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Realized gains on investments	$	—	$	—	$	—	$	1.2
Realized losses on investments	—		—		—		(0.1)
Net realized gains on investments	$	—	$	—	$	—	$	1.1

The following table sets forth the amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities by contractual maturity at September 30, 2023:

	September 30, 2023
	Amortized Cost		Fair Value
	(dollars in millions)
Due in one year or less	$	33.3	$	32.8
Due after one year through five years	102.3		98.1
Due five years through 10 years	21.4		20.4
Due after 10 years	16.7		15.8
Total	$	173.7	$	167.1

The following table sets forth the components of net investment income for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Interest on bonds	$	1.4	$	0.6	$	3.3	$	1.7
Interest on deposits and cash equivalents	7.9		0.6		19.8		1.2
Total	9.3		1.2		23.1		2.9
Investment expense	(0.3)		(0.3)		(0.6)		(0.7)
Net investment income	$	9.0	$	0.9	$	22.5	$	2.2

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The following tables summarize the credit ratings of short-term investments and available-for-sale fixed maturity securities at September 30, 2023 and December 31, 2022:

	September 30, 2023
	Amortized Cost		Fair Value		% of Total Fair Value
	(dollars in millions)
S&P Global rating or equivalent
AAA	$	51.2	$	49.3	29.5	%
AA+, AA, AA-, A-1	62.4		60.2		36.0
A+, A, A-	46.3		44.2		26.5
BBB+, BBB, BBB-	13.8		13.4		8.0
Total	$	173.7	$	167.1	100.0	%

	December 31, 2022
	Amortized Cost		Fair Value		% of Total Fair Value
	(dollars in millions)
S&P Global rating or equivalent
AAA	$	62.5	$	59.9	46.5	%
AA+, AA, AA-, A-1	19.9		19.1		14.8
A+, A, A-	38.4		36.5		28.3
BBB+, BBB, BBB-	13.8		13.3		10.4
Total	$	134.6	$	128.8	100.0	%

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4.FAIR VALUE OF FINANCIAL INSTRUMENTS

The following tables provide information about our financial assets measured and reported at fair value as of September 30, 2023 and December 31, 2022:

	September 30, 2023
	Level 1		Level 2		Level 3		Total Fair Value
	(dollars in millions)
Assets
Fixed maturities:
U.S. Treasury securities and agencies	$	15.4	$	1.0	$	—	$	16.4
Municipal securities	—		24.3		—		24.3
Corporate debt securities	—		66.5		—		66.5
Residential mortgage-backed securities	—		11.8		—		11.8
Commercial mortgage-backed securities	—		29.7		—		29.7
Other debt obligations	—		15.8		—		15.8
Total fixed maturities	15.4		149.1		—		164.5
Short-term investments	2.4		0.2		—		2.6
Cash equivalents	363.6		—		—		363.6
Total assets at fair value	$	381.4	$	149.3	$	—	$	530.7
	December 31, 2022
	Level 1		Level 2		Level 3		Total Fair Value
	(dollars in millions)
Assets
Fixed maturities:
U.S. Treasury securities and agencies	$	9.2	$	1.8	$	—	$	11.0
Municipal securities	—		20.2		—		20.2
Corporate debt securities	—		57.8		—		57.8
Residential mortgage-backed securities	—		5.2		—		5.2
Commercial mortgage-backed securities	—		23.2		—		23.2
Other debt obligations	—		11.0		—		11.0
Total fixed maturities	9.2		119.2		—		128.4
Short-term investments	—		0.4		—		0.4
Cash equivalents	487.3		—		—		487.3
Total assets at fair value	$	496.5	$	119.6	$	—	$	616.1

We estimate the fair value of all our different classes of Level 2 fixed maturities and short-term investments by using quoted prices from a combination of an independent pricing vendor or broker/dealer, pricing models, quoted prices of securities with similar characteristics or discounted cash flows. All significant inputs were observable in the active markets.

Private Equity Investments Measured at Fair Value on a Non-Recurring Basis

Private equity investments that have been remeasured during the period due to an observable event or impairment are classified within Level 3 in the fair value hierarchy because we estimate the value based on valuation methods which may include a combination of the observable transaction price at the transaction date and other

13

unobservable inputs including volatility, rights, and obligations of the investments we hold. See Note 3, “Investments,” for further information on our private equity investments.

Fair Value of Long-Term Debt

The carrying amount of long-term debt is recorded at the unpaid balance, net of discount and debt issuance costs. The fair value of outstanding long-term debt is classified within Level 2 of the fair value hierarchy. The fair value is based on a model referencing observable interest rates and spreads to project and discount cash flows to present value. As of September 30, 2023 and December 31, 2022, the carrying amounts and fair values of these financial instruments were as follows:

	Carrying Amount as of September 30, 2023		Estimated Fair Value as of September 30, 2023		Carrying Amount as of December 31, 2022		Estimated Fair Value as of December 31, 2022
	(dollars in millions)
Long-term debt	$	298.3	$	304.8	$	295.4	$	309.7

The carrying amounts of other short-term financial instruments approximates their fair value due to their short-term nature.

5.LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES

The following provides a reconciliation of the beginning and ending reserve balances for loss and LAE, net of reinsurance:

	Nine Months Ended September 30,
	2023		2022
	(dollars in millions)
Gross loss and LAE reserves, January 1	$	287.4	$	320.2
Reinsurance recoverable on unpaid losses	(76.4)		(79.5)
Net loss and LAE reserves, January 1	211.0		240.7
Net incurred loss and LAE related to:
Current year	209.2		273.5
Prior years	(0.6)		(0.2)
Total incurred	208.6		273.3
Net paid loss and LAE related to:
Current year	87.4		155.5
Prior years	117.3		135.6
Total paid	204.7		291.1
Net loss and LAE reserves, September 30	214.9		222.9
Plus reinsurance recoverable on unpaid losses	41.6		71.3
Gross loss and LAE reserves, September 30	$	256.5	$	294.2

Incurred losses and LAE attributable to prior accident years was a decrease of $0.6 million and $0.2 million for the nine months ended September 30, 2023 and 2022, respectively. For the nine months ended September 30, 2023, the development of incurred losses and LAE related to prior periods was a result of lower-than-expected reported losses on injury coverages, partially offset by losses on commutations of certain reinsurance agreements and higher-than-expected LAE on prior accident periods. For the nine months ended September 30, 2022, the development of incurred losses and LAE related to prior periods was a result of lower-than-expected LAE on prior accident period claims, partially offset by higher-than-expected reported losses on property damage and collision claims due to inflation.

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6.REINSURANCE

The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Premiums written:
Direct	$	192.7	$	139.6	$	444.6	$	443.9
Assumed	31.5		11.1		59.3		34.1
Ceded	(22.3)		(81.0)		(159.4)		(264.5)
Net premiums written	$	201.9	$	69.7	$	344.5	$	213.5
Premiums earned:
Direct	$	141.6	$	144.5	$	381.9	$	469.3
Assumed	18.2		10.8		39.5		31.5
Ceded	(59.8)		(86.7)		(197.5)		(279.2)
Net premiums earned	$	100.0	$	68.6	$	223.9	$	221.6
Losses and LAE incurred:
Direct	$	106.8	$	126.1	$	297.1	$	430.0
Assumed	13.4		11.3		29.8		35.7
Ceded	(34.4)		(56.5)		(118.3)		(192.4)
Net losses and LAE incurred	$	85.8	$	80.9	$	208.6	$	273.3

During the third quarter of 2023, we commuted certain agreements with our reinsurers which resulted in $4.4 million of net premiums earned, $4.2 million of loss and loss adjustment expenses and $5.8 million of other insurance expense (benefit), respectively, on the condensed consolidated statements of operations and comprehensive loss. A portion of the loss and loss adjustment expenses is related to an allowance for credit losses of $2.8 million, that was established due to a commutation with one of our reinsurers as of September 30, 2023.

Additionally, in connection with the commutation of certain agreements with reinsurers during the third quarter of 2023, we received cash and cash equivalents of $3.9 million, reinsurance recoverable and receivable decreased by $6.1 million, prepaid reinsurance premiums was reduced by $33.5 million and reinsurance premiums payable decreased by $30.2 million all of which are reported within the condensed consolidated balance sheets.

In the event that all or any of the reinsuring companies might be unable to meet their obligations under existing reinsurance agreements, we would be liable to the policyholder for such defaulted amounts.

7.LONG-TERM DEBT

In January 2022, we entered into a $300.0 million five-year term loan, or Term Loan, with the principal amount due and payable upon maturity on January 27, 2027. Interest is payable quarterly and is determined on a floating interest rate currently calculated on the Secured Overnight Financing Rate, or SOFR, with a 1.0% floor, plus 9.0%.

15

The following summarizes the carrying value of long-term debt as of September 30, 2023 and December 31, 2022:

	September 30, 2023		December 31, 2022
	(dollars in millions)
Term Loan	$	300.0	$	300.0
Accrued interest payable	7.9		7.3
Unamortized discount, debt issuance costs and warrants	(9.6)		(11.9)
Total	$	298.3	$	295.4

8.INCOME TAXES

The consolidated effective tax rate was zero for the three and nine months ended September 30, 2023 and 2022. The difference between these rates and the U.S. federal income tax rate of 21% was primarily due to a full valuation allowance on our U.S. deferred tax assets.

As of September 30, 2023 and December 31, 2022, we did not have any unrecognized tax benefits for uncertain tax positions and had no interest or penalties related to uncertain tax positions.

9.RESTRUCTURING COSTS

In 2022, we conducted strategic initiatives to reduce operating costs, improve efficiency, and increase focus on our strategic priorities. These initiatives resulted in restructuring actions that included a reduction in workforce levels, contract terminations, and in certain instances, a reduction in office space. These restructuring actions include the following costs:

Employee costs—consist of severance, benefits, share-based compensation, and employee compensation expense dependent upon continuous employment for certain employees and related employee costs.

Real estate exit costs—consist of real estate exit costs primarily related to accelerated amortization of right-of-use assets, leasehold improvements and furniture and fixtures.

Other costs—primarily consist of contract termination costs incurred as part of our efforts to improve efficiency and reduce operating costs and accelerated expense for software that no longer has economic benefit.

As of September 30, 2023, we expect to incur approximately $1.7 million of employee compensation expense, dependent upon continuous employment for certain employees, to be recognized ratably through the fourth quarter of 2023. We expect a cash expenditure related to these employee compensation costs in January 2024. As of September 30, 2023, except as discussed above, we do not expect to incur any additional material expenditures in future periods related to restructuring actions that have occurred.

The following table displays restructuring costs recorded in general and administrative expenses on the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,				Cumulative Incurred Through September 30, 2023
	2023		2022		2023		2022
	(dollars in millions)
Restructuring costs:
Employee costs	$	1.8	$	—	$	5.9	$	5.6	$	21.4
Real estate exit costs	—		—		—		2.1		2.1
Other costs	0.1		—		3.5		0.7		4.5
Total restructuring costs	$	1.9	$	—	$	9.4	$	8.4	$	28.0

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The following table displays a rollforward of the accrual for restructuring costs recorded in other liabilities on the condensed consolidated balance sheets:

	Employee costs		Other costs		Total liability
	(dollars in millions)
Restructuring activity:
Restructuring liability as of January 1, 2023	$	3.1	$	0.1	$	3.2
Expense incurred	5.5		3.4		8.9
Payments	(2.0)		(3.5)		(5.5)
Restructuring liability as of September 30, 2023	$	6.6	$	—	$	6.6

10.SHARE-BASED COMPENSATION

Warrants

In October 2021, we issued Carvana eight tranches of warrants, comprised of three tranches of “short-term warrants” and five tranches of “long-term warrants,” with the opportunity to purchase a maximum of 7.2 million shares of Class A common stock. As of September 30, 2023, we determined the remaining unvested short-term warrants were probable of vesting. Under that scenario, it is not a possible outcome for the long-term warrants to also vest, so they are considered not probable of vesting. We recognized warrant compensation expense related to these equity-classified warrants based on progress toward completing the integrated automobile insurance solution for Carvana’s online buying platform, or the Integrated Platform, and policies originating through the Integrated Platform. All of these warrants are out-of-the-money and therefore have no intrinsic value as of September 30, 2023.

The following table displays warrant compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Warrant compensation expense:
Sales and marketing	$	—	$	—	$	—	$	8.8
Other insurance expense (benefit)	5.0		1.5		13.3		1.5
Total warrant compensation expense	$	5.0	$	1.5	$	13.3	$	10.3

As of September 30, 2023, there was $7.8 million of unrecognized compensation cost related to warrants. The remaining costs are expected to be recognized over a period of approximately one year.

Employee Share-Based Compensation

We maintain an equity incentive plan, or the Plan, for the issuance and grant of equity awards (restricted stock, restricted stock units, or RSUs, PSUs, and incentive and nonqualified stock options) to our officers, directors, employees and certain advisors. As of September 30, 2023, we had 1.2 million common shares available for issuance under the Plan.

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The following table displays share-based compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Share-based compensation expense:
Loss and loss adjustment expenses	$	0.2	$	0.2	$	0.5	$	0.6
Sales and marketing	0.1		0.3		0.3		0.7
Other insurance expense (benefit)	0.1		0.3		0.4		0.8
Technology and development	0.9		1.1		2.4		3.1
General and administrative	3.4		5.9		8.8		16.6
Total share-based compensation expense	$	4.7	$	7.8	$	12.4	$	21.8

The following table provides total share-based compensation expense by type of award:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Share-based compensation expense:
Restricted stock unit expense	$	4.4	$	7.4	$	11.4	$	20.5
Performance-based restricted stock unit expense	0.1		—		0.1		—
Stock option expense	0.2		0.4		0.9		1.3
Total share-based compensation expense	$	4.7	$	7.8	$	12.4	$	21.8

As of September 30, 2023, there was $1.2 million, $25.3 million, and $2.2 million of unrecognized compensation cost related to unvested stock options, RSUs, and PSUs, respectively. The remaining costs are expected to be recognized over a period of approximately three years for unvested stock options and four years for RSUs and PSUs.

Performance-Based Restricted Stock Units

The fair value of the PSUs is estimated on the date of grant using a Monte Carlo simulation with Geometric Brownian Motion that uses certain inputs, assumptions and estimates, as follows: expected term of approximately five years, based on the contractual term of the PSUs; risk-free interest rate of 4.06%, based on U.S. Constant Maturity Yield Curve over a similar term; dividend rate of 0.0%, based on our historical and expected future dividend payouts; and volatility of 76%, and other factors.

The following table provides other key terms of the PSUs:

Performance-Based Restricted Stock Units	Stock Price Goals		Shares Issued	Grant Date Fair Value per Share
	(in millions, except per share amounts)
Tranches:
Tranche 1	$	16.76	—	$	7.69
Tranche 2	25.14		0.1	6.70
Tranche 3	33.52		0.1	5.87
Tranche 4	$	41.90	0.2	$	5.10
			0.4

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Restricted Stock Units and Performance-Based Restricted Stock Units

A summary of RSU and PSU activity for the nine months ended September 30, 2023 is as follows:

	Nine Months Ended September 30, 2023
Restricted Stock Units and Performance-Based Restricted Stock Units	Number of Shares	Weighted-Average Grant Date Fair Value per Share		Aggregate Intrinsic Value
	(in millions, except per share amounts)
Nonvested at January 1, 2023	1.1	$	51.81	$	5.0
Granted	1.6	6.62
Vested	(0.5)	50.44		2.8
Forfeited, expired or canceled	(0.2)	53.75
Nonvested at September 30, 2023	2.0	$	15.79	$	18.9

Stock Options

A summary of option activity for the nine months ended September 30, 2023 is as follows:

	Nine Months Ended September 30, 2023
Options	Number of Shares	Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Term (in Years)	Aggregate Intrinsic Value
	(in millions, except exercise price and term amounts)
Outstanding and exercisable at January 1, 2023	0.2	$	38.15	5.63	$	0.2
Granted	—	8.94
Exercised	—	—			—
Forfeited, expired or canceled	(0.1)	44.86
Outstanding and exercisable at September 30, 2023	0.1	$	33.74	4.53	$	0.5

11.COMMITMENTS AND CONTINGENCIES

From time to time, we are party to litigation and legal proceedings relating to our business operations. Except as disclosed below, we do not believe that we are party to any current or pending legal action that could reasonably be expected to have a material adverse effect on our financial condition or results of operations and cash flow.

On December 19, 2022, a purported class action complaint was filed against the Company’s subsidiary, Root Insurance Company, in the U.S. District Court for the Western District of Texas (Case No. 1:22-cv-01328-LY) by an individual on her behalf and further claiming to represent a putative class of insureds. The complaint alleges that Root Insurance Company breached its insurance contract and violated specific provisions of the Texas Prompt Payment of Claims Act for an alleged failure to include sales tax in total loss vehicle settlements. The complaint seeks damages to include payment of alleged benefits owed under the policy, in addition to pre- and post-judgment interest and attorneys fees on behalf of the named plaintiff and the putative class members. Root Insurance Company’s motion to dismiss the claims set forth in the complaint was granted and the lawsuit was dismissed with prejudice on August 22, 2023, which dismissal has been appealed. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is in its early stages. Therefore, at this time, we cannot predict the outcome or estimate the likelihood or magnitude of our possible or potential loss contingency.

On June 27, 2022, a verified shareholder derivative complaint was filed against certain of the Company’s current and former officers and directors in the U.S. District Court for the District of Delaware (Case No. 1:22-

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cv-00865). The Company was named as a nominal defendant. The complaint alleges that defendants made false or misleading statements and omissions of purportedly material fact, in violation of Section 10(b) of the Securities Exchange Act of 1934, or the Exchange Act, and Rule 10b-5 thereunder, breached their fiduciary duties and/or aided and abetted the breach of fiduciary duties, were unjustly enriched, wasted corporate assets, and are liable under Section 11(f) of the Securities Act of 1933, or the Securities Act, in connection with and following the Company’s initial public offering. The complaint seeks unspecified damages. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is currently stayed pending final resolution of the below matter and, at this time, we cannot predict the outcome or estimate the likelihood or magnitude of our possible or potential loss contingency.

On March 19, 2021, a purported class action complaint was filed against the Company and certain of its current and former officers and directors in the U.S. District Court for the Southern District of Ohio (Case No. 2:21-cv-01197) on behalf of certain Root shareholders. The complaint alleges that defendants made false or misleading statements and omissions of purportedly material fact, in violation of Sections 10(b) and 20(a) of the Exchange Act and Rule 10b-5 thereunder, and of Sections 11 and 15 of the Securities Act in connection with and following the Company’s initial public offering. The complaint seeks unspecified damages. The defendants’ motion to dismiss the claims set forth in the complaint was granted and the lawsuit was dismissed with prejudice on March 31, 2023, which dismissal has been appealed. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is in the early stages and, at this time, we cannot predict the outcome or estimate the likelihood or magnitude of our possible or potential loss contingency.

We are contingently liable for possible future assessments under regulatory requirements for insolvencies and impairments of unaffiliated insurance companies.

12.OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME

The following table presents the changes in our accumulated other comprehensive (loss) income, or AOCI, for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Beginning balance	$	(5.9)	$	(4.6)	$	(5.8)	$	0.4
Other comprehensive loss before reclassifications	(0.7)		(2.3)		(0.8)		(7.4)
Net realized losses on investments reclassified from AOCI to net loss	—		—		—		0.1
Other comprehensive loss	(0.7)		(2.3)		(0.8)		(7.3)
Ending balance	$	(6.6)	$	(6.9)	$	(6.6)	$	(6.9)

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13.LOSS PER SHARE

The following table displays the computation of basic and diluted loss per share for both Class A and Class B common stock for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(in millions, except per share amounts)
Net loss	$	(45.8)	$	(66.4)	$	(123.4)	$	(239.4)
Weighted-average common shares outstanding: basic and diluted (both Class A and B)	14.5		14.1		14.4		14.0
Loss per common share: basic and diluted (both Class A and B)	$	(3.16)	$	(4.71)	$	(8.57)	$	(17.10)

We excluded the following potentially dilutive common stock equivalents, presented based on amounts outstanding at each period end, from the computation of diluted loss per share attributable to common shareholders for the periods indicated because including them would have had an anti-dilutive effect:

	As of September 30,
	2023	2022
	(in millions)
Options to purchase common stock	0.1	0.2
Nonvested shares subject to repurchase	0.1	0.1
Restricted stock units and performance-based restricted stock units	2.0	1.3
Redeemable convertible preferred stock (as converted to common stock)	0.8	0.8
Warrants to purchase common stock	7.7	7.7
Total	10.7	10.1

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14.GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN

Gross premiums written by state is as follows for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,								Nine Months Ended September 30,
	2023				2022				2023				2022
	Amount		% of Total		Amount		% of Total		Amount		% of Total		Amount		% of Total
	(dollars in millions)
State:
Texas	$	36.8	16.4	%	$	26.2	17.4	%	$	80.1	15.9	%	$	89.5	18.7	%
Georgia	26.3		11.7		15.0		10.0		56.0		11.1		48.8		10.2
Colorado	15.3		6.8		10.3		6.8		37.8		7.5		30.8		6.4
Pennsylvania	12.1		5.4		9.1		6.0		29.0		5.8		26.8		5.6
South Carolina	11.8		5.3		4.5		3.0		28.6		5.7		16.4		3.4
Utah	8.3		3.7		8.0		5.3		22.9		4.5		24.1		5.0
Arizona	11.0		4.9		4.3		2.9		21.7		4.3		13.3		2.8
Ohio	8.4		3.7		3.9		2.6		16.9		3.4		11.8		2.5
Oklahoma	7.2		3.2		5.2		3.5		16.7		3.3		16.1		3.4
Missouri	8.7		3.9		4.3		2.9		16.1		3.2		14.2		3.0
All others states	78.3		35.0		59.9		39.6		178.1		35.3		186.2		39.0
Total	$	224.2	100.0	%	$	150.7	100.0	%	$	503.9	100.0	%	$	478.0	100.0	%

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Item 2.  Management’s Discussion and Analysis of Financial Condition and Results of Operations

The following discussion and analysis of our financial condition and results of operations should be read in conjunction with our unaudited condensed consolidated financial statements and related notes appearing elsewhere in this Quarterly Report on Form 10-Q and our audited consolidated financial statements and the related notes and the discussion under the heading “Management’s Discussion and Analysis of Financial Condition and Results of Operations” included in our Annual Report on Form 10-K for the year ended December 31, 2022 filed with the Securities and Exchange Commission, or SEC, on February 22, 2023, or the 2022 10-K. This discussion, particularly information with respect to our future results of operations or financial condition, business strategy and plans and objectives of management for future operations, includes forward-looking statements that involve risks and uncertainties as described under the heading “Special Note Regarding Forward-Looking Statements” in this Quarterly Report on Form 10-Q. You should review the disclosure under the heading “Risk Factors” in this Quarterly Report on Form 10-Q and in the 2022 10-K for a discussion of important factors that could cause our actual results to differ materially from those anticipated in these forward-looking statements.

Our Business

Root is a tech-enabled insurance company revolutionizing personal insurance with a pricing model based upon fairness and a modern customer experience. We operate primarily a direct-to-consumer model in which we currently acquire the majority of our customers through mobile applications. We are also focused on expanding our embedded insurance platform, where we acquire customers through strategic partnerships.

We believe the Root advantage is derived from our unique ability to efficiently and effectively bind auto insurance policies quickly, through direct and embedded channels, aided by segmenting individual risk based on complex behavioral data and proprietary telematics. Our customer experience is built for ease of use and a product offering made possible with our full-stack insurance structure. These are all uniquely integrated into a single cloud-based technology platform that captures the entire insurance value chain—from customer acquisition to underwriting to claims and administration to ongoing customer engagement.

Our model benefits from portfolio maturity. As we scale the business and develop our embedded products, our results are disproportionately weighted towards new customers compared to traditional insurance carriers. As we build an underlying base of recurring customers, we expect the following financial impacts:

•Improved loss ratio. Renewal premiums, referring to premiums from a customer’s second term and beyond, have lower loss ratios as compared to new premiums in the customer’s first term. As we grow our business, we anticipate, consistent with industry norms, that a greater proportion of our premiums will be from customer renewals and drive down the loss ratio across our portfolio. We also continue to revise contracts to tighten underwriting and implement rate increases to control the impact of increased loss costs.

•Reduced marketing as a percentage of premium. Certain recurring customer premiums have no associated customer acquisition costs and minimal underwriting costs, driving profitability. As we grow our business, we anticipate, consistent with industry norms, that a greater proportion of our premiums will be from customer renewals without associated marketing costs.

•Increased revenue per customer. Over time we expect to refine our fee schedules to be more consistent with industry norms. This, paired with strengthened underwriting and pricing segmentation, will facilitate the opportunity to generate additional fee revenue per customer.

We use technology to drive efficiency across all functions, including distribution, underwriting, policy administration and claims in particular. We believe this allows us to operate with a cost to acquire and cost to serve advantage. We continue to develop machine learning loss models, which allows us to respond more quickly to changes in the market, improve pricing segmentation and take appropriate and timely rate actions. We efficiently acquire customers directly through multiple channels, including embedded, digital (performance), channel media, referrals and agency. Our evolving acquisition strategy includes utilizing our embedded platform through current and future embedded partners. Traditionally, our marketing costs have historically been well below industry averages, although in any given period, these costs can vary by acquisition strategy, channel mix, by state, or due to

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seasonality or due to the competitive environment. Today, we acquire the vast majority of our customers through mobile applications and our embedded platform. We believe that through prudent investment in and diversification of our marketing channels, including a focus on embedded insurance through our current and future strategic partners, and leveraging proprietary data science and technology will position us for more sustainable, long-term and profitable growth.

As a full-stack insurance company, we currently employ a “capital-efficient” model, which utilizes a variety of reinsurance structures. These include excess of loss and quota share reinsurance. Excess of loss provides us with volatility protection against a portion of large individual losses or an aggregation of losses from catastrophes. Quota share provides, among other advantages, regulatory surplus relief for growing companies. These reinsurance structures deliver three core objectives (1) top-line growth without a commensurate increase in regulatory capital requirements, (2) support of customer acquisition costs and (3) protection from outsized losses or tail events. We expect to continuously evaluate our utilization of third-party quota share reinsurance while scaling our business in order to operate a capital-efficient business model. As our gross loss ratios continue to improve and stabilize over the long-term, we expect to maintain the flexibility to modify our quota share levels to maximize the return to shareholders.

Given the significant impact of reinsurance on our results of operations, we use certain gross basis key performance indicators to manage and measure our business operations and enhance investor understanding of our business model prior to reinsurance. We believe our long-term success will be apparent through the progression of our gross metrics. Results of operations on a gross basis alone are not achievable under our regulatory landscape given our historical top-line growth and resulting capital requirements, which are relieved, in part, by obtaining reinsurance.

In addition to our gross basis metrics, management uses adjusted earnings before interest, tax, depreciation and amortization, or adjusted EBITDA, as an integral part of managing our business. We believe adjusted EBITDA provides investors with useful insight into our business because such measure eliminates the effects of certain charges that are not directly attributable to our underlying operating performance. For additional information, including definitions of these key metrics, see “— Key Performance Indicators” and for reconciliations of Direct Contribution and adjusted EBITDA to the most directly comparable generally accepted accounting principles in the United States, or GAAP, metric, see “— Non-GAAP Financial Measures.”

Recent Developments Affecting Comparability

General Macroeconomic Factors

Economic instability has led to acute inflationary pressures, supply chain disruptions, rising interest rates, a downturn in equity markets and bank failures. There is a risk of inflation remaining elevated for an extended period, which could cause claims and claim expenses to increase, impact the performance of our investment portfolio or have other adverse effects. We have seen an increase in auto repairable and medical costs. These cost increases have resulted in greater claims severity. We continue to file in multiple states to establish rates that more closely follow the evolving loss cost trends. Rising interest rates have increased the cost of capital and may limit our ability to raise additional capital.

Comprehensive Reinsurance

During the period we reduced the utilization of reinsurance through a strategic reduction of external quota share. The changes to the reinsurance program aim to deliver improved economics and capital efficiency. Our diversified approach to reinsurance allows us to optimize capital requirements while remaining flexible in response to changes in market conditions or changes specific to our own business. We may choose to amend, commute, and/or non-renew certain third-party reinsurance arrangements in the future, which may result in us retaining more of our business. To the extent we retain a larger share of our book of business, our capital requirements may increase.

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Key Performance Indicators

We regularly review a number of metrics, including the following key performance indicators, to evaluate our business, measure our performance, identify trends in our business, prepare financial projections and make strategic decisions. We believe these non-GAAP and operational measures are useful in evaluating our performance, in addition to our financial results prepared in accordance with GAAP. See the section titled “— Non-GAAP Financial Measures” for additional information regarding our use of direct contribution and adjusted EBITDA and their reconciliations to the most directly comparable GAAP measures.

	Three Months Ended September 30,						Nine Months Ended September 30,
	2023			2022			2023			2022
	(dollars in millions, except premiums per policy)
Policies in force	259,522			255,279			259,522			255,279
Premiums per policy	$	1,398		$	1,150		$	1,398		$	1,150
Premiums in force	$	725.6		$	587.1		$	725.6		$	587.1
Gross premiums written	$	224.2		$	150.7		$	503.9		$	478.0
Gross premiums earned	$	159.8		$	155.3		$	421.4		$	500.8
Gross profit/(loss)	$	11.2		$	(8.3)		$	29.4		$	(28.1)
Net loss	$	(45.8)		$	(66.4)		$	(123.4)		$	(239.4)
Direct contribution	$	37.0		$	11.5		$	84.9		$	17.7
Adjusted EBITDA	$	(19.4)		$	(46.4)		$	(42.6)		$	(161.4)
Net loss and LAE ratio	85.8		%	117.9		%	93.2		%	123.3		%
Net expense ratio	57.3		%	67.2		%	56.9		%	76.0		%
Net combined ratio	143.1		%	185.1		%	150.1		%	199.3		%
Gross loss ratio	65.6		%	77.9		%	67.4		%	83.2		%
Gross LAE ratio	9.6		%	10.5		%	10.2		%	9.8		%
Gross expense ratio	43.5		%	42.0		%	42.3		%	46.5		%
Gross combined ratio	118.7		%	130.4		%	119.9		%	139.5		%
Gross accident period loss ratio	68.0		%	79.3		%	67.9		%	81.3		%

Policies in Force

We define policies in force as the number of current and active auto insurance policyholders underwritten by us as of the period end date. We view policies in force as an important metric to assess our financial performance because policy growth drives our revenue growth, expands brand awareness, deepens our market penetration, and generates additional data to continue to improve the functioning of our platform.

Premiums per Policy

We define premiums per policy as the ratio of gross premiums written on auto insurance policies in force at the end of the period divided by policies in force. We view premiums per policy as an important metric since the higher the premiums per policy the greater the amount of earned premium we expect from each policy.

Premiums in Force

We define premiums in force as premiums per policy multiplied by policies in force multiplied by two. We view premiums in force as an estimate of annualized run rate of gross premiums written as of a given period. Since our auto policies are six-month policies, we multiply this figure by two in order to determine an annualized amount of premiums in force. We view this as an important metric because it is an indicator of the size of our portfolio of policies as well as an indicator of expected earned premium over the coming 12 months. Premiums in force is not a forecast of future revenue nor is it a reliable indicator of revenue expected to be earned in any given period. We

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believe that our calculation of premiums in force is useful to investors and analysts because it captures the impact of fluctuations in customers and premiums per policy at the end of each reported period, without adjusting for known or projected policy updates, cancellations and non-renewals.

Gross Premiums Written

We define gross premiums written, as the total amount of gross premium on policies that were bound during the period less the prorated impact of policy cancellations. Gross premiums written includes direct premiums and assumed premiums. We view gross premiums written as an important metric because it is the metric that most closely correlates with changes in gross premiums earned. We use gross premiums written, which excludes the impact of premiums ceded to reinsurers, to manage our business because we believe that it reflects the business volume and direct economic benefit generated by our customer acquisition activities, which along with our underlying underwriting and claims operations (gross loss ratio and gross LAE) are the key drivers of our future profit opportunities. Additionally, premiums ceded to reinsurers can change significantly based on the type and mix of reinsurance structures we use, and, as such, we have the optionality to fully retain the premiums from customers acquired in the future.

Gross Premiums Earned

We define gross premiums earned as the amount of gross premium that was earned during the period. Premiums are earned over the period in which insurance protection is provided, which is typically six months. Gross premiums earned includes direct premiums and assumed premiums. We view gross premiums earned as an important metric as it allows us to evaluate our premium levels prior to the impacts of reinsurance. It is the primary driver of our consolidated GAAP revenues. As with gross premiums written, we use gross premiums earned, which excludes the impact of premiums ceded to reinsurers to manage our business, because we believe that it reflects the business volume and direct economic benefit generated by our customer acquisition activities, which along with our underlying underwriting and claims operations (gross loss ratio and gross LAE) are the key drivers of our future profit opportunities.

Gross Profit/(Loss)

We define gross profit/(loss) as total revenue minus net loss and LAE and other insurance expense (benefit). We view gross profit/(loss) as an important metric because we believe it is informative of the financial performance of our core insurance business.

Direct Contribution

We define direct contribution, a non-GAAP financial measure, as gross profit/(loss) excluding net investment income, net realized gains on investments, report costs, overhead allocated based on headcount, or Overhead, and salaries, health benefits, bonuses, employee retirement plan-related expenses and employee share-based compensation expense, or Personnel Costs, licenses, net commissions, professional fees and other expenses, ceded premiums earned, ceded loss and LAE, and net ceding commission and other. Net ceding commission and other is comprised of ceding commission received in connection with reinsurance ceded, partially offset by amortization of excess ceding commission, and other impacts of reinsurance ceded, which are included in other insurance expense. After these adjustments, the resulting calculation is inclusive of only those gross variable costs of revenue incurred on the successful acquisition of business. We view direct contribution as an important metric because we believe it measures progress towards the profitability of our total policy portfolio prior to the impact of reinsurance.

See the section titled “— Non-GAAP Financial Measures” for a reconciliation of total revenue to direct contribution.

Adjusted EBITDA

We define adjusted EBITDA, a non-GAAP financial measure, as net loss excluding interest expense, income tax expense, depreciation and amortization, share-based compensation, warrant compensation expense, restructuring charges, write-off of prepaid marketing expenses, legal fees and other items that do not reflect our ongoing operating

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performance. After these adjustments, the resulting calculation represents expenses directly attributable to our operating performance. We use adjusted EBITDA as an internal performance measure in the management of our operations because we believe it provides management and other users of our financial information useful insight into our results of operations and underlying business performance. Adjusted EBITDA should not be viewed as a substitute for net loss calculated in accordance with GAAP, and other companies may define adjusted EBITDA differently.

See the section titled “— Non-GAAP Financial Measures” for a reconciliation of net loss to adjusted EBITDA.

Net Loss and LAE Ratio

We define net loss and LAE ratio expressed as a percentage, as the ratio of net loss and LAE to net premiums earned. We view net loss and LAE ratio as important metric because it allows us to evaluate loss trends as a percentage of net premiums and believe it is useful for investors to evaluate those separately from other operating expenses.

Net Expense Ratio

We define net expense ratio expressed as a percentage, as the ratio of all operating expenses less loss and LAE and less fee income to net premiums earned. We view net expense ratio as important because it allows us to analyze our expense and acquisition trends, net of fee income, and allows investors to evaluate these expenses exclusive of our loss and LAE expenses.

Net Combined Ratio

We define net combined ratio expressed as a percentage, as the sum of net loss and LAE ratio and net expense ratio. We view net combined ratio as important because it allows us to analyze our underwriting result trends and is a key indicator of overall profitability and health of the overall business. We believe it is useful to investors to evaluate these components separately and in the aggregate when reviewing our underwriting performance. A net combined ratio under 100% indicates an underwriting profit, while a net combined ratio greater than 100% indicates an underwriting loss.

Gross Loss Ratio

We define gross loss ratio expressed as a percentage, as the ratio of gross losses to gross premiums earned. Gross loss ratio excludes LAE. We view gross loss ratio as an important metric because it allows us to evaluate incurred losses and LAE separately prior to the impact of reinsurance.

Gross LAE Ratio

We define gross LAE ratio expressed as a percentage, as the ratio of gross LAE to gross premiums earned. We view gross LAE ratio as an important metric because it allows us to evaluate incurred losses and LAE separately. Currently, we do not cede any of our LAE to our third-party quota share reinsurance treaties; therefore, we actively monitor LAE ratio as it has a direct impact on our results regardless of our reinsurance strategy.

Gross Expense Ratio

We define gross expense ratio expressed as a percentage as the ratio of gross operating expenses less loss and LAE and less fee income to gross premiums earned. We view gross expense ratio as important because it allows us to analyze the underlying expense base of the business and establish expense targets, prior to the impact of reinsurance. We believe gross expense ratio is useful for investors to further evaluate business health and performance, prior to the impact of reinsurance.

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Gross Combined Ratio

We define gross combined ratio expressed as a percentage as the sum of the gross loss ratio, gross LAE ratio and gross expense ratio. We view gross combined ratio as important because it allows us to evaluate financial performance and establish targets that we believe more closely reflect the underlying performance and profitability of the business prior to reinsurance. Further, we believe it is useful for investors to evaluate these components separately and in the aggregate when reviewing our gross underwriting performance. A gross combined ratio under 100% indicates an underwriting profit while a gross combined ratio greater than 100% indicates an underwriting loss, prior to the impact of reinsurance.

Gross Accident Period Loss Ratio

Gross accident period loss ratio, expressed as a percentage, represents all losses and claims expected to arise from insured events that occurred during the applicable period regardless of when they are reported and finally settled divided by gross premiums earned for the same period. Changes to our loss reserves are the primary driver of the difference between our gross accident period loss ratio and gross loss ratio. We believe that gross accident period loss ratio is useful in evaluating expected losses prior to the impact of reinsurance.

Components of Our Results of Operations

Revenue

We generate revenue from net premiums earned, net investment income, net realized gains on investments, fee income and other income.

Net Premiums Earned

Premiums written are deferred and earned pro rata over the policy period. Net premiums earned represents the earned portion of our gross premiums written, less the earned portion that is ceded to third-party reinsurers under our reinsurance agreements.

Net Investment Income

Net investment income represents interest earned from our cash and cash equivalents and fixed maturity and short-term investments and unrealized gains and losses from our private equity investments less investment expenses. Net investment income is directly correlated with the overall size of our investment portfolio, market level of interest rates and changes in the fair value of our private equity investments. Net investment income will vary with the size and composition of our investment portfolio, market returns and the investment strategy.

Net Realized Gains on Investments

Net realized gains on investments represents the difference between the amount received by us on the sale of an investment as compared to the investment’s amortized cost basis.

Fee Income

For those policyholders who pay premiums on an installment basis, we charge a flat fee for each installment related to the additional administrative costs associated with processing more frequent billing. We recognize this fee income in the period in which we process each installment.

Other Income

Other income is primarily comprised of revenue earned from distributing website and mobile application policy inquiry leads in geographies where we do not have a presence, recognized when we generate the lead; commissions earned for homeowners policies placed with third-party insurance companies where we have no exposure to the insured risk, recognized on the effective date of the associated policy.

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Operating Expenses

Our operating expenses consist of loss and LAE, sales and marketing, other insurance expense (benefit), technology and development, and general and administrative expenses.

Loss and Loss Adjustment Expenses

Loss and LAE include the costs incurred for claims, payments made and estimated future payments to be made to or on behalf of our policyholders, including expenses needed to adjust or settle claims, net of amounts ceded to reinsurers. Loss and LAE include an amount determined using adjuster determined case-base estimates for reported claims and actuarial determined unpaid claim estimates using past experience and historical emergence patterns for unreported losses and LAE. These reserves are a liability established to cover the estimated ultimate cost to settle insured losses. The unpaid loss estimates consider loss trends, mix of business, and other risk factors impacting claims settlement. The method used to estimate unpaid LAE liability is based on claims transaction data, including the relative cost of adjusting and settling a range of claim types from express material damage claims to more complex injury cases.

Loss and LAE are net of amounts ceded to reinsurers. We enter into reinsurance contracts to limit our exposure to potential losses as well as to provide additional capacity to write more business. These expenses are a function of the size and term of the insurance policies we write and the loss experience associated with the underlying risks. This includes an allowance for credit losses based on the probability of default and expected loss of a reinsurer. Loss and LAE may be paid out over a period of years.

Various other expenses incurred during claims processing are considered LAE. These amounts include Personnel Costs for claims related employees; software expense; internally developed software amortization; and Overhead.

Sales and Marketing

Sales and marketing expense includes spending related to performance and embedded channels, channel media, advertising, branding, public relations, sponsorship, consumer insights and referral fees. These expenses also include related Personnel Costs, Overhead and certain warrant compensation expense related to our embedded channel. We incur sales and marketing expenses for all product offerings. Sales and marketing are expensed as incurred. Certain warrant compensation expense is recognized on a pro-rata basis considering progress toward completing the Integrated Platform under the Carvana commercial agreement.

We plan to continue investing in and diversifying our marketing channels, including costs incurred related to our embedded channel, to attract and acquire new customers, increase our brand awareness, and expand our product offerings within certain markets. We expect that in the long term, our sales and marketing will decrease as a percentage of revenue as the proportion of renewals to our total business increases.

Other Insurance Expense (Benefit)

Other insurance expense (benefit) includes underwriting expenses, credit card and policy processing expenses, premium write-offs, insurance license expenses, certain warrant compensation expense related to our embedded channel, and Personnel Costs and Overhead related to actuarial and certain data science activities. Other insurance expense (benefit) also includes amortization of deferred acquisition costs like certain commissions, premium taxes and report costs related to the successful acquisition of a policy. Other insurance expense (benefit) is expensed as incurred, except for costs related to deferred acquisition costs that are capitalized and subsequently amortized over the same period in which the related premiums are earned. These expenses are also recognized net of ceding commissions earned from reinsurance contracts. Certain warrant compensation expense is recognized on a pro-rata basis considering progress toward achieving milestones for policies originated through the Integrated Platform as defined under the Carvana commercial agreement.

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Technology and Development

Technology and development expense consists of software development costs related to our mobile application and homegrown information technology systems; third-party services related to infrastructure support; Personnel Costs and Overhead for engineering, product, technology, and certain data science activities; and amortization of internally developed software. Technology and development is expensed as incurred, except for development and testing costs related to internally developed software that are capitalized and subsequently amortized over the expected useful life. Over time, we expect technology and development to decrease as a percentage of revenue.

General and Administrative

General and administrative expenses primarily relate to external professional service expenses; Personnel Costs and Overhead for corporate functions; and depreciation expense for computers, furniture and other fixed assets; write-offs; and restructuring costs which include employee costs, real estate exit costs and other costs. General and administrative expenses are expensed as incurred. We expect general and administrative expenses to decrease as a percentage of total revenue over time.

Non-Operating Expenses

Interest Expense

Interest expense is not an operating expense; therefore, we include these expenses below operating expenses. Interest expense primarily relates to interest incurred on our long-term debt, certain fees that are expensed as incurred and amortization of debt issuance costs. In addition, changes in the fair value of warrant liabilities that were associated with our long-term debt are recorded as interest expense.

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Results of Operations

Comparison of the Three Months Ended September 30, 2023 and 2022

The following table presents our results of operations for the periods indicated:

	Three Months Ended September 30,
	2023		2022		$ Change		% Change
	(dollars in millions)
Revenues:
Net premiums earned	$	100.0	$	68.6	$	31.4	45.8	%
Net investment income	9.0		0.9		8.1		900.0	%
Fee income	6.2		3.8		2.4		63.2	%
Other income	0.1		0.4		(0.3)		(75.0)	%
Total revenues	115.3		73.7		41.6		56.4	%
Operating expenses:
Loss and loss adjustment expenses	85.8		80.9		4.9		6.1	%
Sales and marketing	13.1		8.1		5.0		61.7	%
Other insurance expense	18.3		1.1		17.2		1,563.6	%
Technology and development	11.1		14.3		(3.2)		(22.4)	%
General and administrative	21.0		26.4		(5.4)		(20.5)	%
Total operating expenses	149.3		130.8		18.5		14.1	%
Operating loss	(34.0)		(57.1)		23.1		(40.5)	%
Interest expense	(11.8)		(9.3)		(2.5)		26.9	%
Loss before income tax expense	(45.8)		(66.4)		20.6		(31.0)	%
Income tax expense	—		—		—		—	%
Net loss	(45.8)		(66.4)		20.6		(31.0)	%
Other comprehensive loss:
Changes in net unrealized losses on investments	(0.7)		(2.3)		1.6		(69.6)	%
Comprehensive loss	$	(46.5)	$	(68.7)	$	22.2	(32.3)	%

Revenue

Net Premiums Earned

Net premiums earned increased $31.4 million, or 45.8%, to $100.0 million for the three months ended September 30, 2023 compared to the same period in 2022. The increase was primarily due to reduced cessions of gross premiums earned to reinsurers between periods and an increase in premium per policy resulting from rate actions. In addition, net premiums earned increased due to commutations of certain reinsurance agreements executed in the third quarter of 2023.

During the three months ended September 30, 2023 and 2022, we ceded approximately 37.4% and 55.8% of our gross premiums earned to third-party reinsurers, respectively. The change in cessions between periods was primarily driven by a strategic reduction of external quota share reinsurance and commutations of certain reinsurance agreements.

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The following table presents gross premiums written, ceded premiums written, net premiums written, gross premiums earned, ceded premiums earned and net premiums earned for the three months ended September 30, 2023 and 2022:

	Three Months Ended September 30,
	2023		2022		$ Change		% Change
	(dollars in millions)
Gross premiums written	$	224.2	$	150.7	$	73.5	48.8	%
Ceded premiums written	(22.3)		(81.0)		58.7		(72.5)	%
Net premiums written	201.9		69.7		132.2		189.7	%
Gross premiums earned	159.8		155.3		4.5		2.9	%
Ceded premiums earned	(59.8)		(86.7)		26.9		(31.0)	%
Net premiums earned	$	100.0	$	68.6	$	31.4	45.8	%

The increase in gross premiums earned was primarily due to higher policies in force driven by greater sales and marketing spend deployment for the three months ended September 30, 2023 compared to the same period in 2022. We also experienced a 21.6% increase in premium per policy for automobile insurance primarily attributable to rate actions.

Net Investment Income

Net investment income increased $8.1 million, or 900.0%, to $9.0 million for the three months ended September 30, 2023 compared to the same period in 2022. The increase was primarily driven by $7.9 million in higher interest and dividends received as a result of investing more in higher yielding investments.

Operating Expenses

Loss and Loss Adjustment Expenses

Loss and LAE increased $4.9 million, or 6.1%, to $85.8 million for the three months ended September 30, 2023 compared to the same period in 2022. The increase was primarily driven by reduced cessions of losses to reinsurers and commutations of certain reinsurance agreements which includes $2.8 million expense related to an allowance for credit losses. This was partially offset by better loss experience for the three months ended September 30, 2023 compared to the same period ended in 2022.

Gross accident period loss ratios decreased to 68.0% for the three months ended September 30, 2023, from 79.3% for the same period in 2022. The change in the ratios was mainly driven by growth in average premium per policy primarily attributable to rate actions. This was partially offset by higher loss costs as a result of increased severity per claim due to higher vehicle repair and medical costs. We experienced a 10% increase in severity per claim and claim frequency remained flat for the three months ended September 30, 2023 compared to the same period in 2022. The claim severity and frequency estimates are based on bodily injury, collision, and property damage coverages, the claim frequency estimates are tenure mix adjusted.

Sales and Marketing

Sales and marketing expense increased $5.0 million, or 61.7%, to $13.1 million for the three months ended September 30, 2023 compared to the same period in 2022. The increase was primarily due to an increased deployment of performance marketing spend of $11.4 million to drive growth and deeper market penetration in the states in which we operate. This was partially offset by a $4.5 million decrease in content development, sponsorship, marketing partnership and advertising costs due to a shift in our direct marketing strategy. In addition, we experienced a $2.0 million decrease in Personnel Costs as a result of a decrease in headcount, primarily attributable to the involuntary workforce reductions in 2022.

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Other Insurance Expense

Other insurance expense increased $17.2 million, or 1,563.6%, to $18.3 million for the three months ended September 30, 2023 compared to the same period in 2022. The increase was primarily driven by a $7.6 million decrease in ceding commissions contra-expense driven primarily by commutations executed in the third quarter of 2023, and $6.4 million increase in report costs due to an increase in customer applications and new writings. Further, we incurred a $3.6 million increase in Carvana warrant expense as a result of policies originating from the Integrated Platform. We also experienced a $3.0 million increase in amortization of deferred acquisition costs for certain commissions. This was partially offset by a $1.9 million decrease in premium write-offs. We also experienced a $1.1 million decrease in Personnel Costs as a result of a decrease in headcount due to the involuntary workforce reductions in 2022.

Technology and Development

Technology and development decreased $3.2 million, or 22.4%, to $11.1 million for the three months ended September 30, 2023 compared to the same period in 2022. The decrease was primarily driven by a $2.3 million decrease in Personnel Costs as a result of a decrease in headcount, primarily attributable to the involuntary workforce reductions in 2022. We also experienced a $1.2 million decrease in software development expense as a result of initiatives to reduce operating costs.

General and Administrative

General and administrative decreased $5.4 million, or 20.5%, to $21.0 million for the three months ended September 30, 2023 compared to the same period in 2022. The decrease was primarily driven by a $6.3 million decrease in Personnel Costs as a result of a decrease in headcount, primarily attributable to the involuntary workforce reductions in 2022. This was partially offset by a $1.9 million increase in restructuring costs.

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Comparison of the Nine Months Ended September 30, 2023 and 2022

The following table presents our results of operations for the periods indicated:

	Nine Months Ended September 30,
	2023		2022		$ Change		% Change
	(dollars in millions)
Revenues:
Net premiums earned	$	223.9	$	221.6	$	2.3	1.0	%
Net investment income	22.5		2.2		20.3		922.7	%
Net realized gains on investments	—		1.1		(1.1)		(100.0)	%
Fee income	13.2		13.1		0.1		0.8	%
Other income	0.6		1.5		(0.9)		(60.0)	%
Total revenues	260.2		239.5		20.7		8.6	%
Operating expenses:
Loss and loss adjustment expenses	208.6		273.3		(64.7)		(23.7)	%
Sales and marketing	22.8		44.8		(22.0)		(49.1)	%
Other insurance expense (benefit)	22.2		(5.7)		27.9		489.5	%
Technology and development	32.4		46.1		(13.7)		(29.7)	%
General and administrative	63.2		96.4		(33.2)		(34.4)	%
Total operating expenses	349.2		454.9		(105.7)		(23.2)	%
Operating loss	(89.0)		(215.4)		126.4		(58.7)	%
Interest expense	(34.4)		(24.0)		(10.4)		43.3	%
Loss before income tax expense	(123.4)		(239.4)		116.0		(48.5)	%
Income tax expense	—		—		—		—	%
Net loss	(123.4)		(239.4)		116.0		(48.5)	%
Other comprehensive loss:
Changes in net unrealized losses on investments	(0.8)		(7.3)		6.5		(89.0)	%
Comprehensive loss	$	(124.2)	$	(246.7)	$	122.5	(49.7)	%

Revenue

Net Premiums Earned

Net premiums earned increased $2.3 million, or 1.0%, to $223.9 million, for the nine months ended September 30, 2023 compared to the same period in 2022. The increase was primarily due to reduced cessions of gross premiums earned to reinsurers between periods, greater premium per policy resulting from rate actions and commutations of certain reinsurance agreements executed in the third quarter of 2023. This was partially offset by lower gross premiums earned for the nine months ended September 30, 2023 compared to the same period in 2022

During the nine months ended September 30, 2023 and 2022, we ceded approximately 46.9% and 55.8% of our gross premiums earned to third-party reinsurers, respectively. The change in cessions between periods was primarily driven by a strategic reduction of quota share reinsurance and commutations of certain reinsurance agreements.

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The following table presents gross premiums written, ceded premiums written, net premiums written, gross premiums earned, ceded premiums earned and net premiums earned for the nine months ended September 30, 2023 and 2022:

	Nine Months Ended September 30,
	2023		2022		$ Change		% Change
	(dollars in millions)
Gross premiums written	$	503.9	$	478.0	$	25.9	5.4	%
Ceded premiums written	(159.4)		(264.5)		105.1		(39.7)	%
Net premiums written	344.5		213.5		131.0		61.4	%
Gross premiums earned	421.4		500.8		(79.4)		(15.9)	%
Ceded premiums earned	(197.5)		(279.2)		81.7		(29.3)	%
Net premiums earned	$	223.9	$	221.6	$	2.3	1.0	%

The decrease in gross premiums earned was primarily due to strong growth in new writings during the nine months ended September 30, 2023, that is continuing to earn in over the policy period. This decrease was partially offset by a 21.6% increase in premium per policy for automobile insurance primarily attributable to rate actions and higher policies in force.

Net Investment Income

Net investment income increased $20.3 million, or 922.7%, to $22.5 million for the nine months ended September 30, 2023 compared to the same period in 2022. The increase was primarily driven by $19.6 million in higher interest and dividends received as a result of investing more in higher yielding investments.

Operating Expenses

Loss and Loss Adjustment Expenses

Loss and LAE decreased $64.7 million, or 23.7%, to $208.6 million for the nine months ended September 30, 2023 compared to the same period in 2022. The decrease was primarily due to better loss experience for the nine months ended September 30, 2023 compared to the same period in 2022. This was partially offset by reduced cessions of losses to reinsurers and commutations of certain reinsurance agreements which includes $2.8 million expense related to an allowance for credit losses for the nine months ended September 30, 2023 compared to the same period in 2022.

Gross accident period loss ratios decreased to 67.9% for the nine months ended September 30, 2023, from 81.3% for the same period in 2022. The change in the ratios was driven by growth in average premium per policy primarily attributable to rate actions. This was partially offset by higher loss costs as a result of increased severity per claim due to higher vehicle repair and medical costs. We experienced an 8% increase in severity per claim and a 5% decrease in claim frequency for the nine months ended September 30, 2023 compared to the same period in 2022. The claim severity and frequency estimates are based on bodily injury, collision, and property damage coverages, the claim frequency estimates are tenure mix adjusted.

Sales and Marketing

Sales and marketing expense decreased $22.0 million, or 49.1%, to $22.8 million for the nine months ended September 30, 2023 compared to the same period in 2022. The decrease was due to a $20.2 million decrease in content development, marketing partnership, sponsorship and advertising costs due to a shift in our direct marketing strategy. In addition, we experienced an $8.8 million decline in warrant compensation expense related to the completion of the Integrated Platform pursuant to the Carvana commercial agreement in the prior year. We also experienced a $5.8 million decrease in Personnel Costs as a result of a decrease in headcount, primarily attributable

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to the involuntary workforce reductions in 2022. This was partially offset by a $12.7 million increase in performance marketing spend to drive growth and deeper market penetration in the states in which we operate.

Other Insurance Expense (Benefit)

Other insurance expense (benefit) increased $27.9 million, or 489.5%, to an expense of $22.2 million for the nine months ended September 30, 2023 compared to the same period in 2022. The increase was primarily driven by a $13.8 million decrease in net ceding commission contra-expense as a result of a decline in ceded premiums and commutations executed in the third quarter of 2023. We also experienced an $11.9 million increase in Carvana warrant expense as a result of policies originating from the Integrated Platform and an $8.6 million increase in report costs due to an increase in customer applications and new writings. In addition, we experienced a $6.7 million increase in amortization of deferred acquisition costs for certain commissions. This was partially offset by a $4.1 million decrease in Personnel Costs as a result of a decrease in headcount due to the involuntary workforce reductions in 2022. In addition, we experienced a $2.5 million decrease in premium taxes and a $1.8 million decrease in payment processing fees.

Technology and Development

Technology and development decreased $13.7 million, or 29.7%, to $32.4 million for the nine months ended September 30, 2023 compared to the same period in 2022. The decrease was primarily driven by an $11.0 million decrease in Personnel Costs as a result of a decrease in headcount, primarily attributable to the involuntary workforce reductions in 2022. We also experienced a $3.5 million decrease in software development expense as a result of initiatives to reduce operating costs.

General and Administrative

General and administrative decreased $33.2 million, or 34.4%, to $63.2 million for the nine months ended September 30, 2023 compared to the same period in 2022. The decrease was primarily driven by a $23.8 million decrease in Personnel Costs as a result of a decrease in headcount, primarily attributable to the involuntary workforce reductions in 2022, and a $10.1 million write-off of prepaid marketing expense recognized in 2022.

Non-Operating Expenses

Interest Expense

Interest expense increased $10.4 million, or 43.3%, to $34.4 million for the nine months ended September 30, 2023 compared to the same period in 2022. The increase was primarily due to a $10.1 million increase in debt interest expense primarily as a result of a greater average interest rate as of September 30, 2023 compared to the same period in 2022.

Other Comprehensive Loss

Changes in Net Unrealized Losses on Investments

Changes in net unrealized losses on investments decreased $6.5 million, or 89.0%, to $0.8 million for the nine months ended September 30, 2023 compared to the same period in 2022. The decrease is primarily attributable to investments being reinvested at maturity in securities that reflect the current interest rate environment.

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Non-GAAP Financial Measures

The non-GAAP financial measures below have not been calculated in accordance with GAAP and should be considered in addition to results prepared in accordance with GAAP and should not be considered as a substitute for, or superior to, GAAP results. In addition, direct contribution and adjusted EBITDA should not be construed as indicators of our operating performance, liquidity or cash flows generated by operating, investing and financing activities, as there may be significant factors or trends that they fail to address. We caution investors that non-GAAP financial information, by its nature, departs from traditional accounting conventions. Therefore, its use can make it difficult to compare our current results with our results from other reporting periods and with the results of other companies.

Our management uses these non-GAAP financial measures, in conjunction with GAAP financial measures, as an integral part of managing our business and to, among other things: (1) monitor and evaluate the performance of our business operations and financial performance; (2) facilitate internal comparisons of the historical operating performance of our business operations; (3) facilitate external comparisons of the results of our overall business to the historical operating performance of other companies that may have different capital structures and debt levels; (4) review and assess the operating performance of our management team; (5) analyze and evaluate financial and strategic planning decisions regarding future operating investments; and (6) plan for and prepare future annual operating budgets and determine appropriate levels of operating investments.

Direct Contribution

For the definition of direct contribution and why management believes this measure provides useful information to investors, see “— Key Performance Indicators.”

The following table provides a reconciliation of total revenue to direct contribution for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Total revenue	$	115.3	$	73.7	$	260.2	$	239.5
Loss and loss adjustment expenses	(85.8)		(80.9)		(208.6)		(273.3)
Other insurance (expense) benefit	(18.3)		(1.1)		(22.2)		5.7
Gross profit/(loss)	11.2		(8.3)		29.4		(28.1)
Net investment income	(9.0)		(0.9)		(22.5)		(2.2)
Net realized gains on investments	—		—		—		(1.1)
Adjustments from other insurance expense (benefit)(1)	21.7		9.7		49.6		26.8
Ceded premiums earned	59.8		86.7		197.5		279.2
Ceded loss and loss adjustment expenses	(34.4)		(56.5)		(118.3)		(192.4)
Net ceding commission and other(2)	(12.3)		(19.2)		(50.8)		(64.5)
Direct contribution	$	37.0	$	11.5	$	84.9	$	17.7

______________

(1) Adjustments from other insurance expense (benefit) includes report costs, Personnel Costs, Overhead, licenses, net commissions, professional fees and other.

(2) Net ceding commission and other is comprised of ceding commissions received in connection with reinsurance ceded, partially offset by amortization of excess ceding commission and other impacts of reinsurance ceded.

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Adjusted EBITDA

For the definition of adjusted EBITDA and why management believes this measure provides useful information to investors, see “— Key Performance Indicators.”

The following table provides a reconciliation of net loss to adjusted EBITDA for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Net loss	$	(45.8)	$	(66.4)	$	(123.4)	$	(239.4)
Adjustments:
Interest expense	11.1		8.5		32.2		22.0
Income tax expense	—		—		—		—
Depreciation and amortization	2.7		2.2		8.0		7.5
Share-based compensation	4.7		7.8		12.0		19.7
Warrant compensation expense	5.0		1.5		13.3		10.3
Restructuring costs(1)	1.9		—		9.4		8.4
Write-offs and other(2)	1.0		—		5.9		10.1
Adjusted EBITDA	$	(19.4)	$	(46.4)	$	(42.6)	$	(161.4)

______________

(1) Restructuring costs consist of employee costs, real estate exit costs, and other. This includes share-based compensation of zero and $0.4 million for the three and nine months ended September 30, 2023, respectively, and zero and $2.1 million for the three and nine months ended September 30, 2022, respectively. This also includes depreciation and amortization of zero and $0.2 million for the three and nine months ended September 30, 2023, respectively, and $0.1 million and $1.4 million for the three and nine months ended September 30, 2022, respectively. For further information on restructuring costs, see Note 9, “Restructuring Costs,” in the Notes to Condensed Consolidated Financial Statements.

(2) Write-offs and other primarily reflects legal costs, write-off of prepaid marketing expense and other items that do not reflect our ongoing operating performance. This includes write-off of prepaid marketing expenses of zero and $10.1 million for the three and nine months ended September 30, 2022, respectively. Legal and other fees related to the purported misappropriation of funds by a former senior marketing employee in 2022 of $1.0 million and $3.4 million for the three and nine months ended September 30, 2023, respectively.

Liquidity and Capital Resources

General

Since inception, we have financed operations primarily through sales of insurance policies and the net proceeds we have received from our issuance of stock and debt and from sales of investments. Cash generated from operations is highly dependent on being able to efficiently acquire and maintain customers while pricing our insurance products appropriately. We are continuously evaluating alternatives for efficiently funding our ongoing operations. We expect, from time to time, to engage in a variety of financing transactions for such purposes.

Certain events may impact our liquidity such as the economic instability resulting in acute inflationary pressures, supply chain disruptions, rising interest rates, a downturn in equity markets, bank failures and our utilization of reinsurance. There is a risk of inflation remaining elevated for an extended period, which could cause claims and claim expenses to increase, impact the performance of our investment portfolio or have other adverse effects. Rising interest rates have increased the cost of capital and may limit our ability to raise additional capital. We utilize reinsurance arrangements to grow our business in a capital-efficient manner and mitigate risk. Over time, our strategy continues to evolve and we may choose to amend, commute, and/or non-renew certain third-party reinsurance agreements, which may result in us retaining more of our business in the future. To the extent we retain a larger share of our book of business, our capital requirements may increase.

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Regulatory Considerations

We are organized as a holding company, but our primary operations are conducted by two of our wholly-owned insurance subsidiaries, Root Insurance Company and Root Property & Casualty Insurance Company, both Ohio-domiciled insurance companies. The payment of dividends by our insurance subsidiaries is subject to restrictions set forth in the insurance laws and regulations of the State of Ohio. To date, our insurance subsidiaries have not paid any dividends and, as of September 30, 2023, they were not permitted to pay any dividends without approval of the applicable superintendent, commissioner and/or director.

If our insurance subsidiaries’ businesses grow or the regulatory requirements change, the amount of capital we are required to maintain to satisfy our risk-based capital requirements may increase significantly. To comply with these regulations, we may be required to maintain capital in the insurance subsidiaries that we would otherwise invest in our growth and operations. As of September 30, 2023, our insurance subsidiaries maintained a risk-based capital level that is in excess of an amount that would require any corrective actions on our part.

Our wholly-owned, Cayman Islands-based reinsurance subsidiary, Root Reinsurance Company, Ltd., or Root Re, maintains a Class B(iii) insurer license under Cayman Islands Monetary Authority, or CIMA. At September 30, 2023, Root Re was subject to compliance with certain capital levels and a net premiums earned to capital ratio of 15:1, which we maintained as of September 30, 2023. The capital ratio can fluctuate at Root Re’s election, subject to regulatory approval. Root Re’s primary sources of funds are capital contributions from the holding company, assumed insurance premiums and net investment income. These funds are primarily used to pay claims and operating expenses and to purchase investments. Root Re must receive approval from CIMA before it can pay any dividend to the holding company.

Financing Arrangements

On January 26, 2022, we closed on a $300.0 million five-year term loan, or Term Loan. The maturity of the Term Loan is January 27, 2027. Interest is payable quarterly and is determined on a floating interest rate calculated on the Secured Overnight Financing Rate, with a 1.0% floor, plus 9.0%.

Liquidity

As of September 30, 2023, we had $635.3 million in cash and cash equivalents, of which $502.2 million was held outside of regulated insurance entities. We also had $167.1 million in marketable securities.

Our cash and cash equivalents primarily consist of bank deposits and money market funds. Our marketable securities primarily consist of U.S. Treasury securities and agencies, municipal securities, corporate debt securities, residential and commercial mortgage-backed securities, and other debt obligations.

We believe that our existing cash and cash equivalents, marketable securities and cash flow from operations will be sufficient to support short-term working capital and capital expenditure requirements for at least the next 12 months and for the foreseeable future thereafter.

Our long-term capital requirements depend on many factors, including our insurance premium growth rate, rate adequacy, renewal activity, the timing and the amount of cash received from customers, the performance of our products, including the success of our embedded partnerships, loss cost trends, the timing and extent of spending to support development efforts, the introduction of new and enhanced products, the continuing market adoption of offerings on our platform, operating costs, and the ongoing uncertainty in global markets.

As of September 30, 2023, we expect to incur approximately $1.7 million of employee compensation expense, dependent upon continuous employment for certain employees, to be recognized ratably in the fourth quarter of 2023. We expect a cash expenditure of approximately $8.3 million related to these employee compensation costs in the first quarter of 2024. For additional information regarding organizational realignment and involuntary workforce reductions refer to Note 9, “Restructuring Costs,” in the Notes to Condensed Consolidated Financial Statements.

Currently, our debt covenants require cash and cash equivalents held in entities other than our insurance subsidiaries to be at least $200.0 million at all times. This threshold may be reduced to $150.0 million under two sets

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of circumstances: issuing 62,500 insurance policies through our Carvana embedded product and achieving a ratio of direct contribution to gross premiums earned of 12%; or ceasing any customer acquisition spend outside of the Carvana commercial agreement and reducing our monthly cash burn to no greater than $12.0 million.

Through prudent deployment of capital we believe we have sufficient resources, and access to additional debt and equity capital, to adequately meet our obligations as they come due.

Cash Flows

The following table summarizes our cash flow data for the periods presented:

	Nine Months Ended September 30,
	2023		2022
	(in millions)
Net cash used in operating activities	$	(79.7)	$	(163.9)
Net cash used in investing activities	(46.2)		(5.7)
Net cash (used in) provided by financing activities	(0.9)		283.3

Net cash used in operating activities for the nine months ended September 30, 2023 was $79.7 million compared to $163.9 million of net cash used in operating activities for the nine months ended September 30, 2022. The decrease in cash used in operating activities was primarily due to a decline in net loss incurred as a result of a decrease in loss and LAE due to better loss experience and initiatives that reduced operating costs including our prior year organizational realignment and involuntary workforce reductions that reduced payroll, employee-related expenditures and facility costs. The impact of commuting certain agreements with reinsurers along with the timing of reinsurance receipts and growth in premiums not yet earned also contributed to the decrease in cash used in operating activities. This was partially offset by timing of reinsurance payments and claims payments during the nine months ended September 30, 2023 compared to the same period in 2022.

Net cash used in investing activities for the nine months ended September 30, 2023 was $46.2 million compared to $5.7 million of net cash used in investing activities for the nine months ended September 30, 2022. The increase in cash used in investing activities was primarily due to purchases of investments and fewer proceeds from sales, maturities, calls and pay downs of investments.

Net cash used in financing activities for the nine months ended September 30, 2023 was $0.9 million due to taxes paid related to net share settlement of vested restricted stock units. Net cash provided by financing activities for the nine months ended September 30, 2022 was $283.3 million primarily due to proceeds from our Term Loan.

Material Cash Requirements from Contractual and Other Obligations

There have been no material changes to our contractual and other obligations from those described in our 2022 10-K. We believe we have sufficient resources, and access to additional debt and equity capital, to adequately meet our obligations as they come due.

Off-Balance Sheet Arrangements

We do not have any off-balance sheet arrangements that have, or are reasonably likely to have, a current or future material effect on our financial condition, results of operations, liquidity or cash flows.

Critical Accounting Estimates

Our financial statements are prepared in accordance with GAAP. The preparation of the condensed consolidated financial statements in conformity with GAAP requires our management to make a number of estimates and assumptions relating to the reported amounts of assets and liabilities, the disclosure of contingent assets and liabilities at the date of the condensed consolidated financial statements and the reported amounts of revenue and expenses during the period. We evaluate our significant estimates on an ongoing basis, including, but not limited to, estimates related to reserves for loss and LAE, valuation allowance on our deferred tax assets, premium write-offs

40

and allowance for expected credit losses on premium receivables and reinsurance recoverables. We base our estimates on historical experience and on various other assumptions that we believe to be reasonable under the circumstances, the results of which form the basis for making judgments about the carrying value of assets and liabilities that are not readily apparent from other sources. Actual results could differ from those estimates.

Our critical accounting estimates are described under the heading “Management’s Discussion and Analysis of Financial Condition and Results of Operations — Critical Accounting Estimates,” in our 2022 10-K and the Notes to Condensed Consolidated Financial Statements appearing elsewhere in this Quarterly Report on Form 10-Q. During the nine months ended September 30, 2023, there were no material changes to our critical accounting estimates from those discussed in our 2022 10-K.

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Item 3.  Quantitative and Qualitative Disclosures About Market Risk

There have been no material changes in the quantitative and qualitative market risk disclosures included in the 2022 10-K.

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Item 4.  Controls and Procedures

Evaluation of Disclosure Controls and Procedures

Our management, with the participation of our principal executive officer and principal financial officer, evaluated, as of the end of the period covered by this Quarterly Report on Form 10-Q, the effectiveness of our disclosure controls and procedures (as defined in Rules 13a-15(e) and 15d-15(e) under the Exchange Act). Based on that evaluation, our principal executive officer and principal financial officer concluded that, as of September 30, 2023, our disclosure controls and procedures were not effective at the reasonable assurance level, due to the material weakness in internal control over financial reporting described below.

Previously Disclosed Material Weakness

We disclosed in Part II, Item 9A. “Controls and Procedures” in the 2022 10-K that we had identified a material weakness in internal control over financial reporting related to monitoring and the control environment, including the circumvention of control activities, that contributed to the fraud perpetrated by a former senior marketing employee, and aggregated to a material weakness. Specifically, the material weakness related to inadequate hiring practices for employees in senior leadership positions whose roles and responsibilities include the initiation of transactions with third parties, and ineffective control and monitoring activities, including the circumvention of certain control activities, related to the review, authorization and approval of third-party vendors, and associated contracts for services, and approval of third-party vendor payments.

Status of Management’s Remediation Efforts

We have taken the following steps to remediate the material weakness described above:

•Enhanced our policy to require more comprehensive hiring practices for individuals in senior leadership positions, which includes more robust background checks than we require for all employees.

•Improved the design of internal vendor management processes and controls, including having hired dedicated procurement resources to ensure contracts, including amendments, are appropriately reviewed, authorized in accordance with our delegation of authority policies, and approved.

•Clarified the design of vendor payment controls to prescribe the criteria an approver must review, in addition to invoice requests, to adequately support payments to vendors.

•Implemented more stringent monitoring controls to ensure compliance with contract reviews, approval authority limits and vendor payment policies.

While we believe progress was made to enhance and strengthen our internal control over financial reporting, the controls that were designed and implemented to address the material weakness were not in all cases in place for a sufficient period of time to demonstrate operating effectiveness. The material weakness will not be considered remediated until the applicable remedial controls operate for a sufficient period of time and management has concluded, through testing, that these controls are operating effectively.

Changes in Internal Control over Financial Reporting

Except as described above, there were no changes during the quarter ended September 30, 2023 in our internal control over financial reporting that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.

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Part II.  Other Information

Item 1.  Legal Proceedings

From time to time, we are party to litigation and legal proceedings relating to our business operations. While the outcome of all legal actions is not presently determinable, except as noted in Note 11, “Commitments and Contingencies,” in the Notes to Condensed Consolidated Financial Statements, we do not believe that we are party to any current or pending legal action that could reasonably be expected to have a material adverse effect on our financial condition or results of operations and cash flow.

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Item 1A.  Risk Factors

There have been no material changes in our risk factors from those disclosed in the 2022 10-K. In addition to the other information set forth in this Quarterly Report on Form 10-Q, you should carefully consider the risk factors discussed in Part I, Item 1A. “Risk Factors” in the 2022 10-K. You should not interpret the disclosure of any risk factor to imply the risk has not already materialized.

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Item 2.  Unregistered Sales of Equity Securities, Use of Proceeds, and Issuer Purchases of Equity Securities

Issuer Purchases of Equity Securities

None.

Dividend Policy

We have never declared or paid cash dividends on our stock. We currently intend to retain all available funds and future earnings, if any, to fund the development and expansion of our business, and we do not anticipate paying any cash dividends in the foreseeable future. Any future determination regarding the declaration and payment of dividends, if any, will be at the discretion of our board of directors and will depend on then-existing conditions, including our financial condition, operating results, contractual restrictions, capital requirements, business prospects and other factors our board of directors may deem relevant.

Dividend, Repurchase and Working Capital Restrictions

We are a holding company that transacts a majority of its business through operating subsidiaries. Our regulated insurance subsidiaries are subject to restrictions on the dividends they may pay, which could impact our ability to pay dividends to stockholders in the future.

The payment of any extraordinary dividend by one of our regulated insurance subsidiaries requires the prior approval of the superintendent of the supervisory Department of Insurance, or DOI. “Extraordinary dividend” is defined under the Ohio Revised Code, or Code, as: (i) any dividend or distribution of cash or other property whose fair market value, together with that of other dividends or distributions made within the preceding 12 months, exceeds the greater of (a) 10% of an insurer’s policyholder surplus as of December 31 of the preceding year, or (b) an insurer’s net income for the 12-month period ending December 31 of the preceding year or (ii) any dividend or distribution paid by an insurer from a source other than earned surplus. As of December 31, 2022, neither Root Insurance Company nor Root Property & Casualty Insurance Company were permitted to pay any dividends to us without approval of the superintendent of the supervisory DOI. See the section titled “Risk Factors — Risks Related to Our Business — Failure to maintain our risk-based capital at the required levels could adversely affect our ability to maintain regulatory authority to conduct our business,” included in the 2022 10-K.

In addition, insurance regulators have broad powers to prevent a reduction of statutory surplus to inadequate levels, and there is no assurance that dividends of the maximum amount calculated under any applicable formula would be permitted. The Ohio DOI may in the future adopt statutory provisions more restrictive than those currently in effect.

Further, our Term Loan includes covenants that require us to maintain certain levels of liquidity and restrict us from declaring or making cash dividend or other distributions and from repurchasing our common stock outside of the ordinary course of business or in excess of certain specified limits during the term of the applicable loan agreements.

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Item 3.  Defaults Upon Senior Securities

Not applicable.

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Item 4.  Mine Safety Disclosures

Not applicable.

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Item 5.  Other Information

None.

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Item 6.  Exhibits.

(a)Exhibits.

		Incorporation by Reference
Exhibit Number	Description of Exhibit	Form	SEC File Number	Exhibit	Filing Date	Filed Herewith
3.1	Amended and Restated Certificate of Incorporation of Root, Inc.	8-K	001-39658	3.1	October 30, 2020
3.2	Certificate of Amendment to Amended and Restated Certificate of Incorporation of Root, Inc.	8-K	001-39658	3.1	August 15, 2022
3.3	Amended and Restated Bylaws of Root, Inc.	10-K	001-39658	3.3	February 22, 2023
3.4	Certificate of Designations of Series A Preferred Stock, filed with the Delaware Secretary of State on October 1, 2021	8-K	001-39658	3.1	October 1, 2021
4.1	Form of Class A common stock certificate.	S-1/A	333-249332	4.1	October 20, 2020
4.2	Common Stock Purchase Warrants, dated as of October 1, 2021, by and between Root, Inc. and Carvana Group, LLC	8-K	001-39658	4.1	October 1, 2021
4.3	Form of Common Stock Purchase Warrant (Tranche 1), dated January 26, 2022	8-K	001-39658	4.1	January 27, 2022
4.4	Form of Common Stock Purchase Warrant (Tranche 2)	8-K	001-39658	4.2	January 27, 2022
10.1#	Executive Retention Agreement between Matt Bonakdarpour and Root, Inc., dated August 9, 2023	8-K	001-39658	10.1	August 11, 2023
10.2#	Performance-Based RSU Award Grant Notice					X
10.3#	Root, Inc. Non-Employee Director Compensation Policy adopted October 23, 2023	8-K	001-39658	10.1	October 26, 2023
31.1	Certification of Principal Executive Officer Pursuant to Rules 13a-14(a) and 15d-14(a) under the Securities Exchange Act of 1934, as Adopted Pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.					X
31.2	Certification of Principal Financial Officer Pursuant to Rules 13a-14(a) and 15d-14(a) under the Securities Exchange Act of 1934, as Adopted Pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.					X
32.1*	Certification of Principal Executive Officer and Principal Financial Officer Pursuant to 18 U.S.C. Section 1350, as Adopted Pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.					X
101.INS	Inline XBRL Instance Document
101.SCH	Inline XBRL Taxonomy Extension Schema Document
101.CAL	Inline XBRL Taxonomy Extension Calculation Linkbase Document
101.DEF	Inline XBRL Taxonomy Extension Definition Linkbase Document

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101.LAB	Inline XBRL Taxonomy Extension Label Linkbase Document
101.PRE	Inline XBRL Taxonomy Extension Presentation Linkbase Document
104	Cover Page Interactive Data File (formatted as Inline XBRL and contained in Exhibit 101).

# Indicates management contract or compensatory plan.

* The certifications furnished in Exhibit 32.1 hereto are deemed to accompany this Quarterly Report on Form 10-Q and will not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, except to the extent that the registrant specifically incorporates them by reference.

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SIGNATURES

Pursuant to the requirements of the Exchange Act of 1934, the registrant has duly caused this Quarterly Report on Form 10-Q to be signed on its behalf by the undersigned thereunto duly authorized.

	Root, Inc.
Date: November 1, 2023		By:		/s/ Alexander Timm
				Alexander Timm
				Chief Executive Officer and Director
				(Principal Executive Officer)
Date: November 1, 2023	By:		/s/ Megan Binkley
			Megan Binkley
			Chief Financial Officer
			(Principal Financial Officer and Principal Accounting Officer)

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EX-10.2

Exhibit 10.2

ROOT, INC.

PERFORMANCE-BASED RSU AWARD GRANT NOTICE

(2020 EQUITY INCENTIVE PLAN)

Root, Inc. (the “Company”) has awarded to you (the “Participant”) the number of restricted stock units specified and on the terms set forth below in consideration of your services (the “RSU Award”). Your RSU Award is subject to all of the terms and conditions as set forth herein and in the Company’s 2020 Equity Incentive Plan (the “Plan”) and the Award Agreement (the “Agreement”), which are incorporated herein in their entirety. Capitalized terms not explicitly defined herein but defined in the Plan or the Agreement shall have the meanings set forth in the Plan or the Agreement.

Participant:

Date of Grant:

Number of Restricted Stock Units:

Vesting Schedule: The Award shall vest as set forth on Exhibit A. Notwithstanding the foregoing, vesting shall terminate upon the Participant’s termination of Continuous Service.

Issuance Schedule: One share of Common Stock will be issued for each restricted stock unit which vests at the time set forth in Section 5 of the Agreement.

Participant Acknowledgments: By your signature below or by electronic acceptance or authentication in a form authorized by the Company, you understand and agree that:

•The RSU Award is governed by this RSU Award Grant Notice (the “Grant Notice”), and the provisions of the Plan and the Agreement, all of which are made a part of this document. Unless otherwise provided in the Plan, this Grant Notice and the Agreement (together, the “RSU Award Agreement”) may not be modified, amended or revised except in a writing signed by you and a duly authorized officer of the Company.

•You have read and are familiar with the provisions of the Plan, the RSU Award Agreement and the Prospectus. In the event of any conflict between the provisions in the RSU Award Agreement, or the Prospectus and the terms of the Plan, the terms of the Plan shall control.

•The RSU Award Agreement sets forth the entire understanding between you and the Company regarding the acquisition of Common Stock and supersedes all prior oral and written agreements, promises and/or representations on that subject with the exception of: (i) other equity awards previously granted to you, and (ii) any written employment agreement, offer letter, severance agreement, written severance plan or policy, or other written agreement between the Company and you in each case that specifies the terms that should govern this RSU Award.

ROOT, INC. PARTICIPANT:

By:___________________

Signature Signature

Title: Chief Executive Officer Date:

Date:

Attachments: Award Agreement

ROOT, INC.

2020 EQUITY INCENTIVE PLAN

AWARD AGREEMENT (Performance-Based RSU AWARD)

As reflected by your Restricted Stock Unit Grant Notice (“Grant Notice”), Root, Inc. (the “Company”) has granted you a RSU Award under its 2020 Equity Incentive Plan (the “Plan”) for the number of performance-based restricted stock units as indicated in your Grant Notice (the “RSU Award”). The terms of your RSU Award as specified in this Award Agreement for your RSU Award (the “Agreement”) and the Grant Notice constitute your “RSU Award Agreement”. Defined terms not explicitly defined in this Agreement but defined in the Grant Notice or the Plan shall have the same definitions as in the Grant Notice or Plan, as applicable.

The general terms applicable to your RSU Award are as follows:

1. GOVERNING PLAN DOCUMENT. Your RSU Award is subject to all the provisions of the Plan. Your RSU Award is further subject to all interpretations, amendments, rules and regulations, which may from time to time be promulgated and adopted pursuant to the Plan. In the event of any conflict between the RSU Award Agreement and the provisions of the Plan, the provisions of the Plan shall control.

2. GRANT OF THE RSU AWARD. This RSU Award represents your right to be issued on a future date the number of shares of the Company’s Common Stock that is equal to the number of restricted stock units indicated in the Grant Notice subject to your satisfaction of the vesting conditions set forth therein (the “Restricted Stock Units”). Any additional Restricted Stock Units that become subject to the RSU Award pursuant to Capitalization Adjustments as set forth in the Plan and the provisions of Section 3 below, if any, shall be subject, in a manner determined by the Board, to the same forfeiture restrictions, restrictions on transferability, and time and manner of delivery as applicable to the other Restricted Stock Units covered by your RSU Award.

3. DIVIDENDS. You shall receive no benefit or adjustment to your RSU Award with respect to any cash dividend, stock dividend or other distribution that does not result from a Capitalization Adjustment as provided in the Plan; provided, however, that this sentence shall not apply with respect to any shares of Common Stock that are delivered to you in connection with your RSU Award after such shares have been delivered to you.

4. WITHHOLDING OBLIGATIONS.

(a) Regardless of any action taken by the Company or, if different, the Affiliate to which you provide Continuous Service (the “Service Recipient”) with respect to any income tax, social insurance, payroll tax, fringe benefits tax, payment on account or other tax related items associated with the grant or vesting of the RSU Award or sale of the underlying Common Stock or other tax-related items related to your participation in the Plan and legally applicable to you (the “Tax Liability”), you hereby acknowledge and agree that the Tax Liability is your ultimate responsibility and may exceed the amount, if any, actually withheld by the Company or the Service Recipient. You further acknowledge that the Company and the Service Recipient (i) make no representations or undertakings regarding any Tax Liability in connection with any aspect of this RSU Award, including, but not limited to, the grant or vesting of the RSU Award, the issuance of Common Stock pursuant to such vesting, the subsequent sale of shares of Common Stock, and the payment of any dividends on the Common Stock; and (ii) do not commit to and are under no obligation to structure the terms of the grant or any aspect of the RSU

Award to reduce or eliminate your Tax Liability or achieve a particular tax result. Further, if you are subject to Tax Liability in more than one jurisdiction, you acknowledge that the Company and/or the Service Recipient (or former service recipient, as applicable) may be required to withhold or account for Tax Liability in more than one jurisdiction.

(b) Prior to any relevant taxable or tax withholding event, as applicable, you agree to make adequate arrangements satisfactory to the Company and/or the Service Recipient to satisfy all Tax Liability. As further provided in Section 8 of the Plan, you hereby authorize the Company and any applicable Service Recipient to satisfy any applicable withholding obligations with regard to the Tax Liability by any of the following means or by a combination of such means: (i) causing you to pay any portion of the Tax Liability in cash or cash equivalent in a form acceptable to the Company; (ii) withholding from any compensation otherwise payable to you by the Company or the Service Recipient; (iii) withholding shares of Common Stock from the shares of Common Stock issued or otherwise issuable to you in connection with the Award; provided, however, that to the extent necessary to qualify for an exemption from application of Section 16(b) of the Exchange Act, if applicable, such share withholding procedure will be subject to the express prior approval of the Board or the Company’s Compensation Committee; (iv) permitting or requiring you to enter into a “same day sale” commitment, if applicable, with a broker-dealer that is a member of the Financial Industry Regulatory Authority (a “FINRA Dealer”), pursuant to this authorization and without further consent, whereby you irrevocably elect to sell a portion of the shares of Common Stock to be delivered in connection with your Restricted Stock Units to satisfy the Tax Liability and whereby the FINRA Dealer irrevocably commits to forward the proceeds necessary to satisfy the Tax Liability directly to the Company or the Service Recipient; and/or (v) any other method determined by the Company to be in compliance with Applicable Law. Furthermore, you agree to pay the Company or the Service Recipient any amount the Company or the Service Recipient may be required to withhold, collect, or pay as a result of your participation in the Plan or that cannot be satisfied by the means previously described. In the event it is determined that the amount of the Tax Liability was greater than the amount withheld by the Company and/or the Service Recipient (as applicable), you agree to indemnify and hold the Company and/or the Service Recipient (as applicable) harmless from any failure by the Company or the applicable Service Recipient to withhold the proper amount.

(c) The Company may withhold or account for your Tax Liability by considering statutory withholding amounts or other withholding rates applicable in your jurisdiction(s), including (i) maximum applicable rates in your jurisdiction(s), in which case you may receive a refund of any over-withheld amount in cash (whether from applicable tax authorities or the Company) and you will have no entitlement to the equivalent amount in Common Stock or (ii) minimum or such other applicable rates in your jurisdiction(s), in which case you may be solely responsible for paying any additional Tax Liability to the applicable tax authorities or to the Company and/or the Service Recipient. If the Tax Liability withholding obligation is satisfied by withholding shares of Common Stock, for tax purposes, you are deemed to have been issued the full number of shares of Common Stock subject to the vested portion of the RSU Award, notwithstanding that a number of the shares of Common Stock is held back solely for the purpose of paying such Tax Liability.

(d) You acknowledge that you may not participate in the Plan and the Company shall have no obligation to deliver shares of Common Stock until you have fully satisfied the Tax Liability, as determined by the Company. Unless any withholding obligation for the Tax Liability is satisfied, the Company shall have no obligation to deliver to you any Common Stock in respect of the RSU Award.

5. DATE OF ISSUANCE.

(a) The issuance of shares in respect of the Restricted Stock Units is intended to comply with U.S. Treasury Regulations Section 1.409A-3(a) and will be construed and administered in such a manner. Subject to the satisfaction of the Tax Liability withholding obligation, if any, in the event one or more Restricted Stock Units vests, the Company shall issue to you one (1) share of Common Stock for each vested Restricted Stock Unit. Each issuance date determined by this paragraph is referred to as an “Original Issuance Date.”

(b) If the Original Issuance Date falls on a date that is not a business day, delivery shall instead occur on the next following business day. In addition, if:

(i) the Original Issuance Date does not occur (1) during an “open window period” applicable to you, as determined by the Company in accordance with the Company’s then-effective policy on trading in Company securities, or (2) on a date when you are otherwise permitted to sell shares of Common Stock on an established stock exchange or stock market (including but not limited to under a previously established written trading plan that meets the requirements of Rule 10b5-1 under the Exchange Act and was entered into in compliance with the Company’s policies (a “10b5-1 Arrangement)), and

(ii) either (1) a Tax Liability withholding obligation does not apply, or (2) the Company decides, prior to the Original Issuance Date, (A) not to satisfy the Tax Liability withholding obligation by withholding shares of Common Stock from the shares otherwise due, on the Original Issuance Date, to you under this Award, and (B) not to permit you to enter into a “same day sale” commitment with a broker-dealer (including but not limited to a commitment under a 10b5-1 Arrangement) and (C) not to permit you to pay your Tax Liability in cash, then the shares that would otherwise be issued to you on the Original Issuance Date will not be delivered on such Original Issuance Date and will instead be delivered on the first business day when you are not prohibited from selling shares of the Common Stock in the open public market, but in no event later than December 31 of the calendar year in which the Original Issuance Date occurs (that is, the last day of your taxable year in which the Original Issuance Date occurs), or, if and only if permitted in a manner that complies with U.S. Treasury Regulations Section 1.409A-1(b)(4), no later than the date that is the 15th day of the third calendar month of the applicable year following the year in which the shares of Common Stock under this Award are no longer subject to a “substantial risk of forfeiture” within the meaning of U.S. Treasury Regulations Section 1.409A-1(d).

6. TRANSFERABILITY. Except as otherwise provided in the Plan, your RSU Award is not transferable, except by will or by the applicable laws of descent and distribution.

7. CORPORATE TRANSACTION. Your RSU Award is subject to the terms of any agreement governing a Corporate Transaction involving the Company, including, without limitation, a provision for the appointment of a stockholder representative that is authorized to act on your behalf with respect to any escrow, indemnities and any contingent consideration.

8. NO LIABILITY FOR TAXES. As a condition to accepting the RSU Award, you hereby (a) agree to not make any claim against the Company, or any of its Officers, Directors, Employees or Affiliates related to tax liabilities arising from the RSU Award or other Company compensation and (b) acknowledge that you were advised to consult with your own

personal tax, financial and other legal advisors regarding the tax consequences of the RSU Award and have either done so or knowingly and voluntarily declined to do so.

9. SEVERABILITY. If any part of this Agreement or the Plan is declared by any court or governmental authority to be unlawful or invalid, such unlawfulness or invalidity will not invalidate any portion of this Agreement or the Plan not declared to be unlawful or invalid. Any Section of this Agreement (or part of such a Section) so declared to be unlawful or invalid will, if possible, be construed in a manner which will give effect to the terms of such Section or part of a Section to the fullest extent possible while remaining lawful and valid.

10. OTHER DOCUMENTS. You hereby acknowledge receipt of or the right to receive a document providing the information required by Rule 428(b)(1) promulgated under the Securities Act, which includes the Prospectus. In addition, you acknowledge receipt of the Company’s Trading Policy.

11. QUESTIONS. If you have questions regarding these or any other terms and conditions applicable to your RSU Award, including a summary of the applicable federal income tax consequences please see the Prospectus.

EXHIBIT A

VESTING SCHEDULE

The number of Restricted Stock Units that vest shall be determined in accordance with the following terms and conditions. Capitalized terms not otherwise defined herein have the meanings set forth in the Grant Notice, the Agreement or the Plan, as applicable.

1.Performance Period. The “Performance Period” shall begin on the date of grant and shall end on the April 1, 2028 (the “Scheduled Performance Period End Date”). Notwithstanding the foregoing, in the event of a Change in Control prior to the Scheduled Performance Period End Date, the Performance Period shall be shortened and deemed to end immediately prior to the effective time of the Change in Control.

2.Vesting of Restricted Stock Units. In order for Restricted Stock Units to vest, a stock-based performance requirement and vesting date requirement (the “Vesting Requirements”) must be achieved, as set forth in more detail below. A Restricted Stock Unit will vest on the first date upon which the Vesting Requirements are satisfied with respect to that particular Restricted Stock Unit. All Restricted Stock Units that do not vest on or before the end of the Scheduled Performance Period End Date shall be immediately forfeited to the Company upon expiration at no cost to the Company. In addition, all Restricted Stock Units that are unvested as of the date on which your Continuous Service terminates shall be forfeited as of the date of such termination. Except as set forth in paragraph 4 below, which shall control in the event of a Change in Control, to the extent any agreement to which participant is a party provides for accelerated vesting of equity upon the termination of a Participant's Continuous Service, then, for the avoidance of doubt, such accelerated vesting will apply to the vesting date requirement only and not the stock price requirement.

3.Vesting Requirements. Each tranche of the Restricted Stock Units (as set forth below) will meet its Vesting Requirements on the date on which the Committee certifies that the average closing price per share of Common Stock over a consecutive 45 trading day period during the Performance Period has met or exceeded the applicable stock price requirement, with such stock price requirement met on or after the applicable vesting date requirement as set forth below. Such stock price targets shall be subject to adjustment by the Board in the case of an applicable Capitalization Adjustment.

Tranche	Stock Price Requirement	Vesting Date Requirement	Number of RSUs Vesting
1
2
3
4

4.Impact of Change in Control. If, during the Performance Period, a Change in Control occurs, then the Performance Period will be shortened such that the Performance Period

will end as of immediately prior to the Change in Control and, to the extent that any of the Stock Price Requirements are achieved based on the value of the per-share consideration received by the Company’s stockholders in connection with the Change in Control (the “Per Share Consideration”) (and, for the avoidance of doubt, in lieu of and without regard to any vesting date requirement or any closing price average otherwise required to meet a Stock Price Requirement), such Stock Price Requirement will be deemed achieved.

EX-31.1

EXHIBIT 31.1

Certification of Chief Executive Officer

Pursuant to Section 302 of the Sarbanes-Oxley Act of 2002

I, Alexander Timm, certify that:

1.	I have reviewed this quarterly report on Form 10-Q of Root, Inc.;
2.	Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;
3.	Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;
4.	The registrant’s other certifying officer(s) and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting ((as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:
	(a)	Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;
	(b)	Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;
	(c)	Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and
	(d)	Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and
5.	The registrant’s other certifying officer(s) and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):
	(a)	All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and
	(b)	Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.

Date: November 1, 2023	/s/ Alexander Timm
	Alexander Timm
	Chief Executive Officer and Director
	(Principal Executive Officer)

EX-31.2

EXHIBIT 31.2

Certification of Chief Financial Officer

Pursuant to Section 302 of the Sarbanes-Oxley Act of 2002

I, Megan Binkley, certify that:

1	I have reviewed this quarterly report on Form 10-Q of Root, Inc.;
2	Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;
3	Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;
4	The registrant’s other certifying officer(s) and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting ((as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:
	(a)	Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;
	(b)	Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;
	(c)	Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and
	(d)	Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and
5	The registrant’s other certifying officer(s) and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):
	(a)	All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and
	(b)	Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.

Date: November 1, 2023	/s/ Megan Binkley
	Megan Binkley
	Chief Financial Officer
	(Principal Financial Officer)

EX-32.1

EXHIBIT 32.1

Certification of Chief Executive Officer and Chief Financial Officer
Pursuant to Section 906 of the Sarbanes-Oxley Act of 2002

Pursuant to the requirements set forth in Rule 13a-14(b) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and Section 1350 of Chapter 63 of Title 18 of the United States Code (“18 U.S.C. 1350”), Alexander Timm, Chief Executive Officer of Root, Inc. (the “Company”) and Megan Binkley, Chief Financial Officer of the Company, each hereby certifies that, to the best of his or her knowledge:

1	The Company’s Quarterly Report on Form 10-Q for the period ended September 30, 2023 to which this certification is attached as Exhibit 32.1 (the “Periodic Report”), fully complies with the requirements of Section 13(a) or Section 15(d) of the Exchange Act; and
2	The information contained in the Periodic Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

Dated: November 1, 2023

/s/ Alexander Timm

Alexander Timm

Chief Executive Officer and Director

(Principal Executive Officer)

/s/ Megan Binkley

Megan Binkley

Chief Financial Officer

(Principal Financial Officer)

This certification accompanies this Quarterly Report on Form 10-Q. The certification is not deemed filed with the Securities and Exchange Commission and is not to be incorporated by reference into any filing of Root, Inc. under the Securities Act of 1933, as amended, or the Exchange Act, whether made before or after the date of this Quarterly Report on Form 10-Q, irrespective of any general incorporation language contained in any such filing.

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COVER PAGE - shares shares in Millions	9 Months Ended
	Sep. 30, 2023	Oct. 27, 2023
Entity Listings [Line Items]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Sep. 30, 2023
Document Transition Report	false
Entity File Number	001-39658
Entity Registrant Name	ROOT, INC.
Entity Incorporation, State or Country Code	DE
Entity Tax Identification Number	84-2717903
Entity Address, Address Line One	80 E. Rich Street
Entity Address, Address Line Two	Suite 500
Entity Address, City or Town	Columbus
Entity Address, State or Province	OH
Entity Address, Postal Zip Code	43215
City Area Code	866
Local Phone Number	980-9431
Title of 12(b) Security	Class A common stock,$0.0001 par value per share
Trading Symbol	ROOT
Security Exchange Name	NASDAQ
Entity Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Accelerated Filer
Entity Small Business	true
Entity Emerging Growth Company	false
Entity Shell Company	false
Amendment Flag	false
Document Fiscal Year Focus	2023
Document Fiscal Period Focus	Q3
Entity Central Index Key	0001788882
Current Fiscal Year End Date	--12-31
Class A Shares
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		9.6
Class B Shares
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		5.0

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CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED - USD ($) $ in Millions	Sep. 30, 2023	Dec. 31, 2022
Investments:
Fixed maturities available-for-sale, at fair value (amortized cost: $171.1 and $134.2 at September 30, 2023 and December 31, 2022, respectively)	$ 164.5	$ 128.4
Short-term investments (amortized cost: $2.6 and $0.4 at September 30, 2023 and December 31, 2022, respectively)	2.6	0.4
Other investments	4.4	4.4
Total investments	171.5	133.2
Cash and cash equivalents	635.3	762.1
Restricted cash	1.0	1.0
Premiums receivable, net of allowance of $2.7 and $2.8 at September 30, 2023 and December 31, 2022, respectively	187.9	111.9
Reinsurance recoverable and receivable, net of allowance of $2.9 and $0.2 at September 30, 2023 and December 31, 2022, respectively	137.7	148.8
Prepaid reinsurance premiums	36.1	74.2
Other assets	70.7	81.7
Total assets	1,240.2	1,312.9
Liabilities:
Loss and loss adjustment expense reserves	256.5	287.4
Unearned premiums	218.9	136.5
Long-term debt and warrants	298.3	295.4
Reinsurance premiums payable	71.8	119.8
Accounts payable and accrued expenses	47.8	39.7
Other liabilities	57.8	45.0
Total liabilities	951.1	923.8
Commitments and Contingencies (Note 11)
Redeemable convertible preferred stock, $0.0001 par value, 100.0 shares authorized, 14.1 shares issued and outstanding at September 30, 2023 and December 31, 2022 (liquidation preference of $126.5)	112.0	112.0
Stockholders’ equity:
Additional paid-in capital	1,874.9	1,850.7
Accumulated other comprehensive loss	(6.6)	(5.8)
Accumulated loss	(1,691.2)	(1,567.8)
Total stockholders’ equity	177.1	277.1
Total liabilities, redeemable convertible preferred stock and stockholders’ equity	1,240.2	1,312.9
Class A Shares
Stockholders’ equity:
Common stock, value	0.0	0.0
Class B Shares
Stockholders’ equity:
Common stock, value	$ 0.0	$ 0.0

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CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED (Parenthetical) - USD ($) shares in Millions, $ in Millions	Sep. 30, 2023	Dec. 31, 2022
Amortized cost, fixed maturities	$ 171.1	$ 134.2
Amortized cost, short term investments	2.6	0.4
Allowance for premiums receivable	2.7	2.8
Allowance for credit loss	$ 2.9	$ 0.2
Preferred stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Preferred stock, shares authorized (in shares)	100.0	100.0
Preferred stock, shares issued (in shares)	14.1	14.1
Preferred stock, shares outstanding (in shares)	14.1	14.1
Preferred stock, liquidation preference	$ 126.5	$ 126.5
Class A Shares
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	1,000.0	1,000.0
Common stock, shares issued (in shares)	9.5	9.2
Common stock, shares outstanding (in shares)	9.5	9.2
Class B Shares
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	269.0	269.0
Common stock, shares issued (in shares)	5.0	5.0
Common stock, shares outstanding (in shares)	5.0	5.0

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CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS - UNAUDITED - USD ($) shares in Millions, $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Revenues:
Net premiums earned	$ 100.0	$ 68.6	$ 223.9	$ 221.6
Net investment income	9.0	0.9	22.5	2.2
Net realized gains on investments	0.0	0.0	0.0	1.1
Fee income	6.2	3.8	13.2	13.1
Other income	0.1	0.4	0.6	1.5
Total revenues	115.3	73.7	260.2	239.5
Operating expenses:
Loss and loss adjustment expenses	85.8	80.9	208.6	273.3
Sales and marketing	13.1	8.1	22.8	44.8
Other insurance expense (benefit)	18.3	1.1	22.2	(5.7)
Technology and development	11.1	14.3	32.4	46.1
General and administrative	21.0	26.4	63.2	96.4
Total operating expenses	149.3	130.8	349.2	454.9
Operating loss	(34.0)	(57.1)	(89.0)	(215.4)
Interest expense	(11.8)	(9.3)	(34.4)	(24.0)
Loss before income tax expense	(45.8)	(66.4)	(123.4)	(239.4)
Income tax expense	0.0	0.0	0.0	0.0
Net loss	(45.8)	(66.4)	(123.4)	(239.4)
Other comprehensive loss:
Changes in net unrealized losses on investments	(0.7)	(2.3)	(0.8)	(7.3)
Comprehensive loss	$ (46.5)	$ (68.7)	$ (124.2)	$ (246.7)
Loss per common share: basic (both Class A and B) (in dollars per share)	$ (3.16)	$ (4.71)	$ (8.57)	$ (17.10)
Loss per common share: diluted (both Class A and B) (in dollars per share)	$ (3.16)	$ (4.71)	$ (8.57)	$ (17.10)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)	14.5	14.1	14.4	14.0
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)	14.5	14.1	14.4	14.0

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CONDENSED CONSOLIDATED STATEMENTS OF REDEEMABLE CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS’ EQUITY - UNAUDITED - USD ($) shares in Millions, $ in Millions	Total	Class A Shares	Class B Shares	Class A and Class B Common Stock	Class A and Class B Common Stock Class A Shares	Class A and Class B Common Stock Class B Shares	Additional Paid-in Capital	Accumulated Other Comprehensive (Loss) Income	Accumulated Loss
Beginning balance (in shares) at Dec. 31, 2021	14.1
Beginning balance at Dec. 31, 2021	$ 112.0
Ending balance (in shares) at Sep. 30, 2022	14.1
Ending balance at Sep. 30, 2022	$ 112.0
Beginning balance (in shares) at Dec. 31, 2021					7.9	6.1
Beginning balance at Dec. 31, 2021	536.4			$ 0.0			$ 1,806.1	$ 0.4	$ (1,270.1)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(239.4)								(239.4)
Other comprehensive loss	(7.3)							(7.3)
Conversion of Class B to Class A (in shares)					1.1	(1.1)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)					0.1
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	0.4						0.4
Reclassification of early-exercised stock options from liabilities	0.1						0.1
Common stock—share-based compensation expense	21.8						21.8
Warrant compensation expense	10.3						10.3
Warrant issuance costs	(1.1)						(1.1)
Term Loan warrants issued	0.6						0.6
Ending balance (in shares) at Sep. 30, 2022					9.1	5.0
Ending balance at Sep. 30, 2022	$ 321.8			0.0			1,838.2	(6.9)	(1,509.5)
Beginning balance (in shares) at Jun. 30, 2022	14.1
Beginning balance at Jun. 30, 2022	$ 112.0
Ending balance (in shares) at Sep. 30, 2022	14.1
Ending balance at Sep. 30, 2022	$ 112.0
Beginning balance (in shares) at Jun. 30, 2022					8.9	5.2
Beginning balance at Jun. 30, 2022	381.3			0.0			1,829.0	(4.6)	(1,443.1)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(66.4)								(66.4)
Other comprehensive loss	(2.3)							(2.3)
Conversion of Class B to Class A (in shares)					0.2	(0.2)
Common stock—share-based compensation expense	7.8						7.8
Warrant compensation expense	1.5						1.5
Warrant issuance costs	(0.1)						(0.1)
Ending balance (in shares) at Sep. 30, 2022					9.1	5.0
Ending balance at Sep. 30, 2022	$ 321.8			0.0			1,838.2	(6.9)	(1,509.5)
Beginning balance (in shares) at Dec. 31, 2022	14.1
Beginning balance at Dec. 31, 2022	$ 112.0
Ending balance (in shares) at Sep. 30, 2023	14.1
Ending balance at Sep. 30, 2023	$ 112.0
Beginning balance (in shares) at Dec. 31, 2022		9.2	5.0		9.2	5.0
Beginning balance at Dec. 31, 2022	277.1			0.0			1,850.7	(5.8)	(1,567.8)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(123.4)								(123.4)
Other comprehensive loss	$ (0.8)							(0.8)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)	0.0				0.3
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	$ 0.0
Common stock—share-based compensation expense	12.4						12.4
Warrant compensation expense	13.3						13.3
Warrant issuance costs	(1.5)						(1.5)
Ending balance (in shares) at Sep. 30, 2023		9.5	5.0		9.5	5.0
Ending balance at Sep. 30, 2023	$ 177.1			0.0			1,874.9	(6.6)	(1,691.2)
Beginning balance (in shares) at Jun. 30, 2023	14.1
Beginning balance at Jun. 30, 2023	$ 112.0
Ending balance (in shares) at Sep. 30, 2023	14.1
Ending balance at Sep. 30, 2023	$ 112.0
Beginning balance (in shares) at Jun. 30, 2023					9.4	5.0
Beginning balance at Jun. 30, 2023	214.4			0.0			1,865.7	(5.9)	(1,645.4)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(45.8)								(45.8)
Other comprehensive loss	(0.7)							(0.7)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)					0.1
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	0.0
Common stock—share-based compensation expense	4.7						4.7
Warrant compensation expense	5.0						5.0
Warrant issuance costs	(0.5)						(0.5)
Ending balance (in shares) at Sep. 30, 2023		9.5	5.0		9.5	5.0
Ending balance at Sep. 30, 2023	$ 177.1			$ 0.0			$ 1,874.9	$ (6.6)	$ (1,691.2)

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CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - UNAUDITED - USD ($) $ in Millions	9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022
Cash flows from operating activities:
Net loss	$ (123.4)	$ (239.4)
Adjustments to reconcile net loss to net cash used in operating activities:
Share-based compensation	12.4	21.8
Warrant compensation expense	13.3	10.3
Depreciation and amortization	8.2	9.5
Bad debt expense	10.6	13.7
Net realized gains on investments	0.0	(1.1)
Gain on lease modification	(0.3)	(0.2)
Changes in operating assets and liabilities:
Premiums receivable	(83.9)	4.5
Reinsurance recoverable and receivable	8.5	19.0
Prepaid reinsurance premiums	38.1	14.6
Other assets	10.6	(2.0)
Losses and loss adjustment expenses reserves	(30.9)	(26.0)
Unearned premiums	82.4	(22.8)
Reinsurance premiums payable	(48.0)	8.8
Accounts payable and accrued expenses	9.6	17.5
Other liabilities	13.1	7.9
Net cash used in operating activities	(79.7)	(163.9)
Cash flows from investing activities:
Purchases of investments	(61.7)	(30.8)
Proceeds from maturities, call and pay downs of investments	22.3	26.7
Sales of investments	0.5	7.1
Capitalization of internally developed software	(7.1)	(7.4)
Purchases of fixed assets	(0.2)	0.0
Purchases of indefinite-lived intangible assets and transaction costs	0.0	(1.3)
Net cash used in investing activities	(46.2)	(5.7)
Cash flows from financing activities:
Proceeds from exercise of stock options and restricted stock units, net of tax (withholding)/proceeds	(0.9)
Proceeds from exercise of stock options and restricted stock units, net of tax (withholding)/proceeds		0.3
Proceeds from issuance of debt and related warrants, net of issuance costs	0.0	286.0
Payment of preferred stock and related warrants issuance costs	0.0	(3.0)
Net cash (used in) provided by financing activities	(0.9)	283.3
Net (decrease) increase in cash, cash equivalents and restricted cash	(126.8)	113.7
Cash, cash equivalents and restricted cash at beginning of period	763.1	707.0
Cash, cash equivalents and restricted cash at end of period	$ 636.3	$ 820.7

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NATURE OF BUSINESS	9 Months Ended
	Sep. 30, 2023
Organization, Consolidation and Presentation of Financial Statements [Abstract]
NATURE OF BUSINESS	NATURE OF BUSINESSRoot, Inc. is a holding company which, directly or indirectly, maintains 100% ownership of each of its subsidiaries, including, among others, Root Insurance Company and Root Property & Casualty Insurance Company, both Ohio-domiciled insurance companies, and Root Reinsurance Company, Ltd., a Cayman Islands-domiciled reinsurance company, together with Root, Inc., “we,” “us” or “our.” We were formed in 2015 and began writing personal auto insurance in July 2016. We are a technology company operating primarily a direct-to-consumer model with the majority of our personal insurance customers acquired through mobile applications and our embedded platform. We offer auto and renters insurance products underwritten by Root Insurance Company and Root Property & Casualty Insurance Company.

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BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

9 Months Ended

Sep. 30, 2023

Accounting Policies [Abstract]

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

Basis of Presentation—In our opinion, all adjustments necessary for a fair presentation of the condensed consolidated financial statements have been included. All such adjustments are of a normal and recurring nature. These condensed consolidated financial statements are unaudited and, accordingly, should be read in conjunction with the consolidated financial statements and related notes included in the Annual Report on Form 10-K for the year ended December 31, 2022 filed with the Securities and Exchange Commission, or SEC, on February 22, 2023.

Basis of Consolidation—The unaudited condensed consolidated financial statements include the accounts of Root, Inc. and its subsidiaries, all of which are wholly owned. These financial statements have been prepared in accordance with accounting principles generally accepted in the United States, or GAAP. All intercompany accounts and transactions have been eliminated.

Use of Estimates—The preparation of the unaudited condensed consolidated financial statements requires management to make certain estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the unaudited condensed consolidated financial statements and the reported amounts of revenue and expenses during the reporting period. Actual results could differ from those estimates. Significant estimates reflected in our unaudited condensed consolidated financial statements include, but are not limited to, reserves for loss and loss adjustment expense, or LAE, valuation allowances for income taxes and allowance for expected credit losses on premium receivables and reinsurance recoverables.

Revision of Previously Issued Financial Statements—During the fourth quarter of 2022, we identified errors in our first, second and third quarter financial statements for 2022 and revised the quarterly presentation of certain sales and marketing and general and administrative expenses on our condensed consolidated statements of operations and comprehensive loss related to the purported misappropriation of funds by a senior marketing employee. The errors did not impact periods prior to 2022.

In accordance with SEC Staff Accounting Bulletin, or SAB, No. 99, Materiality, and SAB No. 108, Considering the Effects of Prior Year Misstatements when Quantifying Misstatements in Current Year Financial Statements, we assessed the materiality of these errors on our financial statements and concluded the errors were not material to the unaudited interim financial statements for the three and nine months ended September 30, 2022.

The following tables present the effect of the revision on the condensed consolidated statements of operations and comprehensive loss for the three and nine months ended September 30, 2022, condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity and condensed consolidated statement of cash flows as of and for the nine months ended September 30, 2022.

	Three Months Ended September 30, 2022 (unaudited)						Nine Months Ended September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected		As reported		Adjustments		As Corrected
	(in millions, except per share amounts)
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing	$	5.7	$	2.4	$	8.1	$	45.8	$	(1.0)	$	44.8
General and administrative	26.4		—		26.4		86.3		10.1		96.4
Total operating expenses	128.4		2.4		130.8		445.8		9.1		454.9
Operating loss	(54.7)		(2.4)		(57.1)		(206.3)		(9.1)		(215.4)
Loss before income tax expense	(64.0)		(2.4)		(66.4)		(230.3)		(9.1)		(239.4)
Net loss	(64.0)		(2.4)		(66.4)		(230.3)		(9.1)		(239.4)
Comprehensive loss	$	(66.3)	$	(2.4)	$	(68.7)	$	(237.6)	$	(9.1)	$	(246.7)
Weighted-average common shares outstanding: basic and diluted (both Class A and B)	14.1				14.1		14.0				14.0
Loss per common share: basic and diluted (both Class A and B)	$	(4.54)			$	(4.71)	$	(16.45)			$	(17.10)

	As of September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected
	(in millions)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Accumulated loss	$	(1,500.4)	$	(9.1)	$	(1,509.5)
Total stockholders’ equity	$	330.9	$	(9.1)	$	321.8

	Nine Months Ended September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected
	(in millions)
Condensed consolidated statement of cash flows:
Net loss	$	(230.3)	$	(9.1)	$	(239.4)
Other assets	(11.1)		9.1		(2.0)
Net cash used in operating activities	$	(163.9)	$	—	$	(163.9)

Cash, Cash Equivalents and Restricted Cash—The following table provides a reconciliation of cash, cash equivalents and restricted cash reported within the condensed consolidated balance sheets that sum to the total of the same such amount in the condensed consolidated statements of cash flows:

	As of
	September 30,		December 31,
	2023		2022
	(dollars in millions)
Cash and cash equivalents	$	635.3	$	762.1
Restricted cash	1.0		1.0
Total cash, cash equivalents and restricted cash shown in the condensed consolidated statements of cash flows	$	636.3	$	763.1

Performance-Based Restricted Stock Units—During the third quarter of 2023, we granted 0.4 million performance-based restricted stock units, or PSUs, to certain key employees as part of our equity compensation plan. The PSUs are expected to vest over a derived service period of one to four-years and are dependent upon the fulfillment of both a service condition and the achievement of stock-price goals during the performance period, with the latter being classified as a market condition according to Accounting Standard Codification 718, Stock Compensation. The service condition with respect to the four tranches of PSUs will be met in installments on April 1, 2024, and each of the subsequent three anniversaries of that date, or Vesting Date Requirement, subject to the individual’s continued service through such dates. Stock price goals must be met on or after the respective tranche’s Vesting Date Requirement and are based on the average closing price per share of our Class A common stock over a consecutive 45 day trading period. Any tranche of PSUs with respect to which the stock price goal has not been met as of April 1, 2028 (the final day of the performance period) will be forfeited as of such date.

The PSU compensation expense is recognized based on the grant date fair value of the award, which was determined by simulating Root’s stock prices using a Monte Carlo simulation in a risk-neutral framework, assuming a Geometric Brownian Motion. The simulation is repeated 100,000 times, and the average of the discounted values for each tranche is the grant date fair value for that tranche. The median time to vest is the derived service period.

Employing a Monte Carlo simulation requires a range of inputs for each uncertain variable, and establishing linkage between the assumptions, if necessary. Inputs and assumptions used in our analysis included our stock price at grant date, exercise prices, the term of the PSUs, equity volatility, risk-free rate and dividend yield. Equity volatility was derived using a blended volatility assumption of 50% weight on Root’s historical volatility calculated from daily stock returns since IPO from the grant date and a 50% weight based on Root’s term matched simple average peer volatility as of the valuation date because our company-specific volatility is not sufficient by itself at the time of grant.

The expense is recognized via a graded vesting method over the derived service period. In the event that both the service condition and market condition are met earlier, expense would be accelerated. If the service condition is not achieved, previously recognized compensation cost for the associated tranche is reversed. In the event that the market conditions are never achieved before the expiration date, but the service condition is met, the respective compensation costs remain recognized.

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INVESTMENTS

9 Months Ended

Sep. 30, 2023

Investments, Debt and Equity Securities [Abstract]

INVESTMENTS

INVESTMENTS

The amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities at September 30, 2023 and December 31, 2022 are as follows:

	September 30, 2023
	Amortized Cost		Allowance for Expected Credit Losses		Gross Unrealized Gains		Gross Unrealized Losses		Fair Value
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	16.8	$	—	$	—	$	(0.4)	$	16.4
Municipal securities	25.6		—		—		(1.3)		24.3
Corporate debt securities	69.4		—		—		(2.9)		66.5
Residential mortgage-backed securities	12.3		—		—		(0.5)		11.8
Commercial mortgage-backed securities	31.0		—		—		(1.3)		29.7
Other debt obligations	16.0		—		—		(0.2)		15.8
Total fixed maturities	171.1		—		—		(6.6)		164.5
Short-term investments	2.6		—		—		—		2.6
Total	$	173.7	$	—	$	—	$	(6.6)	$	167.1
	December 31, 2022
	Amortized Cost		Allowance for Expected Credit Losses		Gross Unrealized Gains		Gross Unrealized Losses		Fair Value
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	11.3	$	—	$	—	$	(0.3)	$	11.0
Municipal securities	21.4		—		—		(1.2)		20.2
Corporate debt securities	60.5		—		—		(2.7)		57.8
Residential mortgage-backed securities	5.5		—		—		(0.3)		5.2
Commercial mortgage-backed securities	24.4		—		—		(1.2)		23.2
Other debt obligations	11.1		—		0.1		(0.2)		11.0
Total fixed maturities	134.2		—		0.1		(5.9)		128.4
Short-term investments	0.4		—		—		—		0.4
Total	$	134.6	$	—	$	0.1	$	(5.9)	$	128.8

Management reviewed the available-for-sale securities at each balance sheet date to consider whether it was necessary to recognize a credit loss as of September 30, 2023 and December 31, 2022. We do not intend to sell the investments and it is not more likely than not that we will be required to sell the security before recovery. Management concluded that the available-for-sale securities’ unrealized losses were due to non-credit related factors and, therefore, there was no allowance for credit loss as of September 30, 2023 and December 31, 2022.

The following tables reflect the gross unrealized losses and fair value of short-term investments and available-for-sale fixed maturity securities, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at September 30, 2023 and December 31, 2022:

	September 30, 2023
	Less than 12 Months				12 Months or More				Total
	Fair Value		Unrealized Loss		Fair Value		Unrealized Loss		Fair Value		Unrealized Loss
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	10.2	$	(0.2)	$	6.2	$	(0.2)	$	16.4	$	(0.4)
Municipal securities	7.9		(0.2)		15.7		(1.1)		23.6		(1.3)
Corporate debt securities	27.1		(0.8)		39.3		(2.1)		66.4		(2.9)
Residential mortgage-backed securities	8.5		(0.2)		2.7		(0.3)		11.2		(0.5)
Commercial mortgage-backed securities	13.5		(0.4)		15.8		(0.9)		29.3		(1.3)
Other debt obligations	9.5		(0.1)		3.8		(0.1)		13.3		(0.2)
Total fixed maturities	76.7		(1.9)		83.5		(4.7)		160.2		(6.6)
Short-term investments	1.1		—		—		—		1.1		—
Total	$	77.8	$	(1.9)	$	83.5	$	(4.7)	$	161.3	$	(6.6)
	December 31, 2022
	Less than 12 Months				12 Months or More				Total
	Fair Value		Unrealized Loss		Fair Value		Unrealized Loss		Fair Value		Unrealized Loss
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	6.9	$	(0.1)	$	4.1	$	(0.2)	$	11.0	$	(0.3)
Municipal securities	11.5		(0.5)		8.2		(0.7)		19.7		(1.2)
Corporate debt securities	45.3		(1.6)		11.5		(1.1)		56.8		(2.7)
Residential mortgage-backed securities	2.2		—		1.9		(0.3)		4.1		(0.3)
Commercial mortgage-backed securities	18.3		(0.8)		4.6		(0.4)		22.9		(1.2)
Other debt obligations	6.8		(0.2)		—		—		6.8		(0.2)
Total fixed maturities	91.0		(3.2)		30.3		(2.7)		121.3		(5.9)
Short-term investments	0.1		—		—		—		0.1		—
Total	$	91.1	$	(3.2)	$	30.3	$	(2.7)	$	121.4	$	(5.9)

Other Investments

As of September 30, 2023 and December 31, 2022, other investments related to our private equity investments were $4.4 million. There were no realized gains or losses for the three and nine months ended September 30, 2023. We recognized zero and $1.2 million of realized gains for the three and nine months ended September 30, 2022, respectively. We recorded the gain on sale of our private equity investments within net realized gains on investments in our condensed consolidated statements of operations and comprehensive loss. There were no unrealized gains and losses or impairment losses recognized on private equity investments for the three and nine months ended September 30, 2023 and 2022.

The following table reflects the gross and net realized gains and losses on short-term investments, available-for-sale fixed maturities and other investments that have been included in the condensed consolidated statements of operations and comprehensive loss for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Realized gains on investments	$	—	$	—	$	—	$	1.2
Realized losses on investments	—		—		—		(0.1)
Net realized gains on investments	$	—	$	—	$	—	$	1.1

The following table sets forth the amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities by contractual maturity at September 30, 2023:

	September 30, 2023
	Amortized Cost		Fair Value
	(dollars in millions)
Due in one year or less	$	33.3	$	32.8
Due after one year through five years	102.3		98.1
Due five years through 10 years	21.4		20.4
Due after 10 years	16.7		15.8
Total	$	173.7	$	167.1

The following table sets forth the components of net investment income for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Interest on bonds	$	1.4	$	0.6	$	3.3	$	1.7
Interest on deposits and cash equivalents	7.9		0.6		19.8		1.2
Total	9.3		1.2		23.1		2.9
Investment expense	(0.3)		(0.3)		(0.6)		(0.7)
Net investment income	$	9.0	$	0.9	$	22.5	$	2.2

The following tables summarize the credit ratings of short-term investments and available-for-sale fixed maturity securities at September 30, 2023 and December 31, 2022:

	September 30, 2023
	Amortized Cost		Fair Value		% of Total Fair Value
	(dollars in millions)
S&P Global rating or equivalent
AAA	$	51.2	$	49.3	29.5	%
AA+, AA, AA-, A-1	62.4		60.2		36.0
A+, A, A-	46.3		44.2		26.5
BBB+, BBB, BBB-	13.8		13.4		8.0
Total	$	173.7	$	167.1	100.0	%

	December 31, 2022
	Amortized Cost		Fair Value		% of Total Fair Value
	(dollars in millions)
S&P Global rating or equivalent
AAA	$	62.5	$	59.9	46.5	%
AA+, AA, AA-, A-1	19.9		19.1		14.8
A+, A, A-	38.4		36.5		28.3
BBB+, BBB, BBB-	13.8		13.3		10.4
Total	$	134.6	$	128.8	100.0	%

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FAIR VALUE OF FINANCIAL INSTRUMENTS

9 Months Ended

Sep. 30, 2023

Fair Value Disclosures [Abstract]

FAIR VALUE OF FINANCIAL INSTRUMENTS

FAIR VALUE OF FINANCIAL INSTRUMENTS

The following tables provide information about our financial assets measured and reported at fair value as of September 30, 2023 and December 31, 2022:

	September 30, 2023
	Level 1		Level 2		Level 3		Total Fair Value
	(dollars in millions)
Assets
Fixed maturities:
U.S. Treasury securities and agencies	$	15.4	$	1.0	$	—	$	16.4
Municipal securities	—		24.3		—		24.3
Corporate debt securities	—		66.5		—		66.5
Residential mortgage-backed securities	—		11.8		—		11.8
Commercial mortgage-backed securities	—		29.7		—		29.7
Other debt obligations	—		15.8		—		15.8
Total fixed maturities	15.4		149.1		—		164.5
Short-term investments	2.4		0.2		—		2.6
Cash equivalents	363.6		—		—		363.6
Total assets at fair value	$	381.4	$	149.3	$	—	$	530.7
	December 31, 2022
	Level 1		Level 2		Level 3		Total Fair Value
	(dollars in millions)
Assets
Fixed maturities:
U.S. Treasury securities and agencies	$	9.2	$	1.8	$	—	$	11.0
Municipal securities	—		20.2		—		20.2
Corporate debt securities	—		57.8		—		57.8
Residential mortgage-backed securities	—		5.2		—		5.2
Commercial mortgage-backed securities	—		23.2		—		23.2
Other debt obligations	—		11.0		—		11.0
Total fixed maturities	9.2		119.2		—		128.4
Short-term investments	—		0.4		—		0.4
Cash equivalents	487.3		—		—		487.3
Total assets at fair value	$	496.5	$	119.6	$	—	$	616.1

We estimate the fair value of all our different classes of Level 2 fixed maturities and short-term investments by using quoted prices from a combination of an independent pricing vendor or broker/dealer, pricing models, quoted prices of securities with similar characteristics or discounted cash flows. All significant inputs were observable in the active markets.

Private Equity Investments Measured at Fair Value on a Non-Recurring Basis

Private equity investments that have been remeasured during the period due to an observable event or impairment are classified within Level 3 in the fair value hierarchy because we estimate the value based on valuation methods which may include a combination of the observable transaction price at the transaction date and other

unobservable inputs including volatility, rights, and obligations of the investments we hold. See Note 3, “Investments,” for further information on our private equity investments.

Fair Value of Long-Term Debt

The carrying amount of long-term debt is recorded at the unpaid balance, net of discount and debt issuance costs. The fair value of outstanding long-term debt is classified within Level 2 of the fair value hierarchy. The fair value is based on a model referencing observable interest rates and spreads to project and discount cash flows to present value. As of September 30, 2023 and December 31, 2022, the carrying amounts and fair values of these financial instruments were as follows:

	Carrying Amount as of September 30, 2023		Estimated Fair Value as of September 30, 2023		Carrying Amount as of December 31, 2022		Estimated Fair Value as of December 31, 2022
	(dollars in millions)
Long-term debt	$	298.3	$	304.8	$	295.4	$	309.7

The carrying amounts of other short-term financial instruments approximates their fair value due to their short-term nature.

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LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES

9 Months Ended

Sep. 30, 2023

Insurance [Abstract]

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES

The following provides a reconciliation of the beginning and ending reserve balances for loss and LAE, net of reinsurance:

	Nine Months Ended September 30,
	2023		2022
	(dollars in millions)
Gross loss and LAE reserves, January 1	$	287.4	$	320.2
Reinsurance recoverable on unpaid losses	(76.4)		(79.5)
Net loss and LAE reserves, January 1	211.0		240.7
Net incurred loss and LAE related to:
Current year	209.2		273.5
Prior years	(0.6)		(0.2)
Total incurred	208.6		273.3
Net paid loss and LAE related to:
Current year	87.4		155.5
Prior years	117.3		135.6
Total paid	204.7		291.1
Net loss and LAE reserves, September 30	214.9		222.9
Plus reinsurance recoverable on unpaid losses	41.6		71.3
Gross loss and LAE reserves, September 30	$	256.5	$	294.2

Incurred losses and LAE attributable to prior accident years was a decrease of $0.6 million and $0.2 million for the nine months ended September 30, 2023 and 2022, respectively. For the nine months ended September 30, 2023, the development of incurred losses and LAE related to prior periods was a result of lower-than-expected reported losses on injury coverages, partially offset by losses on commutations of certain reinsurance agreements and higher-than-expected LAE on prior accident periods. For the nine months ended September 30, 2022, the development of incurred losses and LAE related to prior periods was a result of lower-than-expected LAE on prior accident period claims, partially offset by higher-than-expected reported losses on property damage and collision claims due to inflation.

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REINSURANCE

9 Months Ended

Sep. 30, 2023

Insurance [Abstract]

REINSURANCE

REINSURANCE

The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Premiums written:
Direct	$	192.7	$	139.6	$	444.6	$	443.9
Assumed	31.5		11.1		59.3		34.1
Ceded	(22.3)		(81.0)		(159.4)		(264.5)
Net premiums written	$	201.9	$	69.7	$	344.5	$	213.5
Premiums earned:
Direct	$	141.6	$	144.5	$	381.9	$	469.3
Assumed	18.2		10.8		39.5		31.5
Ceded	(59.8)		(86.7)		(197.5)		(279.2)
Net premiums earned	$	100.0	$	68.6	$	223.9	$	221.6
Losses and LAE incurred:
Direct	$	106.8	$	126.1	$	297.1	$	430.0
Assumed	13.4		11.3		29.8		35.7
Ceded	(34.4)		(56.5)		(118.3)		(192.4)
Net losses and LAE incurred	$	85.8	$	80.9	$	208.6	$	273.3

During the third quarter of 2023, we commuted certain agreements with our reinsurers which resulted in $4.4 million of net premiums earned, $4.2 million of loss and loss adjustment expenses and $5.8 million of other insurance expense (benefit), respectively, on the condensed consolidated statements of operations and comprehensive loss. A portion of the loss and loss adjustment expenses is related to an allowance for credit losses of $2.8 million, that was established due to a commutation with one of our reinsurers as of September 30, 2023.

Additionally, in connection with the commutation of certain agreements with reinsurers during the third quarter of 2023, we received cash and cash equivalents of $3.9 million, reinsurance recoverable and receivable decreased by $6.1 million, prepaid reinsurance premiums was reduced by $33.5 million and reinsurance premiums payable decreased by $30.2 million all of which are reported within the condensed consolidated balance sheets.

In the event that all or any of the reinsuring companies might be unable to meet their obligations under existing reinsurance agreements, we would be liable to the policyholder for such defaulted amounts.

GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN

Gross premiums written by state is as follows for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,								Nine Months Ended September 30,
	2023				2022				2023				2022
	Amount		% of Total		Amount		% of Total		Amount		% of Total		Amount		% of Total
	(dollars in millions)
State:
Texas	$	36.8	16.4	%	$	26.2	17.4	%	$	80.1	15.9	%	$	89.5	18.7	%
Georgia	26.3		11.7		15.0		10.0		56.0		11.1		48.8		10.2
Colorado	15.3		6.8		10.3		6.8		37.8		7.5		30.8		6.4
Pennsylvania	12.1		5.4		9.1		6.0		29.0		5.8		26.8		5.6
South Carolina	11.8		5.3		4.5		3.0		28.6		5.7		16.4		3.4
Utah	8.3		3.7		8.0		5.3		22.9		4.5		24.1		5.0
Arizona	11.0		4.9		4.3		2.9		21.7		4.3		13.3		2.8
Ohio	8.4		3.7		3.9		2.6		16.9		3.4		11.8		2.5
Oklahoma	7.2		3.2		5.2		3.5		16.7		3.3		16.1		3.4
Missouri	8.7		3.9		4.3		2.9		16.1		3.2		14.2		3.0
All others states	78.3		35.0		59.9		39.6		178.1		35.3		186.2		39.0
Total	$	224.2	100.0	%	$	150.7	100.0	%	$	503.9	100.0	%	$	478.0	100.0	%

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LONG-TERM DEBT

9 Months Ended

Sep. 30, 2023

Debt Disclosure [Abstract]

LONG-TERM DEBT

LONG-TERM DEBTIn January 2022, we entered into a $300.0 million five-year term loan, or Term Loan, with the principal amount due and payable upon maturity on January 27, 2027. Interest is payable quarterly and is determined on a floating interest rate currently calculated on the Secured Overnight Financing Rate, or SOFR, with a 1.0% floor, plus 9.0%.

The following summarizes the carrying value of long-term debt as of September 30, 2023 and December 31, 2022:

	September 30, 2023		December 31, 2022
	(dollars in millions)
Term Loan	$	300.0	$	300.0
Accrued interest payable	7.9		7.3
Unamortized discount, debt issuance costs and warrants	(9.6)		(11.9)
Total	$	298.3	$	295.4

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INCOME TAXES

9 Months Ended

Sep. 30, 2023

Income Tax Disclosure [Abstract]

INCOME TAXES

INCOME TAXES

The consolidated effective tax rate was zero for the three and nine months ended September 30, 2023 and 2022. The difference between these rates and the U.S. federal income tax rate of 21% was primarily due to a full valuation allowance on our U.S. deferred tax assets.

As of September 30, 2023 and December 31, 2022, we did not have any unrecognized tax benefits for uncertain tax positions and had no interest or penalties related to uncertain tax positions.

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RESTRUCTURING COSTS

9 Months Ended

Sep. 30, 2023

Restructuring and Related Activities [Abstract]

RESTRUCTURING COSTS

RESTRUCTURING COSTS

In 2022, we conducted strategic initiatives to reduce operating costs, improve efficiency, and increase focus on our strategic priorities. These initiatives resulted in restructuring actions that included a reduction in workforce levels, contract terminations, and in certain instances, a reduction in office space. These restructuring actions include the following costs:

Employee costs—consist of severance, benefits, share-based compensation, and employee compensation expense dependent upon continuous employment for certain employees and related employee costs.

Real estate exit costs—consist of real estate exit costs primarily related to accelerated amortization of right-of-use assets, leasehold improvements and furniture and fixtures.

Other costs—primarily consist of contract termination costs incurred as part of our efforts to improve efficiency and reduce operating costs and accelerated expense for software that no longer has economic benefit.

As of September 30, 2023, we expect to incur approximately $1.7 million of employee compensation expense, dependent upon continuous employment for certain employees, to be recognized ratably through the fourth quarter of 2023. We expect a cash expenditure related to these employee compensation costs in January 2024. As of September 30, 2023, except as discussed above, we do not expect to incur any additional material expenditures in future periods related to restructuring actions that have occurred.

The following table displays restructuring costs recorded in general and administrative expenses on the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,				Cumulative Incurred Through September 30, 2023
	2023		2022		2023		2022
	(dollars in millions)
Restructuring costs:
Employee costs	$	1.8	$	—	$	5.9	$	5.6	$	21.4
Real estate exit costs	—		—		—		2.1		2.1
Other costs	0.1		—		3.5		0.7		4.5
Total restructuring costs	$	1.9	$	—	$	9.4	$	8.4	$	28.0

The following table displays a rollforward of the accrual for restructuring costs recorded in other liabilities on the condensed consolidated balance sheets:

	Employee costs		Other costs		Total liability
	(dollars in millions)
Restructuring activity:
Restructuring liability as of January 1, 2023	$	3.1	$	0.1	$	3.2
Expense incurred	5.5		3.4		8.9
Payments	(2.0)		(3.5)		(5.5)
Restructuring liability as of September 30, 2023	$	6.6	$	—	$	6.6

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SHARE-BASED COMPENSATION

9 Months Ended

Sep. 30, 2023

Share-Based Payment Arrangement [Abstract]

SHARE-BASED COMPENSATION

SHARE-BASED COMPENSATION

Warrants

In October 2021, we issued Carvana eight tranches of warrants, comprised of three tranches of “short-term warrants” and five tranches of “long-term warrants,” with the opportunity to purchase a maximum of 7.2 million shares of Class A common stock. As of September 30, 2023, we determined the remaining unvested short-term warrants were probable of vesting. Under that scenario, it is not a possible outcome for the long-term warrants to also vest, so they are considered not probable of vesting. We recognized warrant compensation expense related to these equity-classified warrants based on progress toward completing the integrated automobile insurance solution for Carvana’s online buying platform, or the Integrated Platform, and policies originating through the Integrated Platform. All of these warrants are out-of-the-money and therefore have no intrinsic value as of September 30, 2023.

The following table displays warrant compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Warrant compensation expense:
Sales and marketing	$	—	$	—	$	—	$	8.8
Other insurance expense (benefit)	5.0		1.5		13.3		1.5
Total warrant compensation expense	$	5.0	$	1.5	$	13.3	$	10.3

As of September 30, 2023, there was $7.8 million of unrecognized compensation cost related to warrants. The remaining costs are expected to be recognized over a period of approximately one year.

Employee Share-Based Compensation

We maintain an equity incentive plan, or the Plan, for the issuance and grant of equity awards (restricted stock, restricted stock units, or RSUs, PSUs, and incentive and nonqualified stock options) to our officers, directors, employees and certain advisors. As of September 30, 2023, we had 1.2 million common shares available for issuance under the Plan.

The following table displays share-based compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Share-based compensation expense:
Loss and loss adjustment expenses	$	0.2	$	0.2	$	0.5	$	0.6
Sales and marketing	0.1		0.3		0.3		0.7
Other insurance expense (benefit)	0.1		0.3		0.4		0.8
Technology and development	0.9		1.1		2.4		3.1
General and administrative	3.4		5.9		8.8		16.6
Total share-based compensation expense	$	4.7	$	7.8	$	12.4	$	21.8

The following table provides total share-based compensation expense by type of award:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Share-based compensation expense:
Restricted stock unit expense	$	4.4	$	7.4	$	11.4	$	20.5
Performance-based restricted stock unit expense	0.1		—		0.1		—
Stock option expense	0.2		0.4		0.9		1.3
Total share-based compensation expense	$	4.7	$	7.8	$	12.4	$	21.8

As of September 30, 2023, there was $1.2 million, $25.3 million, and $2.2 million of unrecognized compensation cost related to unvested stock options, RSUs, and PSUs, respectively. The remaining costs are expected to be recognized over a period of approximately three years for unvested stock options and four years for RSUs and PSUs.

Performance-Based Restricted Stock Units

The fair value of the PSUs is estimated on the date of grant using a Monte Carlo simulation with Geometric Brownian Motion that uses certain inputs, assumptions and estimates, as follows: expected term of approximately five years, based on the contractual term of the PSUs; risk-free interest rate of 4.06%, based on U.S. Constant Maturity Yield Curve over a similar term; dividend rate of 0.0%, based on our historical and expected future dividend payouts; and volatility of 76%, and other factors.

The following table provides other key terms of the PSUs:

Performance-Based Restricted Stock Units	Stock Price Goals		Shares Issued	Grant Date Fair Value per Share
	(in millions, except per share amounts)
Tranches:
Tranche 1	$	16.76	—	$	7.69
Tranche 2	25.14		0.1	6.70
Tranche 3	33.52		0.1	5.87
Tranche 4	$	41.90	0.2	$	5.10
			0.4

Restricted Stock Units and Performance-Based Restricted Stock Units

A summary of RSU and PSU activity for the nine months ended September 30, 2023 is as follows:

	Nine Months Ended September 30, 2023
Restricted Stock Units and Performance-Based Restricted Stock Units	Number of Shares	Weighted-Average Grant Date Fair Value per Share		Aggregate Intrinsic Value
	(in millions, except per share amounts)
Nonvested at January 1, 2023	1.1	$	51.81	$	5.0
Granted	1.6	6.62
Vested	(0.5)	50.44		2.8
Forfeited, expired or canceled	(0.2)	53.75
Nonvested at September 30, 2023	2.0	$	15.79	$	18.9

Stock Options

A summary of option activity for the nine months ended September 30, 2023 is as follows:

	Nine Months Ended September 30, 2023
Options	Number of Shares	Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Term (in Years)	Aggregate Intrinsic Value
	(in millions, except exercise price and term amounts)
Outstanding and exercisable at January 1, 2023	0.2	$	38.15	5.63	$	0.2
Granted	—	8.94
Exercised	—	—			—
Forfeited, expired or canceled	(0.1)	44.86
Outstanding and exercisable at September 30, 2023	0.1	$	33.74	4.53	$	0.5

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COMMITMENTS AND CONTINGENCIES

9 Months Ended

Sep. 30, 2023

Commitments and Contingencies Disclosure [Abstract]

COMMITMENTS AND CONTINGENCIES

COMMITMENTS AND CONTINGENCIES

From time to time, we are party to litigation and legal proceedings relating to our business operations. Except as disclosed below, we do not believe that we are party to any current or pending legal action that could reasonably be expected to have a material adverse effect on our financial condition or results of operations and cash flow.

On December 19, 2022, a purported class action complaint was filed against the Company’s subsidiary, Root Insurance Company, in the U.S. District Court for the Western District of Texas (Case No. 1:22-cv-01328-LY) by an individual on her behalf and further claiming to represent a putative class of insureds. The complaint alleges that Root Insurance Company breached its insurance contract and violated specific provisions of the Texas Prompt Payment of Claims Act for an alleged failure to include sales tax in total loss vehicle settlements. The complaint seeks damages to include payment of alleged benefits owed under the policy, in addition to pre- and post-judgment interest and attorneys fees on behalf of the named plaintiff and the putative class members. Root Insurance Company’s motion to dismiss the claims set forth in the complaint was granted and the lawsuit was dismissed with prejudice on August 22, 2023, which dismissal has been appealed. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is in its early stages. Therefore, at this time, we cannot predict the outcome or estimate the likelihood or magnitude of our possible or potential loss contingency.

On June 27, 2022, a verified shareholder derivative complaint was filed against certain of the Company’s current and former officers and directors in the U.S. District Court for the District of Delaware (Case No. 1:22-

cv-00865). The Company was named as a nominal defendant. The complaint alleges that defendants made false or misleading statements and omissions of purportedly material fact, in violation of Section 10(b) of the Securities Exchange Act of 1934, or the Exchange Act, and Rule 10b-5 thereunder, breached their fiduciary duties and/or aided and abetted the breach of fiduciary duties, were unjustly enriched, wasted corporate assets, and are liable under Section 11(f) of the Securities Act of 1933, or the Securities Act, in connection with and following the Company’s initial public offering. The complaint seeks unspecified damages. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is currently stayed pending final resolution of the below matter and, at this time, we cannot predict the outcome or estimate the likelihood or magnitude of our possible or potential loss contingency.

On March 19, 2021, a purported class action complaint was filed against the Company and certain of its current and former officers and directors in the U.S. District Court for the Southern District of Ohio (Case No. 2:21-cv-01197) on behalf of certain Root shareholders. The complaint alleges that defendants made false or misleading statements and omissions of purportedly material fact, in violation of Sections 10(b) and 20(a) of the Exchange Act and Rule 10b-5 thereunder, and of Sections 11 and 15 of the Securities Act in connection with and following the Company’s initial public offering. The complaint seeks unspecified damages. The defendants’ motion to dismiss the claims set forth in the complaint was granted and the lawsuit was dismissed with prejudice on March 31, 2023, which dismissal has been appealed. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is in the early stages and, at this time, we cannot predict the outcome or estimate the likelihood or magnitude of our possible or potential loss contingency.

We are contingently liable for possible future assessments under regulatory requirements for insolvencies and impairments of unaffiliated insurance companies.

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OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME

9 Months Ended

Sep. 30, 2023

Equity [Abstract]

OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME

OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME

The following table presents the changes in our accumulated other comprehensive (loss) income, or AOCI, for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Beginning balance	$	(5.9)	$	(4.6)	$	(5.8)	$	0.4
Other comprehensive loss before reclassifications	(0.7)		(2.3)		(0.8)		(7.4)
Net realized losses on investments reclassified from AOCI to net loss	—		—		—		0.1
Other comprehensive loss	(0.7)		(2.3)		(0.8)		(7.3)
Ending balance	$	(6.6)	$	(6.9)	$	(6.6)	$	(6.9)

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LOSS PER SHARE

9 Months Ended

Sep. 30, 2023

Earnings Per Share [Abstract]

LOSS PER SHARE

LOSS PER SHARE

The following table displays the computation of basic and diluted loss per share for both Class A and Class B common stock for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(in millions, except per share amounts)
Net loss	$	(45.8)	$	(66.4)	$	(123.4)	$	(239.4)
Weighted-average common shares outstanding: basic and diluted (both Class A and B)	14.5		14.1		14.4		14.0
Loss per common share: basic and diluted (both Class A and B)	$	(3.16)	$	(4.71)	$	(8.57)	$	(17.10)

We excluded the following potentially dilutive common stock equivalents, presented based on amounts outstanding at each period end, from the computation of diluted loss per share attributable to common shareholders for the periods indicated because including them would have had an anti-dilutive effect:

	As of September 30,
	2023	2022
	(in millions)
Options to purchase common stock	0.1	0.2
Nonvested shares subject to repurchase	0.1	0.1
Restricted stock units and performance-based restricted stock units	2.0	1.3
Redeemable convertible preferred stock (as converted to common stock)	0.8	0.8
Warrants to purchase common stock	7.7	7.7
Total	10.7	10.1

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GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN

9 Months Ended

Sep. 30, 2023

Insurance [Abstract]

GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN

REINSURANCE

The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Premiums written:
Direct	$	192.7	$	139.6	$	444.6	$	443.9
Assumed	31.5		11.1		59.3		34.1
Ceded	(22.3)		(81.0)		(159.4)		(264.5)
Net premiums written	$	201.9	$	69.7	$	344.5	$	213.5
Premiums earned:
Direct	$	141.6	$	144.5	$	381.9	$	469.3
Assumed	18.2		10.8		39.5		31.5
Ceded	(59.8)		(86.7)		(197.5)		(279.2)
Net premiums earned	$	100.0	$	68.6	$	223.9	$	221.6
Losses and LAE incurred:
Direct	$	106.8	$	126.1	$	297.1	$	430.0
Assumed	13.4		11.3		29.8		35.7
Ceded	(34.4)		(56.5)		(118.3)		(192.4)
Net losses and LAE incurred	$	85.8	$	80.9	$	208.6	$	273.3

During the third quarter of 2023, we commuted certain agreements with our reinsurers which resulted in $4.4 million of net premiums earned, $4.2 million of loss and loss adjustment expenses and $5.8 million of other insurance expense (benefit), respectively, on the condensed consolidated statements of operations and comprehensive loss. A portion of the loss and loss adjustment expenses is related to an allowance for credit losses of $2.8 million, that was established due to a commutation with one of our reinsurers as of September 30, 2023.

Additionally, in connection with the commutation of certain agreements with reinsurers during the third quarter of 2023, we received cash and cash equivalents of $3.9 million, reinsurance recoverable and receivable decreased by $6.1 million, prepaid reinsurance premiums was reduced by $33.5 million and reinsurance premiums payable decreased by $30.2 million all of which are reported within the condensed consolidated balance sheets.

In the event that all or any of the reinsuring companies might be unable to meet their obligations under existing reinsurance agreements, we would be liable to the policyholder for such defaulted amounts.

GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN

Gross premiums written by state is as follows for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,								Nine Months Ended September 30,
	2023				2022				2023				2022
	Amount		% of Total		Amount		% of Total		Amount		% of Total		Amount		% of Total
	(dollars in millions)
State:
Texas	$	36.8	16.4	%	$	26.2	17.4	%	$	80.1	15.9	%	$	89.5	18.7	%
Georgia	26.3		11.7		15.0		10.0		56.0		11.1		48.8		10.2
Colorado	15.3		6.8		10.3		6.8		37.8		7.5		30.8		6.4
Pennsylvania	12.1		5.4		9.1		6.0		29.0		5.8		26.8		5.6
South Carolina	11.8		5.3		4.5		3.0		28.6		5.7		16.4		3.4
Utah	8.3		3.7		8.0		5.3		22.9		4.5		24.1		5.0
Arizona	11.0		4.9		4.3		2.9		21.7		4.3		13.3		2.8
Ohio	8.4		3.7		3.9		2.6		16.9		3.4		11.8		2.5
Oklahoma	7.2		3.2		5.2		3.5		16.7		3.3		16.1		3.4
Missouri	8.7		3.9		4.3		2.9		16.1		3.2		14.2		3.0
All others states	78.3		35.0		59.9		39.6		178.1		35.3		186.2		39.0
Total	$	224.2	100.0	%	$	150.7	100.0	%	$	503.9	100.0	%	$	478.0	100.0	%

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BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Policies)	9 Months Ended
	Sep. 30, 2023
Accounting Policies [Abstract]
Basis of Presentation	Basis of Presentation—In our opinion, all adjustments necessary for a fair presentation of the condensed consolidated financial statements have been included. All such adjustments are of a normal and recurring nature. These condensed consolidated financial statements are unaudited and, accordingly, should be read in conjunction with the consolidated financial statements and related notes included in the Annual Report on Form 10-K for the year ended December 31, 2022 filed with the Securities and Exchange Commission, or SEC, on February 22, 2023.
Basis of Consolidation	Basis of Consolidation—The unaudited condensed consolidated financial statements include the accounts of Root, Inc. and its subsidiaries, all of which are wholly owned. These financial statements have been prepared in accordance with accounting principles generally accepted in the United States, or GAAP. All intercompany accounts and transactions have been eliminated.
Use of Estimates	Use of Estimates—The preparation of the unaudited condensed consolidated financial statements requires management to make certain estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the unaudited condensed consolidated financial statements and the reported amounts of revenue and expenses during the reporting period. Actual results could differ from those estimates. Significant estimates reflected in our unaudited condensed consolidated financial statements include, but are not limited to, reserves for loss and loss adjustment expense, or LAE, valuation allowances for income taxes and allowance for expected credit losses on premium receivables and reinsurance recoverables.

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BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Tables)

9 Months Ended

Sep. 30, 2023

Accounting Policies [Abstract]

Schedule of Error Corrections and Prior Period Adjustments

The following tables present the effect of the revision on the condensed consolidated statements of operations and comprehensive loss for the three and nine months ended September 30, 2022, condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity and condensed consolidated statement of cash flows as of and for the nine months ended September 30, 2022.

	Three Months Ended September 30, 2022 (unaudited)						Nine Months Ended September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected		As reported		Adjustments		As Corrected
	(in millions, except per share amounts)
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing	$	5.7	$	2.4	$	8.1	$	45.8	$	(1.0)	$	44.8
General and administrative	26.4		—		26.4		86.3		10.1		96.4
Total operating expenses	128.4		2.4		130.8		445.8		9.1		454.9
Operating loss	(54.7)		(2.4)		(57.1)		(206.3)		(9.1)		(215.4)
Loss before income tax expense	(64.0)		(2.4)		(66.4)		(230.3)		(9.1)		(239.4)
Net loss	(64.0)		(2.4)		(66.4)		(230.3)		(9.1)		(239.4)
Comprehensive loss	$	(66.3)	$	(2.4)	$	(68.7)	$	(237.6)	$	(9.1)	$	(246.7)
Weighted-average common shares outstanding: basic and diluted (both Class A and B)	14.1				14.1		14.0				14.0
Loss per common share: basic and diluted (both Class A and B)	$	(4.54)			$	(4.71)	$	(16.45)			$	(17.10)

	As of September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected
	(in millions)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Accumulated loss	$	(1,500.4)	$	(9.1)	$	(1,509.5)
Total stockholders’ equity	$	330.9	$	(9.1)	$	321.8

	Nine Months Ended September 30, 2022 (unaudited)
	As reported		Adjustments		As Corrected
	(in millions)
Condensed consolidated statement of cash flows:
Net loss	$	(230.3)	$	(9.1)	$	(239.4)
Other assets	(11.1)		9.1		(2.0)
Net cash used in operating activities	$	(163.9)	$	—	$	(163.9)

Schedule of Cash and Cash Equivalents

The following table provides a reconciliation of cash, cash equivalents and restricted cash reported within the condensed consolidated balance sheets that sum to the total of the same such amount in the condensed consolidated statements of cash flows:

	As of
	September 30,		December 31,
	2023		2022
	(dollars in millions)
Cash and cash equivalents	$	635.3	$	762.1
Restricted cash	1.0		1.0
Total cash, cash equivalents and restricted cash shown in the condensed consolidated statements of cash flows	$	636.3	$	763.1

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INVESTMENTS (Tables)

9 Months Ended

Sep. 30, 2023

Investments, Debt and Equity Securities [Abstract]

Schedule of AFS Debt Securities

The amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities at September 30, 2023 and December 31, 2022 are as follows:

	September 30, 2023
	Amortized Cost		Allowance for Expected Credit Losses		Gross Unrealized Gains		Gross Unrealized Losses		Fair Value
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	16.8	$	—	$	—	$	(0.4)	$	16.4
Municipal securities	25.6		—		—		(1.3)		24.3
Corporate debt securities	69.4		—		—		(2.9)		66.5
Residential mortgage-backed securities	12.3		—		—		(0.5)		11.8
Commercial mortgage-backed securities	31.0		—		—		(1.3)		29.7
Other debt obligations	16.0		—		—		(0.2)		15.8
Total fixed maturities	171.1		—		—		(6.6)		164.5
Short-term investments	2.6		—		—		—		2.6
Total	$	173.7	$	—	$	—	$	(6.6)	$	167.1
	December 31, 2022
	Amortized Cost		Allowance for Expected Credit Losses		Gross Unrealized Gains		Gross Unrealized Losses		Fair Value
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	11.3	$	—	$	—	$	(0.3)	$	11.0
Municipal securities	21.4		—		—		(1.2)		20.2
Corporate debt securities	60.5		—		—		(2.7)		57.8
Residential mortgage-backed securities	5.5		—		—		(0.3)		5.2
Commercial mortgage-backed securities	24.4		—		—		(1.2)		23.2
Other debt obligations	11.1		—		0.1		(0.2)		11.0
Total fixed maturities	134.2		—		0.1		(5.9)		128.4
Short-term investments	0.4		—		—		—		0.4
Total	$	134.6	$	—	$	0.1	$	(5.9)	$	128.8

The following table reflects the gross and net realized gains and losses on short-term investments, available-for-sale fixed maturities and other investments that have been included in the condensed consolidated statements of operations and comprehensive loss for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Realized gains on investments	$	—	$	—	$	—	$	1.2
Realized losses on investments	—		—		—		(0.1)
Net realized gains on investments	$	—	$	—	$	—	$	1.1

The following table sets forth the amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities by contractual maturity at September 30, 2023:

	September 30, 2023
	Amortized Cost		Fair Value
	(dollars in millions)
Due in one year or less	$	33.3	$	32.8
Due after one year through five years	102.3		98.1
Due five years through 10 years	21.4		20.4
Due after 10 years	16.7		15.8
Total	$	173.7	$	167.1

Schedule of Unrealized Losses

The following tables reflect the gross unrealized losses and fair value of short-term investments and available-for-sale fixed maturity securities, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at September 30, 2023 and December 31, 2022:

	September 30, 2023
	Less than 12 Months				12 Months or More				Total
	Fair Value		Unrealized Loss		Fair Value		Unrealized Loss		Fair Value		Unrealized Loss
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	10.2	$	(0.2)	$	6.2	$	(0.2)	$	16.4	$	(0.4)
Municipal securities	7.9		(0.2)		15.7		(1.1)		23.6		(1.3)
Corporate debt securities	27.1		(0.8)		39.3		(2.1)		66.4		(2.9)
Residential mortgage-backed securities	8.5		(0.2)		2.7		(0.3)		11.2		(0.5)
Commercial mortgage-backed securities	13.5		(0.4)		15.8		(0.9)		29.3		(1.3)
Other debt obligations	9.5		(0.1)		3.8		(0.1)		13.3		(0.2)
Total fixed maturities	76.7		(1.9)		83.5		(4.7)		160.2		(6.6)
Short-term investments	1.1		—		—		—		1.1		—
Total	$	77.8	$	(1.9)	$	83.5	$	(4.7)	$	161.3	$	(6.6)
	December 31, 2022
	Less than 12 Months				12 Months or More				Total
	Fair Value		Unrealized Loss		Fair Value		Unrealized Loss		Fair Value		Unrealized Loss
	(dollars in millions)
Fixed maturities:
U.S. Treasury securities and agencies	$	6.9	$	(0.1)	$	4.1	$	(0.2)	$	11.0	$	(0.3)
Municipal securities	11.5		(0.5)		8.2		(0.7)		19.7		(1.2)
Corporate debt securities	45.3		(1.6)		11.5		(1.1)		56.8		(2.7)
Residential mortgage-backed securities	2.2		—		1.9		(0.3)		4.1		(0.3)
Commercial mortgage-backed securities	18.3		(0.8)		4.6		(0.4)		22.9		(1.2)
Other debt obligations	6.8		(0.2)		—		—		6.8		(0.2)
Total fixed maturities	91.0		(3.2)		30.3		(2.7)		121.3		(5.9)
Short-term investments	0.1		—		—		—		0.1		—
Total	$	91.1	$	(3.2)	$	30.3	$	(2.7)	$	121.4	$	(5.9)

Schedule of Net Investment Income

The following table sets forth the components of net investment income for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Interest on bonds	$	1.4	$	0.6	$	3.3	$	1.7
Interest on deposits and cash equivalents	7.9		0.6		19.8		1.2
Total	9.3		1.2		23.1		2.9
Investment expense	(0.3)		(0.3)		(0.6)		(0.7)
Net investment income	$	9.0	$	0.9	$	22.5	$	2.2

Schedule of Credit Ratings

The following tables summarize the credit ratings of short-term investments and available-for-sale fixed maturity securities at September 30, 2023 and December 31, 2022:

	September 30, 2023
	Amortized Cost		Fair Value		% of Total Fair Value
	(dollars in millions)
S&P Global rating or equivalent
AAA	$	51.2	$	49.3	29.5	%
AA+, AA, AA-, A-1	62.4		60.2		36.0
A+, A, A-	46.3		44.2		26.5
BBB+, BBB, BBB-	13.8		13.4		8.0
Total	$	173.7	$	167.1	100.0	%

	December 31, 2022
	Amortized Cost		Fair Value		% of Total Fair Value
	(dollars in millions)
S&P Global rating or equivalent
AAA	$	62.5	$	59.9	46.5	%
AA+, AA, AA-, A-1	19.9		19.1		14.8
A+, A, A-	38.4		36.5		28.3
BBB+, BBB, BBB-	13.8		13.3		10.4
Total	$	134.6	$	128.8	100.0	%

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FAIR VALUE OF FINANCIAL INSTRUMENTS (Tables)

9 Months Ended

Sep. 30, 2023

Fair Value Disclosures [Abstract]

Schedule of Fair Value

The following tables provide information about our financial assets measured and reported at fair value as of September 30, 2023 and December 31, 2022:

	September 30, 2023
	Level 1		Level 2		Level 3		Total Fair Value
	(dollars in millions)
Assets
Fixed maturities:
U.S. Treasury securities and agencies	$	15.4	$	1.0	$	—	$	16.4
Municipal securities	—		24.3		—		24.3
Corporate debt securities	—		66.5		—		66.5
Residential mortgage-backed securities	—		11.8		—		11.8
Commercial mortgage-backed securities	—		29.7		—		29.7
Other debt obligations	—		15.8		—		15.8
Total fixed maturities	15.4		149.1		—		164.5
Short-term investments	2.4		0.2		—		2.6
Cash equivalents	363.6		—		—		363.6
Total assets at fair value	$	381.4	$	149.3	$	—	$	530.7
	December 31, 2022
	Level 1		Level 2		Level 3		Total Fair Value
	(dollars in millions)
Assets
Fixed maturities:
U.S. Treasury securities and agencies	$	9.2	$	1.8	$	—	$	11.0
Municipal securities	—		20.2		—		20.2
Corporate debt securities	—		57.8		—		57.8
Residential mortgage-backed securities	—		5.2		—		5.2
Commercial mortgage-backed securities	—		23.2		—		23.2
Other debt obligations	—		11.0		—		11.0
Total fixed maturities	9.2		119.2		—		128.4
Short-term investments	—		0.4		—		0.4
Cash equivalents	487.3		—		—		487.3
Total assets at fair value	$	496.5	$	119.6	$	—	$	616.1

Schedule of Carrying Amounts and Fair Values of Financial Instruments

As of September 30, 2023 and December 31, 2022, the carrying amounts and fair values of these financial instruments were as follows:

	Carrying Amount as of September 30, 2023		Estimated Fair Value as of September 30, 2023		Carrying Amount as of December 31, 2022		Estimated Fair Value as of December 31, 2022
	(dollars in millions)
Long-term debt	$	298.3	$	304.8	$	295.4	$	309.7

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LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Tables)

9 Months Ended

Sep. 30, 2023

Insurance [Abstract]

Schedule of Reconciliation of Reserve Balances for Loss and LAE, Net of Reinsurance

The following provides a reconciliation of the beginning and ending reserve balances for loss and LAE, net of reinsurance:

	Nine Months Ended September 30,
	2023		2022
	(dollars in millions)
Gross loss and LAE reserves, January 1	$	287.4	$	320.2
Reinsurance recoverable on unpaid losses	(76.4)		(79.5)
Net loss and LAE reserves, January 1	211.0		240.7
Net incurred loss and LAE related to:
Current year	209.2		273.5
Prior years	(0.6)		(0.2)
Total incurred	208.6		273.3
Net paid loss and LAE related to:
Current year	87.4		155.5
Prior years	117.3		135.6
Total paid	204.7		291.1
Net loss and LAE reserves, September 30	214.9		222.9
Plus reinsurance recoverable on unpaid losses	41.6		71.3
Gross loss and LAE reserves, September 30	$	256.5	$	294.2

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REINSURANCE (Tables)

9 Months Ended

Sep. 30, 2023

Insurance [Abstract]

Schedule of Comprehensive Loss For Reinsurance

The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Premiums written:
Direct	$	192.7	$	139.6	$	444.6	$	443.9
Assumed	31.5		11.1		59.3		34.1
Ceded	(22.3)		(81.0)		(159.4)		(264.5)
Net premiums written	$	201.9	$	69.7	$	344.5	$	213.5
Premiums earned:
Direct	$	141.6	$	144.5	$	381.9	$	469.3
Assumed	18.2		10.8		39.5		31.5
Ceded	(59.8)		(86.7)		(197.5)		(279.2)
Net premiums earned	$	100.0	$	68.6	$	223.9	$	221.6
Losses and LAE incurred:
Direct	$	106.8	$	126.1	$	297.1	$	430.0
Assumed	13.4		11.3		29.8		35.7
Ceded	(34.4)		(56.5)		(118.3)		(192.4)
Net losses and LAE incurred	$	85.8	$	80.9	$	208.6	$	273.3

Gross premiums written by state is as follows for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,								Nine Months Ended September 30,
	2023				2022				2023				2022
	Amount		% of Total		Amount		% of Total		Amount		% of Total		Amount		% of Total
	(dollars in millions)
State:
Texas	$	36.8	16.4	%	$	26.2	17.4	%	$	80.1	15.9	%	$	89.5	18.7	%
Georgia	26.3		11.7		15.0		10.0		56.0		11.1		48.8		10.2
Colorado	15.3		6.8		10.3		6.8		37.8		7.5		30.8		6.4
Pennsylvania	12.1		5.4		9.1		6.0		29.0		5.8		26.8		5.6
South Carolina	11.8		5.3		4.5		3.0		28.6		5.7		16.4		3.4
Utah	8.3		3.7		8.0		5.3		22.9		4.5		24.1		5.0
Arizona	11.0		4.9		4.3		2.9		21.7		4.3		13.3		2.8
Ohio	8.4		3.7		3.9		2.6		16.9		3.4		11.8		2.5
Oklahoma	7.2		3.2		5.2		3.5		16.7		3.3		16.1		3.4
Missouri	8.7		3.9		4.3		2.9		16.1		3.2		14.2		3.0
All others states	78.3		35.0		59.9		39.6		178.1		35.3		186.2		39.0
Total	$	224.2	100.0	%	$	150.7	100.0	%	$	503.9	100.0	%	$	478.0	100.0	%

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LONG-TERM DEBT (Tables)

9 Months Ended

Sep. 30, 2023

Debt Disclosure [Abstract]

Schedule of Long Term Debt

The following summarizes the carrying value of long-term debt as of September 30, 2023 and December 31, 2022:

	September 30, 2023		December 31, 2022
	(dollars in millions)
Term Loan	$	300.0	$	300.0
Accrued interest payable	7.9		7.3
Unamortized discount, debt issuance costs and warrants	(9.6)		(11.9)
Total	$	298.3	$	295.4

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RESTRUCTURING COSTS (Tables)

9 Months Ended

Sep. 30, 2023

Restructuring and Related Activities [Abstract]

Restructuring Costs

The following table displays restructuring costs recorded in general and administrative expenses on the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,				Cumulative Incurred Through September 30, 2023
	2023		2022		2023		2022
	(dollars in millions)
Restructuring costs:
Employee costs	$	1.8	$	—	$	5.9	$	5.6	$	21.4
Real estate exit costs	—		—		—		2.1		2.1
Other costs	0.1		—		3.5		0.7		4.5
Total restructuring costs	$	1.9	$	—	$	9.4	$	8.4	$	28.0

The following table displays a rollforward of the accrual for restructuring costs recorded in other liabilities on the condensed consolidated balance sheets:

	Employee costs		Other costs		Total liability
	(dollars in millions)
Restructuring activity:
Restructuring liability as of January 1, 2023	$	3.1	$	0.1	$	3.2
Expense incurred	5.5		3.4		8.9
Payments	(2.0)		(3.5)		(5.5)
Restructuring liability as of September 30, 2023	$	6.6	$	—	$	6.6

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SHARE-BASED COMPENSATION (Tables)

9 Months Ended

Sep. 30, 2023

Share-Based Payment Arrangement [Abstract]

Schedule of Share-Based Compensation Expense

The following table displays warrant compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Warrant compensation expense:
Sales and marketing	$	—	$	—	$	—	$	8.8
Other insurance expense (benefit)	5.0		1.5		13.3		1.5
Total warrant compensation expense	$	5.0	$	1.5	$	13.3	$	10.3

The following table displays share-based compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Share-based compensation expense:
Loss and loss adjustment expenses	$	0.2	$	0.2	$	0.5	$	0.6
Sales and marketing	0.1		0.3		0.3		0.7
Other insurance expense (benefit)	0.1		0.3		0.4		0.8
Technology and development	0.9		1.1		2.4		3.1
General and administrative	3.4		5.9		8.8		16.6
Total share-based compensation expense	$	4.7	$	7.8	$	12.4	$	21.8

The following table provides total share-based compensation expense by type of award:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Share-based compensation expense:
Restricted stock unit expense	$	4.4	$	7.4	$	11.4	$	20.5
Performance-based restricted stock unit expense	0.1		—		0.1		—
Stock option expense	0.2		0.4		0.9		1.3
Total share-based compensation expense	$	4.7	$	7.8	$	12.4	$	21.8

Summary of Performance Stock Units

The following table provides other key terms of the PSUs:

Performance-Based Restricted Stock Units	Stock Price Goals		Shares Issued	Grant Date Fair Value per Share
	(in millions, except per share amounts)
Tranches:
Tranche 1	$	16.76	—	$	7.69
Tranche 2	25.14		0.1	6.70
Tranche 3	33.52		0.1	5.87
Tranche 4	$	41.90	0.2	$	5.10
			0.4

Summary of RSU Activity

A summary of RSU and PSU activity for the nine months ended September 30, 2023 is as follows:

	Nine Months Ended September 30, 2023
Restricted Stock Units and Performance-Based Restricted Stock Units	Number of Shares	Weighted-Average Grant Date Fair Value per Share		Aggregate Intrinsic Value
	(in millions, except per share amounts)
Nonvested at January 1, 2023	1.1	$	51.81	$	5.0
Granted	1.6	6.62
Vested	(0.5)	50.44		2.8
Forfeited, expired or canceled	(0.2)	53.75
Nonvested at September 30, 2023	2.0	$	15.79	$	18.9

Summary of Option Activity

A summary of option activity for the nine months ended September 30, 2023 is as follows:

	Nine Months Ended September 30, 2023
Options	Number of Shares	Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Term (in Years)	Aggregate Intrinsic Value
	(in millions, except exercise price and term amounts)
Outstanding and exercisable at January 1, 2023	0.2	$	38.15	5.63	$	0.2
Granted	—	8.94
Exercised	—	—			—
Forfeited, expired or canceled	(0.1)	44.86
Outstanding and exercisable at September 30, 2023	0.1	$	33.74	4.53	$	0.5

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OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME (Tables)

9 Months Ended

Sep. 30, 2023

Equity [Abstract]

Schedule of AOCI

The following table presents the changes in our accumulated other comprehensive (loss) income, or AOCI, for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Beginning balance	$	(5.9)	$	(4.6)	$	(5.8)	$	0.4
Other comprehensive loss before reclassifications	(0.7)		(2.3)		(0.8)		(7.4)
Net realized losses on investments reclassified from AOCI to net loss	—		—		—		0.1
Other comprehensive loss	(0.7)		(2.3)		(0.8)		(7.3)
Ending balance	$	(6.6)	$	(6.9)	$	(6.6)	$	(6.9)

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LOSS PER SHARE (Tables)

9 Months Ended

Sep. 30, 2023

Earnings Per Share [Abstract]

Schedule of Earnings Per Share

The following table displays the computation of basic and diluted loss per share for both Class A and Class B common stock for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(in millions, except per share amounts)
Net loss	$	(45.8)	$	(66.4)	$	(123.4)	$	(239.4)
Weighted-average common shares outstanding: basic and diluted (both Class A and B)	14.5		14.1		14.4		14.0
Loss per common share: basic and diluted (both Class A and B)	$	(3.16)	$	(4.71)	$	(8.57)	$	(17.10)

Schedule of Anti-Dilutive Securities

We excluded the following potentially dilutive common stock equivalents, presented based on amounts outstanding at each period end, from the computation of diluted loss per share attributable to common shareholders for the periods indicated because including them would have had an anti-dilutive effect:

	As of September 30,
	2023	2022
	(in millions)
Options to purchase common stock	0.1	0.2
Nonvested shares subject to repurchase	0.1	0.1
Restricted stock units and performance-based restricted stock units	2.0	1.3
Redeemable convertible preferred stock (as converted to common stock)	0.8	0.8
Warrants to purchase common stock	7.7	7.7
Total	10.7	10.1

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GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN (Tables)

9 Months Ended

Sep. 30, 2023

Insurance [Abstract]

Schedule of Direct and Assumed Premiums Written

The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
	(dollars in millions)
Premiums written:
Direct	$	192.7	$	139.6	$	444.6	$	443.9
Assumed	31.5		11.1		59.3		34.1
Ceded	(22.3)		(81.0)		(159.4)		(264.5)
Net premiums written	$	201.9	$	69.7	$	344.5	$	213.5
Premiums earned:
Direct	$	141.6	$	144.5	$	381.9	$	469.3
Assumed	18.2		10.8		39.5		31.5
Ceded	(59.8)		(86.7)		(197.5)		(279.2)
Net premiums earned	$	100.0	$	68.6	$	223.9	$	221.6
Losses and LAE incurred:
Direct	$	106.8	$	126.1	$	297.1	$	430.0
Assumed	13.4		11.3		29.8		35.7
Ceded	(34.4)		(56.5)		(118.3)		(192.4)
Net losses and LAE incurred	$	85.8	$	80.9	$	208.6	$	273.3

Gross premiums written by state is as follows for the three and nine months ended September 30, 2023 and 2022:

	Three Months Ended September 30,								Nine Months Ended September 30,
	2023				2022				2023				2022
	Amount		% of Total		Amount		% of Total		Amount		% of Total		Amount		% of Total
	(dollars in millions)
State:
Texas	$	36.8	16.4	%	$	26.2	17.4	%	$	80.1	15.9	%	$	89.5	18.7	%
Georgia	26.3		11.7		15.0		10.0		56.0		11.1		48.8		10.2
Colorado	15.3		6.8		10.3		6.8		37.8		7.5		30.8		6.4
Pennsylvania	12.1		5.4		9.1		6.0		29.0		5.8		26.8		5.6
South Carolina	11.8		5.3		4.5		3.0		28.6		5.7		16.4		3.4
Utah	8.3		3.7		8.0		5.3		22.9		4.5		24.1		5.0
Arizona	11.0		4.9		4.3		2.9		21.7		4.3		13.3		2.8
Ohio	8.4		3.7		3.9		2.6		16.9		3.4		11.8		2.5
Oklahoma	7.2		3.2		5.2		3.5		16.7		3.3		16.1		3.4
Missouri	8.7		3.9		4.3		2.9		16.1		3.2		14.2		3.0
All others states	78.3		35.0		59.9		39.6		178.1		35.3		186.2		39.0
Total	$	224.2	100.0	%	$	150.7	100.0	%	$	503.9	100.0	%	$	478.0	100.0	%

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NATURE OF BUSINESS (Details)	Sep. 30, 2023
Root Insurance Company
Schedule of Equity Method Investments [Line Items]
Ownership percentage (as percent)	100.00%
Root Property & Casualty Insurance Company
Schedule of Equity Method Investments [Line Items]
Ownership percentage (as percent)	100.00%
Root Reinsurance Company, Ltd.
Schedule of Equity Method Investments [Line Items]
Ownership percentage (as percent)	100.00%

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BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Error Correction (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022	Jun. 30, 2023	Dec. 31, 2022	Jun. 30, 2022	Dec. 31, 2021
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing	$ 13.1	$ 8.1	$ 22.8	$ 44.8
General and administrative	21.0	26.4	63.2	96.4
Total operating expenses	149.3	130.8	349.2	454.9
Operating loss	(34.0)	(57.1)	(89.0)	(215.4)
Loss before income tax expense	(45.8)	(66.4)	(123.4)	(239.4)
Net loss	(45.8)	(66.4)	(123.4)	(239.4)
Comprehensive loss	$ (46.5)	$ (68.7)	$ (124.2)	$ (246.7)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)	14.5	14.1	14.4	14.0
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)	14.5	14.1	14.4	14.0
Loss per common share: basic (both Class A and B) (in dollars per share)	$ (3.16)	$ (4.71)	$ (8.57)	$ (17.10)
Loss per common share: diluted (both Class A and B) (in dollars per share)	$ (3.16)	$ (4.71)	$ (8.57)	$ (17.10)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Total stockholders’ equity	$ 177.1	$ 321.8	$ 177.1	$ 321.8	$ 214.4	$ 277.1	$ 381.3	$ 536.4
Condensed consolidated statement of cash flows:
Net loss	(45.8)	(66.4)	(123.4)	(239.4)
Other assets			10.6	(2.0)
Net cash used in operating activities			(79.7)	(163.9)
Accumulated Loss
Condensed consolidated statements of operations and comprehensive loss:
Net loss	(45.8)	(66.4)	(123.4)	(239.4)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Total stockholders’ equity	(1,691.2)	(1,509.5)	(1,691.2)	(1,509.5)	$ (1,645.4)	$ (1,567.8)	$ (1,443.1)	$ (1,270.1)
Condensed consolidated statement of cash flows:
Net loss	$ (45.8)	(66.4)	$ (123.4)	(239.4)
As reported
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing		5.7		45.8
General and administrative		26.4		86.3
Total operating expenses		128.4		445.8
Operating loss		(54.7)		(206.3)
Loss before income tax expense		(64.0)		(230.3)
Net loss		(64.0)		(230.3)
Comprehensive loss		$ (66.3)		$ (237.6)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)		14.1		14.0
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)		14.1		14.0
Loss per common share: basic (both Class A and B) (in dollars per share)		$ (4.54)		$ (16.45)
Loss per common share: diluted (both Class A and B) (in dollars per share)		$ (4.54)		$ (16.45)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Total stockholders’ equity		$ 330.9		$ 330.9
Condensed consolidated statement of cash flows:
Net loss		(64.0)		(230.3)
Other assets				(11.1)
Net cash used in operating activities				(163.9)
As reported | Accumulated Loss
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Total stockholders’ equity		(1,500.4)		(1,500.4)
Adjustments
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing		2.4		(1.0)
General and administrative		0.0		10.1
Total operating expenses		2.4		9.1
Operating loss		(2.4)		(9.1)
Loss before income tax expense		(2.4)		(9.1)
Net loss		(2.4)		(9.1)
Comprehensive loss		(2.4)		(9.1)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Total stockholders’ equity		(9.1)		(9.1)
Condensed consolidated statement of cash flows:
Net loss		(2.4)		(9.1)
Other assets				9.1
Adjustments | Accumulated Loss
Condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity:
Total stockholders’ equity		$ (9.1)		$ (9.1)

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BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Cash, Cash Equivalents and Restricted Cash (Details) - USD ($) $ in Millions	Sep. 30, 2023	Dec. 31, 2022	Sep. 30, 2022	Dec. 31, 2021
Accounting Policies [Abstract]
Cash and cash equivalents	$ 635.3	$ 762.1
Restricted cash	1.0	1.0
Total cash, cash equivalents and restricted cash shown in the condensed consolidated statements of cash flows	$ 636.3	$ 763.1	$ 820.7	$ 707.0

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BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Additional Information (Details) shares in Millions	3 Months Ended	9 Months Ended
	Sep. 30, 2023 consecutive_trading_day shares	Sep. 30, 2023 shares
Class A Shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Consecutive trading days | consecutive_trading_day	45
Performance-based RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares) | shares	0.4	0.4
Volatility rate	50.00%	76.00%
Weighted average volatility rate	50.00%
Minimum | Performance-based RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Vesting period	1 year
Maximum | Performance-based RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Vesting period	4 years

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INVESTMENTS - Amortized Cost and Fair Value (Details) - USD ($) $ in Millions	Sep. 30, 2023	Dec. 31, 2022
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 173.7	$ 134.6
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.1
Gross Unrealized Losses	(6.6)	(5.9)
Fair Value	167.1	128.8
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	16.8	11.3
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.0
Gross Unrealized Losses	(0.4)	(0.3)
Fair Value	16.4	11.0
Municipal securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	25.6	21.4
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.0
Gross Unrealized Losses	(1.3)	(1.2)
Fair Value	24.3	20.2
Corporate debt securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	69.4	60.5
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.0
Gross Unrealized Losses	(2.9)	(2.7)
Fair Value	66.5	57.8
Residential mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	12.3	5.5
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.0
Gross Unrealized Losses	(0.5)	(0.3)
Fair Value	11.8	5.2
Commercial mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	31.0	24.4
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.0
Gross Unrealized Losses	(1.3)	(1.2)
Fair Value	29.7	23.2
Other debt obligations
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	16.0	11.1
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.1
Gross Unrealized Losses	(0.2)	(0.2)
Fair Value	15.8	11.0
Total fixed maturities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	171.1	134.2
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.1
Gross Unrealized Losses	(6.6)	(5.9)
Fair Value	164.5	128.4
Short-term investments
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	2.6	0.4
Allowance for Expected Credit Losses	0.0	0.0
Gross Unrealized Gains	0.0	0.0
Gross Unrealized Losses	0.0	0.0
Fair Value	$ 2.6	$ 0.4

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INVESTMENTS - Unrealized Losses (Details) - USD ($) $ in Millions	Sep. 30, 2023	Dec. 31, 2022
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	$ 77.8	$ 91.1
Less than 12 months, unrealized loss	(1.9)	(3.2)
12 months or more, fair value	83.5	30.3
12 months or more, unrealized loss	(4.7)	(2.7)
Total, fair value	161.3	121.4
Total, unrealized loss	(6.6)	(5.9)
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	10.2	6.9
Less than 12 months, unrealized loss	(0.2)	(0.1)
12 months or more, fair value	6.2	4.1
12 months or more, unrealized loss	(0.2)	(0.2)
Total, fair value	16.4	11.0
Total, unrealized loss	(0.4)	(0.3)
Municipal securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	7.9	11.5
Less than 12 months, unrealized loss	(0.2)	(0.5)
12 months or more, fair value	15.7	8.2
12 months or more, unrealized loss	(1.1)	(0.7)
Total, fair value	23.6	19.7
Total, unrealized loss	(1.3)	(1.2)
Corporate debt securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	27.1	45.3
Less than 12 months, unrealized loss	(0.8)	(1.6)
12 months or more, fair value	39.3	11.5
12 months or more, unrealized loss	(2.1)	(1.1)
Total, fair value	66.4	56.8
Total, unrealized loss	(2.9)	(2.7)
Residential mortgage-backed securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	8.5	2.2
Less than 12 months, unrealized loss	(0.2)	0.0
12 months or more, fair value	2.7	1.9
12 months or more, unrealized loss	(0.3)	(0.3)
Total, fair value	11.2	4.1
Total, unrealized loss	(0.5)	(0.3)
Commercial mortgage-backed securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	13.5	18.3
Less than 12 months, unrealized loss	(0.4)	(0.8)
12 months or more, fair value	15.8	4.6
12 months or more, unrealized loss	(0.9)	(0.4)
Total, fair value	29.3	22.9
Total, unrealized loss	(1.3)	(1.2)
Other debt obligations
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	9.5	6.8
Less than 12 months, unrealized loss	(0.1)	(0.2)
12 months or more, fair value	3.8	0.0
12 months or more, unrealized loss	(0.1)	0.0
Total, fair value	13.3	6.8
Total, unrealized loss	(0.2)	(0.2)
Total fixed maturities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	76.7	91.0
Less than 12 months, unrealized loss	(1.9)	(3.2)
12 months or more, fair value	83.5	30.3
12 months or more, unrealized loss	(4.7)	(2.7)
Total, fair value	160.2	121.3
Total, unrealized loss	(6.6)	(5.9)
Short-term investments
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	1.1	0.1
Less than 12 months, unrealized loss	0.0	0.0
12 months or more, fair value	0.0	0.0
12 months or more, unrealized loss	0.0	0.0
Total, fair value	1.1	0.1
Total, unrealized loss	$ 0.0	$ 0.0

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INVESTMENTS - Other Investments (Details) - USD ($)	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022	Dec. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Other investments	$ 4,400,000		$ 4,400,000		$ 4,400,000
Realized gains on investments	$ 0	$ 0	$ 0	$ 1,200,000

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INVESTMENTS - Gross and Net Realized Gains and Losses (Details) - USD ($)	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Investments, Debt and Equity Securities [Abstract]
Realized gains on investments	$ 0	$ 0	$ 0	$ 1,200,000
Realized losses on investments	0	0	0	(100,000)
Net realized gains on investments	$ 0	$ 0	$ 0	$ 1,100,000

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INVESTMENTS - Contractual Maturity (Details) - USD ($) $ in Millions	Sep. 30, 2023	Dec. 31, 2022
Amortized Cost
Due in one year or less	$ 33.3
Due after one year through five years	102.3
Due five years through 10 years	21.4
Due after 10 years	16.7
Amortized Cost	173.7	$ 134.6
Fair Value
Due in one year or less	32.8
Due after one year through five years	98.1
Due five years through 10 years	20.4
Due after 10 years	15.8
Total	$ 167.1	$ 128.8

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INVESTMENTS - Net Investment Income (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Net Investment Income [Line Items]
Realized gain value	$ 9.3	$ 1.2	$ 23.1	$ 2.9
Investment expense	(0.3)	(0.3)	(0.6)	(0.7)
Net investment income	9.0	0.9	22.5	2.2
Interest on bonds
Net Investment Income [Line Items]
Realized gain value	1.4	0.6	3.3	1.7
Interest on deposits and cash equivalents
Net Investment Income [Line Items]
Realized gain value	$ 7.9	$ 0.6	$ 19.8	$ 1.2

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INVESTMENTS - Credit Ratings (Details) - USD ($) $ in Millions	9 Months Ended	12 Months Ended
	Sep. 30, 2023	Dec. 31, 2022
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 173.7	$ 134.6
Fair Value	$ 167.1	$ 128.8
AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	100.00%	100.00%
AAA
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 51.2	$ 62.5
Fair Value	$ 49.3	$ 59.9
AAA | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	29.50%	46.50%
AA+, AA, AA-, A-1
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 62.4	$ 19.9
Fair Value	$ 60.2	$ 19.1
AA+, AA, AA-, A-1 | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	36.00%	14.80%
A+, A, A-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 46.3	$ 38.4
Fair Value	$ 44.2	$ 36.5
A+, A, A- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	26.50%	28.30%
BBB+, BBB, BBB-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 13.8	$ 13.8
Fair Value	$ 13.4	$ 13.3
BBB+, BBB, BBB- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	8.00%	10.40%

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FAIR VALUE OF FINANCIAL INSTRUMENTS - Balance Sheet Grouping (Details) - USD ($) $ in Millions	Sep. 30, 2023	Dec. 31, 2022
Assets
AFS securities	$ 167.1	$ 128.8
Cash equivalents	363.6	487.3
Total assets at fair value	530.7	616.1
U.S. Treasury securities and agencies
Assets
AFS securities	16.4	11.0
Municipal securities
Assets
AFS securities	24.3	20.2
Corporate debt securities
Assets
AFS securities	66.5	57.8
Residential mortgage-backed securities
Assets
AFS securities	11.8	5.2
Commercial mortgage-backed securities
Assets
AFS securities	29.7	23.2
Other debt obligations
Assets
AFS securities	15.8	11.0
Total fixed maturities
Assets
AFS securities	164.5	128.4
Short-term investments
Assets
AFS securities	2.6	0.4
Level 1
Assets
Cash equivalents	363.6	487.3
Total assets at fair value	381.4	496.5
Level 1 | U.S. Treasury securities and agencies
Assets
AFS securities	15.4	9.2
Level 1 | Municipal securities
Assets
AFS securities	0.0	0.0
Level 1 | Corporate debt securities
Assets
AFS securities	0.0	0.0
Level 1 | Residential mortgage-backed securities
Assets
AFS securities	0.0	0.0
Level 1 | Commercial mortgage-backed securities
Assets
AFS securities	0.0	0.0
Level 1 | Other debt obligations
Assets
AFS securities	0.0	0.0
Level 1 | Total fixed maturities
Assets
AFS securities	15.4	9.2
Level 1 | Short-term investments
Assets
AFS securities	2.4	0.0
Level 2
Assets
Cash equivalents	0.0	0.0
Total assets at fair value	149.3	119.6
Level 2 | U.S. Treasury securities and agencies
Assets
AFS securities	1.0	1.8
Level 2 | Municipal securities
Assets
AFS securities	24.3	20.2
Level 2 | Corporate debt securities
Assets
AFS securities	66.5	57.8
Level 2 | Residential mortgage-backed securities
Assets
AFS securities	11.8	5.2
Level 2 | Commercial mortgage-backed securities
Assets
AFS securities	29.7	23.2
Level 2 | Other debt obligations
Assets
AFS securities	15.8	11.0
Level 2 | Total fixed maturities
Assets
AFS securities	149.1	119.2
Level 2 | Short-term investments
Assets
AFS securities	0.2	0.4
Level 3
Assets
Cash equivalents	0.0	0.0
Total assets at fair value	0.0	0.0
Level 3 | U.S. Treasury securities and agencies
Assets
AFS securities	0.0	0.0
Level 3 | Municipal securities
Assets
AFS securities	0.0	0.0
Level 3 | Corporate debt securities
Assets
AFS securities	0.0	0.0
Level 3 | Residential mortgage-backed securities
Assets
AFS securities	0.0	0.0
Level 3 | Commercial mortgage-backed securities
Assets
AFS securities	0.0	0.0
Level 3 | Other debt obligations
Assets
AFS securities	0.0	0.0
Level 3 | Total fixed maturities
Assets
AFS securities	0.0	0.0
Level 3 | Short-term investments
Assets
AFS securities	$ 0.0	$ 0.0

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FAIR VALUE OF FINANCIAL INSTRUMENTS - Long Term Debt (Details) - Level 2 - USD ($) $ in Millions	Sep. 30, 2023	Dec. 31, 2022
Carrying amount
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 298.3	$ 295.4
Estimated Fair Value
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 304.8	$ 309.7

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LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES - Schedule of Reserve Balance (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022	Dec. 31, 2022	Dec. 31, 2021
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Gross loss and LAE reserves, January 1			$ 287.4	$ 320.2
Reinsurance recoverable on unpaid losses			(76.4)	(79.5)
Net loss and LAE reserves, January 1	$ 214.9	$ 222.9	214.9	222.9	$ 211.0	$ 240.7
Net incurred loss and LAE related to:
Current year			209.2	273.5
Prior years			(0.6)	(0.2)
Total incurred	85.8	80.9	208.6	273.3
Net paid loss and LAE related to:
Current year			87.4	155.5
Prior years			117.3	135.6
Total paid			204.7	291.1
Net loss and LAE reserves, September 30	214.9	222.9	214.9	222.9
Plus reinsurance recoverable on unpaid losses	41.6	71.3	41.6	71.3
Gross loss and LAE reserves, September 30	$ 256.5	$ 294.2	$ 256.5	$ 294.2

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LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES - Narrative (Details) - USD ($) $ in Millions	9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022
Insurance [Abstract]
Incurred losses and LAE attributable to prior accident years	$ 0.6	$ 0.2

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REINSURANCE (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Premiums written:
Direct	$ 192.7	$ 139.6	$ 444.6	$ 443.9
Assumed	31.5	11.1	59.3	34.1
Ceded	(22.3)	(81.0)	(159.4)	(264.5)
Net premiums written	201.9	69.7	344.5	213.5
Premiums earned:
Direct	141.6	144.5	381.9	469.3
Assumed	18.2	10.8	39.5	31.5
Ceded	(59.8)	(86.7)	(197.5)	(279.2)
Net premiums earned	100.0	68.6	223.9	221.6
Losses and LAE incurred:
Direct	106.8	126.1	297.1	430.0
Assumed	13.4	11.3	29.8	35.7
Ceded	(34.4)	(56.5)	(118.3)	(192.4)
Net losses and LAE incurred	$ 85.8	$ 80.9	$ 208.6	$ 273.3

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REINSURANCE - Narrative (Details) - USD ($) $ in Millions	3 Months Ended	9 Months Ended
	Sep. 30, 2023	Sep. 30, 2023	Sep. 30, 2022	Dec. 31, 2022
Effects of Reinsurance [Line Items]
Increase of net premiums earned	$ 4.4
Expense related to allowance for credit loss	2.8
Cash and cash equivalents	635.3	$ 635.3		$ 762.1
Reinsurance recoverable and receivable		8.5	$ 19.0
Prepaid reinsurance premiums		38.1	14.6
Reinsurance premiums payable		48.0	$ (8.8)
Commutation of Certain Agreements
Effects of Reinsurance [Line Items]
Cash and cash equivalents	3.9	$ 3.9
Reinsurance recoverable and receivable	6.1
Prepaid reinsurance premiums	33.5
Reinsurance premiums payable	30.2
Loss and loss adjustment expenses
Effects of Reinsurance [Line Items]
Incurred expense for commutations of certain reinsurance agreements	4.2
Other insurance expense (benefit)
Effects of Reinsurance [Line Items]
Incurred expense for commutations of certain reinsurance agreements	$ 5.8

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LONG-TERM DEBT - Narrative (Details) - Term Loan - USD ($)		1 Months Ended
	Jan. 27, 2022	Jan. 31, 2022
SOFR
Debt Instrument [Line Items]
Debt instrument, floor interest rate (in percent)	1.00%
Variable rate percentage (in percent)	9.00%
Secured debt
Debt Instrument [Line Items]
Debt amount		$ 300,000,000
Debt instrument, term		5 years

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LONG-TERM DEBT - Schedule Of Debt (Details) - USD ($) $ in Millions	Sep. 30, 2023	Dec. 31, 2022
Debt Instrument [Line Items]
Accrued interest payable	$ 7.9	$ 7.3
Unamortized discount, debt issuance costs and warrants	(9.6)	(11.9)
Total	298.3	295.4
Secured debt | Term Loan
Debt Instrument [Line Items]
Term Loan	$ 300.0	$ 300.0

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INCOME TAXES (Details)	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Income Tax Disclosure [Abstract]
Effective income tax rate	0.00%	0.00%	0.00%	0.00%
Federal income tax rate (in percent)			21.00%

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RESTRUCTURING COSTS - Narrative (Details) $ in Millions	Sep. 30, 2023 USD ($)
Restructuring and Related Activities [Abstract]
Restructuring and related cost, expected cost	$ 1.7

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RESTRUCTURING COSTS - Restructuring Costs Recorded In Consolidated Statements Of Operations And Comprehensive Loss (Details) - General and administrative - USD ($) $ in Millions	3 Months Ended		9 Months Ended		21 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023
Restructuring Cost and Reserve [Line Items]
Total restructuring costs	$ 1.9	$ 0.0	$ 9.4	$ 8.4	$ 28.0
Employee costs
Restructuring Cost and Reserve [Line Items]
Total restructuring costs	1.8	0.0	5.9	5.6	21.4
Real estate exit costs
Restructuring Cost and Reserve [Line Items]
Total restructuring costs	0.0	0.0	0.0	2.1	2.1
Other costs
Restructuring Cost and Reserve [Line Items]
Total restructuring costs	$ 0.1	$ 0.0	$ 3.5	$ 0.7	$ 4.5

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RESTRUCTURING COSTS - Restructuring Costs Recorded In Consolidated Balance Sheets (Details) $ in Millions	9 Months Ended
	Sep. 30, 2023 USD ($)
Restructuring activity:
Restructuring liability, beginning balance	$ 3.2
Expense incurred	8.9
Payments	(5.5)
Restructuring liability, ending balance	6.6
Employee costs
Restructuring activity:
Restructuring liability, beginning balance	3.1
Expense incurred	5.5
Payments	(2.0)
Restructuring liability, ending balance	6.6
Other costs
Restructuring activity:
Restructuring liability, beginning balance	0.1
Expense incurred	3.4
Payments	(3.5)
Restructuring liability, ending balance	$ 0.0

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SHARE-BASED COMPENSATION - Narrative (Details) shares in Millions, $ in Millions	3 Months Ended	9 Months Ended
	Sep. 30, 2023 USD ($) shares	Sep. 30, 2023 USD ($) shares	Oct. 31, 2021 tranche shares
2020 Equity Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares available for issuance (in shares) | shares	1.2	1.2
Warrant
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	$ 7.8	$ 7.8
Unrecognized compensation cost, period of recognition		1 year
Stock option expense
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, period of recognition		3 years
Unrecognized compensation cost, options	1.2	$ 1.2
Restricted stock unit expense
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	25.3	$ 25.3
Unrecognized compensation cost, period of recognition		4 years
Performance-based RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost	$ 2.2	$ 2.2
Expected term		5 years
Risk-free interest rate		4.06%
Dividend rate		0.00%
Volatility rate	50.00%	76.00%
Class A Shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares issued (in shares) | shares			7.2
Short Term Warrant
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of tranches | tranche			3
Long Term Warrant
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of tranches | tranche			5
Carvana
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of tranches | tranche			8

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SHARE-BASED COMPENSATION - Warrant Compensation Expense (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 4.7	$ 7.8	$ 12.4	$ 21.8
Sales and marketing
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	0.1	0.3	0.3	0.7
Other insurance expense (benefit)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	0.1	0.3	0.4	0.8
Warrant
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	5.0	1.5	13.3	10.3
Warrant | Sales and marketing
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	0.0	0.0	0.0	8.8
Warrant | Other insurance expense (benefit)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 5.0	$ 1.5	$ 13.3	$ 1.5

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SHARE-BASED COMPENSATION - Share-based Compensation Expense (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 4.7	$ 7.8	$ 12.4	$ 21.8
Restricted stock unit expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	4.4	7.4	11.4	20.5
Performance-based restricted stock unit expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.1	0.0	0.1	0.0
Stock option expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.2	0.4	0.9	1.3
Loss and loss adjustment expenses
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.2	0.2	0.5	0.6
Sales and marketing
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.1	0.3	0.3	0.7
Other insurance expense (benefit)
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.1	0.3	0.4	0.8
Technology and development
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.9	1.1	2.4	3.1
General and administrative
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 3.4	$ 5.9	$ 8.8	$ 16.6

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SHARE-BASED COMPENSATION - Performance Stock Units (Details) - Performance-based RSUs - $ / shares shares in Millions	3 Months Ended	9 Months Ended
	Sep. 30, 2023	Sep. 30, 2023
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)	0.4	0.4
Tranche 1
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock price (in dollars per share)		$ 16.76
Granted (in shares)		0.0
Granted (in dollars per share)		$ 7.69
Tranche 2
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock price (in dollars per share)		$ 25.14
Granted (in shares)		0.1
Granted (in dollars per share)		$ 6.70
Tranche 3
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock price (in dollars per share)		$ 33.52
Granted (in shares)		0.1
Granted (in dollars per share)		$ 5.87
Tranche 4
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock price (in dollars per share)		$ 41.90
Granted (in shares)		0.2
Granted (in dollars per share)		$ 5.10

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SHARE-BASED COMPENSATION - RSU Activity (Details) - Restricted stock unit expense $ / shares in Units, shares in Millions, $ in Millions	9 Months Ended
	Sep. 30, 2023 USD ($) $ / shares shares
Number of Shares
Beginning balance (in shares) | shares	1.1
Granted (in shares) | shares	1.6
Vested (in shares) | shares	(0.5)
Forfeited, expired or canceled (in shares) | shares	(0.2)
Ending balance (in shares) | shares	2.0
Weighted-Average Grant Date Fair Value per Share
Beginning balance (in dollars per share) | $ / shares	$ 51.81
Granted (in dollars per share) | $ / shares	6.62
Vested (in dollars per share) | $ / shares	50.44
Forfeited, expired or canceled (in dollars per share) | $ / shares	53.75
Ending balance (in dollars per share) | $ / shares	$ 15.79
Aggregate Intrinsic Value
Beginning balance | $	$ 5.0
Vested | $	2.8
Ending balance | $	$ 18.9

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SHARE-BASED COMPENSATION - Option Activity (Details) $ / shares in Units, shares in Millions, $ in Millions	9 Months Ended	12 Months Ended
	Sep. 30, 2023 USD ($) $ / shares shares	Dec. 31, 2022 USD ($) $ / shares shares
Number of Shares
Outstanding, beginning balance (in shares) | shares	0.2
Granted (in shares) | shares	0.0
Exercised (in shares) | shares	0.0
Forfeited, expired or canceled (in shares) | shares	(0.1)
Outstanding, ending balance (in shares) | shares	0.1	0.2
Weighted-Average Exercise Price
Outstanding, beginning balance (in dollars per share) | $ / shares	$ 38.15
Granted (in dollars per share) | $ / shares	8.94
Exercised (in dollars per share) | $ / shares	0
Forfeited, expired and canceled (in dollars per share) | $ / shares	44.86
Outstanding, ending balance (in dollars per share) | $ / shares	$ 33.74	$ 38.15
Outstanding, weighted-average remaining contractual term (in years)	4 years 6 months 10 days	5 years 7 months 17 days
Outstanding, aggregate intrinsic value | $	$ 0.5	$ 0.2
Exercised, aggregate intrinsic value | $	$ 0.0

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OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	$ 214.4	$ 381.3	$ 277.1	$ 536.4
Other comprehensive loss	(0.7)	(2.3)	(0.8)	(7.3)
Ending balance	177.1	321.8	177.1	321.8
Change in net unrealized gains (losses) on investments:
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	(5.9)	(4.6)	(5.8)	0.4
Other comprehensive loss before reclassifications	(0.7)	(2.3)	(0.8)	(7.4)
Net realized losses on investments reclassified from AOCI to net loss	0.0	0.0	0.0	0.1
Other comprehensive loss	(0.7)	(2.3)	(0.8)	(7.3)
Ending balance	$ (6.6)	$ (6.9)	$ (6.6)	$ (6.9)

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LOSS PER SHARE - Schedule of Basic and Diluted Loss per Share (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Earnings Per Share [Abstract]
Net loss	$ (45.8)	$ (66.4)	$ (123.4)	$ (239.4)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)	14.5	14.1	14.4	14.0
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)	14.5	14.1	14.4	14.0
Loss per common share: basic (both Class A and B) (in dollars per share)	$ (3.16)	$ (4.71)	$ (8.57)	$ (17.10)
Loss per common share: diluted (both Class A and B) (in dollars per share)	$ (3.16)	$ (4.71)	$ (8.57)	$ (17.10)

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LOSS PER SHARE - Schedule of Anti-Dilutive Securities (Details) - shares shares in Millions	9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	10.7	10.1
Options to purchase common stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	0.1	0.2
Nonvested shares subject to repurchase
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	0.1	0.1
Restricted stock units and performance-based restricted stock units
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	2.0	1.3
Redeemable convertible preferred stock (as converted to common stock)
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	0.8	0.8
Warrants to purchase common stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	7.7	7.7

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GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Effects of Reinsurance [Line Items]
Total	$ 224.2	$ 150.7	$ 503.9	$ 478.0
Texas
Effects of Reinsurance [Line Items]
Total	36.8	26.2	80.1	89.5
Georgia
Effects of Reinsurance [Line Items]
Total	26.3	15.0	56.0	48.8
Colorado
Effects of Reinsurance [Line Items]
Total	15.3	10.3	37.8	30.8
Pennsylvania
Effects of Reinsurance [Line Items]
Total	12.1	9.1	29.0	26.8
South Carolina
Effects of Reinsurance [Line Items]
Total	11.8	4.5	28.6	16.4
Utah
Effects of Reinsurance [Line Items]
Total	8.3	8.0	22.9	24.1
Arizona
Effects of Reinsurance [Line Items]
Total	11.0	4.3	21.7	13.3
Ohio
Effects of Reinsurance [Line Items]
Total	8.4	3.9	16.9	11.8
Oklahoma
Effects of Reinsurance [Line Items]
Total	7.2	5.2	16.7	16.1
Missouri
Effects of Reinsurance [Line Items]
Total	8.7	4.3	16.1	14.2
All others states
Effects of Reinsurance [Line Items]
Total	$ 78.3	$ 59.9	$ 178.1	$ 186.2
Geographic Concentration Risk | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	100.00%	100.00%	100.00%	100.00%
Geographic Concentration Risk | Gross Written Premiums | Texas
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	16.40%	17.40%	15.90%	18.70%
Geographic Concentration Risk | Gross Written Premiums | Georgia
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	11.70%	10.00%	11.10%	10.20%
Geographic Concentration Risk | Gross Written Premiums | Colorado
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	6.80%	6.80%	7.50%	6.40%
Geographic Concentration Risk | Gross Written Premiums | Pennsylvania
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	5.40%	6.00%	5.80%	5.60%
Geographic Concentration Risk | Gross Written Premiums | South Carolina
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	5.30%	3.00%	5.70%	3.40%
Geographic Concentration Risk | Gross Written Premiums | Utah
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	3.70%	5.30%	4.50%	5.00%
Geographic Concentration Risk | Gross Written Premiums | Arizona
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	4.90%	2.90%	4.30%	2.80%
Geographic Concentration Risk | Gross Written Premiums | Ohio
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	3.70%	2.60%	3.40%	2.50%
Geographic Concentration Risk | Gross Written Premiums | Oklahoma
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	3.20%	3.50%	3.30%	3.40%
Geographic Concentration Risk | Gross Written Premiums | Missouri
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	3.90%	2.90%	3.20%	3.00%
Geographic Concentration Risk | Gross Written Premiums | All others states
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	35.00%	39.60%	35.30%	39.00%