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Condensed Consolidated Statements of Cash Flows - USD ($)
$ in Thousands
9 Months Ended
Sep. 30, 2022
Sep. 30, 2021
Cash flows from operating activities:    
Net loss $ (118,564) $ (86,497)
Adjustments to reconcile net loss to net cash used in operating activities    
Depreciation and amortization 21,574 10,787
Amortization of operating lease right-of-use assets 1,621 1,298
Impairment loss on intangible assets and goodwill 57,057  
Loss on sale and impairment of property, equipment, and software 200 202
Gain on extinguishment of debt   (5,110)
Loss (gain) on remeasurement of private warrant liability (14,391) 17,521
Loss (gain) on remeasurement of contingent consideration 5,251 (380)
Loss (gain) on remeasurement of earnout liability (13,809) 15,388
Stock-based compensation 20,645 29,361
Amortization of investment premium/accretion of discount, net 1,702 941
Net realized losses on investments 187 45
Interest expense (non-cash) 2,287 67
Other 480  
Other   (1,379)
Change in operating assets and liabilities, net of acquisitions and divestitures    
Accounts receivable (8,639) (5,424)
Reinsurance balance due (75,571) (33,097)
Prepaid expenses and other current assets (6,297) 90
Accounts payable (248) (23,284)
Accrued expenses and other current liabilities (8,001) 3,031
Losses and loss adjustment expense reserves 38,349 1,892
Other insurance liabilities, current 15,921 5,085
Deferred revenue 71,600 42,948
Refundable customer deposits 4,593 (2,441)
Deferred income tax benefit   (8,153)
Long-term insurance commissions receivable (4,409) (3,794)
Operating lease liabilities, non-current (1,936) (1,469)
Other (2,410) 655
Net cash used in operating activities (12,808) (41,717)
Cash flows from investing activities:    
Purchases of property and equipment (1,986) (588)
Capitalized internal use software development costs (5,803) (2,629)
Purchases of short-term and long-term investments (19,446) (19,126)
Maturities, sales of short-term and long-term investments 17,794 16,367
Acquisitions, net of cash acquired (37,003) (178,681)
Net cash used in investing activities (46,444) (184,657)
Cash flows from financing activities:    
Proceeds from debt issuance, net of fees 15,000 413,537
Repayments of principal and related fees (150) (42,965)
Capped call transactions   (42,330)
Proceeds from exercises of warrants   126,772
Proceeds from exercises of stock options 1,108 3,516
Income tax withholdings paid upon vesting of restricted stock units (2,879) (23,778)
Payments of acquisition-related contingent consideration (1,625)  
Net cash provided by financing activities 11,454 434,752
Net change in cash, cash equivalents, and restricted cash (47,798) 208,378
Cash, cash equivalents, and restricted cash, beginning of period 324,792 207,453
Cash, cash equivalents, and restricted cash end of period 276,994 415,831
Supplemental disclosures    
Cash paid for interest 3,181 2,675
Non-cash consideration for acquisitions $ 14,952 42,229
Reduction of earnout liability due to a vesting event   25,815
Payable for capped call transaction   $ 10,583