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Condensed Consolidated Statements of Cash Flows (Unaudited) - USD ($)
$ in Thousands
6 Months Ended
Jun. 30, 2025
Jun. 30, 2024
Cash flows from operating activities:    
Net income (loss) $ 11,983 $ (77,685)
Adjustments to reconcile net income (loss) to net cash provided by (used in) operating activities    
Depreciation and amortization 11,411 12,519
Provision for doubtful accounts 2,768 (481)
Gain on extinguishment of debt (34) (4,891)
Loss on divestiture of business 0 5,331
Change in fair value of private warrant liability 3,610 (1,026)
Change in fair value of derivatives (19,526) 6,724
Stock-based compensation 12,910 12,473
Non-cash interest expense 17,515 17,313
Gain on settlement of contingent consideration 0 (14,930)
Other operating activities (829) (2,182)
Change in operating assets and liabilities, net of acquisitions and divestitures    
Accounts receivable (2,039) (1,548)
Reinsurance balance due 46,760 (20,042)
Deferred policy acquisition costs 7,939 10,895
Accounts payable (336) (5,627)
Accrued expenses and other current liabilities (4,440) (7,827)
Losses and loss adjustment expense reserves 283 37,717
Other insurance liabilities, current (9,182) 35,615
Deferred revenue (51,528) (25,693)
Refundable customer deposits 869 (3,594)
Other assets and liabilities, net (3,743) 9,434
Net cash provided by (used in) operating activities 24,391 (17,505)
Cash flows from investing activities:    
Purchases of property and equipment (271) (86)
Capitalized internal use software development costs (6,756) (5,458)
Purchases of short-term and long-term investments (75,423) (19,193)
Maturities, sales of short-term and long-term investments 57,181 22,631
Proceeds from sale of business 0 10,870
Net cash provided by (used in) investing activities (25,269) 8,764
Cash flows from financing activities:    
Proceeds from issuance of debt 51,000 0
Repayments of principal (55,858) (3,150)
Cash paid for debt issuance costs (2,206) 0
Other financing activities (947) 24
Net cash used in financing activities (8,011) (3,126)
Net change in cash, cash equivalents, and restricted cash and cash equivalents (8,889) (11,867)
Cash, cash equivalents, and restricted cash and cash equivalents at beginning of period 196,782 297,232
Cash, cash equivalents, and restricted cash and cash equivalents at end of period 187,893 285,365
Supplemental schedule of non-cash investing and financing activities    
Non-cash reduction of convertible notes, net 14,514 5,000
Non-cash reduction in advance funding arrangement obligations 0 94
Supplemental disclosures    
Cash paid for interest 12,021 12,056
Income taxes paid $ 349 $ 538