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Condensed Consolidated Statements of Cash Flows - USD ($)
$ in Thousands
9 Months Ended
Sep. 30, 2021
Sep. 30, 2020
Cash flows from operating activities:    
Net loss $ (86,497) $ (33,548)
Adjustments to reconcile net loss to net cash used in operating activities    
Depreciation and amortization 10,787 5,021
Loss on sale and impairment of long-lived assets 202 807
Gain on extinguishment of debt (5,110) (1,077)
Loss on remeasurement of debt   924
Gain on divestiture of businesses   (1,442)
Loss on remeasurement of warrants 17,521 1,214
Loss (gain) on remeasurement of contingent consideration (380) 1,500
Loss on remeasurement of earnout liability 15,388  
Stock-based compensation 29,361 1,541
Amortization of premium/accretion of discount, net 941  
Net realized losses on investments 45  
Interest expense (non-cash) 67 4,899
Other   106
Other (1,379)  
Change in operating assets and liabilities, net of acquisitions and divestitures    
Accounts receivable (5,424) (1,056)
Reinsurance balance due (33,097)  
Prepaid expenses and other current assets 90 208
Long-term insurance commissions receivable (3,794) (1,947)
Accounts payable (23,284) 3,723
Accrued expenses and other current liabilities 3,031 1,575
Losses and loss adjustment expense reserves 1,892  
Other insurance liabilities, current 5,085  
Deferred revenue 42,948 3,109
Refundable customer deposits (2,441) (2,641)
Deferred income tax benefit (8,153)  
Other 484 69
Net cash used in operating activities (41,717) (17,015)
Cash flows from investing activities:    
Purchases of property and equipment (588) (121)
Capitalized internal use software development costs (2,629) (2,113)
Purchases of short-term and long-term investments (19,126)  
Maturities, sales of short-term and long-term investments 16,367  
Acquisitions, net of cash acquired (178,681) (1,618)
Net cash used in investing activities (184,657) (3,852)
Cash flows from financing activities:    
Proceeds from debt issuance, net of fees 413,537 61,190
Repayments of principal and related fees (42,965) (42,858)
Proceeds from issuance of redeemable convertible preferred stock, net of fees   4,714
Capped call transactions (42,330)  
Proceeds from exercises of warrants 126,772  
Proceeds from exercises of stock options 3,516 76
Income tax withholdings paid upon vesting of restricted stock units (23,778)  
Deferred offering costs   (1,255)
Repurchase of stock   (42)
Net cash provided by financing activities 434,752 21,825
Net change in cash, cash equivalents, and restricted cash 208,378 958
Cash, cash equivalents, and restricted cash, beginning of period 207,453 7,179
Cash, cash equivalents, and restricted cash end of period 415,831 8,137
Supplemental disclosures    
Cash paid for interest 2,675 4,344
Reduction of earnout liability due to a vesting event 25,815  
Non-cash consideration for acquisitions 42,229 1,829
Payable for capped call transactions $ 10,583  
Debt discount for warrants issued (non-cash)   1,215
Cancelation of a convertible promissory note on divestiture of a business   2,724
Conversion of debt to redeemable convertible preferred stock (non-cash)   1,436
Capital contribution from a shareholder   $ 300