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Condensed Consolidated Statements of Cash Flows - USD ($)
$ in Thousands
6 Months Ended
Jun. 30, 2023
Jun. 30, 2022
Cash flows from operating activities:    
Net loss $ (125,703) $ (36,610)
Adjustments to reconcile net loss to net cash used in operating activities    
Depreciation and amortization 12,229 12,899
Provision for doubtful accounts 48,955 207
Impairment loss on intangible assets and goodwill 57,232  
Gain on extinguishment of debt (81,354)  
Gain on remeasurement of private warrant liability (360) (14,267)
Loss (gain) on remeasurement of contingent consideration (2,810) 4,686
Loss (gain) on remeasurement of earnout liability and derivatives 2,950 (13,766)
Stock-based compensation 13,298 15,556
Interest expense (non-cash) 9,828 2,339
Other 805 1,916
Change in operating assets and liabilities, net of acquisitions and divestitures    
Accounts receivable 1,030 (7,483)
Reinsurance balance due (21,651) (40,835)
Prepaid expenses and other current assets (9,656) (7,090)
Accounts payable 2,929 (4,226)
Accrued expenses and other current liabilities (10,906) 1,005
Losses and loss adjustment expense reserves 65,077 26,945
Other insurance liabilities, current 51,139 21,492
Deferred revenue (13,491) 38,167
Refundable customer deposits (8,061) (457)
Long-term insurance commissions receivable (1,237) (2,940)
Other 980 (1,694)
Net cash used in operating activities (8,777) (4,156)
Cash flows from investing activities:    
Purchases of property and equipment (672) (1,539)
Capitalized internal use software development costs (4,735) (3,496)
Purchases of short-term and long-term investments (23,602) (13,561)
Maturities, sales of short-term and long-term investments 23,033 12,241
Acquisitions, net of cash acquired (1,974) (32,049)
Net cash used in investing activities (7,950) (38,404)
Cash flows from financing activities:    
Proceeds from line of credit   1,000
Proceeds from advance funding 316 10,690
Repayments of advance funding (2,683) (8,840)
Proceeds from issuance of debt 116,667  
Repayments of principal (10,150) (150)
Cash paid for debt issuance costs (4,610)  
Proceeds from exercises of stock options 8 692
Income tax withholdings paid upon vesting of restricted stock units (883) (1,922)
Proceeds from sale of common stock 191  
Payments of acquisition-related contingent consideration (276) (1,625)
Repurchase of stock (5,608)  
Net cash provided by (used in) financing activities 92,972 (155)
Net change in cash, cash equivalents, and restricted cash 76,245 (42,715)
Cash, cash equivalents, and restricted cash, beginning of period 228,605 324,792
Cash, cash equivalents, and restricted cash end of period 304,850 282,077
Supplemental schedule of non-cash financing activities    
Non-cash reduction in advanced funding arrangement obligations 7,848  
Supplemental disclosures    
Cash paid for interest 2,276 1,587
Income tax refunds received $ 2,300  
Non-cash consideration for acquisitions   21,607
Cash payable for acquisition   $ 5,000