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Consolidated Statements of Cash Flows - USD ($)
$ in Millions
 12 Months Ended
Dec. 31, 2023
Dec. 31, 2022
Cash flows from operating activities:    
Net Loss $ (263.0) $ (326.5)
Adjustments to reconcile net loss to net cash used in operating activities:    
Depreciation and amortization 19.8 15.2
Stock–based compensation expense 57.5 61.9
Other changes in fair value (1.5) (4.0)
Change in fair value of contingent consideration liability 6.0 4.1
Impairment charges 2.9 53.5
Other non-cash items (7.4) (3.0)
Changes in assets and liabilities:    
Accounts receivable, net (38.0) (50.9)
Reinsurance recoverable on paid and unpaid losses and LAE 5.0 (19.4)
Ceding commissions receivable (28.0) (4.2)
Prepaid reinsurance premiums (25.7) (78.3)
Other assets 6.2 8.9
Provision for commission 19.7 (7.3)
Accrued expenses and other liabilities (5.5) 19.6
Loss and loss adjustment expense reserves 28.7 33.0
Unearned premiums 77.9 88.2
Reinsurance premiums payable 53.0 47.7
Net cash used in operating activities (92.4) (161.5)
Cash flows from investing activities:    
Capitalized internal use software costs (17.1) (14.8)
Purchases of property and equipment (29.6) (4.9)
Purchases of fixed maturities (55.3) (88.8)
Maturities of fixed maturities 15.6 10.2
Sales of fixed maturities 3.2 6.5
Purchases of short-term investments (354.3) (704.2)
Maturities of short-term investments 471.6 391.4
Sales of short-term investments 26.7 0.7
Other (3.2) (2.0)
Net cash provided by (used in) investing activities 57.6 (405.9)
Cash flows from financing activities:    
Taxes paid related to net share settlement of equity awards (4.7) (3.9)
Proceeds from issuance of common stock 2.8 4.1
Share repurchases under program (1.8) 0.0
Payments of contingent consideration (1.3) (1.7)
Acquisitions of noncontrolling interests (3.2) 0.0
Distributions to noncontrolling interests and other (6.4) (5.3)
Net cash used in financing activities (14.6) (6.8)
Net decrease in cash, cash equivalents, and restricted cash (49.4) (574.2)
Cash, cash equivalents, and restricted cash at the beginning of the period 244.5 818.7
Cash, cash equivalents, and restricted cash at the end of the period $ 195.1 $ 244.5