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CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - UNAUDITED - USD ($)
$ in Millions
 6 Months Ended
Jun. 30, 2021
Jun. 30, 2020
Cash flows from operating activities:    
Net loss $ (278.2) $ (144.5)
Adjustments to reconcile net loss to net cash used in operating activities:    
Share-based compensation 7.2 1.1
Tender offer 0.0 25.1
Depreciation and amortization 7.2 7.1
Bad debt expense 9.4 11.2
Warrants fair value adjustment 0.0 2.4
Payment-in-kind interest expense 5.8 4.5
Net realized gains on investments (2.4) (0.1)
Changes in operating assets and liabilities:    
Premiums receivable (39.5) (18.6)
Reinsurance recoverable (17.2) (17.4)
Prepaid reinsurance premiums 1.3 (23.4)
Other assets 3.3 (3.7)
Losses and loss adjustment expenses reserves 35.3 49.6
Unearned premiums 38.7 10.7
Reinsurance premiums payable (20.5) 33.9
Accounts payable and accrued expenses 23.0 (0.1)
Other liabilities 0.1 (0.2)
Net cash used in operating activities (226.5) (62.4)
Cash flows from investing activities:    
Purchases of investments (6.8) (118.8)
Proceeds from maturities, call and pay downs of investments 23.9 17.7
Sales of investments 70.2 5.7
Capitalization of internally developed software (3.2) (2.4)
Purchases of fixed assets (1.5) (1.5)
Net cash provided by (used in) investing activities 82.6 (99.3)
Cash flows from financing activities:    
Proceeds from exercise of stock options and restricted stock units, net of tax proceeds/(withholding) 4.7 0.3
Purchase of treasury stock 0.0 (0.2)
Debt issuance costs 0.0 (0.1)
Repayments of long-term debt (0.5) (13.0)
Net cash provided by (used in) financing activities 4.2 (13.0)
Net decrease in cash, cash equivalents and restricted cash (139.7) (174.7)
Cash, cash equivalents and restricted cash at beginning of period 1,113.8 416.6
Cash, cash equivalents and restricted cash at end of period $ 974.1 $ 241.9