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Intangible Assets and Goodwill (Details) - USD ($)
$ in Millions
 3 Months Ended 9 Months Ended
Sep. 30, 2023
Sep. 30, 2022
Sep. 30, 2023
Sep. 30, 2022
Dec. 31, 2022
Finite-Lived Intangible Assets [Line Items]          
Accumulated Amortization $ (15.8)   $ (15.8)   $ (12.5)
Indefinite-lived Intangible Assets [Line Items]          
Gross Carrying Amount 39.4   39.4   39.4
Accumulated Amortization (15.8)   (15.8)   (12.5)
Net Carrying Amount 23.6   23.6   26.9
Amortization expense related to intangible assets 1.1 $ 1.1 3.3 $ 4.2  
Goodwill impairment charge 1.2 $ 53.5   $ 53.5  
State licenses and domain name          
Indefinite-lived Intangible Assets [Line Items]          
Net Carrying Amount $ 10.5   $ 10.5   10.5
Agency and carrier relationships          
Finite-Lived Intangible Assets [Line Items]          
Weighted- Average Useful Life Remaining (in years) 5 years 2 months 12 days   5 years 2 months 12 days    
Gross Carrying Amount $ 13.5   $ 13.5   13.5
Accumulated Amortization (4.7)   (4.7)   (3.4)
Net Carrying Amount 8.8   8.8   10.1
Indefinite-lived Intangible Assets [Line Items]          
Accumulated Amortization $ (4.7)   $ (4.7)   (3.4)
Customer relationships          
Finite-Lived Intangible Assets [Line Items]          
Weighted- Average Useful Life Remaining (in years) 1 year 7 months 6 days   1 year 7 months 6 days    
Gross Carrying Amount $ 13.7   $ 13.7   13.7
Accumulated Amortization (10.3)   (10.3)   (8.5)
Net Carrying Amount 3.4   3.4   5.2
Indefinite-lived Intangible Assets [Line Items]          
Accumulated Amortization $ (10.3)   $ (10.3)   (8.5)
Other          
Finite-Lived Intangible Assets [Line Items]          
Weighted- Average Useful Life Remaining (in years) 5 years 9 months 18 days   5 years 9 months 18 days    
Gross Carrying Amount $ 1.7   $ 1.7   1.7
Accumulated Amortization (0.8)   (0.8)   (0.6)
Net Carrying Amount 0.9   0.9   1.1
Indefinite-lived Intangible Assets [Line Items]          
Accumulated Amortization $ (0.8)   $ (0.8)   $ (0.6)