BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Additional Information (Details)			1 Months Ended	12 Months Ended
	Aug. 12, 2022 shares	Jan. 26, 2022 USD ($)	Mar. 31, 2022 USD ($)	Dec. 31, 2022 USD ($) segment $ / shares shares	Dec. 31, 2021 USD ($) shares	Dec. 31, 2020 USD ($)	Oct. 31, 2022 USD ($)	Aug. 31, 2022 $ / shares	Aug. 15, 2022 $ / shares	Oct. 31, 2021 tranche shares	Oct. 01, 2021 tranche
Asset Acquisition [Line Items]
Write off of prepaid marketing expense				$ 10,200,000
Shares converted (in shares) | shares	18
Conversion of stock, shares issued (in shares) | shares	1
Common stock, par value (in dollars per share) | $ / shares								$ 0.0001	$ 0.0001
Exercise price of warrants (in dollars per share) | $ / shares				$ 0.0001
Purchases of indefinite-lived intangible assets and transaction costs				$ 1,300,000	$ 0	$ 8,900,000
Impairment of intangible assets				$ 0	0	0
Number of reportable segments | segment				1
Allowance for premiums receivable				$ 2,800,000	5,400,000
Bad debt expense				17,400,000	20,900,000	23,600,000
Deferred policy acquisition cost				6,700,000	2,800,000
Amortization of deferred acquisition costs				22,500,000	26,400,000	17,100,000
Allowance for credit loss				200,000	200,000
Valuation allowance				$ 322,300,000	255,000,000.0
Amortization period				5 years
Amortization expense				$ 5,000,000	3,700,000	2,400,000
Depreciation expense				$ 2,100,000	$ 4,600,000	$ 3,100,000
Preferred stock, issued (in shares) | shares				14,100,000	14,100,000
Term Loan | Secured debt
Asset Acquisition [Line Items]
Debt amount		$ 300,000,000
Debt instrument, term		5 years
Amended Term Loan B | Line of Credit | Revolving Loan
Asset Acquisition [Line Items]
Maximum borrowing capacity							$ 100,000,000
Internet Domain Names
Asset Acquisition [Line Items]
Purchase of assets			$ 1,300,000
Carvana
Asset Acquisition [Line Items]
Preferred stock, issued (in shares) | shares										14,100,000
Number of tranches | tranche										8	8
Investment agreement, term of agreement										5 years
Stock option expense
Asset Acquisition [Line Items]
Exercisable period				10 years
Vesting period				4 years
Service and performance period				4 years
Stock option expense | Tranche 1
Asset Acquisition [Line Items]
Vesting period				1 year
Vesting percentage				25.00%
Stock option expense | Tranche 2
Asset Acquisition [Line Items]
Vesting period				3 years
Vesting percentage				2.00%
Restricted stock unit expense
Asset Acquisition [Line Items]
Vesting period				4 years
Restricted stock unit expense | Tranche 1
Asset Acquisition [Line Items]
Vesting period				1 year
Vesting percentage				25.00%
Restricted stock unit expense | Tranche 2
Asset Acquisition [Line Items]
Vesting period				3 years
Vesting percentage				2.00%
Other Certain RSUs 1
Asset Acquisition [Line Items]
Vesting period				4 years
Other Certain RSUs 1 | Tranche 1
Asset Acquisition [Line Items]
Vesting period				1 year
Vesting percentage				25.00%
Other Certain RSUs 2
Asset Acquisition [Line Items]
Vesting period				4 years
Other Certain RSUs 3
Asset Acquisition [Line Items]
Vesting period				1 year
Computers
Asset Acquisition [Line Items]
Useful life				3 years
Furniture
Asset Acquisition [Line Items]
Useful life				5 years
Root Property & Casualty
Asset Acquisition [Line Items]
Purchases of indefinite-lived intangible assets and transaction costs				$ 8,900,000	$ 8,900,000
Series A Convertible Preferred Stock
Asset Acquisition [Line Items]
Exercise price of warrants (in dollars per share) | $ / shares									$ 162.00