Root (ROOT) 10-Q 2 Aug 23 2023 Q2 Quarterly report Financial data

COVER PAGE

COVER PAGE - shares shares in Millions	6 Months Ended
	Jun. 30, 2023	Jul. 27, 2023
Entity Listings [Line Items]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Jun. 30, 2023
Document Transition Report	false
Entity File Number	001-39658
Entity Registrant Name	ROOT, INC.
Entity Incorporation, State or Country Code	DE
Entity Tax Identification Number	84-2717903
Entity Address, Address Line One	80 E. Rich Street
Entity Address, Address Line Two	Suite 500
Entity Address, City or Town	Columbus
Entity Address, State or Province	OH
Entity Address, Postal Zip Code	43215
City Area Code	866
Local Phone Number	980-9431
Title of 12(b) Security	Class A common stock,$0.0001 par value per share
Trading Symbol	ROOT
Security Exchange Name	NASDAQ
Entity Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Accelerated Filer
Entity Small Business	true
Entity Emerging Growth Company	false
Entity Shell Company	false
Amendment Flag	false
Document Fiscal Year Focus	2023
Document Fiscal Period Focus	Q2
Entity Central Index Key	0001788882
Current Fiscal Year End Date	--12-31
Class A Shares
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		9.5
Class B Shares
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		5

CONDENSED CONSOLIDATED BALANCE

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED - USD ($) $ in Millions	Jun. 30, 2023	Dec. 31, 2022
Investments:
Fixed maturities available-for-sale, at fair value (amortized cost: $165.9 and $134.2 at June 30, 2023 and December 31, 2022, respectively)	$ 160	$ 128.4
Short-term investments (amortized cost: $2.7 and $0.4 at June 30, 2023 and December 31, 2022, respectively)	2.7	0.4
Other investments	4.4	4.4
Total investments	167.1	133.2
Cash and cash equivalents	628	762.1
Restricted cash	1	1
Premiums receivable, net of allowance of $2.2 and $2.8 at June 30, 2023 and December 31, 2022, respectively	127.6	111.9
Reinsurance recoverable and receivable, net of allowance of $0.2 at June 30, 2023 and December 31, 2022	130.2	148.8
Prepaid reinsurance premiums	73.7	74.2
Other assets	67.3	81.7
Total assets	1,194.9	1,312.9
Liabilities:
Loss and loss adjustment expense reserves	246.5	287.4
Unearned premiums	154.6	136.5
Long-term debt and warrants	297.4	295.4
Reinsurance premiums payable	90.4	119.8
Accounts payable and accrued expenses	37.8	39.7
Other liabilities	41.8	45
Total liabilities	868.5	923.8
Commitments and Contingencies (Note 11)
Redeemable convertible preferred stock, $0.0001 par value, 100.0 shares authorized, 14.1 shares issued and outstanding at June 30, 2023 and December 31, 2022 (liquidation preference of $126.5)	112	112
Stockholders’ equity:
Additional paid-in capital	1,865.7	1,850.7
Accumulated other comprehensive loss	(5.9)	(5.8)
Accumulated loss	(1,645.4)	(1,567.8)
Total stockholders’ equity	214.4	277.1
Total liabilities, redeemable convertible preferred stock and stockholders’ equity	1,194.9	1,312.9
Class A Shares
Stockholders’ equity:
Common stock, value	0	0
Class B Shares
Stockholders’ equity:
Common stock, value	$ 0	$ 0

CONDENSED CONSOLIDATED BALANC_2

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED (Parenthetical) - USD ($) shares in Millions, $ in Millions	Jun. 30, 2023	Dec. 31, 2022
Amortized cost, fixed maturities	$ 165.9	$ 134.2
Amortized cost, short term investments	2.7	0.4
Allowance for premiums receivable	2.2	2.8
Allowance for credit loss	$ 0.2	$ 0.2
Preferred stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Preferred stock, shares authorized (in shares)	100	100
Preferred stock, shares issued (in shares)	14.1	14.1
Preferred stock, shares outstanding (in shares)	14.1	14.1
Preferred stock, liquidation preference	$ 126.5	$ 126.5
Class A Shares
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	1,000	1,000
Common stock, shares issued (in shares)	9.4	9.2
Common stock, shares outstanding (in shares)	9.4	9.2
Class B Shares
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	269	269
Common stock, shares issued (in shares)	5	5
Common stock, shares outstanding (in shares)	5	5

CONDENSED CONSOLIDATED STATEMEN

CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS - UNAUDITED - USD ($) shares in Millions, $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Revenues:
Net premiums earned	$ 63.9	$ 74.7	$ 123.9	$ 153
Net investment income	6.8	0.7	13.5	1.3
Net realized (losses) gains on investments	0	(0.1)	0	1.1
Fee income	3.8	4.4	7	9.3
Other income	0.3	0.7	0.5	1.1
Total revenues	74.8	80.4	144.9	165.8
Operating expenses:
Loss and loss adjustment expenses	59.5	95.7	122.8	192.4
Sales and marketing	6.1	21.4	9.7	36.7
Other insurance expense (benefit)	2.6	(7.8)	3.9	(6.8)
Technology and development	11.1	17.9	21.3	31.8
General and administrative	20.7	39.5	42.2	70
Total operating expenses	100	166.7	199.9	324.1
Operating loss	(25.2)	(86.3)	(55)	(158.3)
Interest expense	(11.5)	(9.2)	(22.6)	(14.7)
Loss before income tax expense	(36.7)	(95.5)	(77.6)	(173)
Income tax expense	0	0	0	0
Net loss	(36.7)	(95.5)	(77.6)	(173)
Other comprehensive loss:
Changes in net unrealized losses on investments	(1.2)	(1.3)	(0.1)	(5)
Comprehensive loss	$ (37.9)	$ (96.8)	$ (77.7)	$ (178)
Loss per common share: basic (both Class A and B) (in dollars per share)	$ (2.55)	$ (6.77)	$ (5.43)	$ (12.36)
Loss per common share: diluted (both Class A and B) (in dollars per share)	$ (2.55)	$ (6.77)	$ (5.43)	$ (12.36)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)	14.4	14.1	14.3	14
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)	14.4	14.1	14.3	14

CONDENSED CONSOLIDATED STATEM_2

CONDENSED CONSOLIDATED STATEMENTS OF REDEEMABLE CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS’ EQUITY - UNAUDITED - USD ($) shares in Millions, $ in Millions	Total	Class A Shares	Class B Shares	Class A and Class B Common Stock	Class A and Class B Common Stock Class A Shares	Class A and Class B Common Stock Class B Shares	Additional Paid-in Capital	Accumulated Other Comprehensive Loss	Accumulated Loss
Beginning balance (in shares) at Dec. 31, 2021	14.1
Beginning balance at Dec. 31, 2021	$ 112
Ending balance (in shares) at Jun. 30, 2022	14.1
Ending balance at Jun. 30, 2022	$ 112
Beginning balance (in shares) at Dec. 31, 2021					7.9	6.1
Beginning balance at Dec. 31, 2021	536.4			$ 0			$ 1,806.1	$ 0.4	$ (1,270.1)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(173)								(173)
Other comprehensive loss	(5)							(5)
Conversion of Class B to Class A (in shares)					0.9	(0.9)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)					0.1
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	0.4						0.4
Reclassification of early-exercised stock options from liabilities	0.1						0.1
Common stock—share-based compensation expense	14						14
Warrant compensation expense	8.8						8.8
Warrant issuance costs	(1)						(1)
Term Loan warrants issued	0.6						0.6
Ending balance (in shares) at Jun. 30, 2022					8.9	5.2
Ending balance at Jun. 30, 2022	$ 381.3			0			1,829	(4.6)	(1,443.1)
Beginning balance (in shares) at Mar. 31, 2022	14.1
Beginning balance at Mar. 31, 2022	$ 112
Ending balance (in shares) at Jun. 30, 2022	14.1
Ending balance at Jun. 30, 2022	$ 112
Beginning balance (in shares) at Mar. 31, 2022					8.6	5.5
Beginning balance at Mar. 31, 2022	467.6			0			1,818.5	(3.3)	(1,347.6)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(95.5)								(95.5)
Other comprehensive loss	(1.3)							(1.3)
Conversion of Class B to Class A (in shares)					0.3	(0.3)
Common stock—share-based compensation expense	7.4						7.4
Warrant compensation expense	3.5						3.5
Warrant issuance costs	(0.4)						(0.4)
Ending balance (in shares) at Jun. 30, 2022					8.9	5.2
Ending balance at Jun. 30, 2022	$ 381.3			0			1,829	(4.6)	(1,443.1)
Beginning balance (in shares) at Dec. 31, 2022	14.1
Beginning balance at Dec. 31, 2022	$ 112
Ending balance (in shares) at Jun. 30, 2023	14.1
Ending balance at Jun. 30, 2023	$ 112
Beginning balance (in shares) at Dec. 31, 2022		9.2	5		9.2	5
Beginning balance at Dec. 31, 2022	277.1			0			1,850.7	(5.8)	(1,567.8)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(77.6)								(77.6)
Other comprehensive loss	$ (0.1)							(0.1)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)	0				0.2
Common stock—share-based compensation expense	$ 7.7						7.7
Warrant compensation expense	8.3						8.3
Warrant issuance costs	(1)						(1)
Ending balance (in shares) at Jun. 30, 2023		9.4	5		9.4	5
Ending balance at Jun. 30, 2023	$ 214.4			0			1,865.7	(5.9)	(1,645.4)
Beginning balance (in shares) at Mar. 31, 2023	14.1
Beginning balance at Mar. 31, 2023	$ 112
Ending balance (in shares) at Jun. 30, 2023	14.1
Ending balance at Jun. 30, 2023	$ 112
Beginning balance (in shares) at Mar. 31, 2023					9.2	5
Beginning balance at Mar. 31, 2023	243.7			0			1,857.1	(4.7)	(1,608.7)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(36.7)								(36.7)
Other comprehensive loss	(1.2)							(1.2)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)					0.2
Common stock—share-based compensation expense	5.2						5.2
Warrant compensation expense	3.9						3.9
Warrant issuance costs	(0.5)						(0.5)
Ending balance (in shares) at Jun. 30, 2023		9.4	5		9.4	5
Ending balance at Jun. 30, 2023	$ 214.4			$ 0			$ 1,865.7	$ (5.9)	$ (1,645.4)

CONDENSED CONSOLIDATED STATEM_3

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - UNAUDITED - USD ($) $ in Millions	6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022
Cash flows from operating activities:
Net loss	$ (77.6)	$ (173)
Adjustments to reconcile net loss to net cash used in operating activities:
Share-based compensation	7.7	14
Warrant compensation expense	8.3	8.8
Depreciation and amortization	5.5	6.6
Bad debt expense	5	8.9
Net realized gains on investments	0	(1.1)
Changes in operating assets and liabilities:
Premiums receivable	(20.7)	7
Reinsurance recoverable and receivable	18.6	(3.1)
Prepaid reinsurance premiums	0.5	9
Other assets	14.6	(3.8)
Losses and loss adjustment expenses reserves	(40.9)	(7.5)
Unearned premiums	18.1	(18.2)
Reinsurance premiums payable	(29.4)	22.4
Accounts payable and accrued expenses	(0.8)	14.3
Other liabilities	(3.2)	10.8
Net cash used in operating activities	(94.3)	(104.9)
Cash flows from investing activities:
Purchases of investments	(48.9)	(9)
Proceeds from maturities, call and pay downs of investments	14.8	11.6
Sales of investments	0.2	2.2
Capitalization of internally developed software	(5.1)	(5.3)
Purchases of fixed assets	(0.2)	0
Purchases of indefinite-lived intangible assets and transaction costs	0	(1.3)
Net cash used in investing activities	(39.2)	(1.8)
Cash flows from financing activities:
Proceeds from exercise of stock options and restricted stock units, net of tax (withholding)/proceeds	(0.6)
Proceeds from exercise of stock options and restricted stock units, net of tax (withholding)/proceeds		0.3
Proceeds from issuance of debt and related warrants, net of issuance costs	0	286
Net cash (used in) provided by financing activities	(0.6)	286.3
Net (decrease) increase in cash, cash equivalents and restricted cash	(134.1)	179.6
Cash, cash equivalents and restricted cash at beginning of period	763.1	707
Cash, cash equivalents and restricted cash at end of period	$ 629	$ 886.6

NATURE OF BUSINESS

NATURE OF BUSINESS	6 Months Ended
	Jun. 30, 2023
Organization, Consolidation and Presentation of Financial Statements [Abstract]
NATURE OF BUSINESS	NATURE OF BUSINESSRoot, Inc. is a holding company which, directly or indirectly, maintains 100% ownership of each of its subsidiaries, including, among others, Root Insurance Company, an Ohio-domiciled insurance company; Root Property & Casualty Insurance Company, which as of July 1, 2023 was redomiciled from Delaware to Ohio; and Root Reinsurance Company, Ltd., a Cayman Islands-domiciled reinsurance company, together with Root, Inc., “we,” “us” or “our.” We were formed in 2015 and began writing personal auto insurance in July 2016. We are a technology company operating primarily a direct-to-consumer model with the majority of our personal insurance customers acquired through mobile applications and our embedded platform. We offer auto and renters insurance products underwritten by Root Insurance Company and Root Property & Casualty Insurance Company.

BASIS OF PRESENTATION AND SUMMA

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES	6 Months Ended
	Jun. 30, 2023
Accounting Policies [Abstract]
BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES	BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES Basis of Presentation —In our opinion, all adjustments necessary for a fair presentation of the condensed consolidated financial statements have been included. All such adjustments are of a normal and recurring nature. These condensed consolidated financial statements are unaudited and, accordingly, should be read in conjunction with the consolidated financial statements and related notes included in the Annual Report on Form 10-K for the year ended December 31, 2022 filed with the Securities and Exchange Commission, or SEC, on February 22, 2023, or the 2022 10-K. Basis of Consolidation —The unaudited condensed consolidated financial statements include the accounts of Root, Inc. and its subsidiaries, all of which are wholly owned. These financial statements have been prepared in accordance with accounting principles generally accepted in the United States, or GAAP. All intercompany accounts and transactions have been eliminated. Use of Estimates —The preparation of the unaudited condensed consolidated financial statements requires management to make certain estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the unaudited condensed consolidated financial statements and the reported amounts of revenue and expenses during the reporting period. Actual results could differ from those estimates. Significant estimates reflected in our unaudited condensed consolidated financial statements include, but are not limited to, reserves for loss and loss adjustment expense, or LAE, allowance for expected credit losses on premium receivables and valuation allowances for income taxes. Revision of Previously Issued Financial Statements —During the fourth quarter of 2022, we identified errors in our first, second and third quarter financial statements for 2022 and revised the quarterly presentation of certain sales and marketing and general and administrative expenses on our condensed consolidated statements of operations and comprehensive loss related to the purported misappropriation of funds by a senior marketing employee. The errors did not impact periods prior to 2022. In accordance with SEC Staff Accounting Bulletin, or SAB, No. 99, Materiality, and SAB No. 108, Considering the Effects of Prior Year Misstatements when Quantifying Misstatements in Current Year Financial Statements , we assessed the materiality of these errors on our financial statements and concluded the errors were not material to the unaudited interim financial statements for the three and six months ended June 30, 2022. The following tables present the effect of the revision on the condensed consolidated statements of operations and comprehensive loss for the three and six months ended June 30, 2022, condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity and condensed consolidated statement of cash flows as of and for the six months ended June 30, 2022. Three Months Ended June 30, 2022 (unaudited) Six Months Ended June 30, 2022 (unaudited) As reported Adjustments As Corrected As reported Adjustments As Corrected (in millions, except per share amounts) Condensed consolidated statements of operations and comprehensive loss: Sales and marketing $ 25.4 $ (4.0) $ 21.4 $ 40.1 $ (3.4) $ 36.7 General and administrative 29.9 9.6 39.5 59.9 10.1 70.0 Total operating expenses 161.1 5.6 166.7 317.4 6.7 324.1 Operating loss (80.7) (5.6) (86.3) (151.6) (6.7) (158.3) Loss before income tax expense (89.9) (5.6) (95.5) (166.3) (6.7) (173.0) Net loss (89.9) (5.6) (95.5) (166.3) (6.7) (173.0) Comprehensive loss $ (91.2) $ (5.6) $ (96.8) $ (171.3) $ (6.7) $ (178.0) Weighted-average common shares outstanding: basic and diluted (both Class A and B) 14.1 14.1 14.0 14.0 Loss per common share: basic and diluted (both Class A and B) $ (6.38) $ (6.77) $ (11.88) $ (12.36) As of June 30, 2022 (unaudited) As reported Adjustments As Corrected (in millions) Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity: Accumulated loss $ (1,436.4) $ (6.7) $ (1,443.1) Total stockholders’ equity $ 388.0 $ (6.7) $ 381.3 Six Months Ended June 30, 2022 (unaudited) As reported Adjustments As Corrected (in millions) Condensed consolidated statement of cash flows: Net loss $ (166.3) $ (6.7) $ (173.0) Other assets (10.5) 6.7 (3.8) Net cash used in operating activities $ (104.9) $ — $ (104.9) Reverse Stock Split— In August 2022, an authorized subcommittee of our board of directors approved a reverse stock split of our Class A and Class B common stock at a ratio of 1-for-18. On August 12, 2022, we filed a Certificate of Amendment to our Amended and Restated Certificate of Incorporation to effect a 1-for-18 reverse stock split of our Class A and Class B common stock. As a result of the reverse stock split, every 18 shares of our issued or outstanding pre-reverse split common stock of each class were combined into one share of common stock of such class. No fractional shares were issued upon the reverse stock split. On August 15, 2022, our Class A common stock began trading on a split-adjusted basis on the Nasdaq Stock Market. Accordingly, all historical per share data, number of shares outstanding and other common stock equivalents for the periods presented in the accompanying condensed consolidated financial statements and notes thereto have been adjusted retroactively, where applicable, to reflect the reverse stock split. Cash, Cash Equivalents and Restricted Cash —The following table provides a reconciliation of cash, cash equivalents and restricted cash reported within the condensed consolidated balance sheets that sum to the total of the same such amount in the condensed consolidated statements of cash flows: As of June 30, December 31, 2023 2022 (dollars in millions) Cash and cash equivalents $ 628.0 $ 762.1 Restricted cash 1.0 1.0 Total cash, cash equivalents and restricted cash shown in the condensed consolidated statements of cash flows $ 629.0 $ 763.1

INVESTMENTS

INVESTMENTS	6 Months Ended
	Jun. 30, 2023
Investments, Debt and Equity Securities [Abstract]
INVESTMENTS	INVESTMENTS The amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities at June 30, 2023 and December 31, 2022 are as follows: June 30, 2023 Amortized Cost Allowance for Expected Credit Losses Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 15.2 $ — $ — $ (0.3) $ 14.9 Municipal securities 25.6 — — (1.2) 24.4 Corporate debt securities 70.0 — — (2.7) 67.3 Residential mortgage-backed securities 10.6 — — (0.4) 10.2 Commercial mortgage backed securities 29.2 — — (1.2) 28.0 Other debt obligations 15.3 — — (0.1) 15.2 Total fixed maturities 165.9 — — (5.9) 160.0 Short-term investments 2.7 — — — 2.7 Total $ 168.6 $ — $ — $ (5.9) $ 162.7 December 31, 2022 Amortized Cost Allowance for Expected Credit Losses Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 11.3 $ — $ — $ (0.3) $ 11.0 Municipal securities 21.4 — — (1.2) 20.2 Corporate debt securities 60.5 — — (2.7) 57.8 Residential mortgage-backed securities 5.5 — — (0.3) 5.2 Commercial mortgage backed securities 24.4 — — (1.2) 23.2 Other debt obligations 11.1 — 0.1 (0.2) 11.0 Total fixed maturities 134.2 — 0.1 (5.9) 128.4 Short-term investments 0.4 — — — 0.4 Total $ 134.6 $ — $ 0.1 $ (5.9) $ 128.8 Management reviewed the available-for-sale securities at each balance sheet date to consider whether it was necessary to recognize a credit loss as of June 30, 2023 and December 31, 2022. We do not intend to sell the investments and it is not more likely than not that we will be required to sell the security before recovery. Management concluded that the available-for-sale securities’ unrealized losses were due to non-credit related factors and, therefore, there was no allowance for credit loss as of June 30, 2023 and December 31, 2022. The following tables reflect the gross unrealized losses and fair value of short-term investments and available-for-sale fixed maturity securities, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at June 30, 2023 and December 31, 2022: June 30, 2023 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 9.1 $ (0.1) $ 5.3 $ (0.2) $ 14.4 $ (0.3) Municipal securities 7.9 (0.1) 14.9 (1.1) 22.8 (1.2) Corporate debt securities 28.3 (0.6) 37.9 (2.1) 66.2 (2.7) Residential mortgage-backed securities 6.7 (0.1) 2.0 (0.3) 8.7 (0.4) Commercial mortgage-backed securities 13.4 (0.3) 14.5 (0.9) 27.9 (1.2) Other debt obligations 10.8 (0.1) 1.5 — 12.3 (0.1) Total fixed maturities 76.2 (1.3) 76.1 (4.6) 152.3 (5.9) Short-term investments 1.0 — — — 1.0 — Total $ 77.2 $ (1.3) $ 76.1 $ (4.6) $ 153.3 $ (5.9) December 31, 2022 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 6.9 $ (0.1) $ 4.1 $ (0.2) $ 11.0 $ (0.3) Municipal securities 11.5 (0.5) 8.2 (0.7) 19.7 (1.2) Corporate debt securities 45.3 (1.6) 11.5 (1.1) 56.8 (2.7) Residential mortgage-backed securities 2.2 — 1.9 (0.3) 4.1 (0.3) Commercial mortgage-backed securities 18.3 (0.8) 4.6 (0.4) 22.9 (1.2) Other debt obligations 6.8 (0.2) — — 6.8 (0.2) Total fixed maturities 91.0 (3.2) 30.3 (2.7) 121.3 (5.9) Short-term investments 0.1 — — — 0.1 — Total $ 91.1 $ (3.2) $ 30.3 $ (2.7) $ 121.4 $ (5.9) Other Investments As of June 30, 2023 and December 31, 2022, other investments related to our private equity investments were $4.4 million. There were no realized gains or losses for the three and six months ended June 30, 2023. We recognized zero and $1.2 million of realized gains for the three and six months ended June 30, 2022, respectively. We recorded the gain on sale of our private equity investments within net realized (losses) gains on investments in our condensed consolidated statements of operations and comprehensive loss. There were no unrealized gains and losses or impairment losses recognized on private equity investments for the three and six months ended June 30, 2023 and 2022. The following table reflects the gross and net realized gains and losses on short-term investments, available-for-sale fixed maturities and other investments that have been included in the condensed consolidated statements of operations and comprehensive loss for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Realized gains on investments $ — $ — $ — $ 1.2 Realized losses on investments — (0.1) — (0.1) Net realized (losses) gains on investments $ — $ (0.1) $ — $ 1.1 The following table sets forth the amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities by contractual maturity at June 30, 2023: June 30, 2023 Amortized Cost Fair Value (dollars in millions) Due in one year or less $ 34.1 $ 33.5 Due after one year through five years 100.0 96.2 Due five years through 10 years 19.1 18.4 Due after 10 years 15.4 14.6 Total $ 168.6 $ 162.7 The following table sets forth the components of net investment income for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Interest on bonds $ 1.0 $ 0.5 $ 1.9 $ 1.1 Interest on deposits and cash equivalents 6.0 0.4 11.9 0.6 Total 7.0 0.9 13.8 1.7 Investment expense (0.2) (0.2) (0.3) (0.4) Net investment income $ 6.8 $ 0.7 $ 13.5 $ 1.3 The following tables summarize the credit ratings of short-term investments and available-for-sale fixed maturity securities at June 30, 2023 and December 31, 2022: June 30, 2023 Amortized Cost Fair Value % of Total (dollars in millions) S&P Global rating or equivalent AAA $ 81.8 $ 79.1 48.6 % AA+, AA, AA-, A-1 26.7 25.8 15.9 A+, A, A- 45.0 43.0 26.4 BBB+, BBB, BBB- 15.1 14.8 9.1 Total $ 168.6 $ 162.7 100.0 % December 31, 2022 Amortized Cost Fair Value % of Total (dollars in millions) S&P Global rating or equivalent AAA $ 62.5 $ 59.9 46.5 % AA+, AA, AA-, A-1 19.9 19.1 14.8 A+, A, A- 38.4 36.5 28.3 BBB+, BBB, BBB- 13.8 13.3 10.4 Total $ 134.6 $ 128.8 100.0 %

FAIR VALUE OF FINANCIAL INSTRUM

FAIR VALUE OF FINANCIAL INSTRUMENTS	6 Months Ended
	Jun. 30, 2023
Fair Value Disclosures [Abstract]
FAIR VALUE OF FINANCIAL INSTRUMENTS	FAIR VALUE OF FINANCIAL INSTRUMENTS The following tables provide information about our financial assets measured and reported at fair value as of June 30, 2023 and December 31, 2022: June 30, 2023 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 13.1 $ 1.8 $ — $ 14.9 Municipal securities — 24.4 — 24.4 Corporate debt securities — 67.3 — 67.3 Residential mortgage-backed securities — 10.2 — 10.2 Commercial mortgage-backed securities — 28.0 — 28.0 Other debt obligations — 15.2 — 15.2 Total fixed maturities 13.1 146.9 — 160.0 Short-term investments 2.4 0.3 — 2.7 Cash equivalents 404.3 — — 404.3 Total assets at fair value $ 419.8 $ 147.2 $ — $ 567.0 December 31, 2022 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 9.2 $ 1.8 $ — $ 11.0 Municipal securities — 20.2 — 20.2 Corporate debt securities — 57.8 — 57.8 Residential mortgage-backed securities — 5.2 — 5.2 Commercial mortgage-backed securities — 23.2 — 23.2 Other debt obligations — 11.0 — 11.0 Total fixed maturities 9.2 119.2 — 128.4 Short-term investments — 0.4 — 0.4 Cash equivalents 487.3 — — 487.3 Total assets at fair value $ 496.5 $ 119.6 $ — $ 616.1 We estimate the fair value of all our different classes of Level 2 fixed maturities and short-term investments by using quoted prices from a combination of an independent pricing vendor or broker/dealer, pricing models, quoted prices of securities with similar characteristics or discounted cash flows. All significant inputs were observable in the active markets. Private Equity Investments Measured at Fair Value on a Non-Recurring Basis Private equity investments that have been remeasured during the period due to an observable event or impairment are classified within Level 3 in the fair value hierarchy because we estimate the value based on valuation methods which may include a combination of the observable transaction price at the transaction date and other unobservable inputs including volatility, rights, and obligations of the investments we hold. See Note 3, “Investments,” for further information on our private equity investments. Fair Value of Long-Term Debt The carrying amount of long-term debt is recorded at the unpaid balance, net of discount and debt issuance costs. The fair value of outstanding long-term debt is classified within Level 2 of the fair value hierarchy. The fair value is based on a model referencing observable interest rates and spreads to project and discount cash flows to present value. As of June 30, 2023 and December 31, 2022, the carrying amounts and fair values of these financial instruments were as follows: Carrying Amount as of June 30, 2023 Estimated Fair Value as of June 30, 2023 Carrying Amount as of December 31, 2022 Estimated Fair Value as of December 31, 2022 (dollars in millions) Long-term debt $ 297.4 $ 310.2 $ 295.4 $ 309.7

LOSS AND LOSS ADJUSTMENT EXPENS

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES	6 Months Ended
	Jun. 30, 2023
Insurance [Abstract]
LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES	LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES The following provides a reconciliation of the beginning and ending reserve balances for loss and LAE, net of reinsurance: Six Months Ended June 30, 2023 2022 (dollars in millions) Gross loss and LAE reserves, January 1 $ 287.4 $ 320.2 Reinsurance recoverable on unpaid losses (76.4) (79.5) Net loss and LAE reserves, January 1 211.0 240.7 Net incurred loss and LAE related to: Current year 123.6 191.9 Prior years (0.8) 0.5 Total incurred 122.8 192.4 Net paid loss and LAE related to: Current year 58.7 89.8 Prior years 99.0 96.0 Total paid 157.7 185.8 Net loss and LAE reserves, June 30 176.1 247.3 Plus reinsurance recoverable on unpaid losses 70.4 65.4 Gross loss and LAE reserves, June 30 $ 246.5 $ 312.7

REINSURANCE

REINSURANCE	6 Months Ended
	Jun. 30, 2023
Insurance [Abstract]
REINSURANCE	REINSURANCE The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Premiums written: Direct $ 128.1 $ 130.8 $ 251.9 $ 304.3 Assumed 16.9 9.3 27.8 23.0 Ceded (67.2) (81.1) (137.1) (183.5) Net premiums written $ 77.8 $ 59.0 $ 142.6 $ 143.8 Premiums earned: Direct $ 120.2 $ 159.3 $ 240.3 $ 324.8 Assumed 11.3 11.5 21.3 20.7 Ceded (67.6) (96.1) (137.7) (192.5) Net premiums earned $ 63.9 $ 74.7 $ 123.9 $ 153.0 Losses and LAE incurred: Direct $ 90.5 $ 152.2 $ 190.3 $ 303.9 Assumed 8.7 13.2 16.4 24.4 Ceded (39.7) (69.7) (83.9) (135.9) Net losses and LAE incurred $ 59.5 $ 95.7 $ 122.8 $ 192.4 In the event that all or any of the reinsuring companies might be unable to meet their obligations under existing reinsurance agreements, we would be liable to the policyholder for such defaulted amounts. Gross premiums written by state is as follows for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 Amount % of Total Amount % of Total Amount % of Total Amount % of Total (dollars in millions) State: Texas $ 23.8 16.4 % $ 26.0 18.6 % $ 43.3 15.5 % $ 63.3 19.3 % Georgia 15.8 10.9 15.0 10.7 29.7 10.6 33.8 10.3 Colorado 11.9 8.2 9.8 7.0 22.5 8.0 20.5 6.3 Pennsylvania 7.6 5.2 7.7 5.5 16.9 6.0 17.7 5.4 South Carolina 10.6 7.3 4.8 3.4 16.8 6.0 11.9 3.6 Utah 7.4 5.1 7.1 5.1 14.6 5.2 16.1 4.9 Arizona 6.0 4.1 3.7 2.6 10.7 3.8 9.0 2.7 Louisiana 4.3 3.0 8.2 5.9 9.8 3.5 18.9 5.8 Oklahoma 4.8 3.3 4.6 3.3 9.5 3.4 10.9 3.3 Nevada 4.5 3.1 7.0 5.0 8.9 3.2 15.7 4.8 All others states 48.3 33.4 46.2 32.9 97.0 34.8 109.5 33.6 Total $ 145.0 100.0 % $ 140.1 100.0 % $ 279.7 100.0 % $ 327.3 100.0 %

LONG-TERM DEBT

LONG-TERM DEBT	6 Months Ended
	Jun. 30, 2023
Debt Disclosure [Abstract]
LONG-TERM DEBT	LONG-TERM DEBT In January 2022, we entered into a $300.0 million five-year term loan, or Term Loan, with the principal amount due and payable upon maturity on January 27, 2027. Interest is payable quarterly and is determined on a floating interest rate currently calculated on the Secured Overnight Financing Rate, or SOFR, with a 1.0% floor, plus 9.0%, plus 0.26161% per annum through June 30, 2023, after which the interest rate will be calculated on the SOFR with a 1.0% floor, plus 9.0%. The following summarizes the carrying value of long-term debt as of June 30, 2023 and December 31, 2022: June 30, 2023 December 31, 2022 (dollars in millions) Term Loan $ 300.0 $ 300.0 Accrued interest payable 7.8 7.3 Unamortized discount, debt issuance costs and warrants (10.4) (11.9) Total $ 297.4 $ 295.4

INCOME TAXES

INCOME TAXES	6 Months Ended
	Jun. 30, 2023
Income Tax Disclosure [Abstract]
INCOME TAXES	INCOME TAXES The consolidated effective tax rate was zero for the three and six months ended June 30, 2023 and 2022. The difference between these rates and the U.S. federal income tax rate of 21% was primarily due to a full valuation allowance on our U.S. deferred tax assets. As of June 30, 2023 and December 31, 2022, we did not have any unrecognized tax benefits for uncertain tax positions and had no interest or penalties related to uncertain tax positions.

RESTRUCTURING COSTS

RESTRUCTURING COSTS	6 Months Ended
	Jun. 30, 2023
Restructuring and Related Activities [Abstract]
RESTRUCTURING COSTS	RESTRUCTURING COSTS In 2022, we conducted strategic initiatives to reduce operating costs, improve efficiency, and increase focus on our strategic priorities. These initiatives resulted in restructuring actions that included a reduction in workforce levels, contract terminations, and in certain instances, a reduction in office space. These restructuring actions include the following costs: Employee costs —consist of severance, benefits, share-based compensation, and employee compensation expense dependent upon continuous employment for certain employees and related employee costs. Real estate exit costs —consist of real estate exit costs primarily related to accelerated amortization of right-of-use assets, leasehold improvements and furniture and fixtures. Other costs —primarily consist of contract termination costs incurred as part of our efforts to improve efficiency and reduce operating costs and accelerated expense for software that no longer has economic benefit. As of June 30, 2023, we expect to incur approximately $3.6 million of employee compensation expense, dependent upon continuous employment for certain employees, to be recognized ratably through the fourth quarter of 2023. We expect a cash expenditure related to these employee compensation costs in January 2024. As of June 30, 2023, except as discussed above, we do not expect to incur any additional material expenditures in future periods related to restructuring actions that have occurred. The following table displays restructuring costs recorded in general and administrative expenses on the condensed consolidated statements of operations and comprehensive loss: Three Months Ended June 30, Six Months Ended June 30, Cumulative Incurred Through June 30, 2023 2023 2022 2023 2022 (dollars in millions) Restructuring costs: Employee costs $ 1.8 $ — $ 4.1 $ 5.6 $ 19.6 Real estate exit costs — 0.6 — 2.1 2.1 Other costs 0.1 — 3.4 0.7 4.4 Total restructuring costs $ 1.9 $ 0.6 $ 7.5 $ 8.4 $ 26.1 The following table displays a rollforward of the accrual for restructuring costs recorded in other liabilities on the condensed consolidated balance sheets: Employee costs Other costs Total liability (dollars in millions) Restructuring activity: Restructuring liability as of January 1, 2023 $ 3.1 $ 0.1 $ 3.2 Expense incurred 3.7 3.4 7.1 Payments (2.0) (3.5) (5.5) Restructuring liability as of June 30, 2023 $ 4.8 $ — $ 4.8

SHARE-BASED COMPENSATION

SHARE-BASED COMPENSATION	6 Months Ended
	Jun. 30, 2023
Share-Based Payment Arrangement [Abstract]
SHARE-BASED COMPENSATION	SHARE-BASED COMPENSATION Warrants In October 2021, we issued Carvana eight tranches of warrants, comprised of three tranches of “short-term warrants” and five tranches of “long-term warrants,” with the opportunity to purchase a maximum of 7.2 million shares of Class A common stock. As of June 30, 2023, we determined the remaining unvested short-term warrants were probable of vesting. Under that scenario, it is not a possible outcome for the long-term warrants to also vest, so they are considered not probable of vesting. We recognized warrant compensation expense related to these equity-classified warrants based on progress toward completing the integrated automobile insurance solution for Carvana’s online buying platform, or the Integrated Platform and policies originating through the Integrated Platform. All of these warrants are out-of-the-money and therefore have no intrinsic value as of June 30, 2023. The following table displays warrant compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Warrant compensation expense: Sales and marketing $ — $ 3.5 $ — $ 8.8 Other insurance expense (benefit) 3.9 — 8.3 — Total warrant compensation expense $ 3.9 $ 3.5 $ 8.3 $ 8.8 As of June 30, 2023, there was $12.8 million of unrecognized compensation cost related to warrants. The remaining costs are expected to be recognized over a period of approximately two years. Employee Share-Based Compensation We maintain an equity incentive plan, or the Plan, for the issuance and grant of equity awards (restricted stock, restricted stock units, or RSUs, and incentive and nonqualified stock options) to our officers, directors, employees and certain advisors. As of June 30, 2023, we had 2.0 million common shares authorized and available for issuance under the Plan. The following table displays share-based compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Share-based compensation expense: Loss and loss adjustment expenses $ 0.2 $ 0.2 $ 0.3 $ 0.4 Sales and marketing 0.1 0.3 0.2 0.4 Other insurance expense (benefit) 0.2 0.3 0.3 0.5 Technology and development 0.8 1.3 1.5 2.0 General and administrative 3.9 5.3 5.4 10.7 Total share-based compensation expense $ 5.2 $ 7.4 $ 7.7 $ 14.0 The following table provides total share-based compensation expense by type of award: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Share-based compensation expense: Restricted stock unit expense $ 4.9 $ 7.0 $ 7.0 $ 13.1 Stock option expense 0.3 0.4 0.7 0.9 Total share-based compensation expense $ 5.2 $ 7.4 $ 7.7 $ 14.0 As of June 30, 2023, there was $1.5 million and $26.0 million of unrecognized compensation cost related to unvested stock options and RSUs, respectively. The remaining costs are expected to be recognized over a period of approximately three years for unvested stock options and four years for RSUs. Restricted Stock Units A summary of RSU activity for the six months ended June 30, 2023 is as follows: Six Months Ended June 30, 2023 Restricted Stock Units Number of Shares Weighted-Average Aggregate Intrinsic Value (in millions, except per share amounts) Nonvested at January 1, 2023 1.1 $ 51.81 $ 5.0 Granted 0.8 5.56 Vested (0.4) 50.86 2.0 Forfeited, expired or canceled (0.2) 57.36 Nonvested at June 30, 2023 1.3 $ 23.16 $ 11.2 Stock Options A summary of option activity for the six months ended June 30, 2023 is as follows: Six Months Ended June 30, 2023 Options Number of Shares Weighted-Average Exercise Price Weighted-Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in millions, except exercise price and term amounts) Outstanding and exercisable at January 1, 2023 0.2 $ 38.15 5.63 $ 0.2 Granted — 8.94 Exercised — — — Forfeited, expired or canceled (0.1) 44.87 Outstanding and exercisable at June 30, 2023 0.1 $ 33.75 4.80 $ 0.4

COMMITMENTS AND CONTINGENCIES

COMMITMENTS AND CONTINGENCIES	6 Months Ended
	Jun. 30, 2023
Commitments and Contingencies Disclosure [Abstract]
COMMITMENTS AND CONTINGENCIES	COMMITMENTS AND CONTINGENCIES From time to time, we are party to litigation and legal proceedings relating to our business operations. Except as disclosed below, we do not believe that we are party to any current or pending legal action that could reasonably be expected to have a material adverse effect on our financial condition or results of operations and cash flow. On February 9, 2023, a purported class action complaint was filed against the Company’s subsidiary, Root Insurance Company, in the U.S. District Court for the Middle District of Louisiana (Case No. 3:23-cv-00089-JWD-RLB) by an individual on her behalf and further claiming to represent a putative class of insureds. The complaint alleged that Root Insurance Company breached its insurance contract and violated specific provisions of Louisiana law in settling her vehicle total loss claim. The complaint sought damages to include payment of alleged benefits owed under the policy, in addition to pre- and post-judgment interest, statutory penalties, attorneys fees and costs, and injunctive relief on behalf of the named plaintiff and the putative class members. This matter was settled for an immaterial amount and dismissed with prejudice on July 20, 2023. On December 19, 2022, a purported class action complaint was filed against the Company’s subsidiary, Root Insurance Company, in the U.S. District Court for the Western District of Texas (Case No. 1:22-cv-01328-LY) by an individual on her behalf and further claiming to represent a putative class of insureds. The complaint alleges that Root Insurance Company breached its insurance contract and violated specific provisions of the Texas Prompt Payment of Claims Act for an alleged failure to include sales tax in total loss vehicle settlements. The complaint seeks damages to include payment of alleged benefits owed under the policy, in addition to pre- and post-judgment interest and attorneys fees on behalf of the named plaintiff and the putative class members. Root Insurance Company has moved to dismiss the claims set forth in the complaint. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is in its early stages. Therefore, at this time, we cannot predict the outcome or estimate the likelihood or magnitude of our possible or potential loss contingency. On June 27, 2022, a verified shareholder derivative complaint was filed against certain of the Company’s current and former officers and directors in the U.S. District Court for the District of Delaware (Case No. 1:22-cv-00865). The Company was named as a nominal defendant. The complaint alleges that defendants made false or misleading statements and omissions of purportedly material fact, in violation of Section 10(b) of the Securities Exchange Act of 1934, or the Exchange Act, and Rule 10b-5 thereunder, breached their fiduciary duties and/or aided and abetted the breach of fiduciary duties, were unjustly enriched, wasted corporate assets, and are liable under Section 11(f) of the Securities Act of 1933, or the Securities Act, in connection with and following the Company’s initial public offering. The complaint seeks unspecified damages. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is currently stayed pending final resolution of the below matter and, at this time, we are unable to predict the outcome and we cannot estimate the likelihood or magnitude of our possible or potential loss contingency. On March 19, 2021, a purported class action complaint was filed against the Company and certain of its current and former officers and directors in the U.S. District Court for the Southern District of Ohio (Case No. 2:21-cv-01197) on behalf of certain Root shareholders. The complaint alleges that defendants made false or misleading statements and omissions of purportedly material fact, in violation of Sections 10(b) and 20(a) of the Exchange Act and Rule 10b-5 thereunder, and of Sections 11 and 15 of the Securities Act in connection with and following the Company’s initial public offering. The complaint seeks unspecified damages. The defendants’ motion to dismiss the claims set forth in the complaint was granted and the lawsuit was dismissed with prejudice on March 31, 2023, which dismissal has been appealed. The Company believes that the claims in this lawsuit are without merit and intends to defend against them vigorously. The lawsuit is in the early stages and, at this time, we are unable to predict the outcome and we cannot estimate the likelihood or magnitude of our possible or potential loss contingency. We are contingently liable for possible future assessments under regulatory requirements for insolvencies and impairments of unaffiliated insurance companies.

OTHER COMPREHENSIVE LOSS AND AC

OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME	6 Months Ended
	Jun. 30, 2023
Equity [Abstract]
OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME	OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME The following table presents the changes in our accumulated other comprehensive (loss) income, or AOCI, for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Beginning balance $ (4.7) $ (3.3) $ (5.8) $ 0.4 Other comprehensive loss before reclassifications (1.2) (1.4) (0.1) (5.1) Net realized gains on investments reclassified from AOCI to net loss — 0.1 — 0.1 Other comprehensive loss (1.2) (1.3) (0.1) (5.0) Ending balance $ (5.9) $ (4.6) $ (5.9) $ (4.6)

LOSS PER SHARE

LOSS PER SHARE	6 Months Ended
	Jun. 30, 2023
Earnings Per Share [Abstract]
LOSS PER SHARE	LOSS PER SHARE The following table displays the computation of basic and diluted loss per share for both Class A and Class B common stock for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (in millions, except per share amounts) Net loss $ (36.7) $ (95.5) $ (77.6) $ (173.0) Weighted-average common shares outstanding: basic and diluted (both Class A and B) 14.4 14.1 14.3 14.0 Loss per common share: basic and diluted (both Class A and B) $ (2.55) $ (6.77) $ (5.43) $ (12.36) We excluded the following potentially dilutive common stock equivalents, presented based on amounts outstanding at each period end, from the computation of diluted loss per share attributable to common shareholders for the periods indicated because including them would have had an anti-dilutive effect: As of June 30, 2023 2022 (in millions) Options to purchase common stock 0.1 0.2 Nonvested shares subject to repurchase 0.1 0.1 Restricted stock units 1.3 1.3 Redeemable convertible preferred stock (as converted to common stock) 0.8 0.8 Warrants to purchase common stock 7.6 7.7 Total 9.9 10.1

GEOGRAPHICAL BREAKDOWN OF GROSS

GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN	6 Months Ended
	Jun. 30, 2023
Insurance [Abstract]
GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN	REINSURANCE The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Premiums written: Direct $ 128.1 $ 130.8 $ 251.9 $ 304.3 Assumed 16.9 9.3 27.8 23.0 Ceded (67.2) (81.1) (137.1) (183.5) Net premiums written $ 77.8 $ 59.0 $ 142.6 $ 143.8 Premiums earned: Direct $ 120.2 $ 159.3 $ 240.3 $ 324.8 Assumed 11.3 11.5 21.3 20.7 Ceded (67.6) (96.1) (137.7) (192.5) Net premiums earned $ 63.9 $ 74.7 $ 123.9 $ 153.0 Losses and LAE incurred: Direct $ 90.5 $ 152.2 $ 190.3 $ 303.9 Assumed 8.7 13.2 16.4 24.4 Ceded (39.7) (69.7) (83.9) (135.9) Net losses and LAE incurred $ 59.5 $ 95.7 $ 122.8 $ 192.4 In the event that all or any of the reinsuring companies might be unable to meet their obligations under existing reinsurance agreements, we would be liable to the policyholder for such defaulted amounts. Gross premiums written by state is as follows for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 Amount % of Total Amount % of Total Amount % of Total Amount % of Total (dollars in millions) State: Texas $ 23.8 16.4 % $ 26.0 18.6 % $ 43.3 15.5 % $ 63.3 19.3 % Georgia 15.8 10.9 15.0 10.7 29.7 10.6 33.8 10.3 Colorado 11.9 8.2 9.8 7.0 22.5 8.0 20.5 6.3 Pennsylvania 7.6 5.2 7.7 5.5 16.9 6.0 17.7 5.4 South Carolina 10.6 7.3 4.8 3.4 16.8 6.0 11.9 3.6 Utah 7.4 5.1 7.1 5.1 14.6 5.2 16.1 4.9 Arizona 6.0 4.1 3.7 2.6 10.7 3.8 9.0 2.7 Louisiana 4.3 3.0 8.2 5.9 9.8 3.5 18.9 5.8 Oklahoma 4.8 3.3 4.6 3.3 9.5 3.4 10.9 3.3 Nevada 4.5 3.1 7.0 5.0 8.9 3.2 15.7 4.8 All others states 48.3 33.4 46.2 32.9 97.0 34.8 109.5 33.6 Total $ 145.0 100.0 % $ 140.1 100.0 % $ 279.7 100.0 % $ 327.3 100.0 %

BASIS OF PRESENTATION AND SUM_2

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Policies)	6 Months Ended
	Jun. 30, 2023
Accounting Policies [Abstract]
Basis of Presentation	Basis of Presentation —In our opinion, all adjustments necessary for a fair presentation of the condensed consolidated financial statements have been included. All such adjustments are of a normal and recurring nature. These condensed consolidated financial statements are unaudited and, accordingly, should be read in conjunction with the consolidated financial statements and related notes included in the Annual Report on Form 10-K for the year ended December 31, 2022 filed with the Securities and Exchange Commission, or SEC, on February 22, 2023, or the 2022 10-K.
Basis of Consolidation	Basis of Consolidation —The unaudited condensed consolidated financial statements include the accounts of Root, Inc. and its subsidiaries, all of which are wholly owned. These financial statements have been prepared in accordance with accounting principles generally accepted in the United States, or GAAP. All intercompany accounts and transactions have been eliminated.
Use of Estimates	Use of Estimates —The preparation of the unaudited condensed consolidated financial statements requires management to make certain estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the unaudited condensed consolidated financial statements and the reported amounts of revenue and expenses during the reporting period. Actual results could differ from those estimates. Significant estimates reflected in our unaudited condensed consolidated financial statements include, but are not limited to, reserves for loss and loss adjustment expense, or LAE, allowance for expected credit losses on premium receivables and valuation allowances for income taxes.

BASIS OF PRESENTATION AND SUM_3

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Tables)	6 Months Ended
	Jun. 30, 2023
Accounting Policies [Abstract]
Schedule of Error Corrections and Prior Period Adjustments	The following tables present the effect of the revision on the condensed consolidated statements of operations and comprehensive loss for the three and six months ended June 30, 2022, condensed consolidated statement of redeemable convertible preferred stock and stockholders’ equity and condensed consolidated statement of cash flows as of and for the six months ended June 30, 2022. Three Months Ended June 30, 2022 (unaudited) Six Months Ended June 30, 2022 (unaudited) As reported Adjustments As Corrected As reported Adjustments As Corrected (in millions, except per share amounts) Condensed consolidated statements of operations and comprehensive loss: Sales and marketing $ 25.4 $ (4.0) $ 21.4 $ 40.1 $ (3.4) $ 36.7 General and administrative 29.9 9.6 39.5 59.9 10.1 70.0 Total operating expenses 161.1 5.6 166.7 317.4 6.7 324.1 Operating loss (80.7) (5.6) (86.3) (151.6) (6.7) (158.3) Loss before income tax expense (89.9) (5.6) (95.5) (166.3) (6.7) (173.0) Net loss (89.9) (5.6) (95.5) (166.3) (6.7) (173.0) Comprehensive loss $ (91.2) $ (5.6) $ (96.8) $ (171.3) $ (6.7) $ (178.0) Weighted-average common shares outstanding: basic and diluted (both Class A and B) 14.1 14.1 14.0 14.0 Loss per common share: basic and diluted (both Class A and B) $ (6.38) $ (6.77) $ (11.88) $ (12.36) As of June 30, 2022 (unaudited) As reported Adjustments As Corrected (in millions) Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity: Accumulated loss $ (1,436.4) $ (6.7) $ (1,443.1) Total stockholders’ equity $ 388.0 $ (6.7) $ 381.3 Six Months Ended June 30, 2022 (unaudited) As reported Adjustments As Corrected (in millions) Condensed consolidated statement of cash flows: Net loss $ (166.3) $ (6.7) $ (173.0) Other assets (10.5) 6.7 (3.8) Net cash used in operating activities $ (104.9) $ — $ (104.9)
Schedule of Cash and Cash Equivalents	The following table provides a reconciliation of cash, cash equivalents and restricted cash reported within the condensed consolidated balance sheets that sum to the total of the same such amount in the condensed consolidated statements of cash flows: As of June 30, December 31, 2023 2022 (dollars in millions) Cash and cash equivalents $ 628.0 $ 762.1 Restricted cash 1.0 1.0 Total cash, cash equivalents and restricted cash shown in the condensed consolidated statements of cash flows $ 629.0 $ 763.1

INVESTMENTS (Tables)

INVESTMENTS (Tables)	6 Months Ended
	Jun. 30, 2023
Investments, Debt and Equity Securities [Abstract]
Schedule of AFS Debt Securities	The amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities at June 30, 2023 and December 31, 2022 are as follows: June 30, 2023 Amortized Cost Allowance for Expected Credit Losses Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 15.2 $ — $ — $ (0.3) $ 14.9 Municipal securities 25.6 — — (1.2) 24.4 Corporate debt securities 70.0 — — (2.7) 67.3 Residential mortgage-backed securities 10.6 — — (0.4) 10.2 Commercial mortgage backed securities 29.2 — — (1.2) 28.0 Other debt obligations 15.3 — — (0.1) 15.2 Total fixed maturities 165.9 — — (5.9) 160.0 Short-term investments 2.7 — — — 2.7 Total $ 168.6 $ — $ — $ (5.9) $ 162.7 December 31, 2022 Amortized Cost Allowance for Expected Credit Losses Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 11.3 $ — $ — $ (0.3) $ 11.0 Municipal securities 21.4 — — (1.2) 20.2 Corporate debt securities 60.5 — — (2.7) 57.8 Residential mortgage-backed securities 5.5 — — (0.3) 5.2 Commercial mortgage backed securities 24.4 — — (1.2) 23.2 Other debt obligations 11.1 — 0.1 (0.2) 11.0 Total fixed maturities 134.2 — 0.1 (5.9) 128.4 Short-term investments 0.4 — — — 0.4 Total $ 134.6 $ — $ 0.1 $ (5.9) $ 128.8 The following table reflects the gross and net realized gains and losses on short-term investments, available-for-sale fixed maturities and other investments that have been included in the condensed consolidated statements of operations and comprehensive loss for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Realized gains on investments $ — $ — $ — $ 1.2 Realized losses on investments — (0.1) — (0.1) Net realized (losses) gains on investments $ — $ (0.1) $ — $ 1.1 The following table sets forth the amortized cost and fair value of short-term investments and available-for-sale fixed maturity securities by contractual maturity at June 30, 2023: June 30, 2023 Amortized Cost Fair Value (dollars in millions) Due in one year or less $ 34.1 $ 33.5 Due after one year through five years 100.0 96.2 Due five years through 10 years 19.1 18.4 Due after 10 years 15.4 14.6 Total $ 168.6 $ 162.7
Schedule of Unrealized Losses	The following tables reflect the gross unrealized losses and fair value of short-term investments and available-for-sale fixed maturity securities, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at June 30, 2023 and December 31, 2022: June 30, 2023 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 9.1 $ (0.1) $ 5.3 $ (0.2) $ 14.4 $ (0.3) Municipal securities 7.9 (0.1) 14.9 (1.1) 22.8 (1.2) Corporate debt securities 28.3 (0.6) 37.9 (2.1) 66.2 (2.7) Residential mortgage-backed securities 6.7 (0.1) 2.0 (0.3) 8.7 (0.4) Commercial mortgage-backed securities 13.4 (0.3) 14.5 (0.9) 27.9 (1.2) Other debt obligations 10.8 (0.1) 1.5 — 12.3 (0.1) Total fixed maturities 76.2 (1.3) 76.1 (4.6) 152.3 (5.9) Short-term investments 1.0 — — — 1.0 — Total $ 77.2 $ (1.3) $ 76.1 $ (4.6) $ 153.3 $ (5.9) December 31, 2022 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 6.9 $ (0.1) $ 4.1 $ (0.2) $ 11.0 $ (0.3) Municipal securities 11.5 (0.5) 8.2 (0.7) 19.7 (1.2) Corporate debt securities 45.3 (1.6) 11.5 (1.1) 56.8 (2.7) Residential mortgage-backed securities 2.2 — 1.9 (0.3) 4.1 (0.3) Commercial mortgage-backed securities 18.3 (0.8) 4.6 (0.4) 22.9 (1.2) Other debt obligations 6.8 (0.2) — — 6.8 (0.2) Total fixed maturities 91.0 (3.2) 30.3 (2.7) 121.3 (5.9) Short-term investments 0.1 — — — 0.1 — Total $ 91.1 $ (3.2) $ 30.3 $ (2.7) $ 121.4 $ (5.9)
Schedule of Net Investment Income	The following table sets forth the components of net investment income for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Interest on bonds $ 1.0 $ 0.5 $ 1.9 $ 1.1 Interest on deposits and cash equivalents 6.0 0.4 11.9 0.6 Total 7.0 0.9 13.8 1.7 Investment expense (0.2) (0.2) (0.3) (0.4) Net investment income $ 6.8 $ 0.7 $ 13.5 $ 1.3
Schedule of Credit Ratings	The following tables summarize the credit ratings of short-term investments and available-for-sale fixed maturity securities at June 30, 2023 and December 31, 2022: June 30, 2023 Amortized Cost Fair Value % of Total (dollars in millions) S&P Global rating or equivalent AAA $ 81.8 $ 79.1 48.6 % AA+, AA, AA-, A-1 26.7 25.8 15.9 A+, A, A- 45.0 43.0 26.4 BBB+, BBB, BBB- 15.1 14.8 9.1 Total $ 168.6 $ 162.7 100.0 % December 31, 2022 Amortized Cost Fair Value % of Total (dollars in millions) S&P Global rating or equivalent AAA $ 62.5 $ 59.9 46.5 % AA+, AA, AA-, A-1 19.9 19.1 14.8 A+, A, A- 38.4 36.5 28.3 BBB+, BBB, BBB- 13.8 13.3 10.4 Total $ 134.6 $ 128.8 100.0 %

FAIR VALUE OF FINANCIAL INSTR_2

FAIR VALUE OF FINANCIAL INSTRUMENTS (Tables)	6 Months Ended
	Jun. 30, 2023
Fair Value Disclosures [Abstract]
Schedule of Fair Value	The following tables provide information about our financial assets measured and reported at fair value as of June 30, 2023 and December 31, 2022: June 30, 2023 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 13.1 $ 1.8 $ — $ 14.9 Municipal securities — 24.4 — 24.4 Corporate debt securities — 67.3 — 67.3 Residential mortgage-backed securities — 10.2 — 10.2 Commercial mortgage-backed securities — 28.0 — 28.0 Other debt obligations — 15.2 — 15.2 Total fixed maturities 13.1 146.9 — 160.0 Short-term investments 2.4 0.3 — 2.7 Cash equivalents 404.3 — — 404.3 Total assets at fair value $ 419.8 $ 147.2 $ — $ 567.0 December 31, 2022 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 9.2 $ 1.8 $ — $ 11.0 Municipal securities — 20.2 — 20.2 Corporate debt securities — 57.8 — 57.8 Residential mortgage-backed securities — 5.2 — 5.2 Commercial mortgage-backed securities — 23.2 — 23.2 Other debt obligations — 11.0 — 11.0 Total fixed maturities 9.2 119.2 — 128.4 Short-term investments — 0.4 — 0.4 Cash equivalents 487.3 — — 487.3 Total assets at fair value $ 496.5 $ 119.6 $ — $ 616.1
Schedule of Carrying Amounts and Fair Values of Financial Instruments	As of June 30, 2023 and December 31, 2022, the carrying amounts and fair values of these financial instruments were as follows: Carrying Amount as of June 30, 2023 Estimated Fair Value as of June 30, 2023 Carrying Amount as of December 31, 2022 Estimated Fair Value as of December 31, 2022 (dollars in millions) Long-term debt $ 297.4 $ 310.2 $ 295.4 $ 309.7

LOSS AND LOSS ADJUSTMENT EXPE_2

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Tables)	6 Months Ended
	Jun. 30, 2023
Insurance [Abstract]
Schedule of Reconciliation of Reserve Balances for Loss and LAE, Net of Reinsurance	The following provides a reconciliation of the beginning and ending reserve balances for loss and LAE, net of reinsurance: Six Months Ended June 30, 2023 2022 (dollars in millions) Gross loss and LAE reserves, January 1 $ 287.4 $ 320.2 Reinsurance recoverable on unpaid losses (76.4) (79.5) Net loss and LAE reserves, January 1 211.0 240.7 Net incurred loss and LAE related to: Current year 123.6 191.9 Prior years (0.8) 0.5 Total incurred 122.8 192.4 Net paid loss and LAE related to: Current year 58.7 89.8 Prior years 99.0 96.0 Total paid 157.7 185.8 Net loss and LAE reserves, June 30 176.1 247.3 Plus reinsurance recoverable on unpaid losses 70.4 65.4 Gross loss and LAE reserves, June 30 $ 246.5 $ 312.7

REINSURANCE (Tables)

REINSURANCE (Tables)	6 Months Ended
	Jun. 30, 2023
Insurance [Abstract]
Schedule of Comprehensive Loss For Reinsurance	The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Premiums written: Direct $ 128.1 $ 130.8 $ 251.9 $ 304.3 Assumed 16.9 9.3 27.8 23.0 Ceded (67.2) (81.1) (137.1) (183.5) Net premiums written $ 77.8 $ 59.0 $ 142.6 $ 143.8 Premiums earned: Direct $ 120.2 $ 159.3 $ 240.3 $ 324.8 Assumed 11.3 11.5 21.3 20.7 Ceded (67.6) (96.1) (137.7) (192.5) Net premiums earned $ 63.9 $ 74.7 $ 123.9 $ 153.0 Losses and LAE incurred: Direct $ 90.5 $ 152.2 $ 190.3 $ 303.9 Assumed 8.7 13.2 16.4 24.4 Ceded (39.7) (69.7) (83.9) (135.9) Net losses and LAE incurred $ 59.5 $ 95.7 $ 122.8 $ 192.4 Gross premiums written by state is as follows for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 Amount % of Total Amount % of Total Amount % of Total Amount % of Total (dollars in millions) State: Texas $ 23.8 16.4 % $ 26.0 18.6 % $ 43.3 15.5 % $ 63.3 19.3 % Georgia 15.8 10.9 15.0 10.7 29.7 10.6 33.8 10.3 Colorado 11.9 8.2 9.8 7.0 22.5 8.0 20.5 6.3 Pennsylvania 7.6 5.2 7.7 5.5 16.9 6.0 17.7 5.4 South Carolina 10.6 7.3 4.8 3.4 16.8 6.0 11.9 3.6 Utah 7.4 5.1 7.1 5.1 14.6 5.2 16.1 4.9 Arizona 6.0 4.1 3.7 2.6 10.7 3.8 9.0 2.7 Louisiana 4.3 3.0 8.2 5.9 9.8 3.5 18.9 5.8 Oklahoma 4.8 3.3 4.6 3.3 9.5 3.4 10.9 3.3 Nevada 4.5 3.1 7.0 5.0 8.9 3.2 15.7 4.8 All others states 48.3 33.4 46.2 32.9 97.0 34.8 109.5 33.6 Total $ 145.0 100.0 % $ 140.1 100.0 % $ 279.7 100.0 % $ 327.3 100.0 %

LONG-TERM DEBT (Tables)

LONG-TERM DEBT (Tables)	6 Months Ended
	Jun. 30, 2023
Debt Disclosure [Abstract]
Schedule of Long Term Debt	The following summarizes the carrying value of long-term debt as of June 30, 2023 and December 31, 2022: June 30, 2023 December 31, 2022 (dollars in millions) Term Loan $ 300.0 $ 300.0 Accrued interest payable 7.8 7.3 Unamortized discount, debt issuance costs and warrants (10.4) (11.9) Total $ 297.4 $ 295.4

RESTRUCTURING COSTS (Tables)

RESTRUCTURING COSTS (Tables)	6 Months Ended
	Jun. 30, 2023
Restructuring and Related Activities [Abstract]
Restructuring Costs	The following table displays restructuring costs recorded in general and administrative expenses on the condensed consolidated statements of operations and comprehensive loss: Three Months Ended June 30, Six Months Ended June 30, Cumulative Incurred Through June 30, 2023 2023 2022 2023 2022 (dollars in millions) Restructuring costs: Employee costs $ 1.8 $ — $ 4.1 $ 5.6 $ 19.6 Real estate exit costs — 0.6 — 2.1 2.1 Other costs 0.1 — 3.4 0.7 4.4 Total restructuring costs $ 1.9 $ 0.6 $ 7.5 $ 8.4 $ 26.1 The following table displays a rollforward of the accrual for restructuring costs recorded in other liabilities on the condensed consolidated balance sheets: Employee costs Other costs Total liability (dollars in millions) Restructuring activity: Restructuring liability as of January 1, 2023 $ 3.1 $ 0.1 $ 3.2 Expense incurred 3.7 3.4 7.1 Payments (2.0) (3.5) (5.5) Restructuring liability as of June 30, 2023 $ 4.8 $ — $ 4.8

SHARE-BASED COMPENSATION (Table

SHARE-BASED COMPENSATION (Tables)	6 Months Ended
	Jun. 30, 2023
Share-Based Payment Arrangement [Abstract]
Schedule of Share-Based Compensation Expense	The following table displays warrant compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Warrant compensation expense: Sales and marketing $ — $ 3.5 $ — $ 8.8 Other insurance expense (benefit) 3.9 — 8.3 — Total warrant compensation expense $ 3.9 $ 3.5 $ 8.3 $ 8.8 The following table displays share-based compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Share-based compensation expense: Loss and loss adjustment expenses $ 0.2 $ 0.2 $ 0.3 $ 0.4 Sales and marketing 0.1 0.3 0.2 0.4 Other insurance expense (benefit) 0.2 0.3 0.3 0.5 Technology and development 0.8 1.3 1.5 2.0 General and administrative 3.9 5.3 5.4 10.7 Total share-based compensation expense $ 5.2 $ 7.4 $ 7.7 $ 14.0 The following table provides total share-based compensation expense by type of award: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Share-based compensation expense: Restricted stock unit expense $ 4.9 $ 7.0 $ 7.0 $ 13.1 Stock option expense 0.3 0.4 0.7 0.9 Total share-based compensation expense $ 5.2 $ 7.4 $ 7.7 $ 14.0
Summary of RSU Activity	A summary of RSU activity for the six months ended June 30, 2023 is as follows: Six Months Ended June 30, 2023 Restricted Stock Units Number of Shares Weighted-Average Aggregate Intrinsic Value (in millions, except per share amounts) Nonvested at January 1, 2023 1.1 $ 51.81 $ 5.0 Granted 0.8 5.56 Vested (0.4) 50.86 2.0 Forfeited, expired or canceled (0.2) 57.36 Nonvested at June 30, 2023 1.3 $ 23.16 $ 11.2
Summary of Option Activity	A summary of option activity for the six months ended June 30, 2023 is as follows: Six Months Ended June 30, 2023 Options Number of Shares Weighted-Average Exercise Price Weighted-Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in millions, except exercise price and term amounts) Outstanding and exercisable at January 1, 2023 0.2 $ 38.15 5.63 $ 0.2 Granted — 8.94 Exercised — — — Forfeited, expired or canceled (0.1) 44.87 Outstanding and exercisable at June 30, 2023 0.1 $ 33.75 4.80 $ 0.4

OTHER COMPREHENSIVE LOSS AND _2

OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME (Tables)	6 Months Ended
	Jun. 30, 2023
Equity [Abstract]
Schedule of AOCI	The following table presents the changes in our accumulated other comprehensive (loss) income, or AOCI, for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Beginning balance $ (4.7) $ (3.3) $ (5.8) $ 0.4 Other comprehensive loss before reclassifications (1.2) (1.4) (0.1) (5.1) Net realized gains on investments reclassified from AOCI to net loss — 0.1 — 0.1 Other comprehensive loss (1.2) (1.3) (0.1) (5.0) Ending balance $ (5.9) $ (4.6) $ (5.9) $ (4.6)

LOSS PER SHARE (Tables)

LOSS PER SHARE (Tables)	6 Months Ended
	Jun. 30, 2023
Earnings Per Share [Abstract]
Schedule of Earnings Per Share	The following table displays the computation of basic and diluted loss per share for both Class A and Class B common stock for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (in millions, except per share amounts) Net loss $ (36.7) $ (95.5) $ (77.6) $ (173.0) Weighted-average common shares outstanding: basic and diluted (both Class A and B) 14.4 14.1 14.3 14.0 Loss per common share: basic and diluted (both Class A and B) $ (2.55) $ (6.77) $ (5.43) $ (12.36)
Schedule of Anti-Dilutive Securities	We excluded the following potentially dilutive common stock equivalents, presented based on amounts outstanding at each period end, from the computation of diluted loss per share attributable to common shareholders for the periods indicated because including them would have had an anti-dilutive effect: As of June 30, 2023 2022 (in millions) Options to purchase common stock 0.1 0.2 Nonvested shares subject to repurchase 0.1 0.1 Restricted stock units 1.3 1.3 Redeemable convertible preferred stock (as converted to common stock) 0.8 0.8 Warrants to purchase common stock 7.6 7.7 Total 9.9 10.1

GEOGRAPHICAL BREAKDOWN OF GRO_2

GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN (Tables)	6 Months Ended
	Jun. 30, 2023
Insurance [Abstract]
Schedule of Direct and Assumed Premiums Written	The following table reflects amounts affecting the condensed consolidated statements of operations and comprehensive loss for reinsurance for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 (dollars in millions) Premiums written: Direct $ 128.1 $ 130.8 $ 251.9 $ 304.3 Assumed 16.9 9.3 27.8 23.0 Ceded (67.2) (81.1) (137.1) (183.5) Net premiums written $ 77.8 $ 59.0 $ 142.6 $ 143.8 Premiums earned: Direct $ 120.2 $ 159.3 $ 240.3 $ 324.8 Assumed 11.3 11.5 21.3 20.7 Ceded (67.6) (96.1) (137.7) (192.5) Net premiums earned $ 63.9 $ 74.7 $ 123.9 $ 153.0 Losses and LAE incurred: Direct $ 90.5 $ 152.2 $ 190.3 $ 303.9 Assumed 8.7 13.2 16.4 24.4 Ceded (39.7) (69.7) (83.9) (135.9) Net losses and LAE incurred $ 59.5 $ 95.7 $ 122.8 $ 192.4 Gross premiums written by state is as follows for the three and six months ended June 30, 2023 and 2022: Three Months Ended June 30, Six Months Ended June 30, 2023 2022 2023 2022 Amount % of Total Amount % of Total Amount % of Total Amount % of Total (dollars in millions) State: Texas $ 23.8 16.4 % $ 26.0 18.6 % $ 43.3 15.5 % $ 63.3 19.3 % Georgia 15.8 10.9 15.0 10.7 29.7 10.6 33.8 10.3 Colorado 11.9 8.2 9.8 7.0 22.5 8.0 20.5 6.3 Pennsylvania 7.6 5.2 7.7 5.5 16.9 6.0 17.7 5.4 South Carolina 10.6 7.3 4.8 3.4 16.8 6.0 11.9 3.6 Utah 7.4 5.1 7.1 5.1 14.6 5.2 16.1 4.9 Arizona 6.0 4.1 3.7 2.6 10.7 3.8 9.0 2.7 Louisiana 4.3 3.0 8.2 5.9 9.8 3.5 18.9 5.8 Oklahoma 4.8 3.3 4.6 3.3 9.5 3.4 10.9 3.3 Nevada 4.5 3.1 7.0 5.0 8.9 3.2 15.7 4.8 All others states 48.3 33.4 46.2 32.9 97.0 34.8 109.5 33.6 Total $ 145.0 100.0 % $ 140.1 100.0 % $ 279.7 100.0 % $ 327.3 100.0 %

NATURE OF BUSINESS (Details)

NATURE OF BUSINESS (Details)	Jun. 30, 2023
Root Insurance Company
Schedule of Equity Method Investments [Line Items]
Ownership percentage (as percent)	100%
Root Property & Casualty Insurance Company
Schedule of Equity Method Investments [Line Items]
Ownership percentage (as percent)	100%
Root Reinsurance Company, Ltd.
Schedule of Equity Method Investments [Line Items]
Ownership percentage (as percent)	100%

BASIS OF PRESENTATION AND SUM_4

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Error Correction (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022	Mar. 31, 2023	Dec. 31, 2022	Mar. 31, 2022	Dec. 31, 2021
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing	$ 6.1	$ 21.4	$ 9.7	$ 36.7
General and administrative	20.7	39.5	42.2	70
Total operating expenses	100	166.7	199.9	324.1
Operating loss	(25.2)	(86.3)	(55)	(158.3)
Loss before income tax expense	(36.7)	(95.5)	(77.6)	(173)
Net loss	(36.7)	(95.5)	(77.6)	(173)
Comprehensive loss	$ (37.9)	$ (96.8)	$ (77.7)	$ (178)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)	14.4	14.1	14.3	14
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)	14.4	14.1	14.3	14
Loss per common share: basic (both Class A and B) (in dollars per share)	$ (2.55)	$ (6.77)	$ (5.43)	$ (12.36)
Loss per common share: diluted (both Class A and B) (in dollars per share)	$ (2.55)	$ (6.77)	$ (5.43)	$ (12.36)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity:
Total stockholders’ equity	$ 214.4	$ 381.3	$ 214.4	$ 381.3	$ 243.7	$ 277.1	$ 467.6	$ 536.4
Condensed consolidated statement of cash flows:
Net loss	(36.7)	(95.5)	(77.6)	(173)
Other assets			14.6	(3.8)
Net cash used in operating activities			(94.3)	(104.9)
Accumulated Loss
Condensed consolidated statements of operations and comprehensive loss:
Net loss	(36.7)	(95.5)	(77.6)	(173)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity:
Total stockholders’ equity	(1,645.4)	(1,443.1)	(1,645.4)	(1,443.1)	$ (1,608.7)	$ (1,567.8)	$ (1,347.6)	$ (1,270.1)
Condensed consolidated statement of cash flows:
Net loss	$ (36.7)	(95.5)	$ (77.6)	(173)
As reported
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing		25.4		40.1
General and administrative		29.9		59.9
Total operating expenses		161.1		317.4
Operating loss		(80.7)		(151.6)
Loss before income tax expense		(89.9)		(166.3)
Net loss		(89.9)		(166.3)
Comprehensive loss		$ (91.2)		$ (171.3)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)		14.1		14
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)		14.1		14
Loss per common share: basic (both Class A and B) (in dollars per share)		$ (6.38)		$ (11.88)
Loss per common share: diluted (both Class A and B) (in dollars per share)		$ (6.38)		$ (11.88)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity:
Total stockholders’ equity		$ 388		$ 388
Condensed consolidated statement of cash flows:
Net loss		(89.9)		(166.3)
Other assets				(10.5)
Net cash used in operating activities				(104.9)
As reported | Accumulated Loss
Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity:
Total stockholders’ equity		(1,436.4)		(1,436.4)
Adjustments
Condensed consolidated statements of operations and comprehensive loss:
Sales and marketing		(4)		(3.4)
General and administrative		9.6		10.1
Total operating expenses		5.6		6.7
Operating loss		(5.6)		(6.7)
Loss before income tax expense		(5.6)		(6.7)
Net loss		(5.6)		(6.7)
Comprehensive loss		(5.6)		(6.7)
Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity:
Total stockholders’ equity		(6.7)		(6.7)
Condensed consolidated statement of cash flows:
Net loss		(5.6)		(6.7)
Other assets				6.7
Adjustments | Accumulated Loss
Condensed consolidated statement of redeemable convertible preferred stock and stockholders equity:
Total stockholders’ equity		$ (6.7)		$ (6.7)

BASIS OF PRESENTATION AND SUM_5

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Additional Information (Details)	Aug. 12, 2022 shares
Accounting Policies [Abstract]
Conversion ratio	0.0556
Shares converted (in shares)	18
Conversion of stock, shares issued (in shares)	1

BASIS OF PRESENTATION AND SUM_6

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Cash, Cash Equivalents and Restricted Cash (Details) - USD ($) $ in Millions	Jun. 30, 2023	Dec. 31, 2022	Jun. 30, 2022	Dec. 31, 2021
Accounting Policies [Abstract]
Cash and cash equivalents	$ 628	$ 762.1
Restricted cash	1	1
Total cash, cash equivalents and restricted cash shown in the condensed consolidated statements of cash flows	$ 629	$ 763.1	$ 886.6	$ 707

INVESTMENTS - Amortized Cost an

INVESTMENTS - Amortized Cost and Fair Value (Details) - USD ($) $ in Millions	Jun. 30, 2023	Dec. 31, 2022
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 168.6	$ 134.6
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0.1
Gross Unrealized Losses	(5.9)	(5.9)
Fair Value	162.7	128.8
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	15.2	11.3
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0
Gross Unrealized Losses	(0.3)	(0.3)
Fair Value	14.9	11
Municipal securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	25.6	21.4
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0
Gross Unrealized Losses	(1.2)	(1.2)
Fair Value	24.4	20.2
Corporate debt securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	70	60.5
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0
Gross Unrealized Losses	(2.7)	(2.7)
Fair Value	67.3	57.8
Residential mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	10.6	5.5
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0
Gross Unrealized Losses	(0.4)	(0.3)
Fair Value	10.2	5.2
Commercial mortgage backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	29.2	24.4
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0
Gross Unrealized Losses	(1.2)	(1.2)
Fair Value	28	23.2
Other debt obligations
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	15.3	11.1
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0.1
Gross Unrealized Losses	(0.1)	(0.2)
Fair Value	15.2	11
Total fixed maturities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	165.9	134.2
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0.1
Gross Unrealized Losses	(5.9)	(5.9)
Fair Value	160	128.4
Short-term investments
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	2.7	0.4
Allowance for Expected Credit Losses	0	0
Gross Unrealized Gains	0	0
Gross Unrealized Losses	0	0
Fair Value	$ 2.7	$ 0.4

INVESTMENTS - Unrealized Losses

INVESTMENTS - Unrealized Losses (Details) - USD ($) $ in Millions	Jun. 30, 2023	Dec. 31, 2022
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	$ 77.2	$ 91.1
Less than 12 months, unrealized loss	(1.3)	(3.2)
12 months or more, fair value	76.1	30.3
12 months or more, unrealized loss	(4.6)	(2.7)
Total, fair value	153.3	121.4
Total, unrealized loss	(5.9)	(5.9)
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	9.1	6.9
Less than 12 months, unrealized loss	(0.1)	(0.1)
12 months or more, fair value	5.3	4.1
12 months or more, unrealized loss	(0.2)	(0.2)
Total, fair value	14.4	11
Total, unrealized loss	(0.3)	(0.3)
Municipal securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	7.9	11.5
Less than 12 months, unrealized loss	(0.1)	(0.5)
12 months or more, fair value	14.9	8.2
12 months or more, unrealized loss	(1.1)	(0.7)
Total, fair value	22.8	19.7
Total, unrealized loss	(1.2)	(1.2)
Corporate debt securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	28.3	45.3
Less than 12 months, unrealized loss	(0.6)	(1.6)
12 months or more, fair value	37.9	11.5
12 months or more, unrealized loss	(2.1)	(1.1)
Total, fair value	66.2	56.8
Total, unrealized loss	(2.7)	(2.7)
Residential mortgage-backed securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	6.7	2.2
Less than 12 months, unrealized loss	(0.1)	0
12 months or more, fair value	2	1.9
12 months or more, unrealized loss	(0.3)	(0.3)
Total, fair value	8.7	4.1
Total, unrealized loss	(0.4)	(0.3)
Commercial mortgage backed securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	13.4	18.3
Less than 12 months, unrealized loss	(0.3)	(0.8)
12 months or more, fair value	14.5	4.6
12 months or more, unrealized loss	(0.9)	(0.4)
Total, fair value	27.9	22.9
Total, unrealized loss	(1.2)	(1.2)
Other debt obligations
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	10.8	6.8
Less than 12 months, unrealized loss	(0.1)	(0.2)
12 months or more, fair value	1.5	0
12 months or more, unrealized loss	0	0
Total, fair value	12.3	6.8
Total, unrealized loss	(0.1)	(0.2)
Total fixed maturities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	76.2	91
Less than 12 months, unrealized loss	(1.3)	(3.2)
12 months or more, fair value	76.1	30.3
12 months or more, unrealized loss	(4.6)	(2.7)
Total, fair value	152.3	121.3
Total, unrealized loss	(5.9)	(5.9)
Short-term investments
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 months, fair value	1	0.1
Less than 12 months, unrealized loss	0	0
12 months or more, fair value	0	0
12 months or more, unrealized loss	0	0
Total, fair value	1	0.1
Total, unrealized loss	$ 0	$ 0

INVESTMENTS - Other Investments

INVESTMENTS - Other Investments (Details) - USD ($)	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022	Dec. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Other investments	$ 4,400,000		$ 4,400,000		$ 4,400,000
Realized gains on investments	$ 0	$ 0	$ 0	$ 1,200,000

INVESTMENTS - Gross and Net Rea

INVESTMENTS - Gross and Net Realized Gains and Losses (Details) - USD ($)	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Investments, Debt and Equity Securities [Abstract]
Realized gains on investments	$ 0	$ 0	$ 0	$ 1,200,000
Realized losses on investments	0	(100,000)	0	(100,000)
Net realized (losses) gains on investments	$ 0	$ (100,000)	$ 0	$ 1,100,000

INVESTMENTS - Contractual Matur

INVESTMENTS - Contractual Maturity (Details) - USD ($) $ in Millions	Jun. 30, 2023	Dec. 31, 2022
Amortized Cost
Due in one year or less	$ 34.1
Due after one year through five years	100
Due five years through 10 years	19.1
Due after 10 years	15.4
Amortized Cost	168.6	$ 134.6
Fair Value
Due in one year or less	33.5
Due after one year through five years	96.2
Due five years through 10 years	18.4
Due after 10 years	14.6
Total	$ 162.7	$ 128.8

INVESTMENTS - Net Investment In

INVESTMENTS - Net Investment Income (Details) - USD ($) $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Net Investment Income [Line Items]
Realized gain value	$ 7	$ 0.9	$ 13.8	$ 1.7
Investment expense	(0.2)	(0.2)	(0.3)	(0.4)
Net investment income	6.8	0.7	13.5	1.3
Interest on bonds
Net Investment Income [Line Items]
Realized gain value	1	0.5	1.9	1.1
Interest on deposits and cash equivalents
Net Investment Income [Line Items]
Realized gain value	$ 6	$ 0.4	$ 11.9	$ 0.6

INVESTMENTS - Credit Ratings (D

INVESTMENTS - Credit Ratings (Details) - USD ($) $ in Millions	6 Months Ended	12 Months Ended
	Jun. 30, 2023	Dec. 31, 2022
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 168.6	$ 134.6
Fair Value	$ 162.7	$ 128.8
AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	100%	100%
AAA
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 81.8	$ 62.5
Fair Value	$ 79.1	$ 59.9
AAA | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	48.60%	46.50%
AA+, AA, AA-, A-1
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 26.7	$ 19.9
Fair Value	$ 25.8	$ 19.1
AA+, AA, AA-, A-1 | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	15.90%	14.80%
A+, A, A-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 45	$ 38.4
Fair Value	$ 43	$ 36.5
A+, A, A- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	26.40%	28.30%
BBB+, BBB, BBB-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 15.1	$ 13.8
Fair Value	$ 14.8	$ 13.3
BBB+, BBB, BBB- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage (in percent)	9.10%	10.40%

FAIR VALUE OF FINANCIAL INSTR_3

FAIR VALUE OF FINANCIAL INSTRUMENTS - Balance Sheet Grouping (Details) - USD ($) $ in Millions	Jun. 30, 2023	Dec. 31, 2022
Assets
AFS securities	$ 162.7	$ 128.8
Cash equivalents	404.3	487.3
Total assets at fair value	567	616.1
U.S. Treasury securities and agencies
Assets
AFS securities	14.9	11
Municipal securities
Assets
AFS securities	24.4	20.2
Corporate debt securities
Assets
AFS securities	67.3	57.8
Residential mortgage-backed securities
Assets
AFS securities	10.2	5.2
Commercial mortgage backed securities
Assets
AFS securities	28	23.2
Other debt obligations
Assets
AFS securities	15.2	11
Total fixed maturities
Assets
AFS securities	160	128.4
Short-term investments
Assets
AFS securities	2.7	0.4
Level 1
Assets
Cash equivalents	404.3	487.3
Total assets at fair value	419.8	496.5
Level 1 | U.S. Treasury securities and agencies
Assets
AFS securities	13.1	9.2
Level 1 | Municipal securities
Assets
AFS securities	0	0
Level 1 | Corporate debt securities
Assets
AFS securities	0	0
Level 1 | Residential mortgage-backed securities
Assets
AFS securities	0	0
Level 1 | Commercial mortgage backed securities
Assets
AFS securities	0	0
Level 1 | Other debt obligations
Assets
AFS securities	0	0
Level 1 | Total fixed maturities
Assets
AFS securities	13.1	9.2
Level 1 | Short-term investments
Assets
AFS securities	2.4	0
Level 2
Assets
Cash equivalents	0	0
Total assets at fair value	147.2	119.6
Level 2 | U.S. Treasury securities and agencies
Assets
AFS securities	1.8	1.8
Level 2 | Municipal securities
Assets
AFS securities	24.4	20.2
Level 2 | Corporate debt securities
Assets
AFS securities	67.3	57.8
Level 2 | Residential mortgage-backed securities
Assets
AFS securities	10.2	5.2
Level 2 | Commercial mortgage backed securities
Assets
AFS securities	28	23.2
Level 2 | Other debt obligations
Assets
AFS securities	15.2	11
Level 2 | Total fixed maturities
Assets
AFS securities	146.9	119.2
Level 2 | Short-term investments
Assets
AFS securities	0.3	0.4
Level 3
Assets
Cash equivalents	0	0
Total assets at fair value	0	0
Level 3 | U.S. Treasury securities and agencies
Assets
AFS securities	0	0
Level 3 | Municipal securities
Assets
AFS securities	0	0
Level 3 | Corporate debt securities
Assets
AFS securities	0	0
Level 3 | Residential mortgage-backed securities
Assets
AFS securities	0	0
Level 3 | Commercial mortgage backed securities
Assets
AFS securities	0	0
Level 3 | Other debt obligations
Assets
AFS securities	0	0
Level 3 | Total fixed maturities
Assets
AFS securities	0	0
Level 3 | Short-term investments
Assets
AFS securities	$ 0	$ 0

FAIR VALUE OF FINANCIAL INSTR_4

FAIR VALUE OF FINANCIAL INSTRUMENTS - Long Term Debt (Details) - Level 2 - USD ($) $ in Millions	Jun. 30, 2023	Dec. 31, 2022
Carrying amount
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 297.4	$ 295.4
Estimated Fair Value
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 310.2	$ 309.7

LOSS AND LOSS ADJUSTMENT EXPE_3

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES - Schedule of Reserve Balance (Details) - USD ($) $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022	Dec. 31, 2022	Dec. 31, 2021
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Gross loss and LAE reserves, January 1			$ 287.4	$ 320.2
Reinsurance recoverable on unpaid losses			(76.4)	(79.5)
Net loss and LAE reserves, January 1	$ 176.1	$ 247.3	176.1	247.3	$ 211	$ 240.7
Net incurred loss and LAE related to:
Current year			123.6	191.9
Prior years			(0.8)	0.5
Total incurred	59.5	95.7	122.8	192.4
Net paid loss and LAE related to:
Current year			58.7	89.8
Prior years			99	96
Total paid			157.7	185.8
Net loss and LAE reserves, June 30	176.1	247.3	176.1	247.3
Plus reinsurance recoverable on unpaid losses	70.4	65.4	70.4	65.4
Gross loss and LAE reserves, June 30	$ 246.5	$ 312.7	$ 246.5	$ 312.7

LOSS AND LOSS ADJUSTMENT EXPE_4

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES - Narrative (Details) - USD ($) $ in Millions	6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022
Insurance [Abstract]
Incurred losses and LAE attributable to prior accident years	$ 0.8	$ (0.5)

REINSURANCE (Details)

REINSURANCE (Details) - USD ($) $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Premiums written:
Direct	$ 128.1	$ 130.8	$ 251.9	$ 304.3
Assumed	16.9	9.3	27.8	23
Ceded	(67.2)	(81.1)	(137.1)	(183.5)
Net premiums written	77.8	59	142.6	143.8
Premiums earned:
Direct	120.2	159.3	240.3	324.8
Assumed	11.3	11.5	21.3	20.7
Ceded	(67.6)	(96.1)	(137.7)	(192.5)
Net premiums earned	63.9	74.7	123.9	153
Losses and LAE incurred:
Direct	90.5	152.2	190.3	303.9
Assumed	8.7	13.2	16.4	24.4
Ceded	(39.7)	(69.7)	(83.9)	(135.9)
Net losses and LAE incurred	$ 59.5	$ 95.7	$ 122.8	$ 192.4

LONG-TERM DEBT - Narrative (Det

LONG-TERM DEBT - Narrative (Details) - Term Loan - USD ($)		1 Months Ended	6 Months Ended
	Jan. 27, 2022	Jan. 31, 2022	Jun. 30, 2023
Debt Instrument [Line Items]
Stated percentage (in percent)	0.26161%
SOFR
Debt Instrument [Line Items]
Debt instrument, floor interest rate (in percent)	1%		1%
Variable rate percentage (in percent)	9%		9%
Secured debt
Debt Instrument [Line Items]
Debt amount		$ 300,000,000
Debt instrument, term		5 years

LONG-TERM DEBT - Schedule Of De

LONG-TERM DEBT - Schedule Of Debt (Details) - USD ($) $ in Millions	Jun. 30, 2023	Dec. 31, 2022
Debt Instrument [Line Items]
Accrued interest payable	$ 7.8	$ 7.3
Unamortized discount, debt issuance costs and warrants	(10.4)	(11.9)
Total	297.4	295.4
Secured debt | Term Loan
Debt Instrument [Line Items]
Term Loan	$ 300	$ 300

INCOME TAXES (Details)

INCOME TAXES (Details)	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Income Tax Disclosure [Abstract]
Effective income tax rate	0%	0%	0%	0%
Federal income tax rate (in percent)			21%

RESTRUCTURING COSTS - Narrative

RESTRUCTURING COSTS - Narrative (Details) $ in Millions	Jun. 30, 2023 USD ($)
Restructuring and Related Activities [Abstract]
Restructuring and related cost, expected cost	$ 3.6

RESTRUCTURING COSTS - Restructu

RESTRUCTURING COSTS - Restructuring Costs Recorded In Consolidated Statements Of Operations And Comprehensive Loss (Details) - General and administrative - USD ($) $ in Millions	3 Months Ended		6 Months Ended		18 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023
Restructuring Cost and Reserve [Line Items]
Total restructuring costs	$ 1.9	$ 0.6	$ 7.5	$ 8.4	$ 26.1
Employee costs
Restructuring Cost and Reserve [Line Items]
Total restructuring costs	1.8	0	4.1	5.6	19.6
Real estate exit costs
Restructuring Cost and Reserve [Line Items]
Total restructuring costs	0	0.6	0	2.1	2.1
Other costs
Restructuring Cost and Reserve [Line Items]
Total restructuring costs	$ 0.1	$ 0	$ 3.4	$ 0.7	$ 4.4

RESTRUCTURING COSTS - Restruc_2

RESTRUCTURING COSTS - Restructuring Costs Recorded In Consolidated Balance Sheets (Details) $ in Millions	6 Months Ended
	Jun. 30, 2023 USD ($)
Restructuring activity:
Restructuring liability, beginning balance	$ 3.2
Expense incurred	7.1
Payments	(5.5)
Restructuring liability, ending balance	4.8
Employee costs
Restructuring activity:
Restructuring liability, beginning balance	3.1
Expense incurred	3.7
Payments	(2)
Restructuring liability, ending balance	4.8
Other costs
Restructuring activity:
Restructuring liability, beginning balance	0.1
Expense incurred	3.4
Payments	(3.5)
Restructuring liability, ending balance	$ 0

SHARE-BASED COMPENSATION - Narr

SHARE-BASED COMPENSATION - Narrative (Details) shares in Millions, $ in Millions	6 Months Ended
	Jun. 30, 2023 USD ($) shares	Oct. 31, 2021 tranche shares
2020 Equity Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares available for issuance (in shares) | shares	2
Warrant
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost | $	$ 12.8
Unrecognized compensation cost, period of recognition	2 years
Stock option expense
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, period of recognition	3 years
Unrecognized compensation cost, options | $	$ 1.5
Restricted stock unit expense
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost | $	$ 26
Unrecognized compensation cost, period of recognition	4 years
Class A Shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares issued (in shares) | shares		7.2
Short Term Warrant
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of tranches | tranche		3
Long Term Warrant
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of tranches | tranche		5
Carvana
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Number of tranches | tranche		8

SHARE-BASED COMPENSATION - Warr

SHARE-BASED COMPENSATION - Warrant Compensation Expense (Details) - USD ($) $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 5.2	$ 7.4	$ 7.7	$ 14
Sales and marketing
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	0.1	0.3	0.2	0.4
Other insurance expense (benefit)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	0.2	0.3	0.3	0.5
Warrant
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	3.9	3.5	8.3	8.8
Warrant | Sales and marketing
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	0	3.5	0	8.8
Warrant | Other insurance expense (benefit)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 3.9	$ 0	$ 8.3	$ 0

SHARE-BASED COMPENSATION - Shar

SHARE-BASED COMPENSATION - Share-based Compensation Expense (Details) - USD ($) $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 5.2	$ 7.4	$ 7.7	$ 14
Restricted stock unit expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	4.9	7	7	13.1
Stock option expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.3	0.4	0.7	0.9
Loss and loss adjustment expenses
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.2	0.2	0.3	0.4
Sales and marketing
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.1	0.3	0.2	0.4
Other insurance expense (benefit)
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.2	0.3	0.3	0.5
Technology and development
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.8	1.3	1.5	2
General and administrative
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 3.9	$ 5.3	$ 5.4	$ 10.7

SHARE-BASED COMPENSATION - RSU

SHARE-BASED COMPENSATION - RSU Activity (Details) - Restricted stock unit expense $ / shares in Units, shares in Millions, $ in Millions	6 Months Ended
	Jun. 30, 2023 USD ($) $ / shares shares
Number of Shares
Beginning balance (in shares) | shares	1.1
Granted (in shares) | shares	0.8
Vested (in shares) | shares	(0.4)
Forfeited, expired or canceled (in shares) | shares	(0.2)
Ending balance (in shares) | shares	1.3
Weighted-Average Grant Date Fair Value per Share
Beginning balance (in dollars per share) | $ / shares	$ 51.81
Granted (in dollars per share) | $ / shares	5.56
Vested (in dollars per share) | $ / shares	50.86
Forfeited, expired or canceled (in dollars per share) | $ / shares	57.36
Ending balance (in dollars per share) | $ / shares	$ 23.16
Aggregate Intrinsic Value
Beginning balance | $	$ 5
Vested | $	2
Ending balance | $	$ 11.2

SHARE-BASED COMPENSATION - Opti

SHARE-BASED COMPENSATION - Option Activity (Details) $ / shares in Units, shares in Millions, $ in Millions	6 Months Ended	12 Months Ended
	Jun. 30, 2023 USD ($) $ / shares shares	Dec. 31, 2022 USD ($) $ / shares shares
Number of Shares
Outstanding, beginning balance (in shares) | shares	0.2
Granted (in shares) | shares	0
Exercised (in shares) | shares	0
Forfeited, expired or canceled (in shares) | shares	(0.1)
Outstanding, ending balance (in shares) | shares	0.1	0.2
Weighted-Average Exercise Price
Outstanding, beginning balance (in dollars per share) | $ / shares	$ 38.15
Granted (in dollars per share) | $ / shares	8.94
Exercised (in dollars per share) | $ / shares	0
Forfeited, expired and canceled (in dollars per share) | $ / shares	44.87
Outstanding, ending balance (in dollars per share) | $ / shares	$ 33.75	$ 38.15
Outstanding, weighted-average remaining contractual term (in years)	4 years 9 months 18 days	5 years 7 months 17 days
Outstanding, aggregate intrinsic value | $	$ 0.4	$ 0.2
Exercised, aggregate intrinsic value | $	$ 0

OTHER COMPREHENSIVE LOSS AND _3

OTHER COMPREHENSIVE LOSS AND ACCUMULATED OTHER COMPREHENSIVE (LOSS) INCOME (Details) - USD ($) $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	$ 243.7	$ 467.6	$ 277.1	$ 536.4
Other comprehensive loss	(1.2)	(1.3)	(0.1)	(5)
Ending balance	214.4	381.3	214.4	381.3
Change in net unrealized gains (losses) on investments:
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	(4.7)	(3.3)	(5.8)	0.4
Other comprehensive loss before reclassifications	(1.2)	(1.4)	(0.1)	(5.1)
Net realized gains on investments reclassified from AOCI to net loss	0	0.1	0	0.1
Other comprehensive loss	(1.2)	(1.3)	(0.1)	(5)
Ending balance	$ (5.9)	$ (4.6)	$ (5.9)	$ (4.6)

LOSS PER SHARE - Schedule of Ba

LOSS PER SHARE - Schedule of Basic and Diluted Loss per Share (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Earnings Per Share [Abstract]
Net loss	$ (36.7)	$ (95.5)	$ (77.6)	$ (173)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)	14.4	14.1	14.3	14
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)	14.4	14.1	14.3	14
Loss per common share: basic (both Class A and B) (in dollars per share)	$ (2.55)	$ (6.77)	$ (5.43)	$ (12.36)
Loss per common share: diluted (both Class A and B) (in dollars per share)	$ (2.55)	$ (6.77)	$ (5.43)	$ (12.36)

LOSS PER SHARE - Schedule of An

LOSS PER SHARE - Schedule of Anti-Dilutive Securities (Details) - shares shares in Millions	6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	9.9	10.1
Options to purchase common stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	0.1	0.2
Nonvested shares subject to repurchase
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	0.1	0.1
Restricted stock units
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	1.3	1.3
Redeemable convertible preferred stock (as converted to common stock)
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	0.8	0.8
Warrants to purchase common stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	7.6	7.7

GEOGRAPHICAL BREAKDOWN OF GRO_3

GEOGRAPHICAL BREAKDOWN OF GROSS PREMIUMS WRITTEN (Details) - USD ($) $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Effects of Reinsurance [Line Items]
Total	$ 145	$ 140.1	$ 279.7	$ 327.3
Texas
Effects of Reinsurance [Line Items]
Total	23.8	26	43.3	63.3
Georgia
Effects of Reinsurance [Line Items]
Total	15.8	15	29.7	33.8
Colorado
Effects of Reinsurance [Line Items]
Total	11.9	9.8	22.5	20.5
Pennsylvania
Effects of Reinsurance [Line Items]
Total	7.6	7.7	16.9	17.7
South Carolina
Effects of Reinsurance [Line Items]
Total	10.6	4.8	16.8	11.9
Utah
Effects of Reinsurance [Line Items]
Total	7.4	7.1	14.6	16.1
Arizona
Effects of Reinsurance [Line Items]
Total	6	3.7	10.7	9
Louisiana
Effects of Reinsurance [Line Items]
Total	4.3	8.2	9.8	18.9
Oklahoma
Effects of Reinsurance [Line Items]
Total	4.8	4.6	9.5	10.9
Nevada
Effects of Reinsurance [Line Items]
Total	4.5	7	8.9	15.7
All others states
Effects of Reinsurance [Line Items]
Total	$ 48.3	$ 46.2	$ 97	$ 109.5
Geographic Concentration Risk | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	100%	100%	100%	100%
Geographic Concentration Risk | Gross Written Premiums | Texas
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	16.40%	18.60%	15.50%	19.30%
Geographic Concentration Risk | Gross Written Premiums | Georgia
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	10.90%	10.70%	10.60%	10.30%
Geographic Concentration Risk | Gross Written Premiums | Colorado
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	8.20%	7%	8%	6.30%
Geographic Concentration Risk | Gross Written Premiums | Pennsylvania
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	5.20%	5.50%	6%	5.40%
Geographic Concentration Risk | Gross Written Premiums | South Carolina
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	7.30%	3.40%	6%	3.60%
Geographic Concentration Risk | Gross Written Premiums | Utah
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	5.10%	5.10%	5.20%	4.90%
Geographic Concentration Risk | Gross Written Premiums | Arizona
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	4.10%	2.60%	3.80%	2.70%
Geographic Concentration Risk | Gross Written Premiums | Louisiana
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	3%	5.90%	3.50%	5.80%
Geographic Concentration Risk | Gross Written Premiums | Oklahoma
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	3.30%	3.30%	3.40%	3.30%
Geographic Concentration Risk | Gross Written Premiums | Nevada
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	3.10%	5%	3.20%	4.80%
Geographic Concentration Risk | Gross Written Premiums | All others states
Effects of Reinsurance [Line Items]
Concentration percentage (in percent)	33.40%	32.90%	34.80%	33.60%