Root (ROOT) 10-Q 10 Nov 21 2021 Q3 Quarterly report Financial data

COVER PAGE

COVER PAGE - shares shares in Millions	9 Months Ended
	Sep. 30, 2021	Nov. 04, 2021
Entity Listings [Line Items]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Sep. 30, 2021
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	Non-accelerated Filer
Entity Small Business	false
Entity Emerging Growth Company	true
Entity Ex Transition Period	false
Entity Shell Company	false
Amendment Flag	false
Document Fiscal Year Focus	2021
Document Fiscal Period Focus	Q3
Entity Central Index Key	0001788882
Current Fiscal Year End Date	--12-31
Class A Shares
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		132.5
Class B Shares
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		120

CONDENSED CONSOLIDATED BALANCE

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED - USD ($) shares in Millions, $ in Millions	Sep. 30, 2021	Dec. 31, 2020
Investments:
Fixed maturities available-for sale, at fair value (amortized cost: $129.2 and $215.4 at September 30, 2021 and December 31, 2020, respectively)	$ 130.8	$ 221
Short-term investments (amortized cost: zero and $3.0 at September 30, 2021 and December 31, 2020, respectively)	0	3
Other investments	1.3	0.5
Total investments	132.1	224.5
Cash and cash equivalents	834.1	1,112.8
Restricted cash	1	1
Premiums receivable, net of allowance of $3.3 and $3.5 at September 30, 2021 and December 31, 2020, respectively	175.8	130.1
Reinsurance recoverable	176.4	124.8
Prepaid reinsurance premiums	114.7	112.8
Other assets	90.4	56.3
Total assets	1,524.5	1,762.3
Liabilities:
Loss and loss adjustment expense reserves	300.7	237.2
Unearned premiums	210.9	157.1
Long-term debt	201.7	188.2
Reinsurance premiums payable	89	89.1
Accounts payable and accrued expenses	41.5	48
Other liabilities	44.7	10.3
Total liabilities	888.5	729.9
Commitments and Contingencies (Note 11)
Stockholders’ equity:
Preferred stock, $0.0001 par value, 100.0 shares authorized, zero shares issued and outstanding at September 30, 2021 and December 31, 2020, respectively	0	0
Treasury stock, at cost	(0.8)	(0.8)
Additional paid-in capital	1,794.4	1,775.6
Accumulated other comprehensive income	1.6	5.6
Accumulated loss	(1,159.2)	(748)
Total stockholders’ equity	636	1,032.4
Total liabilities and stockholders’ equity	$ 1,524.5	$ 1,762.3
Class A Shares
Stockholders’ equity:
Common stock, shares issued (in shares)	127	59.4
Common stock, shares outstanding (in shares)	127	59.4
Common stock	$ 0	$ 0
Class B Shares
Stockholders’ equity:
Common stock, shares issued (in shares)	125.5	192.2
Common stock, shares outstanding (in shares)	125.5	192.2
Common stock	$ 0	$ 0

CONDENSED CONSOLIDATED BALANC_2

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED (Parenthetical) - USD ($)	Sep. 30, 2021	Dec. 31, 2020
Amortized cost, fixed maturities	$ 129,200,000	$ 215,400,000
Amortized cost, short term investments	0	3,000,000
Allowance for premiums receivable	$ 3,300,000	$ 3,500,000
Preferred stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Preferred stock, shares authorized (in shares)	100,000,000	100,000,000
Preferred stock, shares issued (in shares)	0	0
Preferred stock, shares outstanding (in shares)	0	0
Class A Shares
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	1,000,000,000	1,000,000,000
Common stock, shares issued (in shares)	127,000,000	59,400,000
Common stock, shares outstanding (in shares)	127,000,000	59,400,000
Class B Shares
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	269,000,000	269,000,000
Common stock, shares issued (in shares)	125,500,000	192,200,000
Common stock, shares outstanding (in shares)	125,500,000	192,200,000

CONDENSED CONSOLIDATED STATEMEN

CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS - UNAUDITED - USD ($) shares in Millions, $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Revenues:
Net premiums earned	$ 85.1	$ 44.9	$ 225.4	$ 278.4
Net investment income	1	1.1	2.6	4.3
Net realized gains on investments	0	0.1	2.4	0.2
Fee and other income	7.7	4.4	21.8	13
Total revenues	93.8	50.5	252.2	295.9
Operating expenses:
Loss and loss adjustment expenses	114.4	76.1	284.5	303.3
Sales and marketing	65.4	36.9	245.5	90.1
Other insurance (benefit) expense	(4.5)	(26.3)	(3.6)	0.3
Technology and development	18	12.9	49.3	40.2
General and administrative	27.4	16.6	69.8	58.8
Total operating expenses	220.7	116.2	645.5	492.7
Operating loss	(126.9)	(65.7)	(393.3)	(196.8)
Interest expense	(6.1)	(19.5)	(17.9)	(32.9)
Loss before income tax expense	(133)	(85.2)	(411.2)	(229.7)
Income tax expense	0	0	0	0
Net loss	(133)	(85.2)	(411.2)	(229.7)
Other comprehensive income (loss):
Changes in net unrealized gains (losses) on investments	(0.5)	0.1	(4)	5
Comprehensive loss	$ (133.5)	$ (85.1)	$ (415.2)	$ (224.7)
Loss per common share: basic (both Class A and B) (in dollars per share)	$ (0.53)	$ (2.20)	$ (1.65)	$ (5.94)
Loss per common share: diluted (both Class A and B) (in dollars per share)	$ (0.53)	$ (2.20)	$ (1.65)	$ (5.94)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)	250.2	38.8	248.8	38.7
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)	250.2	38.8	248.8	38.7

CONDENSED CONSOLIDATED STATEM_2

CONDENSED CONSOLIDATED STATEMENTS OF REDEEMABLE CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS’ EQUITY (DEFICIT) - UNAUDITED - USD ($) shares in Millions, $ in Millions	Total	Class A and Class B Common Stock	Class A and Class B Common StockClass A Shares	Class A and Class B Common StockClass B Shares	Treasury Stock	Additional Paid-in Capital	Accumulated Other Comprehensive Income (Loss)	Accumulated Loss
Beginning balance (in shares) at Dec. 31, 2019	158.9
Beginning Balance at Dec. 31, 2019	$ 560.4
Increase (Decrease) in Temporary Equity [Roll Forward]
Tender offer and subsequent conversion (in shares)	2.9
Ending balance (in shares) at Sep. 30, 2020	161.8
Ending Balance at Sep. 30, 2020	$ 560.4
Beginning balance (in shares) at Dec. 31, 2019			0	44.4
Beginning balance at Dec. 31, 2019	(374)	$ 0			$ (0.1)	$ 10.5	$ 0.6	$ (385)
Treasury stock, beginning balance (in shares) at Dec. 31, 2019					4.5
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(229.7)							(229.7)
Changes in other comprehensive income (loss)	5						5
Tender offer and subsequent conversion (in shares)				2.9
Tender offer and subsequent conversion	25.1					25.1
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)				1.5
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	1.2					1.2
Reclassification of early-exercised stock option to liabilities (in shares)				(0.1)
Reclassification of early-exercised stock options to liabilities	0.3					0.3
Common stock—shared-based compensation expense	1.9					1.9
Settlement of related party loan (in shares)				(0.4)	0.1
Settlement of related party loan	(0.2)				$ (0.7)	0.5
Treasury stock, ending balance (in shares) at Sep. 30, 2020					4.6
Ending balance (in shares) at Sep. 30, 2020			0	42.5
Ending balance at Sep. 30, 2020	$ (570.4)	0			$ (0.8)	39.5	5.6	(614.7)
Beginning balance (in shares) at Jun. 30, 2020	161.8
Beginning Balance at Jun. 30, 2020	$ 560.4
Ending balance (in shares) at Sep. 30, 2020	161.8
Ending Balance at Sep. 30, 2020	$ 560.4
Beginning balance (in shares) at Jun. 30, 2020			0	41.4
Beginning balance at Jun. 30, 2020	(487.2)	0			$ (0.8)	37.6	5.5	(529.5)
Treasury stock, beginning balance (in shares) at Jun. 30, 2020					4.6
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(85.2)							(85.2)
Changes in other comprehensive income (loss)	0.1						0.1
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)				1
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	0.9					0.9
Reclassification of early-exercised stock option to liabilities (in shares)				0.1
Reclassification of early-exercised stock options to liabilities	0.2					0.2
Common stock—shared-based compensation expense	0.8					0.8
Treasury stock, ending balance (in shares) at Sep. 30, 2020					4.6
Ending balance (in shares) at Sep. 30, 2020			0	42.5
Ending balance at Sep. 30, 2020	$ (570.4)	0			$ (0.8)	39.5	5.6	(614.7)
Beginning balance (in shares) at Dec. 31, 2020	0
Beginning Balance at Dec. 31, 2020	$ 0
Ending balance (in shares) at Sep. 30, 2021	0
Ending Balance at Sep. 30, 2021	$ 0
Beginning balance (in shares) at Dec. 31, 2020			59.4	192.2
Beginning balance at Dec. 31, 2020	1,032.4	0			$ (0.8)	1,775.6	5.6	(748)
Treasury stock, beginning balance (in shares) at Dec. 31, 2020					4.6
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(411.2)							(411.2)
Changes in other comprehensive income (loss)	$ (4)						(4)
Conversion of Class B to Class A (in shares)			65.9	(65.9)
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares)	2.4		2.1	0.4
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes	$ 4.3					4.3
Reclassification of early-exercised stock option to liabilities (in shares)			(0.4)	(1.2)
Reclassification of early-exercised stock options to liabilities	(0.2)					(0.2)
Common stock—shared-based compensation expense	14.7					14.7
Treasury stock, ending balance (in shares) at Sep. 30, 2021					4.6
Ending balance (in shares) at Sep. 30, 2021			127	125.5
Ending balance at Sep. 30, 2021	$ 636	0			$ (0.8)	1,794.4	1.6	(1,159.2)
Beginning balance (in shares) at Jun. 30, 2021	0
Beginning Balance at Jun. 30, 2021	$ 0
Ending balance (in shares) at Sep. 30, 2021	0
Ending Balance at Sep. 30, 2021	$ 0
Beginning balance (in shares) at Jun. 30, 2021			114	139.7
Beginning balance at Jun. 30, 2021	762	0			$ (0.8)	1,786.9	2.1	(1,026.2)
Treasury stock, beginning balance (in shares) at Jun. 30, 2021					4.6
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(133)							(133)
Changes in other comprehensive income (loss)	(0.5)						(0.5)
Conversion of Class B to Class A (in shares)			13	(13)
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	0.9					0.9
Reclassification of early-exercised stock option to liabilities (in shares)			(0.1)	(1.2)
Reclassification of early-exercised stock options to liabilities	(0.9)					(0.9)
Common stock—shared-based compensation expense	7.5					7.5
Treasury stock, ending balance (in shares) at Sep. 30, 2021					4.6
Ending balance (in shares) at Sep. 30, 2021			127	125.5
Ending balance at Sep. 30, 2021	$ 636	$ 0			$ (0.8)	$ 1,794.4	$ 1.6	$ (1,159.2)

CONDENSED CONSOLIDATED STATEM_3

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - UNAUDITED - USD ($) $ in Millions	9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020
Cash flows from operating activities:
Net loss	$ (411.2)	$ (229.7)
Adjustments to reconcile net loss to net cash used in operating activities:
Share-based compensation	14.7	1.9
Tender offer	0	25.1
Depreciation and amortization	11	10.6
Bad debt expense	14.7	16.7
Warrants fair value adjustment	0	16
Payment-in-kind interest expense	9.3	6.8
Net realized gains on investments	(2.4)	(0.2)
Change in fair value of equity securities	(0.4)	0
Changes in operating assets and liabilities:
Premiums receivable	(60.4)	(32.4)
Reinsurance recoverable	(51.6)	(78.8)
Prepaid reinsurance premiums	(1.9)	(101.7)
Other assets	(1.6)	(8.1)
Losses and loss adjustment expenses reserves	63.5	84.6
Unearned premiums	53.8	19.7
Reinsurance premiums payable	(0.1)	140.7
Accounts payable and accrued expenses	(7.1)	31.6
Other liabilities	5.4	2.4
Net cash used in operating activities	(364.3)	(94.8)
Cash flows from investing activities:
Purchases of investments	(10.4)	(138.1)
Proceeds from maturities, call and pay downs of investments	30.6	31.2
Sales of investments	70.2	9.4
Capitalization of internally developed software	(4.8)	(3.9)
Purchases of fixed assets	(2.3)	(1.7)
Net cash provided by (used in) investing activities	83.3	(103.1)
Cash flows from financing activities:
Proceeds from exercise of stock options and restricted stock units, net of tax proceeds/(withholding)	3	1.4
Purchase of treasury stock	0	(0.2)
Proceeds from debt and warrants issuance, net of issuance costs	0	12.1
Repayments of long-term debt	(0.7)	(13.2)
Net cash provided by financing activities	2.3	0.1
Net decrease in cash, cash equivalents and restricted cash	(278.7)	(197.8)
Cash, cash equivalents and restricted cash at beginning of period	1,113.8	416.6
Cash, cash equivalents and restricted cash at end of period	$ 835.1	$ 218.8

NATURE OF BUSINESS

NATURE OF BUSINESS	9 Months Ended
	Sep. 30, 2021
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, a Delaware-domiciled insurance company; 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 a primarily direct-to-consumer model with the majority of our personal insurance customers acquired through mobile applications. 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	9 Months Ended
	Sep. 30, 2021
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, 2020 filed with the SEC on March 4, 2021, or the 2020 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, premium write-offs and valuation allowances for income taxes. COVID-19 —In March 2020, the World Health Organization declared COVID-19 to be a global pandemic. The pandemic and related measures taken to contain the spread of COVID-19, such as government-mandated business closures, orders to “shelter in place” and travel and transportation restrictions, have negatively affected the U.S. and global economies, disrupted global supply chains, and led to unprecedented levels of unemployment. We, and other businesses within the insurance industry, have been impacted by certain individual state bulletins that were issued in 2020 and outlined COVID-19 premium relief efforts, including restrictions on the ability to cancel policies for non-payment, requirements to defer insurance payments for up to 60 days and restrictions on increasing policy premiums. The COVID-19 pandemic has impacted and may further impact the broader economic environment, including negatively impacting unemployment levels, economic growth, the proper functioning of financial and capital markets and interest rates. As the COVID-19 pandemic continues, there is uncertainty around the severity and duration of the pandemic and the pandemic’s potential impact on our business and our financial performance. Accordingly, we cannot predict the impact that it may have on our future results of operations and financial condition. Reinsurance —In August 2021, we commenced a fronting arrangement with an unaffiliated Texas county mutual insurance company, or the fronting carrier. We route all of our new auto policies and, over time, expect to route certain renewal auto policies, in Texas through the fronting carrier and we assume 100% of the related premium and losses on those policies. The fronting arrangement allows us to have greater rating and underwriting flexibility. Premiums assumed are deferred and earned pro rata over the policy period. Unearned premium is established to cover the unexpired portion of premiums assumed. Commissions paid to the fronting carrier are capitalized as deferred acquisition costs and amortized over the same period in which the related premiums are earned. Assumed premiums and losses are subject to external reinsurance agreements. For additional information on our premiums, reinsurance, and policy acquisition cost accounting policies, please refer to our 2020 10-K. Recently Adopted Financial Accounting Standards —In February 2016, the Financial Accounting Standards Board, or FASB, issued Accounting Standards Update, or ASU, No. 2016-02, Leases (Topic 842) , or ASU 2016-02. The main provision of ASU 2016-02 requires the recognition of right-of-use lease assets and lease liabilities by lessees for those leases classified as operating leases under previous GAAP. The guidance also requires disclosures that meet the objective of enabling financial statement users to assess the amount, timing, and uncertainty of related cash flows. We adopted ASU 2016-02 on January 1, 2021. We elected various practical expedients which include: not applying the amended lease accounting guidance to comparative periods; including the carry forward of our leases without reassessing whether any contracts are leases or contain leases, lease classification and initial direct costs; and excluding leases with a term of 12 months or less from lease liability and right-of-use asset recognition. We did not elect the hindsight practical expedient. Our lease agreements contain lease components and non-lease components, both of which we have elected to account for as a single lease component for our real estate asset class. Operating lease expense for operating lease right-of-use assets is recognized on a straight-line basis over the lease term, which may include options to extend or terminate the lease when it is reasonably certain to do so and there is a significant economic incentive to exercise that option. Upon adoption of ASU 2016-02, we recognized an operating lease liability of $16.2 million and corresponding right-of-use asset of $9.9 million, which includes the effect of $6.3 million from reclassifying previously recognized deferred rent and lease exit liabilities as an offset, in accordance with the transition guidance. These lease assets and liabilities are recorded as other assets and other liabilities on the condensed consolidated balance sheets. This transition adjustment was reflected as a non-cash transaction in our condensed consolidated statements of cash flows. The transition did not have a material impact on our results of operations, liquidity or debt covenant compliance under our current debt agreements. For additional information refer to Note 7, “Leases.” Upcoming Accounting Pronouncements— We currently qualify as an "emerging growth company," or EGC, under the Jumpstart Our Business Startups Act of 2012, whereby we have the option to adopt new or revised accounting guidance within the same time periods as private companies. We have elected this option, but may ultimately determine it is preferable to take advantage of early adoption provisions offered within the applicable guidance. As of June 30, 2021, the market value of our common stock held by non-affiliates exceeded $700 million. Accordingly, we will follow the adoption criteria for public companies beginning December 31, 2021 and reflect such adoption criteria in our Annual Report on Form 10-K for the year ended December 31, 2021. In June 2016, the FASB issued ASU 2016-13, Financial Instruments—Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments

INVESTMENTS

INVESTMENTS	9 Months Ended
	Sep. 30, 2021
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 September 30, 2021 and December 31, 2020 are as follows: September 30, 2021 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 22.9 $ 0.1 $ (0.2) $ 22.8 Municipal securities 20.0 0.5 (0.1) 20.4 Corporate debt securities 48.7 1.0 (0.1) 49.6 Residential mortgage-backed securities 4.0 — — 4.0 Commercial mortgage backed securities 29.0 0.4 — 29.4 Other debt obligations 4.6 — — 4.6 Total $ 129.2 $ 2.0 $ (0.4) $ 130.8 December 31, 2020 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 16.9 $ 0.1 $ — $ 17.0 Municipal securities 22.6 0.8 — 23.4 Corporate debt securities 87.5 3.1 (0.1) 90.5 Residential mortgage-backed securities 7.8 — — 7.8 Commercial mortgage backed securities 57.1 1.3 — 58.4 Other debt obligations 23.5 0.4 — 23.9 Total fixed maturities 215.4 5.7 (0.1) 221.0 Short-term investments 3.0 — — 3.0 Total $ 218.4 $ 5.7 $ (0.1) $ 224.0 Other Investments Other investments consist of private equity investments without a readily determinable fair value. We elected to account for these investments at cost minus any impairment, plus or minus changes resulting from observable price changes in orderly transactions for an identical or a similar investment of the same issuer. As of September 30, 2021 and December 31, 2020, other investments were $1.3 million and $0.5 million, respectively. There were no impairments recognized on other investments for the three and nine months ended September 30, 2021 or 2020. The following tables reflect the gross unrealized losses and fair value of bonds, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at September 30, 2021 and December 31, 2020: September 30, 2021 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Bonds: U.S. Treasury securities and agencies $ 19.6 $ (0.2) $ — $ — $ 19.6 $ (0.2) Municipal securities 5.0 (0.1) — — 5.0 (0.1) Corporate debt securities 4.9 — 1.6 (0.1) 6.5 (0.1) Residential mortgage-backed securities 1.7 — 0.7 — 2.4 — Commercial mortgage-backed securities 3.7 — — — 3.7 — Total bonds $ 34.9 $ (0.3) $ 2.3 $ (0.1) $ 37.2 $ (0.4) December 31, 2020 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Bonds: U.S. Treasury securities and agencies $ 15.7 $ — $ — $ — $ 15.7 $ — Municipal securities 2.3 — — — 2.3 — Corporate debt securities 2.9 (0.1) — — 2.9 (0.1) Residential mortgage-backed securities 3.7 — — — 3.7 — Commercial mortgage-backed securities 4.9 — — — 4.9 — Other debt obligations 0.1 — — — 0.1 — Total bonds $ 29.6 $ (0.1) $ — $ — $ 29.6 $ (0.1) There were no other-than-temporary impairments recognized for the three and nine months ended September 30, 2021 or 2020. The following table reflects the gross and net realized gains and losses on short-term investments and fixed maturities that have been included in the condensed consolidated statements of operations and comprehensive loss for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Realized gains on investments $ — $ 0.2 $ 2.5 $ 0.3 Realized losses on investments — (0.1) (0.1) (0.1) Net realized gains on investments $ — $ 0.1 $ 2.4 $ 0.2 The following table sets forth the amortized cost and fair value of short-term investments and fixed maturity securities by contractual maturity at September 30, 2021: September 30, 2021 Amortized Cost Fair Value (dollars in millions) Due in one year or less $ 18.1 $ 17.8 Due after one year through five years 90.1 91.8 Due five years through 10 years 5.0 5.0 Due after 10 years 16.0 16.2 Total $ 129.2 $ 130.8 The following table sets forth the components of net investment income for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Interest on bonds $ 0.6 $ 1.1 $ 1.9 $ 3.2 Interest on deposits and cash equivalents 0.2 0.1 0.8 1.4 Other investments 0.4 — 0.4 — Total 1.2 1.2 3.1 4.6 Investment expense (0.2) (0.1) (0.5) (0.3) Net investment income $ 1.0 $ 1.1 $ 2.6 $ 4.3 The following tables summarize the credit ratings of investments at September 30, 2021 and December 31, 2020: September 30, 2021 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 70.2 $ 70.6 54.0 % AA+, AA, AA-, A-1 14.7 15.0 11.5 A+, A, A- 34.3 34.9 26.7 BBB+, BBB, BBB- 10.0 10.3 7.8 Total $ 129.2 $ 130.8 100.0 % December 31, 2020 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 116.5 $ 118.7 53.0 % AA+, AA, AA-, A-1 22.7 23.3 10.4 A+, A, A- 57.5 59.4 26.5 BBB+, BBB, BBB- 21.7 22.6 10.1 Total $ 218.4 $ 224.0 100.0 %

FAIR VALUE OF FINANCIAL INSTRUM

FAIR VALUE OF FINANCIAL INSTRUMENTS	9 Months Ended
	Sep. 30, 2021
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 September 30, 2021 and December 31, 2020: September 30, 2021 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 22.8 $ — $ — $ 22.8 Municipal securities — 20.4 — 20.4 Corporate debt securities — 49.6 — 49.6 Residential mortgage-backed securities — 4.0 — 4.0 Commercial mortgage-backed securities — 29.4 — 29.4 Other debt obligations — 4.6 — 4.6 Total fixed maturities 22.8 108.0 — 130.8 Cash equivalents 208.7 — — 208.7 Total assets at fair value $ 231.5 $ 108.0 $ — $ 339.5 December 31, 2020 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 17.0 $ — $ — $ 17.0 Municipal securities — 23.4 — 23.4 Corporate debt securities — 90.5 — 90.5 Residential mortgage-backed securities — 7.8 — 7.8 Commercial mortgage-backed securities — 58.4 — 58.4 Other debt obligations — 23.9 — 23.9 Total fixed maturities 17.0 204.0 — 221.0 Short-term investments 2.2 0.8 — 3.0 Cash equivalents 568.4 — — 568.4 Total assets at fair value $ 587.6 $ 204.8 $ — $ 792.4 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. The carrying amount of long-term debt is recorded at historical amounts. 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 September 30, 2021 and December 31, 2020, the carrying amounts and fair values of these financial instruments were as follows: Carrying Amount as of September 30, 2021 Estimated Fair Value as of September 30, 2021 Carrying Amount as of December 31, 2020 Estimated Fair Value as of December 31, 2020 (dollars in millions) Long-term debt $ 201.7 $ 218.3 $ 188.2 $ 209.0

LOSS AND LOSS ADJUSTMENT EXPENS

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES	9 Months Ended
	Sep. 30, 2021
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: Nine Months Ended September 30, 2021 2020 (dollars in millions) Gross loss and LAE reserves, January 1 $ 237.2 $ 140.7 Reinsurance recoverable on unpaid losses (79.6) (18.9) Net loss and LAE reserves, January 1 157.6 121.8 Net incurred loss and LAE related to: Current year 293.8 282.0 Prior years (9.3) 21.3 Total incurred 284.5 303.3 Net paid loss and LAE related to: Current year 150.4 165.8 Prior years 72.6 100.4 Total paid 223.0 266.2 Net loss and LAE reserves, September 30 219.1 158.9 Plus reinsurance recoverable on unpaid losses 81.6 66.4 Gross loss and LAE reserves, September 30 $ 300.7 $ 225.3 Incurred losses and LAE attributable to prior accident years was a decrease of $9.3 million and an increase of $21.3 million for the nine months ended September 30, 2021 and 2020, respectively. For the nine months ended September 30, 2021, the development of incurred losses related to prior periods was primarily related to lower-than-expected reported losses on bodily injury claims, and higher than expected recoveries from subrogation and salvage from 2020 material damage claims. For the nine months ended September 30, 2020, the development of incurred losses related to prior periods was primarily related to higher-than-expected reported losses on bodily injury and collision coverages from 2019. This period also includes adjustments recorded in order to effectuate management’s best estimate for determining the estimated ultimate cost of settling claims using our knowledge and experience about past and current events and developments.

REINSURANCE

REINSURANCE	9 Months Ended
	Sep. 30, 2021
Insurance [Abstract]
REINSURANCE	REINSURANCE The following table reflects amounts affecting the condensed consolidated balance sheets and statements of operations and comprehensive loss for reinsurance as of and for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Premiums written: Direct $ 197.0 $ 164.6 $ 576.6 $ 471.1 Assumed 7.6 — 7.6 — Ceded (107.5) (189.1) (306.8) (274.7) Net premiums written $ 97.1 $ (24.5) $ 277.4 $ 196.4 Premiums earned: Direct $ 188.5 $ 154.4 $ 529.4 $ 450.2 Assumed 0.9 — 0.9 — Ceded (104.3) (109.5) (304.9) (171.8) Net premiums earned $ 85.1 $ 44.9 $ 225.4 $ 278.4 Losses and LAE incurred: Direct $ 193.7 $ 153.9 $ 504.6 $ 422.9 Assumed 1.9 — 1.9 — Ceded (81.2) (77.8) (222.0) (119.6) Net losses and LAE incurred $ 114.4 $ 76.1 $ 284.5 $ 303.3 Gross written premium, by state is as follows for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 Amount % of Total Amount % of Total Amount % of Total Amount % of Total State (dollars in millions) Texas (1) $ 40.4 19.7 % $ 35.2 21.4 % $ 120.8 20.7 % $ 100.4 21.3 % Georgia 21.6 10.6 18.8 11.4 61.3 10.5 56.4 12.0 Louisiana 12.3 6.0 8.0 4.9 32.9 5.6 20.6 4.4 Pennsylvania 11.8 5.8 7.9 4.8 31.5 5.4 23.1 4.9 Nevada 9.5 4.6 5.8 3.5 26.0 4.5 13.3 2.8 Colorado 9.3 4.5 5.8 3.5 25.7 4.4 14.3 3.0 Utah 9.1 4.4 6.9 4.2 25.6 4.4 19.1 4.1 South Carolina 8.0 3.9 2.1 1.3 20.6 3.5 6.3 1.3 Arizona 6.4 3.1 7.9 4.8 19.1 3.3 22.9 4.9 Missouri 6.3 3.1 7.5 4.6 19.7 3.4 21.1 4.5 All others states 69.9 34.3 58.7 35.6 201.0 34.3 173.6 36.8 Total $ 204.6 100.0 % $ 164.6 100.0 % $ 584.2 100.0 % $ 471.1 100.0 % ______________ (1) Includes automobile insurance premiums assumed under quota share agreement with an unaffiliated Texas county mutual insurance company, whereby we assume 100% of the written premium. See Note 6, “Reinsurance,” for additional information regarding gross premiums.

LEASES

LEASES	9 Months Ended
	Sep. 30, 2021
Leases [Abstract]
LEASES	LEASES We primarily have operating leases for offices that support our corporate, claims and customer service functions. We determine if an arrangement is a lease at inception by evaluating whether the arrangement conveys the right to use an identified asset and whether we obtain substantially all of the economic benefits from and have the ability to direct the use of the asset. Our lease agreements do not contain any material residual value guarantees or material restrictive covenants. Operating lease right-of-use assets and corresponding operating lease liabilities are recognized upon the commencement date based primarily on the present value of lease payments over the lease term. We use the implicit rate of the lease, if it is readily determinable, in determining the present value of lease payments. Our leases generally do not provide an implicit rate. Therefore, we use a collateralized incremental borrowing rate that incorporates information available at commencement date, including our company-specific interest rates from recent debt issuances, which we adjust to remove the LIBOR component in order to obtain our company-specific interest rate risk. We also leverage commercial mortgage-backed securities, or CMBS, rates, for transactions with similar values, origination dates, geographies and property types as the respective lease, which are adjusted using linear interpolation if the lease term falls between the published CMBS terms. As of September 30, 2021, our leases had a weighted-average discount rate of 10.8%. Our leases have remaining lease terms from approximately one year up to approximately six years with a weighted-average remaining lease term of 4.6 years as of September 30, 2021. As of September 30, 2021, we recognized an operating lease liability of $14.7 million and corresponding right-of-use asset of $9.0 million. Operating lease liabilities are included in other liabilities other assets We also sublease certain office space, resulting in sublease income. Sublease income and the related assets and cash flows are not material to our condensed consolidated financial statements as of and for the three and nine months ended September 30, 2021. Sublease income is recognized as a reduction to operating lease expense in our condensed consolidated statements of operations and comprehensive loss. Future lease payments as of September 30, 2021 were as follows: Operating Leases (dollars in millions) Remainder of 2021 $ 1.0 2022 4.3 2023 4.4 2024 4.3 2025 1.5 2026 and thereafter 3.1 Total future lease payments 18.6 Less: imputed interest (3.9) Total lease liabilities $ 14.7 As previously disclosed in our 2020 10-K under the prior lease accounting guidance, the following table summarizes, by remaining maturity, future commitments related to operating leases and other arrangements as of December 31, 2020: Operating Leases (dollars in millions) 2021 $ 3.9 2022 4.4 2023 4.4 2024 4.3 2025 1.5 2026 and thereafter 3.1 Total $ 21.6

LONG-TERM DEBT

LONG-TERM DEBT	9 Months Ended
	Sep. 30, 2021
Debt Disclosure [Abstract]
LONG-TERM DEBT	LONG-TERM DEBT Term Loan A was a term loan outstanding with a group of syndicated financial institutions as of September 30, 2021, which matured on October 15, 2021. For additional information refer to Note 15, “Subsequent Events.” Interest was paid monthly and was determined on a floating interest rate calculated on the one-month LIBOR plus an applicable margin of 4%. As a part of the amended Term Loan A, the syndicate committed, pro rata, to a $100 million revolving loan, which also expired on October 15, 2021. Commitment fees accrued at 0.50% per annum on the daily amount of unused revolving loan and was paid quarterly. For any amounts drawn on the revolving loan, interest accrued and was paid consistent with Term Loan A. In addition, there was a letter of credit fee of 4% per annum on the average daily amount of issued letters of credit against the revolver and a 0.125% per annum fronting fee based on the average daily amount of letter of credit exposure. We had no letters of credit outstanding or amounts drawn against the revolving loan as of September 30, 2021. Term Loan B was a note we issued to a private equity investor that had a maturity date of November 25, 2024. We repaid Term Loan B on November 8, 2021. For additional information refer to Note 15, “Subsequent Events.” Interest was determined on a floating interest rate calculated on the three-month LIBOR plus an applicable margin of 10.5%. We paid interest pursuant to the terms of the loan agreements and had the option to pay-in-kind, or PIK, on Term Loan B until October 15, 2021. PIK interest was added to the principal balance every three months until we no longer PIK interest, at which point interest would be paid quarterly. We elected to PIK interest on Term Loan B from the original date of closing through September 30, 2021. Deferred PIK interest was $3.5 million and $2.3 million for the three months ended September 30, 2021 and 2020, respectively. Deferred PIK interest was $9.3 million and $6.8 million for the nine months ended September 30, 2021 and 2020, respectively. Deferred PIK interest is recognized as interest expense in the condensed consolidated statements of operations and comprehensive loss. The following summarizes the carrying value of long-term debt as of September 30, 2021 and December 31, 2020: September 30, 2021 December 31, 2020 (dollars in millions) Term Loan A $ 98.8 $ 99.5 Term Loan B 100.0 100.0 Total 198.8 199.5 Accrued interest payable 19.3 10.2 Unamortized discount and debt issuance costs (16.4) (21.5) Total $ 201.7 $ 188.2

INCOME TAXES

INCOME TAXES	9 Months Ended
	Sep. 30, 2021
Income Tax Disclosure [Abstract]
INCOME TAXES	INCOME TAXES The consolidated effective tax rate was zero for the three and nine months ended September 30, 2021 and 2020. 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 September 30, 2021 and December 31, 2020, we did not have any unrecognized tax benefits for uncertain tax positions and had no interest or penalties related to uncertain tax positions.

SHARE-BASED COMPENSATION

SHARE-BASED COMPENSATION	9 Months Ended
	Sep. 30, 2021
Share-based Payment Arrangement [Abstract]
SHARE-BASED COMPENSATION	SHARE-BASED COMPENSATION We maintain an equity incentive plan, the 2020 Equity Incentive Plan, or the 2020 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 September 30, 2021, we had 22.2 million common shares authorized and available for issuance under the 2020 Plan. The following table displays share-based compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Share-based compensation expense: Loss and loss adjustment expenses $ — $ — $ 0.6 $ 0.5 Sales and marketing 0.4 — 0.6 1.0 Other insurance expense 0.4 — 0.9 1.0 Technology and development 2.9 0.2 4.7 5.4 General and administrative 3.8 0.6 7.9 19.1 Total share-based compensation expense $ 7.5 $ 0.8 $ 14.7 $ 27.0 The following table provides total share-based compensation expense by type of award: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Share-based compensation expense: Restricted stock unit expense $ 6.1 $ — $ 10.9 $ — Stock option expense 1.4 0.8 3.8 27.0 Total share-based compensation expense $ 7.5 $ 0.8 $ 14.7 $ 27.0 In March 2020, a current investor completed a tender offer for vested common stock from shareholders, many of whom were employees or members of the Board of Directors. To encourage participation, the tender offer was made at a price in excess of the fair value of our common stock. As a result, we recognized $25.1 million of share-based compensation expense during the nine months ended September 30, 2020. As of September 30, 2021, there was $5.7 million and $81.7 million of unrecognized compensation cost related to nonvested stock options and RSUs, respectively. The remaining costs are expected to be recognized over a period of approximately five Restricted Stock Units A summary of RSU activity for the nine months ended September 30, 2021 is as follows: Nine Months Ended September 30, 2021 Restricted Stock Units Number of Shares Weighted-Average Aggregate Intrinsic Value (in millions, except per share amounts) Nonvested at January 1, 2021 0.4 $ 18.41 $ 6.2 Granted 8.9 10.71 Vested (0.1) 15.77 0.7 Forfeited, expired or canceled (0.8) 11.79 Nonvested at September 30, 2021 8.4 $ 10.93 $ 44.6 Stock Options A summary of option activity for the nine months ended September 30, 2021 is as follows: Nine Months Ended September 30, 2021 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, 2021 10.4 $ 2.39 7.75 $ 137.7 Granted — 10.82 Exercised (2.4) 1.88 23.4 Forfeited, expired or canceled (1.0) 4.71 Outstanding and exercisable at September 30, 2021 7.0 $ 2.28 6.93 $ 23.7

COMMITMENTS AND CONTINGENCIES

COMMITMENTS AND CONTINGENCIES	9 Months Ended
	Sep. 30, 2021
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 March 19, 2021, a purported class action complaint was filed against the Company and certain of its current 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 Securities Exchange Act of 1934 and Rule 10b-5 thereunder, and of Sections 11 and 15 of the Securities Act of 1933, 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 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 INCOME AND

OTHER COMPREHENSIVE INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME	9 Months Ended
	Sep. 30, 2021
Equity [Abstract]
OTHER COMPREHENSIVE INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME	OTHER COMPREHENSIVE INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME The following table presents the changes in our accumulated other comprehensive income, or AOCI, for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Change in net unrealized gains (losses) on investments: Accumulated other comprehensive income beginning balance $ 2.1 $ 5.5 $ 5.6 $ 0.6 Other comprehensive income (loss) before reclassifications (0.5) 0.2 (1.6) 5.2 Net realized gains on investments reclassified from AOCI to net loss — (0.1) (2.4) (0.2) Net current period other comprehensive income (loss) (0.5) 0.1 (4.0) 5.0 Accumulated other comprehensive income ending balance $ 1.6 $ 5.6 $ 1.6 $ 5.6

LOSS PER SHARE

LOSS PER SHARE	9 Months Ended
	Sep. 30, 2021
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 nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (in millions, except per share amounts) Net loss $ (133.0) $ (85.2) $ (411.2) $ (229.7) Weighted-average common shares outstanding: basic and diluted (both Class A and B) 250.2 38.8 248.8 38.7 Loss per common share: basic and diluted (both Class A and B) $ (0.53) $ (2.20) $ (1.65) $ (5.94) We excluded the following potential common shares, presented based on amounts outstanding at each period end, from the computation of diluted net loss per share attributable to common shareholders for the periods indicated because including them would have had an anti-dilutive effect: As of September 30, 2021 2020 (in millions) Options to purchase common stock 7.0 11.6 Nonvested shares subject to repurchase 2.3 5.3 Restricted stock units 8.4 0.1 Redeemable convertible preferred stock (as converted to common stock) — 161.8 Warrants to purchase redeemable convertible preferred stock (as converted to common stock) — 0.6 Total 17.7 179.4

GEOGRAPHICAL BREAKDOWN OF GROSS

GEOGRAPHICAL BREAKDOWN OF GROSS WRITTEN PREMIUM	9 Months Ended
	Sep. 30, 2021
Insurance [Abstract]
GEOGRAPHICAL BREAKDOWN OF GROSS WRITTEN PREMIUM	REINSURANCE The following table reflects amounts affecting the condensed consolidated balance sheets and statements of operations and comprehensive loss for reinsurance as of and for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Premiums written: Direct $ 197.0 $ 164.6 $ 576.6 $ 471.1 Assumed 7.6 — 7.6 — Ceded (107.5) (189.1) (306.8) (274.7) Net premiums written $ 97.1 $ (24.5) $ 277.4 $ 196.4 Premiums earned: Direct $ 188.5 $ 154.4 $ 529.4 $ 450.2 Assumed 0.9 — 0.9 — Ceded (104.3) (109.5) (304.9) (171.8) Net premiums earned $ 85.1 $ 44.9 $ 225.4 $ 278.4 Losses and LAE incurred: Direct $ 193.7 $ 153.9 $ 504.6 $ 422.9 Assumed 1.9 — 1.9 — Ceded (81.2) (77.8) (222.0) (119.6) Net losses and LAE incurred $ 114.4 $ 76.1 $ 284.5 $ 303.3 Gross written premium, by state is as follows for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 Amount % of Total Amount % of Total Amount % of Total Amount % of Total State (dollars in millions) Texas (1) $ 40.4 19.7 % $ 35.2 21.4 % $ 120.8 20.7 % $ 100.4 21.3 % Georgia 21.6 10.6 18.8 11.4 61.3 10.5 56.4 12.0 Louisiana 12.3 6.0 8.0 4.9 32.9 5.6 20.6 4.4 Pennsylvania 11.8 5.8 7.9 4.8 31.5 5.4 23.1 4.9 Nevada 9.5 4.6 5.8 3.5 26.0 4.5 13.3 2.8 Colorado 9.3 4.5 5.8 3.5 25.7 4.4 14.3 3.0 Utah 9.1 4.4 6.9 4.2 25.6 4.4 19.1 4.1 South Carolina 8.0 3.9 2.1 1.3 20.6 3.5 6.3 1.3 Arizona 6.4 3.1 7.9 4.8 19.1 3.3 22.9 4.9 Missouri 6.3 3.1 7.5 4.6 19.7 3.4 21.1 4.5 All others states 69.9 34.3 58.7 35.6 201.0 34.3 173.6 36.8 Total $ 204.6 100.0 % $ 164.6 100.0 % $ 584.2 100.0 % $ 471.1 100.0 % ______________ (1) Includes automobile insurance premiums assumed under quota share agreement with an unaffiliated Texas county mutual insurance company, whereby we assume 100% of the written premium. See Note 6, “Reinsurance,” for additional information regarding gross premiums.

SUBSEQUENT EVENTS

SUBSEQUENT EVENTS	9 Months Ended
	Sep. 30, 2021
Subsequent Events [Abstract]
SUBSEQUENT EVENTS	SUBSEQUENT EVENTS On October 1, 2021, we closed the convertible preferred equity investment by Carvana pursuant to the investment agreement that we entered into with Carvana on August 11, 2021, or the Investment Agreement. We received approximately $126 million of gross proceeds from the issuance of convertible preferred stock designated as the Series A Convertible Preferred Stock and issued Carvana eight tranches of warrants to purchase shares of the Company’s Class A common stock. As part of the investment agreement, we and Carvana entered into a five-year commercial agreement whereby our telematics-based auto insurance products will be embedded into Carvana’s online car buying platform, or Integrated Platform. The commercial arrangement provides for agent commissions payable to Carvana for policy origination and an enterprise total loss replacement vehicle solution. We issued to Carvana approximately 14 million shares of preferred stock that is initially convertible into approximately 14 million Class A shares of Root based on an initial liquidation preference of $9.00 per share. In connection with this issuance, we filed a Certificate of Designations that established the rights and restrictions of the preferred stock, including that it will become convertible or redeemable at the option of the preferred stockholder in connection with any change of control of the Company, which is considered not solely within our control. Accordingly, the preferred stock issued to Carvana will be classified as mezzanine equity. Concurrent with the convertible preferred equity investment, we issued Carvana eight tranches of warrants, comprised of three tranches of “short-term warrants” and five tranches of “long-term warrants”. The short-term warrants will expire three years following the earlier of the date of completion of the Integrated Platform and 18 months following closing of the Investment Agreement, such earlier date, the Reference Date, and the long-term warrants will expire five years after the Reference Date. The short-term warrants have exercise prices of $10.00 to $12.00 and the long-term warrants have exercise prices of $10.00 to $30.00. The warrants will be subject to certain conditions to exercise, including relating to the achievement of defined milestones tied to the development of the Integrated Platform and insurance sales through the Integrated Platform. If the warrants are fully exercised by Carvana for cash, Carvana will have the opportunity to purchase approximately 129 million shares of Class A Common Stock, representing 29.9% of the aggregate number of issued and outstanding shares of our common stock on a fully-diluted basis as of August 11, 2021. In connection with the Investment Agreement, we incurred issuance costs of approximately $20 million, $9 million of which are contingent upon the success of the Investment Agreement as measured by achievement of certain warrant vesting milestones. As of September 30, 2021, these costs were accrued for in other assets, other liabilities and accounts payable and accrued expenses on our condensed consolidated balance sheets. On October 15, 2021, upon the maturity of Term Loan A and expiration of the related revolving loan, we repaid the outstanding Term Loan A principal balance of $98.8 million and accrued interest and fees of $0.2 million. On November 8, 2021, we repaid the outstanding Term Loan B principal balance of $100.0 million and accrued interest, including PIK interest, and fees of $20.9 million. As of September 30, 2021, we had unamortized discount and debt issuance costs of $16.4 million. Upon repayment, any unamortized costs will be recognized as interest expense in our consolidated statements of operations for the year ended December 31, 2021.

Accounting Policies (Policies)

Accounting Policies (Policies)	9 Months Ended
	Sep. 30, 2021
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, 2020 filed with the SEC on March 4, 2021, or the 2020 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.
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, premium write-offs and valuation allowances for income taxes.
Reinsurance	Reinsurance —In August 2021, we commenced a fronting arrangement with an unaffiliated Texas county mutual insurance company, or the fronting carrier. We route all of our new auto policies and, over time, expect to route certain renewal auto policies, in Texas through the fronting carrier and we assume 100% of the related premium and losses on those policies. The fronting arrangement allows us to have greater rating and underwriting flexibility. Premiums assumed are deferred and earned pro rata over the policy period. Unearned premium is established to cover the unexpired portion of premiums assumed. Commissions paid to the fronting carrier are
Recently Adopted Financial Accounting Standards/Upcoming Accounting Pronouncements	Recently Adopted Financial Accounting Standards —In February 2016, the Financial Accounting Standards Board, or FASB, issued Accounting Standards Update, or ASU, No. 2016-02, Leases (Topic 842) , or ASU 2016-02. The main provision of ASU 2016-02 requires the recognition of right-of-use lease assets and lease liabilities by lessees for those leases classified as operating leases under previous GAAP. The guidance also requires disclosures that meet the objective of enabling financial statement users to assess the amount, timing, and uncertainty of related cash flows. We adopted ASU 2016-02 on January 1, 2021. We elected various practical expedients which include: not applying the amended lease accounting guidance to comparative periods; including the carry forward of our leases without reassessing whether any contracts are leases or contain leases, lease classification and initial direct costs; and excluding leases with a term of 12 months or less from lease liability and right-of-use asset recognition. We did not elect the hindsight practical expedient. Our lease agreements contain lease components and non-lease components, both of which we have elected to account for as a single lease component for our real estate asset class. Operating lease expense for operating lease right-of-use assets is recognized on a straight-line basis over the lease term, which may include options to extend or terminate the lease when it is reasonably certain to do so and there is a significant economic incentive to exercise that option. Upon adoption of ASU 2016-02, we recognized an operating lease liability of $16.2 million and corresponding right-of-use asset of $9.9 million, which includes the effect of $6.3 million from reclassifying previously recognized deferred rent and lease exit liabilities as an offset, in accordance with the transition guidance. These lease assets and liabilities are recorded as other assets and other liabilities on the condensed consolidated balance sheets. This transition adjustment was reflected as a non-cash transaction in our condensed consolidated statements of cash flows. The transition did not have a material impact on our results of operations, liquidity or debt covenant compliance under our current debt agreements. For additional information refer to Note 7, “Leases.” Upcoming Accounting Pronouncements— We currently qualify as an "emerging growth company," or EGC, under the Jumpstart Our Business Startups Act of 2012, whereby we have the option to adopt new or revised accounting guidance within the same time periods as private companies. We have elected this option, but may ultimately determine it is preferable to take advantage of early adoption provisions offered within the applicable guidance. As of June 30, 2021, the market value of our common stock held by non-affiliates exceeded $700 million. Accordingly, we will follow the adoption criteria for public companies beginning December 31, 2021 and reflect such adoption criteria in our Annual Report on Form 10-K for the year ended December 31, 2021. In June 2016, the FASB issued ASU 2016-13, Financial Instruments—Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments

INVESTMENTS (Tables)

INVESTMENTS (Tables)	9 Months Ended
	Sep. 30, 2021
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 September 30, 2021 and December 31, 2020 are as follows: September 30, 2021 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 22.9 $ 0.1 $ (0.2) $ 22.8 Municipal securities 20.0 0.5 (0.1) 20.4 Corporate debt securities 48.7 1.0 (0.1) 49.6 Residential mortgage-backed securities 4.0 — — 4.0 Commercial mortgage backed securities 29.0 0.4 — 29.4 Other debt obligations 4.6 — — 4.6 Total $ 129.2 $ 2.0 $ (0.4) $ 130.8 December 31, 2020 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 16.9 $ 0.1 $ — $ 17.0 Municipal securities 22.6 0.8 — 23.4 Corporate debt securities 87.5 3.1 (0.1) 90.5 Residential mortgage-backed securities 7.8 — — 7.8 Commercial mortgage backed securities 57.1 1.3 — 58.4 Other debt obligations 23.5 0.4 — 23.9 Total fixed maturities 215.4 5.7 (0.1) 221.0 Short-term investments 3.0 — — 3.0 Total $ 218.4 $ 5.7 $ (0.1) $ 224.0 The following table reflects the gross and net realized gains and losses on short-term investments and fixed maturities that have been included in the condensed consolidated statements of operations and comprehensive loss for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Realized gains on investments $ — $ 0.2 $ 2.5 $ 0.3 Realized losses on investments — (0.1) (0.1) (0.1) Net realized gains on investments $ — $ 0.1 $ 2.4 $ 0.2 The following table sets forth the amortized cost and fair value of short-term investments and fixed maturity securities by contractual maturity at September 30, 2021: September 30, 2021 Amortized Cost Fair Value (dollars in millions) Due in one year or less $ 18.1 $ 17.8 Due after one year through five years 90.1 91.8 Due five years through 10 years 5.0 5.0 Due after 10 years 16.0 16.2 Total $ 129.2 $ 130.8
Schedule of unrealized losses	The following tables reflect the gross unrealized losses and fair value of bonds, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at September 30, 2021 and December 31, 2020: September 30, 2021 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Bonds: U.S. Treasury securities and agencies $ 19.6 $ (0.2) $ — $ — $ 19.6 $ (0.2) Municipal securities 5.0 (0.1) — — 5.0 (0.1) Corporate debt securities 4.9 — 1.6 (0.1) 6.5 (0.1) Residential mortgage-backed securities 1.7 — 0.7 — 2.4 — Commercial mortgage-backed securities 3.7 — — — 3.7 — Total bonds $ 34.9 $ (0.3) $ 2.3 $ (0.1) $ 37.2 $ (0.4) December 31, 2020 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Bonds: U.S. Treasury securities and agencies $ 15.7 $ — $ — $ — $ 15.7 $ — Municipal securities 2.3 — — — 2.3 — Corporate debt securities 2.9 (0.1) — — 2.9 (0.1) Residential mortgage-backed securities 3.7 — — — 3.7 — Commercial mortgage-backed securities 4.9 — — — 4.9 — Other debt obligations 0.1 — — — 0.1 — Total bonds $ 29.6 $ (0.1) $ — $ — $ 29.6 $ (0.1)
Schedule of net investment income	The following table sets forth the components of net investment income for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Interest on bonds $ 0.6 $ 1.1 $ 1.9 $ 3.2 Interest on deposits and cash equivalents 0.2 0.1 0.8 1.4 Other investments 0.4 — 0.4 — Total 1.2 1.2 3.1 4.6 Investment expense (0.2) (0.1) (0.5) (0.3) Net investment income $ 1.0 $ 1.1 $ 2.6 $ 4.3
Schedule of credit ratings	The following tables summarize the credit ratings of investments at September 30, 2021 and December 31, 2020: September 30, 2021 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 70.2 $ 70.6 54.0 % AA+, AA, AA-, A-1 14.7 15.0 11.5 A+, A, A- 34.3 34.9 26.7 BBB+, BBB, BBB- 10.0 10.3 7.8 Total $ 129.2 $ 130.8 100.0 % December 31, 2020 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 116.5 $ 118.7 53.0 % AA+, AA, AA-, A-1 22.7 23.3 10.4 A+, A, A- 57.5 59.4 26.5 BBB+, BBB, BBB- 21.7 22.6 10.1 Total $ 218.4 $ 224.0 100.0 %

FAIR VALUE OF FINANCIAL INSTR_2

FAIR VALUE OF FINANCIAL INSTRUMENTS (Tables)	9 Months Ended
	Sep. 30, 2021
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 September 30, 2021 and December 31, 2020: September 30, 2021 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 22.8 $ — $ — $ 22.8 Municipal securities — 20.4 — 20.4 Corporate debt securities — 49.6 — 49.6 Residential mortgage-backed securities — 4.0 — 4.0 Commercial mortgage-backed securities — 29.4 — 29.4 Other debt obligations — 4.6 — 4.6 Total fixed maturities 22.8 108.0 — 130.8 Cash equivalents 208.7 — — 208.7 Total assets at fair value $ 231.5 $ 108.0 $ — $ 339.5 December 31, 2020 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 17.0 $ — $ — $ 17.0 Municipal securities — 23.4 — 23.4 Corporate debt securities — 90.5 — 90.5 Residential mortgage-backed securities — 7.8 — 7.8 Commercial mortgage-backed securities — 58.4 — 58.4 Other debt obligations — 23.9 — 23.9 Total fixed maturities 17.0 204.0 — 221.0 Short-term investments 2.2 0.8 — 3.0 Cash equivalents 568.4 — — 568.4 Total assets at fair value $ 587.6 $ 204.8 $ — $ 792.4
Schedule of carrying amounts and fair values of financial instruments	As of September 30, 2021 and December 31, 2020, the carrying amounts and fair values of these financial instruments were as follows: Carrying Amount as of September 30, 2021 Estimated Fair Value as of September 30, 2021 Carrying Amount as of December 31, 2020 Estimated Fair Value as of December 31, 2020 (dollars in millions) Long-term debt $ 201.7 $ 218.3 $ 188.2 $ 209.0

LOSS AND LOSS ADJUSTMENT EXPE_2

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Tables)	9 Months Ended
	Sep. 30, 2021
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: Nine Months Ended September 30, 2021 2020 (dollars in millions) Gross loss and LAE reserves, January 1 $ 237.2 $ 140.7 Reinsurance recoverable on unpaid losses (79.6) (18.9) Net loss and LAE reserves, January 1 157.6 121.8 Net incurred loss and LAE related to: Current year 293.8 282.0 Prior years (9.3) 21.3 Total incurred 284.5 303.3 Net paid loss and LAE related to: Current year 150.4 165.8 Prior years 72.6 100.4 Total paid 223.0 266.2 Net loss and LAE reserves, September 30 219.1 158.9 Plus reinsurance recoverable on unpaid losses 81.6 66.4 Gross loss and LAE reserves, September 30 $ 300.7 $ 225.3

REINSURANCE (Tables)

REINSURANCE (Tables)	9 Months Ended
	Sep. 30, 2021
Insurance [Abstract]
Schedule of Comprehensive Loss for Reinsurance	The following table reflects amounts affecting the condensed consolidated balance sheets and statements of operations and comprehensive loss for reinsurance as of and for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Premiums written: Direct $ 197.0 $ 164.6 $ 576.6 $ 471.1 Assumed 7.6 — 7.6 — Ceded (107.5) (189.1) (306.8) (274.7) Net premiums written $ 97.1 $ (24.5) $ 277.4 $ 196.4 Premiums earned: Direct $ 188.5 $ 154.4 $ 529.4 $ 450.2 Assumed 0.9 — 0.9 — Ceded (104.3) (109.5) (304.9) (171.8) Net premiums earned $ 85.1 $ 44.9 $ 225.4 $ 278.4 Losses and LAE incurred: Direct $ 193.7 $ 153.9 $ 504.6 $ 422.9 Assumed 1.9 — 1.9 — Ceded (81.2) (77.8) (222.0) (119.6) Net losses and LAE incurred $ 114.4 $ 76.1 $ 284.5 $ 303.3 Gross written premium, by state is as follows for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 Amount % of Total Amount % of Total Amount % of Total Amount % of Total State (dollars in millions) Texas (1) $ 40.4 19.7 % $ 35.2 21.4 % $ 120.8 20.7 % $ 100.4 21.3 % Georgia 21.6 10.6 18.8 11.4 61.3 10.5 56.4 12.0 Louisiana 12.3 6.0 8.0 4.9 32.9 5.6 20.6 4.4 Pennsylvania 11.8 5.8 7.9 4.8 31.5 5.4 23.1 4.9 Nevada 9.5 4.6 5.8 3.5 26.0 4.5 13.3 2.8 Colorado 9.3 4.5 5.8 3.5 25.7 4.4 14.3 3.0 Utah 9.1 4.4 6.9 4.2 25.6 4.4 19.1 4.1 South Carolina 8.0 3.9 2.1 1.3 20.6 3.5 6.3 1.3 Arizona 6.4 3.1 7.9 4.8 19.1 3.3 22.9 4.9 Missouri 6.3 3.1 7.5 4.6 19.7 3.4 21.1 4.5 All others states 69.9 34.3 58.7 35.6 201.0 34.3 173.6 36.8 Total $ 204.6 100.0 % $ 164.6 100.0 % $ 584.2 100.0 % $ 471.1 100.0 % ______________ (1) Includes automobile insurance premiums assumed under quota share agreement with an unaffiliated Texas county mutual insurance company, whereby we assume 100% of the written premium. See Note 6, “Reinsurance,” for additional information regarding gross premiums.

LEASES (Tables)

LEASES (Tables)	9 Months Ended
	Sep. 30, 2021
Leases [Abstract]
Schedule of future lease payments	Future lease payments as of September 30, 2021 were as follows: Operating Leases (dollars in millions) Remainder of 2021 $ 1.0 2022 4.3 2023 4.4 2024 4.3 2025 1.5 2026 and thereafter 3.1 Total future lease payments 18.6 Less: imputed interest (3.9) Total lease liabilities $ 14.7
Schedule of Future Minimum Rental Payments for Operating Leases	As previously disclosed in our 2020 10-K under the prior lease accounting guidance, the following table summarizes, by remaining maturity, future commitments related to operating leases and other arrangements as of December 31, 2020: Operating Leases (dollars in millions) 2021 $ 3.9 2022 4.4 2023 4.4 2024 4.3 2025 1.5 2026 and thereafter 3.1 Total $ 21.6

LONG-TERM DEBT (Tables)

LONG-TERM DEBT (Tables)	9 Months Ended
	Sep. 30, 2021
Debt Disclosure [Abstract]
Schedule of long term debt	The following summarizes the carrying value of long-term debt as of September 30, 2021 and December 31, 2020: September 30, 2021 December 31, 2020 (dollars in millions) Term Loan A $ 98.8 $ 99.5 Term Loan B 100.0 100.0 Total 198.8 199.5 Accrued interest payable 19.3 10.2 Unamortized discount and debt issuance costs (16.4) (21.5) Total $ 201.7 $ 188.2

SHARE-BASED COMPENSATION (Table

SHARE-BASED COMPENSATION (Tables)	9 Months Ended
	Sep. 30, 2021
Share-based Payment Arrangement [Abstract]
Schedule of share-based compensation expense	The following table displays share-based compensation expense recorded in the condensed consolidated statements of operations and comprehensive loss: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Share-based compensation expense: Loss and loss adjustment expenses $ — $ — $ 0.6 $ 0.5 Sales and marketing 0.4 — 0.6 1.0 Other insurance expense 0.4 — 0.9 1.0 Technology and development 2.9 0.2 4.7 5.4 General and administrative 3.8 0.6 7.9 19.1 Total share-based compensation expense $ 7.5 $ 0.8 $ 14.7 $ 27.0 The following table provides total share-based compensation expense by type of award: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Share-based compensation expense: Restricted stock unit expense $ 6.1 $ — $ 10.9 $ — Stock option expense 1.4 0.8 3.8 27.0 Total share-based compensation expense $ 7.5 $ 0.8 $ 14.7 $ 27.0
Summary of RSU activity	A summary of RSU activity for the nine months ended September 30, 2021 is as follows: Nine Months Ended September 30, 2021 Restricted Stock Units Number of Shares Weighted-Average Aggregate Intrinsic Value (in millions, except per share amounts) Nonvested at January 1, 2021 0.4 $ 18.41 $ 6.2 Granted 8.9 10.71 Vested (0.1) 15.77 0.7 Forfeited, expired or canceled (0.8) 11.79 Nonvested at September 30, 2021 8.4 $ 10.93 $ 44.6
Summary of option activity	A summary of option activity for the nine months ended September 30, 2021 is as follows: Nine Months Ended September 30, 2021 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, 2021 10.4 $ 2.39 7.75 $ 137.7 Granted — 10.82 Exercised (2.4) 1.88 23.4 Forfeited, expired or canceled (1.0) 4.71 Outstanding and exercisable at September 30, 2021 7.0 $ 2.28 6.93 $ 23.7

OTHER COMPREHENSIVE INCOME AN_2

OTHER COMPREHENSIVE INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME (Tables)	9 Months Ended
	Sep. 30, 2021
Equity [Abstract]
Schedule of AOCI	The following table presents the changes in our accumulated other comprehensive income, or AOCI, for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Change in net unrealized gains (losses) on investments: Accumulated other comprehensive income beginning balance $ 2.1 $ 5.5 $ 5.6 $ 0.6 Other comprehensive income (loss) before reclassifications (0.5) 0.2 (1.6) 5.2 Net realized gains on investments reclassified from AOCI to net loss — (0.1) (2.4) (0.2) Net current period other comprehensive income (loss) (0.5) 0.1 (4.0) 5.0 Accumulated other comprehensive income ending balance $ 1.6 $ 5.6 $ 1.6 $ 5.6

LOSS PER SHARE (Tables)

LOSS PER SHARE (Tables)	9 Months Ended
	Sep. 30, 2021
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 nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (in millions, except per share amounts) Net loss $ (133.0) $ (85.2) $ (411.2) $ (229.7) Weighted-average common shares outstanding: basic and diluted (both Class A and B) 250.2 38.8 248.8 38.7 Loss per common share: basic and diluted (both Class A and B) $ (0.53) $ (2.20) $ (1.65) $ (5.94)
Schedule of anti-dilutive securities	We excluded the following potential common shares, presented based on amounts outstanding at each period end, from the computation of diluted net loss per share attributable to common shareholders for the periods indicated because including them would have had an anti-dilutive effect: As of September 30, 2021 2020 (in millions) Options to purchase common stock 7.0 11.6 Nonvested shares subject to repurchase 2.3 5.3 Restricted stock units 8.4 0.1 Redeemable convertible preferred stock (as converted to common stock) — 161.8 Warrants to purchase redeemable convertible preferred stock (as converted to common stock) — 0.6 Total 17.7 179.4

GEOGRAPHICAL BREAKDOWN OF GRO_2

GEOGRAPHICAL BREAKDOWN OF GROSS WRITTEN PREMIUM (Tables)	9 Months Ended
	Sep. 30, 2021
Insurance [Abstract]
Schedule of Direct and Assumed Written Premiums	The following table reflects amounts affecting the condensed consolidated balance sheets and statements of operations and comprehensive loss for reinsurance as of and for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 (dollars in millions) Premiums written: Direct $ 197.0 $ 164.6 $ 576.6 $ 471.1 Assumed 7.6 — 7.6 — Ceded (107.5) (189.1) (306.8) (274.7) Net premiums written $ 97.1 $ (24.5) $ 277.4 $ 196.4 Premiums earned: Direct $ 188.5 $ 154.4 $ 529.4 $ 450.2 Assumed 0.9 — 0.9 — Ceded (104.3) (109.5) (304.9) (171.8) Net premiums earned $ 85.1 $ 44.9 $ 225.4 $ 278.4 Losses and LAE incurred: Direct $ 193.7 $ 153.9 $ 504.6 $ 422.9 Assumed 1.9 — 1.9 — Ceded (81.2) (77.8) (222.0) (119.6) Net losses and LAE incurred $ 114.4 $ 76.1 $ 284.5 $ 303.3 Gross written premium, by state is as follows for the three and nine months ended September 30, 2021 and 2020: Three Months Ended September 30, Nine Months Ended September 30, 2021 2020 2021 2020 Amount % of Total Amount % of Total Amount % of Total Amount % of Total State (dollars in millions) Texas (1) $ 40.4 19.7 % $ 35.2 21.4 % $ 120.8 20.7 % $ 100.4 21.3 % Georgia 21.6 10.6 18.8 11.4 61.3 10.5 56.4 12.0 Louisiana 12.3 6.0 8.0 4.9 32.9 5.6 20.6 4.4 Pennsylvania 11.8 5.8 7.9 4.8 31.5 5.4 23.1 4.9 Nevada 9.5 4.6 5.8 3.5 26.0 4.5 13.3 2.8 Colorado 9.3 4.5 5.8 3.5 25.7 4.4 14.3 3.0 Utah 9.1 4.4 6.9 4.2 25.6 4.4 19.1 4.1 South Carolina 8.0 3.9 2.1 1.3 20.6 3.5 6.3 1.3 Arizona 6.4 3.1 7.9 4.8 19.1 3.3 22.9 4.9 Missouri 6.3 3.1 7.5 4.6 19.7 3.4 21.1 4.5 All others states 69.9 34.3 58.7 35.6 201.0 34.3 173.6 36.8 Total $ 204.6 100.0 % $ 164.6 100.0 % $ 584.2 100.0 % $ 471.1 100.0 % ______________ (1) Includes automobile insurance premiums assumed under quota share agreement with an unaffiliated Texas county mutual insurance company, whereby we assume 100% of the written premium. See Note 6, “Reinsurance,” for additional information regarding gross premiums.

NATURE OF BUSINESS (Details)

NATURE OF BUSINESS (Details)	Sep. 30, 2021
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Ownership percentage	100.00%

Accounting Policies (Details)

Accounting Policies (Details) - USD ($) $ in Millions	Jan. 01, 2021	Sep. 30, 2021
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Total lease liabilities		$ 14.7
Operating lease, right of use asset		$ 9
ASU 2016-02
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Total lease liabilities	$ 16.2
Operating lease, right of use asset	9.9
Reclassification of deferred rent and lease liabilities	$ 6.3

INVESTMENTS - Amortized Cost an

INVESTMENTS - Amortized Cost and Fair Value (Details) - USD ($) $ in Millions	Sep. 30, 2021	Dec. 31, 2020
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 129.2	$ 218.4
Gross Unrealized Gains	2	5.7
Gross Unrealized Losses	(0.4)	(0.1)
Fair Value	130.8	224
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	22.9	16.9
Gross Unrealized Gains	0.1	0.1
Gross Unrealized Losses	(0.2)	0
Fair Value	22.8	17
Municipal securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	20	22.6
Gross Unrealized Gains	0.5	0.8
Gross Unrealized Losses	(0.1)	0
Fair Value	20.4	23.4
Corporate debt securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	48.7	87.5
Gross Unrealized Gains	1	3.1
Gross Unrealized Losses	(0.1)	(0.1)
Fair Value	49.6	90.5
Residential mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	4	7.8
Gross Unrealized Gains	0	0
Gross Unrealized Losses	0	0
Fair Value	4	7.8
Commercial mortgage backed securities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	29	57.1
Gross Unrealized Gains	0.4	1.3
Gross Unrealized Losses	0	0
Fair Value	29.4	58.4
Other debt obligations
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	4.6	23.5
Gross Unrealized Gains	0	0.4
Gross Unrealized Losses	0	0
Fair Value	4.6	23.9
Total fixed maturities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost		215.4
Gross Unrealized Gains		5.7
Gross Unrealized Losses		(0.1)
Fair Value	$ 130.8	221
Short-term investments
Debt Securities, Available-for-sale [Line Items]
Amortized Cost		3
Gross Unrealized Gains		0
Gross Unrealized Losses		0
Fair Value		$ 3

INVESTMENTS - Other Investments

INVESTMENTS - Other Investments (Details) - USD ($) $ in Millions	Sep. 30, 2021	Dec. 31, 2020
Investments, Debt and Equity Securities [Abstract]
Other investments	$ 1.3	$ 0.5

INVESTMENTS - Unrealized Losses

INVESTMENTS - Unrealized Losses (Details) - USD ($) $ in Millions	Sep. 30, 2021	Dec. 31, 2020
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	$ 34.9	$ 29.6
Less than 12 Months, Unrealized Loss	(0.3)	(0.1)
12 Months or More, Fair Value	2.3	0
12 Months or More, Unrealized Loss	(0.1)	0
Total, Fair Value	37.2	29.6
Total, Unrealized Loss	(0.4)	(0.1)
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	19.6	15.7
Less than 12 Months, Unrealized Loss	(0.2)	0
12 Months or More, Fair Value	0	0
12 Months or More, Unrealized Loss	0	0
Total, Fair Value	19.6	15.7
Total, Unrealized Loss	(0.2)	0
Municipal securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	5	2.3
Less than 12 Months, Unrealized Loss	(0.1)	0
12 Months or More, Fair Value	0	0
12 Months or More, Unrealized Loss	0	0
Total, Fair Value	5	2.3
Total, Unrealized Loss	(0.1)	0
Corporate debt securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	4.9	2.9
Less than 12 Months, Unrealized Loss	0	(0.1)
12 Months or More, Fair Value	1.6	0
12 Months or More, Unrealized Loss	(0.1)	0
Total, Fair Value	6.5	2.9
Total, Unrealized Loss	(0.1)	(0.1)
Residential mortgage-backed securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	1.7	3.7
Less than 12 Months, Unrealized Loss	0	0
12 Months or More, Fair Value	0.7	0
12 Months or More, Unrealized Loss	0	0
Total, Fair Value	2.4	3.7
Total, Unrealized Loss	0	0
Commercial mortgage backed securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	3.7	4.9
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	3.7	4.9
Total, Unrealized Loss	$ 0	0
Other debt obligations
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value		0.1
Less than 12 Months, Unrealized Loss		0
12 Months or More, Fair Value		0
12 Months or More, Unrealized Loss		0
Total, Fair Value		0.1
Total, Unrealized Loss		$ 0

INVESTMENTS - Gross and Net Rea

INVESTMENTS - Gross and Net Realized Gains and Losses (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Investments, Debt and Equity Securities [Abstract]
Realized gains on investments	$ 0	$ 0.2	$ 2.5	$ 0.3
Realized losses on investments	0	(0.1)	(0.1)	(0.1)
Net realized gains on investments	$ 0	$ 0.1	$ 2.4	$ 0.2

INVESTMENTS - Contractual Matur

INVESTMENTS - Contractual Maturity (Details) - USD ($) $ in Millions	Sep. 30, 2021	Dec. 31, 2020
Amortized Cost
Due in one year or less	$ 18.1
Due after one year through five years	90.1
Due five years through 10 years	5
Due after 10 years	16
Amortized Cost	129.2	$ 218.4
Fair Value
Due in one year or less	17.8
Due after one year through five years	91.8
Due five years through 10 years	5
Due after 10 years	16.2
Total	$ 130.8	$ 224

INVESTMENTS - Net Investment In

INVESTMENTS - Net Investment Income (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Net Investment Income [Line Items]
Total	$ 1.2	$ 1.2	$ 3.1	$ 4.6
Investment expense	(0.2)	(0.1)	(0.5)	(0.3)
Net investment income	1	1.1	2.6	4.3
Interest on bonds
Net Investment Income [Line Items]
Total	0.6	1.1	1.9	3.2
Interest on deposits and cash equivalents
Net Investment Income [Line Items]
Total	0.2	0.1	0.8	1.4
Other investments
Net Investment Income [Line Items]
Total	$ 0.4	$ 0	$ 0.4	$ 0

INVESTMENTS - Credit Ratings (D

INVESTMENTS - Credit Ratings (Details) - USD ($) $ in Millions	9 Months Ended	12 Months Ended
	Sep. 30, 2021	Dec. 31, 2020
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 129.2	$ 218.4
Fair Value	$ 130.8	$ 224
Concentration percentage	100.00%	100.00%
AAA
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 70.2	$ 116.5
Fair Value	$ 70.6	$ 118.7
AAA | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	54.00%	53.00%
AA+, AA, AA-, A-1
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 14.7	$ 22.7
Fair Value	$ 15	$ 23.3
AA+, AA, AA-, A-1 | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	11.50%	10.40%
A+, A, A-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 34.3	$ 57.5
Fair Value	$ 34.9	$ 59.4
A+, A, A- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	26.70%	26.50%
BBB+, BBB, BBB-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 10	$ 21.7
Fair Value	$ 10.3	$ 22.6
BBB+, BBB, BBB- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	7.80%	10.10%

FAIR VALUE OF FINANCIAL INSTR_3

FAIR VALUE OF FINANCIAL INSTRUMENTS - Balance Sheet Grouping (Details) - USD ($) $ in Millions	Sep. 30, 2021	Dec. 31, 2020
Assets
AFS securities	$ 130.8	$ 224
Cash equivalents	208.7	568.4
Total assets at fair value	339.5	792.4
U.S. Treasury securities and agencies
Assets
AFS securities	22.8	17
Municipal securities
Assets
AFS securities	20.4	23.4
Corporate debt securities
Assets
AFS securities	49.6	90.5
Residential mortgage-backed securities
Assets
AFS securities	4	7.8
Commercial mortgage backed securities
Assets
AFS securities	29.4	58.4
Other debt obligations
Assets
AFS securities	4.6	23.9
Total fixed maturities
Assets
AFS securities	130.8	221
Short-term investments
Assets
AFS securities		3
Level 1
Assets
Cash equivalents	208.7	568.4
Total assets at fair value	231.5	587.6
Level 1 | U.S. Treasury securities and agencies
Assets
AFS securities	22.8	17
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	22.8	17
Level 1 | Short-term investments
Assets
AFS securities		2.2
Level 2
Assets
Cash equivalents	0	0
Total assets at fair value	108	204.8
Level 2 | U.S. Treasury securities and agencies
Assets
AFS securities	0	0
Level 2 | Municipal securities
Assets
AFS securities	20.4	23.4
Level 2 | Corporate debt securities
Assets
AFS securities	49.6	90.5
Level 2 | Residential mortgage-backed securities
Assets
AFS securities	4	7.8
Level 2 | Commercial mortgage backed securities
Assets
AFS securities	29.4	58.4
Level 2 | Other debt obligations
Assets
AFS securities	4.6	23.9
Level 2 | Total fixed maturities
Assets
AFS securities	108	204
Level 2 | Short-term investments
Assets
AFS securities		0.8
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

FAIR VALUE OF FINANCIAL INSTR_4

FAIR VALUE OF FINANCIAL INSTRUMENTS - Long Term Debt (Details) - Level 2 - USD ($) $ in Millions	Sep. 30, 2021	Dec. 31, 2020
Carrying amount
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 201.7	$ 188.2
Estimated Fair Value
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 218.3	$ 209

LOSS AND LOSS ADJUSTMENT EXPE_3

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Gross loss and LAE reserves, January 1			$ 237.2	$ 140.7
Reinsurance recoverable on unpaid losses			(79.6)	(18.9)
Net loss and LAE reserves, January 1			157.6	121.8
Net incurred loss and LAE related to:
Current year			293.8	282
Prior years			(9.3)	21.3
Total incurred	$ 114.4	$ 76.1	284.5	303.3
Net paid loss and LAE related to:
Current year			150.4	165.8
Prior years			72.6	100.4
Total paid			223	266.2
Net loss and LAE reserves, September 30	219.1	158.9	219.1	158.9
Plus reinsurance recoverable on unpaid losses	81.6	66.4	81.6	66.4
Gross loss and LAE reserves, September 30	$ 300.7	$ 225.3	$ 300.7	$ 225.3

LOSS AND LOSS ADJUSTMENT EXPE_4

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES- Narrative (Details) - USD ($) $ in Millions	9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020
Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims [Abstract]
Incurred losses and LAE attributable to prior accident years	$ (9.3)	$ 21.3

REINSURANCE (Details)

REINSURANCE (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Premiums written:
Direct	$ 197	$ 164.6	$ 576.6	$ 471.1
Assumed	7.6	0	7.6	0
Ceded	(107.5)	(189.1)	(306.8)	(274.7)
Net premiums written	97.1	(24.5)	277.4	196.4
Premiums earned:
Direct	188.5	154.4	529.4	450.2
Assumed	0.9	0	0.9	0
Ceded	(104.3)	(109.5)	(304.9)	(171.8)
Net premiums earned	85.1	44.9	225.4	278.4
Losses and LAE incurred:
Direct	193.7	153.9	504.6	422.9
Assumed	1.9	0	1.9	0
Ceded	(81.2)	(77.8)	(222)	(119.6)
Total incurred	$ 114.4	$ 76.1	$ 284.5	$ 303.3

LEASES - Narrative (Details)

LEASES - Narrative (Details) $ in Millions	3 Months Ended	9 Months Ended
	Sep. 30, 2021USD ($)	Sep. 30, 2021USD ($)
Lessee, Lease, Description [Line Items]
Operating lease, weighted-average discount rate	10.80%	10.80%
Operating lease, weighted-average remaining lease term	4 years 7 months 6 days	4 years 7 months 6 days
Operating lease liability	$ 14.7	$ 14.7
Operating lease, right of use asset	9	9
Operating lease cost	$ 0.8	2.3
Operating lease cash payments		$ 1.8
Operating Lease, Liability, Statement of Financial Position [Extensible Enumeration]	Other liabilities	Other liabilities
Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]	Other assets	Other assets
Maximum
Lessee, Lease, Description [Line Items]
Operating lease, remaining lease term	6 years	6 years
Minimum
Lessee, Lease, Description [Line Items]
Operating lease, remaining lease term	1 year	1 year

LEASES - Future Lease Payment (

LEASES - Future Lease Payment (Details) $ in Millions	Sep. 30, 2021USD ($)
Leases [Abstract]
Remainder of 2021	$ 1
2022	4.3
2023	4.4
2024	4.3
2025	1.5
2026 and thereafter	3.1
Total future lease payments	18.6
Less: imputed interest	(3.9)
Total lease liabilities	$ 14.7

LEASES - Operating Lease Maturi

LEASES - Operating Lease Maturities (Details) $ in Millions	Dec. 31, 2020USD ($)
Leases [Abstract]
2021	$ 3.9
2022	4.4
2023	4.4
2024	4.3
2025	1.5
2026 and thereafter	3.1
Total	$ 21.6

LONG-TERM DEBT - Narrative (Det

LONG-TERM DEBT - Narrative (Details) - USD ($)	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Debt Instrument [Line Items]
Payment-in-kind interest expense	$ 3,500,000	$ 2,300,000	$ 9,300,000	$ 6,800,000
Secured debt | Term Loan A | LIBOR
Debt Instrument [Line Items]
Variable rate percentage			4.00%
Secured debt | Amended Term Loan B | LIBOR
Debt Instrument [Line Items]
Variable rate percentage			10.50%
Revolving Loan | Line of Credit | Amended Term Loan A
Debt Instrument [Line Items]
Maximum borrowing capacity	100,000,000		$ 100,000,000
Unused fee percentage			0.50%
Letter of Credit | Line of Credit | Amended Term Loan A
Debt Instrument [Line Items]
Average daily amount fee percentage			4.00%
Fronting fee percentage			0.125%
Letters of credit outstanding	$ 0		$ 0

LONG-TERM DEBT - Schedule Of De

LONG-TERM DEBT - Schedule Of Debt (Details) - USD ($) $ in Millions	Sep. 30, 2021	Dec. 31, 2020
Debt Instrument [Line Items]
Long-term Debt, Total	$ 201.7	$ 188.2
Secured debt
Debt Instrument [Line Items]
Long-term Debt, Gross	198.8	199.5
Accrued interest payable	19.3	10.2
Unamortized discount and debt issuance costs		(21.5)
Long-term Debt, Total	201.7	188.2
Secured debt | Term Loan A
Debt Instrument [Line Items]
Long-term Debt, Gross	98.8	99.5
Secured debt | Term Loan B
Debt Instrument [Line Items]
Long-term Debt, Gross	$ 100	$ 100

INCOME TAXES (Details)

INCOME TAXES (Details)	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Income Tax Disclosure [Abstract]
Effective income tax rate	0.00%	0.00%	0.00%	0.00%
Federal income tax rate			21.00%

SHARE-BASED COMPENSATION - Narr

SHARE-BASED COMPENSATION - Narrative (Details) - USD ($) shares in Millions, $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 7.5	$ 0.8	$ 14.7	$ 27
Restricted stock unit expense
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	6.1	0	10.9	0
Unrecognized compensation cost	81.7		$ 81.7
Unrecognized compensation cost, period of recognition			4 years
Stock option expense
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	1.4	$ 0.8	$ 3.8	27
Unrecognized compensation cost	$ 5.7		$ 5.7
Unrecognized compensation cost, period of recognition			5 years
Tender offer | Common stock
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense				$ 25.1
2020 Equity Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares available for issuance (in shares)	22.2		22.2

SHARE-BASED COMPENSATION - Shar

SHARE-BASED COMPENSATION - Share-based Compensation Expense (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 7.5	$ 0.8	$ 14.7	$ 27
RSUs
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	6.1	0	10.9	0
Stock option expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	1.4	0.8	3.8	27
Loss and loss adjustment expenses
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0	0	0.6	0.5
Sales and marketing
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.4	0	0.6	1
Other insurance expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.4	0	0.9	1
Technology and development
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	2.9	0.2	4.7	5.4
General and administrative
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 3.8	$ 0.6	$ 7.9	$ 19.1

SHARE-BASED COMPENSATION - RSU

SHARE-BASED COMPENSATION - RSU Activity (Details) - RSUs $ / shares in Units, shares in Millions, $ in Millions	9 Months Ended
	Sep. 30, 2021USD ($)$ / sharesshares
Number of Shares
Beginning balance (in shares) | shares	0.4
Granted (in shares) | shares	8.9
Vested (in shares) | shares	(0.1)
Forfeited, expired or canceled (in shares) | shares	(0.8)
Weighted-Average Grant Date Fair Value per Share
Beginning balance, weighted-average grant date fair value (in dollars per shares)	$ 18.41
Granted, weighted-average grant date fair value (in dollars per shares)	10.71
Vested, weighted-average grant date fair value (in dollars per shares)	15.77
Forfeited, expired or canceled, weighted-average grant date fair value (in dollars per share)	11.79
Ending balance, weighted-average grant date fair value (in dollars per shares)	$ 10.93
Aggregate Intrinsic Value
Beginning balance | $	$ 6.2
Vested | $	0.7
Ending balance | $	$ 44.6

SHARE-BASED COMPENSATION - Opti

SHARE-BASED COMPENSATION - Option Activity (Details) $ / shares in Units, shares in Millions, $ in Millions	9 Months Ended	12 Months Ended
	Sep. 30, 2021USD ($)$ / sharesshares	Dec. 31, 2020USD ($)$ / sharesshares
Number of Shares
Outstanding, beginning balance (in shares) | shares	10.4
Granted (in shares) | shares	0
Common stock—option exercises and restricted stock units vesting, net of shares withheld for employee taxes (in shares) | shares	(2.4)
Forfeited, expired or canceled (in shares) | shares	(1)
Outstanding, ending balance (in shares) | shares	7	10.4
Weighted-Average Exercise Price
Outstanding, beginning balance, weighted-average exercise price (in dollars per share) | $ / shares	$ 2.39
Granted, weighted-average exercise price (in dollars per share) | $ / shares	10.82
Exercised, weighted-average exercise price (in dollars per share) | $ / shares	1.88
Forfeited, expired and canceled, weighted-average exercise price (in dollars per share) | $ / shares	4,710,000
Outstanding, ending balance, weighted-average exercise price (in dollars per share) | $ / shares	$ 2.28	$ 2.39
Outstanding, weighted-average remaining contractual term (in years)	6 years 11 months 4 days	7 years 9 months
Exercisable, weighted-average remaining contractual term (in years)	6 years 11 months 4 days	7 years 9 months
Outstanding, aggregate intrinsic value | $	$ 23.7	$ 137.7
Exercised, aggregate intrinsic value | $	23.4
Exercisable, aggregate intrinsic value | $	$ 23.7	$ 137.7

OTHER COMPREHENSIVE INCOME AN_3

OTHER COMPREHENSIVE INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	$ 762	$ (487.2)	$ 1,032.4	$ (374)
Net current period other comprehensive income (loss)	(0.5)	0.1	(4)	5
Ending balance	636	(570.4)	636	(570.4)
Change in net unrealized gains (losses) on investments:
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	2.1	5.5	5.6	0.6
Other comprehensive income (loss) before reclassifications	(0.5)	0.2	(1.6)	5.2
Net realized gains on investments reclassified from AOCI to net loss	0	(0.1)	(2.4)	(0.2)
Net current period other comprehensive income (loss)	(0.5)	0.1	(4)	5
Ending balance	$ 1.6	$ 5.6	$ 1.6	$ 5.6

LOSS PER SHARE (Details)

LOSS PER SHARE (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020
Earnings Per Share [Abstract]
Net loss	$ (133)	$ (85.2)	$ (411.2)	$ (229.7)
Weighted-average common shares outstanding: basic (both Class A and B) (in shares)	250.2	38.8	248.8	38.7
Weighted-average common shares outstanding: diluted (both Class A and B) (in shares)	250.2	38.8	248.8	38.7
Loss per common share: basic (both Class A and B) (in dollars per share)	$ (0.53)	$ (2.20)	$ (1.65)	$ (5.94)
Loss per common share: diluted (both Class A and B) (in dollars per share)	$ (0.53)	$ (2.20)	$ (1.65)	$ (5.94)

LOSS PER SHARE - Schedule of An

LOSS PER SHARE - Schedule of Anti-Dilutive Securities (Details) - shares shares in Millions	9 Months Ended
	Sep. 30, 2021	Sep. 30, 2020
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	17.7	179.4
Options to purchase common stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	7	11.6
Nonvested shares subject to repurchase
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	2.3	5.3
Restricted stock units
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities (in shares)	8.4	0.1
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	161.8
Warrants to purchase 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	0.6

GEOGRAPHICAL BREAKDOWN OF GRO_3

GEOGRAPHICAL BREAKDOWN OF GROSS WRITTEN PREMIUM (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended		12 Months Ended
	Sep. 30, 2021	Sep. 30, 2020	Sep. 30, 2021	Sep. 30, 2020	Dec. 31, 2020
Effects of Reinsurance [Line Items]
Total	$ 204.6	$ 164.6	$ 584.2	$ 471.1
Concentration percentage			100.00%		100.00%
Texas
Effects of Reinsurance [Line Items]
Total	40.4	35.2	$ 120.8	100.4
Georgia
Effects of Reinsurance [Line Items]
Total	21.6	18.8	61.3	56.4
Louisiana
Effects of Reinsurance [Line Items]
Total	12.3	8	32.9	20.6
Pennsylvania
Effects of Reinsurance [Line Items]
Total	11.8	7.9	31.5	23.1
Nevada
Effects of Reinsurance [Line Items]
Total	9.5	5.8	26	13.3
Colorado
Effects of Reinsurance [Line Items]
Total	9.3	5.8	25.7	14.3
Utah
Effects of Reinsurance [Line Items]
Total	9.1	6.9	25.6	19.1
South Carolina
Effects of Reinsurance [Line Items]
Total	8	2.1	20.6	6.3
Arizona
Effects of Reinsurance [Line Items]
Total	6.4	7.9	19.1	22.9
Missouri
Effects of Reinsurance [Line Items]
Total	6.3	7.5	19.7	21.1
All others states
Effects of Reinsurance [Line Items]
Total	$ 69.9	$ 58.7	$ 201	$ 173.6
Geographic Concentration Risk | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	100.00%	100.00%	100.00%	100.00%
Geographic Concentration Risk | Texas | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	19.70%	21.40%	20.70%	21.30%
Geographic Concentration Risk | Georgia | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	10.60%	11.40%	10.50%	12.00%
Geographic Concentration Risk | Louisiana | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	6.00%	4.90%	5.60%	4.40%
Geographic Concentration Risk | Pennsylvania | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	5.80%	4.80%	5.40%	4.90%
Geographic Concentration Risk | Nevada | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.60%	3.50%	4.50%	2.80%
Geographic Concentration Risk | Colorado | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.50%	3.50%	4.40%	3.00%
Geographic Concentration Risk | Utah | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.40%	4.20%	4.40%	4.10%
Geographic Concentration Risk | South Carolina | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	3.90%	1.30%	3.50%	1.30%
Geographic Concentration Risk | Arizona | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	3.10%	4.80%	3.30%	4.90%
Geographic Concentration Risk | Missouri | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	3.10%	4.60%	3.40%	4.50%
Geographic Concentration Risk | All others states | Gross Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	34.30%	35.60%	34.30%	36.80%

SUBSEQUENT EVENTS (Details)

SUBSEQUENT EVENTS (Details)	Nov. 08, 2021USD ($)	Oct. 15, 2021USD ($)	Oct. 01, 2021USD ($)tranche$ / sharesshares	Dec. 31, 2021	Sep. 30, 2021USD ($)shares	Dec. 31, 2020USD ($)shares
Subsequent Event [Line Items]
Preferred stock, shares issued (in shares) | shares					0	0
Ownership percentage					100.00%
Secured debt
Subsequent Event [Line Items]
Unamortized discount and debt issuance costs						$ (21,500,000)
Revolving Loan | Amended Term Loan B | Line of Credit
Subsequent Event [Line Items]
Unamortized discount and debt issuance costs					$ (16,400,000)
Subsequent event
Subsequent Event [Line Items]
Number of tranches | tranche			8
Debt issuance costs			$ 20,000,000
Subsequent event | Revolving Loan | Amended Term Loan A | Line of Credit
Subsequent Event [Line Items]
Repayments of debt		$ 98,800,000
Payment of interest and fees		$ 200,000
Subsequent event | Revolving Loan | Amended Term Loan B | Line of Credit
Subsequent Event [Line Items]
Repayments of debt	$ 100,000,000
Payment of interest and fees	$ 20,900,000
Subsequent event | Short-Term Warrants
Subsequent Event [Line Items]
Number of tranches | tranche			3
Expiration period			3 years	18 months
Debt issuance costs			$ 9,000,000
Subsequent event | Short-Term Warrants | Minimum
Subsequent Event [Line Items]
Exercise price of warrants (in dollars per share) | $ / shares			$ 10
Subsequent event | Short-Term Warrants | Maximum
Subsequent Event [Line Items]
Exercise price of warrants (in dollars per share) | $ / shares			$ 12
Subsequent event | Long-Term Warrants
Subsequent Event [Line Items]
Number of tranches | tranche			5
Expiration period			5 years
Subsequent event | Long-Term Warrants | Minimum
Subsequent Event [Line Items]
Exercise price of warrants (in dollars per share) | $ / shares			$ 10
Subsequent event | Long-Term Warrants | Maximum
Subsequent Event [Line Items]
Exercise price of warrants (in dollars per share) | $ / shares			$ 30
Subsequent event | Carvana | Root, Inc
Subsequent Event [Line Items]
Ownership percentage			29.90%
Subsequent event | Carvana
Subsequent Event [Line Items]
Number of tranches | tranche			8
Commercial agreement term			5 years
Preferred stock, shares issued (in shares) | shares			14,000,000
Conversion price (in dollars per share) | $ / shares			$ 9
Class A Shares
Subsequent Event [Line Items]
Carry value					$ 0	$ 0
Class A Shares | Subsequent event
Subsequent Event [Line Items]
Carry value			$ 129,000,000
Class A Shares | Subsequent event | Carvana
Subsequent Event [Line Items]
Shares issuable in conversion (in shares) | shares			14,000,000
Series A Preferred Stock | Subsequent event | Carvana
Subsequent Event [Line Items]
Proceeds from issuance of convertible preferred stock			$ 126,000,000