Root (ROOT) 10-Q 6 May 21 2021 Q1 Quarterly report Financial data

COVER PAGE

COVER PAGE - shares	3 Months Ended
	Mar. 31, 2021	Apr. 28, 2021
Entity Listings [Line Items]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Mar. 31, 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
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
Title of 12(b) Security	Class A common stock,$0.0001 par value per share
Trading Symbol	ROOT
Security Exchange Name	NASDAQ
Entity Shell Company	false
Amendment Flag	false
Document Fiscal Year Focus	2021
Document Fiscal Period Focus	Q1
Entity Central Index Key	0001788882
Current Fiscal Year End Date	--12-31
Class A Common Stock
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		86,893,126
Class B Common Stock
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		166,034,886

CONDENSED CONSOLIDATED BALANCE

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED - USD ($) $ in Millions	Mar. 31, 2021	Dec. 31, 2020
Investments:
Fixed maturities available-for sale, at fair value (amortized cost: $134.2 and $215.4 at March 31, 2021 and December 31, 2020, respectively)	$ 136.3	$ 221
Short-term investments (amortized cost: $3.0 and $3.0 at March 31, 2021 and December 31, 2020, respectively)	3	3
Other investments	0.5	0.5
Total investments	139.8	224.5
Cash and cash equivalents	1,106.3	1,112.8
Restricted cash	1	1
Premiums receivable, net of allowance of $2.0 and $3.5 at March 31, 2021 and December 31, 2020, respectively	161	130.1
Reinsurance recoverable	130	124.8
Prepaid reinsurance premiums	101.3	112.8
Other assets	64.8	56.3
Total assets	1,704.2	1,762.3
Liabilities:
Loss and loss adjustment expense reserves	240.7	237.2
Unearned premiums	199.4	157.1
Long-term debt	192.2	188.2
Reinsurance premiums payable	65.7	89.1
Accounts payable and accrued expenses	50.5	48
Other liabilities	21.4	10.3
Total liabilities	769.9	729.9
Commitments and Contingencies (Note 10)
Stockholders’ equity:
Preferred stock, $0.0001 par value, 100.0 shares authorized, zero shares issued and outstanding at March 31, 2021 and December 31, 2020, respectively	0	0
Treasury stock, at cost	(0.8)	(0.8)
Additional paid-in capital	1,780.6	1,775.6
Accumulated other comprehensive income	2.1	5.6
Accumulated loss	(847.6)	(748)
Total stockholders’ equity	934.3	1,032.4
Total liabilities and stockholders’ equity	1,704.2	1,762.3
Class A Common Stock
Stockholders’ equity:
Common stock	0	0
Class B Common Stock
Stockholders’ equity:
Common stock	$ 0	$ 0

CONDENSED CONSOLIDATED BALANC_2

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED (Parenthetical) - USD ($) $ in Millions	Mar. 31, 2021	Dec. 31, 2020
Amortized cost, fixed maturities	$ 134.2	$ 215.4
Amortized cost, short term investments	3	3
Allowance for premiums receivable	$ 2	$ 3.5
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 Common Stock
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)	86,500,000	59,400,000
Common stock, shares outstanding (in shares)	86,500,000	59,400,000
Class B Common Stock
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)	166,400,000	192,200,000
Common stock, shares outstanding (in shares)	166,400,000	192,200,000

CONDENSED CONSOLIDATED STATEMEN

CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS - UNAUDITED - USD ($) shares in Millions, $ in Millions	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Revenue:
Net premiums earned	$ 59.1	$ 117.8
Net investment income	0.9	1.9
Net realized gains on investments	2.4	0
Fee and other income	6.2	4.3
Total revenue	68.6	124
Operating expenses:
Loss and loss adjustment expenses	59.9	129.9
Sales and marketing	68.4	35.8
Other insurance expense	2.4	11.3
Technology and development	13.8	16
General and administrative	18.4	30.9
Total operating expenses	162.9	223.9
Operating loss	(94.3)	(99.9)
Interest expense	(5.3)	(5.7)
Loss before income tax expense	(99.6)	(105.6)
Income tax expense	0	0
Net loss	(99.6)	(105.6)
Other comprehensive loss:
Changes in net unrealized losses on investments	(3.5)	(1.8)
Comprehensive loss	$ (103.1)	$ (107.4)
Loss per common share: basic and diluted (in dollars per share)	$ (0.40)	$ (2.69)
Weighted-average common shares outstanding: basic and diluted (in shares)	247.1	39.3

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 Common Stock	Class A and Class B Common StockClass B Common Stock	Treasury Stock	Additional Paid-in Capital	Accumulated Other Comprehensive Income (Loss)	Accumulated Loss
Beginning Balance at Dec. 31, 2019	$ 560.4
Beginning balance (in shares) at Dec. 31, 2019	158.9
Increase (Decrease) in Temporary Equity [Roll Forward]
Tender offer and subsequent conversion (Note 9) (in shares)	2.9
Ending balance (in shares) at Mar. 31, 2020	161.8
Ending Balance at Mar. 31, 2020	$ 560.4
Beginning balance at Dec. 31, 2019	(374)	$ 0			$ (0.1)	$ 10.5	$ 0.6	$ (385)
Beginning balance (in shares) at Dec. 31, 2019			0	44.4
Treasury stock, beginning balance (in shares) at Dec. 31, 2019					4.5
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(105.6)							(105.6)
Changes in other comprehensive income	(1.8)						(1.8)
Tender offer and subsequent conversion (Note 9) (in shares)				(2.9)
Tender offer and subsequent conversion	25.1					25.1
Common stock—option exercises (in shares)				0.4
Common stock—option exercises	0.3					0.3
Common stock—shared-based compensation expense	0.6					0.6
Treasury stock, ending balance (in shares) at Mar. 31, 2020					4.5
Ending balance (in shares) at Mar. 31, 2020			0	41.9
Ending balance at Mar. 31, 2020	(455.4)	0			$ (0.1)	36.5	(1.2)	(490.6)
Beginning Balance at Dec. 31, 2020	$ 0
Beginning balance (in shares) at Dec. 31, 2020	0
Ending balance (in shares) at Mar. 31, 2021	0
Ending Balance at Mar. 31, 2021	$ 0
Beginning balance at Dec. 31, 2020	1,032.4	0			$ (0.8)	1,775.6	5.6	(748)
Beginning balance (in shares) at Dec. 31, 2020			59.4	192.2
Treasury stock, beginning balance (in shares) at Dec. 31, 2020					4.6
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(99.6)							(99.6)
Changes in other comprehensive income	(3.5)						(3.5)
Conversion of Class B to Class A (in shares)	$ 0		$ 26.1	$ (26.1)
Common stock—option exercises (in shares)	1.2		1	0.3
Common stock—option exercises	$ 2.3					2.3
Reclassification of early-exercised stock option to liabilities	0.4					0.4
Common stock—shared-based compensation expense	2.3					2.3
Treasury stock, ending balance (in shares) at Mar. 31, 2021					4.6
Ending balance (in shares) at Mar. 31, 2021			86.5	166.4
Ending balance at Mar. 31, 2021	$ 934.3	$ 0			$ (0.8)	$ 1,780.6	$ 2.1	$ (847.6)

CONDENSED CONSOLIDATED STATEM_3

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - UNAUDITED - USD ($) $ in Millions	3 Months Ended		12 Months Ended
	Mar. 31, 2021	Mar. 31, 2020	Dec. 31, 2020
Cash flows from operating activities:
Net loss	$ (99.6)	$ (105.6)
Adjustments to reconcile net loss to net cash used in operating activities:
Share-based compensation	2.3	0.6
Tender offer	0	25.1
Depreciation and amortization	3.5	3.7
Bad debt expense	4.7	3.8
Payment-in-kind interest expense	2.4	2.2	$ 2.2
Realized gains on investments	(2.4)	0
Changes in operating assets and liabilities:
Premiums receivable	(35.6)	(19.7)
Reinsurance recoverable	(5.2)	(12)
Prepaid reinsurance premiums	11.5	(21.6)
Other assets	2	(4.2)
Losses and loss adjustment expenses reserves	3.5	34.9
Unearned premiums	42.3	20.3
Reinsurance premiums payable	(23.4)	31.8
Accounts payable and accrued expenses	2.5	(5.4)
Other liabilities	0.6	(0.1)
Net cash used in operating activities	(90.9)	(46.2)
Cash flows from investing activities:
Purchases of investments	0	(100.8)
Proceeds from maturities, call and pay downs of investments	13.1	8.2
Sales of investments	70.2	0
Capitalization of internally developed software	(1.6)	(1.4)
Purchases of fixed assets	(0.4)	(1.3)
Net cash provided by (used in) investing activities	81.3	(95.3)
Cash flows from financing activities:
Proceeds from exercise of stock options and restricted stock units, net of tax proceeds/(withholding)	3.3	0.3
Debt issuance costs	0	(0.1)
Repayments of long-term debt	(0.2)	(12.7)
Net cash provided by (used in) financing activities	3.1	(12.5)
Net decrease in cash, cash equivalents and restricted cash	(6.5)	(154)
Cash, cash equivalents and restricted cash at beginning of period	1,113.8	416.6	416.6
Cash, cash equivalents and restricted cash at end of period	$ 1,107.3	$ 262.6	$ 1,113.8

NATURE OF BUSINESS

NATURE OF BUSINESS	3 Months Ended
	Mar. 31, 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, and Root Property & Casualty, a Delaware-domiciled insurance 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 direct-to-consumer model with more than 75% of our personal insurance customers acquired through mobile applications. We offer auto and renters insurance products underwritten by Root Insurance Company.

BASIS OF PRESENTATION AND SUMMA

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES	3 Months Ended
	Mar. 31, 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 notes included in the Annual Report on Form 10-K filed with the SEC on March 4, 2021. 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 premium 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 to develop, 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. Recently Adopted Financial Accounting Standards —In February 2016, the FASB issued Accounting Standards Update No. 2016-02, Leases (Topic 842) . 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 6, “Leases.” Upcoming Accounting Pronouncements— We currently qualify as an "emerging growth company" 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. In June 2016, the FASB issued ASU 2016-13, Financial Instruments—Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments . ASU 2016-13 amends previous guidance on the impairment of financial instruments by adding an impairment model that allows an entity to recognize expected credit losses as an allowance rather than impairing as they are incurred. The new guidance is intended to reduce complexity of credit impairment models and result in a more timely recognition of expected credit losses. The effective date of ASU 2016-13 is for reporting periods beginning after December 15, 2022. We are currently evaluating the impact of ASU 2016-13.

INVESTMENTS

INVESTMENTS	3 Months Ended
	Mar. 31, 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 March 31, 2021 and December 31, 2020 are as follows: March 31, 2021 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 16.0 $ 0.1 $ (0.1) $ 16.0 Municipal securities 20.0 0.5 — 20.5 Corporate debt securities 50.6 1.2 (0.1) 51.7 Residential mortgage-backed securities 6.2 — (0.1) 6.1 Commercial mortgage backed securities 31.4 0.5 — 31.9 Other debt obligations 10.0 0.1 — 10.1 Total fixed maturities 134.2 2.4 (0.3) 136.3 Short-term investments 3.0 — — 3.0 Total $ 137.2 $ 2.4 $ (0.3) $ 139.3 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 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 March 31, 2021 and December 31, 2020: March 31, 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 $ 14.0 $ (0.1) $ — $ — $ 14.0 $ (0.1) Municipal securities 6.4 — — — 6.4 — Corporate debt securities 8.1 (0.1) — — 8.1 (0.1) Residential mortgage-backed securities 4.3 (0.1) 0.3 — 4.6 (0.1) Commercial mortgage-backed securities 3.1 — — — 3.1 — Total bonds $ 35.9 $ (0.3) $ 0.3 $ — $ 36.2 $ (0.3) 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 in the three months ended March 31, 2021 or 2020, respectively. 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 months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 (dollars in millions) Realized gains on investments $ 2.5 $ — Realized losses on investments (0.1) — Net realized gains on investments $ 2.4 $ — The following table sets forth the amortized cost and fair value of short-term investments and fixed maturity securities by contractual maturity at March 31, 2021: March 31, 2021 Amortized Cost Fair Value (dollars in millions) Due in one year or less $ 9.4 $ 9.4 Due after one year through five years 98.8 100.6 Due five years through 10 years 9.7 9.8 Due after 10 years 19.3 19.5 Total $ 137.2 $ 139.3 The following table sets forth the components of net investment income for the three months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 (dollars in millions) Interest on bonds $ 0.8 $ 0.9 Interest on deposits and cash equivalents 0.3 1.1 Total 1.1 2.0 Investment expense (0.2) (0.1) Net investment income $ 0.9 $ 1.9 The following tables summarize the credit ratings of investments at March 31, 2021 and December 31, 2020: March 31, 2021 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 73.2 $ 74.0 53.1 % AA+, AA, AA-, A-1 17.0 17.3 12.5 A+, A, A- 36.4 37.1 26.6 BBB+, BBB, BBB- 10.6 10.9 7.8 Total $ 137.2 $ 139.3 100.0 % 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	3 Months Ended
	Mar. 31, 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 March 31, 2021 and December 31, 2020: March 31, 2021 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 16.0 $ — $ — $ 16.0 Municipal securities — 20.5 — 20.5 Corporate debt securities — 51.7 — 51.7 Residential mortgage-backed securities — 6.1 — 6.1 Commercial mortgage-backed securities — 31.9 — 31.9 Other debt obligations — 10.1 — 10.1 Total fixed maturities 16.0 120.3 — 136.3 Short-term investments 2.2 0.8 — 3.0 Cash equivalents 485.7 — — 485.7 Total assets at fair value $ 503.9 $ 121.1 $ — $ 625.0 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 March 31, 2021 and December 31, 2020 the carrying amounts and fair values of these financial instruments were as follows: Carrying Amount as of March 31, 2021 Estimated Fair Value as of March 31, 2021 Carrying Amount as of December 31, 2020 Estimated Fair Value as of December 31, 2020 (dollars in millions) Long-term debt $ 192.2 $ 211.5 $ 188.2 $ 209.0

LOSS AND LOSS ADJUSTMENT EXPENS

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES	3 Months Ended
	Mar. 31, 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: Three Months Ended March 31, 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 69.8 122.0 Prior years (9.9) 7.9 Total incurred 59.9 129.9 Net paid loss and LAE related to: Current year 25.3 44.1 Prior years 35.3 54.2 Total paid 60.6 98.3 Net loss and LAE reserves, March 31 156.9 153.4 Plus reinsurance recoverable on unpaid losses 83.8 22.2 Gross loss and LAE reserves, March 31 $ 240.7 $ 175.6 Incurred losses and LAE attributable to prior accident years was a decrease of $9.9 million and an increase of $7.9 million for the three months ended March 31, 2021 and 2020, respectively. For the three months ended March 31, 2021, the development of incurred losses related to prior periods was primarily related to lower-than-expected reported losses on bodily injury and uninsured motorist bodily injury claims and greater than expected recoveries from subrogation and salvage from 2020. For the three months ended March 31, 2020, the development of incurred losses and related to prior periods was primarily related to higher-than-expected reported losses on bodily injury and collision coverages from 2019.

LEASES

LEASES	3 Months Ended
	Mar. 31, 2021
Leases [Abstract]
LEASES	LEASESWe 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 March 31, 2021, our leases had a weighted-average discount rate of 10.8%. Our leases have remaining lease terms from less than 1 year up to approximately 7 years with a weighted-average remaining lease term of 5.1 years as of March 31, 2021. As of March 31, 2021, we recognized an operating lease liability of $15.8 million and corresponding right-of-use asset of $9.7 million. Operating lease liabilities are included in other liabilities and operating lease right-of-use assets are included in other assets in our condensed consolidated balance sheets. For the three months ended March 31, 2021, we recognized operating lease costs of $0.8 million. Variable lease expense and short-term lease expense recognized during the three months ended March 31, 2021 were not material. Moreover, we recognized operating cash flows paid for amounts included in the measurement of operating lease liabilities of $0.9 million. We may also sublease portions of our offices, 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 months ended March 31, 2021. Future lease payments as of March 31, 2021 were as follows: Operating Leases (dollars in millions) Remainder of 2021 $ 2.9 2022 4.3 2023 4.4 2024 4.3 2025 1.5 2026 and thereafter 3.1 Total future lease payments 20.5 Less: imputed interest (4.7) Total lease liabilities $ 15.8 As previously disclosed in our 2020 Annual Report on Form 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	3 Months Ended
	Mar. 31, 2021
Debt Disclosure [Abstract]
LONG-TERM DEBT	LONG-TERM DEBT Term Loan A is a term loan we have outstanding with a group of syndicated financial institutions which matures on October 15, 2021. Interest is paid monthly and is determined on a floating interest rate calculated on the 1-month LIBOR plus an applicable margin of 4%. As a part of the amended Term Loan A, the syndicate committed, pro rata, to a new $100 million revolving loan. Commitment fees accrue at 0.50% per annum on the daily amount of unused revolver and is paid quarterly. For any amounts drawn on the revolving loan, interest accrues and is paid consistent with Term Loan A. In addition, there is 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 have no letters of credit outstanding or amounts drawn against the revolving loan as of March 31, 2021. Term Loan B is a note we issued to a private equity investor that matures on November 25, 2024. Interest is determined on a floating interest rate calculated on the 3-month LIBOR plus an applicable margin of 10.5%. We currently pay interest pursuant to the terms of the loan agreements and have the option to pay-in-kind, or PIK, on Term Loan B until October 15, 2021. PIK interest is added to the principal balance every 3 months until we no longer PIK interest, at which point interest is paid quarterly. We have elected to PIK interest on Term Loan B from the original date of closing through March 31, 2021. Deferred PIK interest was $2.4 million and $2.2 million for the three months ended March 31, 2021 and 2020, respectively. Deferred PIK interest is recognized as interest expense on the condensed consolidated statements of operations and comprehensive loss. The following summarizes the carrying value of long-term debt as of March 31, 2021 and December 31, 2020: March 31, 2021 December 31, 2020 (dollars in millions) Term Loan A $ 99.3 $ 99.5 Term Loan B 100.0 100.0 Total 199.3 199.5 Accrued interest payable 12.7 10.2 Unamortized discount and debt issuance costs (19.8) (21.5) Total $ 192.2 $ 188.2

INCOME TAXES

INCOME TAXES	3 Months Ended
	Mar. 31, 2021
Income Tax Disclosure [Abstract]
INCOME TAXES	INCOME TAXES The consolidated effective tax rate was 0.0% for both of the three months ended March 31, 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 March 31, 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	3 Months Ended
	Mar. 31, 2021
Share-based Payment Arrangement [Abstract]
SHARE-BASED COMPENSATION	SHARE-BASED COMPENSATIONWe 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 March 31, 2021, we had 30.0 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 March 31, 2021 2020 (dollars in millions) Share-based compensation expense: Loss and loss adjustment expenses $ 0.1 $ 0.4 Sales and marketing — 1.0 Other insurance expense 0.1 0.9 Technology and development 0.3 5.2 General and administrative 1.8 18.2 Total share-based compensation expense $ 2.3 $ 25.7 The following table provides total share-based compensation expense by type of award: Three Months Ended March 31, 2021 2020 (dollars in millions) Share-based compensation expense: Restricted stock unit expense $ 0.6 $ — Stock option expense 1.7 25.7 Total share-based compensation expense $ 2.3 $ 25.7 In March 2020, a current investor completed a tender offer for common stock from vested 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 three months ended March 31, 2020. As of March 31, 2021, there was $7.6 million and $8.6 million of unrecognized compensation cost related to unvested stocks options and restricted stock units, respectively. The remaining costs are expected to be recognized over a period of six Restricted Stock Units A summary of RSU activity for the three months ended March 31, 2021 is as follows: March 31, 2021 Restricted Stock Units Number of Shares Weighted-Average Aggregate Intrinsic Value (in millions, except exercise price and term amounts) Nonvested at January 1, 2021 0.4 $ 18.41 $ 6.2 Granted 0.1 16.02 Vested — 17.27 0.3 Forfeited, expired or canceled — 21.49 Nonvested at March 31, 2021 0.5 $ 17.75 $ 6.7 Stock Options A summary of option activity for the three months ended March 31, 2021 is as follows: March 31, 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 — — Exercised (1.2) 2.00 12.1 Forfeited, expired or canceled (0.7) 4.80 Outstanding and exercisable at March 31, 2021 8.5 $ 2.24 7.17 $ 88.5

COMMITMENTS AND CONTINGENCIES

COMMITMENTS AND CONTINGENCIES	3 Months Ended
	Mar. 31, 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, in connection with and following the Company’s IPO. 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. On March 25, 2021, a purported class action complaint was filed against the Company, certain of its current officers and directors, Goldman Sachs & Co. LLC, Morgan Stanley & Co. LLC, Barclays Capital Inc. and Wells Fargo Securities, LLC, in the U.S. District Court for the Southern District of Ohio (Case No. 2:21-cv-01301) 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 11 and 15 of the Securities Act, in connection with the Company’s IPO. 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	3 Months Ended
	Mar. 31, 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 (loss), or AOCI, for the three months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 (dollars in millions) Change in net unrealized losses on investments: Accumulated other comprehensive income beginning balance $ 5.6 $ 0.6 Other comprehensive loss before reclassifications (1.1) (1.8) Net realized gains on investments reclassified from AOCI to net loss (2.4) — Net current period other comprehensive loss (3.5) (1.8) Accumulated other comprehensive income (loss) ending balance $ 2.1 $ (1.2)

LOSS PER SHARE

LOSS PER SHARE	3 Months Ended
	Mar. 31, 2021
Earnings Per Share [Abstract]
Loss Per Share	LOSS PER SHARE The following table displays the computation of basic and diluted loss per share of common stock for the three months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 (in millions, except per share amounts) Net loss $ (99.6) $ (105.6) Weighted-average common shares outstanding: basic and diluted 247.1 39.3 Loss per common share: basic and diluted $ (0.40) $ (2.69) 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 March 31, 2021 2020 (in millions) Options to purchase common stock 8.5 12.4 Nonvested shares subject to repurchase 4.6 6.6 Restricted stock units 0.5 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 13.6 181.5

GEOGRAPHICAL BREAKDOWN OF DIREC

GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM	3 Months Ended
	Mar. 31, 2021
Insurance [Abstract]
GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM	GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM Direct written premium, or DWP, by state is as follows for the three months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 Amount % of DWP Amount % of DWP State (dollars in millions) Texas $ 43.0 21.2 % $ 34.3 20.9 % Georgia 19.0 9.4 18.2 11.1 Pennsylvania 10.4 5.1 8.5 5.2 Louisiana 10.3 5.1 6.8 4.1 Colorado 8.9 4.4 4.0 2.4 Utah 8.6 4.2 6.0 3.7 Nevada 8.3 4.1 3.4 2.1 Missouri 7.9 3.9 7.5 4.6 Kentucky 7.5 3.7 11.5 7.0 Arizona 7.3 3.6 8.5 5.2 All others states 71.3 35.3 55.5 33.7 Total $ 202.5 100.0 % $ 164.2 100.0 %

BASIS OF PRESENTATION AND SUM_2

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Policies)	3 Months Ended
	Mar. 31, 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 notes included in the Annual Report on Form 10-K filed with the SEC on March 4, 2021.
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.
Recently Adopted Financial Accounting Standards/Upcoming Accounting Pronouncements	Recently Adopted Financial Accounting Standards —In February 2016, the FASB issued Accounting Standards Update No. 2016-02, Leases (Topic 842) . 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 6, “Leases.” Upcoming Accounting Pronouncements— We currently qualify as an "emerging growth company" 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. In June 2016, the FASB issued ASU 2016-13, Financial Instruments—Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments . ASU 2016-13 amends previous guidance on the impairment of financial instruments by adding an impairment model that allows an entity to recognize expected credit losses as an allowance rather than impairing as they are incurred. The new guidance is intended to reduce complexity of credit impairment models and result in a more timely recognition of expected credit losses. The effective date of ASU 2016-13 is for reporting periods beginning after December 15, 2022. We are currently evaluating the impact of ASU 2016-13.

INVESTMENTS (Tables)

INVESTMENTS (Tables)	3 Months Ended
	Mar. 31, 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 March 31, 2021 and December 31, 2020 are as follows: March 31, 2021 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Fixed maturities: U.S. Treasury securities and agencies $ 16.0 $ 0.1 $ (0.1) $ 16.0 Municipal securities 20.0 0.5 — 20.5 Corporate debt securities 50.6 1.2 (0.1) 51.7 Residential mortgage-backed securities 6.2 — (0.1) 6.1 Commercial mortgage backed securities 31.4 0.5 — 31.9 Other debt obligations 10.0 0.1 — 10.1 Total fixed maturities 134.2 2.4 (0.3) 136.3 Short-term investments 3.0 — — 3.0 Total $ 137.2 $ 2.4 $ (0.3) $ 139.3 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 months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 (dollars in millions) Realized gains on investments $ 2.5 $ — Realized losses on investments (0.1) — Net realized gains on investments $ 2.4 $ — The following table sets forth the amortized cost and fair value of short-term investments and fixed maturity securities by contractual maturity at March 31, 2021: March 31, 2021 Amortized Cost Fair Value (dollars in millions) Due in one year or less $ 9.4 $ 9.4 Due after one year through five years 98.8 100.6 Due five years through 10 years 9.7 9.8 Due after 10 years 19.3 19.5 Total $ 137.2 $ 139.3
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 March 31, 2021 and December 31, 2020: March 31, 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 $ 14.0 $ (0.1) $ — $ — $ 14.0 $ (0.1) Municipal securities 6.4 — — — 6.4 — Corporate debt securities 8.1 (0.1) — — 8.1 (0.1) Residential mortgage-backed securities 4.3 (0.1) 0.3 — 4.6 (0.1) Commercial mortgage-backed securities 3.1 — — — 3.1 — Total bonds $ 35.9 $ (0.3) $ 0.3 $ — $ 36.2 $ (0.3) 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 months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 (dollars in millions) Interest on bonds $ 0.8 $ 0.9 Interest on deposits and cash equivalents 0.3 1.1 Total 1.1 2.0 Investment expense (0.2) (0.1) Net investment income $ 0.9 $ 1.9
Schedule of credit ratings	The following tables summarize the credit ratings of investments at March 31, 2021 and December 31, 2020: March 31, 2021 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 73.2 $ 74.0 53.1 % AA+, AA, AA-, A-1 17.0 17.3 12.5 A+, A, A- 36.4 37.1 26.6 BBB+, BBB, BBB- 10.6 10.9 7.8 Total $ 137.2 $ 139.3 100.0 % 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)	3 Months Ended
	Mar. 31, 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 March 31, 2021 and December 31, 2020: March 31, 2021 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities: U.S. Treasury securities and agencies $ 16.0 $ — $ — $ 16.0 Municipal securities — 20.5 — 20.5 Corporate debt securities — 51.7 — 51.7 Residential mortgage-backed securities — 6.1 — 6.1 Commercial mortgage-backed securities — 31.9 — 31.9 Other debt obligations — 10.1 — 10.1 Total fixed maturities 16.0 120.3 — 136.3 Short-term investments 2.2 0.8 — 3.0 Cash equivalents 485.7 — — 485.7 Total assets at fair value $ 503.9 $ 121.1 $ — $ 625.0 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 March 31, 2021 and December 31, 2020 the carrying amounts and fair values of these financial instruments were as follows: Carrying Amount as of March 31, 2021 Estimated Fair Value as of March 31, 2021 Carrying Amount as of December 31, 2020 Estimated Fair Value as of December 31, 2020 (dollars in millions) Long-term debt $ 192.2 $ 211.5 $ 188.2 $ 209.0

LOSS AND LOSS ADJUSTMENT EXPE_2

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Tables)	3 Months Ended
	Mar. 31, 2021
Insurance [Abstract]
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: Three Months Ended March 31, 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 69.8 122.0 Prior years (9.9) 7.9 Total incurred 59.9 129.9 Net paid loss and LAE related to: Current year 25.3 44.1 Prior years 35.3 54.2 Total paid 60.6 98.3 Net loss and LAE reserves, March 31 156.9 153.4 Plus reinsurance recoverable on unpaid losses 83.8 22.2 Gross loss and LAE reserves, March 31 $ 240.7 $ 175.6

LEASES (Tables)

LEASES (Tables)	3 Months Ended
	Mar. 31, 2021
Leases [Abstract]
Schedule of future lease payments	Future lease payments as of March 31, 2021 were as follows: Operating Leases (dollars in millions) Remainder of 2021 $ 2.9 2022 4.3 2023 4.4 2024 4.3 2025 1.5 2026 and thereafter 3.1 Total future lease payments 20.5 Less: imputed interest (4.7) Total lease liabilities $ 15.8
Schedule of Future Minimum Rental Payments for Operating Leases	As previously disclosed in our 2020 Annual Report on Form 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)	3 Months Ended
	Mar. 31, 2021
Debt Disclosure [Abstract]
Schedule of long term debt	The following summarizes the carrying value of long-term debt as of March 31, 2021 and December 31, 2020: March 31, 2021 December 31, 2020 (dollars in millions) Term Loan A $ 99.3 $ 99.5 Term Loan B 100.0 100.0 Total 199.3 199.5 Accrued interest payable 12.7 10.2 Unamortized discount and debt issuance costs (19.8) (21.5) Total $ 192.2 $ 188.2

SHARE-BASED COMPENSATION (Table

SHARE-BASED COMPENSATION (Tables)	3 Months Ended
	Mar. 31, 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 March 31, 2021 2020 (dollars in millions) Share-based compensation expense: Loss and loss adjustment expenses $ 0.1 $ 0.4 Sales and marketing — 1.0 Other insurance expense 0.1 0.9 Technology and development 0.3 5.2 General and administrative 1.8 18.2 Total share-based compensation expense $ 2.3 $ 25.7 The following table provides total share-based compensation expense by type of award: Three Months Ended March 31, 2021 2020 (dollars in millions) Share-based compensation expense: Restricted stock unit expense $ 0.6 $ — Stock option expense 1.7 25.7 Total share-based compensation expense $ 2.3 $ 25.7
Summary of RSU activity	A summary of RSU activity for the three months ended March 31, 2021 is as follows: March 31, 2021 Restricted Stock Units Number of Shares Weighted-Average Aggregate Intrinsic Value (in millions, except exercise price and term amounts) Nonvested at January 1, 2021 0.4 $ 18.41 $ 6.2 Granted 0.1 16.02 Vested — 17.27 0.3 Forfeited, expired or canceled — 21.49 Nonvested at March 31, 2021 0.5 $ 17.75 $ 6.7
Summary of option activity	A summary of option activity for the three months ended March 31, 2021 is as follows: March 31, 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 — — Exercised (1.2) 2.00 12.1 Forfeited, expired or canceled (0.7) 4.80 Outstanding and exercisable at March 31, 2021 8.5 $ 2.24 7.17 $ 88.5

OTHER COMPREHENSIVE INCOME AN_2

OTHER COMPREHENSIVE INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME (Tables)	3 Months Ended
	Mar. 31, 2021
Equity [Abstract]
Schedule of AOCI	The following table presents the changes in our accumulated other comprehensive income (loss), or AOCI, for the three months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 (dollars in millions) Change in net unrealized losses on investments: Accumulated other comprehensive income beginning balance $ 5.6 $ 0.6 Other comprehensive loss before reclassifications (1.1) (1.8) Net realized gains on investments reclassified from AOCI to net loss (2.4) — Net current period other comprehensive loss (3.5) (1.8) Accumulated other comprehensive income (loss) ending balance $ 2.1 $ (1.2)

LOSS PER SHARE (Tables)

LOSS PER SHARE (Tables)	3 Months Ended
	Mar. 31, 2021
Earnings Per Share [Abstract]
Schedule of earnings per share	The following table displays the computation of basic and diluted loss per share of common stock for the three months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 (in millions, except per share amounts) Net loss $ (99.6) $ (105.6) Weighted-average common shares outstanding: basic and diluted 247.1 39.3 Loss per common share: basic and diluted $ (0.40) $ (2.69)
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 March 31, 2021 2020 (in millions) Options to purchase common stock 8.5 12.4 Nonvested shares subject to repurchase 4.6 6.6 Restricted stock units 0.5 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 13.6 181.5

GEOGRAPHICAL BREAKDOWN OF DIR_2

GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM (Tables)	3 Months Ended
	Mar. 31, 2021
Insurance [Abstract]
Schedule of direct premiums written	Direct written premium, or DWP, by state is as follows for the three months ended March 31, 2021 and 2020: Three Months Ended March 31, 2021 2020 Amount % of DWP Amount % of DWP State (dollars in millions) Texas $ 43.0 21.2 % $ 34.3 20.9 % Georgia 19.0 9.4 18.2 11.1 Pennsylvania 10.4 5.1 8.5 5.2 Louisiana 10.3 5.1 6.8 4.1 Colorado 8.9 4.4 4.0 2.4 Utah 8.6 4.2 6.0 3.7 Nevada 8.3 4.1 3.4 2.1 Missouri 7.9 3.9 7.5 4.6 Kentucky 7.5 3.7 11.5 7.0 Arizona 7.3 3.6 8.5 5.2 All others states 71.3 35.3 55.5 33.7 Total $ 202.5 100.0 % $ 164.2 100.0 %

NATURE OF BUSINESS (Details)

NATURE OF BUSINESS (Details)	Mar. 31, 2021
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Ownership percentage	100.00%
Percentage of customers acquired through mobile applications	75.00%

BASIS OF PRESENTATION AND SUM_3

BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Details) - USD ($) $ in Millions	Jan. 01, 2021	Mar. 31, 2021	Dec. 31, 2020
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Total lease liabilities		$ 15.8	$ 15.8
Operating lease, right of use asset		$ 9.7
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	Mar. 31, 2021	Dec. 31, 2020
Debt Securities, Available-for-sale [Line Items]
Total	$ 137.2	$ 218.4
Gross Unrealized Gains	2.4	5.7
Gross Unrealized Losses	(0.3)	(0.1)
Fair Value	139.3	224
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale [Line Items]
Total	16	16.9
Gross Unrealized Gains	0.1	0.1
Gross Unrealized Losses	(0.1)	0
Fair Value	16	17
Municipal securities
Debt Securities, Available-for-sale [Line Items]
Total	20	22.6
Gross Unrealized Gains	0.5	0.8
Gross Unrealized Losses	0	0
Fair Value	20.5	23.4
Corporate debt securities
Debt Securities, Available-for-sale [Line Items]
Total	50.6	87.5
Gross Unrealized Gains	1.2	3.1
Gross Unrealized Losses	(0.1)	(0.1)
Fair Value	51.7	90.5
Residential mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Total	6.2	7.8
Gross Unrealized Gains	0	0
Gross Unrealized Losses	(0.1)	0
Fair Value	6.1	7.8
Commercial mortgage backed securities
Debt Securities, Available-for-sale [Line Items]
Total	31.4	57.1
Gross Unrealized Gains	0.5	1.3
Gross Unrealized Losses	0	0
Fair Value	31.9	58.4
Other debt obligations
Debt Securities, Available-for-sale [Line Items]
Total	10	23.5
Gross Unrealized Gains	0.1	0.4
Gross Unrealized Losses	0	0
Fair Value	10.1	23.9
Total fixed maturities
Debt Securities, Available-for-sale [Line Items]
Total	134.2	215.4
Gross Unrealized Gains	2.4	5.7
Gross Unrealized Losses	(0.3)	(0.1)
Fair Value	136.3	221
Short-term investments
Debt Securities, Available-for-sale [Line Items]
Total	3	3
Gross Unrealized Gains	0	0
Gross Unrealized Losses	0	0
Fair Value	$ 3	$ 3

INVESTMENTS - Unrealized Losses

INVESTMENTS - Unrealized Losses (Details) - USD ($) $ in Millions	Mar. 31, 2021	Dec. 31, 2020
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	$ 35.9	$ 29.6
Less than 12 Months, Unrealized Loss	(0.3)	(0.1)
12 Months or More, Fair Value	0.3	0
12 Months or More, Unrealized Loss	0	0
Total, Fair Value	36.2	29.6
Total, Unrealized Loss	(0.3)	(0.1)
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	14	15.7
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	14	15.7
Total, Unrealized Loss	(0.1)	0
Municipal securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	6.4	2.3
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	6.4	2.3
Total, Unrealized Loss	0	0
Corporate debt securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	8.1	2.9
Less than 12 Months, Unrealized Loss	(0.1)	(0.1)
12 Months or More, Fair Value	0	0
12 Months or More, Unrealized Loss	0	0
Total, Fair Value	8.1	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	4.3	3.7
Less than 12 Months, Unrealized Loss	(0.1)	0
12 Months or More, Fair Value	0.3	0
12 Months or More, Unrealized Loss	0	0
Total, Fair Value	4.6	3.7
Total, Unrealized Loss	(0.1)	0
Commercial mortgage backed securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	3.1	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	3.1	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 ($)	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Investments, Debt and Equity Securities [Abstract]
Other-than-temporary impairments	$ 0	$ 0
Realized gains on investments	2,500,000	0
Realized losses on investments	(100,000)	0
Net realized gains on investments	$ 2,400,000	$ 0

INVESTMENTS - Contractual Matur

INVESTMENTS - Contractual Maturity (Details) - USD ($) $ in Millions	Mar. 31, 2021	Dec. 31, 2020
Amortized Cost
Due in one year or less		$ 9.4
Due after one year through five years		98.8
Due five years through 10 years		9.7
Due after 10 years		19.3
Total	$ 137.2	218.4
Fair Value
Due in one year or less		9.4
Due after one year through five years		100.6
Due five years through 10 years		9.8
Due after 10 years		19.5
Total investments	$ 139.3	$ 224

INVESTMENTS - Net Investment In

INVESTMENTS - Net Investment Income (Details) - USD ($) $ in Millions	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Net Investment Income [Line Items]
Total	$ 1.1	$ 2
Investment expense	(0.2)	(0.1)
Net investment income	0.9	1.9
Bonds
Net Investment Income [Line Items]
Total	0.8	0.9
Deposits and cash equivalents
Net Investment Income [Line Items]
Total	$ 0.3	$ 1.1

INVESTMENTS - Credit Ratings (D

INVESTMENTS - Credit Ratings (Details) - USD ($) $ in Millions	3 Months Ended	6 Months Ended
	Mar. 31, 2021	Jun. 30, 2020	Dec. 31, 2020
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 137.2		$ 218.4
Fair Value	$ 139.3		224
AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	100.00%	100.00%
AAA
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 73.2		116.5
Fair Value	$ 74		118.7
AAA | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	53.10%	53.00%
AA+, AA, AA-, A-1
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 17		22.7
Fair Value	$ 17.3		23.3
AA+, AA, AA-, A-1 | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	12.50%	10.40%
A+, A, A-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 36.4		57.5
Fair Value	$ 37.1		59.4
A+, A, A- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	26.60%	26.50%
BBB+, BBB, BBB-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 10.6		21.7
Fair Value	$ 10.9		$ 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	Mar. 31, 2021	Dec. 31, 2020
Assets
AFS securities	$ 139.3	$ 224
Cash equivalents	485.7	568.4
Total assets at fair value	625	792.4
U.S. Treasury securities and agencies
Assets
AFS securities	16	17
Municipal securities
Assets
AFS securities	20.5	23.4
Corporate debt securities
Assets
AFS securities	51.7	90.5
Residential mortgage-backed securities
Assets
AFS securities	6.1	7.8
Commercial mortgage backed securities
Assets
AFS securities	31.9	58.4
Other debt obligations
Assets
AFS securities	10.1	23.9
Total fixed maturities
Assets
AFS securities	136.3	221
Short-term investments
Assets
AFS securities	3	3
Level 1
Assets
Cash equivalents	485.7	568.4
Total assets at fair value	503.9	587.6
Level 1 | U.S. Treasury securities and agencies
Assets
AFS securities	16	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	16	17
Level 1 | Short-term investments
Assets
AFS securities	2.2	2.2
Level 2
Assets
Cash equivalents	0	0
Total assets at fair value	121.1	204.8
Level 2 | U.S. Treasury securities and agencies
Assets
AFS securities	0	0
Level 2 | Municipal securities
Assets
AFS securities	20.5	23.4
Level 2 | Corporate debt securities
Assets
AFS securities	51.7	90.5
Level 2 | Residential mortgage-backed securities
Assets
AFS securities	6.1	7.8
Level 2 | Commercial mortgage backed securities
Assets
AFS securities	31.9	58.4
Level 2 | Other debt obligations
Assets
AFS securities	10.1	23.9
Level 2 | Total fixed maturities
Assets
AFS securities	120.3	204
Level 2 | Short-term investments
Assets
AFS securities	0.8	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	$ 0

FAIR VALUE OF FINANCIAL INSTR_4

FAIR VALUE OF FINANCIAL INSTRUMENTS - Long Term Debt (Details) - Level 2 - USD ($) $ in Millions	Mar. 31, 2021	Dec. 31, 2020
Carrying amount
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 192.2	$ 188.2
Estimated Fair Value
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 211.5	$ 209

LOSS AND LOSS ADJUSTMENT EXPE_3

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Details) - USD ($) $ in Millions	3 Months Ended
	Mar. 31, 2021	Mar. 31, 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	69.8	122
Prior years	(9.9)	7.9
Total incurred	59.9	129.9
Net paid loss and LAE related to:
Current year	25.3	44.1
Prior years	35.3	54.2
Total paid	60.6	98.3
Net loss and LAE reserves, March 31	156.9	153.4
Plus reinsurance recoverable on unpaid losses	83.8	22.2
Gross loss and LAE reserves, March 31	$ 240.7	$ 175.6

LEASES - Narrative (Details)

LEASES - Narrative (Details) - USD ($) $ in Millions	3 Months Ended
	Mar. 31, 2021	Dec. 31, 2020
Lessee, Lease, Description [Line Items]
Operating lease, weighted-average discount rate	10.80%
Operating lease, weighted-average remaining lease term	5 years 1 month 6 days
Total lease liabilities	$ 15.8	$ 15.8
Operating lease, right of use asset	9.7
Operating lease cost	0.8
Operating lease cash payments	$ 0.9
Maximum
Lessee, Lease, Description [Line Items]
Operating lease, remaining lease term	7 years
Minimum
Lessee, Lease, Description [Line Items]
Operating lease, remaining lease term	1 year

LEASES - Future Lease Payment (

LEASES - Future Lease Payment (Details) - USD ($) $ in Millions	Mar. 31, 2021	Dec. 31, 2020
Leases [Abstract]
Remainder of 2021	$ 2.9
2022	4.3
2023	4.4
2024	4.3
2025	1.5
2026 and thereafter	3.1
Total future lease payments	20.5
Less: imputed interest	(4.7)
Total lease liabilities	$ 15.8	$ 15.8

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 - Schedule Of De

LONG-TERM DEBT - Schedule Of Debt (Details) - USD ($) $ in Millions	Mar. 31, 2021	Dec. 31, 2020
Debt Instrument [Line Items]
Long-term Debt, Total	$ 192.2	$ 188.2
Term Loan A
Debt Instrument [Line Items]
Long-term Debt, Gross	199.3	199.5
Accrued interest payable	12.7	10.2
Unamortized discount and debt issuance costs	(19.8)	(21.5)
Long-term Debt, Total	192.2	188.2
Term Loan A | Term Loan A
Debt Instrument [Line Items]
Long-term Debt, Gross	99.3	99.5
Term Loan A | Term Loan B
Debt Instrument [Line Items]
Long-term Debt, Gross	$ 100	$ 100

LONG-TERM DEBT - Narrative (Det

LONG-TERM DEBT - Narrative (Details) - USD ($)	3 Months Ended		12 Months Ended
	Mar. 31, 2021	Mar. 31, 2020	Dec. 31, 2020
Debt Instrument [Line Items]
Letters of credit outstanding	$ 0
Payment-in-kind interest expense	$ 2,400,000	$ 2,200,000	$ 2,200,000
Term Loan A | Term Loan A | LIBOR
Debt Instrument [Line Items]
Variable rate percentage	4.00%
Term Loan A | Amended Term Loan B | LIBOR
Debt Instrument [Line Items]
Variable rate percentage	10.50%
Revolving Loan | Line of Credit
Debt Instrument [Line Items]
Maximum borrowing capacity	$ 100,000,000
Revolving Loan | Line of Credit | Amended Term Loan A
Debt Instrument [Line Items]
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%

INCOME TAXES (Details)

INCOME TAXES (Details)	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Income Tax Disclosure [Abstract]
Effective income tax rate	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
	Mar. 31, 2021	Mar. 31, 2020
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 2.3	$ 25.7
Stock option expense
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost, period of recognition	6 years
Restricted stock unit expense
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 0.6	0
Unrecognized compensation cost	$ 8.6
Unrecognized compensation cost, period of recognition	4 years
Options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 1.7	25.7
Unrecognized compensation cost	$ 7.6
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)	30

SHARE-BASED COMPENSATION - Shar

SHARE-BASED COMPENSATION - Share-based Compensation Expense (Details) - USD ($) $ in Millions	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 2.3	$ 25.7
RSUs
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.6	0
Options
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	1.7	25.7
Loss and loss adjustment expenses
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.1	0.4
Sales and marketing
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0	1
Other insurance expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.1	0.9
Technology and development
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.3	5.2
General and administrative
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 1.8	$ 18.2

SHARE-BASED COMPENSATION - RSU

SHARE-BASED COMPENSATION - RSU Activity (Details) - RSUs $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended
	Mar. 31, 2021USD ($)$ / sharesshares
Number of Shares
Beginning balance (in shares) | shares	0.4
Granted (in shares) | shares	0.1
Vested (in shares) | shares	0
Forfeited, expired or canceled (in shares) | shares	0
Ending balance (in shares) | shares	0.5
Weighted-Average Grant Date Fair Value per Share
Beginning balance, weighted-average grant date fair value (in dollars per shares) | $ / shares	$ 18.41
Granted, weighted-average grant date fair value (in dollars per shares) | $ / shares	16.02
Vested, weighted-average grant date fair value (in dollars per shares) | $ / shares	17.27
Forfeited, expired or canceled, weighted-average grant date fair value (in dollars per share) | $ / shares	21.49
Ending balance, weighted-average grant date fair value (in dollars per shares) | $ / shares	$ 17.75
Aggregate Intrinsic Value
Beginning balance | $	$ 6.2
Vested | $	0.3
Ending balance | $	$ 6.7

SHARE-BASED COMPENSATION - Opti

SHARE-BASED COMPENSATION - Option Activity (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended	12 Months Ended
	Mar. 31, 2021	Dec. 31, 2020
Number of Shares
Outstanding, beginning balance (in shares)	10.4
Granted (in shares)	0
Exercised (in shares)	(1.2)
Forfeited, expired or canceled (in shares)	(0.7)
Outstanding, ending balance (in shares)	8.5	10.4
Weighted-Average Exercise Price
Outstanding, beginning balance, weighted-average exercise price (in dollars per share)	$ 2.39
Granted, weighted-average exercise price (in dollars per share)	0
Exercised, weighted-average exercise price (in dollars per share)	2
Forfeited, expired and canceled, weighted-average exercise price (in dollars per share)	4.80
Outstanding, ending balance, weighted-average exercise price (in dollars per share)	$ 2.24	$ 2.39
Outstanding, weighted-average remaining contractual term (in years)	7 years 2 months 1 day	7 years 9 months
Exercisable, weighted-average remaining contractual term (in years)	7 years 2 months 1 day	7 years 9 months
Outstanding, aggregate intrinsic value	$ 88.5	$ 137.7
Exercised, aggregate intrinsic value	12.1
Exercisable, aggregate intrinsic value	$ 88.5	$ 137.7

OTHER COMPREHENSIVE INCOME AN_3

OTHER COMPREHENSIVE INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME (Details) - USD ($) $ in Millions	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	$ 1,032.4	$ (374)
Net current period other comprehensive loss	(3.5)	(1.8)
Ending balance	934.3	(455.4)
Change in net unrealized losses on investments:
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	5.6	0.6
Other comprehensive loss before reclassifications	(1.1)	(1.8)
Net realized gains on investments reclassified from AOCI to net loss	(2.4)	0
Net current period other comprehensive loss	(3.5)	(1.8)
Ending balance	$ 2.1	$ (1.2)

LOSS PER SHARE (Details)

LOSS PER SHARE (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Earnings Per Share [Abstract]
Net loss	$ (99.6)	$ (105.6)
Weighted-average common shares outstanding: basic and diluted (in shares)	247.1	39.3
Loss per common share: basic and diluted (in dollars per share)	$ (0.40)	$ (2.69)

LOSS PER SHARE - Schedule of An

LOSS PER SHARE - Schedule of Anti-Dilutive Securities (Details) - shares shares in Millions	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities	13.6	181.5
Options to purchase common stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities	8.5	12.4
Nonvested shares subject to repurchase
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities	4.6	6.6
RSUs
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities	0.5	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	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	0	0.6

GEOGRAPHICAL BREAKDOWN OF DIR_3

GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM (Details) - USD ($) $ in Millions	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Effects of Reinsurance [Line Items]
Direct premiums written	$ 202.5	$ 164.2
Texas
Effects of Reinsurance [Line Items]
Direct premiums written	43	34.3
Georgia
Effects of Reinsurance [Line Items]
Direct premiums written	19	18.2
Pennsylvania
Effects of Reinsurance [Line Items]
Direct premiums written	10.4	8.5
Louisiana
Effects of Reinsurance [Line Items]
Direct premiums written	10.3	6.8
Colorado
Effects of Reinsurance [Line Items]
Direct premiums written	8.9	4
Utah
Effects of Reinsurance [Line Items]
Direct premiums written	8.6	6
Nevada
Effects of Reinsurance [Line Items]
Direct premiums written	8.3	3.4
Missouri
Effects of Reinsurance [Line Items]
Direct premiums written	7.9	7.5
Kentucky
Effects of Reinsurance [Line Items]
Direct premiums written	7.5	11.5
Arizona
Effects of Reinsurance [Line Items]
Direct premiums written	7.3	8.5
All others states
Effects of Reinsurance [Line Items]
Direct premiums written	$ 71.3	$ 55.5
Geographic Concentration Risk | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	100.00%	100.00%
Geographic Concentration Risk | Texas | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	21.20%	20.90%
Geographic Concentration Risk | Georgia | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	9.40%	11.10%
Geographic Concentration Risk | Pennsylvania | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	5.10%	5.20%
Geographic Concentration Risk | Louisiana | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	5.10%	4.10%
Geographic Concentration Risk | Colorado | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.40%	2.40%
Geographic Concentration Risk | Utah | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.20%	3.70%
Geographic Concentration Risk | Nevada | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.10%	2.10%
Geographic Concentration Risk | Missouri | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	3.90%	4.60%
Geographic Concentration Risk | Kentucky | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	3.70%	7.00%
Geographic Concentration Risk | Arizona | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	3.60%	5.20%
Geographic Concentration Risk | All others states | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	35.30%	33.70%