Root (ROOT) 10-Q 2 Dec 20 2020 Q3 Quarterly report Financial data

COVER PAGE

COVER PAGE - shares	9 Months Ended
	Sep. 30, 2020	Nov. 24, 2020
Entity Listings [Line Items]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Sep. 30, 2020
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	No
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	2020
Document Fiscal Period Focus	Q3
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		59,443,588
Class B Common Stock
Entity Listings [Line Items]
Entity Common Stock, Shares Outstanding		191,354,938

CONDENSED CONSOLIDATED BALANCE

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Investments:
Fixed maturities available-for sale, at fair value (amortized cost: $216.4 and $118.7 at September 30, 2020 and December 31, 2019, respectively)	$ 222	$ 119.3
Short-term investments (amortized cost: $2.5 and $3.5 at September 30, 2020 and December 31, 2019, respectively)	2.5	3.5
Total investments	224.5	122.8
Cash and cash equivalents	217.8	391.7
Restricted cash	1	24.9
Premiums receivable, net of allowance of $7.1 and $2.0 at September 30, 2020 and December 31, 2019, respectively	138.4	122.7
Reinsurance recoverable	104.1	25.3
Prepaid reinsurance premiums	119.1	17.4
Fixed assets, net	9.6	10.2
Deferred acquisition costs	1.8	3.3
Other assets	22.2	10.3
Total assets	838.5	728.6
Liabilities:
Loss and loss adjustment expense reserves	225.3	140.7
Unearned premiums	165.1	145.4
Long-term debt and warrants	220	192.2
Reinsurance premiums payable	166.4	25.7
Accounts payable and accrued expenses	61.5	29.8
Other liabilities	10.2	8.4
Total liabilities	848.5	542.2
Commitments and Contingencies (Note 11)
Redeemable convertible preferred stock, $0.0001 par value, 161.8 and 158.9 shares issued and outstanding at September 30, 2020 and December 31, 2019, respectively (liquidation preference of $597.5 and $549.8 at September 30, 2020 and December 31, 2019, respectively) (Note 8)	560.4	560.4
Stockholders’ deficit:
Common stock, $0.0001 par value, 42.5 and 44.4 shares issued and outstanding at September 30, 2020 and December 31, 2019, respectively (Note 8)	0	0
Treasury stock, at cost	(0.8)	(0.1)
Additional paid-in capital	39.5	10.5
Accumulated other comprehensive income	5.6	0.6
Accumulated loss	(614.7)	(385)
Total stockholders’ deficit	(570.4)	(374)
Total liabilities, redeemable convertible preferred stock and stockholders’ deficit	$ 838.5	$ 728.6

CONDENSED CONSOLIDATED BALANC_2

CONDENSED CONSOLIDATED BALANCE SHEETS - UNAUDITED (Parenthetical) - USD ($) shares in Millions, $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Statement of Financial Position [Abstract]
Amortized cost, fixed maturities	$ 216.4	$ 118.7
Amortized cost, short term investments	2.5	3.5
Allowance for premiums receivable	$ 7.1	$ 2
Temporary equity, par value (in dollars per share)	$ 0.0001	$ 0.0001
Temporary equity, shares outstanding (in shares)	161.8	158.9
Temporary equity, shares issued (in shares)	161.8	158.9
Temporary equity, liquidation preference	$ 597.5	$ 549.8
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock, shares issued (in shares)	42.5	44.4
Common stock, shares outstanding (in shares)	42.5	44.4

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, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Income Statement [Abstract]
Net premiums earned	$ 44.9	$ 75.8	$ 278.4	$ 174.4
Net investment income	1.1	1.1	4.3	2.8
Net realized gains on investments	0.1	0	0.2	0
Fee income	4.4	2.7	13	6.5
Total revenue	50.5	79.6	295.9	183.7
Operating expenses:
Loss and loss adjustment expenses	76.1	100.9	303.3	210.5
Sales and marketing	36.9	34.4	90.1	73.6
Other insurance (benefit) expense	(26.3)	15.2	0.3	34.1
Technology and development	12.9	7	40.2	15.4
General and administrative	16.6	9	58.8	31.4
Total operating expenses	116.2	166.5	492.7	365
Interest expense	19.5	13.3	32.9	15.9
Loss before income tax expense	(85.2)	(100.2)	(229.7)	(197.2)
Income tax expense	0	0	0	0
Net loss	(85.2)	(100.2)	(229.7)	(197.2)
Other comprehensive income:
Changes in unrealized gain on investments	0.1	0.1	5	0.8
Comprehensive loss	$ (85.1)	$ (100.1)	$ (224.7)	$ (196.4)
Loss per common share: basic and diluted (in dollars per share)	$ (2.20)	$ (2.88)	$ (5.94)	$ (5.99)
Weighted-average common shares outstanding: basic and diluted (in shares)	38.8	34.8	38.7	32.9

CONDENSED CONSOLIDATED STATEM_2

CONDENSED CONSOLIDATED STATEMENTS OF REDEEMABLE CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS’ DEFICIT - UNAUDITED - USD ($) shares in Millions, $ in Millions	Total	Series E Preferred Stock	Common Stock	Treasury Stock	Additional Paid-in Capital	Accumulated Other Comprehensive Income	Accumulated Loss
Beginning Balance at Dec. 31, 2018	$ 189.6
Beginning balance (in shares) at Dec. 31, 2018	136.4
Increase (Decrease) in Temporary Equity [Roll Forward]
Preferred stock—series E, net of issuance costs (in shares)		21.2
Preferred stock—series E, net of issuance costs		$ 349.9
Preferred stock—SAFE conversion (in shares)	1.3
Preferred stock—SAFE conversion	$ 21.2
Ending balance (in shares) at Sep. 30, 2019	158.9
Ending Balance at Sep. 30, 2019	$ 560.7
Beginning balance at Dec. 31, 2018	(102.7)		$ 0	$ (0.1)	$ 0	$ 0	$ (102.6)
Beginning balance (in shares) at Dec. 31, 2018			41.5
Treasury stock, beginning balance (in shares) at Dec. 31, 2018				4.5
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(197.2)						(197.2)
Changes in other comprehensive income	0.8					0.8
Tender offer and subsequent conversion (Note 9)	8.6				8.6
Common stock—option exercises (in shares)			2.8
Common stock—option exercises	1.8				1.8
Reclassification of early-exercised stock option to liabilities	(1.3)				(1.3)
Common stock—shared-based compensation expense	0.8				0.8
Treasury stock, ending balance (in shares) at Sep. 30, 2019				4.5
Ending balance (in shares) at Sep. 30, 2019			44.3
Ending balance at Sep. 30, 2019	(289.2)		$ 0	$ (0.1)	9.9	0.8	(299.8)
Beginning Balance at Jun. 30, 2019	$ 189.6
Beginning balance (in shares) at Jun. 30, 2019	136.4
Increase (Decrease) in Temporary Equity [Roll Forward]
Preferred stock—series E, net of issuance costs (in shares)		21.2
Preferred stock—series E, net of issuance costs		$ 349.9
Preferred stock—SAFE conversion (in shares)	1.3
Preferred stock—SAFE conversion	$ 21.2
Ending balance (in shares) at Sep. 30, 2019	158.9
Ending Balance at Sep. 30, 2019	$ 560.7
Beginning balance at Jun. 30, 2019	(189.5)		$ 0	$ (0.1)	9.5	0.7	(199.6)
Beginning balance (in shares) at Jun. 30, 2019			43.2
Treasury stock, beginning balance (in shares) at Jun. 30, 2019				4.5
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net loss	(100.2)						(100.2)
Changes in other comprehensive income	0.1					0.1
Common stock—option exercises (in shares)			1.1
Common stock—option exercises	1.2				1.2
Reclassification of early-exercised stock option to liabilities	(1.1)				(1.1)
Common stock—shared-based compensation expense	0.3				0.3
Treasury stock, ending balance (in shares) at Sep. 30, 2019				4.5
Ending balance (in shares) at Sep. 30, 2019			44.3
Ending balance at Sep. 30, 2019	(289.2)		$ 0	$ (0.1)	9.9	0.8	(299.8)
Beginning Balance at Dec. 31, 2019	$ 560.4	$ 370.8
Beginning balance (in shares) at Dec. 31, 2019	158.9	22.5
Increase (Decrease) in Temporary Equity [Roll Forward]
Tender offer and subsequent conversion (Note 9) (in shares)	2.9
Ending balance (in shares) at Sep. 30, 2020	161.8	25.4
Ending Balance at Sep. 30, 2020	$ 560.4	$ 370.8
Beginning balance at Dec. 31, 2019	(374)		$ 0	$ (0.1)	10.5	0.6	(385)
Beginning balance (in shares) at Dec. 31, 2019			44.4
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	5					5
Tender offer and subsequent conversion (Note 9) (in shares)			(2.9)
Tender offer and subsequent conversion (Note 9)	$ 25.1				25.1
Common stock—option exercises (in shares)	1.5		1.5
Common stock—option exercises	$ 1.2				1.2
Reclassification of early-exercised stock option to liabilities (in shares)			(0.1)
Reclassification of early-exercised stock option to liabilities	0.3				0.3
Common stock—shared-based compensation expense	1.9				1.9
Settlement of related party loan (Note 10) (in shares)			(0.4)	0.1
Settlement of related party loan (Note 10)	(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			42.5
Ending balance at Sep. 30, 2020	(570.4)		$ 0	$ (0.8)	39.5	5.6	(614.7)
Beginning Balance at Jun. 30, 2020	$ 560.4
Beginning balance (in shares) at Jun. 30, 2020	161.8
Ending balance (in shares) at Sep. 30, 2020	161.8	25.4
Ending Balance at Sep. 30, 2020	$ 560.4	$ 370.8
Beginning balance at Jun. 30, 2020	(487.2)		$ 0	$ (0.8)	37.6	5.5	(529.5)
Beginning balance (in shares) at Jun. 30, 2020			41.4
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	0.1					0.1
Common stock—option exercises (in shares)			1
Common stock—option exercises	0.9				0.9
Reclassification of early-exercised stock option to liabilities (in shares)			(0.1)
Reclassification of early-exercised stock option 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			42.5
Ending balance at Sep. 30, 2020	$ (570.4)		$ 0	$ (0.8)	$ 39.5	$ 5.6	$ (614.7)

CONDENSED CONSOLIDATED STATEM_3

CONDENSED CONSOLIDATED STATEMENTS OF REDEEMABLE CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS’ DEFICIT - UNAUDITED (Parenthetical) - USD ($) $ in Millions	3 Months Ended	9 Months Ended
	Sep. 30, 2019	Sep. 30, 2019
Statement of Stockholders' Equity [Abstract]
Issuance costs	$ 0.1	$ 0.1

CONDENSED CONSOLIDATED STATEM_4

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - UNAUDITED - USD ($) $ in Millions	9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019
Cash flows from operating activities:
Net loss	$ (229.7)	$ (197.2)
Adjustments to reconcile net loss to net cash used in operating activities:
Share-based compensation	1.9	0.8
Tender offer	25.1	8.6
Depreciation and amortization	10.6	2.4
Bad debt expense	16.7	5.4
Warrants fair value adjustment	16	0
Payment-in-kind interest expense	6.8	0
Realized gains on investments	(0.2)	0
SAFE fair value adjustment	0	11.2
Changes in operating assets and liabilities:
Premiums receivable	(32.4)	(66.7)
Reinsurance recoverable	(78.8)	(22.3)
Prepaid reinsurance premiums	(101.7)	(6.2)
Deferred acquisition costs	1.5	(1.6)
Other assets	(9.6)	(0.6)
Losses and loss adjustment expenses reserves	84.6	77.2
Unearned premiums	19.7	74.1
Reinsurance premiums payable	140.7	25.4
Accounts payable and accrued expenses	31.6	15.9
Other liabilities	2.4	1
Net cash used in operating activities	(94.8)	(72.6)
Cash flows from investing activities:
Purchases of investments	(138.1)	(104.3)
Proceeds from maturities, call and pay downs of investments	31.2	29.9
Sales of investments	9.4	0
Capitalization of internally developed software	(3.9)	(4.1)
Purchases of fixed assets	(1.7)	(3.8)
Net cash used in investing activities	(103.1)	(82.3)
Cash flows from financing activities:
Proceeds from exercise of stock options	1.4	1.8
Proceeds from issuance of preferred stock, net	0	349.9
Purchase of treasury stock	(0.2)	0
Proceeds from debt issuance	13.5	100
Debt issuance costs	(1.4)	(2.7)
Repayments of long-term debt	(13.2)	(15.3)
Proceeds from SAFE	0	10
Net cash provided by financing activities	0.1	443.7
Net (decrease) increase in cash, cash equivalents and restricted cash	(197.8)	288.8
Cash, cash equivalents and restricted cash at beginning of year	416.6	122.3
Cash, cash equivalents and restricted cash at end of year	218.8	411.1
Supplemental disclosures:
Interest paid	3.3	2.8
Income taxes paid	0	0
Leasehold improvements - non-cash	0	0.4
Purchase of treasury stock - non-cash	$ 0.5	$ 0

NATURE OF BUSINESS

NATURE OF BUSINESS	9 Months Ended
	Sep. 30, 2020
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 Root Insurance Company, an Ohio 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 revolutionizing personal insurance with a pricing model based upon fairness and a modern customer experience. We operate a direct-to-consumer model with more than 75% of our customers acquired through mobile applications. We offer auto and renters insurance products underwritten by Root Insurance Company. As of September 30, 2020, we wrote auto policies in 30 states and were licensed in six additional states and the District of Columbia. As of September 30, 2020, we offered renters insurance in nine states.

SIGNIFICANT ACCOUNTING POLICIES

SIGNIFICANT ACCOUNTING POLICIES	9 Months Ended
	Sep. 30, 2020
Accounting Policies [Abstract]
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 final prospectus dated October 27, 2020, as filed with the SEC pursuant to Rule 424(b)(4) under the Securities Act of 1933 on October 29, 2020. 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 December 2019, COVID-19 was first reported in Wuhan, China and in March 2020, the World Health Organization declared a global pandemic. The global pandemic has severely impacted businesses worldwide, including within the insurance industry. We have been impacted by certain individual state bulletins that outline 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. COVID-19 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. Other Insurance Expense —Other insurance expense includes underwriting expenses; credit card and policy processing expenses; premium write-offs; insurance license expenses; and salaries, health benefits, bonuses, employee retirement plan related expenses, share-based compensation expenses, and overhead allocated based on headcount related to actuarial and certain data science activities. Other insurance expense also includes amortization of deferred acquisition costs like premium taxes and report costs related to the successful acquisition of a policy. Other insurance expense is expensed as incurred, except for costs related to deferred acquisition costs that are capitalized and subsequently amortized over the same period in which the related premiums are earned. These expenses are also recognized net of ceding commissions earned from our quota share reinsurance agreements. The ceding commission provides for reimbursement of both direct and other periodic acquisition costs, including certain underwriting and marketing costs, and is presented as a reduction of other insurance expense. Under our new quota share reinsurance structure effective July 1, 2020, which is on a loss occurring basis, we began ceding approximately 70% of direct earned premiums to our third-party reinsurers. We recognize ceding commissions in proportion to recognition of the direct written premiums during the quarter, including the remaining unearned premiums on ceded policies upon the inception of our new quota share reinsurance agreement. Deferred Offering Costs —Deferred offering costs, which primarily consist of legal, accounting, and other third-party fees directly related to our initial public offering, or IPO, are capitalized as incurred. Upon consummation of the IPO, these deferred offering costs were offset against the IPO proceeds. Deferred offering costs were $0.7 million as of September 30, 2020. Recently Adopted Financial Accounting Standards —In August 2018, the FASB issued Accounting Standards Update No. 2018-15, Intangibles—Goodwill and Other—Internal-Use Software (Subtopic 350-40): Customer’s Accounting for Fees Paid in a Cloud Computing Arrangement , to help entities evaluate the accounting for fees paid by a customer in a cloud computing arrangement (hosting arrangement) by providing guidance for determining when the arrangement includes a software license. We early adopted ASU 2018-15 on January 1, 2020. The adoption of this standard did not have a material impact on our condensed consolidated financial statements or notes to the condensed consolidated financial statements. In December 2019, the FASB issued ASU 2019-12, Income Taxes (Topic 740)—Simplifying the Accounting for Income Taxes. The amendments in the update simplify the accounting for income taxes by, among other things, removing the exception to the incremental approach for intraperiod tax allocation when there is a loss from continuing operations and income or a gain from other items like comprehensive income, and recognizing franchise tax that is partially based on income as an income-based tax. We early adopted ASU 2019-12 on January 1, 2020. The adoption of this standard did not have a material impact on our condensed consolidated financial statements or notes to the condensed consolidated financial statements. 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 February 2016, the FASB issued ASU 2016-02, Leases (Topic 842) . The main provision of ASU 2016-02 requires the recognition of lease assets and lease liabilities by lessees for those leases classified as operating leases under previous GAAP. The effective date of ASU 2016-02 is for annual reporting periods beginning after December 15, 2021, and interim reporting periods beginning after December 15, 2022. We are currently evaluating the impact of this ASU. 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 this ASU.

INVESTMENTS

INVESTMENTS	9 Months Ended
	Sep. 30, 2020
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, 2020 and December 31, 2019 are as follows: September 30, 2020 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Bonds and short-term investments: U.S. Treasury securities and agencies $ 5.1 $ 0.1 $ — $ 5.2 Municipal securities 20.2 0.8 — 21.0 Corporate debt securities 95.8 3.1 — 98.9 Residential mortgage-backed securities 11.1 0.1 (0.1) 11.1 Commercial mortgage backed securities 57.9 1.2 (0.1) 59.0 Other debt obligations 28.8 0.5 — 29.3 Total $ 218.9 $ 5.8 $ (0.2) $ 224.5 December 31, 2019 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Bonds and short-term investments: U.S. Treasury securities and agencies $ 12.7 $ 0.1 $ — $ 12.8 Municipal securities 10.2 0.1 — 10.3 Corporate debt securities 38.8 0.4 (0.1) 39.1 Residential mortgage-backed securities 3.3 — — 3.3 Commercial mortgage backed securities 31.5 0.1 (0.1) 31.5 Other debt obligations 25.7 0.1 — 25.8 Total $ 122.2 $ 0.8 $ (0.2) $ 122.8 The following tables reflect the gross unrealized losses, fair value on bonds, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at September 30, 2020 and December 31, 2019: September 30, 2020 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Bonds: Municipal securities $ 2.7 $ — $ — $ — $ 2.7 $ — Corporate debt securities 7.6 — — — 7.6 — Residential mortgage-backed securities 6.8 (0.1) — — 6.8 (0.1) Commercial mortgage-backed securities 3.6 (0.1) — — 3.6 (0.1) Total bonds $ 20.7 $ (0.2) $ — $ — $ 20.7 $ (0.2) December 31, 2019 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Bonds: Municipal securities $ 5.5 $ — $ — $ — $ 5.5 $ — Corporate debt securities 12.8 (0.1) — — 12.8 (0.1) Residential mortgage-backed securities 1.9 — — — 1.9 — Commercial mortgage-backed securities 24.5 (0.1) — — 24.5 (0.1) Other debt obligations 7.4 — — — 7.4 — Total bonds $ 52.1 $ (0.2) $ — $ — $ 52.1 $ (0.2) There were no other-than-temporary impairments recognized in the nine months ended September 30, 2020 or 2019, respectively. The amortized cost and fair value of short-term investments and fixed maturity securities by contractual maturity at September 30, 2020 and December 31, 2019 are as follows: September 30, 2020 December 31, 2019 Amortized Cost Fair Value Amortized Cost Fair Value (dollars in millions) Due in one year or less $ 13.7 $ 13.9 $ 14.3 $ 14.3 Due after one year through five years 149.9 154.6 81.6 82.1 Due five years through 10 years 18.1 18.4 4.9 4.9 Due after 10 years 37.2 37.6 21.4 21.5 Total $ 218.9 $ 224.5 $ 122.2 $ 122.8 Net realized gains on short-term investments and fixed maturity securities were $0.1 million and zero for the three months ended September 30, 2020 and 2019, respectively. Net realized gains on short-term investments and fixed maturity securities were $0.2 million and zero for the nine months ended September 30, 2020 and 2019, respectively. The following table sets forth the components of net investment income for the three months and nine months ended September 30, 2020 and 2019: Three Months Ended September 30, Nine Months Ended September 30, 2020 2019 2020 2019 (dollars in millions) Interest on bonds $ 1.1 $ (0.8) $ 3.2 $ 1.0 Interest on deposits and cash equivalents 0.1 2.0 1.4 2.0 Total 1.2 1.2 4.6 3.0 Investment expense (0.1) (0.1) (0.3) (0.2) Net investment income $ 1.1 $ 1.1 $ 4.3 $ 2.8 The following tables summarize the credit ratings of investments at September 30, 2020 and December 31, 2019: September 30, 2020 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 113.3 $ 115.5 51.4 % AA+, AA, AA-, A-1 19.4 20.1 9.0 A+, A, A- 65.0 66.9 29.8 BBB+, BBB, BBB- 21.2 22.0 9.8 Total $ 218.9 $ 224.5 100.0 % December 31, 2019 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 78.8 $ 79.0 64.3 % AA+, AA, AA-, A-1 8.7 8.8 7.2 A+, A, A- 26.6 26.9 21.9 BBB+, BBB, BBB- 8.1 8.1 6.6 Total $ 122.2 $ 122.8 100.0 %

FAIR VALUE OF FINANCIAL INSTRUM

FAIR VALUE OF FINANCIAL INSTRUMENTS	9 Months Ended
	Sep. 30, 2020
Fair Value Disclosures [Abstract]
FAIR VALUE OF FINANCIAL INSTRUMENTS	FAIR VALUE OF FINANCIAL INSTRUMENTS The following tables provide information about our financial assets and liabilities measured and reported at fair value: September 30, 2020 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities $ 2.7 $ 219.3 $ — $ 222.0 Short-term investments 2.5 — — 2.5 Cash equivalents 167.7 — — 167.7 Total Assets at fair value $ 172.9 $ 219.3 $ — $ 392.2 Liabilities Warrant liability $ — $ — $ 36.3 $ 36.3 Total Liabilities at fair value $ — $ — $ 36.3 $ 36.3 December 31, 2019 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities $ 9.8 $ 109.5 $ — $ 119.3 Short-term investments 3.0 0.5 — 3.5 Cash equivalents 316.6 — — 316.6 Total Assets at fair value $ 329.4 $ 110.0 $ — $ 439.4 Liabilities Warrant liability $ — $ — $ 20.3 $ 20.3 Total Liabilities at fair value $ — $ — $ 20.3 $ 20.3 We estimate the fair value of all our different classes of Level 2 fixed maturities and short-term investments by using a combination of an independent pricing vendor or broker/dealer, pricing models, quoted prices of securities with similar characteristics or discounted cash flows. We have financial liabilities categorized as level 3 in the table above for warrants issued and outstanding. To calculate the fair value we utilized the Black-Scholes Merton, or BSM, approach. The significant inputs in calculating the fair value of the warrants were the current price from the most recently completed Internal Revenue Code 409a valuation, or 409a, the current risk-free rate used by the United States Treasury, the expected term and the volatility assumption. The BSM calculation yielded a fair value of $12.9699 per share for each of the 2.8 million warrants. During the three and nine months ended September 30, 2020, we recognized a $13.7 million and $16.0 million adjustment to the fair value of the warrants within interest expense of our condensed consolidated statements of operations and comprehensive loss. 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, 2020 and December 31, 2019 the carrying amounts and fair values of these financial instruments were as follows: Carrying amount as of September 30, 2020 Estimated Fair Value as of September 30, 2020 Carrying amount as of December 31, 2019 Estimated Fair Value as of December 31, 2019 (dollars in millions) Long-term debt $ 184.4 $ 207.7 $ 172.7 $ 200.8

LOSS AND LOSS ADJUSTMENT EXPENS

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES	9 Months Ended
	Sep. 30, 2020
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, 2020 2019 (dollars in millions) Gross loss and LAE reserves, January 1 $ 140.7 $ 33.3 Reinsurance recoverable on unpaid losses (18.9) (11.4) Net loss and LAE reserves, January 1 121.8 21.9 Net incurred loss and LAE related to: Current year 282.0 204.4 Prior years 21.3 6.1 Total incurred 303.3 210.5 Net paid loss and LAE related to: Current year 165.8 125.2 Prior years 100.4 23.3 Total paid 266.2 148.5 Net loss and LAE reserves, September 30 158.9 83.9 Plus reinsurance recoverable on unpaid losses 66.4 26.5 Gross loss and LAE reserves, September 30 $ 225.3 $ 110.4 Incurred losses and LAE attributable to prior accident years was an increase of $21.3 million and $6.1 million for the nine months ended September 30, 2020 and 2019, respectively. 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.

LONG-TERM DEBT

LONG-TERM DEBT	9 Months Ended
	Sep. 30, 2020
Debt Disclosure [Abstract]
LONG-TERM DEBT	LONG-TERM DEBT The following summarizes the carrying value of long-term debt and warrants as of September 30, 2020 and December 31, 2019: September 30, 2020 December 31, 2019 (dollars in millions) Term Loan A $ 99.8 $ 99.5 Term Loan B 100.0 100.0 Warrants 36.3 20.3 Total 236.1 219.8 Accrued interest payable 7.7 0.9 Unamortized discount and debt issuance costs (23.8) (28.5) Total $ 220.0 $ 192.2 In September 2020, we amended Term Loan A to add new financial institutions (Wells Fargo, Barclays, Morgan Stanley and Deutsche Bank) to the syndicate in the amount of $13.5 million and extended the maturity of Term Loan A to October 15, 2021. As a part of the amended Term Loan A, the syndicate committed, pro rata, to a new $100 million revolving loan, all of which was available to borrow as of September 30, 2020. 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 as of September 30, 2020. In order to amend Term Loan A, we also amended Term Loan B as the terms are pari passu. Notable changes to Term Loan B include removal of the pay-down requirement after the completion of our IPO, an interest rate increase of 3.5% (to 3-month LIBOR plus an applicable margin of 10.5%) starting March 2021, and elimination of payment-in-kind, or PIK, interest after October 15, 2021. We currently pay interest pursuant to the terms of the loan agreements and have the option to 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 September 30, 2020. Deferred PIK interest was $7.6 million and $0.8 million as of September 30, 2020 and December 31, 2019.

INCOME TAXES

INCOME TAXES	9 Months Ended
	Sep. 30, 2020
Income Tax Disclosure [Abstract]
INCOME TAXES	INCOME TAXES The consolidated effective tax rate was 0.0% for all periods for the three months and nine months ended September 30, 2020 and 2019. 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, 2020, we did not have any unrecognized tax benefits for uncertain tax positions and had no interest or penalties related to uncertain tax positions.

CAPITAL STOCK

CAPITAL STOCK	9 Months Ended
	Sep. 30, 2020
Equity [Abstract]
CAPITAL STOCK	CAPITAL STOCKAs of September 30, 2020 and December 31, 2019, our certificate of incorporation, as amended and restated, authorized 40.5 million of Series A preferred voting stock, 41.8 million Series B preferred voting stock, 35.4 million Series C voting preferred shares, 19.6 million of Series D preferred voting stock and 32.7 million and 30.1 million of Series E preferred voting stock, respectively. All classes of stock have a par value of $0.0001 per share. The redeemable convertible preferred stock is recorded in mezzanine equity because while it is not mandatorily redeemable, it will become redeemable at the option of the preferred stockholders upon the occurrence of a deemed liquidation event that is considered not solely within our control. As of September 30, 2020 and December 31, 2019, our certificate of incorporation, as amended and restated, authorized 269.0 million and 266.0 million common shares of voting stock shares of par value $0.0001 per share common stock, respectively. The voting, dividend, and liquidation rights of the holders of the common stock are subject to and qualified by the rights, powers, and preferences of the holders of the preferred stock. The following table displays our capital stock as of September 30, 2020 and December 31, 2019: September 30, 2020 December 31, 2019 Shares Authorized Shares Issued and Outstanding Carrying Value Shares Authorized Shares Issued and Outstanding Carrying Value Common Stock Issuable Upon Conversion Conversion Price Per Share Redeemable on or After (in millions, except per share amounts) Common Stock-Voting (1) 269.0 42.5 $ — 266.0 44.4 $ — — Preferred Stock (1) Preferred-Series A Redeemable Convertible (2) 40.5 40.0 $ 5.1 40.5 40.0 $ 5.1 40.0 $0.03 - $0.29 September 6, 2026 Preferred-Series B Redeemable Convertible 41.8 41.7 33.7 41.8 41.7 33.7 41.7 0.81 September 6, 2026 Preferred-Series C Redeemable Convertible - Voting 35.4 35.4 50.9 35.4 35.4 50.9 35.4 1.44 September 6, 2026 Preferred-Series D Redeemable Convertible 19.6 19.3 99.9 19.6 19.3 99.9 19.3 5.17 September 6, 2026 Preferred-Series E Redeemable Convertible (3) 32.7 25.4 370.8 30.1 22.5 370.8 25.4 7.78 - 16.49 September 6, 2026 Total Preferred Stock 170.0 161.8 $ 560.4 167.4 158.9 $ 560.4 161.8 _______________ (1) All classes of stock have a par value of $0.0001 per share. (2) Shares issued for Series A-1 had a conversion price of $0.03. Shares issued for Series A-2 had a conversion price of $0.11. Shares issued for Series A-3 had a conversion price of $0.29. Collectively these shares are referred to as Series A. (3) Shares issued for Series E had a conversion price of $16.49. Shares issued for Series E-1 had a conversion price of $7.78. Collectively these shares are referred to as Series E. September 30, 2020 December 31, 2019 Shares Authorized Shares Issued and Outstanding Carrying Value Redemption Value Shares Authorized Shares Issued and Outstanding Carrying Value Redemption Value (in millions, except per share amounts) Preferred Stock (1) Preferred-Series A Redeemable Convertible 40.5 40.0 $ 5.1 $ 5.0 40.5 40.0 $ 5.1 $ 5.0 Preferred-Series B Redeemable Convertible 41.8 41.7 33.7 33.8 41.8 41.7 33.7 33.8 Preferred-Series C Redeemable Convertible - Voting 35.4 35.4 50.9 51.0 35.4 35.4 50.9 51.0 Preferred-Series D Redeemable Convertible 19.6 19.3 99.9 100.0 19.6 19.3 99.9 100.0 Preferred-Series E Redeemable Convertible 32.7 25.4 370.8 407.7 30.1 22.5 370.8 360.0 Total Preferred Stock 170.0 161.8 $ 560.4 $ 597.5 167.4 158.9 $ 560.4 $ 549.8 _______________ ____________ (1) All classes of stock have a par value of $0.0001 per share.

SHARE-BASED COMPENSATION

SHARE-BASED COMPENSATION	9 Months Ended
	Sep. 30, 2020
Share-based Payment Arrangement [Abstract]
SHARE-BASED COMPENSATION	SHARE-BASED COMPENSATIONWe maintain an equity incentive plan, the 2015 Equity Incentive Plan, or the 2015 Plan, for the issuance and grant of equity awards (restricted stock, restricted stock units, and incentive and nonqualified stock options) to our officers, directors, employees and certain consultants. As of September 30, 2020, the number of shares authorized under the 2015 Plan was 45.4 million authorized common shares. A summary of option activity for the nine months ended September 30, 2020 is as follows: September 30, 2020 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, 2020 12.3 $ 1.42 8.22 70.4 Granted 1.5 7.76 Exercised (1.5) 0.79 Forfeited, expired or canceled (0.7) 5.05 Outstanding and exercisable at September 30, 2020 11.6 2.20 7.82 124.2 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, 2020 2019 2020 2019 (dollars in millions) Share-based compensation expense: Loss and loss adjustment expenses $ — $ — $ 0.5 $ — Sales and marketing — — 1.0 — Other insurance expense — — 1.0 — Technology and development 0.2 — 5.4 — General and administrative 0.6 0.3 19.1 9.4 Total share-based compensation expense $ 0.8 $ 0.3 $ 27.0 $ 9.4 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 nine months ended September 30, 2020. As of September 30, 2020, there was $9.6 million of total unrecognized compensation cost related to share-based compensation. The remaining cost is expected to be recognized over a period of six years. The 2015 Plan permits the optionee to early exercise to obtain preferred tax treatment before the completion of the award’s requisite service or vesting period. If the employee terminates employment before the end of this period, the 2015 Plan requires us to repurchase the shares at the exercise price of the award. The repurchase feature is used to require the employee to remain through the requisite service or vesting period to receive the full economic benefit of the award. Given the repurchase feature functions as a forfeiture provision for nonvested shares, we record the exercise cost of nonvested shares as a deposit liability for those shares settling in cash. As the shares vest, the deposit liability is reduced and additional paid-in capital is increased. As of September 30, 2020 and December 31, 2019, the early exercise deposit liability was $1.4 million and $1.5 million, respectively, and is included in other liabilities on the condensed consolidated balance sheets.

RELATED PARTY LOANS

RELATED PARTY LOANS	9 Months Ended
	Sep. 30, 2020
Related Party Transactions [Abstract]
RELATED PARTY LOANS	RELATED PARTY LOANS As of September 30, 2020 and December 31, 2019, there were related party loans outstanding with several key employees of $3.4 million with a weighted-average interest rate of 2.87% and $4.3 million with a weighted-average interest rate of 2.80%, respectively. In May 2020, we settled a related party loan by accepting 0.3 million unvested shares and 0.1 million vested shares in exchange for the full repayment of the related $0.9 million related party loan and accrued interest. We recognized $0.7 million of treasury stock as a result. In October 2020, our Board of Directors approved the forgiveness of all outstanding principal and accrued but unpaid interest for each of the remaining related party loans. As the exercise price had effectively been reduced to zero, the forgiveness was accounted for as a modification of the stock options. An incremental share-based compensation cost of $3.4 million was determined based on the difference in the fair value of the options immediately prior to the modification and the modified fair value. Based on 0.5 million shares having vested as of the date of forgiveness, we recognized $0.3 million of share-based compensation expense in October 2020. The remaining $3.1 million share-based compensation expense will be recognized ratably over the remaining vesting period of 6 years.

COMMITMENTS AND CONTINGENCIES

COMMITMENTS AND CONTINGENCIES	9 Months Ended
	Sep. 30, 2020
Commitments and Contingencies Disclosure [Abstract]
COMMITMENTS AND CONTINGENCIES	COMMITMENTS AND CONTINGENCIES There are no litigation matters outstanding or pending that will have a material effect on our financial position or results of operations. 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, 2020
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, 2020 and 2019: Three Months Ended September 30, Nine Months Ended September 30, 2020 2019 2020 2019 (dollars in millions) Change in net unrealized gains on investment: Beginning balance $ 5.5 $ 0.7 $ 0.6 $ — Other comprehensive income before reclassifications 0.2 0.1 5.2 0.8 Realized gains on investments reclassified from AOCI to net income (0.1) — (0.2) — Net current period other comprehensive income 0.1 0.1 5.0 0.8 Ending balance $ 5.6 $ 0.8 $ 5.6 $ 0.8

LOSS PER SHARE

LOSS PER SHARE	9 Months Ended
	Sep. 30, 2020
Earnings Per Share [Abstract]
Earnings Per Share	LOSS PER SHARE EPS is presented for both basic EPS and diluted EPS. We compute basic EPS by dividing net income (loss) attributable to common stockholders by the weighted-average number of shares of common stock outstanding during the period. In addition to common shares outstanding, the computation of basic EPS includes instruments for which the holder has (or is deemed to have) the present rights as of the end of the reporting period to share in current period earnings (loss) with common stockholders (i.e., participating securities and common shares that are currently issuable for little or no cost to the holder). We also include in the denominator of our basic EPS computation the weighted-average number of shares of common stock that would be issued upon the full exercise of the warrants. These warrants have an insignificant exercise price of $0.0001 per share and are therefore considered outstanding common shares for computation of basic EPS. Diluted EPS includes all the components of basic EPS, plus the dilutive effect of common stock equivalents such as convertible securities and stock options, but excludes those common stock equivalents from the calculation of diluted EPS when the effect of inclusion, assessed individually, would be anti-dilutive. The calculation of income available to common stockholders and EPS is based on the underlying premise that all income after payment of dividends on preferred shares is available to and will be distributed to the common stockholders. The following table displays the computation of basic and diluted loss per share of common stock: Three Months Ended September 30, Nine Months Ended September 30, 2020 2019 2020 2019 (in millions, except per share amounts) Net loss $ (85.2) $ (100.2) $ (229.7) $ (197.2) Weighted-average common shares outstanding: basic and diluted 38.8 34.8 38.7 32.9 Loss per common share: basic and diluted $ (2.20) $ (2.88) $ (5.94) $ (5.99) 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 stockholders for the periods indicated because including them would have had an anti-dilutive effect: As of September 30, 2020 2019 (in millions) Options to purchase common stock 11.6 11.9 Redeemable convertible preferred stock (as converted to common stock) 161.8 158.9 Warrants to purchase redeemable convertible preferred stock (as converted to common stock) 0.6 0.6 174.0 171.4

GEOGRAPHICAL BREAKDOWN OF DIREC

GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM	9 Months Ended
	Sep. 30, 2020
Insurance [Abstract]
GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM	GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM Direct written premium (“DWP”) by state is as follows: Three Months Ended September 30, Nine Months Ended September 30, 2020 2019 2020 2019 Amount % of DWP Amount % of DWP Amount % of DWP Amount % of DWP State (dollars in millions) Texas $ 35.2 21.4 % $ 23.6 19.7 % $ 100.4 21.3 % $ 68.1 22.2 % Georgia 18.8 11.4 11.6 9.7 56.4 12.0 23.2 7.5 Kentucky 7.8 4.7 11.5 9.6 27.7 5.9 34.1 11.1 Pennsylvania 7.9 4.8 7.1 5.9 23.1 4.9 17.2 5.6 Arizona 7.9 4.8 7.5 6.3 22.9 4.9 18.8 6.1 Missouri 7.5 4.6 5.8 4.8 21.1 4.5 15.4 5.0 Louisiana 8.0 4.9 4.7 3.9 20.6 4.4 10.1 3.3 Utah 6.9 4.2 4.8 4.0 19.1 4.1 12.2 4.0 Ohio 5.6 3.4 6.4 5.4 16.6 3.5 17.2 5.6 Oregon 6.5 4.0 3.1 2.6 16.3 3.5 7.8 2.5 All others states 52.5 31.8 33.5 28.1 146.9 31.0 83.3 27.1 Total $ 164.6 100.0 % $ 119.6 100.0 % $ 471.1 100.0 % $ 307.4 100.0 %

SUBSEQUENT EVENTS

SUBSEQUENT EVENTS	9 Months Ended
	Sep. 30, 2020
Subsequent Events [Abstract]
SUBSEQUENT EVENTS	SUBSEQUENT EVENTS In October 2020, our Board of Directors approved the forgiveness of all outstanding principal and accrued but unpaid interest for each of the remaining related party loans. Refer to Note 10 for further discussion. In October 2020, our Board of Directors authorized additional shares bringing our total authorized shares to 1,000.0 million of Class A common stock, 269.0 million shares of Class B Common Stock and 100.0 million shares of Preferred Stock. All classes of stock have a par value of $0.0001 per share. The rights of the holders of Class A common stock and Class B common stock are identical, except with respect to voting, conversion and transfer rights. Each share of Class A common stock is entitled to one vote. Each share of Class B common stock is entitled to ten votes and is convertible at any time into one share of Class A common stock. All shares of our capital stock outstanding immediately prior to our IPO, were reclassified into shares of our Class B common stock. In October 2020,we completed our initial public offering of common stock, or IPO, which resulted in the issuance and sale of 24.2 million shares of common stock at the IPO price of $27.00, Concurrently, we issued and sold 18.5 million shares of our Class A common stock in private placements. We received net proceeds of $1.1 billion after deducting certain underwriting discounts and commissions and other offering costs of $53.4 million. In connection with the IPO, our outstanding convertible preferred stock converted into shares of Class B common stock and the 2.8 million liability classified warrants were exercised. Upon conversion of the convertible preferred stock, we reclassified the carrying value of the convertible preferred stock to common stock and additional paid-in capital. We adjusted the warrants to fair value immediately prior to their exercise which resulted in $38.7 million of interest expense recognized in October 2020. Upon exercise of the warrants, we reclassified the carrying value of the warrants from long-term debt and warrants to common stock and additional paid-in capital. In October 2020, our board of directors adopted and our stockholders approved the 2020 Equity Incentive Plan (the “2020 Plan”), which became effective as of October 28, 2020, our IPO date. The 2020 Plan provides for the issuance of incentive stock options, nonstatutory stock options, stock appreciation rights, restricted stock awards, restricted stock unit awards, performance awards, and other awards. The number of shares initially reserved for issuance under the 2020 Plan is 41.2 million shares, inclusive of available shares previously reserved for issuance under the 2015 Plan. In addition, the number of shares reserved for issuance under the 2020 Plan is subject to an annual increase on the first day of each calendar year beginning on January 1, 2021 and ending on and including January 1, 2030, in an amount equal to 4% of the total number of shares of capital stock outstanding on December 31st of the preceding year. Our board of directors may act prior to January 1st of a given year to provide that the increase for such year will be a lesser number of shares of Class A common stock. The aggregate maximum number of shares of Class A common stock that may be issued pursuant to the exercise of incentive stock options is 120.0 million shares. In October 2020, our board of directors adopted and our stockholders approved the 2020 Employee Stock Purchase Plan (the “ESPP”), which became effective immediately prior to our IPO date. The number of shares of Class A common stock initially reserved for issuance under the ESPP is limited to 5.0 million shares. In addition, the number of shares reserved for issuance under the ESPP is subject to an annual increase on the first day of each calendar year beginning on January 1, 2021 and ending on and including January 1, 2030, in an amount equal to the lesser of (i) 1% of the total number of shares of capital stock outstanding on December 31st of the preceding year and (ii) 7.5 million shares of Class A common stock. Our board of directors may act prior to January 1st of a given year to provide that the increase for such year will be a lesser number of shares of Class A common stock. In November 2020, we acquired a shell insurance company for $22.8 million, which included cash, cash equivalents, and accrued investment income of $14.4 million and insurance license indefinite-lived intangibles of $8.4 million. This acquisition will expand our ability to sell personal auto insurance in 48 states and the District of Columbia.

SIGNIFICANT ACCOUNTING POLICI_2

SIGNIFICANT ACCOUNTING POLICIES (Policies)	9 Months Ended
	Sep. 30, 2020
Accounting Policies [Abstract]
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.
Other Insurance Expense	Other Insurance Expense —Other insurance expense includes underwriting expenses; credit card and policy processing expenses; premium write-offs; insurance license expenses; and salaries, health benefits, bonuses, employee retirement plan related expenses, share-based compensation expenses, and overhead allocated based on headcount related to actuarial and certain data science activities. Other insurance expense also includes amortization of deferred acquisition costs like premium taxes and report costs related to the successful acquisition of a policy. Other insurance expense is expensed as incurred, except for costs related to deferred acquisition costs that are capitalized and subsequently amortized over the same period in which the related premiums are earned.
Deferred Offering Costs	Deferred Offering Costs—Deferred offering costs, which primarily consist of legal, accounting, and other third-party fees directly related to our initial public offering, or IPO, are capitalized as incurred. Upon consummation of the IPO, these deferred offering costs were offset against the IPO proceeds.
Recently Adopted Financial Accounting Standards/Upcoming Accounting Pronouncements	Recently Adopted Financial Accounting Standards —In August 2018, the FASB issued Accounting Standards Update No. 2018-15, Intangibles—Goodwill and Other—Internal-Use Software (Subtopic 350-40): Customer’s Accounting for Fees Paid in a Cloud Computing Arrangement , to help entities evaluate the accounting for fees paid by a customer in a cloud computing arrangement (hosting arrangement) by providing guidance for determining when the arrangement includes a software license. We early adopted ASU 2018-15 on January 1, 2020. The adoption of this standard did not have a material impact on our condensed consolidated financial statements or notes to the condensed consolidated financial statements. In December 2019, the FASB issued ASU 2019-12, Income Taxes (Topic 740)—Simplifying the Accounting for Income Taxes. The amendments in the update simplify the accounting for income taxes by, among other things, removing the exception to the incremental approach for intraperiod tax allocation when there is a loss from continuing operations and income or a gain from other items like comprehensive income, and recognizing franchise tax that is partially based on income as an income-based tax. We early adopted ASU 2019-12 on January 1, 2020. The adoption of this standard did not have a material impact on our condensed consolidated financial statements or notes to the condensed consolidated financial statements. 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 February 2016, the FASB issued ASU 2016-02, Leases (Topic 842) . The main provision of ASU 2016-02 requires the recognition of lease assets and lease liabilities by lessees for those leases classified as operating leases under previous GAAP. The effective date of ASU 2016-02 is for annual reporting periods beginning after December 15, 2021, and interim reporting periods beginning after December 15, 2022. We are currently evaluating the impact of this ASU. 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 this ASU.

INVESTMENTS (Tables)

INVESTMENTS (Tables)	9 Months Ended
	Sep. 30, 2020
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, 2020 and December 31, 2019 are as follows: September 30, 2020 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Bonds and short-term investments: U.S. Treasury securities and agencies $ 5.1 $ 0.1 $ — $ 5.2 Municipal securities 20.2 0.8 — 21.0 Corporate debt securities 95.8 3.1 — 98.9 Residential mortgage-backed securities 11.1 0.1 (0.1) 11.1 Commercial mortgage backed securities 57.9 1.2 (0.1) 59.0 Other debt obligations 28.8 0.5 — 29.3 Total $ 218.9 $ 5.8 $ (0.2) $ 224.5 December 31, 2019 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Fair Value (dollars in millions) Bonds and short-term investments: U.S. Treasury securities and agencies $ 12.7 $ 0.1 $ — $ 12.8 Municipal securities 10.2 0.1 — 10.3 Corporate debt securities 38.8 0.4 (0.1) 39.1 Residential mortgage-backed securities 3.3 — — 3.3 Commercial mortgage backed securities 31.5 0.1 (0.1) 31.5 Other debt obligations 25.7 0.1 — 25.8 Total $ 122.2 $ 0.8 $ (0.2) $ 122.8 The amortized cost and fair value of short-term investments and fixed maturity securities by contractual maturity at September 30, 2020 and December 31, 2019 are as follows: September 30, 2020 December 31, 2019 Amortized Cost Fair Value Amortized Cost Fair Value (dollars in millions) Due in one year or less $ 13.7 $ 13.9 $ 14.3 $ 14.3 Due after one year through five years 149.9 154.6 81.6 82.1 Due five years through 10 years 18.1 18.4 4.9 4.9 Due after 10 years 37.2 37.6 21.4 21.5 Total $ 218.9 $ 224.5 $ 122.2 $ 122.8
Schedule of unrealized losses	The following tables reflect the gross unrealized losses, fair value on bonds, aggregated by investment category and length of time that individual securities have been in a continuous unrealized loss position at September 30, 2020 and December 31, 2019: September 30, 2020 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Bonds: Municipal securities $ 2.7 $ — $ — $ — $ 2.7 $ — Corporate debt securities 7.6 — — — 7.6 — Residential mortgage-backed securities 6.8 (0.1) — — 6.8 (0.1) Commercial mortgage-backed securities 3.6 (0.1) — — 3.6 (0.1) Total bonds $ 20.7 $ (0.2) $ — $ — $ 20.7 $ (0.2) December 31, 2019 Less than 12 Months 12 Months or More Total Fair Value Unrealized Fair Value Unrealized Fair Value Unrealized (dollars in millions) Bonds: Municipal securities $ 5.5 $ — $ — $ — $ 5.5 $ — Corporate debt securities 12.8 (0.1) — — 12.8 (0.1) Residential mortgage-backed securities 1.9 — — — 1.9 — Commercial mortgage-backed securities 24.5 (0.1) — — 24.5 (0.1) Other debt obligations 7.4 — — — 7.4 — Total bonds $ 52.1 $ (0.2) $ — $ — $ 52.1 $ (0.2)
Schedule of net investment income	The following table sets forth the components of net investment income for the three months and nine months ended September 30, 2020 and 2019: Three Months Ended September 30, Nine Months Ended September 30, 2020 2019 2020 2019 (dollars in millions) Interest on bonds $ 1.1 $ (0.8) $ 3.2 $ 1.0 Interest on deposits and cash equivalents 0.1 2.0 1.4 2.0 Total 1.2 1.2 4.6 3.0 Investment expense (0.1) (0.1) (0.3) (0.2) Net investment income $ 1.1 $ 1.1 $ 4.3 $ 2.8
Schedule of credit ratings	The following tables summarize the credit ratings of investments at September 30, 2020 and December 31, 2019: September 30, 2020 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 113.3 $ 115.5 51.4 % AA+, AA, AA-, A-1 19.4 20.1 9.0 A+, A, A- 65.0 66.9 29.8 BBB+, BBB, BBB- 21.2 22.0 9.8 Total $ 218.9 $ 224.5 100.0 % December 31, 2019 Amortized Cost Fair Value % of Total S&P Global rating or equivalent (dollars in millions) AAA $ 78.8 $ 79.0 64.3 % AA+, AA, AA-, A-1 8.7 8.8 7.2 A+, A, A- 26.6 26.9 21.9 BBB+, BBB, BBB- 8.1 8.1 6.6 Total $ 122.2 $ 122.8 100.0 %

FAIR VALUE OF FINANCIAL INSTR_2

FAIR VALUE OF FINANCIAL INSTRUMENTS (Tables)	9 Months Ended
	Sep. 30, 2020
Fair Value Disclosures [Abstract]
Schedule of fair value	The following tables provide information about our financial assets and liabilities measured and reported at fair value: September 30, 2020 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities $ 2.7 $ 219.3 $ — $ 222.0 Short-term investments 2.5 — — 2.5 Cash equivalents 167.7 — — 167.7 Total Assets at fair value $ 172.9 $ 219.3 $ — $ 392.2 Liabilities Warrant liability $ — $ — $ 36.3 $ 36.3 Total Liabilities at fair value $ — $ — $ 36.3 $ 36.3 December 31, 2019 Level 1 Level 2 Level 3 Total (dollars in millions) Assets Fixed maturities $ 9.8 $ 109.5 $ — $ 119.3 Short-term investments 3.0 0.5 — 3.5 Cash equivalents 316.6 — — 316.6 Total Assets at fair value $ 329.4 $ 110.0 $ — $ 439.4 Liabilities Warrant liability $ — $ — $ 20.3 $ 20.3 Total Liabilities at fair value $ — $ — $ 20.3 $ 20.3
Schedule of carrying amounts and fair values of financial instruments	As of September 30, 2020 and December 31, 2019 the carrying amounts and fair values of these financial instruments were as follows: Carrying amount as of September 30, 2020 Estimated Fair Value as of September 30, 2020 Carrying amount as of December 31, 2019 Estimated Fair Value as of December 31, 2019 (dollars in millions) Long-term debt $ 184.4 $ 207.7 $ 172.7 $ 200.8

LOSS AND LOSS ADJUSTMENT EXPE_2

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Tables)	9 Months Ended
	Sep. 30, 2020
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: Nine Months Ended September 30, 2020 2019 (dollars in millions) Gross loss and LAE reserves, January 1 $ 140.7 $ 33.3 Reinsurance recoverable on unpaid losses (18.9) (11.4) Net loss and LAE reserves, January 1 121.8 21.9 Net incurred loss and LAE related to: Current year 282.0 204.4 Prior years 21.3 6.1 Total incurred 303.3 210.5 Net paid loss and LAE related to: Current year 165.8 125.2 Prior years 100.4 23.3 Total paid 266.2 148.5 Net loss and LAE reserves, September 30 158.9 83.9 Plus reinsurance recoverable on unpaid losses 66.4 26.5 Gross loss and LAE reserves, September 30 $ 225.3 $ 110.4

LONG-TERM DEBT (Tables)

LONG-TERM DEBT (Tables)	9 Months Ended
	Sep. 30, 2020
Debt Disclosure [Abstract]
Schedule of long term debt	The following summarizes the carrying value of long-term debt and warrants as of September 30, 2020 and December 31, 2019: September 30, 2020 December 31, 2019 (dollars in millions) Term Loan A $ 99.8 $ 99.5 Term Loan B 100.0 100.0 Warrants 36.3 20.3 Total 236.1 219.8 Accrued interest payable 7.7 0.9 Unamortized discount and debt issuance costs (23.8) (28.5) Total $ 220.0 $ 192.2

CAPITAL STOCK (Tables)

CAPITAL STOCK (Tables)	9 Months Ended
	Sep. 30, 2020
Equity [Abstract]
Schedule of stock	The following table displays our capital stock as of September 30, 2020 and December 31, 2019: September 30, 2020 December 31, 2019 Shares Authorized Shares Issued and Outstanding Carrying Value Shares Authorized Shares Issued and Outstanding Carrying Value Common Stock Issuable Upon Conversion Conversion Price Per Share Redeemable on or After (in millions, except per share amounts) Common Stock-Voting (1) 269.0 42.5 $ — 266.0 44.4 $ — — Preferred Stock (1) Preferred-Series A Redeemable Convertible (2) 40.5 40.0 $ 5.1 40.5 40.0 $ 5.1 40.0 $0.03 - $0.29 September 6, 2026 Preferred-Series B Redeemable Convertible 41.8 41.7 33.7 41.8 41.7 33.7 41.7 0.81 September 6, 2026 Preferred-Series C Redeemable Convertible - Voting 35.4 35.4 50.9 35.4 35.4 50.9 35.4 1.44 September 6, 2026 Preferred-Series D Redeemable Convertible 19.6 19.3 99.9 19.6 19.3 99.9 19.3 5.17 September 6, 2026 Preferred-Series E Redeemable Convertible (3) 32.7 25.4 370.8 30.1 22.5 370.8 25.4 7.78 - 16.49 September 6, 2026 Total Preferred Stock 170.0 161.8 $ 560.4 167.4 158.9 $ 560.4 161.8 _______________ (1) All classes of stock have a par value of $0.0001 per share. (2) Shares issued for Series A-1 had a conversion price of $0.03. Shares issued for Series A-2 had a conversion price of $0.11. Shares issued for Series A-3 had a conversion price of $0.29. Collectively these shares are referred to as Series A. (3) Shares issued for Series E had a conversion price of $16.49. Shares issued for Series E-1 had a conversion price of $7.78. Collectively these shares are referred to as Series E.
Schedule of temporary equity	The following table displays our capital stock as of September 30, 2020 and December 31, 2019: September 30, 2020 December 31, 2019 Shares Authorized Shares Issued and Outstanding Carrying Value Shares Authorized Shares Issued and Outstanding Carrying Value Common Stock Issuable Upon Conversion Conversion Price Per Share Redeemable on or After (in millions, except per share amounts) Common Stock-Voting (1) 269.0 42.5 $ — 266.0 44.4 $ — — Preferred Stock (1) Preferred-Series A Redeemable Convertible (2) 40.5 40.0 $ 5.1 40.5 40.0 $ 5.1 40.0 $0.03 - $0.29 September 6, 2026 Preferred-Series B Redeemable Convertible 41.8 41.7 33.7 41.8 41.7 33.7 41.7 0.81 September 6, 2026 Preferred-Series C Redeemable Convertible - Voting 35.4 35.4 50.9 35.4 35.4 50.9 35.4 1.44 September 6, 2026 Preferred-Series D Redeemable Convertible 19.6 19.3 99.9 19.6 19.3 99.9 19.3 5.17 September 6, 2026 Preferred-Series E Redeemable Convertible (3) 32.7 25.4 370.8 30.1 22.5 370.8 25.4 7.78 - 16.49 September 6, 2026 Total Preferred Stock 170.0 161.8 $ 560.4 167.4 158.9 $ 560.4 161.8 _______________ (1) All classes of stock have a par value of $0.0001 per share. (2) Shares issued for Series A-1 had a conversion price of $0.03. Shares issued for Series A-2 had a conversion price of $0.11. Shares issued for Series A-3 had a conversion price of $0.29. Collectively these shares are referred to as Series A. (3) Shares issued for Series E had a conversion price of $16.49. Shares issued for Series E-1 had a conversion price of $7.78. Collectively these shares are referred to as Series E. September 30, 2020 December 31, 2019 Shares Authorized Shares Issued and Outstanding Carrying Value Redemption Value Shares Authorized Shares Issued and Outstanding Carrying Value Redemption Value (in millions, except per share amounts) Preferred Stock (1) Preferred-Series A Redeemable Convertible 40.5 40.0 $ 5.1 $ 5.0 40.5 40.0 $ 5.1 $ 5.0 Preferred-Series B Redeemable Convertible 41.8 41.7 33.7 33.8 41.8 41.7 33.7 33.8 Preferred-Series C Redeemable Convertible - Voting 35.4 35.4 50.9 51.0 35.4 35.4 50.9 51.0 Preferred-Series D Redeemable Convertible 19.6 19.3 99.9 100.0 19.6 19.3 99.9 100.0 Preferred-Series E Redeemable Convertible 32.7 25.4 370.8 407.7 30.1 22.5 370.8 360.0 Total Preferred Stock 170.0 161.8 $ 560.4 $ 597.5 167.4 158.9 $ 560.4 $ 549.8 _______________ ____________ (1) All classes of stock have a par value of $0.0001 per share.

SHARE-BASED COMPENSATION (Table

SHARE-BASED COMPENSATION (Tables)	9 Months Ended
	Sep. 30, 2020
Share-based Payment Arrangement [Abstract]
Summary of option activity	A summary of option activity for the nine months ended September 30, 2020 is as follows: September 30, 2020 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, 2020 12.3 $ 1.42 8.22 70.4 Granted 1.5 7.76 Exercised (1.5) 0.79 Forfeited, expired or canceled (0.7) 5.05 Outstanding and exercisable at September 30, 2020 11.6 2.20 7.82 124.2
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, 2020 2019 2020 2019 (dollars in millions) Share-based compensation expense: Loss and loss adjustment expenses $ — $ — $ 0.5 $ — Sales and marketing — — 1.0 — Other insurance expense — — 1.0 — Technology and development 0.2 — 5.4 — General and administrative 0.6 0.3 19.1 9.4 Total share-based compensation expense $ 0.8 $ 0.3 $ 27.0 $ 9.4

OTHER COMPREHENSIVE INCOME AN_2

OTHER COMPREHENSIVE INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME (Tables)	9 Months Ended
	Sep. 30, 2020
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, 2020 and 2019: Three Months Ended September 30, Nine Months Ended September 30, 2020 2019 2020 2019 (dollars in millions) Change in net unrealized gains on investment: Beginning balance $ 5.5 $ 0.7 $ 0.6 $ — Other comprehensive income before reclassifications 0.2 0.1 5.2 0.8 Realized gains on investments reclassified from AOCI to net income (0.1) — (0.2) — Net current period other comprehensive income 0.1 0.1 5.0 0.8 Ending balance $ 5.6 $ 0.8 $ 5.6 $ 0.8

LOSS PER SHARE (Tables)

LOSS PER SHARE (Tables)	9 Months Ended
	Sep. 30, 2020
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: Three Months Ended September 30, Nine Months Ended September 30, 2020 2019 2020 2019 (in millions, except per share amounts) Net loss $ (85.2) $ (100.2) $ (229.7) $ (197.2) Weighted-average common shares outstanding: basic and diluted 38.8 34.8 38.7 32.9 Loss per common share: basic and diluted $ (2.20) $ (2.88) $ (5.94) $ (5.99)
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 stockholders for the periods indicated because including them would have had an anti-dilutive effect: As of September 30, 2020 2019 (in millions) Options to purchase common stock 11.6 11.9 Redeemable convertible preferred stock (as converted to common stock) 161.8 158.9 Warrants to purchase redeemable convertible preferred stock (as converted to common stock) 0.6 0.6 174.0 171.4

GEOGRAPHICAL BREAKDOWN OF DIR_2

GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM (Tables)	9 Months Ended
	Sep. 30, 2020
Insurance [Abstract]
Schedule of direct premiums written	Direct written premium (“DWP”) by state is as follows: Three Months Ended September 30, Nine Months Ended September 30, 2020 2019 2020 2019 Amount % of DWP Amount % of DWP Amount % of DWP Amount % of DWP State (dollars in millions) Texas $ 35.2 21.4 % $ 23.6 19.7 % $ 100.4 21.3 % $ 68.1 22.2 % Georgia 18.8 11.4 11.6 9.7 56.4 12.0 23.2 7.5 Kentucky 7.8 4.7 11.5 9.6 27.7 5.9 34.1 11.1 Pennsylvania 7.9 4.8 7.1 5.9 23.1 4.9 17.2 5.6 Arizona 7.9 4.8 7.5 6.3 22.9 4.9 18.8 6.1 Missouri 7.5 4.6 5.8 4.8 21.1 4.5 15.4 5.0 Louisiana 8.0 4.9 4.7 3.9 20.6 4.4 10.1 3.3 Utah 6.9 4.2 4.8 4.0 19.1 4.1 12.2 4.0 Ohio 5.6 3.4 6.4 5.4 16.6 3.5 17.2 5.6 Oregon 6.5 4.0 3.1 2.6 16.3 3.5 7.8 2.5 All others states 52.5 31.8 33.5 28.1 146.9 31.0 83.3 27.1 Total $ 164.6 100.0 % $ 119.6 100.0 % $ 471.1 100.0 % $ 307.4 100.0 %

NATURE OF BUSINESS (Details)

NATURE OF BUSINESS (Details)	Sep. 30, 2020state
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Percentage of customers acquired through mobile applications	75.00%
Number of states auto policies written	30
Number of states licensed to write auto policies	6
Number of states renter's insurance written	9

SIGNIFICANT ACCOUNTING POLICI_3

SIGNIFICANT ACCOUNTING POLICIES (Details) $ in Millions	Sep. 30, 2020USD ($)
Accounting Policies [Abstract]
Percentage of direct earned premiums ceded	70.00%
Deferred offering costs	$ 0.7

INVESTMENTS - Amortized Cost an

INVESTMENTS - Amortized Cost and Fair Value (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Debt Securities, Available-for-sale [Line Items]
Total	$ 218.9	$ 122.2
Gross Unrealized Gains	5.8	0.8
Gross Unrealized Losses	(0.2)	(0.2)
Fair Value	224.5	122.8
U.S. Treasury securities and agencies
Debt Securities, Available-for-sale [Line Items]
Total	5.1	12.7
Gross Unrealized Gains	0.1	0.1
Gross Unrealized Losses	0	0
Fair Value	5.2	12.8
Municipal securities
Debt Securities, Available-for-sale [Line Items]
Total	20.2	10.2
Gross Unrealized Gains	0.8	0.1
Gross Unrealized Losses	0	0
Fair Value	21	10.3
Corporate debt securities
Debt Securities, Available-for-sale [Line Items]
Total	95.8	38.8
Gross Unrealized Gains	3.1	0.4
Gross Unrealized Losses	0	(0.1)
Fair Value	98.9	39.1
Residential mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Total	11.1	3.3
Gross Unrealized Gains	0.1	0
Gross Unrealized Losses	(0.1)	0
Fair Value	11.1	3.3
Commercial mortgage backed securities
Debt Securities, Available-for-sale [Line Items]
Total	57.9	31.5
Gross Unrealized Gains	1.2	0.1
Gross Unrealized Losses	(0.1)	(0.1)
Fair Value	59	31.5
Other debt obligations
Debt Securities, Available-for-sale [Line Items]
Total	28.8	25.7
Gross Unrealized Gains	0.5	0.1
Gross Unrealized Losses	0	0
Fair Value	$ 29.3	$ 25.8

INVESTMENTS - Unrealized Losses

INVESTMENTS - Unrealized Losses (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	$ 20.7	$ 52.1
Less than 12 Months, Unrealized Loss	(0.2)	(0.2)
12 Months or More, Fair Value	0	0
12 Months or More, Unrealized Loss	0	0
Total, Fair Value	20.7	52.1
Total, Unrealized Loss	(0.2)	(0.2)
Municipal securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	2.7	5.5
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	2.7	5.5
Total, Unrealized Loss	0	0
Corporate debt securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	7.6	12.8
Less than 12 Months, Unrealized Loss	0	(0.1)
12 Months or More, Fair Value	0	0
12 Months or More, Unrealized Loss	0	0
Total, Fair Value	7.6	12.8
Total, Unrealized Loss	0	(0.1)
Residential mortgage-backed securities
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value	6.8	1.9
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	6.8	1.9
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	3.6	24.5
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	3.6	24.5
Total, Unrealized Loss	$ (0.1)	(0.1)
Other debt obligations
Debt Securities, Available-for-sale, Unrealized Loss Position [Line Items]
Less than 12 Months, Fair Value		7.4
Less than 12 Months, Unrealized Loss		0
12 Months or More, Fair Value		0
12 Months or More, Unrealized Loss		0
Total, Fair Value		7.4
Total, Unrealized Loss		$ 0

INVESTMENTS - Contractual Matur

INVESTMENTS - Contractual Maturity (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Amortized Cost
Due in one year or less	$ 13.7	$ 14.3
Due after one year through five years	149.9	81.6
Due five years through 10 years	18.1	4.9
Due after 10 years	37.2	21.4
Total	218.9	122.2
Fair Value
Due in one year or less	13.9	14.3
Due after one year through five years	154.6	82.1
Due five years through 10 years	18.4	4.9
Due after 10 years	37.6	21.5
Total investments	$ 224.5	$ 122.8

INVESTMENTS - Narrative (Detail

INVESTMENTS - Narrative (Details) - USD ($)	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Investments, Debt and Equity Securities [Abstract]
Net realized gains	$ 100,000	$ 0	$ 200,000	$ 0

INVESTMENTS - Net Investment In

INVESTMENTS - Net Investment Income (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Net Investment Income [Line Items]
Total	$ 1.2	$ 1.2	$ 4.6	$ 3
Investment expense	(0.1)	(0.1)	(0.3)	(0.2)
Net investment income	1.1	1.1	4.3	2.8
Bonds
Net Investment Income [Line Items]
Total	1.1	(0.8)	3.2	1
Deposits and cash equivalents
Net Investment Income [Line Items]
Total	$ 0.1	$ 2	$ 1.4	$ 2

INVESTMENTS - Credit Ratings (D

INVESTMENTS - Credit Ratings (Details) - USD ($) $ in Millions	9 Months Ended	12 Months Ended
	Sep. 30, 2020	Dec. 31, 2019
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 218.9	$ 122.2
Fair Value	$ 224.5	$ 122.8
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	$ 113.3	$ 78.8
Fair Value	$ 115.5	$ 79
AAA | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	51.40%	64.30%
AA+, AA, AA-, A-1
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 19.4	$ 8.7
Fair Value	$ 20.1	$ 8.8
AA+, AA, AA-, A-1 | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	9.00%	7.20%
A+, A, A-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 65	$ 26.6
Fair Value	$ 66.9	$ 26.9
A+, A, A- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	29.80%	21.90%
BBB+, BBB, BBB-
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 21.2	$ 8.1
Fair Value	$ 22	$ 8.1
BBB+, BBB, BBB- | AFS securities | Credit rating
Debt Securities, Available-for-sale [Line Items]
Concentration percentage	9.80%	6.60%

FAIR VALUE OF FINANCIAL INSTR_3

FAIR VALUE OF FINANCIAL INSTRUMENTS - Balance Sheet Grouping (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Assets
AFS securities	$ 224.5	$ 122.8
Cash equivalents	167.7	316.6
Total Assets at fair value	392.2	439.4
Liabilities
Warrant liability	36.3	20.3
Total Liabilities at fair value	36.3	20.3
Fixed maturities
Assets
AFS securities	222	119.3
Short-term investments
Assets
AFS securities	2.5	3.5
Level 1
Assets
Cash equivalents	167.7	316.6
Total Assets at fair value	172.9	329.4
Liabilities
Warrant liability	0	0
Total Liabilities at fair value	0	0
Level 1 | Fixed maturities
Assets
AFS securities	2.7	9.8
Level 1 | Short-term investments
Assets
AFS securities	2.5	3
Level 2
Assets
Cash equivalents	0	0
Total Assets at fair value	219.3	110
Liabilities
Warrant liability	0	0
Total Liabilities at fair value	0	0
Level 2 | Fixed maturities
Assets
AFS securities	219.3	109.5
Level 2 | Short-term investments
Assets
AFS securities	0	0.5
Level 3
Assets
Cash equivalents	0	0
Total Assets at fair value	0	0
Liabilities
Warrant liability	36.3	20.3
Total Liabilities at fair value	36.3	20.3
Level 3 | 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 - Narrative (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	3 Months Ended	9 Months Ended
	Sep. 30, 2020	Sep. 30, 2020	Sep. 30, 2019
Fair Value Disclosures [Abstract]
Warrant fair value (in dollars per share)	$ 12.9699	$ 12.9699
Warrants outstanding (in shares)	2.8	2.8
Adjustment to fair value of warrants	$ 13.7	$ 16	$ 0

FAIR VALUE OF FINANCIAL INSTR_5

FAIR VALUE OF FINANCIAL INSTRUMENTS - Long Term Debt (Details) - Level 2 - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Carrying amount
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 184.4	$ 172.7
Estimated Fair Value
Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]
Long-term debt	$ 207.7	$ 200.8

LOSS AND LOSS ADJUSTMENT EXPE_3

LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Gross loss and LAE reserves, January 1			$ 140.7	$ 33.3
Reinsurance recoverable on unpaid losses			(18.9)	(11.4)
Net loss and LAE reserves, January 1			121.8	21.9
Net incurred loss and LAE related to:
Current year			282	204.4
Prior years			21.3	6.1
Total incurred	$ 76.1	$ 100.9	303.3	210.5
Net paid loss and LAE related to:
Current year			165.8	125.2
Prior years			100.4	23.3
Total paid			266.2	148.5
Net loss and LAE reserves, September 30	158.9	83.9	158.9	83.9
Plus reinsurance recoverable on unpaid losses	66.4	26.5	66.4	26.5
Gross loss and LAE reserves, September 30	$ 225.3	$ 110.4	$ 225.3	$ 110.4

LONG-TERM DEBT - Schedule Of De

LONG-TERM DEBT - Schedule Of Debt (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Debt Instrument [Line Items]
Total	$ 236.1	$ 219.8
Accrued interest payable	7.7	0.9
Unamortized discount and debt issuance costs	(23.8)	(28.5)
Total	220	192.2
Term loan | Term Loan A
Debt Instrument [Line Items]
Total	99.8	99.5
Term loan | Term Loan B
Debt Instrument [Line Items]
Total	100	100
Warrants
Debt Instrument [Line Items]
Total	$ 36.3	$ 20.3

LONG-TERM DEBT - Narrative (Det

LONG-TERM DEBT - Narrative (Details) - USD ($)	1 Months Ended	9 Months Ended
	Sep. 30, 2020	Sep. 30, 2020	Dec. 31, 2019
Debt Instrument [Line Items]
Letters of credit outstanding	$ 0	$ 0
Accrued interest payable	7,700,000	7,700,000	$ 900,000
Term loan | Amended Term Loan A | Wells Fargo, Barclays, Morgan Stanley and Deutsche Bank
Debt Instrument [Line Items]
Debt amount	$ 13,500,000	13,500,000
Term loan | Amended Term Loan B | Wells Fargo, Barclays, Morgan Stanley and Deutsche Bank
Debt Instrument [Line Items]
Increase in interest rate	3.50%
Accrued interest payable	$ 7,600,000	$ 7,600,000	$ 800,000
Term loan | Amended Term Loan B | LIBOR | Wells Fargo, Barclays, Morgan Stanley and Deutsche Bank
Debt Instrument [Line Items]
Variable rate percentage		10.50%
Line of Credit | Amended Term Loan A | Revolving Loan | Wells Fargo, Barclays, Morgan Stanley and Deutsche Bank
Debt Instrument [Line Items]
Maximum borrowing capacity	$ 100,000,000	$ 100,000,000
Unused fee percentage	0.50%
Line of Credit | Amended Term Loan A | Letter of Credit | Wells Fargo, Barclays, Morgan Stanley and Deutsche Bank
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	9 Months Ended
	Sep. 30, 2020	Sep. 30, 2020
Income Tax Disclosure [Abstract]
Effective income tax rate	0.00%	0.00%
Federal income tax rate		21.00%

CAPITAL STOCK (Details)

CAPITAL STOCK (Details) - $ / shares shares in Millions	Sep. 30, 2020	Dec. 31, 2019
Temporary Equity [Line Items]
Shares authorized (in shares)	170	167.4
Par value (in dollars per share)	$ 0.0001	$ 0.0001
Common stock, shares authorized (in shares)	269	266
Common stock, par value (in dollars per share)	$ 0.0001	$ 0.0001
Series A Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	40.5	40.5
Series B Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	41.8	41.8
Series C Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	35.4	35.4
Series D Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	19.6	19.6
Series E Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	32.7	30.1

CAPITAL STOCK - Schedule of Equ

CAPITAL STOCK - Schedule of Equity (Details) - USD ($) $ / shares in Units, shares in Millions, $ in Millions	Sep. 30, 2020	Jun. 30, 2020	Dec. 31, 2019	Sep. 30, 2019	Jun. 30, 2019	Dec. 31, 2018
Equity [Abstract]
Common stock, shares authorized (in shares)	269		266
Common stock, shares issued (in shares)	42.5		44.4
Common stock, shares outstanding (in shares)	42.5		44.4
Carry value	$ 0		$ 0
Temporary Equity [Line Items]
Shares authorized (in shares)	170		167.4
Shares issued (in shares)	161.8		158.9
Shares outstanding (in shares)	161.8	161.8	158.9	158.9	136.4	136.4
Carrying value	$ 560.4	$ 560.4	$ 560.4	$ 560.7	$ 189.6	$ 189.6
Common stock issuable upon conversion (in shares)	161.8
Par value (in dollars per share)	$ 0.0001		$ 0.0001
Redemption Value	$ 597.5		$ 549.8
Series A Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	40.5		40.5
Shares issued (in shares)	40		40
Shares outstanding (in shares)	40		40
Carrying value	$ 5.1		$ 5.1
Common stock issuable upon conversion (in shares)	40
Redemption Value	$ 5		$ 5
Series A Preferred Stock | Minimum
Temporary Equity [Line Items]
Conversion price per share (in dollars per share)	$ 0.03
Series A Preferred Stock | Maximum
Temporary Equity [Line Items]
Conversion price per share (in dollars per share)	0.29
Series A-1 Preferred Stock
Temporary Equity [Line Items]
Conversion price per share (in dollars per share)	0.03		$ 0.03
Series A-2 Preferred Stock
Temporary Equity [Line Items]
Conversion price per share (in dollars per share)	0.11		0.11
Series A-3 Preferred Stock
Temporary Equity [Line Items]
Conversion price per share (in dollars per share)	$ 0.29		$ 0.29
Series B Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	41.8		41.8
Shares issued (in shares)	41.7		41.7
Shares outstanding (in shares)	41.7		41.7
Carrying value	$ 33.7		$ 33.7
Common stock issuable upon conversion (in shares)	41.7
Conversion price per share (in dollars per share)	$ 0.81
Redemption Value	$ 33.8		$ 33.8
Series C Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	35.4		35.4
Shares issued (in shares)	35.4		35.4
Shares outstanding (in shares)	35.4		35.4
Carrying value	$ 50.9		$ 50.9
Common stock issuable upon conversion (in shares)	35.4
Conversion price per share (in dollars per share)	$ 1.44
Redemption Value	$ 51		$ 51
Series D Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	19.6		19.6
Shares issued (in shares)	19.3		19.3
Shares outstanding (in shares)	19.3		19.3
Carrying value	$ 99.9		$ 99.9
Common stock issuable upon conversion (in shares)	19.3
Conversion price per share (in dollars per share)	$ 5.17
Redemption Value	$ 100		$ 100
Series E Preferred Stock
Temporary Equity [Line Items]
Shares authorized (in shares)	32.7		30.1
Shares issued (in shares)	25.4		22.5
Shares outstanding (in shares)	25.4		22.5
Carrying value	$ 370.8		$ 370.8
Common stock issuable upon conversion (in shares)	25.4
Conversion price per share (in dollars per share)	$ 16.49		$ 16.49
Redemption Value	$ 407.7		$ 360
Series E Preferred Stock | Minimum
Temporary Equity [Line Items]
Conversion price per share (in dollars per share)	$ 7.78
Series E Preferred Stock | Maximum
Temporary Equity [Line Items]
Conversion price per share (in dollars per share)	16.49
Series E-1 Preferred Stock
Temporary Equity [Line Items]
Conversion price per share (in dollars per share)	$ 7.78		$ 7.78

SHARE-BASED COMPENSATION - Narr

SHARE-BASED COMPENSATION - Narrative (Details) - USD ($) shares in Millions, $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019	Dec. 31, 2019
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense	$ 0.8	$ 0.3	$ 27	$ 9.4
Unrecognized compensation cost	9.6		$ 9.6
Unrecognized compensation cost, period of recognition			6 years
Tender offer | Common stock
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Total share-based compensation expense			$ 25.1
Other liabilities
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Exercise deposit liability	$ 1.4		$ 1.4		$ 1.5
2015 Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares authorized (in shares)	45.4		45.4

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, 2020USD ($)$ / sharesshares	Dec. 31, 2019USD ($)$ / sharesshares
Number of Shares
Outstanding, beginning balance (in shares) | shares	12.3
Granted (in shares) | shares	1.5
Exercised (in shares) | shares	(1.5)
Forfeited, expired or canceled (in shares) | shares	(0.7)
Outstanding, ending balance (in shares) | shares	11.6	12.3
Weighted-Average Exercise Price
Outstanding, beginning balance, weighted-average exercise price (in dollars per share) | $ / shares	$ 1.42
Granted, weighted-average exercise price (in dollars per share) | $ / shares	7.76
Exercised, weighted-average exercise price (in dollars per share) | $ / shares	0.79
Forfeited, expired and canceled, weighted-average exercise price (in dollars per share) | $ / shares	5.05
Outstanding, ending balance, weighted-average exercise price (in dollars per share) | $ / shares	$ 2.20	$ 1.42
Outstanding, weighted-average remaining contractual term (in years)	7 years 9 months 25 days	8 years 2 months 19 days
Outstanding, aggregate intrinsic value | $	$ 124.2	$ 70.4
Exercisable, balance (in shares) | shares	11.6	12.3
Exercisable, weighted-average exercise price (in dollars per share) | $ / shares	$ 2.20	$ 1.42
Exercisable, weighted-average remaining contractual term (in years)	7 years 9 months 25 days	8 years 2 months 19 days
Exercisable, aggregate intrinsic value | $	$ 124.2	$ 70.4

SHARE-BASED COMPENSATION - Shar

SHARE-BASED COMPENSATION - Share-based Compensation Expense (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 0.8	$ 0.3	$ 27	$ 9.4
Loss and loss adjustment expenses
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0	0	0.5	0
Sales and marketing
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0	0	1	0
Other insurance expense
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0	0	1	0
Technology and development
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	0.2	0	5.4	0
General and administrative
Share-based Payment Arrangement, Expensed and Capitalized, Amount [Line Items]
Total share-based compensation expense	$ 0.6	$ 0.3	$ 19.1	$ 9.4

RELATED PARTY LOANS (Details)

RELATED PARTY LOANS (Details) - USD ($) shares in Millions, $ in Millions	1 Months Ended		3 Months Ended		9 Months Ended		12 Months Ended
	Oct. 31, 2020	May 31, 2020	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019	Dec. 31, 2019
Related Party Transaction [Line Items]
Total share-based compensation expense			$ 0.8	$ 0.3	$ 27	$ 9.4
Unrecognized compensation cost, period of recognition					6 years
Affiliated entity
Related Party Transaction [Line Items]
Related party loans outstanding			$ 3.4		$ 3.4		$ 4.3
Affiliated entity | Weighted-average interest rate of loans receivable
Related Party Transaction [Line Items]
Interest rate					2.87%		2.80%
Affiliated entity | Unvested shares accepted for settlement of loan
Related Party Transaction [Line Items]
Related party transaction, shares (in shares)		0.3
Affiliated entity | Vested shares accepted for settlement of loan
Related Party Transaction [Line Items]
Related party transaction, shares (in shares)		0.1
Affiliated entity | Extinguishment of related party loan and accrued interest
Related Party Transaction [Line Items]
Amount of related party transaction		$ 0.9
Affiliated entity | Recognition of treasury stock
Related Party Transaction [Line Items]
Amount of related party transaction		$ 0.7
Subsequent event | Affiliated entity
Related Party Transaction [Line Items]
Number of options vested (in shares)	0.5
Unrecognized compensation cost	$ 3.1
Subsequent event | Affiliated entity | Incremental share-based compensation cost
Related Party Transaction [Line Items]
Expenses with related party	3.4
Subsequent event | Options | Affiliated entity
Related Party Transaction [Line Items]
Total share-based compensation expense	$ 0.3
Unrecognized compensation cost, period of recognition	6 years

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, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	$ (487.2)	$ (189.5)	$ (374)	$ (102.7)
Net current period other comprehensive income	0.1	0.1	5	0.8
Ending balance	(570.4)	(289.2)	(570.4)	(289.2)
Change in net unrealized gains on investment:
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Beginning balance	5.5	0.7	0.6	0
Other comprehensive income before reclassifications	0.2	0.1	5.2	0.8
Realized gains on investments reclassified from AOCI to net income	(0.1)	0	(0.2)	0
Net current period other comprehensive income	0.1	0.1	5	0.8
Ending balance	$ 5.6	$ 0.8	$ 5.6	$ 0.8

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, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Earnings Per Share [Abstract]
Exercise price of warrants (in dollars per share)	$ 0.0001		$ 0.0001
Net loss	$ (85.2)	$ (100.2)	$ (229.7)	$ (197.2)
Weighted-average common shares outstanding: basic and diluted (in shares)	38.8	34.8	38.7	32.9
Loss per common share: basic and diluted (in dollars per share)	$ (2.20)	$ (2.88)	$ (5.94)	$ (5.99)

LOSS PER SHARE - Schedule of An

LOSS PER SHARE - Schedule of Anti-Dilutive Securities (Details) - shares shares in Millions	9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities	174	171.4
Options to purchase common stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities	11.6	11.9
Redeemable convertible preferred stock (as converted to common stock)
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Anti-dilutive securities	161.8	158.9
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	0.6	0.6

GEOGRAPHICAL BREAKDOWN OF DIR_3

GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Effects of Reinsurance [Line Items]
Direct premiums written	$ 164.6	$ 119.6	$ 471.1	$ 307.4
Texas
Effects of Reinsurance [Line Items]
Direct premiums written	35.2	23.6	100.4	68.1
Georgia
Effects of Reinsurance [Line Items]
Direct premiums written	18.8	11.6	56.4	23.2
Kentucky
Effects of Reinsurance [Line Items]
Direct premiums written	7.8	11.5	27.7	34.1
Pennsylvania
Effects of Reinsurance [Line Items]
Direct premiums written	7.9	7.1	23.1	17.2
Arizona
Effects of Reinsurance [Line Items]
Direct premiums written	7.9	7.5	22.9	18.8
Missouri
Effects of Reinsurance [Line Items]
Direct premiums written	7.5	5.8	21.1	15.4
Louisiana
Effects of Reinsurance [Line Items]
Direct premiums written	8	4.7	20.6	10.1
Utah
Effects of Reinsurance [Line Items]
Direct premiums written	6.9	4.8	19.1	12.2
Ohio
Effects of Reinsurance [Line Items]
Direct premiums written	5.6	6.4	16.6	17.2
Oregon
Effects of Reinsurance [Line Items]
Direct premiums written	6.5	3.1	16.3	7.8
All others states
Effects of Reinsurance [Line Items]
Direct premiums written	$ 52.5	$ 33.5	$ 146.9	$ 83.3
Geographic Concentration Risk | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	100.00%	100.00%	100.00%	100.00%
Geographic Concentration Risk | Texas | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	21.40%	19.70%	21.30%	22.20%
Geographic Concentration Risk | Georgia | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	11.40%	9.70%	12.00%	7.50%
Geographic Concentration Risk | Kentucky | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.70%	9.60%	5.90%	11.10%
Geographic Concentration Risk | Pennsylvania | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.80%	5.90%	4.90%	5.60%
Geographic Concentration Risk | Arizona | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.80%	6.30%	4.90%	6.10%
Geographic Concentration Risk | Missouri | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.60%	4.80%	4.50%	5.00%
Geographic Concentration Risk | Louisiana | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.90%	3.90%	4.40%	3.30%
Geographic Concentration Risk | Utah | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.20%	4.00%	4.10%	4.00%
Geographic Concentration Risk | Ohio | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	3.40%	5.40%	3.50%	5.60%
Geographic Concentration Risk | Oregon | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	4.00%	2.60%	3.50%	2.50%
Geographic Concentration Risk | All others states | Direct Written Premiums
Effects of Reinsurance [Line Items]
Concentration percentage	31.80%	28.10%	31.00%	27.10%

SUBSEQUENT EVENTS (Details)

SUBSEQUENT EVENTS (Details) $ / shares in Units, $ in Millions	1 Months Ended		3 Months Ended	9 Months Ended
	Nov. 30, 2020USD ($)state	Oct. 31, 2020USD ($)vote$ / sharesshares	Sep. 30, 2019USD ($)	Sep. 30, 2019USD ($)	Sep. 30, 2020state$ / sharesshares	Dec. 31, 2019$ / sharesshares
Subsequent Event [Line Items]
Common stock, shares authorized (in shares)					269,000,000	266,000,000
Shares authorized (in shares)					170,000,000	167,400,000
Par value (in dollars per share) | $ / shares					$ 0.0001	$ 0.0001
Common stock, par value (in dollars per share) | $ / shares					$ 0.0001	$ 0.0001
Stock issuance costs | $			$ 0.1	$ 0.1
Number of states auto policies written | state					30
Subsequent event
Subsequent Event [Line Items]
Shares authorized (in shares)		100,000,000
Par value (in dollars per share) | $ / shares		$ 0.0001
Common stock, par value (in dollars per share) | $ / shares		$ 0.0001
Proceeds from sale of stock | $		$ 1,100
Stock issuance costs | $		$ 53.4
Number of warrants exercised (in shares)		2,800,000
Interest expense recognized | $		$ 38.7
Number of states auto policies written | state	48
Subsequent event | Shell insurance company
Subsequent Event [Line Items]
Purchase price | $	$ 22.8
Cash, cash equivalents and investment income acquired | $	14.4
Indefinite-lived asset acquired | $	$ 8.4
Subsequent event | 2020 Equity Incentive Plan
Subsequent Event [Line Items]
Shares authorized (in shares)		41,200,000
Annual shares increase, percentage of outstanding stock		4.00%
Subsequent event | 2020 ESPP
Subsequent Event [Line Items]
Shares authorized (in shares)		5,000,000
Annual shares increase, percentage of outstanding stock		1.00%
Subsequent event | IPO | Common stock
Subsequent Event [Line Items]
Stock sold in transaction (in shares)		24,200,000
Price of stock sold (in dollars per share) | $ / shares		$ 27
Class A Common Stock | Subsequent event
Subsequent Event [Line Items]
Common stock, shares authorized (in shares)		1,000,000,000
Votes per share | vote		1
Class A Common Stock | Subsequent event | 2020 Equity Incentive Plan
Subsequent Event [Line Items]
Maximum shares allowed to be issued (in shares)		120,000,000
Class A Common Stock | Subsequent event | 2020 ESPP
Subsequent Event [Line Items]
Shares outstanding, annual shares increase (in shares)		7,500,000
Class A Common Stock | Subsequent event | Private placement
Subsequent Event [Line Items]
Stock sold in transaction (in shares)		18,500,000
Class B Common Stock | Subsequent event
Subsequent Event [Line Items]
Common stock, shares authorized (in shares)		269,000,000
Votes per share | vote		10