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<!--XBRL Document Created with Wdesk from Workiva-->
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    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_3f29fd6e-bd57-4b84-9aa6-01f462ed796d_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Supplemental disclosures:</link:label>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_label_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Supplemental Cash Flow Information [Abstract]</link:label>
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    <link:label id="lab_us-gaap_CurrentStateAndLocalTaxExpenseBenefit_ee95a9ae-1caa-4f9b-9510-9ca127ca6631_terseLabel_en-US" xlink:label="lab_us-gaap_CurrentStateAndLocalTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">State</link:label>
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    <link:label id="lab_us-gaap_LeaseholdImprovementsMember_e47f6f0c-e8fb-4676-a21e-464499ce0ee2_terseLabel_en-US" xlink:label="lab_us-gaap_LeaseholdImprovementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Leasehold improvements</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent_9edd9b8c-09e7-4249-a084-ac78989984be_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments (amortized cost: zero and $3.0 at December&#160;31, 2021 and December&#160;31, 2020, respectively)</link:label>
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    <link:label id="lab_us-gaap_DirectPremiumsEarned_9528fc41-53c5-4d81-a10a-607bfe24087b_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeDomain" xlink:to="lab_us-gaap_SubsequentEventTypeDomain" xlink:type="arc" order="1"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_DeferredTaxAssetsLiabilitiesNet"/>
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    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent_569b2062-4bd4-4f0b-b198-5e21d71a72d5_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted average discount rate ( in percent)</link:label>
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    <link:label id="lab_us-gaap_SubsidiarySaleOfStockAxis_f70f7597-496d-4668-bd51-7a66602f3c2d_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock [Axis]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsidiarySaleOfStockAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_SubsidiarySaleOfStockAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsidiarySaleOfStockAxis" xlink:to="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock_5603730d-511b-4620-b864-c47b01c573de_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reconciliation of claims development to liability</link:label>
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    <link:label id="lab_us-gaap_SubsequentEventsAbstract_54003c5a-27dc-41c1-8294-a841fef13dd9_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Events [Abstract]</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsNet_ff51d68e-2c92-4e9e-911c-05ab893f4c06_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total deferred tax assets, less valuation allowance</link:label>
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    <link:label id="lab_srt_CondensedCashFlowStatementTable_9fb23231-c9ff-4691-a454-bf5a78bd1cc2_terseLabel_en-US" xlink:label="lab_srt_CondensedCashFlowStatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Cash Flow Statement [Table]</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_2d7ed3ae-879d-4ad5-893c-a1184d940a6e_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Domain]</link:label>
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    <link:label id="lab_root_TemporaryEquitySharesTenderOffer_6a629b3e-76cb-48f8-b94e-2168b24d47f5_terseLabel_en-US" xlink:label="lab_root_TemporaryEquitySharesTenderOffer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tender offer and subsequent conversion (Note 11) (in shares)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_root_TemporaryEquitySharesTenderOffer" xlink:href="root-20211231.xsd#root_TemporaryEquitySharesTenderOffer"/>
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    <link:label id="lab_root_TemporaryEquityStockIssuedDuringPeriodValueConversionOfPreferredStock_d99d6cd7-9ced-42d5-bee0-968af6fef0ba_negatedTerseLabel_en-US" xlink:label="lab_root_TemporaryEquityStockIssuedDuringPeriodValueConversionOfPreferredStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of redeemable convertible preferred stock to common stock from IPO</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentInformationLineItems" xlink:href="https://xbrl.sec.gov/dei/2021q4/dei-2021q4.xsd#dei_DocumentInformationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentInformationLineItems" xlink:to="lab_dei_DocumentInformationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock_d23f8e26-04c1-4993-96e7-341f969f9228_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfConvertiblePreferredStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from issuance of convertible stock</link:label>
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    <link:label id="lab_root_IncreaseDecreaseInIntercompanyAssetsAndLiabilitiesNet_020cfdec-a7cd-4a28-9a84-7c07d6f9a18f_negatedTerseLabel_en-US" xlink:label="lab_root_IncreaseDecreaseInIntercompanyAssetsAndLiabilitiesNet" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intercompany, net</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_3121ca4e-a681-4f4c-81d6-ceb82d57fa84_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance (in shares)</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_3fa5b52a-56e0-4f55-b1ed-f8b264687f41_verboseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after one year through five years, amortized cost</link:label>
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    <link:label id="lab_root_LineOfCreditFacilityFrontingFeePercentage_7dec6123-5540-4c54-9e2c-bec7ee539d42_terseLabel_en-US" xlink:label="lab_root_LineOfCreditFacilityFrontingFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fronting fee percentage</link:label>
    <link:label id="lab_root_LineOfCreditFacilityFrontingFeePercentage_label_en-US" xlink:label="lab_root_LineOfCreditFacilityFrontingFeePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line Of Credit Facility, Fronting Fee Percentage</link:label>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member_2694ed94-4815-45a4-a95a-4ff0f0eb3665_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2021</link:label>
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    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_d1bcbb09-260e-43de-85f8-5dc5c56ac342_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_63f8dac1-dd84-4533-8d0d-15cdeb8236c7_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Gains</link:label>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_20fc16ef-8f74-4f07-bf01-09c865dd979f_verboseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization of deferred acquisition costs</link:label>
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    <link:label id="lab_root_GrossWrittenPremiumsMember_a234f1b1-650b-4ed6-9f8f-128ba7438bb1_terseLabel_en-US" xlink:label="lab_root_GrossWrittenPremiumsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Written Premiums</link:label>
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    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_1a8bf829-63b4-465c-999e-e6213f4d5c90_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General and administrative</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ExercisePriceRangeThreeMember" xlink:to="lab_root_ExercisePriceRangeThreeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_c0ee0db2-94a6-46b8-913d-71ca30a996ab_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term Debt, Type [Domain]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term Debt, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeDomain" xlink:to="lab_us-gaap_LongtermDebtTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestPayableCurrentAndNoncurrent_c9320044-58dc-4a54-aa3a-63618d5d7cfb_terseLabel_en-US" xlink:label="lab_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accrued interest payable</link:label>
    <link:label id="lab_us-gaap_InterestPayableCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_InterestPayableCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:to="lab_us-gaap_InterestPayableCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights_f9b839e1-988c-443f-94a3-394d6e3ed5ab_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares issued (in shares)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ClassOfWarrantOrRightNumberOfSecuritiesCalledByWarrantsOrRights"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_4c343c35-d31c-4622-8fec-0de08502c8a5_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses reserves</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve"/>
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    <link:label id="lab_us-gaap_OtherAssetsMember_07068e94-374c-429c-a2ee-3e3a1218a526_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Assets</link:label>
    <link:label id="lab_us-gaap_OtherAssetsMember_label_en-US" xlink:label="lab_us-gaap_OtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Assets [Member]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAssetsMember" xlink:to="lab_us-gaap_OtherAssetsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseShareBasedCompensationCost_dbcbd1bc-182e-4b64-9ca6-29a0653ffc04_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationNondeductibleExpenseShareBasedCompensationCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based compensation</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxReconciliationNondeductibleExpenseShareBasedCompensationCost" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_IncomeTaxReconciliationNondeductibleExpenseShareBasedCompensationCost"/>
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    <link:label id="lab_root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent_1ed212fd-c3fa-4c69-a13e-a4d573778532_terseLabel_en-US" xlink:label="lab_root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional warrant to purchase shares (in percent)</link:label>
    <link:label id="lab_root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent_label_en-US" xlink:label="lab_root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right,Additional Warrant To Purchase Shares, Percent</link:label>
    <link:label id="lab_root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent_documentation_en-US" xlink:label="lab_root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right,Additional Warrant To Purchase Shares, Percent</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent" xlink:to="lab_root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_fac06d11-cbb4-4f77-84e8-6a2e908655c2_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_label_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term Debt, Fair Value</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtFairValue" xlink:to="lab_us-gaap_LongTermDebtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities_d76944c2-01ff-4971-9d33-82ecc964676c_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other liabilities</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Other Operating Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_IncreaseDecreaseInOtherOperatingLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:to="lab_us-gaap_IncreaseDecreaseInOtherOperatingLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MaximumMember_7a459149-78da-48fd-ae96-a3e88d3ff487_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum</link:label>
    <link:label id="lab_srt_MaximumMember_label_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2021/elts/srt-2021-01-31.xsd#srt_MaximumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MaximumMember" xlink:to="lab_srt_MaximumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_1edbda7b-4768-4dcf-b6a5-866bfc608d2d_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Payment Arrangement [Abstract]</link:label>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Payment Arrangement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract_958f3a0a-41f3-497a-9ee7-e31b681df6d4_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Percent</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Percent [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_root_TermLoanAMember_f3781084-5259-42d8-b6d0-1191cfdfd609_terseLabel_en-US" xlink:label="lab_root_TermLoanAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan A</link:label>
    <link:label id="lab_root_TermLoanAMember_label_en-US" xlink:label="lab_root_TermLoanAMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan A [Member]</link:label>
    <link:label id="lab_root_TermLoanAMember_documentation_en-US" xlink:label="lab_root_TermLoanAMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan A</link:label>
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    <link:label id="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount_d83cfaef-44b1-4f3a-a5ba-37cceab02fe3_terseLabel_en-US" xlink:label="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">State net operating loss</link:label>
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    <link:label id="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount_documentation_en-US" xlink:label="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax, Operating Loss Carryforwards, State And Local, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount" xlink:href="root-20211231.xsd#root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount" xlink:to="lab_root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AwardTypeAxis_e9f3ed65-4731-4564-98ef-b3b1d5d5d78b_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:label id="lab_us-gaap_AwardTypeAxis_label_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_AwardTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AwardTypeAxis" xlink:to="lab_us-gaap_AwardTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_79ac2eba-43d1-47ad-aca6-2640956c7c03_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash flows from financing activities:</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock_78f489a6-4faa-4af8-b9da-7f44a78bc059_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of future lease payments</link:label>
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    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember_c14b7cdd-7000-431c-8d71-07c614d9bc78_terseLabel_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss and loss adjustment expenses</link:label>
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    <link:label id="lab_us-gaap_DebtConversionConvertedInstrumentAmount1_97eae3b0-69a4-4a3b-8441-45f2cf76ce6d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtConversionConvertedInstrumentAmount1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of debt to preferred stock - non-cash</link:label>
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    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_d73b310c-7da3-4e1d-a58f-846821301dc5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchases of treasury stock</link:label>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_label_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments for Repurchase of Common Stock</link:label>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife_34a5bc3a-01b0-41da-aa5d-e2ef69d281d6_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Useful life</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment, Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_PropertyPlantAndEquipmentUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract_622379b7-66a9-4b33-af1b-0767fbd1bca1_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAbstract"/>
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    <link:label id="lab_root_ProceedsFromSimpleAgreementForFutureEquity_c28c3d23-f90f-412a-aa1a-2c48acc667f4_terseLabel_en-US" xlink:label="lab_root_ProceedsFromSimpleAgreementForFutureEquity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from SAFE</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_root_ProceedsFromSimpleAgreementForFutureEquity" xlink:href="root-20211231.xsd#root_ProceedsFromSimpleAgreementForFutureEquity"/>
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    <link:label id="lab_us-gaap_StockholdersEquityAbstract_89491f41-080e-4614-b372-8c650e7c70e0_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders&#8217; equity:</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseShareBasedCompensationCost" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationNondeductibleExpenseShareBasedCompensationCost"/>
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    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_8f3329e9-fb21-42e1-860b-b7547fbd8e90_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrecognized compensation cost</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions"/>
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    <link:label id="lab_us-gaap_EquityComponentDomain_7202e3a2-9adc-406e-8f37-f1733ac00cb4_terseLabel_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityComponentDomain_label_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Component [Domain]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityComponentDomain" xlink:to="lab_us-gaap_EquityComponentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_root_AmendedTermLoanAMember_cb28fefa-5a3c-40c2-b158-9766648fde7d_terseLabel_en-US" xlink:label="lab_root_AmendedTermLoanAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amended Term Loan A</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_3346f045-4255-4e97-be6d-a6fda28034bc_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2022</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year One</link:label>
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    <link:label id="lab_root_OtherInsuranceExpenseIncome_1df629c6-d710-4d15-8ed1-ffda02f406c6_terseLabel_en-US" xlink:label="lab_root_OtherInsuranceExpenseIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other insurance expense (benefit)</link:label>
    <link:label id="lab_root_OtherInsuranceExpenseIncome_label_en-US" xlink:label="lab_root_OtherInsuranceExpenseIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Insurance Expense (Income)</link:label>
    <link:label id="lab_root_OtherInsuranceExpenseIncome_documentation_en-US" xlink:label="lab_root_OtherInsuranceExpenseIncome" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Insurance Expense (Income)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_OtherInsuranceExpenseIncome" xlink:href="root-20211231.xsd#root_OtherInsuranceExpenseIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_OtherInsuranceExpenseIncome" xlink:to="lab_root_OtherInsuranceExpenseIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ExercisePriceRangeTwoMember_6b92021d-fad5-486b-aa46-309e412da8da_terseLabel_en-US" xlink:label="lab_root_ExercisePriceRangeTwoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">$1.00 - $2.50</link:label>
    <link:label id="lab_root_ExercisePriceRangeTwoMember_label_en-US" xlink:label="lab_root_ExercisePriceRangeTwoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercise Price Range Two [Member]</link:label>
    <link:label id="lab_root_ExercisePriceRangeTwoMember_documentation_en-US" xlink:label="lab_root_ExercisePriceRangeTwoMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercise Price Range Two</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ExercisePriceRangeTwoMember" xlink:to="lab_root_ExercisePriceRangeTwoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract_110923d1-5497-43eb-825d-0d3011a4239e_terseLabel_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred tax assets:</link:label>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract_label_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Components of Deferred Tax Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ComponentsOfDeferredTaxAssetsAbstract"/>
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    <link:label id="lab_us-gaap_OtherIncome_1a3d3462-6dca-4107-b31c-0dcb6561bc55_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other income</link:label>
    <link:label id="lab_us-gaap_OtherIncome_label_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_OtherIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncome" xlink:to="lab_us-gaap_OtherIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent_c1ba716a-bf03-4807-8969-f56a1c3a7f57_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturities available-for-sale, at fair value (amortized cost: $129.5 and $215.4 at December&#160;31, 2021 and December&#160;31, 2020, respectively)</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-sale, Noncurrent</link:label>
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    <link:label id="lab_us-gaap_LiabilitiesAbstract_1e0ef520-a357-4c21-96f5-5c2c2c071d17_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities:</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_LiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAbstract" xlink:to="lab_us-gaap_LiabilitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationChangeInDeferredTaxAssetsValuationAllowance_7322beba-1ba0-46ac-ab18-5c48a8fc5dc6_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationChangeInDeferredTaxAssetsValuationAllowance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Valuation allowance on deferred tax assets</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationChangeInDeferredTaxAssetsValuationAllowance_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationChangeInDeferredTaxAssetsValuationAllowance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Change in Deferred Tax Assets Valuation Allowance, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationChangeInDeferredTaxAssetsValuationAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationChangeInDeferredTaxAssetsValuationAllowance"/>
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    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_42c3ed4b-24e0-476c-887b-ec1745b5a0be_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermInvestmentsMember" xlink:to="lab_us-gaap_ShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_64d84c59-a297-40d9-82ec-0e110f00fc24_terseLabel_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_label_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:href="https://xbrl.fasb.org/srt/2021/elts/srt-2021-01-31.xsd#srt_RepurchaseAgreementCounterpartyNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:to="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockRetiredCostMethodAmount_14f2b0b5-1e40-4465-8bc5-c2a75fee5e4e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockRetiredCostMethodAmount" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retirement of treasury shares</link:label>
    <link:label id="lab_us-gaap_TreasuryStockRetiredCostMethodAmount_f4195c29-911b-4aee-9f81-1656a350c4cd_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockRetiredCostMethodAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retirement of treasury shares</link:label>
    <link:label id="lab_us-gaap_TreasuryStockRetiredCostMethodAmount_label_en-US" xlink:label="lab_us-gaap_TreasuryStockRetiredCostMethodAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Retired, Cost Method, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockRetiredCostMethodAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_TreasuryStockRetiredCostMethodAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockRetiredCostMethodAmount" xlink:to="lab_us-gaap_TreasuryStockRetiredCostMethodAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_7b39c8db-a74a-4274-974a-9551611d2633_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2025</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour"/>
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    <link:label id="lab_dei_DocumentType_e5b61d67-b7f7-41e9-8511-ab558c4c4559_terseLabel_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Type</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock_3f4169ba-216c-4d8b-941f-b8d457057130_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedRestrictedStockUnitsActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of RSU activity</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_6cae86aa-f5d0-45c5-9909-9c48fb2811a4_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reconciliation of reserve balances for loss and LAE, net of reinsurance</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_ab1f46c2-42c8-447b-aa5c-332ff922b02e_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest rate (in percent)</link:label>
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    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_102bfe38-419d-46bf-bb1b-87d3ef5c283b_terseLabel_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_label_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Investment Income, Operating</link:label>
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    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_99639df4-eb13-4585-a45a-8225eeb03245_terseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prepaid reinsurance premiums</link:label>
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    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_d7940f7e-9bda-4f6c-873a-1a7be4dbc034_terseLabel_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving Loan</link:label>
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    <link:label id="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember_18cac8d2-0719-4ccf-a6fe-6e670ced6de9_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Valuation allowance for deferred tax assets</link:label>
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    <link:label id="lab_us-gaap_RedeemableConvertiblePreferredStockMember_8465ca82-6806-46bb-8ca3-b83bb2c9c98a_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Redeemable convertible preferred stock (as converted to common stock)</link:label>
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    <link:label id="lab_srt_StatementGeographicalAxis_ad163640-3433-42f5-ad5a-ed6cdbf6cdd9_terseLabel_en-US" xlink:label="lab_srt_StatementGeographicalAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Geographical [Axis]</link:label>
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    <link:label id="lab_us-gaap_StateAndLocalJurisdictionMember_b7e19848-33ce-4fc8-a561-3c623bcfe0d2_terseLabel_en-US" xlink:label="lab_us-gaap_StateAndLocalJurisdictionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">State</link:label>
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    <link:label id="lab_us-gaap_VestingDomain_label_en-US" xlink:label="lab_us-gaap_VestingDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vesting [Domain]</link:label>
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    <link:label id="lab_root_CededCommissionsMaximumAmountDueWithReturnOfUnpaidPremiums_7eb22bdd-0c46-49cb-9be7-52e31025382e_terseLabel_en-US" xlink:label="lab_root_CededCommissionsMaximumAmountDueWithReturnOfUnpaidPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum amount of ceded commissions returned</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventsTextBlock" xlink:to="lab_us-gaap_SubsequentEventsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquitySharesAuthorized_2903f934-46df-40bd-84e4-b492f4c7bb95_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares authorized (in shares)</link:label>
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    <link:label id="lab_us-gaap_InvestmentPolicyTextBlock_3fc4ba18-9a33-4fc9-9835-cb23f52abcd2_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments</link:label>
    <link:label id="lab_us-gaap_InvestmentPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_InvestmentPolicyTextBlock"/>
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    <link:label id="lab_us-gaap_UnrealizedGainLossOnInvestments_ca0d789a-13f5-4d71-819d-3ed30e72371a_terseLabel_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized gains</link:label>
    <link:label id="lab_us-gaap_UnrealizedGainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnrealizedGainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_UnrealizedGainLossOnInvestments"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_bbebb186-6a9b-4027-879e-8e61922fc0e6_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash (used in) provided by financing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Financing Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
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    <link:label id="lab_us-gaap_TreasuryStockValue_f6b9b57e-2ce0-4734-920a-64cdff195152_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury stock, at cost</link:label>
    <link:label id="lab_us-gaap_TreasuryStockValue_label_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_TreasuryStockValue"/>
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    <link:label id="lab_us-gaap_CededPremiumsWritten_d9a574d3-2c00-470a-b08a-673a2a48e8e7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_CededPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsWritten" xlink:to="lab_us-gaap_CededPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1_f2ef8f1a-8135-4537-a240-c42f26ce8a20_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vesting period</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Award Vesting Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1"/>
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    <link:label id="lab_root_TechnologyAndDevelopmentExpense_8e51904d-7dc1-4fbd-bec6-57f70b0ab00f_terseLabel_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology and development</link:label>
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    <link:label id="lab_root_TechnologyAndDevelopmentExpense_documentation_en-US" xlink:label="lab_root_TechnologyAndDevelopmentExpense" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology And Development Expense</link:label>
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    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_ffda6b55-698e-4712-8255-9a4d49654a59_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">FAIR VALUE OF FINANCIAL INSTRUMENTS</link:label>
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    <link:label id="lab_us-gaap_RestructuringCharges_8a0f4148-c0a3-4205-94ba-ae1d16ab58c3_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCharges" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring charges</link:label>
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    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_7e8b939d-a7c7-4c64-94f5-b5b4aebafad1_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentGross_c6d75d9b-a000-43e0-8fb8-af7efa1eb7e6_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total fixed assets, at cost</link:label>
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    <link:label id="lab_us-gaap_PremiumsWrittenNet_526dcbb6-9a69-4088-a6f5-69b7c3a4f6df_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums written</link:label>
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    <link:label id="lab_us-gaap_LeasesAbstract_label_en-US" xlink:label="lab_us-gaap_LeasesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Leases [Abstract]</link:label>
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    <link:label id="lab_us-gaap_LondonInterbankOfferedRateLIBORMember_e7d231fa-81ce-4ed4-9616-496375b585ac_terseLabel_en-US" xlink:label="lab_us-gaap_LondonInterbankOfferedRateLIBORMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">LIBOR</link:label>
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    <link:label id="lab_us-gaap_SeriesEPreferredStockMember_77f423cd-94b0-4ce9-b94e-8b197bc10ec2_terseLabel_en-US" xlink:label="lab_us-gaap_SeriesEPreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Series E Preferred Stock</link:label>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems_aa06c6a5-573a-4359-b302-1c7ef647ff17_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss) [Line Items]</link:label>
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    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_a93457dd-1da8-4202-bea8-13031b1b3e66_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct</link:label>
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    <link:label id="lab_dei_EntityAddressPostalZipCode_0f598fe5-3f0b-48fe-9913-d7d83537b47e_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
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    <link:label id="lab_us-gaap_PurchaseObligation_3b2625f5-c01f-407c-843d-ae1cc4548e63_totalLabel_en-US" xlink:label="lab_us-gaap_PurchaseObligation" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
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    <link:label id="lab_us-gaap_CreditFacilityAxis_5df21b93-6fac-4553-a8fc-9e01642a272f_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityAxis_label_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Axis]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityAxis" xlink:to="lab_us-gaap_CreditFacilityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine1_f8aa4d39-7801-4b91-90e4-ae1e37489828_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line One</link:label>
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    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpenseMember_86646607-643b-4980-864b-807db11e55a5_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General and administrative</link:label>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpenseMember_label_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General and Administrative Expense [Member]</link:label>
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    <link:label id="lab_us-gaap_ConsolidationPolicyTextBlock_4ea48f57-b1d2-4c29-8979-57349226e5e8_terseLabel_en-US" xlink:label="lab_us-gaap_ConsolidationPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consolidation</link:label>
    <link:label id="lab_us-gaap_ConsolidationPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_ConsolidationPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consolidation, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConsolidationPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ConsolidationPolicyTextBlock"/>
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    <link:label id="lab_dei_EntityShellCompany_000d7d9f-a9b2-49f2-8cc6-34b26c20ba34_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Shell Company</link:label>
    <link:label id="lab_dei_EntityShellCompany_label_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Shell Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityShellCompany" xlink:href="https://xbrl.sec.gov/dei/2021q4/dei-2021q4.xsd#dei_EntityShellCompany"/>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_c3c6796e-1513-4458-8843-9fd219db1301_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred policy acquisition cost</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
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    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1_7c22b112-d21e-44ca-9186-e290e4355c20_verboseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Expected term</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardFairValueAssumptionsExpectedTerm1"/>
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    <link:label id="lab_us-gaap_AssumedPremiumsWritten_b0a57e27-5a3e-4a08-acac-47205e67ce04_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed</link:label>
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    <link:label id="lab_dei_CurrentFiscalYearEndDate_3f9ba269-6090-476b-b060-a328d65ff6e8_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current Fiscal Year End Date</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_681963b3-1a7b-4924-adcd-3d9fa4186eed_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unamortized discount and debt and warrant issuance costs</link:label>
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    <link:label id="lab_us-gaap_StatementTable_d189e893-196f-4e47-aaa6-15cbebcf3c0c_terseLabel_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Table]</link:label>
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    <link:label id="lab_srt_RangeMember_68beaf39-c807-40e8-9d95-d72bc510815c_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:label id="lab_srt_RangeMember_label_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeMember" xlink:to="lab_srt_RangeMember" xlink:type="arc" order="1"/>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardIncreaseInNumberOfSharesAvailableForGrantPercentageOfSharesOutstanding" xlink:to="lab_root_ShareBasedCompensationArrangementByShareBasedPaymentAwardIncreaseInNumberOfSharesAvailableForGrantPercentageOfSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_root_EarlyExerciseDepositLiability_75b58106-4fc9-4727-9a83-e7e7d6b56950_terseLabel_en-US" xlink:label="lab_root_EarlyExerciseDepositLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercise deposit liability</link:label>
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    <link:label id="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock_6ea3baf5-6a94-46b0-85d2-b8fc4df9a170_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Segment Information</link:label>
    <link:label id="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Segment Reporting, Policy [Policy Text Block]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_1c60f021-0f51-4d46-b08d-bca83f4f9d03_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_label_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
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    <link:label id="lab_us-gaap_RestructuringCostAndReserveAxis_d9c8d033-9d0c-46d9-a79d-282bd9d6118c_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringCostAndReserveAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restructuring Type [Axis]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestructuringCostAndReserveAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_RestructuringCostAndReserveAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestructuringCostAndReserveAxis" xlink:to="lab_us-gaap_RestructuringCostAndReserveAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_4d467a35-a7f0-4562-ad55-9d754c1f27a5_periodStartLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance (in shares)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_3c0b1687-3c20-4652-9a36-ff20d5916a0b_periodEndLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance (in shares)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquitySharesOutstanding_label_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Temporary Equity, Shares Outstanding</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquitySharesOutstanding" xlink:to="lab_us-gaap_TemporaryEquitySharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy_32d1f562-985f-49cc-acb5-52a1bd7ba7a3_terseLabel_en-US" xlink:label="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Policy Acquisition Costs</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedDividendRate_48449e8c-38a5-4f76-9af6-0be2f4c03bf7_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedDividendRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Expected dividend rate</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedDividendRate" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedDividendRate"/>
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    <link:label id="lab_dei_EntityFileNumber_137401a6-de60-41e2-bb0a-350cca185241_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity File Number</link:label>
    <link:label id="lab_dei_EntityFileNumber_label_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity File Number</link:label>
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    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue_22e4dd41-c951-416c-8490-69858e8911a1_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock&#8212;share-based compensation expense</link:label>
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    <link:label id="lab_root_AuditInformationAbstract_label_en-US" xlink:label="lab_root_AuditInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Audit Information [Abstract]</link:label>
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    <link:label id="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems_e6d2d8da-ee4a-48e2-a327-5500f2180360_terseLabel_en-US" xlink:label="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Balance Sheet Statements, Captions [Line Items]</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod_ccd43d99-2999-48cf-996e-0bf65756dfcd_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsForfeituresAndExpirationsInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited, expired or canceled (in shares)</link:label>
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    <link:label id="lab_us-gaap_PurchaseObligationDueInThirdYear_label_en-US" xlink:label="lab_us-gaap_PurchaseObligationDueInThirdYear" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase Obligation, to be Paid, Year Three</link:label>
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    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossesNet_7e4948df-0281-4062-b3d3-00017005fc55_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossesNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss and ALAE reserves&#8212;net of reinsurance</link:label>
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    <link:label id="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices_ba499f46-6a82-4af3-824a-b2c9cf2da747_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentOfWarrantsGrantedForServices" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrant compensation expense</link:label>
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    <link:label id="lab_us-gaap_SharebasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeExercisableOptionsWeightedAverageRemainingContractualTerm2_dc342898-00a6-41eb-b3b5-897bc59009bb_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeExercisableOptionsWeightedAverageRemainingContractualTerm2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Options exercisable, weighted-average remaining contractual term (in years)</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized_c78f7a0e-8a6c-41f7-a21a-1efb266b13fc_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares authorized (in shares)</link:label>
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    <link:label id="lab_us-gaap_OperatingLeasePayments_f1bdac74-5927-4e6b-a7f6-474e12bb5555_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeasePayments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating lease, liabilities</link:label>
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    <link:label id="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated_e8b45c19-534b-47f6-8258-a1e73be09730_terseLabel_en-US" xlink:label="lab_us-gaap_RestructuringAndRelatedCostNumberOfPositionsEliminated" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Number of positions eliminated</link:label>
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    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_9690a814-1dc3-441b-aea6-ae97b55c1744_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
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    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustedBalanceMember_13f4324a-bb2c-4285-bcb0-db458f8a81b9_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustedBalanceMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative Effect, Period of Adoption, Adjusted Balance</link:label>
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    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossAdjustmentExpenseNet_0ecebb8b-0be9-42f6-8d59-42f53870aac1_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">ULAE reserves&#8212;net of reinsurance</link:label>
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    <link:label id="lab_us-gaap_TemporaryEquityByClassOfStockTable_f56ec11c-c706-46df-9f82-f16738bf74ee_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityByClassOfStockTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Temporary Equity, by Class of Stock [Table]</link:label>
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    <link:label id="lab_us-gaap_ClassOfWarrantOrRightOutstanding_f5d8f269-77f5-4bbe-89a3-5f3c218bbc05_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants outstanding (in shares)</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount_0b887ca9-2be5-48cf-ad54-28bafedb7b24_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less: imputed interest</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_f5c15901-bad6-4116-8150-6f999f236ed6_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverable, net of allowance of $0.2 and zero at December 31, 2021 and December 31, 2020, respectively</link:label>
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    <link:label id="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract_ae2ab1a7-90d9-4349-b5d8-ffb303f4db86_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums written:</link:label>
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    <link:label id="lab_root_OtherInsuranceExpenseMember_7e374a3f-a994-4c9a-a328-e2b17873ebf6_terseLabel_en-US" xlink:label="lab_root_OtherInsuranceExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other insurance (benefit) expense</link:label>
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    <link:label id="lab_root_TemporaryEquityStockIssuedDuringPeriodSharesConversionOfPreferredStock_e48a643a-a043-46cb-9df6-87ddd4345818_negatedTerseLabel_en-US" xlink:label="lab_root_TemporaryEquityStockIssuedDuringPeriodSharesConversionOfPreferredStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of redeemable convertible preferred stock to common stock from IPO (in shares)</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensation_59dd5676-9142-45ba-9e59-6d3a2cb4a592_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based compensation</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Payment Arrangement, Noncash Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ShareBasedCompensation"/>
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    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_26f83b6e-06e1-4f0a-8f1d-818074cc6cfc_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and cash equivalents</link:label>
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    <link:label id="lab_us-gaap_Depreciation_ef8d5ab3-38e8-4470-8e2c-6332fb3913bc_terseLabel_en-US" xlink:label="lab_us-gaap_Depreciation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation expense</link:label>
    <link:label id="lab_us-gaap_Depreciation_label_en-US" xlink:label="lab_us-gaap_Depreciation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Depreciation" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_Depreciation"/>
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    <link:label id="lab_us-gaap_TreasuryStockMember_06d3fda5-e8e6-4d5f-9517-96b389f3ccf3_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock</link:label>
    <link:label id="lab_us-gaap_TreasuryStockMember_label_en-US" xlink:label="lab_us-gaap_TreasuryStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_TreasuryStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockMember" xlink:to="lab_us-gaap_TreasuryStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromSubsidiariesNetOfTax_03608382-83dd-44c5-8710-930c3a914eb9_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromSubsidiariesNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss of subsidiaries</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromSubsidiariesNetOfTax_f4a637fd-dcb4-4ace-8daa-d7c0cc23b53d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromSubsidiariesNetOfTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Change in equity in subsidiaries</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromSubsidiariesNetOfTax_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromSubsidiariesNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income (Loss) from Subsidiaries, Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromSubsidiariesNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_IncomeLossFromSubsidiariesNetOfTax"/>
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    <link:label id="lab_root_AllOtherStatesMember_c3e1db99-bd90-4c14-9105-a41f476a3bac_terseLabel_en-US" xlink:label="lab_root_AllOtherStatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">All others states</link:label>
    <link:label id="lab_root_AllOtherStatesMember_label_en-US" xlink:label="lab_root_AllOtherStatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">All Other States [Member]</link:label>
    <link:label id="lab_root_AllOtherStatesMember_documentation_en-US" xlink:label="lab_root_AllOtherStatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">All Other States</link:label>
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    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_014784e6-e270-4e90-b627-43aad8fedb4c_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchases of investments</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Debt Securities, Available-for-sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt"/>
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    <link:label id="lab_stpr_GA_b8f30870-8af2-489a-b9a7-887dade8a475_terseLabel_en-US" xlink:label="lab_stpr_GA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Georgia</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxesPaid_b54d41d3-c600-4d9e-99ab-691f68d64c0e_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaid" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Federal income taxes paid</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxesPaid" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_IncomeTaxesPaid"/>
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    <link:label id="lab_root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock_ec634f7c-964c-4cfd-b6c0-cbce648f6b07_terseLabel_en-US" xlink:label="lab_root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Capital Stock</link:label>
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    <link:label id="lab_us-gaap_StockIssued1_cf220713-0a7f-4bd0-a006-07d5e93a3a52_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssued1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of warrants to common stock - non-cash</link:label>
    <link:label id="lab_us-gaap_StockIssued1_label_en-US" xlink:label="lab_us-gaap_StockIssued1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Issued</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssued1" xlink:to="lab_us-gaap_StockIssued1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_b1598228-b034-4029-a9ee-41f9627cd169_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchases of fixed assets</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Property, Plant, and Equipment</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain_cca16b56-bf18-435e-b7b6-19048c160fc2_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-duration Insurance Contracts, Accident Year [Domain]</link:label>
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    <link:label id="lab_us-gaap_Liabilities_1a40f2b1-b64b-43a7-8766-03c68262311b_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total liabilities</link:label>
    <link:label id="lab_us-gaap_Liabilities_label_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_Liabilities"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodWeightedAverageExercisePrice"/>
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    <link:label id="lab_us-gaap_InterestPaidNet_210ab748-aaab-481f-9d1f-4f3b55e547ce_terseLabel_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest paid</link:label>
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    <link:label id="lab_srt_SegmentGeographicalDomain_47c0a88a-d68e-4b1c-842d-9d9affbc00a9_terseLabel_en-US" xlink:label="lab_srt_SegmentGeographicalDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Geographical [Domain]</link:label>
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    <link:label id="lab_us-gaap_StatutoryAccountingPracticesTable_604fb9d7-0538-4dad-b767-7f668e3da9de_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Practices [Table]</link:label>
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    <link:label id="lab_us-gaap_PremiumsEarnedNet_9749c7c4-cbe9-422b-80d7-5cc057d19063_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums earned</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_7a4e0fe5-9f01-4997-aeff-4ff557748af3_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums earned</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_label_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Earned, Net</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis_f34186b0-16f5-4d2f-8fba-5d19dad70e20_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-duration Insurance Contracts, Accident Year [Axis]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:href="https://xbrl.fasb.org/srt/2021/elts/srt-2021-01-31.xsd#srt_CumulativeEffectPeriodOfAdoptionDomain"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_ae8f204b-a252-447b-8278-17503fe4f0e7_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash used in operating activities</link:label>
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    <link:label id="lab_us-gaap_TaxCreditCarryforwardAmount_69040978-063d-4c50-8264-2e01fc80c9a4_terseLabel_en-US" xlink:label="lab_us-gaap_TaxCreditCarryforwardAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tax credit carryforwards</link:label>
    <link:label id="lab_us-gaap_TaxCreditCarryforwardAmount_label_en-US" xlink:label="lab_us-gaap_TaxCreditCarryforwardAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tax Credit Carryforward, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TaxCreditCarryforwardAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_TaxCreditCarryforwardAmount"/>
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    <link:label id="lab_us-gaap_FurnitureAndFixturesMember_53313acd-8cb1-48e6-a1b5-fd543eb976fc_terseLabel_en-US" xlink:label="lab_us-gaap_FurnitureAndFixturesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Furniture</link:label>
    <link:label id="lab_us-gaap_FurnitureAndFixturesMember_label_en-US" xlink:label="lab_us-gaap_FurnitureAndFixturesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Furniture and Fixtures [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FurnitureAndFixturesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_FurnitureAndFixturesMember"/>
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    <link:label id="lab_root_InvestmentsInSubsidiaries_7f73b255-2ba4-4929-b216-ee392c1db49b_terseLabel_en-US" xlink:label="lab_root_InvestmentsInSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments in subsidiaries</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentTable_824c1003-2e8b-410b-a554-edfb2ea1c509_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long-term Debt Instruments [Table]</link:label>
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    <link:label id="lab_us-gaap_DeferredChargesPolicyTextBlock_6848477e-4274-4990-9c7e-ef6c64eaae5f_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredChargesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt and Equity Issuance Costs</link:label>
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    <link:label id="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1_186b0dee-01eb-4215-b078-fae7b25ffc77_terseLabel_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exercise price of warrants (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1_label_en-US" xlink:label="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class of Warrant or Right, Exercise Price of Warrants or Rights</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:to="lab_us-gaap_ClassOfWarrantOrRightExercisePriceOfWarrantsOrRights1" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedIncomeStatementsCaptionsLineItems_3640a00e-45fc-4174-862a-ac7b95eb9485_terseLabel_en-US" xlink:label="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Income Statements, Captions [Line Items]</link:label>
    <link:label id="lab_srt_CondensedIncomeStatementsCaptionsLineItems_label_en-US" xlink:label="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Income Statements, Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:href="https://xbrl.fasb.org/srt/2021/elts/srt-2021-01-31.xsd#srt_CondensedIncomeStatementsCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:to="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_stpr_SC_0c9bcb4a-64eb-4493-b047-96620812fe42_terseLabel_en-US" xlink:label="lab_stpr_SC" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">South Carolina</link:label>
    <link:label id="lab_stpr_SC_label_en-US" xlink:label="lab_stpr_SC" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SOUTH CAROLINA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_stpr_SC" xlink:href="https://xbrl.sec.gov/stpr/2021/stpr-2021.xsd#stpr_SC"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_stpr_SC" xlink:to="lab_stpr_SC" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember_d998c5ef-c10b-44d2-b375-fde8f076f287_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tranche 3</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Payment Arrangement, Tranche Three [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ShareBasedCompensationAwardTrancheThreeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:to="lab_us-gaap_ShareBasedCompensationAwardTrancheThreeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_0d82b4ce-02a9-4417-a6fb-f64314c33da3_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sales of investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale of Debt Securities, Available-for-sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WarrantMember_50f4d1ea-d0eb-4aa8-b5b3-a07559c6877f_verboseLabel_en-US" xlink:label="lab_us-gaap_WarrantMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants</link:label>
    <link:label id="lab_us-gaap_WarrantMember_725a3f93-a663-4691-a053-604df3d2eced_terseLabel_en-US" xlink:label="lab_us-gaap_WarrantMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrants to purchase redeemable convertible preferred stock (as converted to common stock)</link:label>
    <link:label id="lab_us-gaap_WarrantMember_label_en-US" xlink:label="lab_us-gaap_WarrantMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Warrant [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WarrantMember" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_WarrantMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WarrantMember" xlink:to="lab_us-gaap_WarrantMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_StandardPoorsAPlusAAMinusRatingMember_b540b633-34ec-4aa7-b965-a19bc14b8d3f_terseLabel_en-US" xlink:label="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">A+, A, A-</link:label>
    <link:label id="lab_root_StandardPoorsAPlusAAMinusRatingMember_label_en-US" xlink:label="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, A Plus, A, A Minus Rating [Member]</link:label>
    <link:label id="lab_root_StandardPoorsAPlusAAMinusRatingMember_documentation_en-US" xlink:label="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Standard &amp; Poor's, A Plus, A, A Minus Rating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_StandardPoorsAPlusAAMinusRatingMember" xlink:href="root-20211231.xsd#root_StandardPoorsAPlusAAMinusRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_StandardPoorsAPlusAAMinusRatingMember" xlink:to="lab_root_StandardPoorsAPlusAAMinusRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission_c1f7969f-f5e5-4624-acf0-9d51d4a2039f_terseLabel_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Provision for sliding scale commissions</link:label>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission_label_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Provision For Sliding Scale Commission</link:label>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission_documentation_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Provision For Sliding Scale Commission</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission" xlink:href="root-20211231.xsd#root_ReinsuranceRecoverableProvisionForSlidingScaleCommission"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission" xlink:to="lab_root_ReinsuranceRecoverableProvisionForSlidingScaleCommission" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_6066fb44-30b6-4400-b867-c145e6f9d2ad_terseLabel_en-US" xlink:label="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total share-based compensation expense</link:label>
    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_label_en-US" xlink:label="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Payment Arrangement, Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllocatedShareBasedCompensationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_AllocatedShareBasedCompensationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllocatedShareBasedCompensationExpense" xlink:to="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ResearchMember_5b63dc89-b395-4419-8b71-0dae4f20835c_terseLabel_en-US" xlink:label="lab_us-gaap_ResearchMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Research and development costs</link:label>
    <link:label id="lab_us-gaap_ResearchMember_label_en-US" xlink:label="lab_us-gaap_ResearchMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Research Tax Credit Carryforward [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResearchMember" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_ResearchMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ResearchMember" xlink:to="lab_us-gaap_ResearchMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForLossCorridor_cbc6fec7-43be-478d-8b96-b10b471f6d50_terseLabel_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Provision for loss corridor</link:label>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForLossCorridor_label_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Provision For Loss Corridor</link:label>
    <link:label id="lab_root_ReinsuranceRecoverableProvisionForLossCorridor_documentation_en-US" xlink:label="lab_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Provision For Loss Corridor</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:href="root-20211231.xsd#root_ReinsuranceRecoverableProvisionForLossCorridor"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:to="lab_root_ReinsuranceRecoverableProvisionForLossCorridor" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_07517349-1b7d-4cd5-be32-74a97704f61e_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments [Domain]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:to="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock_2b430d14-8419-4faf-8042-b8ed193eedcd_terseLabel_en-US" xlink:label="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of capitalized computer software</link:label>
    <link:label id="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock_label_en-US" xlink:label="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule Of Capitalized Computer Software [Table Text Block]</link:label>
    <link:label id="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock_documentation_en-US" xlink:label="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule Of Capitalized Computer Software</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:href="root-20211231.xsd#root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:to="lab_root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_root_ConversionOfStock_78eeda74-3be7-41df-be84-8eacf1a84714_terseLabel_en-US" xlink:label="lab_root_ConversionOfStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of Stock</link:label>
    <link:label id="lab_root_ConversionOfStock_label_en-US" xlink:label="lab_root_ConversionOfStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of Stock</link:label>
    <link:label id="lab_root_ConversionOfStock_documentation_en-US" xlink:label="lab_root_ConversionOfStock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion of Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_ConversionOfStock" xlink:href="root-20211231.xsd#root_ConversionOfStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_ConversionOfStock" xlink:to="lab_root_ConversionOfStock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonClassAMember_8e5e0618-4e0a-4833-a6c8-a4b427e4d45f_terseLabel_en-US" xlink:label="lab_us-gaap_CommonClassAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Class A Common Stock</link:label>
    <link:label id="lab_us-gaap_CommonClassAMember_label_en-US" xlink:label="lab_us-gaap_CommonClassAMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Class A [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonClassAMember" xlink:href="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd#us-gaap_CommonClassAMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonClassAMember" xlink:to="lab_us-gaap_CommonClassAMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_4e3eda34-6f63-4ccb-92e2-4bb0162ea7fd_periodStartLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash, cash equivalents and restricted cash at beginning of year</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_bccc2c53-f955-47dd-92ba-9646d8128cfc_periodEndLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash, cash equivalents and restricted cash at end of year</link:label>
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