United States securities and exchange commission logo





                              October 1, 2020

       Alexander Timm
       Chief Executive Officer
       Root Stockholdings, Inc.
       80 E. Rich Street, Suite 500
       Columbus, Ohio 43215

                                                        Re: Root Stockholdings,
Inc.
                                                            Amendment No. 1 to
Draft Registration Statement on Form S-1
                                                            Submitted September
17, 2020
                                                            CIK No. 0001788882

       Dear Mr. Timm:

             We have reviewed your amended draft registration statement and
have the following
       comments. In some of our comments, we may ask you to provide us with
information so we
       may better understand your disclosure.

              Please respond to this letter by providing the requested
information and either submitting
       an amended draft registration statement or publicly filing your
registration statement on
       EDGAR. If you do not believe our comments apply to your facts and
circumstances or do not
       believe an amendment is appropriate, please tell us why in your
response.

             After reviewing the information you provide in response to these
comments and your
       amended draft registration statement or filed registration statement, we
may have additional
       comments.

       Amendment No. 1 to Draft Registration Statement on Form S-1

       Cover Page

   1.                                                   We note your disclosure
on page 12 and elsewhere that each share of Class B common
                                                        stock has ten votes per
share. Please update the cover page to reflect this voting right.
       Prospectus Summary, page 1

   2.                                                   We note your response
to our prior comment 4 and reissue in part. Please provide support
                                                        for the following
statements or revise to make it clear these are management   s beliefs:
                                                            Traditional methods
of risk assessment are imprecise and not personalized
                                                            Systems and
processes are typically old and disconnected from the needs of
                                                             consumers
 Alexander Timm
FirstName  LastNameAlexander Timm
Root Stockholdings, Inc.
Comapany
October    NameRoot Stockholdings, Inc.
        1, 2020
October
Page 2 1, 2020 Page 2
FirstName LastName
                Behavioral data is generally underutilized and agents are the
primary form of
              distribution.
3.       Please balance the disclosure in your summary, which highlights what
you believe are
         your competitive advantages, to discuss the potential challenges you
face as it relates to
         your competitive position. In this regard, we note your disclosure on
page 78 that you
         are challenged by traditional insurers who have more diverse product
offerings and longer
         established operating histories, and that these competitors can mimic
certain aspects of
         your digital platform and offerings and can offer customers the
ability to bundle multiple
         coverage types together. We also note your disclosure on page 113 that
your competitors
         include large national insurance companies, as well as up-and-coming
companies and new
         market entrants in the insurtech industry, some of whom also utilize
telematics and offer
         forms of usage-based insurance, and that several of these companies
are larger and have
         significant competitive advantages over you, including increased name
recognition, higher
         financial ratings, greater resources, additional access to capital,
and more types of
         insurance coverage to offer.
4.       We note your response to our prior comment 7 and reissue in part.
Consistent with your
         disclosure on page 106, please disclose on pages 2 and 95 that
adjusting for policies that
         do not make it through the underwriting period and rescissions reduces
one and two term
         policy retention by 33% and 10%, respectively.
5.       We note your response to our prior comment 9 and reissue in part.
Please reconcile your
         graphic on page 3 showing that total accident periodloss ratio
declined from 110% in
         FY2018 to 100% in FY2019, with your disclosure on page 17 that the
direct loss ratio
         increased from 93.6% in FY2018 to 99.9% in FY2019, or advise.
The COVID-19 pandemic has caused disruption to our operations, page 20

6.       We note your response to our prior comment 12 and reissue in part.
Please revise to
         describe in greater detail whether and to what extent you have been
impacted by
         the various mandates and requests of state regulators in response to
COVID-19.
Management's Discussion and Analysis of Financial Condition and Results of
Operations
Capital Management, page 72

7.       We acknowledge your response to prior comment 16 and your revised
disclosure on page
         73 as well as that on page 112. Please tell us the nature of your
insurance-linked security
         used in your capital management and reinsurance strategies effective
July 1, 2020 and
         why you believe that it is innovative. In your response tell us:
             The type of security (e.g., a bond not repayable if some insurance
event occurs or
             does not occur, catastrophe bond, etc.);
             The significant provisions of this security;
             How you intend to account for this security including reference to
the authoritative
             literature you rely upon to support your intended accounting; and
             Whether this security is a material contract under Item 601(b)(10)
of Regulation S-K
 Alexander Timm
FirstName  LastNameAlexander Timm
Root Stockholdings, Inc.
Comapany
October    NameRoot Stockholdings, Inc.
        1, 2020
October
Page 3 1, 2020 Page 3
FirstName LastName
              and explain why or why not.
Key Performance Indicators, page 73

8.       We note your response to prior comment 17. Please revise to disclose
your reasons for
         providing direct written and direct earned premiums consistent with
your response.
Critical Accounting Policies and Estimates
Reinsurance, page 92

9.       We note your response to prior comment 36. Please revise your
reinsurance disclosure
         further to quantify and explain the significant 2019 increases in your
provisions for each
         feature, and their resulting impacts to your financial statements and
liquidity.

Our Products, page 107

10.      We note your response to our prior comment 3. Please disclose the
material terms of
         the acquisition agreement and file the agreement as an exhibit or tell
us why you believe
         that is not required.
Description of Capital Stock
Voting Rights, page 141

11.      Please disclose the percentage of outstanding shares that Class B
shareholders must
         maintain to continue to control the outcome of matters submitted to
shareholders for
         approval.
Conversion, page 142

12.      We note your disclosure regarding conversion of the Class B common
stock. Please
         describe the dilutive impact of such conversion upon the outstanding
shares of Class A
         common stock.
Notes to the Consolidated Financial Statements
Note 5: Loss and Loss Adjustment Expense Reserves, page F-17

13.      We acknowledge your response to prior comment 35. Please tell us how
your current
         presentation of your loss development table on page F-18 complies with
the guidance in
         ASC 944-40-50-4B to present only losses and allocated loss adjustment
expenses (LAE).
         In this regard, for example, it appears that your 2019 accident year
incurred amount
         presented in the table of $295.0 million is composed of $177.0 million
in claims paid and
         $118.0 million in unpaid claims as of December 31, 2019. As the $17.6
million in
         unallocated LAE identified in your response only relates to your paid
claims and you
         indicate essentially that your reserving approach includes both
allocated and unallocated
         LAE, it appears that the $118.0 million in unpaid claims included in
the incurred portion
         of your table includes unallocated LAE and is therefore inconsistent
with the referenced
 Alexander Timm
Root Stockholdings, Inc.
October 1, 2020
Page 4
         guidance.
        You may contact Bonnie Baynes at (202) 551-4924 or Mark Brunhofer at
(202) 551-
3638 if you have questions regarding comments on the financial statements and
related
matters. Please contact John Stickel at (202) 551-3324 or Justin Dobbie at
(202) 551-3469 with
any other questions.



FirstName LastNameAlexander Timm                           Sincerely,
Comapany NameRoot Stockholdings, Inc.
                                                           Division of
Corporation Finance
October 1, 2020 Page 4                                     Office of Finance
FirstName LastName