SecProbe.io

March 28, 2014

Via E -mail
Darryl Rawlings
Chief Executive Officer
Trupanion, Inc.
907 NW Ballard Way
Seattle, WA 98107

Re: Trupanion, Inc.
Confidential Draft Registration Statement on Form S -1
Submitted February 28, 2014
  CIK No. 0001371285

Dear Mr. Rawlings :

We have reviewed your 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 registra tion statement or filed registration statement,  we may have  additional
comments.

General

1. We note that you have yet to submit several of your exhibits. Please be advised that  we
may have further comments upon examination of these exhibits once they
have  been submitted by amendment.

2. Please provide us proofs of all graphic, visual or photographic information you
will provide in the printed prospectus prior to its use, for example in a preliminary
prospectus. Please note that we may have comments regarding  this material.

3. Please supplementally provide us with copies of all written communications, as
defined in Rule 405 under the Securities Act, that you, or anyone authorized to do

Darryl Rawlngs
Trupanion, Inc.
March 28, 2014
Page 2

 so on your behalf, present to potential investors in reliance on Section 5(d)  of the
Securities Act, whether or not they retain copies of the communications.
Similarly, please supplementally provide us with any research reports about you
that are published or distributed in reliance upon Section 2(a)(3) of the Securities
Act of 1933 added by Section 105(a) of the Jumpstart Our Business Startups Act
by any broker or dealer that is participating or will participate in your offering.

Prospectus Summary
Our Company, page 1

4. Please reconcile your statements pertaining to member loyal ty and your 98.5% monthly
retention rate with the statement on page 58 that only 56% of the pets enrolled in 2010
remained enrolled at the end of 2013.

5. Please provide the basis of your statement that you have “pioneered a unique solution,”
particularly si nce you note elsewhere in your disclosure that there are other pet insurance
providers that you are competing against.

6. Please expand the discussion to define how you use the term “retention rate” and clarify,
if true, that this term does not indicate the  percentage of specific individual members
enrolled at the beginning of a period who remained enrolled at the end of the period.  In
this regard, we note the presentation on page 58 indicates that the monthly retention rate
for the 2010 cohort increased fr om 97.14% at the end of 2010 to 99.07% at the end of
2013, while the number of enrolled pets in this cohort decreased form 34,583 in 2010 to
19,267 at the end of 2013.

7. Please note here that Territory Partners are  compensated by you on a commission basis.

8. In addition to your monthly retention rate, please indicate here what your cohort retention
rate over a year -to-year period has been, similar to the disclosure in your MD&A on page
58.

Our Solution, page 3

9. Please provide examples of the types of cl aims that are covered as well as those that are
not covered by your medical plan.

Risks Affecting Us, page 6

10. Please include in this list of material risks the possible inability to maintain effective
internal controls over financial reporting, as descri bed in the risk factor on pages 25 -26,
and note that a material weakness was identified by your independent auditor during
fiscal years 2010 -2012.

Darryl Rawlngs
Trupanion, Inc.
March 28, 2014
Page 3

 11. Please include in this list your current level of indebtedness and its possible impact on
your operations and the necessity of generating sufficient cash flow to satisfy your debt
service obligations, as described in the risk factor on pages 30 -31.

12. Please include in this list the possibility that litigation or regulatory action could
negatively impact your business, while citing the pending inquiries from Washington
State’s and California’s insurance agencies as described in the risk factor on page 31.

13. In your first bullet point, please include the net losses you have experienced over the last
three fiscal years as well as your accumulated deficit to date.  Please also include your
accumulated deficit in the related risk factor on page 13.

14. In your si xth bullet point and in the related risk factor on page 15, please state the amount
of current reserves you have established for claims.

15. In your eighth bullet point, the related risk factor on page 33 -34 and the relevant
disclosure on page 93, please stat e the minimum amount of risk -based capital APIC is
required to maintain.

Risk Factors
Risks Related to Our Business and Industry
“If we are unable to maintain high member retention rates, our growth prospects and revenue
will be adversely affected,” page  14

16. In this risk factor, please include information about your cohort retention rate on a year -
to-year basis, similar to the disclosure included in your MD&A on page 58.

“We depend on key personnel to operate our business . . .,” page 23

17. Please identif y the other key executives or employees whose departure could result in a
material adverse event.

 “Our indebtedness could adversely affect our business and limit our ability to expand our
business or respond to changes . . .,” page 30

18. Please expand thi s risk factor to summarize the financial and non -financial covenants you
must comply with in connection with the Square 1 credit facility and note your
obligations under both the Square 1 credit facility and the PEPI Capital, L.P. term loan
are secured by substantially all of your assets.

“A downgrade in the financial strength rating of our insurance company may have an adverse
effect on our competitive position . . .,” page 33

19. Please revise this risk factor to include the names of the rating agencies th at review APIC
and the current financial strength ratings they have assigned to it.

Darryl Rawlngs
Trupanion, Inc.
March 28, 2014
Page 4

 Risks Related to Compliance with Laws and Regulations
“We will incur significantly increased costs and devote substantial management time as a result
of operating as a public company,” page 38

20. Please include in this risk factor the approximate amount you expect to spend to comply
with your annual reporting obligations.

Management’s Discussion and Analysis of Financial Condition and Results of Operations
Overview, page  55

21. Please expand the discussion to indicate whether and how the pet policies you write for
your “other” business differs from the policies offered for your subscription business.

Cohort Analysis, page 57

22. You disclose at the end of 2013, 19,267 or 56%, of the original 34,583 cohort pets
remained enrolled in your medical plan.   This disclosure appears to be inconsistent with
your tabular disclosure that average monthly retention for the 2010 cohort at the end of
2013 was 99.07%.  Please revise your disclo sure to reconcile the different percentages.

Liquidity and Capital Resources
Regulation, page 72

23. Please provide d isclosure of any known uncertainty related to the parent company’s
ability to service debt due to restrictions on the sub sidiary’s net asset s.  Include in your
disclosure the expected effect of insufficient or potentially insufficient statutory capital
and/or dividend restrictions on future financial position or results of operations  and
disclose the nature and amount of the restriction on sub sidiary’s  net assets .

Operating Cash Flows, page 73

24. Expand the disclosure to explain why accounts and other receivables increased from
December 31, 2012 to December 31, 2013 at a rate greater than the increase in revenue
and deferred revenue or tell us w hy you believe no additional disclosure is necessary.

Critical Accounting Policies and Significant Estimates
Stock -Based Compensation, page 74

25. Please  provide us an  analysis of each significant factor contributing to the difference , to
the extent that it is significant,  between the common stock fair value as of the most recent
valuation date and the estimated IPO price.

26. Refer to your disclosure on page 77 that i n connection with the preparation of your
financial statements for the year ended December 31, 2013, you re-evaluated the estimate
of fair value of your common  stock for financial reporting purposes .  Please revise your

Darryl Rawlngs
Trupanion, Inc.
March 28, 2014
Page 5

 disclosure to explain how the re -valuation of the fair value of your common stock solely
for financial reporting purposes was consi dered in the fair value of the underlying
common stock assumption used to estimate the fair value of the stock options granted in
2013.

27. Explain to us the factors that contributed to the increase in fair value of your common
stock of 54% in three months fr om $4.77 per share on August 2, 2013 to $7.35 per share
on November 7, 2013 and an increase in fair value of 17% from $7.35 per share to $8.64
per share on December 23, 2013.

Claims Reserves, page 78

28. Please expand your disclosure to quantify how much of the reserve is an estimate of
IBNR at each balance sheet date presented in the financial statements.

29. Please identify the key assumptions used in estimating your claims reserves and quantify
and present preferably in a tabular format the impact that reason ably likely changes in
these key assumptions may have on reported results, financial position and liquidity.

Business
General

30. Please include in this disclosure a discussion of your relationship with the unaffiliated
managing general agent, which current ly comprises your Other business segment.  In this
discussion, as well as in your risk factor on page 24 and the relevant portion of your
MD&A, please identify this agent , the agent’s territory,  and describe with specificity
your practice of writing polici es on its behalf.

31. Pursuant to Regulation 601(b)(10)(i) of Regulation S -K, please file your agreement with
this agent as an exhibit to your registration statement and provide a fuller description of
its material terms in this section.

Our Company and A pproach, page 80

32. Please expand the discussion to describe major policy exclusions, if any.

33. Please provide additional information relative to your business including a breakdown of
the animals covered, i.e. dogs and cats, life expectancy, and variables in  the
determination of premiums.

Darryl Rawlngs
Trupanion, Inc.
March 28, 2014
Page 6

 Sales and Marketing, page 87

34. Please expand the Territory Partners discussion to describe whether the geographic
regions covered by the Territory Partners cover the entire United States or the extent to
which coverage is not currently offered.

35. Please state here whether the agreements you have entered into with your Territory
Partners are based on a form agreement and have material terms that are substantially
similar to each other. If there is such a form agreement, pl ease file it as an exhibit
pursuant to Regulation 601(b)(10)(ii)(B) of Regulation S -K.

36. Please disclose here and in your MD&A on page 60 the aggregate amount of
commission s you have paid to your Territory Partners over the last three fiscal years.

Lega l Proceedings, page 95

37. Please describe the alleged violations concerning APIC’s trial insurance policies raised
by the California Department of Insurance.

38. Please describe with further specificity the questions about proper licensure as well as the
allegations relating to producer licensing and appointments raised by the Washington
State Office of Insurance Commissioner.

Principal and Selling Stockholders, page 115

39. Please state in footnote 3 the name(s) of the individual(s) who hold voting and/or
investment power over the shares held by RenaissanceRe Ventures Ltd.

Restated Certificate of Incorporation and Restated Bylaws Provisions, page 122

40. We note your disclosure entitled Choice of Forum on page 123.  Several lawsuits are
currently challenging the validity of choice of forum provisions in certificates of
incorporation.  Please disclose that although you have included a choice of forum clause
in your restated certificate of incorporation, it is possible that a court could rule that such
provision  is inapplicable or unenforceable.

Shares Eligible for Future Sale
Lock -Up and Market Standoff Agreements, page 129

41. Please either file your form lock -up agreement as an exhibit or confirm that it will be
filed as an exhibit to the form underwriting agre ement.

Darryl Rawlngs
Trupanion, Inc.
March 28, 2014
Page 7

 Consolidated Financial Statements
Notes to Consolidated Financial Statements
8. Commitments and Contingencies , F-18

42. Refer to your disclosure of unpaid GST and HST taxes.  Please revise your disclo sure to
explain why self -reporting taxes for 20 07-2013 in 2014 will eliminate any penalties.

12. Preferred Stock and Stockholders’ Defici t
Warrants, page F -27

43. Please revise your disclosure to explain why the warrants are considered liability
instruments.  Also, you disclose that significant judgment is used in determining the
unobservable inputs used in valuing these instruments .  It appears that the valuation of
warrants is a critical accounting estimate.  Please revise the critical accounting policies
and significant estimates s ection of MD&A to include your accounting for warrants or
explain to us why disclosure in this section is not meaningful to investors.

If you intend to respond to these comments with an amended draft registration statement ,
please submit it and any associ ated correspondence in accordance with the guidance we provide
in the Division’s October 11, 2012 announcement on the SEC website at
http://www.sec.gov/divisions/corpfin/cfannouncements/drsfilingprocedures101512.htm .

Please keep in mind that we may publicly post filing review correspondence in
accordance with our December 1, 2011 policy
(http://www.sec.gov/divisions/corpfin/cfannouncements/edgarcorrespondence.htm ).  If you
intend to use Rule 83 (17 CFR 200.83) to request confidential treatment of inf ormation in the
correspondence you submit on EDGAR, please properly mark that information in each of your
confidential submissions to us so we do not repeat or refer to that information in our comment
letters to you.

Darryl Rawlngs
Trupanion, Inc.
March 28, 2014
Page 8

 You may contact Donald  Abbott  at (202) 551 -3608  or Lisa Vanjoske at (202) 551 -3614  if
you have questions regarding comments on the financial statements and related matters.  Please
contact Scot Foley  at (202) 551 -3383, John Krug at (202) 551 -3862 or me at (202) 551 -3715
with an y other questions.

Sincerely,

 /s/ Daniel Greenspan for

Jeffrey P. Riedler
Assistant Director

cc: Alan Smith
 James Evans
Amanda Rose
Fenwick & West LLP
1191 Second Avenue, Floor 10
Seattle, WA  98101