TRUPANION, INC. — Director's Dealing 2014

Jul 17, 2014

SEC Form 3 — Initial Statement of Beneficial Ownership

Issuer: TRUPANION INC. (TRUP)
CIK: 0001371285
Period of Report: 2014-07-17

Reporting Person: Highland Consumer GP GP LLC (10% Owner)
Reporting Person: Highland Consumer GP Limited Partnership (10% Owner)
Reporting Person: HIGHLAND CONSUMER FUND I LP (10% Owner)
Reporting Person: HIGHLAND CONSUMER FUND I-B LP (10% Owner)
Reporting Person: HIGHLAND CONSUMER ENTREPRENEURS FUND I LP (10% Owner)

Holdings (Derivative)

Security	Exercise Price	Expiration	Underlying	Shares	Ownership
Series C Preferred Stock	$		Common Stock (3064240)		Indirect
Warrants to Purchase Common Stock	$	2018-12-23	Common Stock (59999)		Indirect

Footnotes

F1: The securities are held by Highland Consumer Fund I Limited Partnership ("Highland Consumer I"). Highland Consumer GP GP LLC ("HC LLC") is the general partner of Highland Consumer GP Limited Partnership ("HC LP"), which is the general partner of Highland Consumer I. Each of HC LLC and HC LP disclaims beneficial ownership of all shares held by Highland Consumer I except to the extent, if any, of such entity's pecuniary interest therein.

F2: The securities are held by Highland Consumer Fund 1-B Limited Partnership ("Highland Consumer IB"). HC LP is the general partner of Highland Consumer IB. Each of HC LLC and HC LP disclaims beneficial ownership of all shares held by Highland Consumer IB except to the extent, if any, of such entity's pecuniary interest therein.

F3: The securities are held by Highland Consumer Entrepreneurs' Fund I, Limited Partnership ("Highland Consumer Entrepreneurs"). HC LP is the general partner of Highland Consumer I. Each of HC LLC and HC LP disclaims beneficial ownership of all shares held by Highland Consumer Entrepreneurs except to the extent, if any, of such entity's pecuniary interest therein.

F4: Highland Consumer I is the holder of record of 2,460,396 shares of Series C Preferred Stock, Highland Consumer IB is the holder of record of 524,940 shares of Series C Preferred Stock and Highland Consumer Entrepreneurs is the holder of record of 78,904 shares of Series C Preferred Stock. The Preferred Stock will convert into Common Stock upon the closing of the Issuer's initial public offering on a one-for-one basis for no additional consideration and has no expiration date.

F5: Highland Consumer I is the holder of record of warrants to purchase 48,176 shares of Common Stock, Highland Consumer IB is the holder of record of warrants to purchase 10,278 shares of Common Stock and Highland Consumer Entrepreneurs is the holder of record of warrants to purchase 1,545 shares of Common Stock. In connection with the Issuer's initial public offering, the exercise price of the warrants is adjusted to $10.00 per share, which is price per share sold in the offering, and the warrants become immediately exercisable. In lieu of exercising the warrants, the holders thereof may convert such warrants, in whole or in part, into a number of shares determined by dividing (a) the aggregate fair market value of the shares issuable upon exercise minus the aggregate exercise price for such shares by (b) the fair market value of one share.