Page 1

trupanion ™ Medical insurance for the life of your pet . Exhibit 99.1 Trupanion Reports Second Quarter 2021 Results SEATTLE , WA . August 5 , 2021-- Trupanion , Inc. ( Nasdaq : TRUP ) , the leading provider of medical insurance for cats and dogs , today announced financial results for the second quarter ended June 30 , 2021 . " Q2 was another great quarter with net pet growth up 60 % year - over - year , led by exceptionally strong retention rates , ” said Darryl Rawlings , founder and chief executive officer of Trupanion . Second Quarter 2021 Financial and Business Highlights • Total revenue was $ 168.3 million , an increase of 43 % compared to the second quarter of 2020 . • • • Total enrolled pets ( including pets from our other business segment ) was 1,024,226 at June 30 , 2021 , an increase of 38 % over the second quarter of 2020 . Subscription business revenue was $ 120.4 million , an increase of 30 % compared to the second quarter of 2020 ( 27 % on a constant currency basis ) . Subscription enrolled pets was 643,395 at June 30 , 2021 , an increase of 22 % over the second quarter of 2020 . Net loss was $ ( 9.2 ) million , or $ ( 0.23 ) per basic and diluted share , compared to net income of $ 1.4 million , or $ 0.04 per basic and diluted share , in the second quarter of 2020. Net loss per share was impacted by $ 0.11 due to an increase in stock - based compensation and by $ 0.04 due to an increase in depreciation and amortization when compared to the prior year period . The remaining year - over - year change in earnings per share primarily reflects our accelerated growth and associated acquisition spend in the second quarter of 2021 . Adjusted EBITDA was $ 0.2 million , compared to adjusted EBITDA of $ 5.5 million in the second quarter of 2020 . Operating cash flow was $ ( 2.2 ) million and free cash flow was $ ( 5.1 ) million in the second quarter of 2021. This compared to operating cash flow of $ 4.9 million and free cash flow of $ 3.1 million in the second quarter of 2020 . First Half 2021 Financial and Business Highlights • Total revenue was $ 322.9 million , an increase of 41 % compared to the first half of 2020 . • • Subscription business revenue was $ 233.7 million , an increase of 28 % compared to the first half of 2020 . Net loss was $ ( 21.7 ) million , or $ ( 0.54 ) per basic and diluted share , compared to net income of $ 0.2 million , or $ 0.01 per basic and diluted share , in the first half of 2020. Net loss per share was impacted by $ 0.28 due to an increase in stock - based compensation and by $ 0.08 due to an increase in depreciation and amortization when compared to the prior year period . The remaining year - over - year change in earnings per share primarily reflects our accelerated growth and associated acquisition spend in the first half of 2021 . Adjusted EBITDA was $ ( 0.9 ) million , compared to adjusted EBITDA of $ 7.5 million in the first half of 2020 . Operating cash flow was $ ( 3.9 ) million and free cash flow was $ ( 9.7 ) million in the first half of 2021. This compared to operating cash flow of $ 7.8 million and free cash flow of $ 4.5 million in the first half of 2020 . 1