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Originally known as Vetinsurance, Trupanion was founded in Canada by current chairman Darryl Rawlings in 1999.
Trupanion raised $22 million in 2007 from investors including Maveron, RenaissanceRe, and a large private equity group. Subsequently, a Series B round was completed in 2008, followed by a $9 million Series C round of financing led by the Highland Consumer Fund in 2011.
In 2014, Trupanion went public, raising $71 million during its initial public offering (IPO). The company continued its growth trajectory, culminating in October 2020 with the completion of a Private Investment in Public Equity (PIPE) funding round amounting to $200 million. By the end of the 2020 fiscal year, Trupanion reported revenue of $502 million.