CarGurus CFO Jason Trevisan has made some bold career moves, guided by a simple question: Am I happy?

Were you happy last month?

If the answer’s no, ask yourself why, and make a change.

My guest this week is Jason Trevisan, Chief Financial Officer of Boston-based IPO darling CarGurus. After funding itself for its first 8 years with less than $5 million of total venture capital, CarGurus took its $200 million business to the public markets in October at $16/share, raising $150 million customer acquisition war chest on the back of a $1.7 Billion enterprise valuation. After beating estimates for Q3, the stock sits today around $30/share, representing a market cap of over $3.2 Billion. To call their exit a home run would be a massive understatement, and Jason Trevisan was at the center of it.

This will be Jason’s first big interview since the end of their quiet period, and to set expectations we did NOT talk very much about the business. My focus as always was on Jason’s personal journey, which began at Duke and ran through Bain & Company, a stint at online advertising leader aQuantive until it was acquired by Microsoft, and an extended stay as a VC at Polaris Partners, a Boston VC firm focused on growth equity investments and buyouts in Internet, technology and healthcare. Jason is also a member of the board of directors of ShoeDazzle, Life Line Screening, PartsSource and Snappcloud.

Us, feeling good at a recent Mumford & Sons show.

Jason’s a close friend of mine, unique in having successfully crossed over between venture operating and investing roles at multiple points in his career. We’ll talk about that, discuss the relative strengths and weaknesses of both, and dig into the triggers anyone should be on the lookout for when deciding to make big changes in career trajectory. Jason uses something I call the “One Month Test” as a check on whether he’s on the right path, from both a career and life standpoint. The idea is that while anyone can have a bad day or even a bad week, at the end of each month you should take a moment to ask yourself whether you were happy in the month just passed, or not. If the answer is no, you should dig into why, and then make the changes you need to make to fix whatever problems are getting in the way of your own success.

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