Ezra Galston: From Poker Player To Chicago’s Fastest Rising VC

Colin Keeley

Ezra Galston is a VC at Chicago Ventures. At CV, Ezra focuses on consumer facing investment and is actively involved with BloomNation, Kapow Events, Luxury Garage Sale, Shiftgig, SpotHero, Zipments, and Havenly. He writes one of my favorite VC blogs at BreakingVC.com and his thoughts on startups have also been published in the Wall Street Journal, TechCrunch, VentureBeat, and Re/code. Before becoming a venture capitalist, Ezra was a professional poker player and the Director of Marketing for CardRunners Gaming.

In this episode, we touch on, how Ezra got into angel investing, what motivates Chicago Ventures, what the one question every founder should ask of their VCs, and why Ezra prefers growing a business over starting one. Plus we'll also talk about where he sources his investments from, why producing content as a VC is important, how they look for outliers in the entrepreneurs they back, and how he finds and cultivates his mentors.

After all that, he discuss why Ezra thinks ecommerce companies are underestimated, what Ezra wishes he knew when he first got into the venture industry, why some venture capital investments never get announced, why he thinks Chicago is so good at building great business, and hat we can do to make Chicago even better for startups.

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Colin Keeley is the founder and host of Tech In Chicago, an independent podcast with interviews from Chicago’s top startup founders and venture capitalists.