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From Professional Poker Player To Chicago's Fastest Rising VC - Ezra Galston / Chicago Ventures


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 You Will Learn:

  • How Ezra got into angel investing? 
  • What motivates Chicago Ventures?
  • What's the one question every founder should ask of their VCs?
  • Why Ezra prefers growing a business over starting one?
  • Where Ezra sources his investments from?
  • Why producing content as a VC is important? 
  • How they look for outliers in the entrepreneurs they back?
  • How Ezra finds and cultivates his mentors? Hint: cold emailing 
  • Why Ezra thinks e-commerce 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 Ezra thinks Chicago is so good at building great business? 
  • What we can do to make Chicago even better for startups? 

Favorite Books:

E-Commerce Companies:

Investors Ezra Admires:

Miscellaneous Things Mentioned: 

Sponsored By:

  • Bevy: a Chicago startup delivering everything you need, but don’t want to own, for amazing experiences. Own Less. Live More. 

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