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. 

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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:

• The Little Prince by Antoine de Saint-Exupéry
• Ayn Rand
• Sweet Pickles by Richard Hefter

• Seeing What Others Don't: The Remarkable Ways We Gain Insights by Gary Klein

E-Commerce Companies:

• Stitch Fix
• Trunk Club
• Wayfair
• Zulily

Investors Ezra Admires:

• Bill Gurely, VC at Benchmark
• Fred Wilson, VC at Union Square Ventures
• Brad Feld, VC at Foundry Group
• Stuart Larkins, VC at Chicago Ventures

Miscellaneous Things Mentioned: 

• Taylor Caby, founder of CardRunners
• Chris Fargis, founder of Instant Fantasy Sports 
• John Tough, COO at Choose Energy
• Report Says Chicago Has the Highest Percentage of Female Entrepreneurs
• The Little Prince (2015 film)
• The Counterintuitive Thing About Counterintuitive Things by Startup L. Jackson
• Tilt (poker term)
• The Big Short (2015 film)
• Dear Brad, Fred & Mark: How The Hell Do You Do It? by Ezra Galston