Ask A VC — Ezra Galston, Senior Associate at Chicago Ventures

by Elizabeth Galbut (@design4innov8)

“Ask A VC” is an interview series by SoGal Ventures, featuring prominent venture capitalists around the world. We hope to inspire diversity in the tech community — empowering our generation to grow into exceptional entrepreneurs and investors.

Tell us a bit about yourself:

Ezra Galston: Hiya! I’m Ezra, an investor at Chicago Ventures which is undeniably (according to my mom) the coolest VC firm in the Midwest. Every VC will tell you they have an unorthodox path to venture, but I actually have a pretty orthodox path as I went to Rabbinical School before venture. In all seriousness, I started my career in marketing as Director of Interactive Marketing for a Millenial/GenZ (I think we were just called “youth” back then) marketing agency called Buzz Marketing Group working in the entertainment industry.

When I got exhausted of that I played poker for a living for several years, splitting my time between online poker and high stakes games across the globe. In 2007, I joined my friends Taylor & Andrew to help build CardRunners, a subscription-based training platform for poker players and where I led marketing efforts. At CardRunners, we later acquired Hold’em Manager, a software analytics platform, and then launched DraftDay, which was one of the largest Daily Fantasy Sports sites until its acquisition by MGT Capital (NYSE: MGT) in 2014.

I went to business school at Chicago Booth and found myself in VC mostly by accident via an internship through my school’s PE/VC lab way back in 2011. But I’d made some angel investments before school, and I think my team appreciated that I’d incinerated my own money as an angel, rather than learning on their dime, so they made me an offer I couldn’t refuse.

What you need to know about Chicago Ventures is that if you do literally anything that touches brands we should be one of your first calls. A third of the entire Fortune500 is in the Midwest. We have strong relationships across teams from CMOs to CHROs with the big box retailers, CPGs, financial firms, insurance firms, you name it. We have deep backgrounds in e-commerce, adtech, marketing technology, enterprise SaaS, and of course building liquid markets.

Oh, and my blog is BreakingVC. Join the mailing list for some high quality spamming!

What’s one piece of advice you received about being a VC, that you’ve now realized is completely wrong?

I was told I’d never be able to make a career out of it and that I wouldn’t be successful. By no means am I anywhere near a success, but I’ve been at Chicago Ventures for 3.5 years which is the longest I’ve ever held down a job by a solid 18 months, so by my standards, that’s a “career.”

What role does professional relationships play in deal flow? Have you gotten to invest in any awesome deals because of relationships you built during your time as a UChicago MBA?

Totally. I became friends with David Daneshgar (co-founder of Bloomnation) at UChicago and he let me invest in their Seed & A rounds. He claims it’s because I did most of his homework for two years, but I don’t remember it that way. Or at least that’s what I told the Dean.

But relationships are everything in this biz. If people don’t like you, it doesn’t matter how many Twitter followers you have. Well, actually, maybe it does…I don’t have that many followers so I guess I wouldn’t know anyway.

From a strategic level, VC is in no small part a game of missing information. Professional relationships — with other VCs, in industries, other entrepreneurs, etc — enable you to start to chip away at the information asymmetry.

Whether it’s getting a better sense of who a founder is, challenging their assumptions, speaking to customers, the more relationships you have, the better. That’s why I spend so much of my life actually meeting with people instead of grinding at a computer.

You’re currently a Senior Associate at a mid-sized VC firm in Chicago. What are some of your favorite things about your role? Anything you really dislike doing, despite it being necessary?

I love the people I work with: Stuart, Kevin, Jason, Lindsay and Peter. I love that I get to go deep, study different industries and develop independent passions and theses.

When I was trying to learn about bitcoin back in 2013, I basically walled myself in an office for 2 weeks, taught myself how to mine, got active on BitcoinTalk, and talked to no one in the real world. I emerged two weeks later with an unruly beard, but also an authentic understanding of the technology, the culture and its players. I can’t imagine any other job you could do that.

There’s nothing I dislike about the role. But it is not an easy job. I like to say that being a founder is multiples harder than a VC, but, even so, this industry is cutthroat and one where I’m competing with legitimately some of the most brilliant thinkers in the world. It’s just a scary proposition. And it’s a job where you feel like you’re never doing enough. I wrote about that here and am working on being less hard on myself.

Your blog BreakingVC is absolutely fantastic. What are some words of wisdom you can pass on to other VCs and entrepreneurs who are thinking of starting to blog?

Thanks! I’ve started to get asked this a lot. I blog because I love writing. I blogged when I played poker, I blogged when I was at CardRunners, I blogged when I moved to Israel, I blogged when I went to business school…all told, I’ve been blogging for 12 years. (I actually blogged in high school, but I deleted that Livejournal account…did I just date myself?)

My biggest recommendation is to be genuine and authentic about who you are and how you present yourself. The people in this industry are both downright brilliant and have killer instincts — they can spot people who are fakers from a distance.

I am a bit emo and silly and so my blogs and interviews are a bit emo and silly. What you see is what you get.

I think that if how you communicate to the world is who you really are, then, at a minimum, people will respect you for it.

How do you see Venture Capital as an industry changing in the next ten years?

Sorry, I’m simply not smart enough to know. I’ve been in the biz for four years, let’s leave it to the experts who’ve lived through multiple cycles.