Diary from the War Stable: Alexis Ohanian of Reddit Talks Gambling, DerbyJackpot, and Churchill Downs

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John: What first sparked your interest in DerbyJackpot?

Alexis: I was blown away by the team + product at a SeatGeek tech+sports conference pitch competition I was judging. I not only voted for them at the contest (they won) but also ended up investing shortly thereafter.

John: Were you interested in horse racing as a kid?

Alexis: My grandpa has been handicapping the ponies for decades. He’s tried his best to get me into it, but I just didn’t have the patience for all the nuances and don’t exactly live near a track. Enter DerbyJackpot!

I’ve been known to place bets while working in a cafe, tabbing over to my DerbyJackpot window when the bell is about to go off.

John: What makes it stand out amongst other betting outlets?

Alexis: It’s so damn simple — a remarkably well-executed product.

John: What do you help advise the team on?

Alexis: Whatever they needed! I’m always good for some product, community, and marketing advice in particular, though. Fortunately, they’ve spent so much time thinking about the problem and the audience that there’s not a lot I need to do.

John: What’s your plan for the Derby?

Alexis: I’ll be in Talladega, Alabama watching from a bar, betting from my phone of course.

John: Any advice for those looking to bet?

Alexis: Wicked Strong! Find a horse that has an awesome name, then bet on it. Or if that doesn’t work for you, pick the jockey with most badass story.

Alexis Ohanian is a tech entrepreneur, and a co-founder of the immensely popular site, Reddit. His book, Without Their Permission, is a WSJ bestseller; catch him talking about it on The Colbert Report and Charlie Rose.

John Surico is a writer based in New York. His reporting can be seen in the New York Times, the Wall Street Journal, the Village Voice, Narratively, and other places. He also hails from Floral Park, home of the Belmont Stakes. So he’s seen it all.