What You Can Learn About Business From Betting On Horses

A few of the champion gamblers on Esquire Network’s reality show Horseplayers share some tips that may also be applied to your work life.

Esquire Network’s Horseplayers, premiering Jan. 21, follows several professional gamblers across America’s racetracks as they vie for a spot—and the $1 million prize—in the National Thoroughbred Racing Association’s annual National Handicapping Championship taking place next week in Las Vegas.


Their wildly different strategies and insider secrets to picking the perfect pony have applications in investing and startup cultures. During the show taping at the Breeders’ Cup at Santa Anita Park in Arcadia, CA last fall, four of them shared the skills and mindsets gleaned from gambling that could translate to funding and staffing startups, managing employees and money, and making financial decisions. And if they don’t translate, well, you’ve picked up some tips for your next trip to the track.

Meet our horseplayer business advisors:

  • Kevin Cox–Dubbed the Brooklyn Cowboy, Cox is retired NYPD mounted police officer and former jockey agent who sports a cowboy hat. (Geek alert: His grandfather, DC Comics cartoonist Thomas DeAngelo, was the colorist for the original Superman comics).

  • John Conte–The 2009 National Handicapping champ (and seven-time qualifier) and former New York Post horse handicapping columnist, is the son of a Brooklyn bookmaker and started betting at 16.

  • Christian Hellmers–This digital startup entrepreneur (, DivX, Betfair) with a UCLA engineering degree brings a Southern California Zen quality and vegan lifestyle to the track. He placed second in the 2011 and 2012 Breeders’ Cub Betting Challenge.

  • Michael Beychok–The 2012 National Handicapping champion is a Baton Rouge, LA political consultant, who grew up betting horses with political heavyweight James Carville.
Veteran and 2009 champ John Conte

And here are some business tips they’ve leveraged from picking horses.


Christian Hellmers: “Invest in companies with or hire people who are highly-charged, positive individuals, because your emotional foundation is the key to your success. If you’re emotionally strong and fluid, you can roll with any set of circumstances.

[L-R] Zen master Christian Hellmers with his mother and betting partner, Georgia.

Keep emotion out of business decisions, and Invest for sustainability

Kevin Cox: “Horseracing is such an adrenaline-driven game–you could lose a race by a nose. On Wall Street, stocks are up and down by an eighth. When a myriad of variables can effect an outcome, you have to take emotions out of the mix. If you’re going to become a professional gambler and you’ve established a bankroll for yourself, there’s a certain train of thought that says never bet more than 5% of what you have invested. When you’re starting a business, you can’t over-invest initially. You have to leave a margin for error. If you bet too much and then have a cold streak, the next thing you know, you’ll be borrowing money to pay the rent.”

Michael Beychok: “There’s no get-rich-quick scheme. You have to learn your business. It took me a long time to learn how to gamble and manage the psychology. Just like in business, you can’t get too high or low over a sale, client, or a bad month, because it effects your decisions. It’s a long-term expectation game. It’s fun to get high off a win, but you can’t go back and shove all your money in the next race. In business, if you make a great sale, celebrate it, but don’t overleverage it the next month.”

Brooklyn Cowboy Kevin Cox

Picking stocks is like picking horses

Cox: “There are parallels to picking stocks and horses. Some people pick horses by handicapping in cycles. They read these reports called The Sheets that track the biorhythms of a horse, their ups and downs. People who invest in the stock market often look at the cycles of a company—the up-and-down arrow charts. They say it’s very hard for a horse to run two to three good races in a row. They peak, they plummet, and then they rally. That applies to the stock market–you don’t buy high, you buy low, when the stock is only going to improve. It’s the same thing with horseracing. You play a horse that’s going to improve.”

Beychok: “Horseracing is just like stocks in that it’s a buyer/seller’s game. I’m valuing this horse at this price, and some other person values it a lower price. If I’m right and he’s wrong, I’m going to make money, because I’m going to make the spread, and that’s the essence of value wagering.”

Political strategist and 2012 champ Michael Beychok

Diversify with other revenue streams

Conte: “I’m also a horse owner and breeder. When I won the half a million, I invested it into the thoroughbred industry. My horses won $200,000. Now you could look at it just like it was an accounting firm. It sounds great that my horse made $200,000, but if my bills are $400,000, I’m still $200,000 in the red. At that point, you either gotta cut down your expenses, or get a partnership with someone else who puts in money, or take from this jar to advance it to that jar. But if you’re taking too much from your other businesses to support the one that’s not working, it’s time to cut corners, and that’s the key to any business.”


Hellmers: “Horseracing takes up most of my time, but I have a couple of other businesses. One of them is a matchmaking company called The First Ten Minutes, which is more like horseracing than you might realize. Both love and racing involve analyzing hundreds of variables before you make a choice. It’s as much a science an art. I use a similar algorithm–some math, different variables, and some art–for matchmaking as I do for horseracing.”

Beychok: “My political consulting enables me to take breaks from horseracing, and refreshes my mind. The prime reason I’m doing the show is to leverage whatever`fake celebrity’ I have within this little niche of the industry and monetize it in the future through a website, where I sell picks, and a book I’m writing on my journey this year with some handicapping tips.”

Getting a pre-race polish.

Trust your Instinct and be ok with uncertainty

Conte: “Pay attention to body language and gut feeling. They put blinkers on horses, so they don’t get spooked. A lot of gamblers walk around with blinkers, like they’re in a bubble: `They won’t hurt me if I don’t know what’s going on.’ I’m six steps ahead of these executives who are giving me `cool’ and `dude’. There’s nothing more annoying to a street person than a bubble person.”


Beychok: “Some people are strictly data-driven, but it’s more of a feel-based game for me. I don’t handicap with computers. Your brain is your best supercomputer, so you gotta trust your instincts. As a political consultant, I’m trying to tell a client’s story. Here, I’m trying to look at what ‘story’ the race is telling me. While I am a numbers geek—in horseracing, there’s speed figures, health, pace, breeding, while political consulting at its core, is market research—it’s how you interpret those numbers. We can all look at the same pattern of numbers and come up with completely different opinions, which is what makes it a great investment or risk. If you’re right more than they are, you’re going to get paid more often.”

Hellmers: “When I have to make a decision, I assign the horses a probability range, which involves hundreds of variables. That’s the science. The other piece is art, which happens when you make a decision that forces you against the logic. I believe that the only way to win is to take colossal calculated risks, especially in tournaments. Often I have to defy the odds in a way that doesn’t require common, normal math—to earn a 500-900% return. If I’m comfortably uncomfortable, then I can do anything–allowing myself to feel the breadth of risk, make mistakes, and forgive myself. I realize the power that comes from taking a calculated risk with a certain success rate, then I listen to my intuition. People forget, this isn’t a science-only world. If it was, everything would be calculated and we’d know it all. But it isn’t designed that way on purpose, because we’re supposed to use some fuzziness and instinct in our decisions.”

Click on the slideshow for Horseplayer’s day at the races.


About the author

Susan Karlin, based in Los Angeles, is a regular contributor to Fast Company, where she covers space science and autonomous vehicles. Karlin has reported for The New York Times, NPR, Air & Space, Scientific American, IEEE Spectrum, and Wired, among other outlets, from such locations as the Arctic and Antarctica, Israel/West Bank, and Southeast Asia


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