Lessons from the Belmont Stakes

On Saturday, June 9th 2018, the one hundred and fiftieth Belmont Stakes horse race will take place. When the race was founded in 1867, there were just thirty-seven stars on the flag of the United States and only a few weeks before the race, Alaska was purchased from Russia for $7.2 million dollars – roughly $0.02/acre.

The 1.5-mile race would only be interrupted by the Hart-Agnew Law of 1911 and 1912, anti-gambling legislation which forced a brief respite from vices; however, not even The Great War or World War II could halt the pounding hooves around the dirt track. Two minutes and twenty-four seconds is the record held by the Triple Crown legend Secretariat aka “Big Red” in 1973.

The Triple Crown, short for the Triple Crown of Thoroughbred Racing, is winning the Kentucky Derby, Preakness Stakes, and finally the Belmont Stakes. The feat has only been achieved 12 times throughout history and I was blessed to witness American Pharoah author history just a few years ago in 2015.

We find ourselves a few days away from this race and pageantry, and the specimen Justify may be poised to claim the illusive crown after a dominant performance at the Derby and a narrow win at the Preakness. Now come the odds makers, the mathematicians, the degenerates, and the gamblers…more concisely, my people.

How do you gamble on horse racing? Let’s rewind the story a bit and answer the first question you had – why does this clown like horse racing so much? My grandfather raced horses and even slept in the stables with them. As everyone knows, that’s what all the “real” horse trainers did…nothing to do with being in the catch-22 of needing to win the race to be able to afford lodging. I am not really sure how many races my Grandfather won. If you were to believe his children and grandchildren, a few of those twelve Triple Crown winners must have surely been his. What is probably more rooted in reality is the family lore of my Grandmother winning with paper slips as opposed to thunderous horseshoes.

Now is not the time to share all of the wisdom my Grandmother passed down to us, but I will repeat one gem she said often, that has found it’s way into common vernacular and has proven to be the foundation of a winning strategy popular among gamblers and investors alike– don’t bet on the horse, bet on the jockey.

Now horses are clearly important in a race, just like business ideas and strategy are important to a winning startup – but to hearken back to the wisdom of our matriarch –“for the horse to be in the race it must be good enough to be there.” Of course you need a racehorse to win a horse race, and of course you need a solid business idea to get traction with investors and VCs; however, there are more horses in the next stall and a line of entrepreneurs in the waiting room or at the coffee shop, chomping at the bit to show off their Secretariat or Justify.

Betting/investing in an early stage venture where all of the horses show promise frankly comes down to the jockey – sorry, those well-branded total addressable market slides didn’t quite seal the deal.

I have been fortunate in my career to assist in deploying and raising tens of millions of dollars, but nothing has been sweeter, humbling, and more rewarding than raising a fraction of those totals with the pictures of my co-founders and myself on the Team’s slide. Having seasoned investors bet on us to be their jockey and bring everyone to the Winner’s Circle is special.

Thank you to our first money in.

While I hope to witness another Triple Crown this Saturday, I’ll be rooting more for Mike Smith* than the horse.

*winner of the Kentucky Derby (2005 & 2018), Preakness Stakes (1993 & 2018), Belmont Stakes (2010 & 2013 & 2018?) – Geez I guess my Grandma was right!