Betting on the Jockey, Not the Horse.

I invest a lot more in the jockey than in the horse — Which means, I’m usually investing in the person and not necessarily their ideas or business. I take real stake in the fact that if I really believe in you, there’s a chance you might not win this one, but I want to be in your world for the second or third one.

I want to know your story. How did you get to this point? How did your idea and team come about? Why is your team structured the way it is? How is that going to affect your business moving forward? In essence, I’m investing in the unscalable — the humans behind it all.

A lot of people were pissed when they jumped off Ev Williams’ horse when they didn’t invest in Twitter after Odeo. Those that re-invested just knew what kind of person Ev was, and they invested in that notion more so than the product he was presenting. Take the girls from Birchbox. From our first meeting I knew that they would kill it. They had 60 nos before I said yes.

You can very well have a great product early on but there better be a portion of that business focused on actually driving results. You have to have the know-how and the chops to win business and to win people over. The sizzle must most definitely be there, but without the actual steak things just might not play out as planned. And so, the timing may just not always be right. The players might not be ready and/or the market may just not be aligned at that particular point in time. The only certainty I can really hedge is the potential that lies within the people pulling the strings behind the scenes.

I’m an optimist and I see the good in a lot of people, but the next place I look is the market and the markets I believe in. I believe the middle is in some deep sh*t. I look for startups that are solving human inefficiency. Uber, for example, sells time — and maybe more so, the perception of time. AirBnB sells time as well. So I’m looking for companies that sell time, or what I call “saw-dust,” the by products of solving human inefficiencies. These are the particular trends I’m looking for — The places where humans are flawed, where opportunities are presented, and can then be seized.

And so, you may have a great idea, but if you don’t have the chops as an individual to build a strong team and execute on your mission, then what good is it? I need assassins that are also nurturing and caring. I look for leaders and operators that can build sustainable businesses while also creating an environment that allows those around them to persevere with them. You very well may not win that first, second, or third race, but if you have the emotional intelligence and internal flame that I deem so incredibly valuable, then I am much more likely to put my money behind you, the jockey, than behind your horse, or business.

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