On New Year’s Eve 1990, I was 14 years old, standing outside a club in Manhattan with a VIP ticket in my hand that might as well have said “this kid does not belong here.” My black-on-black outfit was carefully calculated, sleeves rolled to just the right fold, and my suede Dr. Martens had seen maybe one other party: my friend’s bar mitzvah. I was freezing, faking, and fully convinced that if I didn’t get into that club, my life would be over.
That night, I got in. Barely. And that moment — that freezing, awkward, exhilarating, low-key fraudulent moment — is when I learned something I’ve carried through every business I’ve built and every founder I’ve backed:
Success is just getting past velvet ropes over and over again.
More …
You’re more likely to be struck by lightning. You’re more likely to be eaten by sharks. You’re more likely to score a royal flush in your first hand of poker. And on and on it goes. Basically, it’s scientifically proven that playing the lottery is a waste of money. So... why do it?
Every week, I play the lottery, and I have for years. I don’t plan on breaking this habit, either, even though I know that it’s essentially statistically impossible for me to win, and so the $2 I spend is a loss from the get-go. I’ve gotten some strange looks from friends and others when they find out I play or notice the tickets in my wallet. People are often surprised, and in some cases, disapproving-- playing the lottery has something of a taboo about it!
But for me, it’s not about the odds that I might not win-- it’s about the fact that I definitely can’t win if I don’t play. Let me explain ….
