The Quiet Things That No One Ever Knows

It's always been easy to feel invincible. I’ve been blessed in life: growing up in an upper middle class family, well connected, always a safety net to catch me if I fell. I met my extraordinary wife in a bar: all I had to do was say hello and sparks flew. I found online poker during an era when money literally grew on trees and won enough to basically finance the past decade of my life. I’ve worked hard – and I’ve hustled like hell – but I’ve been invincible: I got what I wanted. Sure there was volatility, but its been largely muted.

And then two months ago my friend Adam London, rising star in the Chicago tech community and all of 27 years old, simply never woke up. If only it were an isolated case. Six months prior, one of my wife’s closest friends woke up to find a lifeless husband, leaving behind a pair of 18-month old twins. Twins who will never have the opportunity to tell their father they love him.

It was a wake up call. We’re not invincible. And when things are stable, it’s so easy to forget and think we are. In reality, we’re constantly being humbled by life – it’s just that most of us are too obtuse to recognize it.

Concurrently, over the past few months I’ve been increasingly humbled in my venture career as well. Starting out, when you're largely reactive and responding to directives from superiors it's easy to do a good job - but as you take on more responsibility, mistakes become more frequent, and costly. Look, investors are really good at projecting strength and confidence – and that’s made easier by Twitter and short form content.  But I’ll just be honest: the last few months have been a struggle. I’ve failed myself and my firm on multiple occasions. There was a deal we should have won that we lost – and I was leading the charge. There was a company I should have been hawking over but was too lax – and they let some fundamental issues get out of hand. And there was a company we should have spotted and invested in, but I failed at selling my partnership properly both on upside and urgency and the opportunity slipped away.

Further, as one grows up in the venture business, structural constraints become increasingly relevant and incongruous. A mentor of mine once advised me that “venture is a terrible business for junior people.” The paradoxes are endless: any credible entrepreneur would prefer to work with your senior partner. And yet the goal is to become a senior partner. Any credible LP would prefer to talk to your senior partner. And yet the goal is to be a compelling fundraiser oneself.

Put it all together and it’s not hard to lose a bit of swagger and confidence.

When I was 19 and beginning to play poker at increasingly high stakes, I purchased and read Doyle Brunson’s classic instructional book Super System. Doyle is one of the winningest players in history, owner of multiple WSOP bracelets, and yet for years I always found the following section absolutely ridiculous:

After I've won a pot in No Limit ... I'm in the next pot regardless of what two cards I pick up. And if I win that one ... I'm always in the next one. I keep playing every pot until I lose one. And, in all those pots, I gamble more than I normally would.

If you don't play that way ... you'll never have much of a rush. I know that scientists don't believe in rushes ... but they make about fifteen hundred a month. I've played Poker for almost 25 years now ... and I've made millions at it. A big part of my winnings came from playing my rushes.

There's only one world class Poker player that I know of who doesn't believe in rushes. Well, he's wrong ... and so are the "scientists". Besides, how many of them can play Poker anyway?

If you want to take the money off ... I mean, make a big score ... then, you've got to play your rushes. It's that simple.

The section is absurd for all the obvious reasons. It’s absurd because it’s mathematically implausible. It’s absurd because subsequent hands are statisically uncorrelated to the ones prior. It’s absurd because it’s equivalent to the “hot hand fallacy,” in sports – which has, for all intents and purposes, been debunked.

And yet – in spite of those absurdities – it’s true.

Life is a series of streaks. Hot streaks. Cold streaks. Some simply too imperceptible to matter.

What’s underlying these (anecdotal) streaks? In poker, your opponents react to you differently. If you’re winning – and everyone knows it - your mere presence demands/manifests respect. Opponents make suboptimal decisions, allowing emotions to cloud their thinking. They will outlevel themselves, incorrectly assuming you're operating on a higher plane and lose sight of the reality in front of them.

In venture, success –whether due to innate brilliance or dumb luck - furthers brand which has the effect of enhancing network, reputation and trust. Failure cultivates the opposite. Both have material consequences.

I’ve always believed that the game of poker is a microcosm of life more boradly. And poker, like life, like venture, is a game of variance and swings. They key is remaining emotionally balanced and self-aware while building an authentic internal confidence and positivity. Never easy, always humbling - anything but invincible - but real.