The Asshole Bet

Silicon Valley rewards taking what isn't yours. So let's price the bet honestly.

My Take:

I promoted a guy into a consequential role at the exact moment he’d privately decided to leave. He took the job anyway, purely as leverage: a fresh title to wave at his next employer while he was already halfway out our door.

It put me in a shitty spot too, but who feels bad for the boss. The people he actually torched were his own team, the ones who’d just handed him the mantle. He took the trust they gave him, slid it across the table, and let it ride. I’ve been chewing on it for weeks.

A friend of mine wasn’t having my outrage. “I’m not sure this guy’s as dastardly as you’re making him,” he said. “He probably just looked around Silicon Valley and clocked that the people who end up on the cover of Time are the ones who only ever think about themselves.”

He’s right, of course. A lot of the people we put on magazine covers out here got there by taking what wasn’t theirs and stepping over whoever was in the way. So when some young buck watches who gets rewarded and who gets buried and decides the move is to be a shark, I’m not going to insult him with a sermon about doing the right thing. He’s been paying attention. My sermon doesn’t match the scoreboard, and he spots the dissonance. Maybe that’s why Silicon Valley is saturated with pioneers who’ve concluded that the smart move is to claw at all the chips on the table and never look back.

So let’s take that seriously instead of bemoaning it. If being an asshole is really the winning move, then it’s a bet, and a bet can be priced. Let’s price it honestly.

To do that, we’re going to borrow a concept you meet in the first week of a computer science degree: the greedy algorithm. It’s the dumbest algorithm there is. It optimizes for the next step and only the next step, grabs whatever looks biggest right in front of it, and never lifts its head to see the shape of the curve it’s climbing. Sometimes that works. Mostly it marches you up a little hill while the mountain sits untouched two valleys over.

Take-take-take is a greedy algorithm in a Patagonia vest. It optimizes the next raise, the next title, the next exit, and never once goes to the balcony to look at the whole game.

And the whole game is where the bet falls apart.

You only ever hear about the bullies and brutes who made it. Jobs. Musk. Ellison. Bezos. The handful whose ruthlessness got rewritten after the fact as vision. Who you never meet is the enormous pile of people who ran the identical play and are now doing thought leadership on LinkedIn. Nobody writes the oral history of the guy who was sure he was special and turned out to be a jerk with an impressive résumé and zero references. That’s survivorship bias, and it’s the engine of the whole delusion. The kid is studying lottery winners and copying the part where they bought a ticket.

Because the ruthlessness was never what worked. The talent was, and the ruthlessness just got tolerated because the talent was already in the room.

Reed Hastings put the cleanest name on this years ago in the Netflix culture deck: the brilliant jerk. His point was that in a big enough company brilliant jerks do occasionally punch through, and they get tolerated, because every so often they can do a specific thing nobody else on earth can do. That’s the entire deal. The jerk tax gets waived for exactly one reason, and it isn’t charm.

Which leaves one question, and it has nothing to do with your soul. Are you really that brilliant? Be honest, because the whole bet is riding on the answer, and the house has already seen your cards.

I’ve been hiring people for a couple of decades, and I’ve watched the brilliant-jerk bet flame out far more often than it pays. The ones who paid the tax and got nothing back don’t end up on covers. They just stop getting the call.

And even the winners pay a bill the highlight reel edits out. Steve Jobs backdated stock options. Flatly illegal. He walked, because Jobs was a national treasure and the rules bend for national treasures. We forget he also got thrown out of his own company once. The bill always comes due. For the geniuses it comes due late and quiet. For everyone else it comes due on schedule, with interest.

And even winning is thinner than it looks. Being a brilliant jerk is a lonely way to live. Win the whole bet and you get to spend the winnings surrounded by sycophants, people there for the wealth and the proximity who’d be gone the morning it dried up. Lose it and the story is just drab, because now you can’t pull a reference to save your life, or your mortgage. Either way you end up holding the influence and none of the people. Power and money and no real friends to share it with has never looked much like success to me.

Which brings me back to the guy who’s had me chewing. My friend was right that he’s probably not a villain. He just ran the play he watched everybody else get rich running. But the play is a greedy algorithm, and he is no Steve Jobs. He cashed a chip that was worth far more held than played, and the people he stiffed on the way out are the same ones whose phone calls will decide his next ten years. If you have to burn people to get to the next thing, the talent isn’t carrying you on its own, and somewhere under the swagger you already know it.

The young buck read the scoreboard right. He just misread what it counts. The sharks who win are rarer than the covers make them look, and they win a life surrounded by people who’d scatter the morning the money did. Everyone else making this bet spends their one chip of borrowed trust and then spends the next decade wondering why the phone went quiet. Both endings are lonelier than the cover story lets on.

If people trust you and enjoy working alongside you, your odds of success go up. Fittingly, those are also the soil conditions for a much happier life.