Doug Leone told his dentist to drill without Novocaine.
He is 69, spent 26 years running Sequoia Capital, and has more money than he could spend trying. He had a root canal booked and a meeting straight after, and the dentist warned the anesthetic would leave his face slack and his speech thick. So he made a different call.
What lifts this above a flex is what Leone does for a living. He has spent forty years deciding which people deserve money, and the test he ran on himself in that chair is a version of the one he runs on everyone he backs.
The drill went in. He jumped, once. Then he told himself he would not move again.
To hold still he reached outside that room, thinking about soldiers losing limbs in combat and asking what this was next to that.
“It’s just nerve endings from there to my spine to my brain.”
He made his meeting. Afterwards he went home to change his shirt, because he was a puddle of sweat. Asked why he would do such a thing, he did not dress it up.
“My whole life I wanted to see if I was a badass or not.”
He arrived from Italy with no English and got called pasta at school. He worked sailboats while watching the rich kids at the country club, telling himself he would get those guys later.
Forty years on he is still running the same test. He just runs it on founders now.
When it gets real
Ben Horowitz found out what he was made of in public.
Loudcloud went public in March 2001, weeks into the dot com collapse. He and Marc Andreessen had raised $350 million and were approaching $100 million in recurring revenue when the market vanished underneath them. He sold off the operations business, renamed what was left Opsware, and laid off 400 of his 450 people.
He later wrote this.
“The Struggle is when you wonder why you started the company in the first place. The Struggle is when people ask you why you don’t quit and you don’t know the answer.”
Opsware sold to HP for $1.6 billion. The more interesting outcome came two years later, when he and Andreessen built a firm on a thesis born from that loneliness. The only people worth having beside a founder in the worst month are the ones who have been in one.
They had watched each other in the fire. That is the evaluation that clears.
Worth your time
Read The Struggle, Horowitz’s short essay. Three minutes, and it is the most honest thing a famous investor has written about how building actually feels from the inside. Then use it. Send it to anyone you are considering going into business with, and watch what comes back. Recognition is a different reaction than admiration, and it will tell you more than their CV did.
Final thoughts
You cannot interview for this. It is not a line on a résumé, and everybody claims it in a first meeting.
You learn it by watching. What someone does the week a deal dies. Whether they go quiet and useful or loud and absent.
You do not need a company to have seen it. Think of whoever you last built anything with, however small, and what they did when shit hit the fan.
Thanks for reading.
Share Forget the MBA: