Never Enough

I was embracing what I came to call Lazy Leadership: the idea that a CEO’s job is not to do all the work, but more importantly to design the machine and systems. Not a player on the field. Not the coach. But the owner, sitting up in a little box at the top of the arena, passively observing until the next critical fifty-thousand-foot decision had to

What caused this, I later realized upon reading Luke Burgis’s book Wanting, is something called mimetic desire. The idea that whatever those around you model as being valuable and important, you unconsciously find yourself caring about and wanting, too. Whether it’s as simple as a fashion choice, like a wristwatch, or as complex as a meaningless pr

This had led me to the epiphany that there is always somebody else who loves the job you hate.

This was how every business worked—creating the demand, building the systems and processes, hiring other people to do the work, then charging enough for whatever it is that you’re selling that you turn a profit. Counterintuitively, you didn’t actually do most of the work yourself, and yet you earned the profits for putting it all together.

My sales technique was simple: be fun to drink with and ask a ton of questions about whomever I happened to be talking to. It worked surprisingly well.

“I know of nothing more despicable and pathetic than a man who devotes all the hours of the waking day to the making of money for money’s sake.”

I started to cold-email CEOs of startups that had just raised ungodly sums from venture capital. I had a simple insight: most CEOs checked their own emails, and it was easy to guess their email addresses. What did I have to lose? Whenever I saw a company announce a big raise on TechCrunch, I’d figure out the CEO’s email and contact them. With the c

“All I want to know is where I’m going to die, so I’ll never go there.”

My key insight at this time was one that would become the core of how I run my businesses today: It’s not enough to do what you love. You also have to stop doing what you hate. The goal isn’t—as many people think—to not work at all; it’s to only work on things that you enjoy doing. The stuff that you’d do even if you didn’t get paid for it.