Envy Can Be Useful, or It Can Eat You Alive

Do you want to tell us about some of the jobs that you had as a youth and the specific job that kicked off your fanatical obsession with creating wealth? This gets a little personal, and I don't want to do the humble brag thing. There was some thread going around Twitter about, like, name five jobs you've held, and every rich person on there was trying to signal how they were held, like, normal jobs. So I don't want to play that game.

I've held a bunch of menial jobs. There are people who have had worse than me and people who had it better than me. There was one point where I was washing dishes in the school cafeteria, and I said, “Eff this, I hate this! I can't do this anymore!” I sweet-talked my way to a computer science prof into helping TA his CS class in algorithms when I myself was completely unqualified for that.

So it forced me to learn computer science algorithms so I could TA the rest of the course. But that desire came out of the suffering of washing dishes in the college cafeteria, which is not to say there's anything wrong with that. There's nothing wrong with anything, really, but it was just not for me. I did not enjoy it. I had an active mind, and I wanted to make my money and earn my living through mental activities, not through physical activities.

But sometimes it takes the suffering of doing the wrong thing to motivate you enough to do the right thing. I worked at a law firm for a while, a big, prestigious law firm in New York City. I had a big internship there, and I basically got fired for surfing. Using that back in the day—this is before the internet was a big thing—using that was the newsgroups, and it was the only way for me to stay from being completely bored.

I was an overpaid guy wearing a tie and a suit and had to hang out in the conference room when the lawyers needed photocopies. I would make photocopies, and in the meantime, I would be bored out of my skull. This is pre-iPhone. Thank God to Steve Jobs for saving us all from unending boredom. But I used to read the Wall Street Journal or anything that I could get my hands on. I would have read the back of a brochure just to keep from going insane because listening to a bunch of corporate lawyers discuss how to optimize minute details in a big contract is really dull.

They got mad at me because they wanted me to sit there quietly and not read The Wall Street Journal. They said that's rude, that's misbehavior. So I got called up and reprimanded a bunch of times, and then I was finally terminated and I was sent home in shame early from my very prestigious internship. This was my chance of going to law school. I was unhappy for all of an hour, but ultimately it's one of the best things that ever happened to me because then I would have ended up as a lawyer. Not that I have anything against lawyers, but it's not what I was meant to do.

You mentioned the catering job that you had a while back that really kicked off the whole obsession. That was an envy thing. When I was in high school, I had to make some money to pay for my first semester at college, and I had to get a job. It was the summer of 1990-1991 timeframe. So this was the Bush senior recession. If anyone who was alive back then remembers, it was actually really hard to get a job.

So I ended up working for an Indian food catering company. I ended up having to serve at a birthday party for a kid who was actually in my school. So I saw my classmates, and I was out there serving food and drinks to them, and that was incredibly embarrassing. I wanted to hide away and die right there. But you know what? It's all part of the plan. It's all part of the motivation.

If I hadn't had that happen, I probably wouldn't be as motivated, and I wouldn't be as successful. So it's all fine, but it was definitely a very strong motivator in that sense. Envy can be useful, and it can also eat you alive if you let it follow you your entire life. But there are points in your life where it can be a very powerful booster rocket.