Andrew: "At 25 I was CEO of Startup Weekend. I’d started it at 22. By then it had exploded to 20 countries. I was living in the most beautiful city (Boulder), I built something that a lot of people loved and I was working 7 days a week on it."
Kate: "So you had it all. That was probably confusing at such a young age."
Andrew: "Yeah it was weird. I was different than most 25 year olds. I’ve always had more confidence than anyone else I know -- I’m sure helped along by societal biases. My whole life I’ve been the tallest guy in the room and one of the smartest so challenges always seemed like tests. I’ve always just gone after things already knowing I’d have a great chance of figuring it out. I discovered this talent for bringing people together, and I made something huge from it.
But I had my social life pinned on that, which was great because it was truly what I loved but not like most of my friends social lives. Most of my college friends all had terrible jobs but seemingly had great social lives. I was just so different and enjoyed that."
Kate: "So would you change that? Would you tell yourself not to work less and go party more?"
Andrew: "Absolutely not. I’m an introvert. I like being home alone on Friday nights. I can manage a drunken two-step, but dancing at a club? No thanks. That was around the time I was figuring that out."
Kate: "So… what is it you wish you had known back then?"
Andrew: "I have some thoughts for current 25 year olds --
Kate: "So you had it all. That was probably confusing at such a young age."
Andrew: "Yeah it was weird. I was different than most 25 year olds. I’ve always had more confidence than anyone else I know -- I’m sure helped along by societal biases. My whole life I’ve been the tallest guy in the room and one of the smartest so challenges always seemed like tests. I’ve always just gone after things already knowing I’d have a great chance of figuring it out. I discovered this talent for bringing people together, and I made something huge from it.
But I had my social life pinned on that, which was great because it was truly what I loved but not like most of my friends social lives. Most of my college friends all had terrible jobs but seemingly had great social lives. I was just so different and enjoyed that."
Kate: "So would you change that? Would you tell yourself not to work less and go party more?"
Andrew: "Absolutely not. I’m an introvert. I like being home alone on Friday nights. I can manage a drunken two-step, but dancing at a club? No thanks. That was around the time I was figuring that out."
Kate: "So… what is it you wish you had known back then?"
Andrew: "I have some thoughts for current 25 year olds --
- Spend your time being wildly passionate about something no one else is passionate about. Don’t be a poet, a sports instructor, or try to work in sports entertainment. Those people are good people, but you’ll be competing against an infinite number of others for the rest of your life. There’s no way to carve out a niche. If you want to advance or make money, you have to find something different.
- If you don’t own it, you never will. Someone told me that at my first ever job bussing tables at 16. It’s both internal and external. If you don’t truly believe that you’ll succeed at something, you only hold yourself back. You won’t push as hard. Others will see you aren’t pushing and they won’t invest in you either. If you don’t act with the pride of ownership you never will get the chance to own anything.
- Just be a kid for awhile and relax. Stop worrying about whether you’re doing things right. You told me what you needed to hear just by asking this question. It’s like when someone asks, “How do you know if you need to fire someone?” If you just asked me that, it means you should fire them. Calm down. Have fun with your friends. Stop asking this question. Enjoy your 20s. You’ll figure it out."