20VC: Andrew Wilkinson on Building The Berkshire Hathway of Tech, Sustainable vs Unsustainable Growth and The Relationship Between Money and Freedom

When I started making money, I went out and I bought a fancy car, and I bought nice clothes, and fancy stereos, and all these things, and I didn't find that it had any impact on my happiness. The only thing that had an impact on my happiness was not stressing out about rent, knowing I had enough money in the bank that I was comfortable for two or three months, I could go out and eat when I wanted and drink what I wanted.

For me, I look at money, first and foremost, as a way to protect my personal freedom, and what I mean by that is building a wall between me and things I don't want to do, people I don't want to see, [and] ways I don't want to spend my time.

I think school is often a waste of time, especially if you're in tech. My number one piece of feedback to people is get experience. If you want to be in business, start a business; don't do an MBA.

In talking to people who are older, I've realized that, ultimately, the main [things] that matter are being part of a community and having activities you can engage in, having great friends, and having a wonderful family and grandchildren.

I have a system that I call 'anti-goals.' Every year, my business partner and I sit down and say 'What does our worst possible day look like, and how do we design our day to avoid that?'

We [Tiny Capital] don't want to be in a situation where we're buying a company where billions of dollars are going to flow into competing with it tomorrow. We just think that's too difficult. So, that's why we like to choose industries that are sleepy where nobody really cares about them ... Maybe there's not a multi billion-dollar opportunity, but there's a ten or a hundred million-dollar opportunity.

I would say my superpower is pace and delegation. So, I'm like an icebreaker—I know how to make teams move quickly and blow down barriers and get things done very, very quickly using delegation.

When it comes to social networks, usually the largest network always wins.

Like a lot of founders, I'm very urgent and I love doing things quickly. I love ideas. I love strategy. What I don't really like is implementation and follow through and managing people ... I'm very good at laser focusing for a short period of time on one company, deal, idea, strategy, whatever it is. But I don't enjoy spending the next 60 days implementing a plan and building that plan.