Lost $10M Across Ventures

Andrew Wilkinson shares how his early success led to overconfidence and multiple failed business ventures.

"I had that classic thing where I had overconfidence. The way I would put it is that my first business was a very easy business. I did the equivalent of walking into the gym and got lucky - I picked up really light weights and it built my confidence. Then for the next 5-10 years, I would walk into the gym and try to deadlift 300 pounds, but I didn't know that was hard.

I started an ecommerce business, a restaurant, multiple software businesses that I bootstrapped and lost in one case over $10 million. I would just be in the shower and think 'Oh man, that's a great business idea' and start it right now today. I had no filter whatsoever. It was really exciting - I was constantly starting new stuff.

I lost about $1 million on the restaurant. We had a viral blog called Clients from Hell, we tried to write a book for it, we had a concierge service. Out of probably 10 different projects or companies I started, only one of those worked really well. There was a lot of pain - I had to lay a lot of people off and go through a lot of hard times."