Project Software Scaling Loss

Andrew Wilkinson shares a story about a major business failure that taught him valuable lessons about scaling.

"I lost $10 million building project management software. That was a perfect example where I got ahead of myself - the business didn't make sense and I threw a bunch of spaghetti at the wall and none of it stuck. I had to let a whole bunch of people go and it was really horrible and sad. It was like a 10-year slow death.

I've been through that, so now with the amount of scar tissue I have, I have enough signal where I can be more careful. With the bakery, I was just contracting a friend. With the news business, I actually ran it for 3 years before I partnered with Farhan and he took over as CEO. By that point, there was enough signal - it was slapping me in the face that this was a big opportunity.

Now if I hire a CEO, I'm pretty high conviction that there's something there or there's already a business that has cash flow. What I would never do is say 'Hey, I have an idea for this, I'll just go hire a CEO.' I would never do that."