Starting Up Vs Staying On

A few years ago, I had a chance to work with an exciting tech startup. They had just become 5 years old. The day I went for an interview, about a dozen of the founding members announced they were quitting. Including the CEO.

Was this a good sign or a bad sign? Over beers, my friends were all adamant that this was the end. The sky was falling and the little-startup-that-could was crashing and burning.

I fundamentally disagreed. I thought it was a healthy sign.

There are two types of people in the world⁰ - those who like risk, and those who like stability. There's nothing wrong with either, of course. It's fun and exciting to try something new. But there's no shame in only wanting to work somewhere with a competent payroll team and a predictable schedule.

The people you need to help run a startup are probably different from those you need to run a successful business.

There are only two paths for a new business¹ - success or failure. For some, success is a billion-dollar exit, for others success is a profitable business which employs a dozen people. For some, failure is bankruptcy, for others failure is a profitable business which only employs a dozen people.

At the five-year mark, a successful startup should be a fundamentally different place than it was at the start.

If after several years you're still hiring - and retaining - people who want the thrill of starting up, then your organisation isn't maturing. That may, or may not, be a problem.