The Founder Trap

What happens when the wrong thing works?

Entrepreneurship starts with experimentation and failure. Learning how to create value for others takes practice, and during that practice, you're going to make things no one wants or cares about.

Thankfully there are ways to shrink the failures and tighten the feedback loops. The Lean Startup Method has saved millions of years of time, encouraging entrepreneurs to build the smallest viable version of their product first instead of wasting years and small fortunes on an unvalidated idea. 

The great thing about staying lean is it allows you to rapidly iterate on new ideas, quickly testing businesses to figure out which one will work. The bad part is that in all the excitement of starting and testing ideas, you might not consider what it means to succeed.

At some point, entrepreneurship goes from giving you maximum optionality to providing none at all.

It clicked for me when a bank called to verify an employee worked at Growth Machine. She was buying a house. I answered the banker’s questions, hung up, and a few hours later it hit me: I really shouldn’t screw this up. It wasn’t just my income and lifestyle riding on my work. Someone’s house was too.

That seriousness intensified with each new employee and each new employee’s life milestones. Someone finds out they really need good health insurance. Someone has a baby. More houses. 

That seriousness can be one of the greatest sources of meaning in your work as an entrepreneur. Supporting someone taking maternity leave during COVID was much more rewarding than hitting revenue milestones. But that seriousness can also trap you because you quickly hit the point where you can’t quit.

I know at least a couple of founders running successful, ten or hundred-million-dollar businesses, who are miserable. They don’t like the company anymore and aren’t inspired by their work, but they’re trapped in a cage of their own design. They can’t walk in and say “I quit” without the company falling apart, and they haven’t been able to replace themselves. 

Is the problem you’re working on something you’re excited to tackle for the next five to ten years? If not, how do you keep it small enough to avoid getting stuck? And even if it is, how do you set yourself up from the start to not end up feeling trapped or resenting the path you set yourself down?

It’s always been curious to me that Eric Ries, author of The Lean Startup, then went on to start the Long Term Stock Exchange. If you wanted to find a peak example of an un-lean business, a stock exchange is up there. What did Eric know that didn’t make it in his book? Perhaps starting lean is a good formula for not going broke, but a poor tool for creating meaning. 

If our goal is to create fulfilling work, asking “what happens if this succeeds” is as essential as asking “how do I make this work?”