When Should You Go "All In"?

Guy Raz Newsletter – July 25, 2024

There’s a tough question many founders eventually face: when should I go “all in” on my business? 

Lots of HIBT entrepreneurs started their businesses alongside holding a full-time job. For almost everyone, this is the “right” and “secure” thing to do. Your FT job funds your side project and gives you more runway than you might otherwise have.

But on this week’s HIBT, it’s quite the opposite. Olivier, Caspar, and Adam (founders of On Shoes) went “all-in” from the beginning. 

They even wrote it into their agreement: if anyone took on a side job or another full-time job, they would lose ALL their shares in the company. 

On the one hand, it’s incredibly risky. They had well-paying jobs at impressive companies. They left secure jobs for a pipe dream. 

On the other hand, they were extremely focused from the start. They put their backs against the wall. They moved all their chips to the center. And they essentially had no other choice but to make it work.

It’s a tricky thing. There isn’t a unive…