Jason Fried

January 12, 2024

Swimming the center or the edge

Imagine a vast swimming pool 25 miles long, 50 miles wide, and 25 feet deep. Swimming this pool is akin to running a business. And how you swim this pool is akin to how you run the business.

Everyone starts at the beginning, but you decide how close to the center or the edge you swim. There’s only one rule: You can’t turn around, there’s no going back.

Where would you start?

Given the dimensions of the pool, here’s how I’d do it: I’d start near the edge. The edge effectively creates multiple “shores”. You can swim all the way to the end, or you can grab the side and stop for a breath, a break, or even decide “that’s enough” and stop there. This is optionality. More points of survival. To me this represents independence.

But not everyone decides to start at the edge. Oftentimes, a key strategic decision pushes them center: Raising money. And the more money they raise, the further center they’re pushed. At some point, there’s only one way to make the business work: To reach the other side. Once you begin, the edges are further away than the end. There’s no optionality, you can’t stop. You either make it across, or you die.

The choice between VC funding and bootstrapping independently depends on an entrepreneur's appetite for risk and personal definition of success. VC funding is typically for those who aim for a singular, large-scale “win”, while bootstrapping appeals to those seeking path with multiple potential outcomes along the way. One wants it all, while the other wants enough.

Realistically, there are other places to start than just the edge or the center. You can start further center but still closer to the edge. But the further center you go, the more risk you take, and the fewer options you have. Every entrepreneur has to figure out what makes sense for them, but for me, optionality is worth more than one big outcome.

What about you?


About Jason Fried

Hey! I'm Jason, the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Subscribe below to follow my thinking on business, design, product development, and whatever else is on my mind. Thanks for visiting, thanks for reading.