Bill Gurley

One of the guys on the Acquired podcast came up with this idea, which I really love, called side hustles.

And he says, while you're at a job, they'll probably let you do something else if you're willing to do it in your off hours or whatever.

Right.

And so he gives examples of three different stops in his career where he intentionally did something else on the side.

One of them was at Microsoft.

He started Microsoft Garage, which was this community of entrepreneurs using Microsoft projects.

And that led him to a whole different set of connections and networking than if he had just sat there in the job they had defined for him.

And then when he got to Madrona, he started a podcast on the side.

He said to the people at Madrona, can I do a podcast from the VC firm?

They said, yeah, sure.

And, of course, now he's one of the most successful podcasters on the planet and loves what he's doing.

But the experimentation of this side hustle gave him exposure to new things.

And in both those cases—

in a very differentiated way.

So that's another thing you could do if you're 40 and feeling trapped.

You know, ask yourself, could I, would the career I'm in, the company I'm at, let me go do this other thing?

There you go.

People that write personal development books talk about mentors, so it's not a unique topic.

But what I find happens most in the real world is people get too greedy too early.

And they say, well, they either cold call someone they shouldn't.