Before building six businesses, I had a job. A pretty good one. And before that? An OK one, and another before that. And at the start of it all I delivered newspapers for $11.37 a week. Rain or shine, six days, before school.

That job taught me something many founders forget:

Founders often approach exit prep like a sprint to the finish. But in reality, it’s a long game of strategic positioning, clarity, and clean structure.

The real blockers aren’t just operations; they’re how you present and protect your value before a buyer ever…

You don’t need a better work-life balance.

What you need is a business that doesn’t rely on you for oxygen.

Most founders don’t start their business thinking, “I really want to work 60+ hours a week”.

But then they’ve built businesses that require them to.

Because they haven’t made the shift from:

A while back, I spoke with James McCarthy on the 2 Commas podcast. He’s a founder who successfully exited for eight figures, but not without a few battle scars.

In the early Spidertracks days, James and his team built everything. Billing systems, support tools, even their own infrastructure. Stripe didn’t…

I made my first investment when I was 12. It wasn’t much, but like most people in the market back then, I crushed it. The return? It was epic until the 1987 “Black Monday” crash, but there was still enough to splurge on a pack of pick ’n’ mix and a new bike. Not bad for a kid…

I’m flipping the script to talk about buying, not selling businesses this week. Read on, it remains super relevant as at some stage, you’ll likely be on one side of the transaction….

"Any idiot can buy a business. But it takes a hell of a lot more than that to integrate it and make it successful."