The moment

At some point, you stopped racing to win someone else’s game.

Maybe you saw it clearly. Maybe it was slower than that — a creeping sense that the harder you executed, the more crowded it got. Position inside a category someone else defined has a ceiling. Execution alone can’t break it.

That’s the breakaway. Not the finish line. Not the podium. The moment one rider pulls clear of the peloton and open road appears.

This newsletter is for the leaders who’ve already made that move.

The thesis

Technology doesn’t level the playing field. It compresses the peloton and amplifies the breakaway.

When AI accelerates execution for everyone, working harder inside the existing race gets you nowhere faster. Speed is no longer the advantage. Category ownership is.

Joe Rogan is a category of one. He din’t go anywhere — Spotify came to him, YouTube came back to him. He negotiated from category ownership, not desperation. The platforms needed him more than he needed any single platform.

That’s platform optionality. And it’s not an outcome you plan for. It’s what happens when you own your category and every new technology wave comes looking for you.

That’s the one idea this newsletter exists to explore — in every direction, at every altitude, across every industry where it applies.

Who this is for

You don’t have to convince yourself you’re this person. You’ll know.

You’re a founder who thinks like an operator — you initiate change and design the systems that sustain it. Or you’re an operator who thinks like a founder — you execute and understand why the machine is built the way it is. Either way, you’re running fast and sensing a ceiling you can’t execute through.

You’ve outrun your strategy.

You’re executing brilliantly inside a category someone else defined, and part of you knows the move is a different frame entirely.

You don’t need to be taught how to work hard. You need the thinking that belongs to your position.

That’s what The Breakaway delivers.

This newsletter is not for you if you’re still looking for the playbook that will beat everyone else in the category you’re in. That’s the peloton’s game.

There’s plenty of content for people running that race.

About Michael

I’ve spent my career building in conditions that most people use as excuses.

I was in finance when 2008 hit — one of the first industries to feel it. I was leading strategy at a travel tech company when international travel locked down in 2020.

Two Black Swans, a decade apart, across industries that had nothing in common except this: the leaders who kept moving weren’t the fastest executors.

They’d already stopped competing inside categories they didn’t own. Every disruption that compressed the people around them just opened more road ahead.

That’s the pattern I kept finding. That’s what I write about here.

What you’ll find here

Each issue goes somewhere specific — a case, a frame, a decision that category-level leaders actually face.

Strategy at altitude, above the tactic layer, focused on the decisions that determine which game you’re playing.

If it belongs to a founder who operates and an operator who thinks like a founder, it belongs here.

The one thing I won’t do

Teach you how to become a category of one.

You’re already out front, or you’re close enough that you can feel the gap opening. What you need is the thinking that belongs to that position.

The Breakaway doesn’t recruit. It recognizes.

If you’ve felt the ceiling that execution alone can’t break through — you’ve found the room.