What 8 Unlikely CEOs Taught Me About Building a Legacy

Hi there friends,  

If you lead a family business, odds are you’re playing a different game than most CEOs. 

You’re not just chasing results. 

You’re shaping a legacy. 

And legacy demands a different kind of thinking. 

That’s why I love The Outsiders by Will Thorndike — a generous, clear-eyed study of eight unconventional CEOs who outperformed their peers by a mile. 

Not by following best practices. 

But by following their convictions. 

These leaders weren’t media darlings or quote-machine founders. 

They were disciplined. Patient. Independent. 

They didn’t build with flash. 

They built with brick. 

As Naval Ravikant says: 

“Play stupid games, win stupid prizes.” 

These CEOs refused to play short-term games. 

And they won accordingly. 

My Top 3 Takeaways from The Outsiders 

1. Capital Allocation Is Leadership 

The best CEOs are master allocators of capital. 

More than simply managing operations — they deploy energy, attention, and resources like strategic assets. 

Where you place focus is where you place your future. 

And in a family business, every capital decision has ripple effects that reach the next generation. 

Thorndike shows how these leaders resisted short-term optics to reinvest wisely — over time, not quarters. 

2. “Who, Then What” — Katherine Graham’s Legacy Move 

Katherine Graham, the legendary CEO of The Washington Post, didn’t start with bold ideas. 

She started with bold hires. 

• She brought on a world-class managing editor 

• She recruited a rock-solid COO 

• She sought mentorship from Warren Buffett himself 

She was humble enough to surround herself with smarter people — and courageous enough to let them lead. 

That’s legacy stewardship: putting the right people in the right places to build something that lasts. 

3. Think in Decades, Act with Discipline 

The through-line in every profile is simple: long-term thinking wins. 

These leaders were frugal, focused, and fiercely independent. 

They weren’t contrarians for the sake of it — but they weren’t afraid to go against the grain. 

They made bold moves when the moment was right. 

And they held the line when the pressure to grow fast was loudest. 

They weren’t trying to impress Wall Street. 

They were building institutions. 

If you’re running a family company, The Outsiders will feel like a breath of fresh air. 

It’s not about buzzwords. 

It’s about focus. 

Discipline. 

And clarity of purpose. 

I love reading about long-term thinkers in a short-term world. 

And I have a feeling you will too. 

Onward,

Matt