Episode One
The Richest He’d Ever Been
Dennis sold his company, did everything right, and quietly stopped building. Nobody said no.
Available Now
The Black Letter Podcast
Stories About Money, Told Like They Matter
Season One
Every episode is one person at the moment their money stopped being simple. Sometimes a sale. Sometimes an inheritance. Once, a house eight hours south. None of them made a bad decision. That is the whole point. These are the stories the industry never tells, because they are not about products. They are about what happens after the wire hits.
What This Is
The Moment the Money Stops Being Simple
There is a moment that arrives for a certain kind of successful person, and it almost never arrives when they expect it. The company sells. The inheritance lands. The plan finally works. And then a line forms, every person in it capable and well-meaning, and every one of them says a version of the same thing: let's make sure you don't lose it.
Nobody in that line is wrong. That is what makes it hard to see. The Black Letter Podcast is about what that line cannot see, told one person at a time.
Episode One · Available Now
The Richest He’d Ever Been
Dennis sold his company, did everything right, and quietly stopped building. Nobody said no.
This Season
Season One
Episode Two
The Best Offer He Could Make
Duane inherited more money than his father ever explained to him, and made me a fair offer. I couldn’t talk him out of it in four tries.
Coming Soon
Episode Three
You Cannot Be Convinced Early
Paula did the homework. That was the problem, and it took me a long time to understand why.
Coming Soon
The Host
Josh Ryan
Josh Ryan is the founder of Cornerstone Wealth Management Roscoe and the author of The Most Expensive Thing. He works with business owners, real estate investors, executives, and generational families at the point where their wealth outgrew what built it. The podcast is where he tells the stories behind that work.
The industry is good at trying to make sure you don’t lose it. It was never built to ask what you were going to do with it.
The Black Letter Podcast
Beyond The Podcast
The Podcast Is One Part of Black Letter
The stories are public. The rest is not. The Black Letter Private List is where the thinking behind these conversations continues, written only for the people already there.