Aug 28, 2026

S6:E74

What happens to your business when you aren't there anymore?

For millions of founders, where more than half of all small businesses in the USA today are owned and operated by people over 50, that question is moving from theoretical to urgent.

John Abrams says many owners assume they'll eventually pass the company...

Aug 27, 2026

S6:E73

“If you were just here sooner.”

Jim Martin has never forgotten those words.

They came from an employee of a 125-year-old company with approximately 1,800 employees that ultimately had to be liquidated. Jim had been brought in during the crisis. But by then, many of the options that might once have existed...

Aug 26, 2026

S6:E72

Dating apps give us more choices than we've ever had, so why does finding the right person feel harder? Some people have given up, saying that it is "impossible" to find a mate!

Matchmaker April Davis says too many options may actually be part of the problem, encouraging people to filter potential partners by...

Aug 21, 2026

S6:E71

AI has raised the floor. But has it raised the ceiling?

Gee Ranasinha doesn't think so.

AI has democratized content production, giving small businesses access to capabilities once reserved for larger organizations. But Gee argues that we're simultaneously creating what he calls a greater “preponderance...

Aug 18, 2026

S6:E70

Stop Trying to Be Everything to Everyone with Christine Blosdale

You can be extraordinarily talented and still make yourself almost impossible to hire.

Christine Blosdale sees it constantly: entrepreneurs with multiple skills, multiple offers, multiple audiences and multiple platforms trying desperately not...