All Episodes
21 Hats Podcast — 40 episodes
You Just Lowered the Value of Your Business
Dashboard: He Sold the Business. The Regrets Came Later
She Thought She Was Building a Prospecting Tool for Herself
Dashboard: The Competitive Advantage AI Can’t Copy
We’re Growing. Now I Want to Make Money
Dashboard: Stop Asking How to Use AI
Best of: Selling My Business Nearly Broke Me
Dashboard: Is Staying Small Selfish?
With My New Rent, I Will Clear Nothing
Dashboard: It’s Not That Earnouts Are Bad. It’s That Bad Earnouts Are Bad
My Succession Plan Just Moved to Montana
Dashboard: The Problem with Retainers (and Other Lessons for Solopreneurs)
You’re Pre-Qualified for a 13% Loan! (That Really Costs 170%)
Dashboard: The ESOP Risk Nobody Talks About
‘I Want My Employees Building My Business, Not Theirs’
Dashboard: Why Open Books and Employee Ownership Aren't Enough
Would You Rather Own a Business in the U.K. or the U.S.?
Dashboard: Why Do People Keep Starting Businesses?
I’ll Deal with Succession Next Year
Dashboard: You're Probably Not Spending Enough on AI
What Do You Owe Your Employees?
Would Your Business Survive a Divorce?
Dashboard: The Growth Strategy Hiding in Your Supply Chain
Why Do You Pay What You Pay?
Dashboard: A Compensation Plan Becomes an Exit Plan
Maybe EOS Will Solve Our Problem
Dashboard: Helping Creatives with the Business of Art
Would You Rather Risk Losing a Client or an Employee?
Dashboard: A Buyer That Doesn’t Want to Flip Your Business
‘I’m Skeptical AI Is Going to Help Us’
Dashboard: Uber for Landscapers
In Search of Companies More Interested in Being Great Than Big
Dashboard: Is It Still Worth Selling on Amazon?
When Employee Violence Walks Through Your Door
Dashboard: A Marketplace for Ethical Exits
The Real Payoff May Be in Owning, Not Selling
Dashboard: Should You Pay $3,500 a Month for SEO?
When That Big Break Just Might Break You
Dashboard: Bringing a Bazooka to a Wine Fight
There’s Scope Creep Around Every Corner