The 21 Hats Morning Report

The 21 Hats Morning Report

The Two Kinds of Business-Owning Parents

There are those who hope but don’t push their kids to join the business and those who make it awfully hard to say no. Josh Patrick didn’t realize he was in the latter group.

Loren Feldman's avatar
Loren Feldman
Jul 22, 2026
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Good morning!

Here are today’s highlights:

  • Who has it better, U.K. business owners or U.S. business owners? Let’s talk about taxes! And employee tribunals!

  • Your website was designed for humans. Gene Marks explains why it has to be redesigned for agents.

  • A small town fell for a phishing scam, and so far, at least, a family-owned contractor is out half a million dollars.

  • Brandon Gray reports that profits are up for the Simple Numbers 100 businesses.

FAMILY BUSINESS

Of course most owners hope their kids want to join the business: “There’s a story I heard once that could just as easily have been about me in my olden days. A business owner gets the call that his wife has gone into active labor. He grabs his keys, heads for the door, and on his way out he turns to the whole office and announces: ‘Your future boss is about to be born.’ His son wasn’t even born yet. Hadn’t taken a first breath, hadn’t cried, hadn’t done a single thing on this earth. And the dad had already handed him the corner office. He’d already decided that this unborn kid would run the company someday.”

  • “My first reaction was to judge the guy. Come on. The kid isn’t even here yet, and you’ve already written his whole life for him? My second reaction, though, was quieter and a little more uncomfortable. It was recognition. Because I know that feeling. I never stood up in an office and said the words out loud, but I have absolutely looked at one of my own kids and quietly filled in a job description they never applied for. I’ve done the thing that dad did. I just did it in my head instead of in front of the staff.”

  • “Most business-owner parents I meet would absolutely love it if their kids came into the business. Of course they would. You build something with your own two hands, you pour 20 or 30 years into it, and the idea of handing it to someone who shares your last name feels like the story is supposed to end. It feels like legacy. It feels like the whole point.”

  • “So what do parents do with that dream? It kind of splits into two camps. Some parents hold it loosely. They’d love it, but they don’t push. They leave the door open and let the kid decide whether to walk through it. And some parents make it awfully hard to say no. They dangle it, they groom for it, they build the expectation up so high and so early that turning it down starts to feel like a betrayal. Like standing up in the office before the kid’s even born and announcing who the future boss is going to be.” READ MORE

THE 21 HATS PODCAST

Where the Grass (and the Money) Is Greener: Nearly 10 years ago, Simon Bedding, who owns a manufacturing company in England, picked up a copy of Boss Life, Paul Downs’ memoir about running (and almost losing) a manufacturing company in Pennsylvania. Simon liked the book enough to email Paul. Paul wrote back. And over the years, they’ve kind of stayed in touch. This year, as we mark the 250th anniversary of the United States spinning off from the United Kingdom, we thought it would be illuminating to get these two business owners together to compare notes. After all, their countries started with the same language and much of the same legal tradition, but two and a half centuries later, running a business on opposite sides of the Atlantic can feel very different.

  • In this episode, Paul and Simon compare taxes, regulation, hiring, health care, government support, and what it’s like to build a manufacturing business in their respective countries. Along the way, there are plenty of moments when one of them can’t quite believe how the other has to operate. Wait—you can’t fire an employee without going before a tribunal? Wait—you have to spend a week every year figuring out health insurance? Wait—your employees don’t have employment contracts?

  • And yet, for all of their differences, Paul and Simon also discover something else: Whether your factory is in Pennsylvania or southeast England, some challenges are universal. It’s hard to find great people. It’s hard to fight city hall. In short, it’s hard to build a successful business. And, as Paul puts it, “You’re always going to learn something by talking to other business owners.”

  • You can subscribe to the 21 Hats Podcast—brought to you by Grasshopper Bank—wherever you get podcasts.

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