The 21 Hats Morning Report

The 21 Hats Morning Report

The Owner Is on the Roof

Taking over a blue-collar business may not be as easy as it sounds: “If you buy a roofing company, you’re going to end up on the roof at some point.”

Loren Feldman's avatar
Loren Feldman
Apr 01, 2026
∙ Paid

Good morning!

Here are today’s highlights:

  • Here’s another example of private equity trying to scale a beloved brand.

  • Excluding April 2020, this is now the worst job market in more than a decade.

  • Creative Repute’s Nile Livingston explains how she’s finding talent in a tough market.

  • The latest trend: Influencer marketing is going to the dogs.

BUYING THE BUSINESS

Interest in taking over blue-collar businesses continues to build, but it’s not as easy as it may sound: “There’s a romantic narrative online right now: buy a Baby Boomer’s business, apply your digital skills, print money. The pitch usually goes something like: Old owner, fax machine, terrible website, great book of business, 30-year reputation, he needs to retire. You look at that and get this big head where you think: I could do better. Sure, you could build a nicer-looking website. Set up a CRM. Plug in some new software. Run some Google Ads. Automate the invoicing, etc. You could probably do all of that in the first month.”

  • “But there are a lot of aspects where that old guy is The Man, and you’re not. And those are the aspects that actually keep the business alive. Every business is hard and every business is competitive. And in a lot of these companies there’s been no effort put into making the company transferable to someone else.”

  • “Every operation is ‘Ask Jim.’ There’s very few systems or documentation, usually just a network of relationships and knowledge that lives inside one person’s head. By all means, buy the Boomer business. But there’s typically not this simple button you can press where you upgrade some of the tech and extra business starts rolling in.”

  • “A friend of mine put it simply: if you buy a roofing company, you’re going to end up on the roof at some point.” READ MORE

User's avatar

Continue reading this post for free, courtesy of Loren Feldman.

Or purchase a paid subscription.
© 2026 Loren Feldman · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture