What it takes to run a business

Podcast

This week, Paul Downs tells Kate Morgan and Liz PIcarazzi that he recently posted a job on Indeed and got 153 resumes—more than he’s ever gotten before, which prompted some interesting questions: What does this mean for business owners? Should a job posting be more about what the company expects from a candidate or more about what the company has to offer? Do the owners ask candidates to take personality tests? If the owners get 150 resumes, do they ask ChatGPT to review them? And doesn’t it seem as if more people are looking to switch careers? “When I look at someone who's working as a graphic designer in an ad agency,” Paul tells us, “I'm thinking: This person realizes AI is coming for their job.” Plus: Liz gives us a surprisingly upbeat update on her tariff situation. And the owners respond to a Reddit post asking whether it would be crazy to start a business in the current economic environment. Paul’s response: “Don’t do it.”

This week, David Barnett, Mel Gravely, and Kate Morgan discuss a somewhat unusual approach to succession, which is to not sell the business. Basically, it’s about taking a step back from leadership while maintaining ownership, and both Kate and especially Mel are moving in this direction. The approach can pay off financially in part because businesses often are worth more to the owner than they would be to a buyer. Why is that? As David explains, the business that the buyer buys isn’t really the same business that the owner sells: “If you've owned the business for a long time,” he says, “the balance sheet is probably pretty strong. You've had time to earn money, pay down debts. You’ve got a good equity position. This makes the business strong, and it makes it better able to weather storms.” But, as David goes on, if he were to buy Mel’s business, he would probably have to borrow money to finance the acquisition. That would leave him with a much weaker balance sheet than Mel has today. And a significant portion of the cash flow that Mel currently generates would have to go to the bank. Which is part of the reason Mel’s keeping his business. Of course, this approach to succession does have some challenging elements, including the need to find someone to run the business. Plus: We also discuss whether it’s possible to sell a solopreneur business.

This week, we meet Dan Carmody, who has gained an unusual perspective on what it takes to build a business in the United States. Dan has started and built his own businesses. He’s run community development organizations that have worked to support the growth of other local businesses. And until January, he was CEO of the Eastern Market in Detroit, which is one of the last great public markets in the country and has seen a remarkable number of businesses start, thrive, and even go national. On top of that, he’s also traveled to other countries to see how they support small enterprises. His conclusion? We’re doing it wrong. This may seem jarring given the story we like to tell ourselves about the American Dream, but as Dan explains, there are some things we could learn from other countries.

This week, we’re joined by special guest Alan Pentz, who recently stepped back from his government-contracting business to start the Owner Institute, which draws on lessons he learned the hard way to help business owners scale their businesses. In his new role, Alan has immersed himself in the world of generative AI, and he’s come to some intriguing conclusions, one of which is that AI will eliminate most B-to-B agencies—marketing agencies, public relations agencies, professional services firms. Why is that? Because, Alan says, businesses will no longer be willing to pay agencies retainers of $5,000 or $10,000 a month once they realize they can get similar or even superior work from an AI chatbot. “In general,” Alan says, “most technology waves end up with a few big winners, and most people are just roadkill.” To explore the theory that agencies are likely to be roadkill, we invited Jaci Russo, owner of a marketing agency, and Sarah Segal, owner of a public relations agency, to have a conversation with Alan. Spoiler alert: There were no tears, no threats, and no insults.

This week, we bring you a conversation recorded at our recent 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of one of America’s most influential small businesses. Starting 43 years ago with a highly successful college-town delicatessen that they could have replicated all over the country (including for Disney), Ari and co-founder Paul Saginaw have instead built Zingerman’s Community of Businesses, a collection of 12 Ann Arbor-based, collaboratively run businesses each with its own leadership and ownership structure. Together, these businesses produce $80 million a year in revenue. They include a bakery; a coffee company; two event spaces; a roadhouse; a Korean restaurant; a mail-order operation; an international food-tour business; a publishing house that publishes, among others, Ari Weinzweig; and a training center—ZingTrain—that has shared the Zingerman’s approach to business building with more than 10,000 other businesses.

In 2003, Bo Burlingham pronounced Zingerman’s “The Coolest Small Company in America.” Bo’s article became the foundation of Small Giants, his book about companies that are more intent on being great than being big. The last thing we did at 21 Hats Live was to sit down with Ari to talk about that philosophy. In his passionate responses to our many questions—reponses, I should note, that include a few F-bombs—Ari explains how the Zingerman’s team decides whether to start a new business, how he and Paul made (and re-made) an especially difficult decision about expanding, how he and Paul have managed to sustain their partnership for more than four decades, how they chose a succession plan, how they know if they’re charging enough, why for many years Ari’s mother continued to believe he was a failure, and a whole lot more.