
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.
This week, in Episode 248, we bring you a taste of what we experienced at the recent 21 Hats Live event in Ann Arbor, where we did a deep dive into a challenge confronting Mars Chapman, owner of Casey’s New Orleans Snowballs, a snowcone business in Austin, Texas. Mars, who is 36, bought the business from his parents and also inherited from them a somewhat laidback approach to ownership. The business has been operating for 29 years, but it has generally run only eight months of the year, which has been enough, thus far, to support a comfortable lifestyle for its owners. But Mars, whose wife, Page, works for a nonprofit and who is pregnant with their first child, has begun to question whether his current approach will be enough to support a family. This is another in our series of 21 Hats Brainstorms—we used to call them Fish Bowls—in which we pair an owner facing a challenge with a group of entrepreneurs eager to help. We ask questions, break into small groups to exchange ideas, and then report back. Sometimes—as I personally experienced at last year’s 21 Hats Live event—the comments and suggestions can be challenging, even a little painful to hear. But they’re always constructive.
This week, we welcome a new regular, Kate Morgan, who joins the podcast along with Paul Downs and Jay Goltz. Kate is the CEO and founder of Boston Human Capital Partners, which provides recruiting and HR services, mostly to other small businesses. After a very difficult stretch caused by the pandemic, Kate’s business has been growing again – but Paul and Jay think she’s leaving money on the table. They think she needs to raise her prices. “I mean,” responds Kate, “we're growing in an industry that we're seeing shrinking right now, and so it's one of these things: Do I want to scare the squirrels and jump up our prices? That's where I've been struggling.” Plus: Are HR people supposed to protect the employees or the business? And after having to lay off a third of his workforce, Paul gives us an encouraging update on how his business is doing.
This week, we meet special guest Ben Knepler, who, along with his True Places co-founder Nelson Warley, came up with an idea for an outdoor chair that they believe could be a game-changer. They liked the idea so much that they quit their corporate jobs, they raised money, they borrowed money—putting their own homes at risk—they fought through the pandemic, they found a manufacturer in China, they launched on Kickstarter, they found another manufacturer in Cambodia, and then they ran smack into the brick wall of President Trump’s second-term tariffs. Or, as George Harrison almost put it, “If you try to sit, I’ll tax your … sturdy, portable, folding chair that could create a whole new category of high-end outdoor products except you’ll probably have to try to sell them in some other country … ‘cause I’m the tariff man.”
This week, a new regular, David Barnett, joins the podcast along with Jaci Russo and William Vanderbloemen. David, who has been a guest on the podcast before, helps people buy and sell businesses—but, as he explains, he’s not a business broker. He’s found a different business model. David, Jaci, and William discuss why it’s so hard to sell a business, what owners can do to make their businesses more attractive to buyers, and why it can be in everyone’s interest for sellers to accept an earnout. Plus: Jaci talks about why she used a recruiter to help her hire a business development person and why she ended up choosing someone who checked none of the boxes she initially thought most important. “I thought I needed some hotshot East Coast, West Coast, big city dude who came in with all the slick talk,” she tells us. Instead, she found her winner in rural Alabama.
This week, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It was right on,” she tells us. “I mean, it was totally, absolutely true.” We even brought ChatGPT into our conversation in real time, asking it whether Jaci had hired the right business development person, whether Sarah had been fully prepared two years ago to buy back her PR firm, and what’s the best podcast for small business owners. Plus: while we were talking, Jaci asked ChatGPT to evaluate the performance of her co-founder and spouse, MIchael. Let’s just say, it does have some concerns.
This week, Liz Picarazzi tells Sarah Segal that she’s taking another pass at finding a domestic fabricator. Maybe it’s wishful thinking, Liz says, but she’s hoping that now that her business is more established, she just might find an American factory that wants to partner with a growing business and would be eager to help her re-shore her manufacturing. She’s also decided she’s going to keep speaking out about the tariffs despite the hate mail she’s been getting: “I'm not going to be ashamed of manufacturing in Asia,” she tells us. “I had my reasons, and they were very good reasons.” Plus: Sarah talks about how she’s been using AI, including to create her own GPTs, which help her promote her clients. She’s also found a software platform she loves that makes it easier to find and file requests for proposals.
This week, Jay Goltz and Lena McGuire talk about an expense a lot of business owners may not even realize they’re paying. When former employees collect unemployment, they get a check from the government, but then their former employer gets docked. It can add up to real money, and that’s likely to become a bigger issue if the economy deteriorates. Of course, as Jay and Lena discuss, one way to keep your unemployment insurance as low as possible is to do a better job hiring. Jay and Lena also talk about whether it ever makes sense to rehire someone you’ve had to fire. Plus: With Lena’s clients and potential clients putting on the brakes, she’s using this slow period as an opportunity to improve her systems. She’s hoping to avoid a mistake she made last time when she built a business that she was unable to sell.