21 Hats Podcast

This week, Gene Marks tells us it’s late, but it’s not too late to reduce this year’s tax bill. There are still steps you can take, including writing off receivables and inventory and kicking money into a retirement plan. You might even be able to save money on your taxes from previous years if you used the research-and-development tax depreciation. The GOP tax law allows you to go back and retroactively take the full R&D deduction in the first year rather than amortizing it over five years—but check with your accountant. Gene also says that it’s no longer a slam dunk that a pass-through structure is best for smaller businesses—but again, check with your accountant!

This week—and next week—we take a look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Paul Downs on how he diced which employees to lay off, Jennifer Kerhin on asking ChatGPT to review her performance as CEO, Kate Morgan on why she’s been reluctant to raise her prices, Liz Picarazzi on her search for a domestic manufacturer for her trash enclosures, Ari Weinzweig on why Zingerman’s charges so much for a hamburger, and David C. Barnett on why your business is probably worth more to you owning it than selling it.

As the year comes to a close, I often reach out to John Arensmeyer, who is founder and CEO of Small Business Majority, to get his take on the state of small businesses in America. The picture John paints this year, based on his own observations as well as a recent survey, is not pretty. He points to a host of issues -- health insurance, tariffs, immigration, cuts to federal programs -- every one of which can represent an existential threat to a business. John does note, however, that through it all, owners appear to remain surprisingly optimistic heading into 2026—even if that optimism speaks more to the resilience of business owners than it does to the economic outlook.

This week, special guest Rich Jordan takes us inside a marketing challenge presented by his successful acquisition of home services businesses. Do you keep the legacy names of those businesses to preserve local trust—at the cost of running a fragmented, inefficient marketing operation? Do you take the strongest brand you own and roll it out everywhere, even if it may not translate from one community to the next? Or do you wipe the slate clean and create an entirely new brand to unify the whole operation—knowing that it means walking away from money you’ve already sunk into branding your biggest location? In a conversation with Shawn Busse and Jay Goltz, Rich walks through how he wrestled with those choices, why he ultimately made the call he did, and what he learned along the way. His takeaways included that there are still people who listen to radio, that an authentic story can compete with private equity, and that it is possible to find a marketing agency that will align its interests with yours.

Most business owners know they should build a forecast for 2026. But many won’t—because it feels intimidating and time-consuming, and let’s be honest, it’s almost guaranteed to be inaccurate. This week, Tracy Bech, founder of The 60 Minute CFO, makes the case for why you should do it anyway. Tracy breaks the process down into three simple steps, shows how even a rough forecast can change the way you run your business, and explains how her free 60 Minute CFO Custom GPT can speed things up and expand your financial analysis. Her point isn’t that you can predict the future. It’s that you need a clear, flexible model to see whether your business is on track—or drifting somewhere you never intended to go.

This week, in Episode 273, David C. Barnett, Paul Downs, and Sarah Segal tackle health insurance, one of the least enjoyable issues business owners confront. It’s renewal season, and the three owners are seeing different systems, different pressures, but similar frustrations. Paul tells us he’s facing the largest premium increases he’s seen since the Affordable Care Act—double-digit hikes that will cost him an extra $15,000 to $25,000 next year. Sarah hasn’t received her numbers yet, but she’s preparing for the worst. And David gives us a cross-border view from Canada, where universal coverage eliminates the pricing drama but introduces its own set of complications. It’s a candid conversation about what’s responsible, what’s sustainable, and what business owners are supposed to do when the numbers don’t leave good options. Plus: We also talk about what it takes to get a business ready to be sold. While BizBuySell recently reported that more owners are looking to get out—even if it means dropping their asking price—that’s not exactly what David is seeing in the marketplace. “The truth is that small businesses sell for relatively low multiples of cash flow,” he says. “And so, the real benefit is not actually in the exit. It's in the owning.”

This week, Brandon Gray, a partner with CRI Simple Numbers, talks about how his firm tracks the performance of what he calls the entrepreneurial economy. As we all know, what’s happening on Wall Street doesn’t always reflect what’s happening on Main Street, which is why Simple Numbers tracks the performance of 100 smaller businesses. Right now, Brandon says, the performance of those businesses isn’t looking great, which doesn’t necessarily bode well for 2026. How should an individual owner make use of that information? Brandon has some suggestions.

This week, we’re replaying one of my favorite conversations of the year, a Q&A session we recorded in May at our 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of Zingerman’s Community of Businesses. If you’ve already listened to our conversation with Ari, I encourage you to listen again. It’s worth it.

And if you haven’t heard it, well, you’re in for a treat. Much of the discussion focused on a topic that haunts just about every business owner, and that’s pricing. Specifically, Ari talked about how he learned to charge enough to run a healthy business and why he’d rather go out of business charging what Zingerman’s needs to charge than go out of business never knowing whether customers would have paid the true cost of great food and great service. (Spoiler alert: They have not gone out of business.)

Not surprisingly, the 21 Hats Live participants had lots of questions for Ari, including how he and his partners decide whether to launch a new business, how he and co-founder Paul Saginaw have maintained their partnership for more than 40 years, how he and Paul are approaching succession, and whether he thinks of himself as successful, which prompted Ari to share that his mother never stopped pleading with him to take the LSAT. You know, just in case.

We’re re-playing the episode in part because we took Thanksgiving week off from recording but also because it offers a little taste of what it’s like to attend a 21 Hats Live event. As you may have seen in the Morning Report, I’ve just announced that our fourth annual in-person event will take place in Cincinnati in May. Once again, it will be a terrific opportunity to connect with others who understand what it takes to build a business. If you’ve ever wished you could spend more time with people who really get what you’re going through, this is your chance. We will have peer group conversations on topics you help pick. We’ll get VIP tours of iconic local businesses. We’ll eat good food. We’ll build relationships. And we’ll leave inspired.

But spots are limited. For more information and to register, please check the newsletter I sent out on Sunday. Or shoot me an email, and I’ll make sure you get the invite. You can reach me at [email protected].

This week, Rob Levin, who is co-founder of WorkBetterNow and who has just published a new book, the “New Talent Playbook,” talks about what he considers to be a talent crisis for small businesses. As Rob points out, you might think hiring would be easy these days given all of the recent corporate layoffs—but the people leaving big businesses are probably not the right hires for smaller businesses. Instead, Rob offers a step-by-step approach that emphasizes building a healthy culture where people want to work.

This week, in Episode 272, Liz Picarazzi and Jaci Russo compare notes with Ted Wolf on their very different journeys to integrate generative AI into their businesses. For Liz, it’s been frustrating. She resisted AI at first—but while she’s ready to go now, her COO, who also happens to be her husband, still isn’t there. That’s one reason Liz says she feels as though she’s been spinning her wheels. Jaci’s path couldn’t have been more different. She jumped in more than two years ago, took every course she could find, and now has custom GPTs talking to custom GPTs talking to custom GPTs. The AI tool she built delivers 10 fresh, fully vetted prospects to her inbox every morning. “It will find the person in charge of marketing,” she says. “It will find their LinkedIn profile. It will find the company website. It will find their competitors.” And it has already produced two new clients. Plus: As this especially challenging year winds down, Liz, Jaci, and Ted reflect on where their businesses hit expectations and where they fell short. Jaci notes a sales hire that failed. “I would have liked to have not spent the money on that person and had this epiphany without the pain,” she says, “but I think those two things just go hand in hand.” Liz cites her $400,000 tariff bill: “It really hurts, and it makes me angry,” she tells us. “But in terms of revenue, we’re doing well, I gotta admit. Thank God for New York City rats and trash.”