21 Hats Podcast

Most business owners say they do. They tell themselves they just need to get through this one crisis, this one launch, this one quarter—and then life will settle down. But what if that’s not actually the goal? This week, Mel Gravely, Lena McGuire, and Ted Wolf talk candidly about what it really takes to build a business—and about whether balance is something owners are truly striving for or simply...

This week, Karla Trotman, owner of Electro Soft, a contract manufacturing business outside of Philadelphia, talks about the series of contradictions and tough calls she confronted in 2025. It started with the chaos of the tariffs, which you might think would have helped a domestic manufacturer but which led to suppliers charging more and to customers pulling back and to Karla feeling beaten up by...

For years, business owners have been told to follow a familiar playbook when it comes to hiring: Take your time. Be selective. Hire slow, fire fast. But more and more owners are discovering that those rules don’t fit the reality they’re facing right now. This week, William Vanderbloemen says employers can no longer indulge the luxury of hiring slow. “The shortest sermon I’ve got,” says the former...

This week, Adam Russo, co-founder and owner of The Phia Group , explains how his company helps employers reduce their healthcare expenses. The key, he says, is to educate and incentivize employees to be smarter about how they purchase health care—without compromising on the quality of the care. That, he says, is how he’s able to offer employees who’ve been with Phia for five years care that is ent...

This week, we take another look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Laura Zander on how she got the price she wanted to sell Jimmy Beans Wool, Liz Picarazzi on her confrontation with a grizzly bear, Jay Goltz on why he just might be a good candidate to turn his business into a worker...

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 retroa...

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 searc...

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 o...

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 communi...

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...

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 wil...

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...

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 o...

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....

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....

That’s the conclusion of Ilana Preuss, who is founder and CEO of Recast City and who believes that the way to bring back America’s Main Streets, downtowns, and local economies is through small-scale manufacturing. While traditional economic development focuses on what Preuss calls big-game hunting--recruiting big, established companies--she favors looking for ways to support even the smallest of b...

This week, in Episode 271, we welcome another new voice to the podcast: Channon Kennedy, who takes us inside the side hustle that’s become her second full-time job. Channon is the inventor and patent holder of the Morgan Square, a clever measuring tool— here’s a demonstration —that’s racking up awards, expanding its distribution, and carving out space for a woman founder in a traditionally male-do...

Yes, says Gene Marks, it’s easy to make fun of all of the ways in which AI chatbots can fail (don’t even think about asking them to create an image of a Yorkshire Terrier hitting a homerun), but that’s no excuse to sit on the sidelines. Get the paid version. Get some training. Get your employees some training. And get to work. On what? Gene gives some examples of his favorite use cases.

This week, in Episode 270, we dig into employee ownership with two people who’ve lived it: Kris Maynard and Justin Jordan of Cathedral Holdings , a 100-percent employee-owned ESOP since 2011. Kris and Justin are enthusiastic proponents of ESOPs, but they’re also candid about what can go wrong. Yes, ESOPs come with big tax advantages. But the transaction can be complex. The debt can fundamentally c...

This week, Julian Scadden explains how the organization he runs, Nexstar Network , helps the owners of plumbing, HVAC, and electrical firms become better business owners. Along the way, he discusses the challenges home-service businesses are confronting, why Nexstar is member-owned (and what that means), and an intriguing decision he made recently to part ways with the 30 percent of his members wh...

This week, in Episode 269, we welcome Ted Wolf, co-founder of Guidewise , as the newest regular member of the 21 Hats Podcast crew—and Ted arrives with a pretty good story. Back when he was building his IT staffing business with his brother, a senior employee walked out. But he didn’t walk out alone—he took key employees, key accounts, and 40 percent of the company’s revenue. At the time, Ted thou...

Josh Patrick’s first act was building and eventually selling a successful vending-machine business. His second act was building a thriving consulting practice in which he helped other business owners learn the lessons he’d learned the hard way. In our latest Dashboard episode, Josh, a cancer survivor whose cancer has returned, is exploring two experiences—retirement and death—that he believes most...

This week, in episode 268, Jay Goltz, Lena McGuire, and Liz Picarazzi discuss a common concern: When does it make sense to buy a building for your business? Under the right circumstances—say, with an SBA loan, a good location, and a little luck—the real estate could end up being worth more than the business itself. But what if the business is just getting started? Or what if the owner is nearing r...

This week, Greg Shugar, owner of Beau Ties , a men’s accessories business, explains how the tariffs have the potential to destroy the very businesses they are supposed to protect. As Shugar points out, President Trump has said all along that if you make it here, you won’t have to pay the tariffs. Well, Beau Ties makes it here -- but it has to import fabric from overseas because the silk fabric it...

This week, in episode 267, David C. Barnett, Kate Morgan, and Sarah Segal tackle a challenge every owner who sells services eventually faces: Clients want to hire you, but you want them to understand they’ll mostly be working with your team. How do you make that clear without scaring them off? For some, it’s a delicate balancing act. For Kate, it’s simple: if a client insists on her personal time,...