21 Hats Podcast

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 businesses. How can a community do that? Step one, she says, is to find local manufacturers, talk to them, and find out what they need. Go figure!

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-dominated industry. This is a true bootstrap story. Channon’s numbers are modest enough that she still does most of her own fulfillment at night after her day job as a banker—and she loves it. “Every time I get an order,” she says, “I feel like I'm wrapping a Christmas present. I'm just so excited that somebody wants something that I've created.” Plus: Paul Downs checks in with an update. After posting his best year ever in 2024, he was blindsided when sales suddenly stalled earlier this year, forcing him to lay off a third of his employees. Sales have since rebounded, but now he’s staring at a backlog and a different dilemma: Does he hire aggressively to meet the higher demand—or play it safe until he sees how 2026 begins?

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 change the risk profile of a business. And perhaps the most under-discussed challenge of all: not all employees embrace employee ownership. Some see it as little more than a glorified retirement plan. And here’s the thing: an ESOP can be a far riskier retirement plan than many understand. They differ from 401(k)s in that there's no regulation requiring an ESOP to sequester its employees’ retirement funds. If the company fails—and like all businesses, ESOPs do fail—those nest eggs can vanish. Kris and Justin explain how they’ve addressed these issues and what they might do differently if they were starting over. They also emphasize an important point: Not all ESOPs are created equal. “If you’ve seen one ESOP,” Justin likes to say, “you’ve seen one ESOP.”

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 who are private-equity backed. Those members represented half the organization’s revenue at the time of the decision. I also ask Julian which is the better path: learning a trade and building a business or buying a business and figuring out the trade.

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 thought it was the worst day of his business life. Turns out, he says, it was his best. Because that disaster forced him to rethink everything—how decisions get made, how profits get shared, how responsibility gets distributed. And that shift led not only to healthy growth but eventually to the kind of exit business owners dream about. That experience continues to inform the work Ted does today, helping companies integrate AI into their operations. The hard part, he tells Jennifer Kerhin, isn’t the technology—it’s the people. It’s managing the change, the fear, the implications. The technology matters, too. Ted and Jennifer also discuss whether small businesses should try to retrofit AI into their current tech stacks—or whether the smarter move, painful as it may be, is to start fresh.

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 owners are ill-prepared to confront. He’s planning to address that in his writing. As for himself, Josh tells us that he’s not afraid of death, but he is afraid of retirement.

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 retirement age and may not be around to reap decades of appreciation? Is buying the business still a good idea? Meanwhile, Liz and Lena also compare notes on their ever-evolving tariff challenges. One thing Lena has observed is that some owners in her industry have just had it. They don’t want to deal with the uncertainty, and they’re just packing it in: “We're going to see who survives all this,” she says, “and I want to be a survivor.” Plus: Liz has her first “aha” moment with an AI tool her team built, one that’s already helping convert sales.

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 needs is simply not produced here. And those imports are being taxed at a very high rate. At the moment, Shugar is waiting to hear whether Trump will indeed, as he has threatened, slap an additional 100-percent tariff on imports from China, which Shugar says could force him to shut down. The threat alone means that he can’t make plans two weeks out -- let alone start thinking about next year.

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, she charges, in her words, “a boatload of cash.” Plus: we dive into another tricky owner decision: how to structure bonus plans that truly drive retention. David is weighing a deferred bonus approach, where payouts happen over several years. It’s a proven way to keep people around, but he wonders: Do you really want employees who’d otherwise leave to stay just for the money? Also, when valued employees get an offer, do you counter-offer? And if they leave, do you tell them they can always come back?