21 Hats Podcast – Details, episodes & analysis

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, 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?

This week, in episode 228, Lena McGuire—in her first appearance as a regular on this podcast—tells Paul Downs and Jaci Russo about her plans to turn her hobby, remodeling homes, into a real business. In just her third full-time year of building Spóca Kitchen & Bath, Lena says she has already experienced both a quick rise in revenue and then a surprising decline, a decline she attributes mostly to marketing issues. One of those issues, she says, is that she refreshed her website and it started producing more prospects—but fewer qualified prospects. That said, Lena is off to an impressive start, having targeted a well-defined niche, having created a clear process to connect homeowners and contractors, and having demonstrated both a real need for her services and an ability to learn from her mistakes. “I don’t look at failure as failing,” she says in a conversation we recorded in December. Plus: Paul tries to explain why his revenue surged 50 percent in 2024. Now there’s a problem we’d all like to have.

This week, in our first Dashboard conversation of 2025, Gene Marks talks about why he and other owners are excited about what they think will be a more business-friendly environment this year. But Gene also warns that tariffs and deportations are likely to drive inflation higher and discourage the Federal Reserve from cutting rates, which may not produce the economic growth owners are expecting. Plus: There are big changes coming to retirement-plan rules that owners should know about.

This week, we take another look back at the conversations we had over the past year, highlighting some of our happiest, smartest, and most insightful exchanges. We discuss whose advice is worth taking, whether any business can be remarkable, which businesses should try EOS, why family businesses can be so vexing, what to do when big businesses refuse to pay small businesses, the challenges of pricing services, the backlash against diversity, and finally the remarkably moving story of the moment that propelled one entrepreneur first to get fired and then to launch a remanufacturing business that would hit $60 million in revenue in less than five years.

There aren’t many places where you can hear entrepreneurs talk about the real-life problems they are confronting right now, today, as they happen—with no guarantee of a happy ending. But those are the conversations I have every week with Shawn Busse of Kinesis, Paul Downs of Paul Downs Cabinetmakers, Jay Goltz of Artists Frame Service, Mel Gravely of Triversity Construction, Jennifer Kerhin of SB Expos & Events, Liz Picarazzi of Citibin, Jaci Russo of BrandRusso, Sarah Segal of Segal Communications, William Vanderbloemen of Vanderbloemen Search Group, and Laura Zander of Jimmy Beans Wool. They come from a wide range of industries and geographies and experiences, but they all share a willingness to talk about not just what they get right but what they’ve learned from getting stuff wrong.

This week, and next week, we take a look back at the conversations we had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges. We discuss topics such as whether the Great Resignation prompted business owners to overreact and overpay employees, whether the anxiety of owning a business ever subsides, what young couples should ask themselves before one of them starts a business, why owners find marketing so difficult, how owners can sell a business that just won’t sell, and what keeps entrepreneurs going when the going gets really tough.

There aren’t many places where you can hear entrepreneurs talk about the real-life problems they are confronting right now, today, as they happen—with no guarantee of a happy ending. But those are the conversations I have every week with Paul Downs of Paul Downs Cabinetmakers, Shawn Busse of Kinesis, Jay Goltz of Artists Frame Service, Mel Gravely of Triversity Construction, Jennifer Kerhin of SB Expos & Events, Liz Picarazzi of Citibin, Jaci Russo of BrandRusso, Sarah Segal of Segal Communications, William Vanderbloemen of Vanderbloemen Search Group, and Laura Zander of Jimmy Beans Wool. They come from a wide range of industries and geographies and experiences, but they all share a willingness to talk about not just what they get right, but what they’ve learned from getting stuff wrong. If listening to one of these highlights makes you want to hear the full episode, that can be accomplished most easily by going to 21hats.com. There you’ll find a transcript of this episode with links to all of the episodes we sample.

This week, in episode 225, Shawn Busse, Jennifer Kerhin, and Jaci Russo talk about how their businesses did this year and what they’re planning for 2025. Jaci and Shawn have been surprised by a surge of new clients in December, which they say never happens. And Jennifer is excited because she’s confident that in the first quarter she will finally exit the Valley of Death—that transitional period growing companies experience when the people and processes that made them successful stop working (AKA No Man’s Land). Along the way, the owners discuss the relative merits of promoting from within vs. hiring from without, how long it should take to onboard senior-level hires, whether it’s better to err on the side of budgeting for too little growth or too much, how they’re training employees to use artificial intelligence, and what Jennifer can do to stop spending so much time writing and pricing proposals.

This week, Tracy Bech, co-author of the “60 Minute CFO,” talks about how business owners can get more comfortable with their financials. Very few people go into business because they’re good at accounting, but that doesn’t mean it’s acceptable to throw up your hands and say, “I’m not a numbers person.” To drive a car, Tracy says, you don’t have to understand how the engine works—but you do have to know how to read a few gauges. Well, the same is true of driving a business, and she’s got a few suggestions.

This week, in episode 224, special guest Karla Trotman explains, step by step, how she has managed to navigate the challenges and opportunities that only a family business can offer. Karla grew up around a manufacturing business, Electro Soft, that her father started, but she never intended to make a career of it. Instead, she found success in corporate America, but over time, she also came to realize the true wealth-building power of owning a business, any business. “It's not a beauty salon,” she says. “It's an asset. It's not a shoe-shine store. It’s an asset.” That realization sent her back to Electro Soft, which thrilled her father. They agreed to work together for three years after which he would retire and she would buy the business. And that’s pretty much what happened—although, as Karla tells us, thanks to some family dynamics that had to be negotiated, the transition didn’t take three years. It took 11 years.