21 Hats Podcast

This week, John Arensmeyer—CEO of Small Business Majority and our man in Washington—stops by to talk about the Trump administration's first week and what it means for business owners. It’s very early of course, but the administration is moving quickly on many fronts and some issues, John tells us, have businesses in his network concerned. Not surprisingly, those issues include tariffs and immigration. We also talk about the fate of TikTok and this week’s confirmation hearing for SBA nominee Kelly Loeffler.

This week, in episode 230, Liz Picarazzi tells Paul Downs and Sarah Segal that after a year of anxiety, she’s eager to find out what Donald Trump is really going to do about tariffs. Whatever it is, she thinks she’s prepared enough options to survive. “If your tax rate went from 11 percent to 60 percent,” she says, “I think most of us would be pretty freaked out, and I am, but I'm a little bit less so because of this work that we've done to be ready.” Paul, meanwhile, thinks there’s some chance his business could benefit from the tariffs—although he’s far more focused on his business’ very slow start to 2025. “It’s a little bit scary, frankly,” he tells us. And Sarah has been dealing with the pain of having to let one staffer go and the disappointment of having one of her senior people choose to go.

Last week on Dashboard, Shawn Busse said he thinks that trying to make your business discoverable on AI bots is “a fool’s errand.” So, this week, I invited Sean Campbell, CEO of Cascade Insights, a market research firm, to offer an opposing view. In our conversation, Sean talks about what businesses should be thinking about and doing to prepare for the not-too-distant day when most people turn to a generative AI tool like ChatGPT to find products and services.

This week, in episode 229, Jay Goltz, Jaci Russo, and William Vanderbloemen discuss their experiences bringing in outside consultants to review their business operations. Before the holidays, Lou Mosca, who runs American Management Services, offered to have his team take a look at any of the businesses owned by the regulars on this podcast. Jaci took Lou up on the offer, and she shares here what she learned. Jay declined the offer, and he explains why he declined it. William, meanwhile, has had two experiences with consultants that went well—and one he won’t talk about. Plus: The three owners assess what they think the coming mix of regulatory changes, tax cuts, increased tariffs, and mass deportations might mean for their businesses. They also offer their views of the state laws that forbid businesses to ask job candidates about their salary histories. “I'm sorry,” William says, “but if you believe what people tell you when you say, ‘Tell me how much you're making,’ you need to stop.”

For business owners, the challenges of digital marketing seem to just get bigger. PIck a platform, any platform: the odds of success have gotten smaller and smaller. Even TikTok, where many small businesses have built followings, may not survive the month. So what’s a business owner to do? This week, Shawn Busse offers an alternative. First of all, Shawn does not believe that figuring out how to be discovered on AI bots is the answer. “I think that’s a fool’s errand,” he says. Instead of focusing on channels and tactics, he encourages owners to tell their story and build a brand. That’s not a simple task, but Shawn shares an impressive case study of an organization that, in his words, is “making its own weather.”

In this week’s bonus episode, David Billstrom and Matt Raker, two business leaders who have played important roles in Western North Carolina’s attempt to recover from Hurricane Helene, talk about what we’re still figuring out about disaster recovery. The world tends to move on pretty quickly after an event, but the economic recovery can drag on for years. And it can be especially devastating for smaller businesses. The data from other catastrophic storms, David tells us, suggest that more than half of the small businesses in the area could be gone within a year. And of course those odds are not improved when insurance companies find ways not to pay claims and when government takes too long to respond. As you’ll hear, at the time we recorded the conversation in mid-December, the U.S. Congress still had not appropriated funds to help. That did finally happen at the end of December, but it’s still tempting to ask: Shouldn’t we be getting better at this?

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.