Latest podcast episodes
pisode 231: The Tricky Business of Selling Small Businesses
The Tricky Business of Selling Small Businesses
TIME TO LISTEN: 51:31

This week, special guest David Barnett, who started helping owners buy and sell businesses in 2008, offers some guidance on an often-misunderstood sales process. Early on, David was a business broker. “I sold over three dozen companies for other people,” he tells us, “and it was very interesting and exciting. It was also a terrible business.” So he changed business models but has continued to do pretty much the same work. As a result, he’s amassed a lot of first-hand knowledge, much of which he shares in our conversation, including: why many owners fail to think of their business as an asset, why sellers shouldn’t be too quick to reject earnouts, why buyers should consider making multiple offers for the same business, how buyers can protect against the post-purchase loss of important customers, why businesses are selling for less than they were a couple of years ago, why there may be a smarter way to buy a business than by scouring business-for-sale websites, and why there really isn’t a true market for buying and selling small businesses.

I Think We’re Ready for the Tariffs

This week, 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.

The Power of a Fresh Set of Eyes
TIME TO LISTEN: 46:53

This week, 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.”

We’re Not Saving Lives. We’re Saving Livelihoods
TIME TO LISTEN: 49:57

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?

I’m Looking at an Empty Pipeline
TIME TO LISTEN: 50:32

This week, 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 late 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.

Never miss a 21 Hats Podcast episode
This Is What It Takes to Build a Business, Vol. 3, Part 1
TIME TO LISTEN: 1:13:49

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 Is What It Takes to Build a Business, Vol. 3, Part 2
TIME TO LISTEN: 1:15:33

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.

I’m Out of the Valley of Death
TIME TO LISTEN: 46:30

This week, 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.

It’s Not a Circuit-Board Business. It’s an Asset
TIME TO LISTEN: 51:26

This week, 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.

It's a Pathetic Budget, But We'll Hit It

This week, Shawn Busse, Jay Goltz, and Sarah Segal talk about why they’re not going to hit their numbers for 2024 and what they’re expecting from 2025, especially regarding tariffs, immigration, and regulation. Shawn says his business has been producing and closing fewer leads. “Clearly,” he says, “we’ve gotta change something.” Jay doesn’t think furniture sales will recover until mortgage rates come down, and he’s bracing for tariffs and deportations that he hopes won’t actually come: “I have to believe,” he tells us, “that somebody in government is going to figure out this isn't a good thing.” Sarah, meanwhile, says her revenues are down, but she’s taking solace from the fact that she is ending the year with a stronger book of business than she ended with last year. Plus: the owners discuss what it means that a judge in Texas has blocked the new overtime law. And they offer guidance to a cafe owner who raised her prices only to get hit with another 25-percent price hike from her main supplier, leaving her to wonder whether she should raise prices again or “eat the loss and pray for a miracle.”

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