21 Hats Podcast

This week, in episode 233, we brought in a tax expert, Juliann Rowe of CRI Simple Numbers, to explain everything Liz Picarazzi, Jaci Russo, and Sarah Segal ever wanted to know about tax (but weren’t sure whom to ask). For example, should owners run their own compensation through payroll? Well, maybe, maybe not. We quickly learned that the answer for Sarah is different from the answer for Liz, which is why a lot of owners get this one wrong. Among the other issues we cover: Isn’t it easier for owners to pay themselves through payroll so they don’t have to worry about paying quarterly estimates? Can the owner take a draw to cover her income tax payment? If the owner isn’t running her own compensation through payroll, how much can she contribute to her 401(k)? Is it even a good idea for owners to tie up their money in a retirement account? What’s the best way for an internal bookkeeper and an external CPA to work together? And also, why did Liz, Jaci, and Sarah ask me to bring in a tax expert who is a woman? I kind of knew the answer to that one, but I decided to ask anyway.

This week, Gene tells us that he’s been spending too much time doing and not enough time thinking. So he’s made a plan to free up some time to focus on the more important, big picture issues that sometimes get lost in the day-to-day. How will he free up the time? By getting out of the office more, by leaning more into tech, and by being more deliberate about how much time he spends with customers. Plus: Gene also shares a few highlights (and lowlights) from a Microsoft AI trade show -- including the Microsoft employees who don’t trust their own AI.

This week, in episode 232, Paul Downs tells Shawn Busse and Jay Goltz why he isn’t sleeping and why he has stopped paying himself. After having his best year ever in 2024, Paul has seen his inquiries fall precipitously. His backlog of work is dwindling, and he’s concluded he needs to take some painful steps. “I'm coming to the realization,” he tells us, “that I need to do something that involves reducing staff.” Paul’s not sure why his business is off, but he suspects it may have something to do with the chaos in Washington. He also tells us that the big marketing initiative he undertook a couple of years ago, when he decided to try to reach a slightly different target market, has yet to pay off the way he’d hoped. But he hasn’t given up on it. Plus: We also address an increasingly common issue for business owners: What do you do when employees come to work high?

This week, having long encouraged small business owners to support President Trump’s pro-business agenda, Gene Marks says those policies are likely to produce a tough year for owners. In a conversation recorded shortly after the president announced that tariffs on Canada, Mexico, and China are about to take effect, Gene tells us that he thinks business owners are too optimistic about the immediate impact of the Trump policies. In the year ahead, Gene expects those policies to produce change, uncertainty, and pain. That said, he still supports the policies.

This week, in episode 231, 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.

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.”