21 Hats Podcast

This week, John Arensmeyer, CEO of Small Business Majority, assesses what he sees happening in Washington. Arensmeyer, who recently took a group of business owners to Capitol Hill where they shared their concerns with Democrats and Republicans alike, says the chaos and uncertainty President Trump has unleashed are a disaster. Along with the tariffs and indications that the economy is slowing, Arensmeyer notes that the proposed cuts to the ACA and Medicaid -- while not generally seen as a business issue -- will have a bigger impact on small businesses than many realize. Plus: with the conversation about renewing the 2017 Trump tax cuts gaining steam, Arensmeyer makes an appeal that will surprise some to scrap the 20-percent deduction for pass-through organizations. He notes that 73 percent of the deduction’s benefits go to just 4.5 percent of pass-through businesses. Instead, he proposes creating a standard deduction that would help far more small businesses.

This week, in episode 235, Jay Goltz, Lena McGuire, and William Vanderbloemen talk about their best days as business owners and their worst days. Not surprisingly, it’s the worst days that often remain the most vivid—both for the pain they inflict and the lessons they bestow. For Lena, it was the day she felt so exhausted and overwhelmed that she knew she had reached her breaking point and had to do something different. For William, it was when the pandemic hit and he had to lay off almost half of his staff in one day, over Zoom. And for Jay, it was realizing that several young employees he’d tried to lift up were just not going to make it. Of course, the most inspiring part of these stories is what the owners did to learn from them and to rise above them. And then there’s the day Lena returned from spending most of this past January unplugged to find that a whole bunch of things had fallen into place during her absence: “My business,” she tells us, “was running without me for the first time in my life. It felt so good.”

This week, Gene Marks suggests it’s time to take a look at whether there’s still a need for the Small Business Administration. Gene, who thinks the SBA has ignored its core market, would shift the agency’s disaster loans to FEMA and its smallbiz lending to the Commerce Department and get rid of most of the other programs -- programs he says most of the business owners he knows are only vaguely aware of and rarely if ever use.

This week, in episode 234, Paul Downs tells Lena McGuire that, because his business has not picked up, he has had to lay off two employees. Paul explains how he chose which employees to let go, including to what extent he considered who has just had a kid and who just put a down payment on a house. We also talk about whether Paul should start experimenting with different ways to attract business or whether he should continue to do what’s worked in the past and try to ride it out. And then there’s this: Paul has managed to do what so many owners strive to do, which is to take himself out of the day-to-day operation of his business. But what does that mean when there’s very little business coming in? How should he be spending his time now? Plus: Lena and Paul respond to a small business subreddit post from a business owner who quit a comfortable job to pursue the idea he just couldn’t get out of his head. Now, he vacillates between thinking his business is going to be huge and thinking he’s made the dumbest mistake of his life, and he wants to know if anyone else has experienced that kind of doubt. I think we know the answer to that one.

This week, at a moment when a lot of businesses are confronting chaos and uncertainty, Shawn Busse talks about how he and Kinesis survived the Great Recession, which was primarily by talking to business owners to better understand their needs and pain points. Shawn’s advice? Create a process to talk to both your existing customers and your dream customers on a regular basis. Ask them open-ended questions, including Shawn’s favorite: What would you do if you could wave a magic wand and make anything happen?

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.