

21 Hats Podcast
21 Hats
The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they had to lay off employees, how they wound up with way too much inventory, why they don’t have a succession plan, and even why they are concerned about their own mental health. Visit 21hats.com to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.
Episodes
Mentioned books

Mar 24, 2025 • 19min
Dashboard: Don’t Tell Me Your 2024 Financials Aren’t Ready
This week, Tracy Bech, co-author of the 60 Minute CFO, tells us that for a surprising number of business owners, the answer is no, their financial statements for last year have not yet been prepared. And that’s a problem, especially in a year with so much change and so much uncertainty, because it means those businesses have been flying blind for much or all of the first quarter. Many of these owners, Tracy tells us, think that so long as they have cash in their checking account, they’re okay, but that can be a dangerous way to run a business.

Mar 18, 2025 • 45min
I Think We’re in a Recession Now
This week, in Episode 238, Mel Gravely tells Shawn Busse and Jay Goltz that he believes we will eventually find out that the U.S. economy has already slipped into a recession. The funny thing about recessions is that they can start and even end before the GDP numbers make it official, which leads us into a conversation about what businesses can do to prepare for a possible recession. Mel, for example, says his team is checking in on everyone and everything: suppliers, customers, and employees. We also discuss why a lot of pricing models no longer work, why some businesses have never fully recovered from the pandemic, and how Mel turned around a facilities-management business that was losing $1 million a year. Plus: the owners discuss the relative merits of planning to fund your retirement by investing in a 401(k) vs. by selling your business.

Mar 17, 2025 • 37min
Dashboard: Will the Pain, Chaos, and Uncertainty Be Worth It?
This week, Gene Marks explains why he thinks business owners should be patient. Gene says that whatever economic pain they may be experiencing right now will be worth it in the long run, and that’s because he believes President Trump is taking necessary steps to fix the economy and level the international-trade playing field, which will greatly benefit small businesses over time. (Podcast host’s note: I do have a few questions for Gene about that.)

Mar 11, 2025 • 43min
When There’s an Illness in the Family
This week, in episode 237, Jaci Russo tells William Vanderbloemen that she’s a little surprised, given all of the uncertainty in the air, how well her marketing business is holding up. Marketing, as we all know, is often the first thing businesses pull back on. Jaci says her strong results may have something to do with the changes she’s made in the way her agency closes sales. We also get Jaci’s and William’s takes on the conversation we’ve been having about whether owners should consider their employees’ personal circumstances when making HR decisions. But our main topic today is weightier than usual: William’s wife and co-founder Adrienne recently received a cancer diagnosis and has begun treatment. Long-time listeners may recall that William has spoken in past episodes about his efforts to make sure the business can run without him. “And oh my goodness,” he tells us, “how thankful I am that we started that process so long ago.”

Mar 10, 2025 • 20min
Dashboard: ‘We Can’t Keep Up’
This week, Ami Kassar talks about why his company, MultiFunding—despite all of the talk about chaos and uncertainty—has been overwhelmed by businesses looking for help getting funding to grow. We also talk about what the Biden SBA got wrong about small business lending, what the Trump administration is likely to do with the SBA, and the important distinction between loan fraud and bad lending policy.

Mar 4, 2025 • 49min
Our Government Is Doing This to Us
This week, in episode 236, Shawn Busse, Jay Goltz, and Liz Picarazzi talk about the uncertainty coming out of Washington and the stress it's putting on their businesses. Liz, for example, has had to rethink her supply chain and her pricing on an almost daily basis as the tariff situation continues to evolve. Both she and Shawn believe they’ve lost potential clients who’ve been spooked by the uncertainty. The three owners are figuring out ways to cope, but what they find most galling is that none of this had to happen. “It’s like a manufactured recession,” says Jay. Plus: We also talk about Paul Downs’ recent comments that when he had to decide which employees to lay off, he took into consideration personal circumstances such as who just had a kid and who put a down payment on a house. That’s a natural reaction, but is it a good idea? Or is it trying to play God?

Mar 3, 2025 • 21min
Dashboard: What Does the Trump Chaos Mean for Small Businesses?
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.

Feb 25, 2025 • 41min
I Am Comfortable Being Uncomfortable
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.”

Feb 24, 2025 • 26min
Dashboard: Is It Time to Abolish the SBA?
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.

Feb 18, 2025 • 47min
We’re Not Failing Because We’re Idiots
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.