21 Hats Podcast - podcast cover

21 Hats Podcast

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.
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Episodes

Launching Lyx: ‘Gatorade for Dogs’

In this week’s bonus episode, Dylan Jones shares his entrepreneurial journey, which includes serving in the Air Force, a Master’s degree in business analytics, a failed software business, and a brand new consumer packaged goods business that draws on his knowledge of military working dogs—most importantly that it can be a challenge to keep military dogs (and pets) hydrated. Jones came up with a solution and started selling it at farmers markets where he would simply announce, “Hey, I have Gatora...

Mar 28, 202542 min

I Wouldn’t Have Done This Without Covid

This week, five years after Covid arrived and as we find ourselves in another period of dramatic uncertainty, Jennifer Kerhin, Lena McGuire, and Sarah Segal talk about the advances their businesses might never have made had it not been for the pandemic, from the technology they use, to the people they employ, to the systems they’ve created. “It was very scary early on,” says Jennifer, “but it was transformational.” Plus: Do you hire full-time employees in anticipation of more business or when th...

Mar 25, 202547 minEp. 239

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, b...

Mar 24, 202519 min

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. W...

Mar 18, 202545 minEp. 238

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 17, 202537 min

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 ...

Mar 11, 202543 minEp. 237

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 10, 202520 min

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...

Mar 04, 202549 minEp. 236

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 busines...

Mar 03, 202521 min

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 ...

Feb 25, 202541 minEp. 235

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 24, 202526 min

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’...

Feb 18, 202547 minEp. 234

Dashboard: What If You Could Wave a Magic Wand?

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 anyth...

Feb 17, 202524 min

Everything Liz, Jaci, and Sarah Wanted to Know About Tax

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 ow...

Feb 11, 202545 minEp. 233

Dashboard: Gene Marks Has an Ambitious Plan to Do Less

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...

Feb 10, 202525 min

Most People Don’t Have the Stomach for This

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...

Feb 04, 202548 minEp. 232

Dashboard: A Warning for Small Businesses

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, unc...

Feb 03, 202527 min

The Tricky Business of Selling Small Businesses

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, m...

Jan 28, 202552 minEp. 231

Dashboard: Is Small Business Optimism Eroding?

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 Kell...

Jan 27, 202525 min

I Think We’re Ready for the Tariffs

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 ...

Jan 21, 202553 minEp. 230

Dashboard: How Do I Get ChatGPT to Notice Me?

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....

Jan 20, 202532 min

The Power of a Fresh Set of Eyes

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...

Jan 14, 202547 minEp. 229

Dashboard: You Have to Make Your Own Weather

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 focusin...

Jan 13, 202530 min

We’re Not Saving Lives. We’re Saving Livelihoods

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 h...

Jan 10, 202550 min

I’m Looking at an Empty Pipeline

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 start...

Jan 07, 202551 minEp. 228

Dashboard: Are Business Owners Too Optimistic About 2025?

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.

Jan 06, 202524 min

This Is What It Takes to Build a Business, Vol. 3, Part 2

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 ...

Dec 31, 20241 hr 16 minEp. 227

This Is What It Takes to Build a Business, Vol. 3, Part 1

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 busines...

Dec 24, 20241 hr 14 minEp. 226

I’m Out of the Valley of Death

This week, in episode 225, 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 (AK...

Dec 17, 202447 minEp. 225

Dashboard: Margins, Metrics, and Cash Flow

This week, Tracy Bech, co-author of the “60 Minute CFO,” talks about how business owners can get more comfortable with their financials. Very few people go into business because they’re good at accounting, but that doesn’t mean it’s acceptable to throw up your hands and say, “I’m not a numbers person.” To drive a car, Tracy says, you don’t have to understand how the engine works—but you do have to know how to read a few gauges. Well, the same is true of driving a business, and she’s got a few su...

Dec 16, 202425 min
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