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PODCAST

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

business entrepreneurship

All Episodes

45:16

Dear ChatGPT: What Are My Blind Spots?

21 Hats Podcast ·

2025/04/29

This week, in Episode 244, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It

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29:27

Dashboard: A Tech Update for Small Business Owners

21 Hats Podcast ·

2025/04/28

This week, Gene Marks highlights some recent tech developments, including: Quickbooks is selling a lifetime version of its software for just $250. Microsoft has reintroduced its somewhat controversial Recall AI tool, which captures and indexes screenshots of user activity every three seconds—a function that is intended to improve cybersecurity but that has raised some interesting questions. Plus: Gene explains how—if you have the time and money—you can now connect the various software platforms you

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48:59

I’d Love to Manufacture in the U.S.

21 Hats Podcast ·

2025/04/22

This week, in Episode 243, Liz Picarazzi tells Sarah Segal that she’s taking another pass at finding a domestic fabricator. Maybe it’s wishful thinking, Liz says, but she’s hoping that now that her business is more established, she just might find an American factory that wants to partner with a growing business and would be eager to help her re-shore her manufacturing. She’s also decided she’s going to keep speaking out about the tariffs despite the hate mail she’s been getting: “I'm not going to

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33:01

Dashboard: Every Business Has a Story to Tell

21 Hats Podcast ·

2025/04/21

But not every business knows how and where to tell it? This week, Sarah Segal talks through what business owners should know about public relations: How can they get better at explaining what they do? How can they figure out what others will find interesting about their business? Should they share their story themselves or reach out to a journalist? If they decide to reach out to a journalist, should they do it themselves or hire a PR person to do it? If they decide to hire a PR person, how much

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39:24

The Hidden Cost of Bad Hiring

21 Hats Podcast ·

2025/04/15

This week, in Episode 242, Jay Goltz and Lena McGuire talk about an expense a lot of business owners may not even realize they’re paying. When former employees collect unemployment, they get a check from the government, but then their former employer gets docked. It can add up to real money, and that’s likely to become a bigger issue if the economy deteriorates. Of course, as Jay and Lena discuss, one way to keep your unemployment insurance as low as possible is to do a better job hiring. Jay and

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25:52

Dashboard: Mitigating the Impact of the Tariffs

21 Hats Podcast ·

2025/04/14

This week, Gene Marks offers some suggestions for how businesses can survive President Trump’s trade war. Those suggestions include exploring free-trade zones, raising prices strategically, scouring the world for alternative suppliers, and getting out of China. Despite all of the disruption and upheaval, Gene continues to believe that the long-term gain will be worth the short-term pain.

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53:06

The Tariff Bill Arrives

21 Hats Podcast ·

2025/04/08

This week, in a conversation recorded on March 27—shortly before Liberation Day, the day Donald Trump announced his so-called reciprocal tariffs—Liz Picarazzi told Shawn Busse and Jaci Russo what it was like to get her most recent tariff bill for a shipment of trash enclosures from China. “I knew what it was going to be, because I had calculated it,” she says, “but to actually see it on paper was terrifying.” And of course it’s only going to get worse now. In our conversation, we discuss a couple of

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23:16

Dashboard: A Fight for Survival

21 Hats Podcast ·

2025/04/07

This week, John Arensmeyer, founder and CEO of Small Business Majority, talks about the unprecedented crisis confronting small businesses. At the same time their business models are being upended by President Trump’s tariffs, business owners are also watching their support infrastructure get decimated by budget cuts. John talks about what owners can do to hunker down, to survive, and to make sure their voices are heard.

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51:02

‘At 5 O’Clock, I’m Going to Send Everybody an Email’

21 Hats Podcast ·

2025/04/01

This week, in episode 240, Paul Downs tells Jaci Russo and Sarah Segal about laying off a third of his workforce. “Here's the problem in a nutshell,” he says. “Last year, January to March, we sold $1.356 million. This year, January to March: $680,000. March is on track to be the worst month I've had since I started taking records.” Paul also tells the owners that he used to have a rainy-day fund for such occasions, but he used it to renovate his house. He does think the layoffs and other cash

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21:21

Dashboard: Smart People Are Hanging on to Their Cash

21 Hats Podcast ·

2025/03/31

The problem, says David Barnett, who helps people buy and sell businesses, is that if we all hang on to our cash, we will definitely have a recession. David, who’s based in Canada, also talks about how the current disruption looks from north of the border, what advice he’s giving to people trying to buy or sell businesses, and where there might be opportunities lurking within the uncertainty.

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41:32

Launching Lyx: ‘Gatorade for Dogs’

21 Hats Podcast ·

2025/03/28

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 Gatorade

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46:48

I Wouldn’t Have Done This Without Covid

21 Hats Podcast ·

2025/03/25

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 the

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18:36

Dashboard: Don’t Tell Me Your 2024 Financials Aren’t...

21 Hats Podcast ·

2025/03/24

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

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45:22

I Think We’re in a Recession Now

21 Hats Podcast ·

2025/03/18

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

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36:48

Dashboard: Will the Pain, Chaos, and Uncertainty Be...

21 Hats Podcast ·

2025/03/17

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.)

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42:42

When There’s an Illness in the Family

21 Hats Podcast ·

2025/03/11

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

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19:46

Dashboard: ‘We Can’t Keep Up’

21 Hats Podcast ·

2025/03/10

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.

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49:24

Our Government Is Doing This to Us

21 Hats Podcast ·

2025/03/04

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

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21:11

Dashboard: What Does the Trump Chaos Mean for Small...

21 Hats Podcast ·

2025/03/03

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

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40:34

I Am Comfortable Being Uncomfortable

21 Hats Podcast ·

2025/02/25

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

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526 results

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