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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

43:51

We Can’t Afford to Wait on AI

21 Hats Podcast ·

2026/02/26

A lot of business owners are taking a wait-and-see approach with artificial intelligence. They’ve heard the hype—but they’ve also heard about the slop, the hallucinations, and the research suggesting many AI projects fail to deliver. For plenty of owners, that’s reason enough to assume this might be another passing obsession—like Y2K, Clubhouse, or the metaverse—and to sit back until the dust settles.But not these three owners: David C. Barnett, Jaci Russo, and William Vanderbloemen have decided

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25:17

Dashboard: Searching for Some Tariff Certainty

21 Hats Podcast ·

2026/02/24

Yes, says Gene Marks in this week’s Dashboard, the Supreme Court’s tariff decision, while correct, has created a mess. No, you shouldn’t make any plans to spend your tariff refund money. And no, there’s no telling where the Trump administration might be heading. But he does offer this one shred of certainty: For many businesses that have been paying the so-called reciprocal tariffs, if they plan for a 15-percent tariff rate going forward, they’ll probably be in reasonably safe territory.

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36:03

Dashboard: Where Do You Go for Unbiased Exit Advice?

21 Hats Podcast ·

2026/02/20

Sooner or later, most business owners run into the same unsettling question: How do I actually get out of this thing? Pass it to family? Sell to a competitor? To key employees? To private equity? To an ESOP or an Employee Ownership Trust? Or maybe just shut it down?There’s no shortage of advice—but almost all of it comes with strings attached. Most advisors know one path best, and not coincidentally, it’s the path they’re paid to promote. Sorting through the options on your own can feel

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52:47

Hot Seat: Three Owners, No Easy Answers

21 Hats Podcast ·

2026/02/17

Sometimes the best conversations start with a simple question—and then another, and another. This week, we put Kate Morgan, Jaci Russo, and Ted Wolf in the hot seat and fire away: Are you hiring? Are you finding impressive job candidates? What was the worst job you ever had—and did you learn anything from it? Have you bought crypto? If you had $10,000 a month to spend on marketing, where would it go? Should a marketing agency ever turn its marketing over to another marketing agency? What’s holding

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32:57

Dashboard: Where Do You Turn When You’re Stuck?

21 Hats Podcast ·

2026/02/13

Kelly Berry’s introduction to small-business ownership came at a moment when most new parents are focused on something else entirely. She had just come home from the hospital after giving birth when her husband handed her a personal guarantee to sign. He had quit his job to start a business.“So if this fails,” she said, “you’ll be unemployed and we’ll be homeless?”“Yep,” he replied.That moment made the risks of entrepreneurship very real—and it helped set Kelly on the path she’s been on ever since

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46:52

We’re Trying to Outgrow the Valley of Death

21 Hats Podcast ·

2026/02/10

Almost every growing business experiences a moment when success starts creating as many problems as it solves. Sales are up. The team is bigger. The product line is broader. And suddenly, the systems that got you here start to break. That’s where Liz Picarazzi finds herself right now. “We’re in the valley of death,” she says. “And we really need help.” Liz’s company, Citibin, made the most recent Inc. 5000 list, but Citibin has also hit that dangerous in-between stage—too big to run on

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30:38

Dashboard: Why Chasing Growth So Often Backfires

21 Hats Podcast ·

2026/02/06

For most business owners, growth is the goal. More customers. More revenue. Bigger numbers. Bigger opportunities. And often, more pressure. But what if the way most of us think about growth is actually setting us up for trouble? Economist Gary Kunkle has spent years studying what really drives business performance. Not in headlines or case studies—but in large sets of real-world data. And what he’s found is that fast, aggressive growth often creates risks that owners don’t see until it’s too

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50:40

I Can Help with AI. Do Owners Want Help?

21 Hats Podcast ·

2026/02/03

Alan Pentz is convinced a wave of disruption is about to crash into small businesses—and he’s doing everything he can to warn owners before it hits. He’s writing, teaching, consulting, waving the red flag. He’s just not sure anyone is ready to listen. “I don’t know if you’ve seen Don’t Look Up,” he says, “but it’s kind of like that. The asteroid’s coming—and everyone’s still walking around like it’s normal.” In our latest 21 Hats Brainstorm, Alan put his own future on the table. He asked a panel of

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42:03

Dashboard: One Industry Just Got an AI Playbook for...

21 Hats Podcast ·

2026/01/30

Ryan Markewich knows the landscaping business from the inside. He built and sold a successful landscaping company in British Columbia, then spent years coaching owners of all kinds of businesses through the Great Game of Business—helping them understand their numbers, their people, and their decisions. Now he’s a certified advisor with an AI-powered platform called LeanScaper It’s only been around for about a year, and it’s designed specifically for landscaping businesses but it’s growing quickly

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46:29

I Expect to Grow This Year. Should I Hire Now?

21 Hats Podcast ·

2026/01/27

Things are suddenly moving fast at Sarah Segal’s San Francisco PR firm. Several new clients look likely to sign on, and for the first time in a while, growth feels real. Which leaves Sarah with a familiar, nerve-racking question: Do you hire before the work arrives—or wait until the revenue is actually in the door? If she hires now, she may have to cut her own pay until the new business materializes. And there’s no guarantee it will. She still remembers the last downturn, when she had to lay off

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48:49

Dashboard: A Grand Experiment in Buying and Building...

21 Hats Podcast ·

2026/01/23

Over the past six years, Teamshares has quietly been running an ambitious experiment in small-business ownership. The company has bought some 90 businesses—promising never to sell them—and then converted those companies to employee ownership. Even amid the uncertainty of 2025, those businesses generated more than $400 million in revenue and about $60 million in profit, with a surprisingly low failure rate and unusually high employee retention. This week, Michael Brown, co-founder and CEO of

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46:31

I’m Looking for an Exit

21 Hats Podcast ·

2026/01/20

Six years ago, Kate Morgan walked away from the sale of her business just days before closing. Since then, she’s endured some rough stretches, fighting through the pandemic and a slump in the software sector where many of her clients live. She’s managed to stay profitable, and she sees lots of opportunity ahead, but the grind has worn her down. After years of pushing, adapting, and holding on, she says she’s had enough. She believes a strategic sale makes the most sense, and she’s working her

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31:43

Dashboard: Why 2026 Will Be a Big Year for Small...

21 Hats Podcast ·

2026/01/16

This week, Gene Marks makes the case for optimism. There are all sorts of obvious issues to be concerned about but Gene cites a series of reasons his clients are expecting good things. Chief among them are a series of tax cuts that are coming on line and that are likely to provide more stimulus than many people are expecting. He also expects inflation to moderate and interest rates to fall enough to help out the housing and construction industries. Plus: What business owners need to know about the

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48:57

Do Business Owners Really Want Balance?

21 Hats Podcast ·

2026/01/13

Most business owners say they do. They tell themselves they just need to get through this one crisis, this one launch, this one quarter—and then life will settle down. But what if that’s not actually the goal? This week, Mel Gravely, Lena McGuire, and Ted Wolf talk candidly about what it really takes to build a business—and about whether balance is something owners are truly striving for or simply something they feel they’re supposed to want. “I gotta tell you,” says Mel, “I just don't know if

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28:13

Dashboard: No Text Book Can Prepare You for This

21 Hats Podcast ·

2026/01/09

This week, Karla Trotman, owner of Electro Soft, a contract manufacturing business outside of Philadelphia, talks about the series of contradictions and tough calls she confronted in 2025. It started with the chaos of the tariffs, which you might think would have helped a domestic manufacturer but which led to suppliers charging more and to customers pulling back and to Karla feeling beaten up by her advisory board, which wanted her to reduce expenses and headcount.But Karla chose a different

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51:48

The Old Rules of Hiring Are No Longer Working

21 Hats Podcast ·

2026/01/06

For years, business owners have been told to follow a familiar playbook when it comes to hiring: Take your time. Be selective. Hire slow, fire fast. But more and more owners are discovering that those rules don’t fit the reality they’re facing right now. This week, William Vanderbloemen says employers can no longer indulge the luxury of hiring slow. “The shortest sermon I’ve got,” says the former pastor, “is candidates are more fickle than ever, and owners need to realize that.” Paul Downs says he’s

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36:38

Dashboard: This Company Covers All of Its Employees’...

21 Hats Podcast ·

2026/01/02

This week, Adam Russo, co-founder and owner of The Phia Group, explains how his company helps employers reduce their healthcare expenses. The key, he says, is to educate and incentivize employees to be smarter about how they purchase health care—without compromising on the quality of the care. That, he says, is how he’s able to offer employees who’ve been with Phia for five years care that is entirely free: no deductibles, no co-pays. Many of his clients are big companies that self-fund their health

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62:55

Do You Have the Stomach for This? 2025 in Review, Part 2

21 Hats Podcast ·

2025/12/30

This week, we take another look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Laura Zander on how she got the price she wanted to sell Jimmy Beans Wool, Liz Picarazzi on her confrontation with a grizzly bear, Jay Goltz on why he just might be a good candidate to turn his business into a worker cooperative, Mel Gravely on why he sold his facilities-management business as soon as it became

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20:12

Dashboard: You Can Still Save on 2025 Taxes!

21 Hats Podcast ·

2025/12/26

This week, Gene Marks tells us it’s late, but it’s not too late to reduce this year’s tax bill. There are still steps you can take, including writing off receivables and inventory and kicking money into a retirement plan. You might even be able to save money on your taxes from previous years if you used the research-and-development tax depreciation. The GOP tax law allows you to go back and retroactively take the full R&D deduction in the first year rather than amortizing it over five years—but

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70:35

Do You Have the Stomach for This? 2025 in Review, Part 1

21 Hats Podcast ·

2025/12/23

This week—and next week—we take a look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Paul Downs on how he diced which employees to lay off, Jennifer Kerhin on asking ChatGPT to review her performance as CEO, Kate Morgan on why she’s been reluctant to raise her prices, Liz Picarazzi on her search for a domestic manufacturer for her trash enclosures, Ari Weinzweig on why Zingerman’s charges so much

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511 results

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