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.
Episodes
May 8, 2026 • 26 mins
Most business owners know they need marketing. What many don’t know is what they should be paying for it—or what they should expect in return. So when an SEO agency proposes a $3,500-a-month plan, how do you assess whether it’s a smart investment or an expensive gamble? Do you know how many new customers it would take to make that spend worthwhile? Do you even have the data to answer that question? This week, Shawn Busse says too m...
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May 5, 2026 • 43 mins
Every business owner looks forward to that big break—the moment that you land a big client or a major retailer, or do something that puts you on a national stage. But those opportunities don’t just reward you. They can also expose you—especially if you have to take on debt or ramp up production or do things you haven’t done before. Four years ago, when Liz Picarazzi won a high-profile installation for her trash enclosures in Times ...
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May 1, 2026 • 50 mins
For years, the Wine School of Philadelphia and PhillyWine LLC coexisted in the genteel world of wine education. Then a trademark dispute turned that quiet coexistence into a legal battle—complete with accusations, lawsuits, and mounting costs.This week, Keith Wallace, founder of the Wine School of Philadelphia, joins me to talk about what happens when a business owner who’s tried to avoid litigation at all costs suddenly finds hims...
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April 28, 2026 • 48 mins
For Lena McGuire, scope creep really can show up around every corner. She’s in the home remodeling business. But for most owners, including Jaci Russo and Ted Wolf, projects that expand out of control can be less visible but just as hard to contain. It’s baked into the job, because every assignment comes with a built-in tradeoff: Protect your margins or protect the relationship. And especially in the early days of a business, when ...
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April 24, 2026 • 24 mins
Despite what we’ve been reading about tariffs and immigration and inflation and health insurance, the macro economy has actually held up better than many economists expected over the past year. Unemployment is low, corporate profits are high, and the stock markets have been setting records. So, this week, I put the question to John Arensmeyer, CEO and founder of Small Business Majority: Are things really that tough for small busine...
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April 21, 2026 • 52 mins
Early on, William Vanderbloemen’s search firm was exactly the kind of business HubSpot, the marketing platform, was built to help. William had a highly specialized audience, his team produced content that his audience needed, and HubSpot helped make sure the right people found it. Back then, he tells Kate Morgan and Jaci Russo, HubSpot’s promise was that it could help a David compete with a Goliath, and that’s what it did for Vande...
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April 17, 2026 • 34 mins
Hiring a full-time marketing team isn’t realistic for a lot of small businesses—but doing nothing may not be an option either. This week, Johnathan Grzybowski explains how Penji, the platform he co-founded, offers a different path: subscription-based access to vetted creatives matched to your specific needs.We talk about how that model actually works in practice, where it fits (and doesn’t) for small businesses, and how Penji manag...
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April 14, 2026 • 45 mins
Sandy Kapell knows HR—just not the version most business owners live with. After years leading human resources for corporations, Sandy launched her own business, Trakehner Leadership, to bring that expertise to companies that need help. And she’s quickly found a big opportunity: Most small businesses don’t have HR departments, but they still have all the same HR challenges.
The catch? Sandy has also realized that knowing HR isn’t th...
The catch? Sandy has also realized that knowing HR isn’t th...
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April 10, 2026 • 32 mins
In her thirties, Lisa Woodruff hit a breaking point—overwhelmed, overweight, and depressed, as she puts it. So she made a radical decision: she quit her job as a school teacher and set out to get her own life in order. What started as a personal reset became a business—Organize 365—built around a simple but powerful idea: running a household isn’t all that different from running a company.In her new book, Escaping Quicksand, Lisa a...
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April 7, 2026 • 54 mins
Pricing a service business sounds straightforward—until you actually have to do it. How much should you charge? What’s reasonable? And what happens when “reasonable” isn’t enough to keep the business healthy? This week, Sarah Segal walks David C. Barnett and Liz Picarazzi through how she thinks about pricing her PR services—why she aims for consistency across clients and why she resists charging based on what the market will bear b...
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April 3, 2026 • 34 mins
Shawn Busse has never been an AI evangelist. If anything, he’s been wary of the hype. But lately, his thinking has started to shift. While it’s still early, Shawn sees AI pushing marketing away from the soul-deadening world of SEO hacks and keyword stuffing—and toward something far more human: real storytelling and authentic brand building. In this week’s Dashboard, he explains what he’s seeing in his own business and with clients,...
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March 31, 2026 • 49 mins
It’s easy to condemn the horror stories coming out of Noma, the celebrated restaurant in Copenhagen. But this week, Jay Goltz, Jennifer Kerhin, and Ted Wolf confront a harder question: How far are the rest of us—business owners in every industry—from crossing the line? Because it’s not just restaurants. Most owners don’t set out to be abusive. They set out to build something great. And somewhere along the way, high standards can st...
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March 27, 2026 • 39 mins
Chris Campbell started his first business at 18 and has since built and sold companies in landscaping, construction, furniture, and marketing. After his most recent exit, he spent years searching for a business to buy—and found nothing. That dead end turned out to be an opening.Instead, Chris and a group of partners—including his wife, Emily—decided to start something from scratch. The result: a plan for Banana Daddy, a high-concep...
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March 24, 2026 • 49 mins
Given everything going on in the world, you might expect a rough start to the year. But for Paul Downs, Jennifer Kerhin, and Jaci Russo, 2026 has actually begun quite well. In fact, Jennifer and Jaci say they’re finally climbing out of what many owners call the Valley of Death—that long stretch when the business depends on you for everything and when it starts to outgrow your people and your systems. Exiting the valley can take a l...
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March 20, 2026 • 45 mins
For most business owners, rewarding employees for doing their jobs well is just common sense. Hit your numbers, get a bonus. Sell more, earn more. Perform better, get paid more. That’s how motivation works…right?This week, management consultant Kelly Allan asks owners to reconsider that assumption. Allan is steeped in the teachings of W. Edwards Deming, the management thinker widely credited with inspiring Japan’s post–World War II...
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March 17, 2026 • 45 mins
It’s already been quite a decade for owners: a pandemic, inflation, tariffs, and now, suddenly, war with Iran—bringing with it the biggest spike in oil prices ever. And looming over everything is the still-uncertain impact of artificial intelligence. This week, David C. Barnett, Jay Goltz, and Ted Wolf talk about how all that uncertainty is shaping the decisions owners are making right now—from whether it’s wise to invest in new eq...
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March 13, 2026 • 21 mins
It does in this sense, says Victor Hwang, founder of Right to Start, an advocacy group that works to expand entrepreneurial opportunity: While starting a business can be daunting, many Americans assume it’s even more daunting than it actually is. For six years, Victor and his organization have tried to address that concern by removing barriers to entry and spreading awareness of entrepreneurial opportunities. In this episode, Victo...
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March 10, 2026 • 43 mins
Despite the waves of uncertainty crashing across the economy, this week we hear from three owners who feel cautiously good about how their year has started. David C. Barnett budgeted for slightly less revenue in 2026, but he’s operating more efficiently and expects to turn a bigger profit. Jaci Russo is hitting her revenue projections—and after implementing a profit-first accounting system, she says the results have been “eye-openi...
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March 6, 2026 • 32 mins
In this sponsored conversation, Mike Butler, CEO of Grasshopper Bank, argues that business owners shouldn’t have to choose between speed and stability when it comes to their bank. Grasshopper has no branches, but it does offer full-service lending — with the quick decisions you might expect from an alternative lender and the rates you’d expect from a traditional one.Butler also explains how the bank is using AI to simplify everyday...
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March 3, 2026 • 42 mins
For the past six years, we’ve done our best to avoid talking politics on this podcast. By focusing on the business realities owners confront every day, we’ve tried to create a space where people with very different perspectives—from different industries and different parts of the country—can still learn from one another. That’s something we take seriously. But we also live in the real world. And lately, the real world has been maki...
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Mark as Played
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