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21 Hats Podcast

21 Hats Podcast

De: 21 Hats
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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.Copyright 21 Hats Economía Gestión y Liderazgo Liderazgo Marketing Marketing y Ventas Política y Gobierno
Episodios
  • How Do You Sell HR to Owners Who Don’t Think They Need It?

    How Do You Sell HR to Owners Who Don’t Think They Need It?
    Apr 14 2026
    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 the same as knowing how owners think about HR. Or how they talk about it. Or what they’re actually willing to pay for it. So for our latest 21 Hats Brainstorm, we brought in a panel of owners to help Sandy pressure test her assumptions, refine her pitch, and figure out what HR looks like in companies where, as one owner puts it, I tell everyone what the plan is, and then I say, “‘If you don't like it, talk to HR.’ And the joke is, I am HR. I am the owner.”

    Along the way, Sandy and the panelists dig into questions like: When does a business really need HR? What does good HR even look like at 10 or 20 employees? And how do you offer structure and support without sounding like the police or, even worse, like an HR person? Because what Sandy is really trying to do is to take a function most owners resist and make it something they actually want.
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    46 m
  • Dashboard: She Built a Business by Learning to Run Her Home

    Dashboard: She Built a Business by Learning to Run Her Home
    Apr 10 2026
    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 argues that households, like businesses, need systems, delegation, and intentional leadership. But she also makes a point that may resonate with a lot of listeners: for women especially, the stakes—and the expectations—are different. This week, Lisa explains what she’s learned about escaping overwhelm and why treating your home like a business might be the key to getting your life back.
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    33 m
  • Are You Pricing for Your Clients or for Your Business?

    Are You Pricing for Your Clients or for Your Business?
    Apr 7 2026
    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 but insists on building in enough margin to stay profitable. It’s a balancing act between values and reality, and not always a comfortable one.

    The conversation gets into practical questions every business eventually faces: Do you raise prices a little every year, or wait until you’re forced to raise them more than just a little? Do you price based on your costs—or your customer’s perceived value? And how do you handle those conversations without damaging relationships you genuinely care about?

    Plus: Liz expects a tariff refund—but isn’t counting on it to help very much. She also explains why she’s stopped flying employees around the country for installations.
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    54 m
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