21 Hats Podcast

21 Hats
  • 5.0 (34)
  • Entrepreneurship
  • Weekly

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.

  1. 2h ago

    She Sold Out at Three Trade Shows. Why Was She Disappointed?

    Channon Kennedy spent between $15,000 and $20,000 exhibiting her Morgan Square measuring tool at five trade shows in eight weeks. She sold out at three of them, had her best sales day ever at another, and made valuable connections with potential distributors. And yet, she was disappointed. This week, Channon compares notes with Jennifer Kerhin, whose company manages trade shows, and Sarah Segal, whose PR firm helps clients make the most of them. Jennifer suggests that Channon may need to rethink how she measures success, while Sarah explains how exhibitors can get more out of their investment by attracting attention before, during, and even after a show. Plus: We learn that Sarah and Jennifer have very different philosophies about rehiring former employees. Sarah sees an opportunity to bring back people who already know her business and have gained valuable experience elsewhere. Jennifer has done that four times, but she says she’s not doing it again. And Sarah explains why, after a year of rapid growth, she's planning to be more selective about the clients she takes on in 2027. She's learning that sometimes the most important thing an owner can do is say, "No." The episode is brought to you by Grasshopper Bank. Show Notes: Get a free trial of the 21 Hats Morning Report. If you like what you hear on the 21 Hats Podcast, please consider joining our monthly Founding Member mastermind. It’s a lot like the podcast — business owners comparing notes on what’s working and what isn’t — except that what’s said in the mastermind stays in the mastermind. Interested? Send me an email and I’ll invite you to a session as my guest.

  2. 4d ago

    Dashboard: Follow the Money. Then Try to Get Paid

    When Jessica Johnson-Cope took over her family's security business in 2008, she inherited a company with just 16 employees and no succession plan. Today, Johnson Security Bureau has more than 150 employees operating in four states, generates $10 million to $15 million a year, and gets about 80 percent of its revenue from government contracts. Along the way, Jessica has learned some valuable lessons: Follow the money to find opportunities. Don't get fixated on landing the biggest contracts. Pay attention to the people in the room who aren't doing the talking. And just because you've done the work doesn't mean you're going to get paid anytime soon.This week, Jessica tells us how she rebuilt the family business, why she's gotten better at saying no, and how her Black- and woman-owned business, which relies heavily on government contracts, has continued to thrive in the era of DOGE and the DEI backlash. Surprisingly, she says, neither has had much impact on her business—although government staffing cuts have complicated the process of getting paid, and she knows that some people assume she's won business because of her race or gender rather than her company's performance. The episode is brought to you by Grasshopper Bank.

  3. Nov 3

    We Want to Grow. But at What Cost?

    This week, Rob Levin, Liz Picarazzi, and Jaci Russo talk about what they're planning for 2027—and how much they're willing to invest to achieve their goals. Rob explains why, just days after announcing his intention to quintuple his $20 million business in three years, he decided to settle for merely tripling it. Liz is preparing to spend heavily on trade shows and salespeople as she takes Citibin national, even if it means sacrificing profitability in the short term. She's also starting to think seriously about selling the business, possibly in as little as two years. And Jaci explains why she secludes herself out of town for a week every November to think about the future of her agency. Along the way, the three owners also discuss what they're expecting from health insurance costs in 2027, the messy secrets they'd least like a potential buyer to discover, and what employees should do when they believe their manager is making bad decisions. Plus: Liz's bear-resistant trash enclosure survives another encounter with actual bears, and Jaci reveals that she once had to undergo leadership training because she was making her direct reports cry. The episode is brought to you by Grasshopper Bank. Show Notes: Here’s a video of the bears attacking Liz Picarazzi’s Grizzbins. Get a free trial of the 21 Hats Morning Report.

  4. Oct 30

    Dashboard: Did She Sell the Business to Her Employees? Or Did She Give It to Them?

    After spending 30 years building Ocaquatics into a $10 million swim-school business with five locations and 150 employees, Miren Oca knew she needed a succession plan. She also knew what she didn't want: She had no interest in selling to private equity, and her son had made it clear he didn't want to take over the business. So Miren started exploring employee ownership. She considered worker cooperatives and even spent $50,000 pursuing an employee stock ownership plan before deciding that wasn't quite right, either.Ultimately, she chose a less familiar option: an employee ownership trust, or EOT. It allowed her to preserve the culture she'd built, share the company's future profits with her employees, and collect an eight-figure purchase price over 12 years. But there's an intriguing twist: Miren financed the entire transaction herself, which means she's being paid with cash flow from a business she previously owned outright. So she’s getting paid with money that would have been hers anyway. This week, Miren explains how she arrived at her decision, how the deal works, and why she believes it was the right choice for her, her employees, and the business. The episode is brought to you by Grasshopper Bank. Correction: In our conversation, I managed to confuse Miren with one of my questions, which led her to understate what she believed selling her business to an ESOP would have cost. Here are the right numbers: She says the estimated transaction cost for an ESOP was close to $500,000 — or roughly five times the $100,000 that her EOT transaction actually cost.

  5. Oct 27

    He Bought the Business. Now What?

    Last year, Jason Bridwell concluded a five-year search for a business to buy by snatching a 130-year-old custom woodworking company in St. Louis from what he calls the “jaws of liquidation.” The previous owners of Gravois Planing Mill had stopped accepting new orders, were allowing key employees to leave without replacing them, and had picked a date to close the doors for good. But Jason liked what he saw enough to make an offer—and then insisted that the owners hire him to start turning the business around even before the deal closed. This week, Jason compares notes with Paul Downs, who runs a similar woodworking business but is approaching the other side of the ownership equation: He's thinking about selling. Jason explains why he bought Gravois, why he now thinks he overpaid, what surprised him about the business—including an accounting system built around a handwritten ledger—and why he had to inject more of his own cash this year to keep it going. Along the way, the two owners discuss what makes a business worth buying, the value of open-book management, and the relative advantages of their very different business models. Paul, it turns out, wouldn't mind finding a buyer a lot like Jason. The episode is brought to you by Grasshopper Bank. Show Notes: This is the episode in which Ted Wolf says Paul Downs is devaluing his business by not implementing AI. Get a free trial of the 21 Hats Morning Report.

  6. Oct 23

    Dashboard: Could Your Business Run Without You?

    This week, we welcome Tanya Ferguson, founder of ClearBrook AI Solutions, who helps small-business owners identify and fix operational problems they may not even realize they have. Tanya works primarily with businesses that have fewer than 20 employees and less than $5 million in revenue. Many of their owners have spent years figuring out how to make their businesses work, but they're so caught up in the day-to-day that they haven't had time to figure out how to make them work better. And when they finally delegate responsibilities to employees, they may just be shifting the burden to someone else.Tanya's approach starts not with technology but with questions. She talks to owners and employees to find out how work really gets done, where time and money are being wasted, and which problems can be solved through better processes, automation, or AI. As she puts it, applying AI to a messy process just gives you a faster mess.Perhaps most interestingly, Tanya has developed a specialty in helping owners whose businesses are so dependent on them that they can be difficult to sell. She explains how she identifies those dependencies, how she helps buyers and sellers address them, and why fixing those problems might even persuade an exhausted owner that it's worth hanging on to the business after all. This episode is brought to you by Grasshopper Bank.

  7. Oct 20

    We Want to 5X Our Business in Three Years

    This week, David C. Barnett, Jennifer Kerhin, and Rob Levin compare notes on three very different approaches to growth. Dave, convinced that people are craving more personal connection in an increasingly digital world, is experimenting with an in-person conference. He's hoping the event will at least break even and, more importantly, help him attract consulting clients. Jennifer, meanwhile, is investing in leadership training to increase her company's capacity, but she's also wary of growing too quickly. A few years ago, her company grew 145 percent in a single year. “That almost killed all of us,” she says. And Rob has hired a consultant to develop a marketing strategy that he hopes will help him quintuple his business in just three years. “The market is ready for what we do,” he says. Along the way, the owners also discuss why charging more can make an event more attractive, what makes a business partnership work, why Jennifer is still reluctant to launch her next big idea, and where they turn for support when facing high-stakes decisions. “Well, I make my decisions with ChatGPT now,” says Dave. “Does that count?” The episode is brought to you by Grasshopper Bank. Show Notes: Here's more information about Dave's conference, SmallBizRIOT. Get a free trial of the 21 Hats Morning Report.

  8. Oct 16

    Dashboard: AI Is Moving Fast. Why Aren’t Businesses?

    I don't know any traditional business owner who has devoted more time and energy to figuring out what AI can do for small businesses than Alan Pentz. He's built his own AI agents, experimented with the latest models, and even started a business to help other owners put the technology to work. But here's the thing: Even Alan is struggling to keep up with how quickly AI is evolving. And when I ask him what other business owners should be doing, he doesn't have a great answer.The problem, as Alan sees it, is that most owners don't have the time—or the inclination—to learn how to build sophisticated AI tools themselves. And there aren't many qualified firms available to build those tools for them. For a while, Alan thought he could help fill that gap by consulting with individual owners. But he soon realized that developing custom solutions for every business wasn't a model he could scale. Now he's pursuing a different strategy with his latest venture, Rustproof.aI. But what if the real solution is already taking shape?In this episode, Alan and I discuss the emerging generation of personal AI agents, including Muse, that can take actions on our behalf. They're still limited, but could we be approaching a time when business owners can simply tell an AI agent what they want to accomplish and let the agent figure out how to make it happen? This episode is brought to you by Grasshopper Bank.

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5
out of 5
34 Ratings

About

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.

Information

  • Creator
    21 Hats
  • Years Active
    2020 - 2026
  • Episodes
    583
  • Rating
    Clean
  • Copyright
    © Copyright 21 Hats
  • Show Website
    21 Hats Podcast

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