21 Hats Podcast

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.

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.

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.

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.

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.