This week, we dig into employee ownership with two people who’ve lived it: Kris Maynard and Justin Jordan of Cathedral Holdings, a 100-percent employee-owned ESOP since 2011. Kris and Justin are enthusiastic proponents of ESOPs, but they’re also candid about what can go wrong. Yes, ESOPs come with big tax advantages. But the transaction can be complex. The debt can fundamentally change the risk profile of a business. And perhaps the most under-discussed challenge of all: not all employees embrace employee ownership. Some see it as little more than a glorified retirement plan. And here’s the thing: an ESOP can be a far riskier retirement plan than many understand. They differ from 401(k)s in that there's no regulation requiring an ESOP to sequester its employees’ retirement funds. If the company fails—and like all businesses, ESOPs do fail—those nest eggs can vanish. Kris and Justin explain how they’ve addressed these issues and what they might do differently if they were starting over. They also emphasize an important point: Not all ESOPs are created equal. “If you’ve seen one ESOP,” Justin likes to say, “you’ve seen one ESOP.”
This week, we welcome Ted Wolf, co-founder of Guidewise, as the newest regular member of the 21 Hats Podcast crew—and Ted arrives with a pretty good story. Back when he was building his IT staffing business with his brother, a senior employee walked out. But he didn’t walk out alone—he took key employees, key accounts, and 40 percent of the company’s revenue. At the time, Ted thought it was the worst day of his business life. Turns out, he says, it was his best. Because that disaster forced him to rethink everything—how decisions get made, how profits get shared, how responsibility gets distributed. And that shift led not only to healthy growth but eventually to the kind of exit business owners dream about. That experience continues to inform the work Ted does today, helping companies integrate AI into their operations. The hard part, he tells Jennifer Kerhin, isn’t the technology—it’s the people. It’s managing the change, the fear, the implications. The technology matters, too. Ted and Jennifer also discuss whether small businesses should try to retrofit AI into their current tech stacks—or whether the smarter move, painful as it may be, is to start fresh.
This week, Jay Goltz, Lena McGuire, and Liz Picarazzi discuss a common concern: When does it make sense to buy a building for your business? Under the right circumstances—say, with an SBA loan, a good location, and a little luck—the real estate could end up being worth more than the business itself. But what if the business is just getting started? Or what if the owner is nearing retirement age and may not be around to reap decades of appreciation? Is buying the business still a good idea? Meanwhile, Liz and Lena also compare notes on their ever-evolving tariff challenges. One thing Lena has observed is that some owners in her industry have just had it. They don’t want to deal with the uncertainty, and they’re just packing it in: “We're going to see who survives all this,” she says, “and I want to be a survivor.” Plus: Liz has her first “aha” moment with an AI tool her team built, one that’s already helping convert sales.
This week, David C. Barnett, Kate Morgan, and Sarah Segal tackle a challenge every owner who sells services eventually faces: Clients want to hire you, but you want them to understand they’ll mostly be working with your team. How do you make that clear without scaring them off? For some, it’s a delicate balancing act. For Kate, it’s simple: if a client insists on her personal time, she charges, in her words, “a boatload of cash.” Plus: we dive into another tricky owner decision: how to structure bonus plans that truly drive retention. David is weighing a deferred bonus approach, where payouts happen over several years. It’s a proven way to keep people around, but he wonders: Do you really want employees who’d otherwise leave to stay just for the money? Also, when valued employees get an offer, do you counter-offer? And if they leave, do you tell them they can always come back?
This week, David C. Barnett, Jay Goltz, and Kate Morgan wrestle with one of the trickiest challenges for business owners: how to give employees room to grow without losing sight of the company’s mission. David points out that every business is on its way to obsolescence unless it deliberately evolves—and one way to do that, he says, is by letting employees experiment and try new things. That approach, Jay says, is exactly what led to his building a furniture business. Plus: Kate and Jay agree that while many aspects of running a business can be stressful, nothing has been more stressful for them than the period when their businesses were growing the fastest. And the owners react to a Reddit post from someone who has found that hiring employees has created more problems than it has solved. “Is this just what having employees is like?” the owner writes. “Please tell me I'm not the only one losing my mind.”
This week, David C. Barnett and Jennifer Kerhin say they’re already making plans for next year: adjusting pricing, conducting employee reviews, and setting budgets. In the past, Jennifer has chosen to restrain growth to give her employees and her processes a chance to catch up. But this coming year? She says she’s ready to “unleash the hounds.” And for the first time, she’s planning to budget for profit first and then force her expenses to fit her margins. Unlike Jennifer, who conducts employee reviews throughout the year, David saves his evaluations for the end of the year. As he looks forward, he’s trying to figure out what the economy means for his business. He’s seeing more companies in distress, but also more opportunities to help people with severance packages who decide to buy businesses. Plus: David and Jennifer share how they’ve each been experimenting with ChatGPT of late.
This week, Mel Gravely brings closure to a story he’s been sharing in pieces over the past year. You may recall that he bought a facilities maintenance company a couple years ago that he was convinced he could scale—only to discover that it was hemorrhaging money. Mel dug in, diagnosed the problem, fixed it, bought out his partners, turned the company profitable—and then decided to shut it down. Why close a business that’s making money? Mel explains the surprising answer, along with three lessons he says he learned. He also joins Jay Goltz in a candid discussion of the painful flipside of hiring: When, and how, does it make sense to lay off employees? As Jay points out, it’s far easier to find advice about adding people than about letting them go, even though it’s a calculation many owners are facing today. Plus: A would-be entrepreneur preparing to launch a business with two friends admits he’s feeling scared. He wants to know whether that fear ever goes away. Mel and Jay think he’s asking the wrong question.
This week, we bring you another 21 Hats Brainstorm. Elan Daniel, who started a small-batch hummus business inspired by a memorable experience in Israel, is trying to figure out his best path to long-term viability. So far, he’s been selling at farmers markets and direct to consumers, making all of the hummus and all of the deliveries himself. Since February, his sales have been growing between 5 and 10 percent a week, but his growth is constrained by his refusal to use preservatives, which adds flavor but limits the product’s shelf life. So how should he proceed: Should he sell to speciality markets and restaurants? Should he try to sell to Whole Foods? Should he open his own hummus restaurant, or hum-oo-sia? Should he try to introduce his hummus to the uninitiated or should he focus on connoisseurs? To help Elan think through his options, we convened a panel of 21 Hats Brainstormers and recorded this podcast episode. It’s brought to you by New Bridge Studios, which helps companies, creators, and causes connect their story to the bottom line. And by the way, if you have a challenge you’d like to put before a panel of business owners in our next Brainstorm, shoot me an email: loren@21hats.com.
A few months ago, John Abrams—author of From Founder to Future—joined us to talk about succession strategies and the different ways business owners can share ownership with employees. For his own business, John chose one of the more radical options: he turned his construction firm into a worker cooperative. Perhaps surprisingly, the more he described the co-op model, the more intrigued Jay Goltz became—although, predictably, Jay did retain a degree of skepticism. So we asked John to come back on the podcast to help Jay dig a little deeper: Are co-ops really all about democracy? Does someone on the loading dock get the same vote as the CEO? How do profits get split in the co-op model? How do losses get absorbed? How are loans secured without burdening frontline workers with personal guarantees? And perhaps most important: What can go wrong? In the end, I think surprising even himself, Jay failed to identify any real dealbreakers.
This week, Jaci Russo and Sarah Segal wrestle with a question that haunts many entrepreneurs: How do you bring your kids into the business—whether for a summer or for good—without messing up the business (or the kids)? For years, Jaci and her husband Michael quietly hoped their son Jackson might one day take over their marketing agency. Their unusual strategy? Never mention it to him—at least not until he’d demonstrated interest and not until he’d proven himself somewhere else. The approach seems to have worked: Jackson has joined BrandRusso, and Jaci has told him he’ll take over in four years. Which prompted Sarah to ask Jaci an obvious question, “What happens if he takes over, and he does a bad job?” As it happens, Jaci and Michael have thought about that, too. Plus: Jaci and Sarah discuss the merits of the new tech trend, especially hot in San Francisco, where more and more people are wearing AI-powered devices that can stealthily transcribe every conversation they have.