21 Hats Podcast

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.

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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.

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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.

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.

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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.

This week, Jay Goltz, Lena McGuire, and Jaci Russo tackle three challenges that business owners face, starting with a question that can be especially painful: How do you know when it’s time to give up? The question is prompted by an article written by the founder of an online pillowcase business who has concluded that Big Tech, soaring advertising costs, and changes to privacy rules have made it all but impossible to build a profitable brand online. Jay, Lena, and Jaci agree that the obstacles are real, but they’re not convinced that they fully explain the entrepreneur’s failure to get traction. Nor are they sure she should throw in the towel. In fact, they think she may have a promising product and offer some suggestions, but, says Jay, “It doesn't sound like she's got the big tenacity gene that is necessary to be in business.”

Next we turn to a Boston-area ice cream shop that got fed up with customers abusing its mostly teenage employees and posted a blistering Facebook message telling customers, in all caps, “STOP YELLING AT MY [FREAKIN’] EMPLOYEES”—except it didn’t say freakin’. The post went viral, winning more than 230,000 likes and widespread praise. But was it smart business? Jay, Lena, and Jaci are all in favor of standing up for employees, but they have serious doubts about this particular approach. Plus: Are family and medical leave programs a burden on small businesses—or a benefit that helps them compete for employees? And if our three owners could permanently take off one of the 21 hats business owners have to wear, which hat would it be? The episode is brought to you by Grasshopper Bank.

Show notes:

Here’s more information about Jaci’s Women’s Summit at Sea.

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This week, we talk to Leisa Peterson, who has spent much of her career thinking about money, risk, and the ways our emotions can interfere with financial decisions. So when Peterson and her family decided to launch The Gear Project, a peer-to-peer marketplace for used outdoor equipment, you might have expected her to proceed with unusual discipline and caution. And she did—right up to the point where the numbers started telling her that maybe they shouldn’t launch at all.As Peterson built out her financial projections, she kept discovering costs she hadn’t anticipated. The margins got thinner. The transaction volume required to make the business work got higher. She was ready to walk away. Her husband, daughter, and son-in-law wanted to keep going. So they did. Now, just weeks after launching, Peterson is deep in the part of entrepreneurship no spreadsheet can fully anticipate: fixing shipping problems, refunding incorrectly collected sales taxes, changing developers, manually approving thousands of listings, and discovering which of the warnings she heard before launch were right—and which weren’t.Along the way, she’s also confronting something more personal: whether a lifetime spent protecting herself from financial risk may have kept her from taking some risks worth taking. This episode is brought to you by Grasshopper Bank.

This week, we welcome a new regular to the podcast team, Rob Levin, co-founder of WorkBetterNow. I first met Rob more than 20 years ago, when we were both experiencing the decline of print media. I was an editor at Inc. magazine, and Rob had started a regional publication for business owners called The New York Enterprise Report. “Starting a print publication in 2003 was not one of the smartest things I've done,” Rob says. But he learned from that experience. In 2018, Rob and a partner started WorkBetterNow, which helps American businesses hire Latin American talent. The business took off during the pandemic and has continued to grow rapidly. But in recent years, Rob began to see another disruption looming. If artificial intelligence can increasingly perform the kinds of tasks his company supplies people to do, what happens to WorkBetterNow?

Rob tells Sarah Segal and Jaci Russo how seriously he took that question, what he decided his company needed to become, and how he’s trying to position WorkBetterNow for whatever comes next. We also talk about why referrals are no longer enough to sustain the company’s growth, what went wrong when Rob tried to build an outside sales force, and what he’s learned about managing remote workers. Plus, in another Beyond Small segment brought to you by Grasshopper Bank, Sarah, Jaci, and Rob compare how they manage the cash they keep on hand—and Jaci explains why she’s sleeping better since adopting Profit First earlier this year.

Rob Levin’s book is called The New Talent Playbook.

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Most business owners know the usual ways to finance a startup or acquisition: savings, investors, bank loans, SBA loans. But there’s another option that many owners have never considered—even though Jeremy Ames says his company, Guidant Financial, has helped arrange more than 35,000 of these transactions. It’s called ROBS financing—Rollovers for Business Startups—and it allows entrepreneurs to use money they’ve accumulated in retirement accounts to start or buy a business without taking a taxable distribution and, perhaps most notably, without taking out a loan. There’s no debt and no monthly loan payment. Instead, the owner’s retirement plan buys stock in the business.In this 21 Hats Dashboard, Ames explains how the structure works, why some owners use it to avoid debt while others combine it with SBA financing to buy a larger business, and what it costs to set up and maintain. He also addresses the tradeoffs: The money is no longer invested in stocks or mutual funds; it’s invested in your company, which means you’re betting some of your retirement savings on your ability to build a successful business.We discuss the questions owners should ask before making that bet, including how ROBS compares with conventional financing, what happens if the business fails, why the IRS has scrutinized these transactions, and why Ames believes anyone considering one should consult an independent adviser. The episode is brought to you by Grasshopper Bank.