21 Hats Podcast

Hosted by 21 Hats

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563

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Sep 2026

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About the show

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.

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September 11, 202638 min

Dashboard: He Sold the Business. The Regrets Came Later

Kevin Donnelly was 44 when an unsolicited offer set in motion the sale of the telecommunications company he had spent nearly 20 years building. The business had grown to more than 600 people in 38 cities and about $50 million in revenue, and Kevin says the deal itself worked out well for him financially. But that doesn’t mean he looks back on the experience without regret.What bothers him most is what happened to the people who helped him build the company. After the sale, employees started getting let go, and Kevin came to believe he should have done more—through bonuses, transition planning, or simply by thinking more carefully beforehand about his obligations to the people who had helped create the value he was selling. As he puts it, the way you treat those people can “come back to haunt you.”That experience, along with a brief post-sale detour into the restaurant business, eventually led Kevin to become an exit-planning advisor and to launch Inside Exits . His focus now is on owners who may not have an easy path to a conventional sale—often because of customer concentration, owner dependence, limited scale, or other issues that make a business less attractive to strategic buyers or private equity.His answer is not that every owner should pursue an ESOP or any other single structure. In fact, Kevin is explicitly agnostic. He talks about ESOPs, employee ownership trusts, worker co-ops, management buyouts, sales to existing employee-owned companies, and other creative arrangements. His goal is to help owners find a path that works financially, gives the business a chance to continue, takes care of the people who helped build it—and, ideally, leaves the owner with fewer reasons to look back with regret. The episode is brought to you by Grasshopper Bank .

September 8, 2026Episode 30953 min

She Thought She Was Building a Prospecting Tool for Herself

This week, Jaci Russo, Liz Picarazzi, and David C. Barnett talk about something entrepreneurs are always being told they have to do: innovate. But how do you know which ideas are worth pursuing, how much time and money to put into them, and when an experiment starts to become something much bigger? Jaci Russo may be finding out. What started as a prospecting system she built for herself—with AI, verified data, and a simple CRM—has turned into ProspectDaily, a subscription product that attracted more than 100 customers before she even announced it. That has Jaci thinking the tool could do more than generate a little extra revenue. As AI makes it easier for clients to do more of their own marketing, she sees ProspectDaily deepening client relationships and ultimately changing the nature of her business. So far, she says, the hard costs of creating the tool amount to $185. (Try ProspectDaily for free.) Liz, meanwhile, is spending $10,000 this year testing whether old New York City trash cans and other recycled plastics can be turned into a new cladding material for Citibin. And she’s itching to spend another $30,000 on the equipment to manufacture the material once she determines whether customers actually want it. Both Liz and Jaci kept their projects quiet early on. As Liz explains, “I have so many ideas all the time. I didn't want there to be eye-rolling, ‘Oh, here's another of her things.’" Plus: In our latest Beyond Small segment, brought to you by Grasshopper Bank, the owners compare how closely they watch their numbers, which metrics matter most, and whether spending time on financials gets in the way of doing the work they really want to do—like coming up with new products.

September 4, 202631 min

Dashboard: The Competitive Advantage AI Can’t Copy

When Nathan Miller started Rentec Direct almost 20 years ago, he wasn’t trying to disrupt an industry. He was a small landlord who couldn’t find affordable software that did what he needed, so he built his own. Other landlords started using it, then paying for it, and over time Rentec carved out a meaningful place in what became an increasingly crowded and well-funded market.Nathan says the company has managed to keep growing not by trying to match its venture-backed competitors dollar for dollar, but by sticking to a fairly simple formula: understand the customer, keep prices reasonable, provide unusually knowledgeable support, and build the kind of reputation that generates referrals. Today, Rentec has 16,000 property-management customers, 20 employees, and about $16 million in annual revenue.That formula is being tested again by artificial intelligence. AI has already wiped out much of the organic search traffic that once brought Rentec new customers, and Nathan acknowledges that it has also made it possible for almost anyone to build competing software. But he doesn’t sound especially worried. As he sees it, writing the code is only one small part of building a business. The harder things to reproduce are trust, reputation, industry knowledge, and customer service—which happen to be the things Rentec has been investing in all along.This week, Nathan explains how Rentec bootstrapped its way into a crowded market, why he continues to turn down investors, how AI is changing both his product development and his marketing, and what nearly 20 years of working with landlords has taught him about managing rental properties. The episode is brought to you by Grasshopper Bank .

September 1, 2026Episode 30852 min

We’re Growing. Now I Want to Make Money

This week, Sarah Segal tells David C. Barnett and Jay Goltz that she has decided it’s time to pay more attention to something that can occasionally get lost amid the other demands of running a business: making money. Sarah’s agency is having a very good year, with revenue growing 40 to 50 percent. But she’s realized that growth alone isn’t enough. She wants to know exactly what it costs to hire each employee, what it costs to service each client, whether her fees are covering those costs—and what has to change if she’s going to hit a 20 percent profit margin. She’s also confronting something a lot of owners struggle with: how much to pay herself. For years, Sarah says, she’s been inclined to put the money back into the business rather than pay herself a market rate salary. Now she’s trying to do both—raise her own compensation while making the business more profitable. Along the way, Sarah, Dave, and Jay weigh in on how owners can fool themselves about profitability, why growing businesses eventually require real budgets, and what owners should actually expect from their banks. Is a bank merely a safe place to park your cash, or can you expect it to help you finance and build your business? Plus: When should a new business start paying its owner a salary? Dave argues that until a business can pay the owner for the work he or she is doing, it’s more of a hobby than a business. He also explains how entrepreneurs can get trapped in money-losing businesses—not necessarily because they still believe in the business, but because loans, leases, and personal guarantees can make shutting down even more expensive than continuing to operate. The episode is brought to you by Grasshopper Bank .

August 28, 202639 min

Dashboard: Stop Asking How to Use AI

Business owners are being told constantly that they need to figure out how to use AI. Deb Weidenhamer thinks that may be the wrong place to start. Instead, she says, owners should look for the places where their businesses are already struggling: Where are you wasting time? Where are you losing money? Where are customers getting frustrated? Then ask whether AI can help.In this week’s Dashboard, Deb, author of AI for Real Companies : A Practical Guide to Smarter Systems and Stronger Profits, walks us through several examples of businesses that have done exactly that. A pizza shop uses AI to answer calls it had been missing during busy periods. A machine shop uses it to take on jobs that previously weren’t worth the time it took to quote them. And a real-estate team uses it to respond to leads that arrive while everyone is asleep. We also talk about the harder questions: whether AI really will eliminate jobs, why automating a bad process can make things worse, and why Deb believes the owner—not the IT person or some newly appointed “AI expert”—needs to take responsibility for deciding what gets automated and why. The encouraging part is that none of this necessarily requires becoming an AI expert. It requires understanding your business well enough to know what needs fixing. The episode is brought to you by Grasshopper Bank .

August 25, 202650 min

Best of: Selling My Business Nearly Broke Me

This week, we revisit a conversation with Laura Zander that we first published last year, shortly after she and her husband Doug sold Jimmy Beans Wool, the business they had spent more than two decades building. Laura had been preparing to sell for years. She had kept the company’s books clean, built systems that could survive without her, and cultivated relationships with potential buyers. In other words, she had done many of the things owners are told they should do to prepare for an eventual exit. And still, when the right buyer finally came along, Laura says the process nearly broke her. There were 155 due diligence requests, endless rounds of legal negotiations, mountains of paperwork, and months when Laura and Doug were so consumed by the transaction that the business itself suffered. Meanwhile, life kept happening: a major website migration, tariffs, industry turmoil, family issues, and the constant fear that some unexpected development would cause the buyer to walk away. Even after the papers were signed, the work—and the stress—continued. Laura did ultimately get a deal she was happy with. But the more useful lesson may be what it took just to get there.

August 21, 202637 min

Dashboard: Is Staying Small Selfish?

I met Lamar Tyler, founder of Traffic Sales & Profit , a couple of years ago at a Zone of Genius conference, where I interviewed him on the main stage. It quickly became clear that Lamar, who helps business owners grow, had a lot of smart, practical advice to offer, and I’ve been following him ever since. He recently posted something on LinkedIn that stopped me: “Staying small as a Black business owner is selfish.” Lamar, obviously, was speaking primarily to Black entrepreneurs, but his challenge applies more broadly. His argument is that owners who have the ability to build larger companies—and create more jobs, wealth, and opportunity—should not use “protecting their peace” or “staying lean” as an excuse to remain comfortable.I understand and appreciate what Lamar is trying to accomplish. But “selfish” is a heavy word. Isn’t an owner entitled to say, “I built this business to create a good life for myself and my family. Isn’t that enough?” Entrepreneurship is already hard. Most businesses fail. How much more risk should we encourage owners to take—and how much responsibility should they be expected to carry? That’s where Lamar and I begin this week’s Dashboard conversation. The episode is brought to you by Grasshopper Bank .

August 18, 2026Episode 30743 min

With My New Rent, I Will Clear Nothing

This week, we start with a business owner who’s just learned his rent is jumping 40 percent and who sees three options: accept the new rent and essentially work for free, move and start over, or shut down and get a job. But when Paul Downs, Jay Goltz, and Ted Wolf do the math, they see another option—one the owner doesn’t seem to have considered. From there, the conversation turns to the choices owners make when the answer isn’t obvious. Paul, as it happens, is wrestling with two of those himself. Before the year began, he developed a plan to start selling his custom conference tables in the Middle East. Then the missiles started flying. Does he still spend $30,000 to see whether the opportunity is real, or should he put that money to work closer to home? And then there’s a potentially lucrative R&D tax credit that Paul thinks could be “a gift from heaven.” He believes his company qualifies for the credit, but he also wonders whether claiming it could invite unwanted scrutiny from the IRS. Different decisions, different stakes, but the same question: As Paul puts it, “What is your appetite for risk?”

August 14, 202636 min

Dashboard: It’s Not That Earnouts Are Bad. It’s That Bad Earnouts Are Bad

Conventional wisdom about selling a business is pretty clear: If at all possible, get your money at closing. Don’t leave a big chunk of the purchase price dependent on the future performance of a business you no longer control. David C. Barnett, who helps people buy and sell businesses, has challenged that conventional wisdom, arguing that earnouts and other forms of deferred payment can sometimes help buyers and sellers get better deals done. Josh Patrick, who has owned and sold businesses himself and advised many other owners through transactions, is more skeptical. Which is why I was kind of hoping for a fight.Instead, Dave and Josh end up agreeing on quite a lot—including that once a seller decides to leave money in a deal, choosing the right buyer becomes every bit as important as negotiating the right price. Can the buyer actually run the business? What happens if things go wrong? What information should the seller continue to receive? And how can the deal be structured so that both sides have an incentive to make the transition work? So no, this isn’t quite the earnout cage match of my dreams. It’s actually far more insightful than that. The episode is brought to you by Grasshopper Bank .

August 11, 2026Episode 30643 min

My Succession Plan Just Moved to Montana

Jaci Russo has had quite a summer. First, her husband and business partner, Michael, underwent an unexpected quadruple bypass. Fortunately, Michael's recovering well, and their branding agency passed an important test: With both founders largely out of commission, the team kept the business running and the clients happy. But that wasn't the only surprise Jaci had to deal with. For the past several years, she and Michael thought they knew exactly how they would eventually leave the business. They had a succession plan. They had a timetable. And they had already begun putting the pieces in place. Now, they're back to figuring it out. This week, Jaci tells Jay Goltz what happened and how she's thinking about her options now. It's a reminder that succession planning isn't just about choosing among selling to family, employees, investors, or some other buyer. It's also about recognizing that circumstances change, people change, and even a plan that once seemed settled can suddenly become anything but. Plus: We check in with Jay to see whether he's received the hundreds of thousands of dollars he's expecting in tariff refunds. And with Wayfair reporting improved sales, I ask Jay whether that's a sign the furniture business is finally recovering—or whether Wayfair's gains might actually be bad news for independent home stores like his. This episode is brought to you by Grasshopper Bank .