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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October 2, 202639 min

Dashboard: Finance Your Business Without Taking on Debt or Investors

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 .

September 29, 2026Episode 31248 min

Maybe AI Won’t Destroy My Business

This week, Paul Downs, Jaci Russo, and Sarah Segal revisit a question that came up on the podcast more than a year ago: Is artificial intelligence going to doom professional service firms like Jaci’s branding agency and Sarah’s PR firm? So far, both Jaci and Sarah are feeling pretty good about their prospects. In fact, they’re seeing changes in the market that suggest AI may be helping rather than undermining their businesses. Paul, meanwhile, has encountered a different kind of AI mystery. For years, his custom conference table business has depended heavily on people finding him through Google. Recently, he discovered that his organic search traffic has fallen about 35 percent. That sounds alarming—except that his business is doing great. Paul says his tables are selling like “hotcakes,” and he’s backlogged into February. So what exactly is happening when traffic falls but sales keep growing? Plus: In our latest Beyond Small segment, sponsored by Grasshopper Bank , Paul, Jaci, and Sarah talk about the financial processes they still insist on doing manually—even when technology could probably do more of the work for them. In each case, part of the reason is that doing the work themselves gives them a view into their operations that they don’t want to lose. As Sarah puts it, while she already knows how to handle public relations, “I am learning how to be a business owner every day.” Show Notes: Here’s the episode where Alan Pentz predicted that professional service agencies are doomed . Get a free trial of the 21 Hats Morning Report . There are three seats left for the 21 Hats Succession Solutions Workshop .

September 25, 202630 min

Dashboard: Do You Care What Happens to Your Business After You Sell It?

This week, Lou Mosca raises a question that business owners may not spend enough time thinking about before they sell the business: Once you’ve gotten the price you want, how much do you care what happens to the business? Lou, who owns the consulting firm American Management Services, has spent decades working with owner-operated businesses. More recently, he’s also been trying to work with private equity firms whose portfolio companies need help improving their performance. And that has given him an increasingly close look at what can happen when an owner sells to private equity.As Lou sees it, private equity can absolutely be the right exit for some owners. But he also thinks owners need to understand that getting a great price doesn’t necessarily mean they’ll be happy with what comes next. Lou shares some cautionary stories and offers practical advice for owners considering a PE offer—especially those who do care about what happens to their employees, their culture, and the business they built. The episode is brought to you by Grasshopper Bank .

September 22, 2026Episode 31146 min

Can an Owner Really Know What’s Going On?

This week, Jay Goltz and William Vanderbloemen tackle a problem that business owners may associate with big companies: What happens when an employee becomes convinced that his or her manager is making bad decisions, but going through normal channels just isn’t working? Jay says he absolutely wants employees to speak up, even if that means going over a manager’s head. William agrees that there are times when an employee has to escalate a problem. But as the conversation unfolds, both acknowledge something that can be easy for an owner to underestimate: Speaking up can feel extraordinarily risky to employees. And how is that information going to surface then? And in our latest Beyond Small segment, Jay and William discuss what, if anything, another bank could offer that would persuade them to move their business—and why both have grown wary of what happens when smaller banks get swallowed by bigger banks. Plus: How should owners think about the forecast of a prominent economics group that a severe downturn is likely to hit in 2030? And William talks about how his wife’s cancer diagnosis has changed the way he thinks about time, work, and succession. As one of his older golf partners put it, life is like a roll of toilet paper: “It goes really fast at the end.” Show Notes: Read more about ITR Economics’ Great Depression forecast for 2030 . Get a free trial of the 21 Hats Morning Report . Learn more about the 21 Hats Succession Solutions Workshop .

September 18, 202633 min

Dashboard: Are You Still the Best Person to Run Your Business?

For a lot of business owners, there comes a point when the obvious choices seem to be: keep running the business or sell it. But Tighe Burke says there’s a third option that owners often overlook: keep the business, hire someone else to run it, and let that person take it places you may not be equipped—or inclined—to take it yourself. Burke, who runs the executive recruiting firm Srch, specializes in finding operators for founder-led businesses. He says one of the hardest things for entrepreneurs to accept is that someone else may actually be better at running their company than they are.In our conversation, he explains how owners can tell when it’s time to step aside, what it costs to hire a professional operator, why owners have to be prepared to give that operator real authority, and what tends to happen when they don’t. He also explains why, for an owner contemplating an exit, hiring the right CEO can sometimes be a better financial move than selling—allowing the owner to keep collecting profits, grow the company's value, and perhaps sell it later for considerably more. The episode is brought to you by Grasshopper Bank .

September 15, 2026Episode 31048 min

You Just Lowered the Value of Your Business

Earlier this year, Ted Wolf suggested that Paul Downs should take a serious look at how artificial intelligence might improve his custom woodworking business. Paul was skeptical—but he invited Ted and his team to come visit the shop and see for themselves. This week, Ted reports back. He came away impressed by the business Paul has built but also convinced that Paul has a problem: As Ted sees it, too much of what makes the company work still resides in Paul’s head. Ted believes AI could help capture some of that knowledge, improve everything from estimating to production, and, perhaps most important, prepare the company to run one day without Paul. Paul remains unconvinced. He agrees that AI will find its way into the business eventually, but he questions whether it can capture the judgment, experience, and nuance required to build one-of-a-kind products. His inclination is to let the next owners figure that out. “So Paul,” Ted responds, “if they’re going to have to deal with it, you just lowered the value of your company.” Which raises a question that goes well beyond AI: If you hope someday to sell or transfer your business, how much of what you know has to be captured before you leave? Plus: In our latest Beyond Small segment, sponsored by Grasshopper Bank , I ask Paul, Ted, and Lena McGuire what would happen if their businesses suddenly doubled. Would they be thrilled—or terrified? Could they handle the growth? And would they even want it? That leads to a discussion that comes up here fairly often: How big do you really want your business to be?

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 .