21 Hats Podcast

Hosted by 21 Hats

Business Entrepreneurship Marketing NewsInterviews guests

Website RSS feed

Episodes

559

Latest episode

Aug 2026

Language

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.

Listen to episodes

60 recent

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 .

August 7, 202633 min

Dashboard: The Problem with Retainers (and Other Lessons for Solopreneurs)

If you've built a successful business, you've likely been told the path to more success is obvious: hire employees, land bigger clients, lock in recurring revenue with retainers. But what if those aren't signs of progress? What if they're traps?This week, I talk with Pia Silva, author of Scale Solo , who argues that many of the traditional rules of entrepreneurship simply don't apply to solopreneurs. She explains why hiring too soon can derail a business, why retainers often aren't nearly as profitable as they appear, and why she'd rather do 10 $3,000 projects than one $30,000 engagement. Along the way, Pia also tells us why she and her husband named their branding agency Worstofalldesign, why she isn't afraid to tell clients, "You don't get a say," and how she's learned to sell clients on paying higher prices. This episode is brought to you by Grasshopper Bank .

August 4, 2026Episode 30350 min

You’re Pre-Qualified for a 13% Loan! (That Really Costs 170%)

This week, we begin with the story of Paloma Corona, the owner of a thriving preschool in Los Angeles who needed money to expand to a second location. She thought she was borrowing at an annual percentage rate of 13 percent. In reality, the effective APR was 170 percent. She also thought she was taking out a loan. Instead, she was placed in a merchant cash advance—an increasingly common form of financing that can sidestep many of the laws governing traditional loans. The daily payments quickly began draining not only the profits from her business, but also her personal savings. Her business survived, but only because a nonprofit lender stepped in to refinance the debt. Paloma’s story is especially troubling because she wasn’t reckless, uninformed, or running a failing business. She was trying to build a good business. But she was up against a financing industry that has become remarkably skilled at making extraordinarily expensive money look fast, easy, and affordable. My guests today have all been fighting this problem from different vantage points. Jay Goltz owns a picture framing business and a home furnishings store in Chicago. Ami Kassar helps business owners secure SBA and other responsible financing. And Louis Caditz-Peck, who helped build LendingClub’s small business operation, is now executive director of the Responsible Business Lending Coalition . In our conversation, we talk about why good businesses get steered into bad financing, how brokers can earn more by recommending the most expensive products, why offers embedded in platforms such as QuickBooks, PayPal, and DoorDash can be especially tempting, and what business owners should do before accepting fast money. We also ask what seems like a remarkably simple question: What could possibly be the argument against requiring every small business financing company to disclose, clearly and prominently, the true annual percentage rate it is charging? This episode is brought to you by Grasshopper Bank .

July 31, 202639 min

Dashboard: The ESOP Risk Nobody Talks About

ESOPs are often presented as one of the best ways for a business owner to exit. You preserve your company's independence, reward the employees who helped build it, and create a retirement benefit that can be life-changing for the people who stay with the business. What gets less attention is that ESOPs are still businesses. They can lose customers. They can hit hard times. And because employees' retirement savings are often tied to the company, the stakes can be even higher than they are at a conventionally owned business.This week, Roland Burdett tells the story of Miklos Systems, a Virginia defense contractor that became an ESOP in 2006 and spent nearly two decades building an ownership culture in which employees truly thought and acted like owners. Then came the pandemic, the Great Resignation, and, most recently, the uncertainty created by DOGE and deep cuts to federal contracting. Suddenly, Roland found himself worrying not only about his employees' jobs, but about their retirement savings as well.Rather than continue rolling the dice, Miklos made the difficult decision to sell itself to a larger defense contractor. Roland takes us inside that process—from explaining the decision to employee-owners, to working with an outside trustee who ultimately had the authority to approve the deal, to the surprising complexity of unwinding an ESOP after 20 years. Along the way, he offers a refreshingly candid look at both the strengths and the limitations of employee ownership, and why, in the end, protecting the people who had helped build the company meant giving up the independence they had worked so hard to preserve. This episode is brought to you by Grasshopper Bank .

July 28, 2026Episode 30450 min

‘I Want My Employees Building My Business, Not Theirs’

Side hustles have gone mainstream. More employees than ever are starting businesses of their own—sometimes to earn extra income, sometimes as insurance against layoffs, and sometimes because they dream of becoming entrepreneurs themselves. But what does that mean for the businesses they already work for? If you invest months in training an employee, isn’t it fair to expect that person to devote their best energy to helping your company grow? That's not an immediate concern for Lena McGuire, who's still a solopreneur. But as she prepares to hire and train her first employees, she worries about investing in people who ultimately may see her business as a stepping stone. Sarah Segal isn’t as concerned, but she does want her employees to view their jobs as careers, not placeholders. And then there's Channon Kennedy. While working full time at Silicon Valley Bank, Channon invented a woodworking tool, got it manufactured, landed national distribution, and traveled the country to trade shows—all, she says, without letting her day job suffer. And that’s what she expects from her employees with side hustles. Meanwhile, both Lena and Sarah are wrestling with another challenge: finding the right home for their growing businesses. Lena needs a showroom but doesn't want to sink money into leased space—and she can't find a building to buy. "I'm missing out on growth," she says. "I feel like I'm stalled." Sarah has opened a second office in Silicon Valley, but she's wondering whether it's time to leave her quirky “starter” office in San Francisco for something that better reflects where her business is headed. Buying would be ideal, but that's easier said than done in San Francisco these days. Plus: Sarah recently did something she hadn't done in almost a decade as a business owner—she turned on an out-of-office message and actually unplugged for a vacation. Spoiler alert: there was only one real crisis.

July 24, 202636 min

Dashboard: Why Open Books and Employee Ownership Aren't Enough

One thing I've noticed over the years is that business owners love talking about employees who think like owners, who take initiative, solve problems, and don't wait to be told what to do. The harder question, of course, is: How do you actually build a company that encourages people to behave that way? My guest this week thinks most businesses actually encourage people to do the opposite.Dean Meyer is an executive coach who specializes in organizational transformation, and he believes that employee engagement has a lot less to do with perks, personalities, or motivational speeches than it does with the way a business is designed. His core idea is deceptively simple: Every manager should run a business within the business—with customers, responsibilities, and the freedom to figure out how to deliver results. It's a different way of thinking about organizational structure, and as you'll hear, it challenges some widely accepted ideas, including what employee ownership and open-book management can—and can't—accomplish on their own.Along the way, Dean explains why he says he can predict where conflict exists just by looking at an organization chart, why he believes founders become the biggest obstacle to growth once a company reaches a certain size, and how one entrepreneur used these ideas to build a company that became better at innovating, integrating acquisitions, and attracting talent. Whether you agree with Dean or not, I think you'll find that he offers a fresh perspective on a question every growing business eventually confronts: How do you build an organization that doesn't depend on the founder to make everything happen? This episode is brought to you by Grasshopper Bank .

July 21, 2026Episode 30359 min

Would You Rather Own a Business in the U.K. or the U.S.?

Nearly 10 years ago, Simon Bedding, who owns a manufacturing company in England, picked up a copy of Boss Life , Paul Downs' memoir about running (and almost losing) a manufacturing company in Pennsylvania. Simon liked the book enough to email Paul. Paul wrote back. And over the years, they've kind of stayed in touch. This year, as we mark the 250th anniversary of the United States spinning off from the United Kingdom, we thought it would be illuminating to get these two business owners together to compare notes. After all, their countries started with the same language and much of the same legal tradition, but two and a half centuries later, running a business on opposite sides of the Atlantic can feel very different. In this conversation, Paul and Simon compare taxes, regulation, hiring, health care, government support, and what it's like to build a manufacturing business in their respective countries. Along the way, there are plenty of moments when one of them can't quite believe how the other has to operate. Wait—you can't fire an employee without going before a tribunal? Wait—you have to spend a week every year figuring out health insurance? Wait—your employees don’t have employment contracts? And yet, for all of their differences, Paul and Simon also discover something else: Whether your factory is in Pennsylvania or southeast England, some challenges are universal. It's hard to find great people. It’s hard to fight city hall. In short, it's hard to build a successful business. And, as Paul puts it, "You're always going to learn something by talking to other business owners." This episode is brought to you by Grasshopper Bank .