21 Hats Podcast

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 devel...

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 ho...

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...

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...

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 bu...

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...

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 peop...

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...

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...

Small business owners have plenty to worry about these days. According to John Arensmeyer, founder and CEO of Small Business Majority, his organization's surveys show optimism is slipping as owners grapple with soaring health insurance premiums, rising energy costs, and the higher price of imported goods. And yet, the wave of entrepreneurship that began during the pandemic hasn't faded. In fact, it's still growing. So what's going on? Why are so many people choosing this moment to start businesses? What do they think they're seeing? And perhaps the more important question: What can we do to improve their odds of...

If you’ve owned a business for any length of time, you’ve probably told yourself some version of this: I'll deal with succession as soon as I solve whatever crisis my business is confronting right now. The problem, of course, is that there's always another crisis to solve or opportunity to pursue, and time has a way of passing.

Jay Goltz has spent decades building a collection of successful businesses in Chicago. He knows he needs a succession plan. He knows that if something happened to him tomorrow, there’d be chaos. And he'd very much like to lea...

There have been a lot of stories lately about companies getting hit with surprisingly large AI bills. They start using platforms like ChatGPT or Claude, usage grows faster than expected, and suddenly they're spending far more than they ever imagined. Should small businesses be worried? I invited AI consultant and longtime business owner Alan Pentz back on the podcast to find out. His answer may surprise you: for most small businesses, he says, runaway AI costs aren't the problem. If anything, he thinks they're spending too little.That led us into a wide-ranging conversation about why Alan has changed his...

Most business owners hope to reach the day when someone offers to buy their business. If that day comes, the payoff isn't just financial. It's validation for years of risk-taking, sleepless nights, personal guarantees, and sacrifices that most employees never see. But that success can raise an uncomfortable question: What exactly do owners owe the people who helped them get there? Should employees share in the proceeds when a business is sold? Does an owner have an obligation to find a buyer who will protect the culture and the jobs that have been built over the years? Or is the...

Business owners spend a lot of time preparing for things that could threaten their companies. They buy insurance, build cash reserves, create succession plans, and they worry about recessions, lawsuits, and key employees leaving. But there's one potentially devastating risk that many owners would rather not think about: What happens if the owner's marriage falls apart? This week, David Barnett explains how careful planning—including a prenuptial agreement—helped him avoid the worst-case scenarios when he got divorced. Jaci Russo offers almost the opposite perspective. She says building a business with her husband hasn't strained their marriage—in fact, it may ac...

Jared Bell never planned to own a fencing business. He took a summer job at Butte Fence in 1994, liked the work, and decided to skip college and stay. Thirteen years later, he bought out a partner and took over day-to-day operations—just in time for the Great Recession. The company survived that challenge and has gone on to thrive, but not by following a conventional growth playbook. Bell has expanded the business by repeatedly asking a simple question: Why buy from a supplier when we can do it better ourselves? Over the years, Butte Fence has developed new products, configured mo...

The new pay transparency laws were designed to help job applicants and narrow pay disparities. But they've also had an unintended consequence: Employees now have far more information about what other people are making—and that can raise some uncomfortable questions for business owners. How do you decide what a job is worth? How much should you pay compared to the market? How much should employees know about what their co-workers earn? This week, Jay Goltz, Jennifer Kerhin, and Ted Wolf compare notes on compensation. 

Jennifer explains how her philosophy has evolved from offering below-market pay and maximum fle...

A health scare in 2015 prompted Julia Beardwood to confront a question many business owners prefer to postpone: What happens when it's time to leave the business? Over the next several years, the founder of the New York City branding agency Beardwood explored a range of possibilities, including selling to an ESOP and pursuing a strategic acquisition. But when the time came, the solution turned out to be much closer to home. Years earlier, Julia had implemented a compensation strategy that gave key employees a meaningful stake in the company's success. What began as a way to motivate and retain talent...

The promise is seductive: Implement the right operating system and your frustrations disappear. Your employees become more accountable. Communication improves. Growth follows. Your business finally runs the way you always hoped it would. That's the promise behind EOS, the Entrepreneurial Operating System popularized by Gino Wickman's book Traction. Plenty of business owners swear by it. Plenty have spent tens of thousands of dollars hiring EOS implementers to help put it in place. But does it work?

This week, we’re republishing one of our favorite conversations, one in which Shawn Busse, Paul Downs, and Laura Zander compare notes on...

For years, Kim Robinson worked on the brand side, helping major companies connect with artists and creatives. Eventually, he decided he’d rather be working for the artists themselves. So he launched 3pts, a company that helps creatives handle the business side of their careers—everything from pricing and marketing to partnerships and strategy—so they can spend more time focused on the work they love.The first challenge, Kim says, is convincing artists that thinking about money and business doesn’t somehow compromise their creativity. The second is helping them understand that even the most gifted creatives still need a framew...

This week, Sarah Segal, Jaci Russo, and Lena McGuire tackle a question many service business owners face: Which is the bigger risk—an employee who feels overburdened or a client who feels neglected? The discussion begins with Sarah explaining why she's had to reestablish boundaries with some clients who were texting and calling her employees after hours and bypassing the systems her agency has put in place. Sarah wants her team to be able to disconnect at the end of the day, and she wants clients communicating with the entire team assigned to their account—not developing overly close relationships with...

Sean Joy is head of M&A at Chenmark, a Portland, Maine-based holding company that acquires a handful of small businesses each year. At first glance, Chenmark may sound like a traditional private equity firm, but it isn't. The company is family- and employee-owned, and when it buys a business, the goal isn't to improve it and sell it a few years later. The goal is to own it indefinitely.In our conversation, Sean explains what Chenmark looks for in an acquisition, how it finds businesses to buy, what it's willing to pay, and how it approaches management after a...

This week, we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom conference tables, says his business depends on something AI still lacks: real world experience. While AI can generate impressive images and concepts, he argues that it has no understanding of manufacturing constraints, material properties, production processes, or the capabilities of the people and machines that have to bring an idea to life. “An image of a thing that looks cool is not a design,” Paul says. “A design is a set of...

When Bryan Clayton graduated from college, he discovered he had two options: take an entry-level job and a pay cut—or go back to mowing lawns, which was already making him more money. He chose the lawns. Over time, he built a commercial landscaping business that grew to $10 million in annual revenue before eventually selling it. But even while running that business, Clayton had been thinking about another problem: why was it still so hard for homeowners to hire a reliable lawn service?Despite having no background in technology, Clayton bootstrapped a platform called GreenPal, which connects homeowners with lawn-care sp...

Twenty years ago, Bo Burlingham gave a name to a feeling a lot of business owners had struggled to articulate. In his book Small Giants, Bo profiled companies that had chosen not to chase growth at all costs. Most were bootstrapped, owner-operated businesses that cared less about getting big than about building something enduring, meaningful, and excellent. They weren’t anti-growth. They just wanted growth to be intentional. And for many owners who read the book, the reaction was immediate: “I thought I was the only one who felt this way.” Out of that recognition grew a community—and eventually an organ...

When Eugene Khayman first got involved with Million Dollar Sellers, it was essentially a support group for entrepreneurs building businesses on Amazon. Back then, the opportunity seemed almost limitless. Today, ecommerce feels a lot more complicated. Competition is tougher. Customer acquisition is more expensive. And sellers have many options beyond Amazon. At the same time, Khayman believes Amazon itself has changed—and not for the better. In a recent post on X, he argued that Amazon’s growing fees are “destroying the marketplace it created.” He’s now leading a campaign called Save Our Sellers, aimed at pushing back on policies t...

Michelle Wyatt has replayed the events in her mind countless times, looking for warning signs she might have missed. But even now, she can’t find any. Both employees had passed background checks and drug tests. Both were considered trusted, valued members of the team. And yet, within a span of months, two violent incidents involving employees left Michelle and her company reeling. In this week’s conversation, Michelle joins Jay Goltz, who has dealt with employee violence in his own business, and special guest Sandy Kapell, who’s made a career leading human resources, to wrestle with a question that h...

Hannah Sandmeyer spent years acquiring ecommerce businesses for an Amazon aggregator, giving her a front-row seat to how deals get done—and what often gets lost in the process. Too many owners, she came to believe, are forced to choose between shutting down their businesses or selling to buyers whose priorities may have little to do with preserving the company, the culture, or the people who built it. So she decided to build an alternative. Hannah is now founder and CEO of Steward Market, which she describes as “the first marketplace for ethical exits.”In this week’s Dashboard, she explains...

When Kate Morgan started thinking seriously about selling her business, she assumed the big payoff would come at closing. But as she tells David C. Barnett and Paul Downs this week, she’s come to understand that the smarter move might be not selling—at least not yet. Why? Because if the business keeps performing and she can gradually remove herself from the day-to-day operations, she may ultimately make more money by continuing to own it. That’s partly because, as David explains, small businesses often sell for lower multiples than owners expect. Which means the real value may not be in...

Most business owners know they need marketing. What many don’t know is what they should be paying for it—or what they should expect in return. So when an SEO agency proposes a $3,500-a-month plan, how do you assess whether it’s a smart investment or an expensive gamble? Do you know how many new customers it would take to make that spend worthwhile? Do you even have the data to answer that question? This week, Shawn Busse says too many owners are making those decisions in the dark. He offers a practical framework to help you do the math t...

Every business owner looks forward to that big break—the moment that you land a big client or a major retailer, or do something that puts you on a national stage. But those opportunities don’t just reward you. They can also expose you—especially if you have to take on debt or ramp up production or do things you haven’t done before. Four years ago, when Liz Picarazzi won a high-profile installation for her trash enclosures in Times Square, it was exactly that kind of opportunity. Her enclosures were put to the test in as public and as challeng...

For years, the Wine School of Philadelphia and PhillyWine LLC coexisted in the genteel world of wine education. Then a trademark dispute turned that quiet coexistence into a legal battle—complete with accusations, lawsuits, and mounting costs.This week, Keith Wallace, founder of the Wine School of Philadelphia, joins me to talk about what happens when a business owner who’s tried to avoid litigation at all costs suddenly finds himself in the thick of it. He shares what the fight has actually required—financially, emotionally, and strategically—and what he wishes he had done differently before things escalated. Because one of t...

For Lena McGuire, scope creep really can show up around every corner. She’s in the home remodeling business. But for most owners, including Jaci Russo and Ted Wolf, projects that expand out of control can be less visible but just as hard to contain. It’s baked into the job, because every assignment comes with a built-in tradeoff: Protect your margins or protect the relationship. And especially in the early days of a business, when reputation feels like everything, that’s not much of a choice. “I was afraid to have tough conversations with people,” Ted says. “I just wanted every...

Despite what we’ve been reading about tariffs and immigration and inflation and health insurance, the macro economy has actually held up better than many economists expected over the past year. Unemployment is low, corporate profits are high, and the stock markets have been setting records. So, this week, I put the question to John Arensmeyer, CEO and founder of Small Business Majority: Are things really that tough for small businesses? Well, yes, says John. It’s not necessarily any one issue, he says. It’s the constant drip, drip, drip of many issues. In this week’s conversation, we tackle s...

Early on, William Vanderbloemen’s search firm was exactly the kind of business HubSpot, the marketing platform, was built to help. William had a highly specialized audience, his team produced content that his audience needed, and HubSpot helped make sure the right people found it. Back then, he tells Kate Morgan and Jaci Russo, HubSpot’s promise was that it could help a David compete with a Goliath, and that’s what it did for Vanderbloemen Search.

But that was almost 20 years ago, long before AI began reshaping how people discover information. Now, William contends, the rules are changi...

Hiring a full-time marketing team isn’t realistic for a lot of small businesses—but doing nothing may not be an option either. This week, Johnathan Grzybowski explains how Penji, the platform he co-founded, offers a different path: subscription-based access to vetted creatives matched to your specific needs.We talk about how that model actually works in practice, where it fits (and doesn’t) for small businesses, and how Penji manages the tension between competing with—and supporting—traditional agencies. Plus: we talk about what happens to a business like Penji as AI reshapes creative work and why Johnathan believes there’s ul...

Sandy Kapell knows HR—just not the version most business owners live with. After years leading human resources for corporations, Sandy launched her own business, Trakehner Leadership, to bring that expertise to companies that need help. And she’s quickly found a big opportunity: Most small businesses don’t have HR departments, but they still have all the same HR challenges.

The catch? Sandy has also realized that knowing HR isn’t the same as knowing how owners think about HR. Or how they talk about it. Or what they’re actually willing to pay for it. So for our la...

In her thirties, Lisa Woodruff hit a breaking point—overwhelmed, overweight, and depressed, as she puts it. So she made a radical decision: she quit her job as a school teacher and set out to get her own life in order. What started as a personal reset became a business—Organize 365—built around a simple but powerful idea: running a household isn’t all that different from running a company.In her new book, Escaping Quicksand, Lisa argues that households, like businesses, need systems, delegation, and intentional leadership. But she also makes a point that may resonate with a lot of liste...

Pricing a service business sounds straightforward—until you actually have to do it. How much should you charge? What’s reasonable? And what happens when “reasonable” isn’t enough to keep the business healthy? This week, Sarah Segal walks David C. Barnett and Liz Picarazzi through how she thinks about pricing her PR services—why she aims for consistency across clients and why she resists charging based on what the market will bear but insists on building in enough margin to stay profitable. It’s a balancing act between values and reality, and not always a comfortable one.

The conversati...

Shawn Busse has never been an AI evangelist. If anything, he’s been wary of the hype. But lately, his thinking has started to shift. While it’s still early, Shawn sees AI pushing marketing away from the soul-deadening world of SEO hacks and keyword stuffing—and toward something far more human: real storytelling and authentic brand building. In this week’s Dashboard, he explains what he’s seeing in his own business and with clients, and what it may mean for owners trying to figure out where to focus next.

It’s easy to condemn the horror stories coming out of Noma, the celebrated restaurant in Copenhagen. But this week, Jay Goltz, Jennifer Kerhin, and Ted Wolf confront a harder question: How far are the rest of us—business owners in every industry—from crossing the line? Because it’s not just restaurants. Most owners don’t set out to be abusive. They set out to build something great. And somewhere along the way, high standards can start to blur into something else. ‘I was out of control when I was in my 20s,’ Jay admits.

So, what changed? And w...