21 Hats Podcast
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 a...
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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 bu...
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...
‘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 peop...
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...
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...
Dashboard: Why Do People Keep Starting Businesses?
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...
I’ll Deal with Succession Next Year
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.<br /><br />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...
Dashboard: You're Probably Not Spending Enough on AI
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...
What Do You Owe Your Employees?
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...
Would Your Business Survive a Divorce?
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...
