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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Nov 13, 2026 · 28:02
Last week's blue wave election gave Democrats control of both houses of Congress. But what will that mean for small business owners—and should they welcome the change or worry…
Nov 10, 2026 · 41:45
Channon Kennedy spent between $15,000 and $20,000 exhibiting her Morgan Square measuring tool at five trade shows in eight weeks. She sold out at three of them, had her best…
Nov 6, 2026 · 46:20
When Jessica Johnson-Cope took over her family's security business in 2008, she inherited a company with just 16 employees and no succession plan. Today, Johnson Security Bureau…
Nov 3, 2026 · 52:22
This week, Rob Levin, Liz Picarazzi, and Jaci Russo talk about what they're planning for 2027—and how much they're willing to invest to achieve their goals. Rob explains why,…
Oct 30, 2026 · 45:40
After spending 30 years building Ocaquatics into a $10 million swim-school business with five locations and 150 employees, Miren Oca knew she needed a succession plan. She also…
Oct 27, 2026 · 1:00:52
Last year, Jason Bridwell concluded a five-year search for a business to buy by snatching a 130-year-old custom woodworking company in St. Louis from what he calls the “jaws of…
Oct 23, 2026 · 34:22
This week, we welcome Tanya Ferguson, founder of ClearBrook AI Solutions , who helps small-business owners identify and fix operational problems they may not even realize they…
Oct 20, 2026 · 50:04
This week, David C. Barnett, Jennifer Kerhin, and Rob Levin compare notes on three very different approaches to growth. Dave, convinced that people are craving more personal…
Oct 16, 2026 · 46:25
I don't know any traditional business owner who has devoted more time and energy to figuring out what AI can do for small businesses than Alan Pentz. He's built his own AI…
Oct 13, 2026 · 48:06
This week, Jay Goltz, Lena McGuire, and Jaci Russo tackle three challenges that business owners face, starting with a question that can be especially painful: How do you know…
Oct 9, 2026 · 44:48
This week, we talk to Leisa Peterson, who has spent much of her career thinking about money, risk, and the ways our emotions can interfere with financial decisions. So when…
Oct 6, 2026 · 51:58
This week, we welcome a new regular to the podcast team, Rob Levin, co-founder of WorkBetterNow. I first met Rob more than 20 years ago, when we were both experiencing the…
Oct 2, 2026 · 39:20
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…
Sep 29, 2026 · 48:05
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…
Sep 25, 2026 · 30:32
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…
Sep 22, 2026 · 46:28
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…
Sep 18, 2026 · 33:50
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…
Sep 15, 2026 · 48:44
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…
Sep 11, 2026 · 38:41
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…
Sep 8, 2026 · 53:04
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…
Sep 4, 2026 · 31:11
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…
Sep 1, 2026 · 52:28
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…
Aug 28, 2026 · 39:23
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…
Aug 25, 2026 · 50:21
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…
Aug 21, 2026 · 37:41
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…
Aug 18, 2026 · 43:43
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…
Aug 14, 2026 · 36:42
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…
Aug 11, 2026 · 43:50
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…
Aug 7, 2026 · 33:51
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.…
Aug 4, 2026 · 50:29
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…
Jul 31, 2026 · 39:35
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…
Jul 28, 2026 · 50:46
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…
Jul 24, 2026 · 36:25
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…
Jul 21, 2026 · 59:50
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…
Jul 17, 2026 · 19:31
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…
Jul 14, 2026 · 51:38
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…
Jul 10, 2026 · 31:17
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…
Jul 7, 2026 · 52:07
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…
Jun 30, 2026 · 52:13
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…
Jun 26, 2026 · 39:27
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…
Jun 23, 2026 · 48:03
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…
Jun 19, 2026 · 39:24
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…
Jun 16, 2026 · 53:03
The promise is seductive: Implement the right operating system and your frustrations disappear. Your employees become more accountable. Communication improves. Growth follows.…
Jun 12, 2026 · 37:18
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…
Jun 9, 2026 · 51:00
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…
Jun 5, 2026 · 38:15
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…
Jun 2, 2026 · 48:31
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,…
May 29, 2026 · 32:51
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…
May 26, 2026 · 50:16
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…
May 22, 2026 · 30:35
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…
May 19, 2026 · 49:13
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…
May 15, 2026 · 31:02
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.…
May 12, 2026 · 48:31
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…
May 8, 2026 · 26:30
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…
May 5, 2026 · 43:10
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…
May 1, 2026 · 50:04
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…
Apr 28, 2026 · 48:45
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…
Apr 24, 2026 · 24:09
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…
Apr 21, 2026 · 52:16
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…
Apr 17, 2026 · 34:34
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,…
Apr 14, 2026 · 45:52
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…
Apr 10, 2026 · 32:44
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…
Apr 7, 2026 · 54:06
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…
Apr 3, 2026 · 34:58
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…
Mar 31, 2026 · 49:54
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…
Mar 27, 2026 · 39:09
Chris Campbell started his first business at 18 and has since built and sold companies in landscaping, construction, furniture, and marketing. After his most recent exit, he…
Mar 24, 2026 · 49:47
Given everything going on in the world, you might expect a rough start to the year. But for Paul Downs, Jennifer Kerhin, and Jaci Russo, 2026 has actually begun quite well. In…
Mar 20, 2026 · 45:21
For most business owners, rewarding employees for doing their jobs well is just common sense. Hit your numbers, get a bonus. Sell more, earn more. Perform better, get paid more.…
Mar 17, 2026 · 45:33
It’s already been quite a decade for owners: a pandemic, inflation, tariffs, and now, suddenly, war with Iran—bringing with it the biggest spike in oil prices ever. And looming…
Mar 13, 2026 · 21:36
It does in this sense, says Victor Hwang, founder of Right to Start, an advocacy group that works to expand entrepreneurial opportunity: While starting a business can be…
Mar 10, 2026 · 43:19
Despite the waves of uncertainty crashing across the economy, this week we hear from three owners who feel cautiously good about how their year has started. David C. Barnett…
Mar 6, 2026 · 32:18
In this sponsored conversation, Mike Butler, CEO of Grasshopper Bank , argues that business owners shouldn’t have to choose between speed and stability when it comes to their…
Mar 3, 2026 · 42:24
For the past six years, we’ve done our best to avoid talking politics on this podcast. By focusing on the business realities owners confront every day, we’ve tried to create a…
Feb 26, 2026 · 43:51
A lot of business owners are taking a wait-and-see approach with artificial intelligence. They’ve heard the hype—but they’ve also heard about the slop, the hallucinations, and…
Feb 24, 2026 · 25:17
Yes, says Gene Marks in this week’s Dashboard, the Supreme Court’s tariff decision, while correct, has created a mess. No, you shouldn’t make any plans to spend your tariff…
Feb 20, 2026 · 36:03
Sooner or later, most business owners run into the same unsettling question: How do I actually get out of this thing? Pass it to family? Sell to a competitor? To key employees?…
Feb 17, 2026 · 52:47
Sometimes the best conversations start with a simple question—and then another, and another. This week, we put Kate Morgan, Jaci Russo, and Ted Wolf in the hot seat and fire…
Feb 13, 2026 · 32:57
Kelly Berry’s introduction to small-business ownership came at a moment when most new parents are focused on something else entirely. She had just come home from the hospital…
Feb 10, 2026 · 46:52
Almost every growing business experiences a moment when success starts creating as many problems as it solves. Sales are up. The team is bigger. The product line is broader. And…
Feb 6, 2026 · 30:38
For most business owners, growth is the goal. More customers. More revenue. Bigger numbers. Bigger opportunities. And often, more pressure. But what if the way most of us think…
Feb 3, 2026 · 50:40
Alan Pentz is convinced a wave of disruption is about to crash into small businesses—and he’s doing everything he can to warn owners before it hits. He’s writing, teaching,…
Jan 30, 2026 · 42:03
Ryan Markewich knows the landscaping business from the inside. He built and sold a successful landscaping company in British Columbia, then spent years coaching owners of all…
Jan 27, 2026 · 46:29
Things are suddenly moving fast at Sarah Segal’s San Francisco PR firm. Several new clients look likely to sign on, and for the first time in a while, growth feels real. Which…
Jan 23, 2026 · 48:49
Over the past six years, Teamshares has quietly been running an ambitious experiment in small-business ownership. The company has bought some 90 businesses—promising never to…
Jan 20, 2026 · 46:31
Six years ago, Kate Morgan walked away from the sale of her business just days before closing. Since then, she’s endured some rough stretches, fighting through the pandemic and a…
Jan 16, 2026 · 31:43
This week, Gene Marks makes the case for optimism. There are all sorts of obvious issues to be concerned about but Gene cites a series of reasons his clients are expecting good…
Jan 13, 2026 · 48:57
Most business owners say they do. They tell themselves they just need to get through this one crisis, this one launch, this one quarter—and then life will settle down. But what…
Jan 9, 2026 · 28:13
This week, Karla Trotman, owner of Electro Soft, a contract manufacturing business outside of Philadelphia, talks about the series of contradictions and tough calls she…
Jan 6, 2026 · 51:48
For years, business owners have been told to follow a familiar playbook when it comes to hiring: Take your time. Be selective. Hire slow, fire fast. But more and more owners are…
Jan 2, 2026 · 36:38
This week, Adam Russo, co-founder and owner of The Phia Group , explains how his company helps employers reduce their healthcare expenses. The key, he says, is to educate and…
Dec 30, 2025 · 1:02:55
This week, we take another look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges,…
Dec 26, 2025 · 20:12
This week, Gene Marks tells us it’s late, but it’s not too late to reduce this year’s tax bill. There are still steps you can take, including writing off receivables and…
Dec 23, 2025 · 1:10:35
This week—and next week—we take a look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult…
Dec 19, 2025 · 21:28
As the year comes to a close, I often reach out to John Arensmeyer, who is founder and CEO of Small Business Majority, to get his take on the state of small businesses in…
Dec 16, 2025 · 44:32
This week, special guest Rich Jordan takes us inside a marketing challenge presented by his successful acquisition of home services businesses. Do you keep the legacy names of…
Dec 12, 2025 · 22:51
Most business owners know they should build a forecast for 2026. But many won’t—because it feels intimidating and time-consuming, and let’s be honest, it’s almost guaranteed to…
Dec 9, 2025 · 50:09
This week, in Episode 273, David C. Barnett, Paul Downs, and Sarah Segal tackle health insurance, one of the least enjoyable issues business owners confront. It’s renewal season,…
Dec 5, 2025 · 33:29
This week, Brandon Gray, a partner with CRI Simple Numbers, talks about how his firm tracks the performance of what he calls the entrepreneurial economy. As we all know, what’s…
Dec 2, 2025 · 58:57
This week, we’re replaying one of my favorite conversations of the year, a Q&A session we recorded in May at our 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig,…
Nov 28, 2025 · 30:54
This week, Rob Levin, who is co-founder of WorkBetterNow and who has just published a new book, the “New Talent Playbook,” talks about what he considers to be a talent crisis for…
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