21 Hats Podcast
21 Hats
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.
Episodes
Mentioned books
May 20, 2025 • 46min
We Get Paid to Judge People
This week, in Episode 247, we welcome a new regular, Kate Morgan, who joins the podcast along with Paul Downs and Jay Goltz. Kate is the CEO and founder of Boston Human Capital Partners, which provides recruiting and HR services, mostly to other small businesses. After a very difficult stretch caused by the pandemic, Kate’s business has been growing again – but Paul and Jay think she’s leaving money on the table. They think she needs to raise her prices. “I mean,” responds Kate, “we're growing in an industry that we're seeing shrinking right now, and so it's one of these things: Do I want to scare the squirrels and jump up our prices? That's where I've been struggling.” Plus: Are HR people supposed to protect the employees or the business? And after having to lay off a third of his workforce, Paul gives us an encouraging update on how his business is doing.
6 snips
May 19, 2025 • 24min
Dashboard: A Glimmer of Hope for Small Businesses
John Arensmeyer, Founder and CEO of Small Business Majority, shares invaluable insights on the pressing needs of small business owners. He discusses the challenges they face in accessing capital and highlights recent bipartisan efforts to protect funding sources like the CDFI fund. Arensmeyer emphasizes the importance of reforming tax benefits, particularly the 199A deduction, to better support smaller businesses. He ends on a hopeful note, showcasing examples of legislative cooperation that could pave the way for a brighter future for entrepreneurs.
May 13, 2025 • 53min
‘I’ll Tax Your Seat’
This week, in Episode 246, we meet Ben Knepler, who, along with his True Places co-founder Nelson Warley, came up with an idea for an outdoor chair that they believe could be a game-changer. They liked the idea so much that they quit their corporate jobs, they raised money, they borrowed money—putting their own homes at risk—they fought through the pandemic, they found a manufacturer in China, they launched on Kickstarter, they found another manufacturer in Cambodia, and then they ran smack into the brick wall of President Trump’s second-term tariffs. Or, as George Harrison almost put it, “If you try to sit, I’ll tax your … sturdy, portable, folding chair that could create a whole new category of high-end outdoor products except you’ll probably have to try to sell them in some other country … ‘cause I’m the tariff man.”
May 12, 2025 • 28min
Dashboard: They Should Have Fired Themselves
This week, Gene Marks -- normally a fan of automating anything that can be automated — says it’s too soon to think about turning important tasks over to artificial intelligence bots, mostly because they’re still making too many mistakes. In fact, Gene cites a survey of business leaders who said they came to regret offloading employees in favor of AI. In many cases, those leaders wound up trying to re-hire their employees. Plus: Gene also talks about how businesses using AI can get into regulatory trouble if they’re not careful.
May 6, 2025 • 51min
Maybe Earnouts Aren’t as Bad as You Think
This week, in Episode 245, a new regular, David Barnett, joins the podcast along with Jaci Russo and William Vanderbloemen. David, who has been a guest on the podcast before, helps people buy and sell businesses—but, as he explains, he’s not a business broker. He’s found a different business model. David, Jaci, and William discuss why it’s so hard to sell a business, what owners can do to make their businesses more attractive to buyers, and why it can be in everyone’s interest for sellers to accept an earnout. Plus: Jaci talks about why she used a recruiter to help her hire a business development person and why she ended up choosing someone who checked none of the boxes she initially thought most important. “I thought I needed some hotshot East Coast, West Coast, big city dude who came in with all the slick talk,” she tells us. Instead, she found her winner in rural Alabama.
May 5, 2025 • 24min
Dashboard: There’s Still a Talent Crisis for Small Businesses
This week, Rob Levin, co-founder and chairman of WorkBetterNow, talks about why he sees business owners—despite the uncertain economy—still struggling to fill key roles. He also discusses the importance of creating a culture by design, how owners can manage their profiles on Glassdoor, and what he thinks of Gen Z employees. Plus: Rob explains how he’s been infusing AI into all aspects of running his business.
Apr 29, 2025 • 45min
Dear ChatGPT: What Are My Blind Spots?
This week, in Episode 244, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It was right on,” she tells us. “I mean, it was totally, absolutely true.” We even brought ChatGPT into our conversation in real time, asking it whether Jaci had hired the right business development person, whether Sarah had been fully prepared two years ago to buy back her PR firm, and what’s the best podcast for small business owners. Plus: while we were talking, Jaci asked ChatGPT to evaluate the performance of her co-founder and spouse, MIchael. Let’s just say, it does have some concerns.
Apr 28, 2025 • 29min
Dashboard: A Tech Update for Small Business Owners
This week, Gene Marks highlights some recent tech developments, including: Quickbooks is selling a lifetime version of its software for just $250. Microsoft has reintroduced its somewhat controversial Recall AI tool, which captures and indexes screenshots of user activity every three seconds—a function that is intended to improve cybersecurity but that has raised some interesting questions. Plus: Gene explains how—if you have the time and money—you can now connect the various software platforms you use and turn them into a smart AI assistant.
Apr 22, 2025 • 49min
I’d Love to Manufacture in the U.S.
This week, in Episode 243, Liz Picarazzi tells Sarah Segal that she’s taking another pass at finding a domestic fabricator. Maybe it’s wishful thinking, Liz says, but she’s hoping that now that her business is more established, she just might find an American factory that wants to partner with a growing business and would be eager to help her re-shore her manufacturing. She’s also decided she’s going to keep speaking out about the tariffs despite the hate mail she’s been getting: “I'm not going to be ashamed of manufacturing in Asia,” she tells us. “I had my reasons, and they were very good reasons.” Plus: Sarah talks about how she’s been using AI, including to create her own GPTs, which help her promote her clients. She’s also found a software platform she loves that makes it easier to find and file requests for proposals.
Apr 21, 2025 • 33min
Dashboard: Every Business Has a Story to Tell
But not every business knows how and where to tell it? This week, Sarah Segal talks through what business owners should know about public relations: How can they get better at explaining what they do? How can they figure out what others will find interesting about their business? Should they share their story themselves or reach out to a journalist? If they decide to reach out to a journalist, should they do it themselves or hire a PR person to do it? If they decide to hire a PR person, how much should it cost?
