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
Aug 25, 2025 • 40min
Dashboard: A Business Owner Exits on His Own Terms
This week, Jimmy Kalb tells us how he built his electrical component business and, perhaps even more impressively, how he put a plan in place that has allowed him to walk away from his CEO role at the relatively young age of 63. One key: Jimmy has long been a process guy. For years, he’s been creating processes and handing them over to someone else to manage -- until he left himself with not all that much to do. Another factor: He only hires people right out of school, which is why his successor is in his early 30s and has never worked anywhere else.
Aug 19, 2025 • 47min
It’s a Bear Market for Citibin
This week, in episode 260, Liz Picarazzi tells Jay Goltz and William Vanderbloemen that she’s had a couple of big breakthroughs. For Liz, it’s been a challenging few years dealing with the tariffs while also trying to break into a promising new market. Despite the advice of some very smart people who encouraged her to conquer her first market —urban areas plagued by rats—before expanding into additional markets, Liz has spent several years trying to position Citibin to serve towns, parks, and resorts that need trash bins strong enough to withstand bears. For that investment to pay off, however, Liz would have to outsmart her nemesis, an especially ferocious competitor that goes by the name of Seeley. Plus: Jay talks about the plight of small retailers trying to survive while their industry collapses around them. And William tells us how he’s trying to keep up in the AI arms race between employers and employees.
Aug 18, 2025 • 25min
Dashboard: Can AI Save Small Businesses from Google?
Gene Marks, a seasoned CPA and writer for The Guardian, shares his insights on the struggles small business owners face with Google’s advertising monopoly. He discusses the potential of AI to disrupt this dominance, highlighting how tools like ChatGPT can reshape discoverability. Marks advocates for using YouTube as a more effective platform for promotion, emphasizing advantages like targeted advertising and tutorial videos. He also touches on professionalism in handling layoffs and the discomfort of sharing personal experiences in the digital age.
Aug 12, 2025 • 44min
When Your Biggest Hire Ever Is a Bust
This week, in episode 259, Jaci Russo tells David C. Barnett and Kate Morgan how the hiring of her agency’s first top-level sales person went wrong. About four months ago, when Jaci first told us about this big step, she sounded thrilled. She said her new sales chief was a delight to be around, had hit the ground running, and had already lined up at least one impressive client. Unfortunately, none of that panned out. But Jaci, who is hardly the first business owner to have an important placement go off the rails, offered to walk us through her process to see what lessons we can all learn: Were the interviews flawed? Was the onboarding effort insufficient? Was it the executive recruiting firm she used? Was it the compensation structure? Or was it the remote-work arrangement? Plus: We also discuss the mounting evidence that companies have stopped filling entry-level positions. And should that trend continue, where will owners find the next generation of leaders?
Aug 11, 2025 • 27min
Dashboard: Any Business Can Afford This CFO
This week, Tracy Bech explains how and why she spent six months building, training, and testing her brand new 60 Minute Custom GPT, which is essentially an AI CFO that can perform all kinds of financial analysis on your business. You can interact with it as easily and conversationally as you do with ChatGPT, and it can help you figure out why your margins are off, or how you should expect to perform next quarter, or whether that new service you plan to offer will be profitable. And it’s free.
Aug 5, 2025 • 49min
Laura Zander Named Her Exit Price
Laura Zander, former CEO of Jimmy Beans Wool and now chief brand officer of Local Crafts Group, shares her journey of selling her successful yarn business at the right price. She reveals how she strategically networked potential buyers and the emotional challenges tied to the sale. Alongside her, Jennifer Kerhin, CEO of SB Expos and Events, discusses an unexpected personal crisis as her home caught fire. Their stories highlight resilience, the importance of financial health, and the vital role of community support during tough times.
Aug 4, 2025 • 22min
Dashboard: ‘We’re Not Giving Up’
This week, Ben Knepler returns to the podcast to explain why he and his co-founder at True Places concluded they had no choice but to suspend production of their portable, outdoor chairs and go into survival mode. Initially, they manufactured the chairs in China, where they’ve been paying tariffs since the first Trump administration. Last year, at considerable expense, they moved production to Cambodia, which at the time was subject to no tariffs. But since April 2nd, the company has been subjected to a tariff rate that has gyrated from zero to 49 percent to 10 percent to 36 percent to 19 percent as of last week. In our conversation, Ben explains why they stopped production and how they hope to survive.
Jul 29, 2025 • 45min
Those Who Can, Do. Those Who Can’t, Uh, Coach?
David C. Barnett, a business acquisition expert, joins Jay Goltz, a Chicago-based CEO, and Lena McGuire, a remodeling innovator, to discuss the tricky world of hiring coaches. They debate the importance of coaches having industry-specific knowledge and personal success. Jay hilariously critiques unqualified coaches in his industry while Lena shares how transformative good coaching can be. The trio also laughs about Jay's whimsical idea of opening a pizza shop, blending personal anecdotes with key insights on business growth and support networks.
Jul 28, 2025 • 25min
Dashboard: A Few Ideas to Really Help Small Businesses
Peter Koehler, founder of Lumo Group, specializes in helping businesses with operations and finances. He emphasizes that small businesses are uniquely different from large corporations and suggests that the federal tax code should reflect this. Koehler advocates for tiered payroll tax rates, a startup tax credit for professional services, and changes to the qualified business income deduction to combat growing consolidation. He also highlights the importance of supporting low-margin businesses as vital community resources, calling for policies that empower small enterprises.
5 snips
Jul 22, 2025 • 46min
How Many Clients Did That Post Bring You?
This week features David C. Barnett, a business broker from Canada, Kate Morgan, CEO of Boston Human Capital Partners, and Sarah Segal, a PR expert from San Francisco. They dive into their varied marketing strategies on LinkedIn, debating whether likes or actual sales matter more. David contrasts his free self-publishing approach with Kate's hefty book expense. Meanwhile, Sarah takes a different route by investing in a VP instead of a book. It’s a vibrant chat on what truly drives business success and the value of genuine connections.
