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
Nov 18, 2025 • 45min
She Still Packs Every Order as if It’s a Gift
Channon Kennedy, founder of Kiwi Vision and inventor of the Morgan Square tool, shares her journey of balancing a banking career with her growing hardware business. She discusses the excitement of fulfilling orders and her plans for international expansion. Paul Downs, CEO of a custom cabinet-making business, provides an update on his company's recent sales rebound after facing layoffs. He reveals how shifting military contracts have influenced demand while contemplating staffing decisions amid economic uncertainty. Both guests navigate the challenges of entrepreneurship with resilience.
10 snips
Nov 14, 2025 • 30min
Dashboard: Seeing Past the Workslop and Hallucinations
In this engaging discussion, Gene Marks, a small-business columnist and CPA, dives into the practical use of AI for small businesses. He emphasizes the importance of investing in paid AI tools and training to empower employees. Marks shares impressive examples like using Google Meet's translation features for multilingual meetings and Copilot in OneDrive for efficient resume management. He also highlights the need for businesses to embrace AI cautiously while utilizing their own data for better results. Get ready to amplify productivity!
14 snips
Nov 11, 2025 • 46min
Welcome to Employee Ownership! (Without the Hype)
Kris Maynard, co-founder of Cathedral Holdings, and Justin Jordan, its CEO, explore the intricacies of employee ownership through ESOPs. They candidly discuss the complexities and potential risks, highlighting that not all employees embrace the model. While ESOPs offer tax benefits, they can turn into risky retirement plans if companies falter. Open-book management has greatly engaged employees, shifting perceptions from retirement benefits to ownership mentality. Kris and Justin also share insights on governance measures to protect employee investments.
12 snips
Nov 7, 2025 • 30min
Dashboard: Turning Tradespeople Into Business People
Julian Scadden, President and CEO of Nexstar Network, guides tradespeople in plumbing, HVAC, and electrical fields to become adept business owners. He reveals the significant challenges these businesses face and shares Nexstar's unique member-owned structure that prioritizes community. Julian discusses the tough choice to part ways with PE-backed members to stay mission-focused and emphasizes the importance of structured practices. He also highlights the potential of AI tools for service businesses and advocates for apprenticeship programs to combat technician shortages.
13 snips
Nov 4, 2025 • 43min
I Thought It Was the Worst Day of My Life
Ted Wolf, CEO of GuideWise and former IT staffing entrepreneur, shares his incredible journey of bouncing back from a significant business setback when a key employee took 40% of their revenue. This disaster led him to rethink leadership and profit-sharing. He emphasizes the importance of managing the human side of AI adoption, discussing whether small businesses should retrofit existing tech or start anew. Alongside Jennifer Caron, they explore practical AI applications and advise on strategic integrations for smooth transitions in small businesses.
13 snips
Oct 31, 2025 • 42min
Dashboard: A Business Owner Chooses His Third and Final Act
In this engaging discussion, Josh Patrick, a former vending business owner and consultant, dives into his third act focused on the complexities of retirement and death. A cancer survivor, he candidly shares his fear of retirement and how it links to identity loss. Josh emphasizes the emotional impacts of business on families and advocates for gentler practices in leadership. He explores poignant questions about death rituals and the potential of psychedelics in confronting death anxiety. His insights challenge entrepreneurs to prepare for the personal side of exit strategies.
12 snips
Oct 28, 2025 • 48min
Should I Buy the Building? Or Stick to the Business?
Lena McGuire, CEO of Spoka Kitchen and Bath, shares insights on the benefits of buying commercial real estate for her growing business. Jay Goltz, a retail expert, emphasizes the long-term value of property appreciating beyond business worth. Liz Picarazzi discusses navigating supply-chain challenges and tariffs while showcasing an AI tool that streamlines her sales process. They delve into strategic considerations like financing, location over price, and adapting to market uncertainties to ensure longevity in their respective industries.
13 snips
Oct 24, 2025 • 36min
Dashboard: Even Made in the USA Manufacturers May Not Survive the Tariffs
Greg Shugar, owner of Beau Ties and co-founder of The Tie Bar, dives deep into how tariffs threaten U.S. manufacturers. He explains the irony of needing imported silk while being a domestic producer. A possible 100% tariff looms large, complicating his business planning and profitability. Shugar discusses stockpiling strategies, the challenges of small business lobbying in Washington, and the mixed reception from lawmakers. He passionately argues against offshoring production, emphasizing the impact on brand identity and U.S. jobs.
Oct 21, 2025 • 47min
Do You Want to Serve Clients—or Build a Business?
This week, in episode 267, David C. Barnett, Kate Morgan, and Sarah Segal tackle a challenge every owner who sells services eventually faces: Clients want to hire you, but you want them to understand they’ll mostly be working with your team. How do you make that clear without scaring them off? For some, it’s a delicate balancing act. For Kate, it’s simple: if a client insists on her personal time, she charges, in her words, “a boatload of cash.” Plus: we dive into another tricky owner decision: how to structure bonus plans that truly drive retention. David is weighing a deferred bonus approach, where payouts happen over several years. It’s a proven way to keep people around, but he wonders: Do you really want employees who’d otherwise leave to stay just for the money? Also, when valued employees get an offer, do you counter-offer? And if they leave, do you tell them they can always come back?
Oct 14, 2025 • 45min
Your Employees Want a Career Path. Can You Keep Them?
Join Jay Goltz, a seasoned entrepreneur and CEO of The Goltz Group, David C. Barnett, a business broker and advisor from Canada, and Kate Morgan, CEO of Boston Human Capital Partners. They dive into the struggle of crafting employee career paths while staying true to company goals. Jay highlights the importance of letting employees experiment, while David warns that businesses risk obsolescence without evolution. Kate shares her experiences of stress during rapid growth, touching on employee retention and the art of thorough onboarding.
