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
9 snips
Dec 9, 2025 • 50min
The Healthcare Dilemma: Protect Employees? Or the Business?
David C. Barnett, a Canadian business broker, shares insights on the complexities of healthcare with Paul Downs, a CEO facing soaring insurance premiums, and Sarah Segal, a PR agency owner. They delve into the challenges of rising health insurance costs, with Paul bracing for hefty increases. David contrasts Canada’s universal system with U.S. volatility, while Paul emphasizes responsible employer-paid coverage. They also discuss the intricacies of business exits, revealing the importance of owning a business over merely selling it and the significance of client diversification for sustainability.
13 snips
Dec 5, 2025 • 33min
Dashboard: Tracking the Entrepreneurial Economy
Brandon Gray, a partner at CRI Simple Numbers and a business profitability consultant, delves into the current state of the entrepreneurial economy. He highlights a troubling performance trend among smaller businesses, contrasting it with Wall Street metrics. Brandon discusses critical financial metrics, the divide between thriving large firms and struggling smaller ones, and offers actionable advice for owners to adapt their strategies. He cautions that without significant economic catalysts, the outlook for 2026 may remain dim.
Dec 2, 2025 • 59min
Best of: We Charge What We Need to Charge
In this engaging discussion, Ari Weinzweig, co-founder of Zingerman’s Community of Businesses, shares valuable insights on pricing strategies and the necessity of charging what you need to sustain a business. He explains how to define company culture by boundaries and reflects on his 47-year partnership with Paul Saginaw, rooted in shared vision. Ari emphasizes the importance of employee ownership and attention to detail for consistent customer experiences. He also discusses the lessons learned from both failures and successes over the decades.
13 snips
Nov 28, 2025 • 31min
Dashboard: Finding Employees Is Harder than Finding Customers
Rob Levin, co-founder of Work Better Now and author of The New Talent Playbook, dives into the talent crisis affecting small businesses. He explains that recent layoffs don’t necessarily yield the right hires for smaller firms. Levin highlights the importance of a purposeful company culture and effective employer branding to attract talent. He advocates for paying competitive wages and emphasizes upskilling and internal mobility over mere salary increases. Additionally, he champions remote work, urging a focus on outputs rather than physical presence.
9 snips
Nov 25, 2025 • 49min
I Have to Figure This Sh*t Out
Liz Piccarazzi, CEO of CityBin, shares her struggle with AI adoption amidst a $400,000 tariff bill, while Jaci Russo, CEO of Brand Russo, boasts about her successful integration of generative AI that generates ten vetted leads daily. Ted Wolf, an AI consultant, stresses the importance of documentation in AI workflows. The trio reflects on a challenging year, with Jaci lamenting a failed hire and Liz humorously acknowledging the reliability of New York City's trash. Together, they navigate the complexities of AI in their businesses.
8 snips
Nov 21, 2025 • 33min
Dashboard: Want More Domestic Manufacturing? Think Small
Ilana Preuss, Founder and CEO of Recast City, advocates for revitalizing local economies through small-scale manufacturing. She argues that instead of chasing large corporations, communities should focus on their own local manufacturers. By listening to the needs of these businesses, towns can fill vacant storefronts and create rooted jobs. Preuss shares success stories like a shared kitchen in Columbia, Missouri, and emphasizes the importance of tailored support and responsive local policies to foster growth in product-based businesses.
13 snips
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.
