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
Dec 30, 2025 • 1h 3min
Do You Have the Stomach for This? 2025 in Review, Part 2
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, including Laura Zander on how she got the price she wanted to sell Jimmy Beans Wool, Liz Picarazzi on her confrontation with a grizzly bear, Jay Goltz on why he just might be a good candidate to turn his business into a worker cooperative, Mel Gravely on why he sold his facilities-management business as soon as it became profitable, and Jaci Russo on how she figured out how to train a series of AI agents to deliver 10 client leads first thing every morning.
Dec 26, 2025 • 20min
Dashboard: You Can Still Save on 2025 Taxes!
Gene Marks, a CPA and small-business columnist, shares valuable insights on tax strategies for business owners. He emphasizes that it's not too late to reduce your tax bill for this year by writing off receivables and old inventory or contributing to retirement plans. Marks also discusses the benefits of retroactively claiming the R&D tax deduction under recent GOP tax law changes and reevaluates the pass-through business structure versus C-corp options. His practical advice offers a savvy roadmap for navigating the complex tax landscape.
14 snips
Dec 23, 2025 • 1h 11min
Do You Have the Stomach for This? 2025 in Review, Part 1
In this engaging discussion, Paul Downs reflects on tough staffing decisions during a sales drop, emphasizing the importance of empathetic layoff communications. Liz Piccarazzi shares her journey through tariff changes while seeking U.S. manufacturing options for her products. David Barnett offers insights into business valuation, stressing the idea that a company can hold more value for its owner than for potential buyers. Kate Morgan highlights the pitfalls of underpricing in recruiting, sparking a debate about sustainable pricing strategies.
9 snips
Dec 19, 2025 • 21min
Dashboard: This Is Killing Small Businesses
John Arensmeyer, Founder and CEO of Small Business Majority, dives into the troubling state of small businesses in America. He discusses recent survey findings showing revenue and staffing declines. John highlights the heavy burden of rising healthcare costs and reliance on marketplace subsidies. He also addresses the adverse effects of tariffs, immigration roundups, and federal budget cuts on small businesses. Despite these challenges, he notes a surprising optimism among business owners as they prepare for 2026, advocating for their rights and adapting to ongoing disruption.
10 snips
Dec 16, 2025 • 45min
Three Branches, Three Brands: Anatomy of a Rebrand
Rich Jordan, CEO of a multi-branch home services company, shares his journey through a complex rebranding process. He discusses the dilemma of preserving local brand identities versus unifying under a stronger name. Rich reveals how radio advertising effectively captured homeowner customers, contrasting it with the problems of digital lead generation. He emphasizes the importance of authenticity in building a brand that competes with private equity. Finally, he introduces his new brand, High Ground, and outlines the strategic decisions made along the way.
9 snips
Dec 12, 2025 • 23min
Dashboard: Your Forecast Will Be Wrong. Do It Anyway
In this conversation, Tracy Beck—founder of The 60 Minute CFO and coauthor specializing in financial fluency—breaks down the art of forecasting for small businesses. She tackles the common fears that hold owners back and reframes forecasting as a tool for directional planning. Tracy shares a simple three-step process and highlights the importance of team involvement for accurate predictions. With her innovative GPT tool, she showcases how AI can simplify forecasting complexities, enabling business owners to spot opportunities and adjust plans swiftly.
12 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.
