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
18 snips
Jan 23, 2026 • 49min
Dashboard: A Grand Experiment in Buying and Building Small Businesses
Michael Brown, co-founder and CEO of TeamShares, runs a company that buys small firms and converts them to employee ownership. He discusses scaling a public holding-company model, why they plan to go public while keeping long-term ownership, lessons from buying 90 businesses, low failure rates and high retention, and how employee ownership and practical AI shape outcomes.
13 snips
Jan 20, 2026 • 47min
I’m Looking for an Exit
In this insightful discussion, Kate Morgan, CEO of Boston Human Capital Partners and newly published author, explores her desire for a strategic exit after years of tough conditions. She shares her previous near-sale experience while David C. Barnett and Ted Wolf weigh in with practical advice on selling strategies and publishing journeys. They discuss the pitfalls of selling, the importance of quality-of-earnings, and the emotional challenges post-exit. Additionally, the trio dives into their unique publishing experiences, highlighting contrasting methods and outcomes.
13 snips
Jan 16, 2026 • 32min
Dashboard: Why 2026 Will Be a Big Year for Small Businesses
Gene Marks, a CPA and small-business commentator, brings a refreshing wave of optimism regarding the future for small businesses. He discusses upcoming tax cuts that may stimulate consumer spending, particularly in 2026. Gene also analyzes new tax rules affecting overtime and tips, projecting potential refunds for employees. He predicts falling inflation and interest rates could revive housing demand. Additionally, he highlights how AI adoption will enhance productivity, offering real examples of businesses benefiting from replacing traditional roles with technology.
12 snips
Jan 13, 2026 • 49min
Do Business Owners Really Want Balance?
Mel Gravely, the seasoned Chairman of Triversity Construction, joins Ted Wolf, CEO of GuideWise, and Lena McGuire, CEO of Spooka Kitchen and Bath, to explore the elusive concept of balance in entrepreneurship. They candidly discuss whether business owners genuinely desire work-life balance or if it’s merely an expectation. Mel challenges the notion that family time is preferred over work, while Lena emphasizes personal happiness as a priority. They highlight the cyclical nature of business demands and the necessity of redesigning life for mental and emotional health.
9 snips
Jan 9, 2026 • 28min
Dashboard: No Text Book Can Prepare You for This
Karla Trotman, owner of Electrosoft, an electronics contract manufacturing firm, navigates the tumultuous landscape of 2025. She shares her struggles with tariffs that complicated supply chains and decision-making. Rather than laying off employees, Karla chose to keep her skilled workforce, even testing a shift to a 32-hour work week. She highlights the importance of building solid client relationships and contemplates the future of manufacturing ownership. Karla's journey reflects resilience amid contradictory challenges in the industry.
11 snips
Jan 6, 2026 • 52min
The Old Rules of Hiring Are No Longer Working
Paul Downs, CEO of Paul Downs Cabinet Makers, faces staffing challenges in hands-on manufacturing. Jackie Russo, CEO of Brand Russo, champions continuous employer branding and recruitment marketing. William Vanderbloemen, founder of Vanderbloemen Search Group, highlights the increasing fickleness of candidates and critiques the outdated 'hire slow, fire fast' mantra. The trio debates adapting hiring processes, total compensation communication, and the need for agility in today's competitive landscape while preparing for future leadership and AI integration.
10 snips
Jan 2, 2026 • 37min
Dashboard: This Company Covers All of Its Employees’ Health Care
Join Adam Russo, co-founder and CEO of The Phia Group, as he dives into innovative strategies for reducing healthcare expenses. He reveals how education and transparency can empower employees to make smarter health choices, leading to remarkable savings, including free care after five years. Adam also discusses how small businesses can benefit from self-funding and risk pooling, tailored plan designs, and the need for raw claims data to identify cost-saving opportunities. His insights are revolutionizing employer health plans!
13 snips
Dec 30, 2025 • 1h 3min
Do You Have the Stomach for This? 2025 in Review, Part 2
Laura Zander, a serial entrepreneur and founder of Jimmy Beans Wool, shares insights on successful exit planning and the nuances of valuation during her sale. Jackie Russo, a marketing agency founder, discusses the lessons learned from a high-priced sales hire that didn't pan out and her innovative AI systems delivering daily leads. Liz Piccarazzi, of CityBin, recounts her intense journey developing bear-resistant bins, highlighted by a close encounter with a grizzly. Mel Gravely talks about shutting down his profitable business due to partner conflicts and personal strains.
9 snips
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.
