
21 Hats Podcast
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.
Latest episodes

Jul 8, 2025 • 50min
Straight Talk About ESOPs and Co-Ops and EOTs, Oh My!
John Abrams, a seasoned founder, author, and advocate for sustainable business practices, joins Mel Gravely and Jay Goltz, leaders in the construction industry, for an engaging discussion on employee ownership models. They explore strategies to avoid disastrous private equity sales and share insights on why there are so few employee-owned businesses. The trio dives into the nuances of ESOPs versus co-ops, addressing both potential benefits and challenges. Their candid conversation highlights the importance of succession planning while keeping business values intact.

Jul 7, 2025 • 43min
Dashboard: A Big Beautiful Win for Small Businesses?
Gene Marks, a CPA and small business advocate, dives into the recent tax changes from Trump's legislative proposal, pointing out the newfound tax certainty for business owners. He details the small business deduction and estate tax exemptions while encouraging owners to take responsibility for managing tariff complaints. Marks emphasizes understanding the nuances in economic policies that affect healthcare and inflation. The conversation balances optimism with the realities of navigating current financial uncertainties.

4 snips
Jul 1, 2025 • 57min
Something’s Happening in the Job Market
In this engaging discussion, Paul Downs, a custom furniture maker, shares his surprising spike in job applications and explores implications for hiring practices with Kate Morgan, an HR expert, and Liz Piccarazzi, who manufactures trash and package bins. They discuss the balance between what companies offer vs. expectations, the impact of AI on job security, and the emotional strain of rejecting qualified candidates. Additionally, Liz provides a cheerful update on her tariff situation, while they weigh the risks of starting a business in today's economy.

Jun 30, 2025 • 23min
Dashboard: Three Metrics for ‘White Knuckle’ Times
This week, Tracy Bech, co-author of “The 60-Minute CFO,” tells us that she normally recommends that business owners check 14 performance measures on a regular basis. But during uncertain times like these, Tracy says, there are three in particular to keep an eye on: gross profit margin, operating cash flow, and current ratio. In our conversation, she explains how they work, what they mean, and what to do if they’re flashing red. She also says you can download a free tool to track your cash flow at 60minutecfo.com.

Jun 24, 2025 • 54min
Why Don’t You Just Sell the Business?
This week, in Episode 252, David Barnett, Mel Gravely, and Kate Morgan discuss a somewhat unusual approach to succession, which is to not sell the business. Basically, it’s about taking a step back from leadership while maintaining ownership, and both Kate and especially Mel are moving in this direction. The approach can pay off financially in part because businesses often are worth more to the owner than they would be to a buyer. Why is that? As David explains, the business that the buyer buys isn’t really the same business that the owner sells: “If you've owned the business for a long time,” he says, “the balance sheet is probably pretty strong. You've had time to earn money, pay down debts. You’ve got a good equity position. This makes the business strong, and it makes it better able to weather storms. If I were to come along and buy Mel's business, I would come together on a price, and I would pay Mel. But a good chunk of that money would probably be borrowed. Now, I would have a much weaker balance sheet than what Mel enjoys today. And a big chunk of the cash flow that he currently enjoys, I would end up giving to my bank.” Of course, this approach to succession does have some challenging elements, including finding someone to run the business. Plus: We also discuss whether it’s possible to sell a solopreneur business.

Jun 23, 2025 • 26min
Dashboard: Don’t Believe the AI Hype (Yet)
Gene Marks, a CPA and seasoned small business commentator, shares his skepticism about AI-driven layoffs in corporate America, arguing that CEOs are often diverting attention from poor management. He emphasizes the folly of replacing human workers with AI and encourages a more balanced approach to integration. Marks discusses practical ways he's incorporating AI into his own business, revealing opportunities for productivity and efficiency without succumbing to fear. His insights prompt a critical examination of AI's true role in the workplace.

9 snips
Jun 17, 2025 • 47min
‘America Sucks at Small Business’
Dan Carmody, the former CEO of Detroit's Eastern Market, sheds light on small business dynamics in the U.S. vs. abroad. He argues that America falls short in supporting local enterprises, drawing lessons from international practices. The conversation touches on community engagement and the vital role of social media strategies for businesses. Carmody also discusses the emotional journey of entrepreneurs and shares insights on revitalizing local areas through hospitality and ethical practices, advocating for a stronger support system for small businesses.

Jun 16, 2025 • 18min
Dashboard: Introducing America the Entrepreneurial
This week, Victor Hwang tells us that his organization, Right to Start, has big plans for America’s upcoming 250th birthday. Spurred largely by the widespread sense that the American Dream has lost some of its luster, Victor and Right to Start are launching a campaign to turn our semiquincentennial into a celebration of America’s entrepreneurial roots and a push to remove the barriers that make it harder than it should be to start and build a business. One key focus: finding ways to make it easier for businesses to raise capital. You can learn more here.

13 snips
Jun 10, 2025 • 55min
‘The General Purpose Agency Is Doomed’
Alan Pentz, founder of Corner Alliance and The Owner Institute, dives into the potential demise of B2B agencies due to the rise of generative AI. He argues that companies may prefer AI over traditional agency retainers. Jaci Russo, CEO of Brand Russo, shares insights on leveraging AI for better business practices, while Sarah Segal, CEO of Siegel Communications, discusses the enduring significance of human relationships in PR amidst AI's growth. Together, they explore the balance between technology and personal connections in the evolving business landscape.

5 snips
Jun 9, 2025 • 19min
Dashboard: Is the GOP Tax Bill Good for Business?
Gene Marks, a CPA and prolific writer for outlets like Forbes and The Guardian, shares his insights on the GOP tax bill's implications for small businesses. He discusses the potential benefits, including enhanced pass-through and first-year capital deductions. However, he warns about the hidden challenges it poses, particularly for nonprofits and service industries. Marks argues that while there are advantages, the bill could lead to significant long-term issues for entrepreneurs, especially in light of rising national debt and interest rates.