21 Hats Podcast

Last September, we hosted a 21 Hats Brainstorm podcast episode in which BaLeigh Waldrop told us that she was considering buying the family business from her parents. BaLeigh, who has been serving as chief financial officer of the Miller Waldrop furniture business that her great grandfather started, recognized that she was being offered a remarkable opportunity, but she had some concerns. Sales have been off of late, the business is predominantly brick-and-mortar, and most importantly, she would have to work out an ownership structure with her younger brother. The 21 Hats crew of owners and entrepreneurs who joined the brainstorm asked a lot of good questions and offered smart suggestions. “I think what's actually incredibly hard about this whole thing is that I love it,” says BaLeigh. “I love wearing the different hats. I love owning a business in a small community.” We left it that BaLeigh would get back to us once she’d figured things out. In this week’s episode, she returns to tell Jay Goltz and the rest of us what she’s decided.

Frank Rimalovski, head of the NYU Entrepreneurial Institute and the NYU Innovation Venture Fund, shares his insights on teaching entrepreneurship. He discusses the paradox of sometimes advising against starting a business, emphasizing the importance of resilience and customer discovery. Rimalovski also evaluates the double-edged sword of venture capital, stressing the need for startups to build a strong foundation before scaling. Finally, he explores how artificial intelligence is reshaping entrepreneurial programs, making market research and strategic planning more efficient.

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.

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.

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.

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.

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.

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.

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.

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.