21 Hats Podcast

21 Hats
undefined
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.
undefined
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.
undefined
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.
undefined
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.
undefined
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.
undefined
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.
undefined
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.
undefined
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.
undefined
12 snips
Jun 3, 2025 • 59min

‘Mom, I Am Not Taking the LSAT’

In this engaging conversation, Ari Weinzweig, co-founder of Zingerman's Community of Businesses, shares insights from his 43-year journey building a thriving collection of co-owned enterprises in Ann Arbor. He discusses the challenges and rewards of fostering partnerships and the importance of internal innovation. Ari emphasizes the role of attention to detail in restaurant success and the dynamics of navigating pricing post-pandemic. His candid approach makes for a lively exploration of business philosophy and sustainability.
undefined
Jun 2, 2025 • 29min

Dashboard: The Best Kept Secret in Business Lending

Sahra Halpern, CEO of the Business Consortium Fund, champions community development through financial inclusion. She explains how CDFIs differ from traditional banks, focusing on personalized support for underserved entrepreneurs. Sahra highlights the unique challenges these business owners face and showcases inspiring success stories, including transformative loan experiences. Listeners will learn about the evolving landscape of alternative lending and the vital role CDFIs play in empowering small businesses to thrive despite economic hurdles.

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app