21 Hats Podcast

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.

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.

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.

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.

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.

This week, in Episode 248, we bring you a taste of what we experienced at the recent 21 Hats Live event in Ann Arbor, where we did a deep dive into a challenge confronting Mars Chapman, owner of Casey’s New Orleans Snowballs, a snowcone business in Austin, Texas. Mars, who is 36, bought the business from his parents and also inherited from them a somewhat laidback approach to ownership. The business has been operating for 29 years, but it has generally run only eight months of the year, which has been enough, thus far, to support a comfortable lifestyle for its owners. But Mars, whose wife, Page, works for a nonprofit and who is pregnant with their first child, has begun to question whether his current approach will be enough to support a family. This is another in our series of 21 Hats Brainstorms—we used to call them Fish Bowls—in which we pair an owner facing a challenge with a group of entrepreneurs eager to help. We ask questions, break into small groups to exchange ideas, and then report back. Sometimes—as I personally experienced at last year’s 21 Hats Live event—the comments and suggestions can be challenging, even a little painful to hear. But they’re always constructive.

This week, Lance Tyson, founder of the Tyson Group sales consultancy, talks about how he’s using generative AI in his own business along with his suggestions for owners who are just getting started with AI. Among his suggestions: ask ChatGPT how best to use ChatGpt. Lance also talks about how salespeople can best navigate a business environment struggling with tariffs, uncertainty, rising prices, and talk of recession. One tip: don’t just accept an email rejection. Try to get them on the phone.

This week, in Episode 247, we welcome a new regular, Kate Morgan, who joins the podcast along with Paul Downs and Jay Goltz. Kate is the CEO and founder of Boston Human Capital Partners, which provides recruiting and HR services, mostly to other small businesses. After a very difficult stretch caused by the pandemic, Kate’s business has been growing again – but Paul and Jay think she’s leaving money on the table. They think she needs to raise her prices. “I mean,” responds Kate, “we're growing in an industry that we're seeing shrinking right now, and so it's one of these things: Do I want to scare the squirrels and jump up our prices? That's where I've been struggling.” Plus: Are HR people supposed to protect the employees or the business? And after having to lay off a third of his workforce, Paul gives us an encouraging update on how his business is doing.

John Arensmeyer, Founder and CEO of Small Business Majority, shares invaluable insights on the pressing needs of small business owners. He discusses the challenges they face in accessing capital and highlights recent bipartisan efforts to protect funding sources like the CDFI fund. Arensmeyer emphasizes the importance of reforming tax benefits, particularly the 199A deduction, to better support smaller businesses. He ends on a hopeful note, showcasing examples of legislative cooperation that could pave the way for a brighter future for entrepreneurs.