21 Hats Podcast

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.

This week, in Episode 246, we meet Ben Knepler, who, along with his True Places co-founder Nelson Warley, came up with an idea for an outdoor chair that they believe could be a game-changer. They liked the idea so much that they quit their corporate jobs, they raised money, they borrowed money—putting their own homes at risk—they fought through the pandemic, they found a manufacturer in China, they launched on Kickstarter, they found another manufacturer in Cambodia, and then they ran smack into the brick wall of President Trump’s second-term tariffs. Or, as George Harrison almost put it, “If you try to sit, I’ll tax your … sturdy, portable, folding chair that could create a whole new category of high-end outdoor products except you’ll probably have to try to sell them in some other country … ‘cause I’m the tariff man.”

This week, Gene Marks -- normally a fan of automating anything that can be automated — says it’s too soon to think about turning important tasks over to artificial intelligence bots, mostly because they’re still making too many mistakes. In fact, Gene cites a survey of business leaders who said they came to regret offloading employees in favor of AI. In many cases, those leaders wound up trying to re-hire their employees. Plus: Gene also talks about how businesses using AI can get into regulatory trouble if they’re not careful.