21 Hats Podcast

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.

This week, in Episode 245, a new regular, David Barnett, joins the podcast along with Jaci Russo and William Vanderbloemen. David, who has been a guest on the podcast before, helps people buy and sell businesses—but, as he explains, he’s not a business broker. He’s found a different business model. David, Jaci, and William discuss why it’s so hard to sell a business, what owners can do to make their businesses more attractive to buyers, and why it can be in everyone’s interest for sellers to accept an earnout. Plus: Jaci talks about why she used a recruiter to help her hire a business development person and why she ended up choosing someone who checked none of the boxes she initially thought most important. “I thought I needed some hotshot East Coast, West Coast, big city dude who came in with all the slick talk,” she tells us. Instead, she found her winner in rural Alabama.

This week, Rob Levin, co-founder and chairman of WorkBetterNow, talks about why he sees business owners—despite the uncertain economy—still struggling to fill key roles. He also discusses the importance of creating a culture by design, how owners can manage their profiles on Glassdoor, and what he thinks of Gen Z employees. Plus: Rob explains how he’s been infusing AI into all aspects of running his business.

This week, in Episode 244, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It was right on,” she tells us. “I mean, it was totally, absolutely true.” We even brought ChatGPT into our conversation in real time, asking it whether Jaci had hired the right business development person, whether Sarah had been fully prepared two years ago to buy back her PR firm, and what’s the best podcast for small business owners. Plus: while we were talking, Jaci asked ChatGPT to evaluate the performance of her co-founder and spouse, MIchael. Let’s just say, it does have some concerns.

This week, Gene Marks highlights some recent tech developments, including: Quickbooks is selling a lifetime version of its software for just $250. Microsoft has reintroduced its somewhat controversial Recall AI tool, which captures and indexes screenshots of user activity every three seconds—a function that is intended to improve cybersecurity but that has raised some interesting questions. Plus: Gene explains how—if you have the time and money—you can now connect the various software platforms you use and turn them into a smart AI assistant.