Episodes

  • Do I Want to Work with My Family?

    Do I Want to Work with My Family?
    Jul 15 2025
    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.
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    47 mins
  • Dashboard: Are We Getting Better at Teaching Entrepreneurship?

    Dashboard: Are We Getting Better at Teaching Entrepreneurship?
    Jul 14 2025
    This week, Frank Rimalovski, who is head of both the NYU Entrepreneurial Institute and the NYU Innovation Venture Fund discusses how his programs help young entrepreneurs build businesses — and why sometimes the most valuable lesson he can offer is to NOT start a business. He also talks about whether you can teach resilience, how he views the strengths and weaknesses of venture capital, and what the growing impact of artificial intelligence will be on programs like his.
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    38 mins
  • Straight Talk About ESOPs and Co-Ops and EOTs, Oh My!

    Straight Talk About ESOPs and Co-Ops and EOTs, Oh My!
    Jul 8 2025
    This week, in Episode 254, Jay Goltz, Mel Gravely, and special guest John Abrams have a frank conversation about what business owners can do to avoid what John calls the “fat-wallets-and-broken-hearts syndrome.” That’s his term for what can happen when an owner sells to private equity and the company ends up getting stripped. Jay, Mel, and John all agree they want no part of that. They all would like to see their businesses continue on without them. And yet, in thinking about succession, they’ve chosen different paths. In a conversation sparked by the recent publication of John’s book, From Founder to Future, we discuss those choices along with such issues as: why there are so few employee-owned businesses, whether they outperform other businesses, how you can finance the sale of a business to employees, whether the employee owners of an ESOP are truly owners, and whether a worker co-op model just might work for a hard-bitten, old-school owner like Jay Goltz.
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    50 mins
  • Dashboard: A Big Beautiful Win for Small Businesses?

    Dashboard: A Big Beautiful Win for Small Businesses?
    Jul 7 2025
    That’s what Gene Marks thinks. In this week’s conversation, Gene lists the tax changes in President Trump’s big beautiful bill that he’s happiest about, while emphasizing that what he’s really happiest about is the tax certainty that passage of the bill creates for business owners. Gene also explains why he thinks owners who complain about Trump’s tariffs have no one to blame but themselves and why he’s not all that concerned about the uncertainty the tariffs are generating, including what will happen this week when Trump’s Liberation Day pause expires.
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    43 mins
  • Something’s Happening in the Job Market

    Something’s Happening in the Job Market
    Jul 1 2025
    This week, in Episode 253, Paul Downs tells Kate Morgan and Liz PIcarazzi that he recently posted a job on Indeed and got 153 resumes—more than he’s ever gotten before, which prompted some interesting questions: What does this mean for business owners? Should a job posting be more about what the company expects from a candidate or more about what the company has to offer? Do the owners ask candidates to take personality tests? If the owners get 150 resumes, do they ask ChatGPT to review them? And doesn’t it seem as if more people are looking to switch careers? “When I look at someone who's working as a graphic designer in an ad agency,” Paul tells us, “I'm thinking: This person realizes AI is coming for their job.” Plus: Liz gives us a surprisingly upbeat update on her tariff situation. And the owners respond to a Reddit post asking whether it would be crazy to start a business in the current economic environment. Paul’s response: “Don’t do it.”
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    57 mins
  • Dashboard: Three Metrics for ‘White Knuckle’ Times

    Dashboard: Three Metrics for ‘White Knuckle’ Times
    Jun 30 2025
    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.
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    23 mins
  • Why Don’t You Just Sell the Business?

    Why Don’t You Just Sell the Business?
    Jun 24 2025
    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.
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    54 mins
  • Dashboard: Don’t Believe the AI Hype (Yet)

    Dashboard: Don’t Believe the AI Hype (Yet)
    Jun 23 2025
    This week, Gene Marks tells us why he’s skeptical of corporate CEOs like Amazon’s Andy Jassy who have started telling employees that they are likely to lose their jobs as the company continues to adopt tools that use artificial intelligence. Gene thinks CEOs who blame AI for corporate layoffs are really covering for bad management. In fact, he thinks anyone who is already replacing employees with AI is a fool. On the other hand, Gene tells us he’s incorporating AI tools into almost every aspect of his business, and he gives us some examples.
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    26 mins