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21 Hats Podcast

21 Hats Podcast

By: 21 Hats
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 The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they had to lay off employees, how they wound up with way too much inventory, why they don’t have a succession plan, and even why they are concerned about their own mental health. Visit 21hats.com to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.Copyright 21 Hats Economics Leadership Management & Leadership Marketing Marketing & Sales Politics & Government
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
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