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21 Hats Podcast

21 Hats Podcast

Auteur(s): 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 Gestion et leadership Marketing Marketing et ventes Politique Réussite personnelle Économie
Épisodes
  • Would a True Capitalist Consider a Worker Co-op?

    Would a True Capitalist Consider a Worker Co-op?
    Sep 9 2025
    A few months ago, John Abrams—author of From Founder to Future—joined us to talk about succession strategies and the different ways business owners can share ownership with employees. For his own business, John chose one of the more radical options: he turned his construction firm into a worker cooperative. Perhaps surprisingly, the more he described the co-op model, the more intrigued Jay Goltz became—although, predictably, Jay did retain a degree of skepticism. So we asked John to come back on the podcast to help Jay dig a little deeper: Are co-ops really all about democracy? Does someone on the loading dock get the same vote as the CEO? How do profits get split in the co-op model? How do losses get absorbed? How are loans secured without burdening frontline workers with personal guarantees? And perhaps most important: What can go wrong? In the end, I think surprising even himself, Jay failed to identify any real dealbreakers.

    Show Notes:

    Get a free trial of the Morning Report.

    Learn more about the Cooperative Fund of the Northeast.

    This is the podcast episode where Jay Goltz talks about how to do a We-SOP.
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    45 min
  • Dashboard: Are You Sure Your Business Can’t Be Sold?

    Dashboard: Are You Sure Your Business Can’t Be Sold?
    Sep 8 2025
    This week, Gene Marks makes a surprising claim: his business is “unsellable.” Never mind that it’s profitable. Never mind that it gave him the freedom to live the life he wanted and that it has left him and his wife financially secure for retirement. According to Gene, the business can’t be sold because it’s too dependent on him and because it has no IP, no exclusivity, and no moat. But is he right? Aren’t those the same challenges faced, for example, by countless HVAC and plumbing companies that private equity firms buy every day? Couldn’t Gene make his business sellable if he wanted to? What do you think? Is Gene leaving money on the table? Or has he just chosen the path that’s right for him and for his family?
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    30 min
  • Best of: A Punk Rocker’s Guide to Building a Business

    Best of: A Punk Rocker’s Guide to Building a Business
    Sep 2 2025
    In a few weeks, I’ll be in Portland, Oregon, for Shawn Busse’s always terrific Catalyst event. That trip has had me thinking about the city’s keep-it-weird ethos, the spirit that’s made Portland a hotbed for creative business building. My upcoming trip has also inspired me to revisit a podcast conversation Shawn and I recorded in early 2024 with Jenelle Etzel, who is founder of Living Room Realty. The boutique real estate agency has more than a hundred brokers and a reputation for doing things differently, but Jenelle didn’t set out to be a business owner. In fact, she majored in weaving (Shawn, for the record, majored in ceramics). She fronted a punk rock band. She lived out of a van. And yet, those experiences—especially learning how to manage people who didn’t technically have to listen to her and how to serve customers who’d been ignored by the mainstream—turned out to be perfect preparation for building a thriving business in a quirky city. It’s a story that says something about Portland, but even more about the unconventional paths that can lead to successful entrepreneurship.
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    57 min
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