21 Hats Podcast

A podcast by 21 Hats

Categories:

Business

405 Episodes

  1. We’re Not Failing Because We’re Idiots

    Published: 2/18/2025

  2. Dashboard: What If You Could Wave a Magic Wand?

    Published: 2/17/2025

  3. Everything Liz, Jaci, and Sarah Wanted to Know About Tax

    Published: 2/11/2025

  4. Dashboard: Gene Marks Has an Ambitious Plan to Do Less

    Published: 2/10/2025

  5. Most People Don’t Have the Stomach for This

    Published: 2/4/2025

  6. Dashboard: A Warning for Small Businesses

    Published: 2/3/2025

  7. The Tricky Business of Selling Small Businesses

    Published: 1/28/2025

  8. Dashboard: Is Small Business Optimism Eroding?

    Published: 1/27/2025

  9. I Think We’re Ready for the Tariffs

    Published: 1/21/2025

  10. Dashboard: How Do I Get ChatGPT to Notice Me?

    Published: 1/20/2025

  11. The Power of a Fresh Set of Eyes

    Published: 1/14/2025

  12. Dashboard: You Have to Make Your Own Weather

    Published: 1/13/2025

  13. We’re Not Saving Lives. We’re Saving Livelihoods

    Published: 1/10/2025

  14. I’m Looking at an Empty Pipeline

    Published: 1/7/2025

  15. Dashboard: Are Business Owners Too Optimistic About 2025?

    Published: 1/6/2025

  16. This Is What It Takes to Build a Business, Vol. 3, Part 2

    Published: 12/31/2024

  17. This Is What It Takes to Build a Business, Vol. 3, Part 1

    Published: 12/24/2024

  18. I’m Out of the Valley of Death

    Published: 12/17/2024

  19. Dashboard: Margins, Metrics, and Cash Flow

    Published: 12/16/2024

  20. It’s Not a Circuit-Board Business. It’s an Asset

    Published: 12/10/2024

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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.