419 Episodes

  1. Dashboard: A Fight for Survival

    Published: 4/7/2025

  2. ‘At 5 O’Clock, I’m Going to Send Everybody an Email’

    Published: 4/1/2025

  3. Dashboard: Smart People Are Hanging on to Their Cash

    Published: 3/31/2025

  4. Launching Lyx: ‘Gatorade for Dogs’

    Published: 3/28/2025

  5. I Wouldn’t Have Done This Without Covid

    Published: 3/25/2025

  6. Dashboard: Don’t Tell Me Your 2024 Financials Aren’t Ready

    Published: 3/24/2025

  7. I Think We’re in a Recession Now

    Published: 3/18/2025

  8. Dashboard: Will the Pain, Chaos, and Uncertainty Be Worth It?

    Published: 3/17/2025

  9. When There’s an Illness in the Family

    Published: 3/11/2025

  10. Dashboard: ‘We Can’t Keep Up’

    Published: 3/10/2025

  11. Our Government Is Doing This to Us

    Published: 3/4/2025

  12. Dashboard: What Does the Trump Chaos Mean for Small Businesses?

    Published: 3/3/2025

  13. I Am Comfortable Being Uncomfortable

    Published: 2/25/2025

  14. Dashboard: Is It Time to Abolish the SBA?

    Published: 2/24/2025

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

    Published: 2/18/2025

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

    Published: 2/17/2025

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

    Published: 2/11/2025

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

    Published: 2/10/2025

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

    Published: 2/4/2025

  20. Dashboard: A Warning for Small Businesses

    Published: 2/3/2025

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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.