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 <b><a href="http://21hats.com/" target="_blank" rel="noreferrer noopener">21hats.com</a></b> to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.

21 Hats Podcast
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Podcast Overview
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 <b><a href="http://21hats.com/" target="_blank" rel="noreferrer noopener">21hats.com</a></b> to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.
Language
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Publishing Since
1/7/2020
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Recent Episodes

June 19, 2026
Dashboard: A Compensation Plan Becomes an Exit Plan
Host Jerry D. Johnson interviews Julia Beardwood, founder of Beardwood, about how her compensation strategy evolved into a successful exit plan for her branding agency.

June 16, 2026
Maybe EOS Will Solve Our Problem
In this interview, Laura Zander, Paul Downs, and Shawn Busse explore the real-world effectiveness and limitations of the Entrepreneurial Operating System (EOS) for business owners.

June 12, 2026
Dashboard: Helping Creatives with the Business of Art
Host Dale Partridge interviews Kim Robinson, founder of 3pts, about empowering artists to master the business of their creative careers.
543 total episodes available with 240 transcripts
Recent guests on 21 Hats Podcast
Guests from recent episodes — sign up to see every guest that has ever appeared on this show.
Julia Beardwood
Guest
Shawn Busse
Guest
Paul Downs
Guest
Laura Zander
Guest
Kim Robinson
Guest
Sarah Segal
Guest
Jaci Russo
Guest
Lena McGuire
Guest
Sean Joy
Guest
Ted Wolf
Guest
Channon Kennedy
Guest
Bryan Clayton
Guest
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Frequently asked questions
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- What is 21 Hats Podcast?
- How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 9 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Yes, this podcast regularly features guests.
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