
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 ... more
| Publishes | Twice weekly | Episodes | 539 | Founded | 6 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | NewsBusiness NewsEntrepreneurshipBusiness | |||

Sean Joy is head of M&A at Chenmark, a Portland, Maine-based holding company that acquires a handful of small businesses each year. At first glance, Chenmark may sound like a traditional private equity firm, but it isn't. The company is family- and e... more
This week, we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom conference tables, says his business depends on somethin... more
When Bryan Clayton graduated from college, he discovered he had two options: take an entry-level job and a pay cut—or go back to mowing lawns, which was already making him more money. He chose the lawns. Over time, he built a commercial landscaping b... more
Twenty years ago, Bo Burlingham gave a name to a feeling a lot of business owners had struggled to articulate. In his book Small Giants, Bo profiled companies that had chosen not to chase growth at all costs. Most were bootstrapped, owner-operated bu... more
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I have listened to every single episode of 21 hats. This is my favorite business podcast as a small business owner. Real business owners sharing real wins and losses in real time. Must listen.
Started listening in 2024 and have enjoyed so many episodes. It's nice to finally have a business podcast with content that I can easily relate to and often apply to my business. I highly recommend trying 21 Hats.
I have been listening to this podcast for a couple of years now. Loren always has a wide array of great contributors. My favorite is Paul Downs.
This podcast and the 21 Hats newsletter is a welcome resource to help entrepreneurs and SMB owners to be successful!
Owning a small business can be lonely, so listening to other owners talk about their day-to-day is a pleasure. Loren expertly moderates a group of diverse (lots of women’s voices - thank you!) owners who are candid, approachable, and entertaining.
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Recent interactions between the hosts and their guests.
Listeners, social reach, demographics and more for this podcast.
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A practical, entrepreneur-focused show that features a rotating cast of small business owners who share real-world wins and challenges. Episodes typically cover profitability, hiring, leadership, operational systems, and practical strategies for growth, often with a candid emphasis on trade-offs, mental health, and personal resilience. Noteworthy is the mix of hands-on business advice, human-centric storytelling, and frequent discussion of real-world constraints like tariffs, hiring costs, and workforce management, making it valuable for listeners who want actionable insights from fellow owners and operators.
Rephonic provides a wide range of podcast stats for 21 Hats Podcast. We scanned the web and collated all of the information that we could find in our comprehensive podcast database. See how many people listen to 21 Hats Podcast and access YouTube viewership numbers, download stats, audience demographics, chart rankings, ratings, reviews and more.
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1. How I Built This with Guy Raz
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3. Organize 365 Podcast
4. Best of Both Worlds Podcast
5. WSJ What’s News
21 Hats Podcast launched 6 years ago and published 539 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Rephonic pulls ratings and reviews for 21 Hats Podcast from multiple sources, including Spotify, Apple Podcasts, Castbox, and Podcast Addict.
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Recent guests on 21 Hats Podcast include:
1. Jean Moncrieff
2. Eugene Khayman
3. Michelle Wyatt
4. Hannah Sandmeyer
5. David C. Barnett
6. Paul Downs
7. Shawn Busse
8. Liz Picarazzi
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