21 Hats Podcast

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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.

Recent Episodes
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Recent Reviews
  • Glassbusinessguy
    Excellent for update to date information
    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.
  • Texas Kurt
    Great resource for entrepreneurs
    This podcast and the 21 Hats newsletter is a welcome resource to help entrepreneurs and SMB owners to be successful!
  • Green day fan 17
    A must listen for small business owners
    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.
  • Tricia37
    Informative and Empowering
    This specific podcast gets me through housework. What I respect the most is the panel's willingness to take on hard issues and difficult questions. They do so with mutual respect, so differences of opinions are helpful rather than negative. They have fun too, so it's entertaining and the time passes quickly. I have some of the quotes from the podcast hanging on my fridge and they help me be a better leader.
  • David Mammano
    Perfect timing
    Loren and his fab five are just what I needed. Perfect for what I’m going through! Kind of like “The View” for entrepreneurs...
  • BorgoBear
    Listen to this!
    This is a great podcast. You should listen regularly to get the full effect.
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