Podcast

21 Hats Podcast

Author: 21 Hats
Feed episode count: 568
Official site: https://www.spreaker.com/show/21-hats-podcast
RSS: https://www.spreaker.com/show/4439758/episodes/feed
JSON: /v1/public/podcasts/21-hats-podcast-502638
Markdown: /podcast/21-hats-podcast-502638.md

Summary

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.

Episodes

Sep 18, 2026 · not_requested

Dashboard: Are You Still the Best Person to Run Your Business?

Duration seconds: 2030
Source: https://www.spreaker.com/episode/dashboard-are-you-still-the-best-person-to-run-your-business--75186727

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Sep 15, 2026 · not_requested

You Just Lowered the Value of Your Business

Duration seconds: 2924
Source: https://21hats.com/you-just-lowered-the-value-of-your-business/

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Sep 11, 2026 · not_requested

Dashboard: He Sold the Business. The Regrets Came Later

Duration seconds: 2321
Source: https://www.spreaker.com/episode/dashboard-he-sold-the-business-the-regrets-came-later--75049083

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Sep 8, 2026 · not_requested

She Thought She Was Building a Prospecting Tool for Herself

Duration seconds: 3184
Source: https://21hats.com/she-thought-she-was-building-a-prospecting-tool-for-herself/

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Sep 4, 2026 · not_requested

Dashboard: The Competitive Advantage AI Can’t Copy

Duration seconds: 1871
Source: https://www.spreaker.com/episode/dashboard-the-competitive-advantage-ai-can-t-copy--74867124

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Sep 1, 2026 · not_requested

We’re Growing. Now I Want to Make Money

Duration seconds: 3148
Source: https://21hats.com/were-growing-now-i-want-to-make-money/

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Aug 28, 2026 · not_requested

Dashboard: Stop Asking How to Use AI

Duration seconds: 2363
Source: https://www.spreaker.com/episode/dashboard-stop-asking-how-to-use-ai--74718269

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Aug 25, 2026 · not_requested

Best of: Selling My Business Nearly Broke Me

Duration seconds: 3021
Source: https://21hats.com/selling-my-business-nearly-broke-me/

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Aug 21, 2026 · not_requested

Dashboard: Is Staying Small Selfish?

Duration seconds: 2261
Source: https://www.spreaker.com/episode/dashboard-is-staying-small-selfish--74230079

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Aug 18, 2026 · not_requested

With My New Rent, I Will Clear Nothing

Duration seconds: 2623
Source: https://21hats.com/with-my-new-rent-i-will-clear-nothing/

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Aug 14, 2026 · not_requested

Dashboard: It’s Not That Earnouts Are Bad. It’s That Bad Earnouts Are Bad

Duration seconds: 2202
Source: https://www.spreaker.com/episode/dashboard-it-s-not-that-earnouts-are-bad-it-s-that-bad-earnouts-are-bad--73916496

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Aug 11, 2026 · not_requested

My Succession Plan Just Moved to Montana

Duration seconds: 2630
Source: https://21hats.com/my-succession-plan-just-moved-to-montana/

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Aug 7, 2026 · not_requested

Dashboard: The Problem with Retainers (and Other Lessons for Solopreneurs)

Duration seconds: 2031
Source: https://www.spreaker.com/episode/dashboard-the-problem-with-retainers-and-other-lessons-for-solopreneurs--73562674

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Aug 4, 2026 · not_requested

You’re Pre-Qualified for a 13% Loan! (That Really Costs 170%)

Duration seconds: 3029
Source: https://21hats.com/youre-pre-qualified-for-a-13-loan-that-really-costs-170/

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Jul 31, 2026 · not_requested

Dashboard: The ESOP Risk Nobody Talks About

Duration seconds: 2375
Source: https://www.spreaker.com/episode/dashboard-the-esop-risk-nobody-talks-about--73258620

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Jul 28, 2026 · not_requested

‘I Want My Employees Building My Business, Not Theirs’

Duration seconds: 3046
Source: https://21hats.com/i-want-my-employees-building-my-business-not-theirs/

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Jul 24, 2026 · not_requested

Dashboard: Why Open Books and Employee Ownership Aren't Enough

Duration seconds: 2185
Source: https://www.spreaker.com/episode/dashboard-why-open-books-and-employee-ownership-aren-t-enough--73126918

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Jul 21, 2026 · not_requested

Would You Rather Own a Business in the U.K. or the U.S.?

Duration seconds: 3590
Source: https://21hats.com/where-the-grass-and-the-money-is-greener/

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Jul 17, 2026 · not_requested

Dashboard: Why Do People Keep Starting Businesses?

Duration seconds: 1171
Source: https://www.spreaker.com/episode/dashboard-why-do-people-keep-starting-businesses--73014520

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Jul 14, 2026 · not_requested

I’ll Deal with Succession Next Year

Duration seconds: 3098
Source: https://21hats.com/ill-deal-with-succession-next-year/

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Jul 10, 2026 · not_requested

Dashboard: You're Probably Not Spending Enough on AI

Duration seconds: 1877
Source: https://www.spreaker.com/episode/dashboard-you-re-probably-not-spending-enough-on-ai--72889782

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Jul 7, 2026 · not_requested

What Do You Owe Your Employees?

Duration seconds: 3127
Source: https://21hats.com/what-do-you-owe-your-employees/

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Jun 30, 2026 · not_requested

Would Your Business Survive a Divorce?

Duration seconds: 3133
Source: https://21hats.com/would-your-business-survive-a-divorce/

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Jun 26, 2026 · not_requested

Dashboard: The Growth Strategy Hiding in Your Supply Chain

Duration seconds: 2367
Source: https://www.spreaker.com/episode/dashboard-the-growth-strategy-hiding-in-your-supply-chain--72694778

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Jun 23, 2026 · not_requested

Why Do You Pay What You Pay?

Duration seconds: 2883
Source: https://21hats.com/why-do-you-pay-what-you-pay-2/

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Jun 19, 2026 · not_requested

Dashboard: A Compensation Plan Becomes an Exit Plan

Duration seconds: 2364
Source: https://www.spreaker.com/episode/dashboard-a-compensation-plan-becomes-an-exit-plan--72564280

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Jun 16, 2026 · not_requested

Maybe EOS Will Solve Our Problem

Duration seconds: 3183
Source: https://21hats.com/maybe-eos-will-solve-our-problem/

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Jun 12, 2026 · not_requested

Dashboard: Helping Creatives with the Business of Art

Duration seconds: 2238
Source: https://www.spreaker.com/episode/dashboard-helping-creatives-with-the-business-of-art--72483460

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Jun 9, 2026 · not_requested

Would You Rather Risk Losing a Client or an Employee?

Duration seconds: 3060
Source: https://21hats.com/would-you-rather-risk-losing-a-client-or-an-employee/

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Jun 5, 2026 · not_requested

Dashboard: A Buyer That Doesn’t Want to Flip Your Business

Duration seconds: 2295
Source: https://www.spreaker.com/episode/dashboard-a-buyer-that-doesn-t-want-to-flip-your-business--72343826

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Jun 2, 2026 · not_requested

‘I’m Skeptical AI Is Going to Help Us’

Duration seconds: 2911
Source: https://21hats.com/im-skeptical-ai-is-going-to-help-us/

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May 29, 2026 · not_requested

Dashboard: Uber for Landscapers

Duration seconds: 1971
Source: https://www.spreaker.com/episode/dashboard-uber-for-landscapers--72185692

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May 26, 2026 · not_requested

In Search of Companies More Interested in Being Great Than Big

Duration seconds: 3016
Source: https://21hats.com/in-search-of-companies-more-interested-in-being-great-than-big/

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May 22, 2026 · not_requested

Dashboard: Is It Still Worth Selling on Amazon?

Duration seconds: 1835
Source: https://www.spreaker.com/episode/dashboard-is-it-still-worth-selling-on-amazon--72105075

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May 19, 2026 · not_requested

When Employee Violence Walks Through Your Door

Duration seconds: 2953
Source: https://21hats.com/when-employee-violence-walks-through-your-door/

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May 15, 2026 · not_requested

Dashboard: A Marketplace for Ethical Exits

Duration seconds: 1862
Source: https://www.spreaker.com/episode/dashboard-a-marketplace-for-ethical-exits--71990443

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May 12, 2026 · not_requested

The Real Payoff May Be in Owning, Not Selling

Duration seconds: 2911
Source: https://21hats.com/the-real-payoff-may-be-in-owning-not-selling/

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May 8, 2026 · not_requested

Dashboard: Should You Pay $3,500 a Month for SEO?

Duration seconds: 1590
Source: https://www.spreaker.com/episode/dashboard-should-you-pay-3-500-a-month-for-seo--71906305

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May 5, 2026 · not_requested

When That Big Break Just Might Break You

Duration seconds: 2590
Source: https://21hats.com/when-that-big-break-just-might-break-you/

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May 1, 2026 · not_requested

Dashboard: Bringing a Bazooka to a Wine Fight

Duration seconds: 3004
Source: https://www.spreaker.com/episode/dashboard-bringing-a-bazooka-to-a-wine-fight--71764949

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Apr 28, 2026 · not_requested

There’s Scope Creep Around Every Corner

Duration seconds: 2925
Source: https://21hats.com/theres-scope-creep-around-every-corner/

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Apr 24, 2026 · not_requested

Dashboard: Are We Overstating the Damage to Small Businesses?

Duration seconds: 1449
Source: https://www.spreaker.com/episode/dashboard-are-we-overstating-the-damage-to-small-businesses--71589808

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