# 21 Hats Podcast

Page: https://stenobird.com/podcast/21-hats-podcast-502638
Text version: https://stenobird.com/podcast/21-hats-podcast-502638.md
RSS feed: https://www.spreaker.com/show/4439758/episodes/feed
Official site: https://www.spreaker.com/show/21-hats-podcast
Author: 21 Hats
Episodes: 568

## Resource

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.

## Machine-readable

JSON: https://stenobird.com/v1/public/podcasts/21-hats-podcast-502638
Markdown: https://stenobird.com/podcast/21-hats-podcast-502638.md

## Episodes
- [Dashboard: Are You Still the Best Person to Run Your Business?](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-are-you-still-the-best-person-to-run-your-business) — 2026-09-18T09:00:58+00:00
- [You Just Lowered the Value of Your Business](https://stenobird.com/podcast/21-hats-podcast-502638/you-just-lowered-the-value-of-your-business) — 2026-09-15T09:01:11+00:00
- [Dashboard: He Sold the Business. The Regrets Came Later](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-he-sold-the-business-the-regrets-came-later) — 2026-09-11T09:01:18+00:00
- [She Thought She Was Building a Prospecting Tool for Herself](https://stenobird.com/podcast/21-hats-podcast-502638/she-thought-she-was-building-a-prospecting-tool-for-herself) — 2026-09-08T09:01:46+00:00
- [Dashboard: The Competitive Advantage AI Can’t Copy](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-the-competitive-advantage-ai-can-t-copy) — 2026-09-04T09:01:30+00:00
- [We’re Growing. Now I Want to Make Money](https://stenobird.com/podcast/21-hats-podcast-502638/we-re-growing-now-i-want-to-make-money) — 2026-09-01T09:01:26+00:00
- [Dashboard: Stop Asking How to Use AI](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-stop-asking-how-to-use-ai) — 2026-08-28T09:02:32+00:00
- [Best of: Selling My Business Nearly Broke Me](https://stenobird.com/podcast/21-hats-podcast-502638/best-of-selling-my-business-nearly-broke-me) — 2026-08-25T09:03:28+00:00
- [Dashboard: Is Staying Small Selfish?](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-is-staying-small-selfish) — 2026-08-21T09:06:29+00:00
- [With My New Rent, I Will Clear Nothing](https://stenobird.com/podcast/21-hats-podcast-502638/with-my-new-rent-i-will-clear-nothing) — 2026-08-18T09:09:20+00:00
- [Dashboard: It’s Not That Earnouts Are Bad. It’s That Bad Earnouts Are Bad](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-it-s-not-that-earnouts-are-bad-it-s-that-bad-earnouts-are-bad) — 2026-08-14T09:02:49+00:00
- [My Succession Plan Just Moved to Montana](https://stenobird.com/podcast/21-hats-podcast-502638/my-succession-plan-just-moved-to-montana) — 2026-08-11T09:05:17+00:00
- [Dashboard: The Problem with Retainers (and Other Lessons for Solopreneurs)](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-the-problem-with-retainers-and-other-lessons-for-solopreneurs) — 2026-08-07T09:01:45+00:00
- [You’re Pre-Qualified for a 13% Loan! (That Really Costs 170%)](https://stenobird.com/podcast/21-hats-podcast-502638/you-re-pre-qualified-for-a-13-loan-that-really-costs-170) — 2026-08-04T09:01:12+00:00
- [Dashboard: The ESOP Risk Nobody Talks About](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-the-esop-risk-nobody-talks-about) — 2026-07-31T09:00:15+00:00
- [‘I Want My Employees Building My Business, Not Theirs’](https://stenobird.com/podcast/21-hats-podcast-502638/i-want-my-employees-building-my-business-not-theirs) — 2026-07-28T09:00:32+00:00
- [Dashboard: Why Open Books and Employee Ownership Aren't Enough](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-why-open-books-and-employee-ownership-aren-t-enough) — 2026-07-24T09:00:40+00:00
- [Would You Rather Own a Business in the U.K. or the U.S.?](https://stenobird.com/podcast/21-hats-podcast-502638/where-the-grass-and-the-money-is-greener) — 2026-07-21T09:00:32+00:00
- [Dashboard: Why Do People Keep Starting Businesses?](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-why-do-people-keep-starting-businesses) — 2026-07-17T09:00:19+00:00
- [I’ll Deal with Succession Next Year](https://stenobird.com/podcast/21-hats-podcast-502638/i-ll-deal-with-succession-next-year) — 2026-07-14T09:00:23+00:00
- [Dashboard: You're Probably Not Spending Enough on AI](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-you-re-probably-not-spending-enough-on-ai) — 2026-07-10T09:00:20+00:00
- [What Do You Owe Your Employees?](https://stenobird.com/podcast/21-hats-podcast-502638/what-do-you-owe-your-employees) — 2026-07-07T09:00:28+00:00
- [Would Your Business Survive a Divorce?](https://stenobird.com/podcast/21-hats-podcast-502638/would-your-business-survive-a-divorce) — 2026-06-30T09:00:20+00:00
- [Dashboard: The Growth Strategy Hiding in Your Supply Chain](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-the-growth-strategy-hiding-in-your-supply-chain) — 2026-06-26T09:00:19+00:00
- [Why Do You Pay What You Pay?](https://stenobird.com/podcast/21-hats-podcast-502638/why-do-you-pay-what-you-pay) — 2026-06-23T09:00:16+00:00
- [Dashboard: A Compensation Plan Becomes an Exit Plan](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-a-compensation-plan-becomes-an-exit-plan) — 2026-06-19T09:00:16+00:00
- [Maybe EOS Will Solve Our Problem](https://stenobird.com/podcast/21-hats-podcast-502638/maybe-eos-will-solve-our-problem) — 2026-06-16T09:00:14+00:00
- [Dashboard: Helping Creatives with the Business of Art](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-helping-creatives-with-the-business-of-art) — 2026-06-12T09:00:15+00:00
- [Would You Rather Risk Losing a Client or an Employee?](https://stenobird.com/podcast/21-hats-podcast-502638/would-you-rather-risk-losing-a-client-or-an-employee) — 2026-06-09T09:00:23+00:00
- [Dashboard: A Buyer That Doesn’t Want to Flip Your Business](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-a-buyer-that-doesn-t-want-to-flip-your-business) — 2026-06-05T09:00:24+00:00
- [‘I’m Skeptical AI Is Going to Help Us’](https://stenobird.com/podcast/21-hats-podcast-502638/i-m-skeptical-ai-is-going-to-help-us) — 2026-06-02T09:00:20+00:00
- [Dashboard: Uber for Landscapers](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-uber-for-landscapers) — 2026-05-29T09:00:19+00:00
- [In Search of Companies More Interested in Being Great Than Big](https://stenobird.com/podcast/21-hats-podcast-502638/in-search-of-companies-more-interested-in-being-great-than-big) — 2026-05-26T09:00:19+00:00
- [Dashboard: Is It Still Worth Selling on Amazon?](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-is-it-still-worth-selling-on-amazon) — 2026-05-22T09:00:24+00:00
- [When Employee Violence Walks Through Your Door](https://stenobird.com/podcast/21-hats-podcast-502638/when-employee-violence-walks-through-your-door) — 2026-05-19T09:00:19+00:00
- [Dashboard: A Marketplace for Ethical Exits](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-a-marketplace-for-ethical-exits) — 2026-05-15T09:00:20+00:00
- [The Real Payoff May Be in Owning, Not Selling](https://stenobird.com/podcast/21-hats-podcast-502638/the-real-payoff-may-be-in-owning-not-selling) — 2026-05-12T09:00:19+00:00
- [Dashboard: Should You Pay $3,500 a Month for SEO?](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-should-you-pay-3-500-a-month-for-seo) — 2026-05-08T09:00:22+00:00
- [When That Big Break Just Might Break You](https://stenobird.com/podcast/21-hats-podcast-502638/when-that-big-break-just-might-break-you) — 2026-05-05T09:00:25+00:00
- [Dashboard: Bringing a Bazooka to a Wine Fight](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-bringing-a-bazooka-to-a-wine-fight) — 2026-05-01T09:00:20+00:00
- [There’s Scope Creep Around Every Corner](https://stenobird.com/podcast/21-hats-podcast-502638/there-s-scope-creep-around-every-corner) — 2026-04-28T09:00:20+00:00
- [Dashboard: Are We Overstating the Damage to Small Businesses?](https://stenobird.com/podcast/21-hats-podcast-502638/dashboard-are-we-overstating-the-damage-to-small-businesses) — 2026-04-24T09:00:28+00:00

## Actions

Episode pages expose an explicit `request_transcript` action. A page view does not automatically enqueue transcription.