Episodes 541
Avg. Duration 38m
Activity Highly Active
Apple Rating 5.0 (34)
Since Jan 2020
Latest Episode Jun 2026

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Open to Sponsors Features Guests

Publishing Details

Schedule
Every Few Days
Format
Episodic
Consistency
80%
Hosting
www.spreaker.com

Contact & Outreach

About This Podcast

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.

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Recent Episodes

Dashboard: Helping Creatives with the Business of Art

Jun 12, 2026 37m

For years, Kim Robinson worked on the brand side, helping major companies connect with artists and creatives. Eventually, he decided he’d rather be working for the artists themselves. So he launched…

Would You Rather Risk Losing a Client or an Employee?

Jun 09, 2026 51m

This week, Sarah Segal, Jaci Russo, and Lena McGuire tackle a question many service business owners face: Which is the bigger risk—an employee who feels overburdened or a client who feels neglected?…

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

Jun 05, 2026 38m

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…

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

Jun 02, 2026 48m

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…

Dashboard: Uber for Landscapers

May 29, 2026 32m

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…

In Search of Companies More Interested in Being Great Than Big

May 26, 2026 50m

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…

Dashboard: Is It Still Worth Selling on Amazon?

May 22, 2026 30m

When Eugene Khayman first got involved with Million Dollar Sellers, it was essentially a support group for entrepreneurs building businesses on Amazon. Back then, the opportunity seemed almost…

When Employee Violence Walks Through Your Door

May 19, 2026 49m

Michelle Wyatt has replayed the events in her mind countless times, looking for warning signs she might have missed. But even now, she can’t find any. Both employees had passed background checks and…

Dashboard: A Marketplace for Ethical Exits

May 15, 2026 31m

Hannah Sandmeyer spent years acquiring ecommerce businesses for an Amazon aggregator, giving her a front-row seat to how deals get done—and what often gets lost in the process. Too many owners, she…

The Real Payoff May Be in Owning, Not Selling

May 12, 2026 48m

When Kate Morgan started thinking seriously about selling her business, she assumed the big payoff would come at closing. But as she tells David C. Barnett and Paul Downs this week, she’s come to…

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

May 08, 2026 26m

Most business owners know they need marketing. What many don’t know is what they should be paying for it—or what they should expect in return. So when an SEO agency proposes a $3,500-a-month plan,…

When That Big Break Just Might Break You

May 05, 2026 43m

Every business owner looks forward to that big break—the moment that you land a big client or a major retailer, or do something that puts you on a national stage. But those opportunities don’t just…

Dashboard: Bringing a Bazooka to a Wine Fight

May 01, 2026 50m

For years, the Wine School of Philadelphia and PhillyWine LLC coexisted in the genteel world of wine education. Then a trademark dispute turned that quiet coexistence into a legal battle—complete…

There’s Scope Creep Around Every Corner

Apr 28, 2026 48m

For Lena McGuire, scope creep really can show up around every corner. She’s in the home remodeling business. But for most owners, including Jaci Russo and Ted Wolf, projects that expand out of…

Dashboard: Are We Overstating the Damage to Small Businesses?

Apr 24, 2026 24m

Despite what we’ve been reading about tariffs and immigration and inflation and health insurance, the macro economy has actually held up better than many economists expected over the past year.…

Do Small Businesses Still Need HubSpot?

Apr 21, 2026 52m

Early on, William Vanderbloemen’s search firm was exactly the kind of business HubSpot, the marketing platform, was built to help. William had a highly specialized audience, his team produced content…

Dashboard: A Different Way to Buy Marketing

Apr 17, 2026 34m

Hiring a full-time marketing team isn’t realistic for a lot of small businesses—but doing nothing may not be an option either. This week, Johnathan Grzybowski explains how Penji, the platform he…

How Do You Sell HR to Owners Who Don’t Think They Need It?

Apr 14, 2026 45m

Sandy Kapell knows HR—just not the version most business owners live with. After years leading human resources for corporations, Sandy launched her own business, Trakehner Leadership, to bring that…

Dashboard: She Built a Business by Learning to Run Her Home

Apr 10, 2026 32m

In her thirties, Lisa Woodruff hit a breaking point—overwhelmed, overweight, and depressed, as she puts it. So she made a radical decision: she quit her job as a school teacher and set out to get her…

Are You Pricing for Your Clients or for Your Business?

Apr 07, 2026 54m

Pricing a service business sounds straightforward—until you actually have to do it. How much should you charge? What’s reasonable? And what happens when “reasonable” isn’t enough to keep the business…

Frequently Asked Questions

How many episodes does 21 Hats Podcast have?

21 Hats Podcast has published 541 episodes since January 2020, covering topics in Business, Business News.

Is 21 Hats Podcast still active?

21 Hats Podcast is currently highly active with new episodes every few days. Average episode length is 38m.

How do I contact 21 Hats Podcast for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for 21 Hats Podcast, including email and social media links.

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