

21 Hats Podcast
21 Hats
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
Mentioned books

Feb 8, 2022 • 53min
Have You Considered Not Taking Investors?
This week, in episode 95, Jay Goltz, Liz Picarazzi, and Dana White talk about the advantages and disadvantages of bringing in outside capital and expertise—something both Liz and Dana have considered. “I have a background in Russian literature and credit card marketing,” says Liz. “I'm now a manufacturer, so if I could have an outside investor who either brought that to the table or could help me with it, that would be really valuable.” But of course, there are trade-offs. We also talk about Dana’s looming franchise sales, why it’s so hard to hire lawyers and accountants, and whether there’s an opportunity for Jay in framing NFT art.

Feb 7, 2022 • 24min
Dashboard: A Tale of Two Cities (Fort Myers and Philadelphia)
This week, Loren Feldman and Gene Marks talk about whether a four-day work week is a benefit small businesses can use to lure employees. Plus: Is your website ADA compliant? And what do you do if you get a complaint that it’s not? And Gene talks about why he prefers Florida’s response to the pandemic to Philadelphia’s, which he says is killing the city’s restaurants. But are Philadelphia’s restaurants suffering because they can’t seat the unvaccinated? Or is it because they can’t keep their customers and employees healthy?

Feb 1, 2022 • 54min
The Game Has to End at Some Point
This week, in episode 94, Shawn Busse, Paul Downs, and Jay Goltz talk about their evolving succession plans. There are lots of options—selling the business, turning it over to a family member, selling it to an employee stock ownership plan, holding a going-out-of-business sale, just walking away—and they all come with advantages and disadvantages. Shawn, Paul, and Jay take us through their current thinking and also tell us whether their businesses are prepared for the possibility that they could be incapacitated. Plus: Would any of them consider instituting a four-day work week? And we can report that this podcast now has its first B Corp. Who knows what a B Corp is?

Jan 31, 2022 • 20min
Dashboard: Is Pay Transparency Good for Businesses?
This week, Loren Feldman talks to Lou Mosca, COO of American Management Services, about the growing trend of making salaries public—either because municipalities require it or because businesses choose it. Plus: if the economy is growing at its fastest pace in decades, why doesn’t it feel like it? And how should businesses plan? And a recent study found that more than half of the 2,000 workers surveyed had resignation letters already written. What does this suggest about The Great Resignation?

Jan 25, 2022 • 45min
The Hardest Thing I’ve Done in Business
This week, in episode 93, Jay Goltz, Liz Picarazzi, and William Vanderbloemen talk about sales, specifically the transition most founders have to make from handling sales themselves to building a sales team. Jay, Liz, and William also discuss the value of going to trade shows, the pros and cons of compensating salespeople based on commission, and the differences between inside sales and outside sales. “The kind of person,” Jay says, “who can go out there and cold call all day long and get the door slammed in their face—it's very hard to find, very hard to keep, very hard to train, very hard to control. And that’s been my biggest challenge in business, without any doubt.”

Jan 24, 2022 • 16min
Dashboard: The State of Small Businesses
This week, Loren Feldman talks to John Arensmeyer, founder and CEO of Small Business Majority, about what most concerns the businesses in his group and how they view their prospects. Plus: what are smaller businesses doing now that the Supreme Court has blocked the vax-or-test mandate? Is there a possibility of more funds being allocated to the Restaurant Revitalization Fund? And what are the chances of legislation passing that would curb anti-competitive practices on Big Tech platforms? And is it really the case that these proposals have bipartisan support?

Jan 21, 2022 • 1h 4min
Bonus Episode: The Changing Face of the Yarn Industry
For many, knitting may still conjure an image of a grandmother in a rocking chair, her cats sleeping and her doilies taking shape. In recent years, however, the quiet industry of tiny neighborhood yarn shops scattered across the U.S. has become an unlikely cultural battleground. It’s been divided by charges of racism and cultural appropriation that have erupted in a series of social media firestorms, prompting some owners to close, sell, or rebrand their businesses. It may seem surprising that such a quiet pursuit could produce so much conflict, but it’s really not all that different from the fissures afflicting the country as a whole. In this bonus episode of the 21 Hats Podcast, we meet three women who were not content to stick to their knitting: Adella Colvin, whose business, LolaBean Yarn Co., is a prominent independent dyer based in Grovetown, Ga.; Gaye (a.k.a. GG) Glasspie, a leading yarn industry influencer whose signature color is orange and who is based in Clifton, New Jersey; and Felicia Eve, who owns String Thing Studio in Brooklyn, N.Y., which is one of the few Black-owned yarn shops in the country.

Jan 18, 2022 • 44min
I Want to Double Sales This Year
This week, in episode 92, we introduce another new member of the 21 Hats Podcast team, Liz Picarazzi, who talks Shawn Busse and Paul Downs through a series of challenges she’s faced at her business, Citibin. Among those challenges: why she outsourced her manufacturing to China, why she’s trying to bring it back, why she’s struggling to find an American fabricator that wants her business, why she thinks she wasted all of the money she spent last year on digital marketing, how she managed to double sales anyway, and where she found the right person to handle the aspects of running Citibin that she doesn’t think she’s good at.

Jan 17, 2022 • 19min
Dashboard: Is There Anything That Can't Be Sold?
This week, Loren Feldman and Gene Marks talk about how Hormel is somehow selling more Spam than ever. Plus: What will small businesses do now that there’s no vax-and-test mandate? Why Buy Now Pay Later is a good deal for small retailers (but potentially risky for their customers). And why you shouldn’t use your customer relations platform for email marketing—even though CRM providers say you can.

Jan 11, 2022 • 44min
Maybe It’s Not the Marketing
This week, in episode 91, we introduce a new member of the 21 Hats Podcast team, Shawn Busse, who tells Jay Goltz and Laura Zander about an intriguing challenge he faces. Twenty-two years ago, Shawn co-founded a marketing firm called Kinesis, but now he’s trying to convince clients that it takes more than just marketing. Sometimes, it’s not enough just to drive more leads. Sometimes, you have to step back and take a deeper look at your business, which not every client is ready to do. In fact, it took Shawn 10 years (and the Great Recession) to do it with his own business.