

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

Apr 18, 2023 • 48min
‘It’s Going to Take $8 Million in Financing’
This week, in episode 150, Stephanie Stuckey tells Paul Downs and Liz Picarazzi how she and her partners have taken their business from $2 million in annual revenue to more than $13 million in three years. What’s frustrating, she says, is that she could be selling a lot more pecan snacks and candies. But with production at capacity, she’s not doing much sales outreach until they can fully revamp their manufacturing operation, which will require a significant investment. “I spend my days doing financial paperwork,” Stephanie says. Plus: Liz explains why her business picks up when the weather warms up, and after a slow start, Paul gets a boost from a big manufacturer.

Apr 11, 2023 • 37min
We’re Still Buying Inventory
This week, in episode 149, Jay Goltz tells William Vanderbloemen that even with an inventory glut, a cash crunch, and a weakening economy, he’s not going to stop buying goods for his home store: “It's kind of like cutting Samson's hair,” Jay tells us. “I don't want to mess with telling the buyer, ‘Stop buying stuff.’ Because that's the business we’re in.” All of which has Jay feeling some pressure, but he’s very glad he’s been maintaining a credit line equivalent to 10 percent of sales. Plus: William explains how hiring can go wrong even at a staffing company and how he managed to raise his prices without actually raising his prices.

Apr 10, 2023 • 26min
Dashboard: Is There Really a Credit Crunch?
Gene Marks tells Loren Feldman he’s not seeing it yet, but there’s reason to believe it’s coming. Gene also discusses the best password managers for businesses and explains why addressing the mental health of employees is a financial issue as well as an ethical issue and offers some suggestions. Plus: he says he expects unlimited paid time off to remain a much-sought-after benefit for employees even though in many ways it favors employers.

Apr 4, 2023 • 51min
Recession? That’s When You Need to Attack
This week, in episode 148, Paul Downs, Sarah Segal, and Laura Zander discuss how they think about the possibility of recession: Do they proceed with planned hires? Do they continue to spend on marketing? Do they look for unexpected opportunities? In addition, Sarah, having recently taken back ownership of her PR firm, asks Paul and Laura how they pay themselves, how much cash they keep on hand, and whether they think she should expand her offerings to include digital marketing. Plus: Laura, who’s acquired several businesses over the years, explains what she looks for, how she decides how much to pay, and why she’s come to see acquisitions as necessary for the survival of Jimmy Beans Wool. As usual, all three owners are remarkably generous about sharing their thinking and even their numbers.

Apr 3, 2023 • 22min
Dashboard: Winter Is (Still) Coming
This week, Mel Gravely, CEO of Triversity Construction in Cincinnati, tells Loren Feldman why he still sees a recession looming—even though 2023 has been good so far, and he still has a solid backlog. He also talks about how he’s addressing the industry’s long-term labor issues, how Triversity lands new business, and what he’s doing to prepare for that recession.

Mar 28, 2023 • 49min
I Just Cut My Pay
This week, in episode 147, Paul Downs tells Shawn Busse and Jay Goltz that his year has not gotten off to a great start. This was supposed to be the year that Paul unleashed a bold, new marketing campaign that would put his business on an entirely new trajectory—and perhaps it still will be. But for the moment, his revenue has fallen considerably short of his expectations, which has presented him with an unwelcome choice: Should he hold-off on the marketing campaign? Or should he cut his own salary? Along with discussing Paul’s decision, we also talk about the process of rethinking a website, how best to make use of LinkedIn—it’s a gold mine for both business development and recruiting, says Shawn—and why Paul and Shawn continue to perform their own HR chores.

Mar 27, 2023 • 22min
Dashboard: Gene Marks Is Not a Fan of Mandated PTO
This week, Gene tells Loren Feldman why he hates the new Illinois law that requires businesses of any size to offer employees up to 5 days a year of paid time off — time that can be used for any purpose without explanation. Gene also suggests six things all owners should do if they have any thought of one day selling their businesses. And he explains his list of 10 tax-related numbers that he says every owner should know.

Mar 21, 2023 • 36min
I Can’t Have a Handle on Everything
This week, in episode 146, Jay Goltz and Laura Zander talk about the limits of their own management. Once a business gets past a certain size, no owner can do everything or even be aware of everything. But where do you draw the line? Does the owner need to be conversant with most aspects of management, marketing, and finance to oversee the business? This came up, in part, because Jay told us recently that his framing shops routinely ask customers how they learned of the business and that a recent review indicated that his social media efforts were not having an impact. But when asked about those efforts, Jay wasn’t entirely sure what they consisted of or if they even existed. Perhaps surprisingly, it also became clear that Jay wasn’t all that interested in learning more. It was working well enough, he’d concluded, and that was all he needed to know. And that’s the starting point for today’s main conversation. Along the way, we also address such questions as: Where’s the line between being a manager and being a therapist? Do owners need to be passionate about their businesses? What does the phrase “people over profits” really mean? And while “the customer is always right” has become a cliche, is it really a good policy?

Mar 20, 2023 • 19min
Dashboard: Bank As I Say, Not As I Do
This week, in the aftermath of the Silicon Valley Bank collapse, Gene Marks says he banks at Wells Fargo — but that’s not what he recommends. His suggestion: Find a good community bank, spread your money around to play it safe, and then relax. He also says you should consider going to a four-day work week. And not because it’s good for your employees, but because it’s good for you.

Mar 14, 2023 • 47min
For Wunderkeks, It Really Is Go Big or Go Home
This week, in episode 145, Hans Schrei explains why he’s pursuing a deal with Costco and why his vision is to get Wunderkeks cookies into every supermarket in the country. When Jay Goltz counters that instead of thinking big, or thinking small, maybe Hans should think medium, Hans says that may no longer be possible with consumer packaged goods: “The little brand that grows and thrives by growing little by little doesn't really exist any more in this space,” he says. Underlying the discussion of how fast Hans wants Wunderkeks to grow and how quickly he wants to exit are the stress-related mental health issues that he’s discussed previously on the podcast and the fact that his partner, Luis, is in the U.S. on an entrepreneurial visa, which means that if the business were to fail, they might have to leave the country.