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
Mar 8, 2022 • 49min
We Tried That Brand Thing. It Didn't Work.
This week, in episode 99, Shawn Busse, Paul Downs, and Jay Goltz talk about the tendency of many businesses to obsess about their logo, their website, and the need to drive more leads. To which Shawn suggests concentrating first on customer experience. And Jay agrees: “It's better business,” he says, “to make your customers happier than to keep trying to find new customers.” But Paul has his doubts: “You can have your internal house in order, as I do,” he says. “And you can have a great website, as I do. But it's not driving new business to us at the moment.” Plus: Shawn, Paul, and Jay react to recently publicized strategies to address the labor shortage, such as giving out raises more than once a year and encouraging new employees to take a vacation before they start work.
Mar 1, 2022 • 44min
Somebody’s Hiring All of These People
This week, in episode 98, Jay Goltz tells Liz Picarazzi and Laura Zander that he’s had a revelation about The Great Resignation. Yes, he’s lost some people, but not necessarily his best people. “It shook the tree out,” he says, which is why he thinks businesses should be careful right now about hiring too quickly. Meanwhile, Liz talks about her latest product, a bear-proof trash enclosure, and why introducing it has been challenging. And Laura tells us what happened with the salesman she tried to send around the country in a souped-up van. Plus: Is this a great time or a terrible time to be in business?
Feb 22, 2022 • 1h 5min
We Don’t Have a Brand
This week, in episode 97, Paul Downs talks about why furniture makers traditionally have not stamped their names prominently on their work—and why he’s rethinking that now. That change of heart is the direct result of Paul’s unlikely experience connecting two very different businesses: One a Mennonite company manned by master craftsmen, and the other a startup manned by tattooed hipsters with a mastery of Kickstarter. Not only has the resulting culture clash changed the way Paul thinks about his own business, it’s also the subject of a book he’s writing. In this conversation, Paul explains what he’s up to and also talks about how close his business came to failing, how he plans to double his revenue, why he’s thinking about trying TikTok, and how he feels about his son’s success in the alternative reality of venture-backed startups.
Feb 15, 2022 • 45min
Why Not Become the Strategic Buyer?
This week, in episode 96, Shawn Busse, Karen Clark Cole, and Jay Goltz compare notes on some of the many choices they’ve made building their businesses, such as the emphasis they’ve placed on growth, the risks they see in growing through acquisition, and—as Karen has recently experienced—the rewards of being acquired. They also discuss whether The Great Resignation, despite forcing companies to pay higher wages and work harder to find and keep talent, just might be a good thing for business owners. As Shawn says, “This puts more people into the marketplace looking for businesses where culture matters, where the owner has compassion and empathy, where families are valued, just on and on and on. And if you're that employer, you win.”
Feb 14, 2022 • 21min
Dashboard: Is the Labor Shortage Easing?
This week, Loren Feldman and Gene Marks talk about why he thinks inflation is pulling workers back into the workforce. Plus: Is it a big deal that Apple is going to let businesses take payment by iPhone? And Gene explains just how easy it can be to steal money from a company’s bank account—and what you can do to protect your business.
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.”
