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 12, 2022 • 42min
Do You Really Want That Shiny Object?
This week, in episode 104, Laura Zander tells Shawn Busse and Jay Goltz about her eight-month roller coaster ride pursuing an acquisition. The deal would bring a new brand and profitable revenue at a reasonable price. To Laura, the creative challenge and opportunity are exciting—“really, really exciting”—but the financials are a concern. “Do I do this?” she asks. “Is it worth it?” And then there’s the broker, whose numbers don’t add up and who wants to collect his fee—including his piece of the earnout—immediately. Plus: Shawn explains how the rise of inexpensive design contractors forced his company to become a better business.
Apr 5, 2022 • 48min
Do You Take Money off the Table?
This week, in episode 103, Shawn Busse, Paul Downs, and Jay Goltz discuss their philosophies about taking money off the table vs. reinvesting it in the business. Of course, you can’t take money off the table unless there’s money on the table. Paul tells us that he once calculated his average earnings for his first 22 years in business and they came to about $11 an hour. But he now expects to make more money in the next five years than he did in the previous 35. We also talk about content marketing, direct mail, and trade shows. Plus: Was the Paycheck Protection Program, despite the billions of dollars in fraud, a success?
Mar 29, 2022 • 40min
What If I Get the Contract?
This week, in episode 102, Liz Picarazzi tells Jay Goltz that she’s pursuing multiple sales opportunities—and ponders what would happen if those opportunities actually came to fruition. Would her company, Citibin, be able to handle the additional volume? “In my fantasy world, where I am a lot,” Liz says, “I look at where this could go. And just like you, Jay, I go to, ‘How in the world would I produce all of these?’” Liz and Jay also talk about the pros and cons of pricing transparency: Do you volunteer your premium price up front? On your website even? Or do you wait until you’ve made your sales pitch and gotten your customer excited? Plus: we indulge a little further discussion on the merits of the 21 Hats brand.
Mar 22, 2022 • 44min
Why I Sold 21 Hats
This week, in episode 101, the tables are turned, as Loren Feldman announces the sale of 21 Hats and takes questions from Shawn Busse, Karen Clark Cole, and Jay Goltz. The buyer is Toby Scammell, founder of Womply, which provides software services to small businesses and helped more than a million of them obtain Paycheck Protection Program loans. Loren will continue as editor-in-chief, but as he explains, much of what this will mean for 21 Hats has yet to be determined—including, for example, whether the new entity will keep the 21 Hats name. Shawn, Karen, and Jay share their thoughts on that and also talk about how Karen solves problems for her big tech clients—and what smaller businesses can learn from her process. And Jay explains a change he’s making to his 401(k) plan that he believes will make it fairer for all of his employees.
Mar 15, 2022 • 48min
We Are Survivors
This week, in episode 100, two years after the pandemic first hit, Shawn Busse, Jay Goltz, and Liz Picarazzi talk about what they’ve learned, what they’re doing differently, and whether their businesses have gotten weaker or stronger. Leading up to the pandemic, Shawn—still carrying scars from the Great Recession—did a series of workshops on how to prepare for the next recession. “And so in that regard,” he tells us, “we were really well prepared” for the pandemic. Plus: public companies are increasing prices aggressively and then bragging on earnings calls about the extra profits those increases are generating. Is there a lesson in this for privately-owned businesses? Also: why does Jay seem more invested in his picture frame business than in his home furnishings business?
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.
