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
Aug 4, 2020 • 37min
Hair Is Segregated
In this conversation, Karen, Jay, and Dana discuss diversity in hiring and marketing. Dana talks about the challenge of getting white customers to come to a hair salon that is mostly Black. Karen talks about the challenge of persuading Black candidates to join a company that does not have a lot of Black employees: “So the question is not: are they out there? They're out there. I guarantee they're out there. The question is: do we need to spend more time, more energy, and be willing to be patient until we find a good pool of candidates?”
Jul 28, 2020 • 43min
My Jay Goltz Face
Paul Downs, Jay Goltz, and Dana White talk about how they would know if it was time to close their business, how long it takes to really grow up as a manager, what they’ve learned about managing—and occasionally firing—employees. “I think my staff hears me but eventually does what they want to do,” says Dana. “And that can be very draining because you wonder, ‘Well, why? I pay you. We’ve had training on it and talked about it.’” And Paul tells us that while he’s normally a pretty nice guy, he does have to put on his “Jay Goltz face” occasionally. “So what does that mean exactly?” asks Jay Goltz. “I’d like to understand.”
Jul 21, 2020 • 41min
I’m Not Going to Shut the Doors
This week, we introduced a new member of the podcast team, Paul Downs, whose company, Paul Downs Cabinetmakers, makes custom conference tables. Paul wrote about how close his company came to failing in both The New York Times’ You’re the Boss blog and in his own book, "Boss Life: Surviving My Own Small Business." That was during the Great Recession. Unfortunately, Paul is once again finding it challenging to sell high-end conference tables during a crisis. “My game plan is to stick it out,” he told us in this episode. “I’m not going to shut the doors. And two years from now, I may be a smaller company, but I'm going to be around, and then we're going to ride this back up.”
Jul 14, 2020 • 33min
Would You Start Your Business Today?
Jul 7, 2020 • 27min
Doomsday Fatigue
In last week’s episode, we asked our panel of business owners this question: Would you be doing anything differently with your business if you knew for sure that a second shutdown order was coming? It seemed like a pretty straightforward question, but it triggered one of our guests, Jay Goltz, who called it a “stupid” question and encouraged the other panelists not to answer it. So this week, we decided to try again to see if we could better understand how Jay is processing these stressful times. And to some extent, we succeeded, and we did get a little further beneath the surface—although there’s still a part of Jay that seems to be in denial. But maybe that’s just what it takes to be a successful entrepreneur. As Jay likes to say, “There's a thin line between visionary and delusional, and I've certainly been on both sides of that.”
Jun 30, 2020 • 24min
That’s a Stupid Question
As the numbers of new coronavirus cases explode across the country, Karen Clark Cole, Jay Goltz, and Laura Zander talk about how they are trying to make plans for their businesses. The conversation heats up a bit as it becomes clear that one of our owners (Hi, Jay!) isn’t quite ready to confront the possibility that he might have to deal with another shutdown. By contrast, Laura tells us, “We're operating as if there is a shutdown. So, yeah, we're operating the same way we were two months ago.”
Jun 23, 2020 • 36min
Do You Feel Shame Taking Money From the Government?
Jay Goltz, William Vanderbloemen, and Dana White—all of whom took Paycheck Protection Program loans—respond to an opinion piece that says “competent” business owners shouldn’t have had to go begging “shamelessly” for a government bailout, which got a particularly strong response from Jay: “I'm thinking of all of those entrepreneurs who are trying to run a business, trying to make happy customers—restaurants, hair salons trying to survive this whole thing, trying to take care of the emotional, the financial, and the physical needs… They're fighting a good fight, trying to stay in business so they can continue paying taxes, and he comes along and has to call us ‘shameless’ for taking money from the government.... Oh, we’re incompetent, because these people didn't have six months of savings stowed away?"
Jun 16, 2020 • 31min
I’ve Never Raised My Prices
Karen Clark Cole, Jay Goltz, and Dana White discuss their pricing strategies and why raising prices can be such a challenge: Dana tells us she has often wondered, “If I raise my prices, is this the decision that's going to make me close my doors?” And Jay recalls a customer who came into his picture framing shop and told a sales consultant, “Wow, that's a lot more than the other place I've gone to.” “Really, why don't you go there?” “Well, they're out of business.” And that, Jay tells us, helps explain why there are far fewer frame shops than there used to be.
Jun 9, 2020 • 52min
I’m Stressed
Karen Clark Cole, William Vanderbloemen, and especially Dana White have a painful, impassioned, uncomfortable conversation about trying to position their businesses and lead people in the aftermath of George Floyd’s murder and the ensuring protests. What do we tell customers? What do we tell employees? What do we tell black employees? Dana challenges us to take a stand—even if it’s uncomfortable—especially if it’s uncomfortable: “This is not about being comfortable. As business owners, you're either over there or you're over here.”
Jun 2, 2020 • 37min
How Do You Handle the Fact That a Lot of People Don't Like You?
This week we focused on Laura’s struggle to get control of a Texas-based yarn supplier that she acquired late last year. She’s had issues with inventory, personnel, quality control, and then the general manager walked out, which has Laura feeling deflated knowing that some employees are talking about her and some just don’t like her: “I really struggle with that. Am I the only one who struggles with stuff like that?” Plus: Laura and Jay talk about seizing the opportunity when a competitor goes out of business.
