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
Dec 14, 2021 • 41min
The Vomit List
This week, in episode 88, Jay Goltz and William Vanderbloemen talk about what it takes—in the throes of an unprecedented labor shortage—to hold on to your best people, the ones whose departures might send you looking for a trash can. They also discuss whether “hire slow” still works, whether it’s a good idea to rehire a former employee, whether it’s still possible to do a meaningful reference check, how to use 360 reviews and personality tests, and finally, whether Jay and William would be ready to sell their business if someone were to come along and offer them twice what they think it’s worth.
Dec 13, 2021 • 16min
Dashboard: A Tax Break Just for Business Owners
This week, Loren Feldman and Gene Marks talk about how some 20 states are giving business owners a special workaround that helps them evade the federal cap on state and local taxes. If you live in one of these states and have a pass-through corporate structure, it could be worth a lot of money. They also talk about reports that businesses are budgeting to give their employees big raises next year and why industrial space in some places is now worth more than office space. Plus: the latest Consumer Price Index inflation report is not looking very transitory.
Dec 7, 2021 • 44min
Are You Playing Offense or Defense?
This week, in episode 87, Paul Downs, Dana White, and Laura Zander talk about the lessons they’ll take from 2021 and what they’re hoping to accomplish in 2022. Paul thinks he’s found an alternative sales channel that will lessen his dependency on Google. Laura, who built Jimmy Beans Wool on ecommerce, is planning a renewed emphasis on brick-and-mortar retail. And Dana White is working on building the team that will help her pursue her remarkable opportunities with franchising and the military. Plus, we talk about how comfortable the owners feel showing up at work in a brand new car.
Dec 6, 2021 • 16min
Dashboard: Collect Your Own Data
This week, Loren Feldman and Gene Marks talk about how businesses that engage in digital marketing are adjusting to the new rules that make it harder to track customers. They also discuss how businesses are replacing employees with chatbots and what businesses should do while the vaccine mandate battle plays out in court. Plus: the SBA has $100 billion in disaster relief funds that are about to expire and it’s not too late to apply. What you need to know.
Nov 30, 2021 • 46min
When Buying an Unsexy Business Becomes Sexy
This week, in episode 86, instead of a conversation with our regulars, we talk to two people who walked away from promising careers to buy blue collar businesses. Long before search funds and sweaty startups became all the rage, Bob Schwartz left a Wall Street investment banking career to buy a chain of laundromats, SuperSuds, which operates in Delaware, Maryland, Pennsylvania, and Virginia. More recently, Mills Snell left a prominent private equity firm to buy a roofing contractor, Aqua Seal Manufacturing and Roofing, which is based in Columbia, South Carolina. In this conversation, Schwartz and Snell talk about what they were thinking, what they learned about buying a business, what they’ve learned about operating a business, and whether they’re looking for an exit.
Nov 16, 2021 • 44min
It’s Bonus Season. Are You Feeling Generous?
This week, in episode 85, Paul Downs, Jay Goltz, and Laura Zander talk about the bonuses they plan to pay this year—and how their bonus plans and philosophies have evolved over time: Are the payments a reward for company performance? Are they a reward for personal performance? Are they supposed to motivate? Or are they just a thank you? Then the owners talk management, a discussion inspired by last week’s episode with Dana White about navigating the space between being a pushover and being a jerk. Plus: Are 360 reviews good management or are they kind of creepy?
Nov 15, 2021 • 21min
Dashboard: Robots Aren’t Just for Big Boys Anymore
This week, Loren Feldman and Gene Marks talk about why robot sales are setting records and how even small businesses are taking advantage of the opportunity. They also talk about the inflation spike and why electric vehicles will help—at least over the long-term. Plus: the government takes action on ransomware, and a fresh approach to paid time off.
Nov 9, 2021 • 50min
“I Can Do It. I Promise You, I Can Do It”
This week, in episode 84, Dana White takes us along for the ride, sharing the remarkable opportunities and the daunting challenges she’s confronting simultaneously. In a one-on-one conversation, we catch Dana at an emotional moment. After a triumphant trip to Germany, where she expects to open salons on multiple military bases, she’s just returned to Detroit—only to learn that the team she’s counting on is showing serious cracks. Even as she’s signing contracts with the military, getting ready to roll out her franchising plan, and courting newfound investor interest in funding the development of her salon management software, those cracks have shaken Dana and left her questioning her approach as a CEO. Ultimately, she talks about those moments many entrepreneurs experience in the cold of night, when things aren’t going well, and they realize this is all on them. In those moments, Dana confesses, “I’m scared. And I feel alone.”
Nov 8, 2021 • 18min
Dashboard: A Social Media Strategy for Business Owners
This week, Loren Feldman and Gene Marks talk about an entrepreneur who may have cracked the code on TikTok by simply telling the story of her business the way she would tell it to a friend—although Gene’s not really buying it. They also talk about the Biden administration’s vaccine mandate now that the rules have been released, some options for businesses trying to figure out health insurance, and whether—as the Wall Street Journal reported—entrepreneurs really are happier than other people.
Nov 2, 2021 • 44min
Paying the Volcano God
This week, in episode 83, Paul Downs tells Jay Goltz and Laura Zander why he’s come to view Google as the Volcano God. He’s not sure what it will take to keep the Volcano God happy, but he’s obsessed with doing everything he can, because the consequences of failing would be so great. We also talk about Paul’s content marketing strategy, the pricing lessons that emerged from our recent attempt to monetize 21 Hats, and why Laura—even in the midst of the labor shortage—now has a waiting list of people hoping to work at her yarn manufacturer in Texas.
