

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

Sep 19, 2023 • 43min
I Would Have Been a Sub of a Sub of a Sub
This week, in episode 168, Shawn Busse, Paul Downs, and Liz Picarazzi talk about when it makes sense to walk away from a client. Liz, for example, is tired of dealing with bureaucracy and being at the bottom of the food chain. In one instance, she was so turned off that she actually recommended a competitor for a job she no longer wanted. Paul has a simple test: If it’s easy work for a bad client, okay, fine. But if it’s hard work for a bad client, “Just don’t do it.” Of course, there are times in the life cycle of most businesses when that’s easier said than done, when you have to accept almost any work offered. Those are the tough ones. Plus: Is it time for business owners to take artificial intelligence seriously? And should owners care that a well-known economics firm is predicting a depression in 2030?

Sep 18, 2023 • 21min
Dashboard: The Big Issues Looming for Small Businesses
John Arensmeyer explains what the end of pandemic-era childcare support will mean for businesses. He also talks about the Department of Labor’s proposed overtime rule and what’s at stake for business owners if the government shuts down. Plus: owners say banks are getting harder to deal with.

Sep 12, 2023 • 46min
The Temptation of Private Equity
This week, in episode 167, Shawn Busse, Jennifer Kerhin, and William Vanderbloemen discuss private equity. Both William and Jennifer have been getting emails and calls from representatives of PE firms who come promising all kinds of gifts—connections, expertise, money to invest in the business, and money to take off the table—which is why the temptation can be great. “If anybody even just offered me a three-day vacation, I think I would jump at it,” Jennifer jokes. But of course PE firms do exact a price, possibly including control of what used to be your business, which is why Jennifer says she wonders whether she should even take the phone calls. Entering the conversation, she says, feels a little like entering the Garden of Eden. Do you take a bite of that apple? Plus, Shawn thinks he’s found a better way to manage his company’s credit cards, and Jennifer gives us an update on her new website.

Sep 5, 2023 • 38min
Bonus Episode: When Private Equity Comes for Your Industry
This week, Dr. Randy Spencer talks about the changes that have been roiling the vet business. For one thing, that pandemic puppy boom we all heard about has brought additional stress to veterinary workers who had already had more than their share. For another, there’s been a wave of corporate money and private equity flowing into the industry. That sounds as if it could be a good thing. And in fact, Spencer says he’s been dodging a constant flow of acquisition inquiries for years. But the big money has also engendered considerable turnover and disruption, and in response, Spencer decided to sell 100 percent of his business, 1st Pet Veterinary Centers, to an employee stock ownership plan in 2021. The transition to an ESOP remains something of a work in progress, in part because veterinary people tend to be more focused on pets than they are on profits. “Veterinary medicine,” Spencer says, “is just the best profession in the world. In a way, it's a service industry, but we get to serve pets. That's why veterinarians get into it.”

Aug 29, 2023 • 41min
I Didn’t See All the Danger Signs
This week, in episode 166, Mel Gravely—the newest addition to our podcast team—tells Shawn Busse and William Vanderbloemen how he bought a Cincinnati construction business in 2005 even though the company wasn’t doing well, even though he knew nothing about construction, and even though the company had been shopped to everyone who did know construction. As you’ve probably guessed, things worked out just fine for Mel, who is now focused on putting a plan in place that’s designed to keep Triversity Construction in business for 100 years. That goal, Mel explains, can mean taking some counterintuitive steps, including not always maximizing profit and not planning to stay in the CEO job as long as he might have preferred. Plus: we learn why the construction industry is unlikely to be an early adopter when it comes to AI. And William tells us how he did this year on his mission to make himself less essential to his own business.SHOW NOTES:Here’s the podcast where William first introduced us to his concept of a “vomit list.” Here’s a profile Bo Burlingham wrote about Dave Whorton, the founder of the Tugboat Institute.Here are the principles behind Tugboat and the evergreen philosophy of business building.

Aug 22, 2023 • 51min
The Toughest Conversation
This week, in episode 165, Paul Downs, Jay Goltz, and Laura Zander don’t hold back. Laura and Jay both say their sales are coming in well below expectations. Not surprisingly, Jay has a five-point checklist that he’s using to assess and address his shortfall. Laura’s situation involves a marketing team that she says has been feeling stressed and is coming apart, with lots of crying and arguing. “They’re just collapsing,” she tells us. Paul, meanwhile, says his sales aren’t bad, but he’s got one employee who’s been holding them back. The employee, who’s been with Paul for 10 years, has been spiraling of late, says Paul, who’s dreading what he calls “the toughest conversation,” a conversation he fears will leave the employee devastated. In such situations, Jay says, he’s found it helpful to rank himself from one to 10 on the hardass scale: If Mr. Rogers is a 1 and Jack Welch—the take-no-prisoners former CEO of GE—is a 10, where do you want to be? “If you pick four or five,” Jay says, “you're probably gonna go out of business.”

Aug 21, 2023 • 19min
Dashboard: Why Business Owners Don’t Like This Economy
Gene Marks tells Loren Feldman that by almost any measure the economy continues to perform quite well. And yet, business owners don’t seem to believe it. Why is that? Gene says owners have some cause for concern. In fact, he expects a slight recession or slowdown in the next three to six months—of course he’s been saying that for more than a year now. “One of these days,” he says, “I’m going to be right.” Plus: Gene highlights two significant tax credits that most business owners don’t know about.

Aug 15, 2023 • 46min
When Business Owners Burn Out
This week, in episode 164, Shawn Busse and Jay Goltz discuss a recent Business Journal report that a lot of business owners are feeling burned out. Why is that, and what can owners do to avoid it? And have either Shawn or Jay been there? Plus: Shawn brings us up to date on the leadership transition he’s initiated, and—believe it or not—Jay has had another revelation about ESOPs. Also, do business owners need better regulation or no regulation? And which regulations are annoying Shawn and Jay the most right now? For Shawn, it’s the nightmare of having employees in multiple states and having to figure out and comply with the various rules of each of those states.Show Notes:You can learn more about Shawn Busse’s September event Catalyst.Here’s the Business Journal article about business owner burnout.Here’s the podcast where Phil Hayes offers a fresh perspective on what it takes to do an ESOP.Here’s the conversation where Jim Kalb talked about his own ESOP.Here’s the most recent Dashboard conversation where I talk about regulation with Gene Marks.

Aug 14, 2023 • 24min
Dashboard: The Big Story in Small Business
This week, Gene Marks and Loren Feldman agree that artificial intelligence is becoming the biggest story in small business, with Gene highlighting a slew of AI tools that business owners can put to use right now. Gene also issues a warning that owners who do not start paying attention are taking a much bigger risk than they may realize. Plus: Gene also talks about team-building platforms that can help owners engage their employees, especially those working some or all of the time from home.

Aug 8, 2023 • 45min
Can I Go Dig a Hole?
This week, in episode 163, Liz Picarazzi, Jennifer Kerhin, and Sarah Segal talk about whether they ever wish they could go back to their corporate lives. For Liz, there was a period during the early days of COVID. For Jennifer, it was when she made the transition from a consulting business to an employee business. These days, none of them can imagine going back—although Sarah did have a rough week recently when she lost two clients. “It's just the way of the world,” she tells us. “When businesses are looking to cut costs, it’s outside agencies that go first. But when it's two of your largest clients in the span of a week, it's like, ‘Really? Can I go dig a hole, put myself in it, and just stay there forever?’” What she’s actually doing, as we discuss, is figuring out some new ways to attract more clients. We also discuss whether everyone needs a business plan and whether the three owners ever wonder if someone else would do a better job running their businesses.