

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

Oct 24, 2023 • 42min
And Some Days the Bear Eats You
This week, in episode 172, Liz Picarazzi tells Jay Goltz and Sarah Segal that her trip to a bear sanctuary in Montana to get her trash enclosures certified as bear-resistant did not go precisely as planned. Because of a logistical snafu, she has not yet obtained either the certification or her real goal: a marketing video of the grizzlies attempting to crack open her baited enclosure. Fortunately, things went better for Liz in a more traditional marketing venue, a trade show in Chicago where she promoted her rat-resistant enclosures. Meanwhile, Sarah follows up on how things are going since losing two big clients and having to lay off three employees, and Jay explains his new catch phrase, “Let me not sleep on it.” Plus: we discuss the owner of a two-year-old construction business who wonders how long he should keep going if he doesn’t start to make a profit. He also asks why no one ever talks about how hard it is to run a business. While we can’t know for sure what’s happening inside his company, we can be pretty confident that he’s not listening to the right podcast.

Oct 23, 2023 • 21min
Dashboard: Gene Marks Expects an A.I. Backlash
For months, Gene has been telling us about all of the cool things we’ll be able to do with Microsoft’s Office 365 and Google’s Workspace when those companies integrate artificial intelligence into their platforms. Gene’s still excited about the possibilities, but he’s also more than a little annoyed, because both Microsoft and Google are planning to charge us quite a bit more for their A.I. enhancements. Gene also talks about automated invoicing, which he believes is going to displace a lot of employees, and why he believes most business owners are doing a poor job managing their insurance needs.

Oct 17, 2023 • 43min
We Haven’t Signed a New Client in Eight Months
This week, in episode 171, we meet Jaci Russo, the co-founder and CEO of BrandRusso and the latest addition to the 21 Hats Podcast team. Jaci tells Jay Goltz and Laura Zander how she went from working for Barry Diller to starting her marketing agency. Jaci also explains why she recently decided to introduce a four-day workweek and why she thinks her agency has now gone eight months and counting without signing up a new client—the longest such stretch in more than 20 years in business. “I find it interesting,” responds Jay. “You just said this is the first time you've ever had such a long period without new business. And, ‘Oh, we went to a four-day workweek.’ Hmm, how interesting.” Plus: Laura talks about what happened when venture-backed competitors came for the knitting industry and how stressful it is to buy and operate another business in another state.

Oct 16, 2023 • 22min
Dashboard: The Insane Burden of Health Insurance
This week, we learn that Gene Marks and Bernie Sanders agree on something, which is that there are better ways to handle health insurance than making business owners responsible for providing it to their employees. Isn’t running a business hard enough without this financial and bureaucratic burden? Does it really have to be this way? Plus: Why Gene thinks what he calls “the era of the worker” won’t last forever. And what business owners need to know and do before they lay off or fire employees.

Oct 13, 2023 • 23min
Bonus Episode: An Accidental Entrepreneur
It took a series of sad losses to turn banker Channon Kennedy into an entrepreneur. If a friend hadn’t lost his son and if Channon’s mother and sister hadn’t been diagnosed with cancer, she never would have designed, prototyped, manufactured, and started selling the Morgan Square, a tool that can save carpenters time while framing a project. CDhannon is just getting started, but we’ll keep in touch as her journey continues.

Oct 10, 2023 • 36min
Bonus Episode: The Employee Engagement Industry Has Failed
In this week’s bonus episode, Bill Fotsch, a business consultant, explains why he thinks much of the effort that he and many others have put into creating employee engagement over the past three decades has been wasted effort—well intentioned, but wasted. The fact is, Fotsch says, employees today are no more engaged than they were some 30 years ago when the concept of employee engagement first gained currency. So what’s the answer? Fotsch has come to the conclusion that it’s something he calls “economic engagement,” which happens to be the name of his consulting business. What exactly is economic engagement? He says it’s getting employees to focus on serving customers, and doing so profitably. He says it’s not so much about sharing financials with employees but about getting employees to understand the strategies and actions that really drive a business’s profitability. Fotsch is so convinced that he’s cracked the code that he’s gone beyond mere consulting and has been buying stakes in businesses so he can implement his ideas and prove his concept. So far, he says, it’s working.Show Notes:See how you score on an economic-engagement benchmark survey.Here’s Gallup’s G12 employee-engagement survey.Bill Fotsch co-authored an article that argues economic engagement is a logical successor to open book management.

Oct 3, 2023 • 43min
It’s Like Planning Your Own Funeral
This week, in episode 170, Jay Goltz tells Shawn Busse about the latest stop on his journey to figuring out whether an employee stock ownership plan is right for his business. Jay’s latest adventure includes waking up at 4:30 in the morning in Minneapolis too anxious to sleep—“Oh my God, what am I getting myself into here?”—and deciding to leave the seminar and drive back to Chicago. But on that six-hour return trip, Jay says his anxiety turned into clarity. In fact, he thinks he’s pretty sure he knows now what he wants to do. Of course, he has said that before. And we continue to learn more about ESOPs, this week hitting upon an interesting issue: ESOP enthusiasts love to tout the benefits of turning employees into owners. But are they really owners? And is that the right message to send them? “If you bought 10 shares of General Motors stock,” Jay asks, “would you tell your neighbors that you're an owner of General Motors?” Plus: We also talk about when business owners should ignore their accountants and whether Shawn and Jay expect their employees to come forward and tell them if they see another employee doing something they shouldn’t be doing.

Oct 2, 2023 • 19min
Dashboard: About That Shutdown
When Gene Marks and I recorded this episode of Dashboard on Friday, we were pretty sure the government was going to shut down. That, of course, didn’t happen so you can fast-forward through our brief remarks early in the show—or perhaps you would enjoy hearing Gene state confidently that he’s known all along that a shutdown was inevitable. We also discuss what Gene’s been hearing from business owners as he criss-crosses the country talking to various groups. And Gene talks about the IRS’s decision to suspend the ERC program and what you should do if you fear you may have been overly aggressive in your application. Plus, he explains why he hates LinkedIn but keeps using it anyway. -- Loren Feldman

Sep 26, 2023 • 40min
I’ve Never Had to Lay off Anyone Before
This week, in episode 169, Sarah Segal tells Shawn Busse that the other shoe has dropped. A couple of months ago, as she’s shared here previously, Sarah lost two big clients in one week. Now she takes us through her decision to lay off three of her employees, including what it means for the business and what it means for Sarah’s own role in the business. Before the layoffs, she had gotten to the point where she was working on the business—but now that’s changed. “I'm not working on the business,” she says. “I am working for clients. I am getting the job done. I am making sure that we're successful with our clients, and that is my priority right now.” Plus: We also discuss how to choose a CRM, why Sarah and Shawn’s home cities of San Francisco and Portland have been getting such bad PR, and whether former business owners are employable. “I wouldn’t hire me,” says Sarah.

Sep 25, 2023 • 18min
Dashboard: Do You Know What Your Margins Are?
This week, Tracy Bech talks about why it’s important, from time to time, to review your margins, to compare them with those of others in your industry, and to look for ways they might be improved. You might even find ways to adjust your business model. The first step, of course, is to make sure you know what those margins are. Plus: when is it time to start thinking about next year?