

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 15, 2022 • 23min
Dashboard: What the Inflation Reduction Act Means for Businesses
This week, John Arensmeyer, founder and CEO of Small Business Majority, an advocacy group for entrepreneurs and businesses, talks about what businesses can expect from the legislation coming out of Washington, D.C.—not just the climate, tax, and health care bill, but also the CHIPS and Science Act. In many instances, the benefits to business owners will come indirectly, he says, but they will come nonetheless.

Aug 9, 2022 • 48min
Trash, Rats, and Garbage Juice: A Case Study in PR
This week, in episode 119, Liz Picarazzi tells Jay Goltz and Sarah Segal about her first brush with bad publicity. Liz’s debacle started with a negative post that appeared in a prominent local blog. It was about a Times Square pilot program for which her business, Citibin, is supplying trash bins. The problem? The bins were not being maintained properly, and there were photos to prove it. At the time we recorded this conversation, Liz was bracing for additional stories in both the New York Post and The New York Times. Both of those stories have since been published—we’ll talk about them in a coming episode—and you can find links to all of the coverage in the show notes. For Liz, perhaps the biggest challenge was defending her company without trashing her client.Show Notes:Here’s the Streetsblog post: https://nyc.streetsblog.org/2022/07/20/gross-clean-curbs-bins-show-growing-pains-in-times-square/Here’s the New York Post story: https://nypost.com/2022/07/30/nyc-citibins-leaking-garbage-left-open-in-times-square/And here’s The New York Times story: https://www.nytimes.com/2022/08/06/nyregion/new-york-city-garbage-containers.html

Aug 8, 2022 • 29min
Dashboard: Why Gene Marks Hates Employees, Part 492
This week, Gene talks about how he recently had a mild case of COVID but worked right through it, no problem, which got him to wondering why employees—in his view—do not seem to be similarly dedicated. In fact, Gene believes that employees are using “COVID hysteria” as a pretext to avoid work and catch up on their TV watching. Plus, Gene explains why he thinks Wawa, a chain of convenience stores, is a good model for his own business. And he tries to make sense of a recessionary economy that produced more than half a million jobs in July.

Aug 2, 2022 • 43min
“I Think I’m Screwed”
This week, in episode 118, Jay Goltz tells Shawn Busse and Karen Clark Cole about a dream he had recently. It was a dream, of all things, about this very podcast, and on it, someone—it was a guy—was talking about how his business was faring: “I think I’m screwed,” he says in Jay’s dream. But who was it? And why was he screwed? Jay woke up before those answers were revealed. So we did some interpreting on this week’s real podcast. Spoiler alert: It wasn’t that hard to interpret! Plus: Shawn explains why he thinks his website is no longer performing. Karen explains why she thinks it’s actually easier to onboard an employee who will work remotely. And Jay and Karen discuss whether it’s time to give up on things going back to the way they were.

Aug 1, 2022 • 20min
Dashboard: Welcome to the Pre-Recession!
This week, Gene Marks and Loren Feldman try to make sense of where the economy is headed and what it means for business owners. Plus, Gene explains why he thinks some business owners may be fooling themselves about whether their business is growing. He also talks about a CRM tool that Google is giving away for free, as well as what you need to know to start a business.

Jul 26, 2022 • 48min
Are There Enough Hours in Your Day?
This week, in episode 117, Paul Downs, Sarah Segal, and Laura Zander discuss their daily routines, how those routines have been affected by the pandemic, whether they think they’re working too much or too little, and whether they would join a peer group where they would be exposed to owners who are working harder and, perhaps, having greater success. Plus: Laura places her bet on influencer marketing, Paul says his new marketing campaign has already paid off, and Sarah explains why none of her employees have ever asked her for a raise.

Jul 25, 2022 • 24min
Dashboard: "I Killed"
This week, Gene Marks reports back from a conference of funeral directors and debunks a silly survey that predicts a bleak future for small businesses. Plus: How the rules defining full-time employees and contractors could be changing, why some business owners are giving up on their CRM systems too soon, and how a relatively new law can help businesses save money administering retirement plans.

Jul 19, 2022 • 44min
Employees Still Have the Leverage
This week, in episode 116, Jay Goltz, Liz Picarazzi, and William Vanderbloemen discuss how their businesses are holding up and whether they’ve gotten past the labor shortage (short answer: No). The conversation veers into a discussion of how to finance growth and what to do when your bank is unresponsive (find another one!). And then Liz explains her intense distaste for dealing with lawyers, accountants, and insurance agents and how she’s trying to cope with it. “Believe me,” responds Jay, “I haven't paid enough attention to certain things that I should have, and it's cost me. But yeah, we can't every day just do the inspiring, cool, fun, oh-my-God, we-had-a-big-sale, look-at-the-problem-I-solved thing. It’s all part of the package.”

Jul 18, 2022 • 26min
Dashboard: Something Is Going to Happen
Dashboard: Something Is Going to HappenThis week, Mel Gravely, CEO of Triversity Construction in Cincinnati, joins Dashboard to explain why—even though he has an extremely healthy backlog of work lined up for 2023—he’s more than a little concerned about where the economy is headed. He also talks about how the labor shortage in his industry started well before The Great Resignation and why he doesn’t see it ending any time soon. And then there’s the challenge of bidding for future contracts without knowing what your materials or labor are likely to cost. Plus: He talks about what he’s learned in the year since he published his book, “Dear White Friend,” in which he sought to start an honest conversation with other business owners about race.

Jul 12, 2022 • 43min
How Would You Spend $10,000 a Month on Marketing?
This week, in episode 115, Shawn Busse, Hans Schrei, and Sarah Segal explain what they would do if I gave them $10,000 a month to spend on marketing. As we all know, there’s a lot going on right now. No one’s entirely certain where the economy is headed, and no one’s entirely certain where digital marketing is headed. So it seemed like a good time to ask our regulars where they would place their bets if we offered them each an imaginary pot of money to promote their brands. Spoiler alert: Their responses gave us a good sense of what these business owners think is working right now—and it’s definitely not billboards.


