

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 13, 2022 • 47min
Quiet Quitting: Another Gift Brought to You by Corporate America
This week, in episode 123 and in light of reports that half of the U.S. workforce has “quietly quit” their jobs, Shawn Busse, Paul Downs, and William Vanderbloemen talk about the latest rage: Is quiet quitting something new? Is it just a media creation? Have Shawn, Paul, and William experienced it in their businesses? And who’s to blame? Plus, the three owners explain how they hire for engagement and how they’ve changed their hiring processes in response to the pandemic and the labor shortage. For example, Paul explains why, in this brave new world, he continues to flip conventional wisdom on its head: Instead of hiring slow and firing fast, he’s been hiring fast and firing slow. And he says it’s working.

Sep 12, 2022 • 23min
Dashboard: What Type of Entrepreneur Are You?
How much control do you need? How much risk can you handle? This week, Ami Kassar, a small business finance expert, recalls feeling inadequate when he saw other entrepreneurs raising lots of money and going for broke (and sometimes getting there). He began to realize that there are different entrepreneurial personality types, and he’s developed a survey that can help you understand your own entrepreneurial instincts. The founder of MultiFunding also discusses how willing banks are to lend right now, what businesses should do to prepare for a downturn, why it’s important to manage your EIDL loan carefully, and whether it ever makes sense to turn to an alternative lender.

Sep 6, 2022 • 46min
We Have a Meeting With Costco!
This week, in episode 122, Hans Schrei and Sarah Segal talk about what it takes to break into Costco. How do you get on their shelves? If you do get there, how do you make sure your product will fly off of those shelves? And if you succeed, will you have the financing you’ll need to ramp up production? Along the way, Sarah offers some tips on enlisting Costco influencers, and Hans explains the inner workings of Wunderkeks’ equity crowdfunding campaign, where you can invest as little as $150 and where the company hopes to raise $1 million. Plus: Sarah responds to a smart listener’s suggestion of how to avoid getting ghosted by potential clients after preparing elaborate and expensive proposals.Show notes:Here’s Wunderkeks’ investing pitch on Republic: https://republic.com/wunderkeks Here’s the episode where we introduced Hans and Wunderkeks: https://21hats.com/wunderkeks-has-two-daddies/ And here’s the episode where Sarah talked about being ghosted by potential clients: https://21hats.com/trash-rats-and-garbage-juice-a-case-study-in-pr/

Aug 30, 2022 • 50min
Replay: You Take a Stand
This week, in part because Loren’s on vacation, we’re offering a replay of an episode we recorded more than two years ago. It was one of our early episodes, and it was recorded shortly after George Floyd was murdered. In the episode, Karen Clark Cole, William Vanderbloemen, and Dana White talked about how they viewed their responsibilities as business leaders at such a fraught moment. What, if anything, were they saying to their customers? What were they saying to their employees? It started as a conversation, but Dana took the lead quickly and powerfully. She talked about what it’s been like to so often be the lone Black voice in the room. She talked about what it’s like for African-American employees to come to work and wonder where their company and their colleagues stand. She drew a line in the sand. “Why is it hard,” she asked? “You’re either over here, or you’re over there.” Even if you’ve already heard this episode, we recommend listening again—especially given that business leaders are again being asked where they stand on social and political issues, whether it’s about race or abortion or the climate or democracy. If you haven’t already heard the episode, we doubt you will soon forget it.

Aug 23, 2022 • 49min
Here’s My New Succession Plan: I Can’t Die
This week, in episode 121, Shawn Busse, Jay Goltz, and Liz Picarazzi discuss their succession options and—if they could go back in time—what advice they would give their early-stage selves. Liz would tell herself to get some help with administrative tasks, Shawn would tell himself to find a mentor (although he’s not sure he would have listened to the advice), and Jay would tell himself that there’s an obvious solution to the chaos caused by fast growth. Plus: How Liz changed the narrative after Citibin’s bout with bad publicity. And we have suggestions for a listener who asks: How do you know when it’s time to quit the day job?

Aug 22, 2022 • 23min
Dashboard: The Tax Break No One’s Talking About
This week, Gene Marks and Loren Feldman talk about the rise of “quiet quitting,” the new term for when employees contribute the bare minimum. They also discuss the phenomenon of bosses who come into the office to set a good example even as their employees phone it in from the beach. But most importantly, Gene points out what few others have noted, which is that the Inflation Reduction Act extends a huge tax break for business owners that was nearing expiration. And that’s just one of many aspects of the bill that Gene applauds. So would he have voted for the bill? You might be surprised.

Aug 16, 2022 • 49min
Surviving Bad Clients and Bad Partners
This week, in episode 120, Shawn Busse and Paul Downs talk about what they’ve learned from their worst client experiences. Shawn, for example, tells us that he’s come to think about taking on a client much the way he thinks about hiring an employee. And Paul stresses the importance of watching what he says about difficult clients to his employees, because he doesn’t want to encourage a cynical attitude. From bad clients, our conversation shifts to bad partnerships. Even though their own partnerships ended poorly, both Shawn and Paul emphasize that having a partner can be invaluable in getting a business off the ground. In fact, Paul says he might even consider taking on a partner again. Plus, both Shawn and Paul explain why all the talk of recession is not giving them second thoughts about their ambitious marketing plans.

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.