Latest podcast episodes
Replay Episode 20: You Take a Stand
You Take a Stand
TIME TO LISTEN: 50:28

This week, in part because I’m on vacation, and in part because I’ve wanted to do this for some time, we’re offering a replay of an episode we recorded more than two years ago. It was one of our early sessions, and it was recorded shortly after George Floyd was murdered. In the episode, I asked Karen Clark Cole, William Vanderbloemen, and Dana White to talk 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 (including this one). 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.” More than a few listeners have told me that Dana’s words changed the way they view their responsibilities. Even if you’ve already heard this episode, I 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, I can assure you that you will not soon forget it.

Here’s My New Succession Plan: I Can’t Die
TIME TO LISTEN: 49:22

This week, 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?

Surviving Bad Clients and Bad Partners
TIME TO LISTEN: 48:53

This week, 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.

Trash, Rats, and Garbage Juice: A Case Study in PR
TIME TO LISTEN: 48:27

This week, 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.

“I Think I’m Screwed”
TIME TO LISTEN: 43:04

This week, 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.

Never miss a 21 Hats Podcast episode
Are There Enough Hours in Your Day?
TIME TO LISTEN: 47:37

This week, 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 other owners who might be working harder and 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 not one of her employees has ever asked her for a raise.

Employees Still Have the Leverage
TIME TO LISTEN: 44:04

This week, 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.”

How Would You Spend $10,000 a Month on Marketing?
TIME TO LISTEN: 43:00

This week, 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.

Wunderkeks Has Two Daddies
TIME TO LISTEN: 46:03

This week, we welcome another new panelist to the podcast, Hans Schrei, who is co-founder of Wunderkeks, an e-commerce bakery in Austin, Texas. Hans tells Jay Goltz and Liz Picarazzi why he and Luis Gramajo, his husband and co-founder, sold a business in Guatemala, immigrated here in 2019, and started a cookie business from scratch, going from selling at farmers’ markets their first year to doing more than $5 million in e-commerce last year. Hans also explains why he doesn’t think it’s enough just to make a delicious cookie, why he’s trying to raise seed capital, and what would happen to his visa if Wunderkeks were to fail.

Bonus Episode: Kurt Wilkin Hates Business Books. So He Wrote One
TIME TO LISTEN: 40:28

This week, in a special bonus episode, Kurt Wilkin talks about how he helped build several businesses, including most recently a recruiting business called HireBetter, and explains why he hates most business books. It has to do with the attention deficit issues he, like many entrepreneurs, tends to experience. So when he decided to write a business book of his own, he kept it short, and he structured it so that you can find the parts that are most relevant to you and skip the rest. It’s called “Who’s Your Mike?” and it features chapters on the kinds of hiring and management challenges all entrepreneurs confront, including situations involving employees like Mike. Who exactly is this guy Mike? Oh, you know. He’s the incredibly loyal and hard-working employee who’s been with you from day one but who isn’t necessarily growing with the business. Says Kurt, “We all have, or have had, or will have a Mike.”

We would love to hear from you
Ask us anything
Or suggest a topic for a podcast, an interview or a blog post