Latest podcast episodes
Episode 127: Dana Opens in Dallas
Dana Opens in Dallas

This week, Dana White tells Paul Downs and Jay Goltz how her move to Dallas is going, including hiring a manager, firing a publicist, tweaking her business model, and for the first time, confronting competition. Dana also explains the surprising way she managed to get the financing to open her first salon on a military base, Ft. Bragg, which she now thinks could be up and running by the end of the year. Plus: Paul has to make adjustments to handle a sudden influx of business. And Jay is still looking for a head of HR. Should he post the ad on ZipRecruiter or Indeed? Should he offer a salary range in the ad? And is it reasonable for him to expect a follow-up email after an interview?

Bonus Episode: Seth Goldman Brews Another Ice Tea

This week, in a special bonus episode recorded right before Labor Day, Seth Goldman talks about getting the disappointing news that Honest Tea, the brand he built and sold to Coca Cola, was being discontinued—and how it took him about two weeks to decide to create another tea business to fill the shelf space that Coke was vacating. Along the way, Goldman talks about why it made sense to sell a mission-driven business to a soda company, what he wishes he had done differently in the sale, what it was like being a Coke employee, what he’s been doing since leaving, how the beverage industry has evolved, and whether he’ll end up selling this business to Coke, too.

Are You Hitting Your Numbers?

This week, Karen Clark Cole, Jay Goltz, and Sarah Segal discuss whether their businesses are meeting expectations and how that’s affecting their plans for next year. They also talk about how to handle an employee who doesn’t deliver, whether now is a good time to hire, and—in answer to a listener question—how to make the transition from using contractors to hiring employees. And Karen explains why employee utilization—that is, what percentage of her people are actually billing clients—is the most important metric she tracks and one she tracks on an hourly basis. Plus: Notebooks or Notion? All three owners tell us how they try to stay organized.

Raising Capital: It’s a Ticking Time Bomb

This week, Shawn Busse, Liz Picarazzi, and Hans Schrei debate the merits and risks of taking outside capital. Clearly, it makes sense for some businesses. But what are the right circumstances? What are the alternatives? And what do you need to understand before going to the dance? For example, what are the dynamics of the entrepreneur-investor relationship? Are the entrepreneurs hoping the investors will bestow an opportunity upon them? Or is it actually the entrepreneurs who have an opportunity to offer? And who pays for the coffee? Plus: What do you do on those days when no one seems to be following your lead and the entrepreneurial loneliness sets in?

Should HR Advocate for the Business or the Employee?

This week, Karen Clark Cole, Jay Goltz, and Sarah Segal talk about hiring an HR person. First, how do you handle HR issues before you can afford HR people? Is software the answer? At what size does a business need a full-time person? Do you hire someone who has experience but who might not be used to getting his or her hands dirty? Or do you hire someone you can mold to fit the culture of your business? Jay, who likes to say the entrepreneur is often the worst person to interview candidates, is currently interviewing candidates to be his head of HR, and he’s a little surprised at how few resumes he’s been getting. Plus: Sarah’s looking for office space and not finding much that would be acceptable. And how are Karen and Sarah doing now that, technically, they have been employees in their own businesses for a year?

Never miss a 21 Hats Podcast episode
Bonus Episode: Jason Fried Didn’t Mean to Blow Up Basecamp. But He’d Do It Again

This week, in a special bonus episode, Jason Fried talks about why things got crazy at software maker Basecamp and what it has meant for the business. As you may recall, in the spring of 2021, Fried, CEO and co-owner, issued a blog post edict eliminating a slew of benefits, shutting down a committee that had been attempting to address diversity issues, and barring discussion of all social or political issues on work forums. The email produced a backlash that culminated in a third of the company’s 60-some employees choosing to leave. The rupture was especially stunning coming at Basecamp, which has since re-branded by returning to its original name, 37signals, and which has long had a reputation for treating employees well, including offering remote work long before it was commonplace. When the story broke, some business owners applauded Fried for taking a stand. Others wondered how any policy that resulted in the departure of a third of a company’s employees could be worthy of praise.

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.

We Have a Meeting With Costco!

This week, 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.

You Take a Stand

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

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?

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