

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 11, 2022 • 50min
Dana Opens in Dallas
This week, in episode 127, 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?

Oct 10, 2022 • 28min
Dashboard: Welcome to Health Insurance Season!
This week, as many businesses find out what they’ll pay for health insurance next year, Gene Marks and Loren Feldman talk about how businesses can save money. Gene explains why self insurance has become more feasible for smaller businesses and why he thinks it makes sense to offer employees better health coverage instead of a pay increase. Also, it’s probably time to revisit your workplace drug policies. And Gene and Loren discuss why the concerns of small businesses often get overshadowed by those of big businesses.

Oct 7, 2022 • 35min
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, Just Ice Tea, 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.

Oct 4, 2022 • 41min
Are You Hitting Your Numbers?
This week, in episode 126, 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 an 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.

Oct 3, 2022 • 19min
Dashboard: I Like Recessions
This week, Loren Feldman speaks with Tracy Bech, who is CEO of Starboard Collectives and who specializes in helping business owners who don’t have a financial background (she understands: she was once one herself). Tracy talks about the two most important ratios for business owners to watch if they think we’re heading into a recession. And she also talks about why she actually likes recessions—or at least sees opportunities in them.

Sep 27, 2022 • 40min
Raising Capital: 'It’s a Ticking Time Bomb'
This week, in episode 124, 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?

Sep 26, 2022 • 23min
Dashboard: The (Commercial) Rent Is Too Damn High
This week, Gene Marks and Loren Feldman talk about what business owners can do to protect themselves in the current environment of rising rents and increased volatility. Plus: What explains the recent boom in startups? And will it last? And what the Fed’s rate hikes mean for businesses. Also: you can’t just set your website and forget it.

Sep 20, 2022 • 43min
Should HR Advocate for the Business or the Employee?
This week, in episode 124, 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?

Sep 19, 2022 • 23min
Dashboard: Could California’s Fast Food Regulations Actually Work?
Signed by Governor Newsom on Labor Day, California’s new fast food law creates committees, among other things, to set an industry-wide minimum wage. The plan sparked lots of outrage, but Gene Marks explains why he thinks it’s worth a try. He also notes that it could well be coming to a state near you. Plus: Gene also makes the business case for paid parental leave while also raising some interesting questions, including this one: If you offer paid leave to new parents, is that fair to employees who don’t have children? Gene also explains why he says buying Salesforce’s new small-business CRM is like ordering a salad at McDonald’s.

Sep 16, 2022 • 46min
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.Show notes:Here’s the blog post Jason Fried sent out announcing the policy changes: https://world.hey.com/jason/changes-at-basecamp-7f32afc5Here’s a story that recounted the backlash as it was happening: https://www.theverge.com/2021/5/3/22418208/basecamp-all-hands-meeting-employee-resignations-buyouts-implosionJason Fried is author or co-author of several books, including, “It Doesn’t Have to Be Crazy at Work.” https://basecamp.com/books/calm