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
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.
Jul 11, 2022 • 26min
Dashboard: Email or Text?
This week, Gene Marks and Loren Feldman talk about the continued rise of text message marketing and how it can be integrated with your CRM system. They also discuss why Gene warns businesses off of Twitter—even though he’s a power user. Plus: How do you plan for a recession and a labor shortage at the same time? And is that $10 billion in SSBCI money flowing yet?
Jul 5, 2022 • 40min
Bonus Episode: Kurt Wilkin Hates Business Books. So He Wrote One
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.”
Jun 28, 2022 • 46min
Wunderkeks Has Two Daddies
This week, in episode 114, 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.
Jun 27, 2022 • 21min
Dashboard: Keep Calm and Carry a Lot of Inventory!
Gene Marks, our man in London (at least for this week), tells Loren Feldman that small businesses in the UK are doing quite well, thank you! Marks and Feldman also discuss how your CRM system can help you fight inflation, the good news about bankruptcy laws, how to increase profits without raising prices, and whether it’s now okay to swear in the office. Cheers!
Jun 21, 2022 • 50min
Do Core Values Matter?
This week, in episode 113, Sarah Segal tells Shawn Busse and Paul Downs why she’s never articulated a set of core values for her business and why she’s thinking about doing it now. But she’s wondering whether establishing her values will really make a difference. Do employees care? Do clients care? Both Shawn and Paul say they do. In fact, Paul says his core values have been extremely helpful when it comes to recruiting. And Shawn says he thinks sharing values can be the best competitive advantage smaller businesses have. Plus: We get an update on how Paul’s big marketing initiative is going, and we follow up on why Sarah feels compelled to participate in almost all of her firm’s client calls.
Jun 20, 2022 • 25min
Dashboard: Gene Marks Would Rather Not Employ Gen Z
“I don’t have the time to deal with them because my resources are limited,” Gene Marks tells Loren Feldman this week. But he’s just fine hiring Millennials, and he explains why. Plus: The cheap money days may be over, but there’s a silver lining to that: Venture-backed businesses may actually have to operate like real businesses. And Chewy offers lessons in both customer service and social media.
