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 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.
Jun 14, 2022 • 49min
I Think You Need to Hire a PR Firm
This week, in episode 112, we welcome a new regular to the 21 Hats Podcast crew: Sarah Segal, founder and CEO of Segal Communications, a public relations firm based in San Francisco. First, Sarah tells Jay Goltz and Liz Picarazzi how she built her firm. Then, Jay and Liz ask Sarah all of their questions about public relations: How much outreach should they do themselves? Should they hire a PR specialist or a full-service agency? Should they approach journalists directly or through a publicist? And most important, how much should it all cost? Plus: Why Sarah’s still figuring out how to attract new business.
Jun 13, 2022 • 24min
Dashboard: Inflation, Recession, the Metaverse. Oh, My!
This week, Gene Marks and Loren Feldman talk about whether it’s time to panic about inflation and recession, how smaller businesses are managing their inventories through these unpredictable times, why businesses that take digital payments through a service like Venmo are going to have to be more careful, and what, if anything, the metaverse is likely to mean for the typical small business.
Jun 10, 2022 • 42min
Bonus Episode: I Didn’t Appreciate It Until I Almost Lost It
This week, in a special bonus episode, Greg Wittstock, founder of Aquascape, explains how he invented the backyard pond industry, how he improvised a business model, and how he almost lost it all. After failing at franchising, Wittstock decided to give away his pond building expertise and marketing to landscape contractors in what he calls “a franchise system without a franchise fee.” And it worked. Always candid to a fault, he recounts how the business shot to $59 million in annual sales, why it then stagnated for 10 years, and what he ultimately figured out about social media marketing. Plus: he also explains why his first rule of customer service is: Don't give them what they ask for. Give them what they want.Show Notes:Here’s Bo Burlingham’s profile of Greg Wittstock: https://www.inc.com/magazine/20031101/aquascape.htmlHere’s Greg’s video of Shaquille O’Neal’s pond installation: https://www.youtube.com/watch?v=Ti-k4LUQBNs
Jun 7, 2022 • 39min
Fire Your Franchise Consultant
As listeners to this podcast know, Dana White has a remarkable array of opportunities before her, including company-owned hair salons, franchised salons, salons on military bases, hair products, and POS software. But especially since the pandemic, she has struggled to get traction. This week, in episode 111, special guest Ami Kassar, an expert in small business finance, guides Dana through a discussion of how she might prioritize those opportunities and get them financed. Ami and Dana consider such questions as: What should she do first? Should she continue to pursue franchising, where she’s already sunk a lot of money? Or should she focus on opening company-owned salons at Fort Bragg and in Dallas? And should she be looking for an investor? If so, how important is it that she maintains control of the business? Or should she try for a bank loan? And if so, what kind of pitch is likely to impress a bank? As the conversation continues, a plan emerges.
