Latest podcast episodes
Episode 77: Can an Entrepreneur Raise an Entrepreneur?
Can an Entrepreneur Raise an Entrepreneur?

This week, in episode 77, Jay Goltz and Diana Lee discuss the dangers of mixing entrepreneurship and parenting. Years ago, when Chris Rock was asked in an interview about his relationship with his children, he responded, “My kids are rich. I have nothing in common with them.” Obviously, that’s an extreme example, played for laughs by a comedian, but you don’t have to be a celebrity to wonder about the differences between your upbringing and your kids’ upbringing. As it happens, Jay and Diana were both raised in family businesses, but they offer contrasting approaches to the challenges of raising a family and building a business at the same time. Plus: we also talk about what the upheaval in the auto industry means for Diana, how to think about the president’s vaccine mandate, and whether Jay has resolved his crazy double-billing problem with AT&T.

Episode 76: Our Best New Accounts Are Coming Through LinkedIn

This week, in episode 76, Stephanie Stuckey talks about how she’s been winning her biggest retail accounts for Stuckey’s candies without a sales pitch. She also explains her latest manufacturing snafu, which she calls, “the case of the squishy pecan log rolls.” Laura Zander, meanwhile, tells us about the supply chain challenges she’s faced getting products from China, Vietnam, and South Africa. Plus, she talks us through how her latest price increases have resulted in a doubling of orders.

Dashboard: How Will the Vaccine Mandate Affect Smaller Businesses?

Every Monday, Loren Feldman and Gene Marks discuss the issues business owners should be monitoring. This week: the president’s vaccine mandate, the expanded EIDL, mitigating inflation, preventing ransomware attacks, and getting creativity from a remote workforce.

Episode 75: I Don’t Pay for Podcasts. Why Would I Pay for Yours?

This week, Karen Clark Cole, Paul Downs, and William Vanderbloemen start with a discussion of how 21 Hats might finally take the plunge into monetization. We also discuss Karen’s decision to forgo less-profitable revenue, William’s grand experiment of unplugging for seven weeks, and Paul’s attempt to balance personal and company responsibilities. Plus, we consider the impact of The Great Resignation, and we look for lessons to take from last week’s discussion about mental health.

Episode 74: 'Every Day, I Have to Force Myself to Get Out of Bed'

Because our core group of business owners has been talking to each other pretty much every week since before the pandemic, we’ve gotten to know each other. We’ve come to trust each other. And as a result, our conversations sometimes take unexpected turns. This week, our conversation takes an unexpectedly dark turn. We start out talking about Laura Zander’s efforts to manage personnel conflicts and Dana White’s visits to potential salon sites on military bases and Jay Goltz’s bizarre battle with his phone company, and we think we know what we’re talking about. But we keep talking until we realize that some of the issues we are discussing are more complicated and more painful than we’d understood, as is often the case with matters of mental health. You should know this conversation contains frank discussion of depression and suicide. For listeners, this may be surprising—not because anyone would think that entrepreneurs are immune to the afflictions that plague us all, but because there aren’t many public forums where people confront those afflictions openly and genuinely and in real time. For us, this conversation was a strong reminder that we often don’t really know what others are experiencing, whether they be friends, colleagues, or family.

Never miss a 21 Hats Podcast episode
Episode 73: Get Rid of the Arsonists

This week, we have a very special episode. It’s the dog days of August, and the only regular available was Jay Goltz. So we reached out to a bunch of loyal listeners who we happen to know have listened to every episode of this podcast, and we asked them if there was more they wanted to know about Jay—or if they’d heard enough. It turned out, they had some great questions, including: What he thought of Dana’s “Jay” Impression? What exactly he does all day (turns out, he’s not sure either)? How he learned to delegate? How he knows when it’s time to fire someone? And which of the other 21 Hats Podcast businesses he’d be inclined to invest in?

Episode 72: It’s a Pile of Money

This week, Paul Downs makes two seemingly contradictory points: One is that his business is on track to have its best year ever. The other is that he expects to claim another huge government subsidy, courtesy of the recently enhanced Employee Retention Tax Credit. As Paul says, if you don’t know about the ERTC or if you don’t know that its requirements have been relaxed, you probably should check it out. Meanwhile, Jay Goltz tells us what happened when three employees found out what the others were being paid, and Dana White feels a little deflated after talking to an investment banker. Plus: Paul shares his new strategy for coping with the labor shortage.

Episode 71: I Had Two Great Candidates. They Both Blew Up.

This week, we delve into some specific hiring situations, including Jay Goltz telling Diana Lee and Dana White that he thought he had two terrific candidates to replace his retiring chief financial officer. And then, after conversations with each of them, Jay had no candidates, which led us to some interesting questions: Has there been a more challenging time to hire for cultural fit? How risky is it for a smaller business to hire a candidate accustomed to working at larger businesses? And what does hiring intentionally for diversity mean when your staff is almost entirely African American? Plus: Dana gives us an update on her potential deal with the military and Diana explains how she markets her marketing agency.

Episode 70: Oh, No! They Accepted Our Offer

This week, Laura Zander, Diana Lee, and Dana White all share big news. Laura tells us that she and her husband/co-founder Doug put in a bid to buy a building for their business in Reno—and she’s not sure how she feels about the fact that their offer was accepted. Diana explains why she’s decided to pay a fortune to take over space vacated by glitzy magazine company Conde Nast in Manhattan’s Freedom Tower, a move that required her to put down a $2 million security deposit. And Dana tells us that she’s had preliminary conversations about opening Paralee Boyd salons on U.S. military bases around the world, which prompted Diana to encourage Dana to start vetting investment banking firms: “I'd be like, ‘Here's the contract with the Army. Give me the money so I can scale this out.’”

Episode 69: "I Didn’t Look Like Them, But I Could Act Like Them"

This week, we introduce a new regular on the 21 Hats Podcast team. Her name is Diana Lee, and she’s the founder of a digital marketing agency. In a conversation with Jay Goltz and Stephanie Stuckey, Diana explains how she got her business off the ground by helping car dealers target diverse communities within their markets, how she bootstrapped her business by convincing those car dealers to prepay 50-percent upfront, and how her first attempt at building a software platform ended with her spending $1 million on a platform that no one wanted to use.

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