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

This week, in episode 75, 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.

'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, in episode 74, 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.

Get Rid of the Arsonists

This week, in episode 73, 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?

It’s a Pile of Money

This week, in episode 72, 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.

I Had Two Great Candidates. They Both Blew Up.

This week, in episode 71, 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.

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Oh, No! They Accepted Our Offer

This week, in episode 70, 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.’”

'I Didn’t Look Like Them, But I Could Act Like Them'

This week, in episode 69, 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.

Does It Matter What You Name Your Business?

When Dana White chose a name for her business, she decided she wanted a name that had meaning—both for her and for the women she hoped to reach. When Laura Zander picked a name for her business, she thought she was going to be selling coffee. And when Jay Goltz chose a name for his business, he very strategically chose the perfect name to rank well in—wait for it—the Yellow Pages. This week, in episode 68, Dana, Laura, and Jay talk about what they consider the most important decisions they made in building their businesses—including why Dana closed her most profitable location, why it took Laura 15 years to find an operations person, and what Jay figured out about employees who struggle to grow with the business.

Why Did Your Business Succeed?

This week, in episode 67, we talk about how much of success is making the right decisions. How much is being in the right place at the right time? And how much is just luck? “I think that's the thing nobody wants to talk about,” Paul Downs tells us, “because it implies that there's a lot to success that is out of the control of the entrepreneur, and we're much more attracted as human beings to stories of people who have agency and are like, ‘Oh, there's a problem. I did this, and I won.’ That's what we like to hear.” So yeah, there’s always luck involved. But there are always forks in the road, and someone has to decide which way to go. This week we hear how a few of those key decisions played out.

The Constant Struggle of Digital Marketing

This week, in episode 66, we take another crack at some questions that don’t have definitive answers: Should business owners outsource their marketing or bring it in house? Either way, how do you know you’re picking the right agency or the right person? Is it possible to get someone great for what smaller businesses can afford to pay? Paul Downs tells us what happened when he hired a firm to audit his website. Dana White tells us why she dumped the agency she’d retained for $50,000. And Jay Goltz sums it up: When it comes to the mechanics of marketing, he says, “We’re all in the dark.” Plus: Dana gives a franchising update and Jay starts his own business group.

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