Latest podcast episodes
Episode 154: ‘What Doesn’t Keep Me Up at Night?’
‘What Doesn’t Keep Me Up at Night?’
TIME TO LISTEN: 51:51

This week, we did something different. We recorded this session in Chicago at our very first 21 Hats in-person event. In May, some 20 impressive entrepreneurs from around the country, from different industries, with businesses of different sizes and stages, gathered to talk shop for three days. The last thing we did was to record this episode in which we gave the participants the opportunity to ask the podcast regulars anything they wanted. Those regulars included Jay Goltz, Sarah Segal, and Dana White, and the questions addressed everything from hiring to motivating to delegating to pricing to coping with stress to what they wished they’d figured out sooner and to what still keeps them up at night. And when there were no more questions, I asked those who attended the Chicago event what I could have done to make it better. That I would invite criticism in a conversation being recorded for a podcast audience, took some of the participants by surprise. But, as you’ll hear, it worked out pretty much the way I hoped.

Is PR Worth the Effort?
TIME TO LISTEN: 46:05

This week, William Vanderbloemen says good public relations is absolutely worth the time and money. Paul Downs says PR hasn’t worked for him. At this point, he says, there are all kinds of ways he’d rather spend his time and money. Meanwhile, Sarah Segal, who owns a PR firm, offers some tips on how to approach and how to employ a firm effectively. Along the way, we discuss what’s expensive when it comes to PR and whether owners can just do it themselves. Plus: Paul explains how he dug himself out of a sales hole by not doing anything differently. And we find out how the owners feel about all of the new ways they’re being asked to leave tips.

Marketing Workshop: I Didn’t Know It Was Going to Work
TIME TO LISTEN: 53:16

This week, Shawn Busse and Loren Feldman talk to John Garrett about his contrarian approach to newspapers, marketing, and competition. Garrett has built a Texas-based chain of print newspapers that has managed to outcompete established news organizations and digital platforms for both community engagement and local advertising. Not surprisingly, when he first took out a $39,000 credit card loan in 2005 and started telling people that his business model would feature a monthly print publication that he would mail to everyone in his target communities for free, he didn’t get a lot of congratulations. And not everything he’s tried has worked. An expansion into Arizona, Tennessee, and Georgia, for example, failed early in the pandemic. But almost 20 years after its debut, a period during which most local publications have been in retreat, Community Impact is thriving. And from his seat as a publisher, Garrett offers a perspective on marketing that any business owner would be wise to consider.

I’m Not a Real CEO
TIME TO LISTEN: 44:24

This week, Jay Goltz, Liz Picarazzi, and Sarah Segal talk about the inherent conflicts between being an entrepreneur and being a CEO—and the different skill-sets each role requires. Does it make sense for the same person to do both jobs? Is being CEO even a full-time job? And when does it make sense to replace yourself as CEO? Liz says she’s thought about it. Jay, not so much: “Could I have found somebody 10, 15, 20 years ago who was a better manager? Sure. But it just wasn't worth it.” Why not? “It's gonna cost you $250,000 a year,” Jay says. “Is it worth paying that?” Plus: Liz and Sarah talk about positioning a company to be acquired. And Sarah proposes a PR campaign for Liz’s package bins right on the spot.

Bonus Episode: Not Sold on ESOPs? There’s a New Alternative
TIME TO LISTEN: 50:23

This week, two special guests who have built highly successful companies talk about what they ultimately plan to do with those companies. Ari Weinzweig is co-founder of Zingerman’s Community of Businesses, a collection of mostly food-related companies that are an iconic part of Ann Arbor, Michigan. Brad Herrmann is co-founder of Text-Em-All, a software firm based near Dallas that helps organizations deliver personalized, informational, and emergency messages by text and by phone. Both Zingerman’s and Text-Em-All consider themselves purpose-driven. Both practice open-book management. And so, not surprisingly, the founders of both companies took a hard look at selling to an employee stock ownership plan, or ESOP, in the hope that the cultures they’ve created might live on. But both companies, independently, soured on the notion of creating an ESOP, one after spending more than $200,000 and coming within a week of closing the deal. And now, both have settled on a little known alternative, what’s called a perpetual purpose trust. So far, only a handful of companies have tried to create a purpose trust for this purpose, but Zingerman’s and Text-Em-All are taking the leap. As both Ari and Brad acknowledge, they’re kind of figuring it out as they go.

Never miss a 21 Hats Podcast episode
When CEOs Behave Badly
TIME TO LISTEN: 41:39

This week, our conversation starts with Shawn Busse and Jay Goltz trying to understand why CEOs keep going viral for their misguided attempts to rally the troops. Shawn suspects CEO screeds have always existed—they just haven’t been recorded. He also thinks they tend to come more from public company CEOs who are beholden to shareholders. Jay thinks they’re just morons. “I really don't understand how someone could be smart enough to run a big company like that,” he says, “and be so completely ignorant. It's shocking to me.” Of course, CEOs of both publicly owned companies and privately owned companies do have to do unpleasant things sometimes, but Shawn and Jay say they’ve learned from their own experiences handling layoffs and recessions. “Do we have to go out of our way to be callous about it?” Jay asks. “I don't think so.” Plus: the very different ways Shawn and Jay manage their hiring processes. Oh, and, what would happen if Jay applied for a job at Shawn’s business?

‘It’s Going to Take $8 Million in Financing’
TIME TO LISTEN: 48:00

This week, Stephanie Stuckey tells Paul Downs and Liz Picarazzi how she and her partners have taken their business from $2 million in annual revenue to more than $13 million in three years. What’s frustrating, she says, is that she could be selling a lot more pecan snacks and candies. But with production at capacity, she’s not doing much sales outreach until they can fully revamp their manufacturing operation, which will require a significant investment. “I spend my days doing financial paperwork,” Stephanie says. Plus: Liz explains why her business picks up when the weather warms up, and after a slow start, Paul gets a boost from a big manufacturer.

We’re Still Buying Inventory
TIME TO LISTEN: 37:01

This week, Jay Goltz tells William Vanderbloemen that even with an inventory glut, a cash crunch, and a weakening economy, he’s not going to stop buying goods for his home store: “It's kind of like cutting Samson's hair,” Jay tells us. “I don't want to mess with telling the buyer, ‘Stop buying stuff.’ Because that's the business we’re in.” All of which has Jay feeling some pressure, but he’s very glad he’s been maintaining a credit line equivalent to 10 percent of sales. Plus: William explains how hiring can go wrong even at a staffing company and how he managed to raise his prices without actually raising his prices.

Recession? That’s When You Need to Attack
TIME TO LISTEN: 50:43

This week, Paul Downs, Sarah Segal, and Laura Zander discuss how they think about the possibility of recession: Do they proceed with planned hires? Do they continue to spend on marketing? Do they look for unexpected opportunities? In addition, Sarah, having recently taken back ownership of her PR firm, asks Paul and Laura how they pay themselves, how much cash they keep on hand, and whether they think she should expand her offerings to include digital marketing. Plus: Laura, who’s acquired several businesses over the years, explains what she looks for, how she decides how much to pay, and why she’s come to see acquisitions as necessary for the survival of Jimmy Beans Wool. As usual, all three owners are remarkably generous about sharing their thinking and even their numbers.

I Just Cut My Pay
TIME TO LISTEN: 49:07

This week, Paul Downs tells Shawn Busse and Jay Goltz that his year has not gotten off to a great start. This was supposed to be the year that Paul unleashed a bold, new marketing campaign that would put his business on an entirely new trajectory—and perhaps it still will be. But for the moment, his revenue has fallen considerably short of his expectations, which has presented him with an unwelcome choice: Should he hold-off on the marketing campaign? Or should he cut his own salary? Along with discussing Paul’s decision, we also talk about the process of rethinking a website, how best to make use of LinkedIn—it’s a gold mine for both business development and recruiting, says Shawn—and why Paul and Shawn continue to perform their own HR chores.

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