21 Hats Podcast
The 21 Hats Podcast is a weekly conversation with entrepreneurs who share their challenges and compare notes on how they’re coping with the pandemic, whether their businesses are as profitable as they should be, how big a price they are willing to pay for growth, and why they hired their brother-in-law. Every week, host Loren Feldman has a conversation with three of the show’s six regulars: Karen Clark Cole, CEO of Blink UX; Paul Downs, CEO of Paul Downs Cabinetmakers; Jay Goltz, CEO of The Goltz Group; William Vanderbloemen, CEO of Vanderbloemen Search Group; Dana White, CEO of Paralee Boyd; and Laura Zander, CEO of Jimmy Beans Wool. Every week, the owners talk about news stories that matter to business owners, and track what’s working and what’s not working on their own entrepreneurial journeys. Visit 21hats.com to read episode transcripts and learn more. The show is produced by Jess Thoubboron of Blank Word Productions.
Episodes
June 6, 2023 • 51 mins
This week, for episode 154, 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 regu...
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June 5, 2023 • 22 mins
This week, Ami Kassar tells Loren Feldman that in running MultiFunding, which helps businesses figure out their finance needs, he frequently meets business owners who know what they need to do but are reluctant to take that next step. One way to build your confidence, Ami says, is to make sure you really understand what drives your business model, which may require bringing in a fresh set of eyes, perhaps from a fractional CFO. Ami...
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May 30, 2023 • 84 mins
So, I decided to give the 21 Hats Podcast crew this week off. Between the Memorial Day holiday and our first 21 Hats in-person event the previous week in Chicago—attended by five of the podcast regulars—it seemed the right thing to do. It also seemed like a great opportunity to reprise one of our favorite all-time episodes. It’s not a used episode; it’s a certified pre-owned episode, or better yet, a greatest hits episode. We first...
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May 23, 2023 • 46 mins
This week, in episode 153, 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 wh...
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May 22, 2023 • 20 mins
This week, Gene Marks tells Loren Feldman that he thinks the ban signed by Montana's governor is a political stunt that could do real damage to businesses that have come to rely on the app. And yet, there seems to be momentum for similar bans in other states and even at the federal level. Plus: how to avoid ERTC fraud, why bankruptcies are skyrocketing, and should the business community be doing more to warn against risking default...
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May 16, 2023 • 53 mins
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 th...
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May 15, 2023 • 17 mins
This week, Gene Marks tells Loren Feldman that businesses should be making contingency plans in case there’s a default, especially if they rely on government contracts. Be careful how you spend and how you stash your cash. Plus: Gene gloats a bit about the end of the age of the worker (and then has some second thoughts). He also says reports of the death of the metaverse are greatly exaggerated and that it wouldn’t be so terrible i...
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May 9, 2023 • 44 mins
This week, in episode 152, 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...
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May 8, 2023 • 17 mins
This week, John Arensmeyer, CEO of the Small Business Majority advocacy group, and Loren Feldman talk about some of the most intractable problems confronting business owners. And John offers some reason for hope -- mostly, he says, because there’s a growing, bipartisan effort to level the playing field for smaller businesses. The debt ceiling, of course, is another matter.
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May 2, 2023 • 50 mins
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, informatio...
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May 1, 2023 • 26 mins
This week, Gene Marks takes Loren Feldman through a case study of how easy it is even for profitable businesses to get caught in a cash crunch. The problem, Gene explains, is that business owners often have to pay taxes on earnings that have yet to reach the owners. Where does the money go? To inventory, to capital expenditures, to accounts receivable among other places. How can owners avoid the crunch? By staying on top of their f...
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April 25, 2023 • 41 mins
This week, in episode 151, 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...
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April 24, 2023 • 21 mins
Yes, demand is tapering, and a recession is looming, Gene Marks tells Loren Feldman, but this is a great economy and a great country and people should stop complaining! Plus: Gene explains how some business owners get the state to pay for their employee training, how restaurants are finally adopting technology, and how to make sure your employees aren’t stealing from you. One tip: if you think an employee is stealing from you, send...
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April 18, 2023 • 48 mins
This week, in episode 150, 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...
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April 11, 2023 • 37 mins
This week, in episode 149, 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 main...
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April 10, 2023 • 25 mins
Gene Marks tells Loren Feldman he’s not seeing it yet, but there’s reason to believe it’s coming. Gene also discusses the best password managers for businesses and explains why addressing the mental health of employees is a financial issue as well as an ethical issue and offers some suggestions. Plus: he says he expects unlimited paid time off to remain a much-sought-after benefit for employees even though in many ways it favors em...
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April 4, 2023 • 50 mins
This week, in episode 148, 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 exp...
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April 3, 2023 • 21 mins
This week, Mel Gravely, CEO of Triversity Construction in Cincinnati, tells Loren Feldman why he still sees a recession looming—even though 2023 has been good so far, and he still has a solid backlog. He also talks about how he’s addressing the industry’s long-term labor issues, how Triversity lands new business, and what he’s doing to prepare for that recession.
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March 28, 2023 • 49 mins
This week, in episode 147, 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...
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March 27, 2023 • 21 mins
This week, Gene tells Loren Feldman why he hates the new Illinois law that requires businesses of any size to offer employees up to 5 days a year of paid time off — time that can be used for any purpose without explanation. Gene also suggests six things all owners should do if they have any thought of one day selling their businesses. And he explains his list of 10 tax-related numbers that he says every owner should know.
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