21 Hats Podcast

By 21 HatsBusiness Entrepreneurship News Marketing Business News

21 Hats Podcast episodes

July 20, 2021 “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.
49 min
July 13, 2021 “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, 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.
41 min
July 06, 2021 Why Did Your Business Succeed?
This week, 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.
44 min
June 29, 2021 The Constant Struggle of Marketing
This week, 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.
43 min
June 22, 2021 This Is Where We Get Into Therapy
Once again this week, our business owners discuss things business owners don’t often talk about in public. Laura Zander says she feels guilty about taking vacations, about making more money than her employees, and about knowing that her husband is closer to their son than she is. Paul Downs says he recently reviewed 29 years of P&Ls and was reminded that he lost money in 18 of those years. He also explains why he routinely tells his employees (and us) precisely how much money he takes out of his business. Jay Goltz, meanwhile, says he’s now embarrassed to be called a CEO and acknowledges that he’s thought maybe he should have worked 20 percent less while building his business, but isn’t sure if that would have resulted in 20 percent less revenue or perhaps 100 percent less revenue.
53 min
June 15, 2021 Adventures in Candyland
This week, Stephanie Stuckey tells Jay Goltz and Dana White about moving closer to the candy factory she recently bought to get a better feel for the people, the operation, and the challenges. Right now, those challenges include recruiting enough employees, absorbing increased supplier prices, and figuring out how much she should raise her own prices: “We can only give up so much of our margin, right?” she tells us. To which Jay responds, “Why give up any?” Plus: we talk about competing for labor with Amazon, whether to require employees to get vaccinated, how to manage legal fees, and whether Dana’s feelings of FUD have eased.
43 min
June 08, 2021 Feeling the FUD: Dana White Fears She Isn’t Ready to Franchise
This week, Dana White tells Paul Downs and Jay Goltz why she’s experiencing FUD—fear, uncertainty, and doubt—over whether she’s really ready to sell franchises in Paralee Boyd. She’s concerned because her hair salon is having some issues with customer service. On the other hand, her head of operations, Ashley, is telling her, “If you wait to expand your business until every customer is happy and until everything is perfect, you will stay at one location for the next 50 years.” Plus, Paul resolves his cybercrime, and we find out whether Paul, Jay, and Dana have done anything to prepare for a ransomware attack. It turns out one of them has.
42 min
May 18, 2021 We’re Raising Wages for Everybody
This week, Paul Downs, Jay Goltz, and Dana White talk about confronting inflation, raising their prices, what businesses owe their employees, and the venture-backed competitor who’s opening a store in Jay’s backyard. Among the questions we discuss are: Would you take back a rebound employee? Are unemployment payments the main reason owners are struggling to fill jobs? Is there anything wrong with taking business from another business? How many companies are truly disruptive? And do owners take all of the risk? Or are there risks for employees, too?
48 min
May 11, 2021 I Think People Are Ready to Get Back to Work
Is your office open? Is everyone coming back? Or are you going hybrid? Is everyone getting vaccinated? Are you offering them incentives to get vaccinated? When do the masks come off? Are you having a problem filling jobs? Have you had to increase what you pay? Paul Downs tells us, “The people who really seem to want the job and are enthusiastic about it don't have the skill-set. And the people with the skill-set don't seem to actually care about completing the process. So we did hire one guy who started a week ago Monday, and he quit three hours later.” This week, Paul, Stephanie Stuckey, and William Vanderbloemen compare notes on what they’re experiencing as we all search for that new normal.
41 min
May 04, 2021 Did It Have to Get Crazy at Basecamp?
This week, Jay Goltz, William Vanderbloemen, and Dana White discuss whether Jason Fried, the embattled co-founder and CEO of Basecamp, has displayed courageous leadership or lost his you-know-what. Widely admired for building a tech company that didn’t take venture capital and didn’t pursue growth for growth’s sake, Fried is co-author of a book called It Doesn’t Have to Be Crazy at Work. All of which made it somewhat disorienting last week when things did indeed get crazy at Basecamp. It started when Fried published a blog post decreeing there would be no further discussion of political issues at the company, but it soon became clear that this was not just about coworkers arguing Trump vs. Biden. And by Friday, at least a third of the company’s 57 employees had resigned. In this episode, we go searching for lessons.
45 min

About 21 Hats Podcast

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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,…