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Private Equity Has Never Been More Alluring

The investors come bearing money and with promises of relevant expertise and a glide path to that elusive next level. Should entrepreneurs believe them?

What Is 21 Hats?

At 21 Hats, we’re not going to tell you how to run your business. But we are going to publish news articles, Q&As, webinars, and podcasts that feature business owners speaking frankly about what it takes to build a business.

'I Have Been Literally Hiding From My Numbers'

Like a lot of business owners, Laura is very good at a lot of things — but intimidated by her financials. It doesn’t have to be that way.

The Temptation of Growth

It’s easy to get excited thinking about geographic expansion. But for Citibin, at least for now, there’s no place like home.

Episode 70: Oh, No! They Accepted Our Offer
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.’”

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Episode 65: 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.

Episode 63: Feeling the FUD: Dana White Fears She Isn’t Ready to Franchise

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?

Episode 68: 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.

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Never miss a 21 Hats Podcast episode
‘I Was Raised By Entrepreneur Wolves’

Rob Dyrdek—high school dropout, professional skateboarder, reality TV star, founder of the Dyrdek Machine—has learned a lot of entrepreneurial lessons since getting scammed the first time he started a business. For example, he never starts a business unless he sees a clear path to the precise outcome he has in mind.

What’s in It for the Owner? A Skeptical Conversation about ESOPs

Both Jeff Taylor and Jim Kalb run companies with employee stock ownership plans. Jay Goltz is thinking about implementing one — but he’s got questions, such as: Where does the money to buy the company come from?

What’s Wrong With Small Business Marketing?

It’s not always about marketing. Sometimes, the real issues go deeper. Sometimes, before you can figure out how to sell, you have to figure out who you are.

Brent Beshore Takes a Radical Approach to Private Equity

Brent Beshore likes to say of the businesses he invests in, “Boring is beautiful.” It’s one of the things that sets him and his firm, Permanent Equity, apart. He runs a private equity fund with more than $300 million in capital, but he’s not really a private equity guy.

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