21 Hats

21 Hats Podcast

Business EN ↓ 548 episodes

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, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should be...

Author

21 Hats

Category

Business

Podcast website

www.spreaker.com

Latest episode

Jul 10, 2026

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Episodes

All It Takes Is One Mistake 15.12.2020

This week, in our final podcast taping of the year, Paul Downs, Jay Goltz, and William Vanderbloemen discussed the impact this year has had on their businesses and on themselves. William talked about the positive side of having to get back to a startup mentality: “It's definitely been a silver lining in the middle of a very dark cloud.” Paul talked about hoping he can offer his employees a good pl...

The Great COVID Churn 08.12.2020

This week, Paul Downs, William Vanderbloemen, and Laura Zander talk about William’s prediction that 2021 will be a year of employee turnover. His theory, which he says he’s already seeing evidence for, is that pent-up forces that were blocked by the pandemic this year will be unleashed in 2021—especially as vaccines arrive and the economy improves. His advice: Make sure your best people feel appre...

She Was a Hiring Goddess 24.11.2020

This episode is dedicated to Ivy Garfield. Back in 1996, Jay Goltz had no real hiring process and the results to prove it. “My hiring success rate,” Jay tells us, “was probably, I don't know, 30 or 40 percent, which isn't much better than whoever walks in you hire.” And then he asked Ivy Garfield to take over his hiring. As Jay explains, Ivy brought an instinct, an understanding of how to assess p...

We’ll Find Something for Them to Do 17.11.2020

This week, starting with a conversation about crucial hires Dana White and Laura Zander have made recently—an operations manager for Dana, a salesperson for Laura—we found ourselves exploring some of the great unresolved debates of entrepreneurship. Which comes first when hiring: filling specific needs or finding places for good people? With sales people, do you motivate by paying commission or bu...

Are You Ready to Sell Your Business? 10.11.2020

This week, Paul Downs, Jay Goltz, and William Vanderbloemen assess the damage of a stressful year. We started with the impact the year has had on the value of their businesses. Then we discussed whether they would be ready to sell their businesses if a generous offer were to come along. That prospect, Jay tells us, would likely cause him to do some soul-searching, but he would consider it skeptica...

This Week, The Pandemic Hit Home 03.11.2020

For Jay Goltz, William Vanderbloemen, and Laura Zander, concerns about the pandemic loomed large this week as one of them had to self-isolate in his basement after being exposed to the virus. That fact helped surface a number of interesting questions: Are the three owners being careful enough? What should they tell employees who choose to travel over the holidays? Should employees who travel get p...

What Would You Do With $200,000 Right Now? 27.10.2020

And so, yes, Dana White was in fact the big winner at last week’s Detroit Demo Day, taking home the top prize of $200,000 for her hair salon business, Paralee Boyd, which specializes in serving women with thick and curly hair and which has an unusual walk-in-only business model. Of course, Dana now has some decisions to make: Does she want to take the money in the form of a zero-interest loan? Or...

Man, If I Win... 20.10.2020

This has not been an easy year for Dana White, who has had to close one of her two hair salons and who has struggled, amid the pandemic, to keep the other one staffed. But this week she reveals to Karen Clark Cole and Paul Downs that she’s a finalist for a potentially game-changing pitch competition. “A $200,000 investment from Quicken Loans is a huge validator when you're looking to grow,” says D...

REVISITED: That’s The Price 13.10.2020

This, to say the least, has been a challenging year. So this week, we’ve decided to bring you two inspirational success stories by revisiting one of our earliest podcast episodes. Way back in November of 2019, Karen Clark Cole and Loren Feldman attended EY’s Strategic Growth Forum in Palm Springs where we conducted a series of interviews with participants in EY’s Winning Women program. Two of thos...

I Would Be Scared, Frankly 06.10.2020

In this week’s episode, the tables are turned. This week, it’s host Loren Feldman who fields questions and takes advice after he explains why the BusinessAdvantage TV Podcast will once again be The 21 Hats Podcast. “The bottom line is: I am now the proud owner of a pre-revenue startup that has a daily email newsletter that we've been giving away for free, plus this weekly podcast that we've been g...

Landlords and Real Estate and Banks, Oh My! 29.09.2020

In this week’s episode, Dana White, Laura Zander, and Jay Goltz talk about their real estate challenges. Dana decided to close one of her locations rather than keep dealing with an overly aggressive landlord. Laura, fearing her landlord was going to throw her out, decided to buy a building. But she hasn’t been able to close on the deal because, while she’s been to six banks, she has yet to find on...

When’s This Gonna Be Over? 22.09.2020

This week, six months into the crisis, Paul Downs, Jay Goltz, and William Vanderbloemen take inventory. What does the crisis mean for the future of their businesses? Has it changed them as leaders? Has it affected their relationships with their employees? And they come to some counter-intuitive conclusions. For one, William tells us that he suspects he will one day look back on the crisis and conc...

There’s a Thin Line Between Confident and Delusional 15.09.2020

This week, Karen Clark Cole, Paul Downs, and Jay Goltz talk about whether their businesses need another round of government support, whether in the age of COVID they monitor their employees’ behavior away from the office, and whether there are aspects of running a business they would like to be better at. One thing they say they are all good at is taking action when an employee has to be shown the...

We Kind of Live or Die by Google 25.08.2020

In this week’s conversation, Karen Clark Cole, Paul Downs, and Laura Zander talk about their approaches to digital marketing. After years of relying on Google AdWords as his only form of marketing, Paul tells us, he stopped his $12,000-a-month spend a few years ago—relying instead on organic traffic. What happened when he stopped? His sales actually went up. But now, with fewer people looking to b...

The Case for Not Pivoting 18.08.2020

In this week’s conversation with Paul Downs, William Vanderbloemen, and Laura Zander, Paul explains why he’s not planning to pivot his business—even as his sales collapse. Normally, Paul says, his most reliable customers are other business owners. When they call to ask about a custom boardroom table, he and his sales staff know they are likely to buy. Right now, though, in the midst of a pandemic...

The Most Expensive Hire You Will Ever Make 11.08.2020

For years, business owners complained about how tight the job market was and how hard it was to find good employees. Well, so much for that. Funny thing, though. In this week’s episode, William and Jay talk about how, in many ways, hiring has gotten even harder during the crisis. Part of it is having to rely more heavily on Zoom. And part of it is having to sift through the many people who are sud...

Hair Is Segregated 04.08.2020

In this conversation, Karen, Jay, and Dana discuss diversity in hiring and marketing. Dana talks about the challenge of getting white customers to come to a hair salon that is mostly Black. Karen talks about the challenge of persuading Black candidates to join a company that does not have a lot of Black employees: “So the question is not: are they out there? They're out there. I guarantee they're...

My Jay Goltz Face 28.07.2020

Paul Downs, Jay Goltz, and Dana White talk about how they would know if it was time to close their business, how long it takes to really grow up as a manager, what they’ve learned about managing—and occasionally firing—employees. “I think my staff hears me but eventually does what they want to do,” says Dana. “And that can be very draining because you wonder, ‘Well, why? I pay you. We’ve had train...

I’m Not Going to Shut the Doors 21.07.2020

This week, we introduced a new member of the podcast team, Paul Downs, whose company, Paul Downs Cabinetmakers, makes custom conference tables. Paul wrote about how close his company came to failing in both The New York Times’ You’re the Boss blog and in his own book, "Boss Life: Surviving My Own Small Business." That was during the Great Recession. Unfortunately, Paul is once again finding it cha...

Would You Start Your Business Today? 14.07.2020
Doomsday Fatigue 07.07.2020

In last week’s episode, we asked our panel of business owners this question: Would you be doing anything differently with your business if you knew for sure that a second shutdown order was coming? It seemed like a pretty straightforward question, but it triggered one of our guests, Jay Goltz, who called it a “stupid” question and encouraged the other panelists not to answer it. So this week, we d...

That’s a Stupid Question 30.06.2020

As the numbers of new coronavirus cases explode across the country, Karen Clark Cole, Jay Goltz, and Laura Zander talk about how they are trying to make plans for their businesses. The conversation heats up a bit as it becomes clear that one of our owners (Hi, Jay!) isn’t quite ready to confront the possibility that he might have to deal with another shutdown. By contrast, Laura tells us, “We're o...

Do You Feel Shame Taking Money From the Government? 23.06.2020

Jay Goltz, William Vanderbloemen, and Dana White—all of whom took Paycheck Protection Program loans—respond to an opinion piece that says “competent” business owners shouldn’t have had to go begging “shamelessly” for a government bailout, which got a particularly strong response from Jay: “I'm thinking of all of those entrepreneurs who are trying to run a business, trying to make happy customers—r...

I’ve Never Raised My Prices 16.06.2020

Karen Clark Cole, Jay Goltz, and Dana White discuss their pricing strategies and why raising prices can be such a challenge: Dana tells us she has often wondered, “If I raise my prices, is this the decision that's going to make me close my doors?” And Jay recalls a customer who came into his picture framing shop and told a sales consultant, “Wow, that's a lot more than the other place I've gone to...

I’m Stressed 09.06.2020

Karen Clark Cole, William Vanderbloemen, and especially Dana White have a painful, impassioned, uncomfortable conversation about trying to position their businesses and lead people in the aftermath of George Floyd’s murder and the ensuring protests. What do we tell customers? What do we tell employees? What do we tell black employees? Dana challenges us to take a stand—even if it’s uncomfortable—e...

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