21 Hats Podcast
Download on the App Store

21 Hats Podcast episodes

  • Are You Ready to Sell Your Business?
    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 skeptically. It seems to be a well accepted fact, he says, that most people who sell their business end up regretting it. Plus: as we head into budget season, we find out whether the three owners are planning to give raises. And in this week’s Morning Report News Quiz, we learn what happened to Inspiration, Imagination, and Fantasy.
    38 min
  • This Week, The Pandemic Hit Home
    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 paid if local rules require them to quarantine after they return? And if traveling employees do have to quarantine, will these businesses have enough staffers available in December and January to function? And then there was the question Laura demanded of Jay after Jay explained how exactly he was exposed to the virus: “Wait, no,” she said, “You didn't answer my question. Were you wearing a mask?”
    40 min
  • What Would You Do With $200,000 Right Now?
    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 does she want to take it in the form of a convertible note, which can convert to an equity stake in her company? And perhaps, more importantly, how exactly is she going to spend the money? As she tells Paul Downs and Jay Goltz in this conversation, she’s thinking about spending it on marketing, on opening another location, or on creating retail products for sale online or in her salons. What do you think Dana should do? Please email your thoughts to [email protected], and we’ll share them on the podcast and in the Morning Report.
    41 min
  • Man, If I Win...
    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 Dana. “When you have first money in from Dan Gilbert, it bodes well for your company.” Dana also tells Karen and Paul that she’s just made her most important hire ever, an operations manager who had a compelling reason for wanting to join Dana. Plus: the Morning Report News Quiz.
    39 min
  • REVISITED: That’s The Price
    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 those interviews were with women who started companies from scratch and sold them successfully—learning all sorts of lessons along the way.
    43 min
  • I Would Be Scared, Frankly
    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 giving away for free, and the designs for an unbuilt website that we had hoped to one day charge subscription fees for. Any thoughts?”
    38 min
  • Landlords and Real Estate and Banks, Oh My!
    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 one that will fund the loan—even though she already has SBA approval for a loan. And Jay wants to take out a mortgage on a building he owns outright just to have some extra cash on hand, but he’s on his 10th bank. “You can’t get discouraged,” Jay tells Laura. To which Laura responds: “Come on, what do you mean, ‘You can't get discouraged?’ You see my face? It’s called discouragement.” Plus: the Morning Report News Quiz returns.
    39 min
  • When’s This Gonna Be Over?
    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 conclude it was the best thing that could have happened to his business. It’s been painful, he says, but, “in some ways, we needed a jolt, and this gave it to us.” Jay understands: “When things get really bad like this, we start paying attention to stuff that we should have been paying attention to before.” Plus: do the three owners have a plan for how their businesses would continue to operate if they were incapacitated by COVID?
    45 min
  • There’s a Thin Line Between Confident and Delusional
    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 door. As Jay tells us, “If we didn't figure out how to fire, we're not on this show, because we're out of business at this point.” Plus: Did Paul keep his promise to see if he could connect with someone at Google to discuss his AdWords campaign?
    37 min
  • We Kind of Live or Die by Google
    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 buy high-end boardroom tables because of the crisis, he’s considering shifting tactics again: “I'm wondering whether I should sort of go on the offensive,” he says, “and try to increase my marketing in the face of these declines in sales, or whether nothing I do would make any difference at this point.” Plus: Is it better to manage your own digital marketing or to hire a specialist? Our panelists disagree.
    43 min

About 21 Hats Podcast

From the publisher's feed

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,…

Best of 21 Hats Podcast

Ranked by our users in the last 21 days

More shows like 21 Hats Podcast

Stuff You Should Know by iHeartPodcasts

Stuff You Should Know

78,389 Listeners

Wait Wait... Don't Tell Me! by NPR

Wait Wait... Don't Tell Me!

38,675 Listeners

Marketplace by Marketplace

Marketplace

8,749 Listeners

The Knowledge Project by Shane Parrish

The Knowledge Project

2,698 Listeners

How I Built This with Guy Raz by Guy Raz | Wondery

How I Built This with Guy Raz

30,157 Listeners

The Daily by The New York Times

The Daily

111,874 Listeners

Up First from NPR by NPR

Up First from NPR

56,435 Listeners

Masters of Scale by WaitWhat

Masters of Scale

3,979 Listeners

David C Barnett Small Business and Deal Making M&A SMB by David C Barnett

David C Barnett Small Business and Deal Making M&A SMB

43 Listeners

The Peter Attia Drive by Peter Attia, MD

The Peter Attia Drive

7,986 Listeners

The Prof G Pod with Scott Galloway by Vox Media Podcast Network

The Prof G Pod with Scott Galloway

5,385 Listeners

All-In with Chamath, Jason, Sacks & Friedberg by All-In Podcast, LLC

All-In with Chamath, Jason, Sacks & Friedberg

10,184 Listeners

PBD Podcast by PBD Podcast

PBD Podcast

4,225 Listeners

The Ezra Klein Show by New York Times Opinion

The Ezra Klein Show

15,917 Listeners

Prof G Markets by Vox Media Podcast Network

Prof G Markets

1,443 Listeners