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PODCAST

21 Hats Podcast

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

business entrepreneurship

All Episodes

48:01

‘It’s Going to Take $8 Million in Financing’

21 Hats Podcast ·

2023/04/18

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 will require a significant investment. “I spend my days doing

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37:01

We’re Still Buying Inventory

21 Hats Podcast ·

2023/04/11

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 maintaining a credit line equivalent to 10 percent of sales. Plus:

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25:54

Dashboard: Is There Really a Credit Crunch?

21 Hats Podcast ·

2023/04/10

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 employers.

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50:44

Recession? That’s When You Need to Attack

21 Hats Podcast ·

2023/04/04

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 expand her offerings to include digital marketing. Plus: Laura, who’s

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21:54

Dashboard: Winter Is (Still) Coming

21 Hats Podcast ·

2023/04/03

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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49:07

I Just Cut My Pay

21 Hats Podcast ·

2023/03/28

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 hold-off on the marketing campaign? Or should he cut his own salary

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21:55

Dashboard: Gene Marks Is Not a Fan of Mandated PTO

21 Hats Podcast ·

2023/03/27

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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36:17

I Can’t Have a Handle on Everything

21 Hats Podcast ·

2023/03/21

This week, in episode 146, Jay Goltz and Laura Zander talk about the limits of their own management. Once a business gets past a certain size, no owner can do everything or even be aware of everything. But where do you draw the line? Does the owner need to be conversant with most aspects of management, marketing, and finance to oversee the business? This came up, in part, because Jay told us recently that his framing shops routinely ask customers how they learned of the business and that a recent

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19:22

Dashboard: Bank As I Say, Not As I Do

21 Hats Podcast ·

2023/03/20

This week, in the aftermath of the Silicon Valley Bank collapse, Gene Marks says he banks at Wells Fargo — but that’s not what he recommends. His suggestion: Find a good community bank, spread your money around to play it safe, and then relax. He also says you should consider going to a four-day work week. And not because it’s good for your employees, but because it’s good for you.

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46:46

For Wunderkeks, It Really Is Go Big or Go Home

21 Hats Podcast ·

2023/03/14

This week, in episode 145, Hans Schrei explains why he’s pursuing a deal with Costco and why his vision is to get Wunderkeks cookies into every supermarket in the country. When Jay Goltz counters that instead of thinking big, or thinking small, maybe Hans should think medium, Hans says that may no longer be possible with consumer packaged goods: “The little brand that grows and thrives by growing little by little doesn't really exist any more in this space,” he says. Underlying the discussion of how

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22:14

Dashboard: Taxes, Regulation, and a Punch to the Face

21 Hats Podcast ·

2023/03/13

This week, Gene Marks and Loren Feldman discuss what it means for small businesses that some tax deductions are going away, some new regulations are arriving, and Joe Biden has released a budget proposal. Gene also counters the Bare Minimum Monday meme with a suggestion for what practitioners of Bare Minimum Mondays can do on Tuesday.

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49:34

Marketing Workshop: Turning a Failing Nut Shop into...

21 Hats Podcast ·

2023/03/07

This week, Shawn Busse and Loren Feldman talk to Jeff Braverman about how he walked away from a career as an investment banker and went to work in the family’s nut store, the Newark Nut Co. “My dad and my uncle told me I was nuts,” says Jeff. But with an instinct for taking risks—like acquiring the URL Nuts.com—Braverman has turned the family business into an internet juggernaut, unleashing years of explosive growth. And despite being a former investment banker, he’s managed to do that without

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24:46

Dashboard: The Three Reports Every Business Owner Needs

21 Hats Podcast ·

2023/03/06

This week, Gene Marks tells Loren Feldman that too few business owners really know how their business is performing. He suggests three reports that they should be reviewing -- beyond their monthly financials -- if they want to get a better grip on managing their business. Plus: Gene explains how businesses can save money on energy and why everyone should hire a CRM consultant (like Gene, for example).

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46:40

What It Means to Break $1 Million in Revenue

21 Hats Podcast ·

2023/02/28

This week, Liz Picarazzi and Sarah Segal talk about their attitudes toward growth, including how they set goals, the tension between revenue and profit, deciding when growth requires additional bodies, choosing between contractors and employees, and how they would use the money if someone were to give them a million dollars to invest in their business. Plus: What will it take for them to consider themselves successful?

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20:18

Dashboard: Coping With HR Issues Without an HR Staff

21 Hats Podcast ·

2023/02/27

If, like Gene Marks, you think dealing with employees is a pain, Gene has a suggestion for you: professional employer organizations, or PEOs. It’s a way to outsource all of the functions of HR—even including, if you want, health insurance. Gene also talks about why too many businesses ignore the many resources government has to offer business owners, why it’s time to start preparing for a government shutdown, and why Kevin O’Leary--aka Mr. Wonderful--is a buffoon.

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43:07

Marketing Workshop: Selling Cookies on LinkedIn

21 Hats Podcast ·

2023/02/21

This week, Shawn Busse and Loren Feldman are doing something a little different. This is the first in a series of episodes we’re calling Marketing Workshops. In an attempt to confront one of the biggest pain points business owners face, we’re offering a series of conversations with owner-operators about their marketing experiences: what’s worked and what hasn’t. We’re starting with Grayson Hogard, co-founder of Grove Cookie Company. For Grayson and his wife, Marie, the company is a bootstrapped side

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22:16

Dashboard: The Price of Tipping, Virtual Offices, and...

21 Hats Podcast ·

2023/02/20

This week, Gene Marks and Loren Feldman talk about why tipping is a terrible system that we probably will never change, why Gene believes giving up a real office for a virtual office didn’t save him money, and what the purchase of mens underwear can tell us about the economy. Plus: Gene says there are 27 things businesses can do with ChatGPT right now—although he does offer a few caveats.

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53:27

ESOPs Are Great. But Not for Me

21 Hats Podcast ·

2023/02/14

Last week, Jay Goltz continued his exploration of employee ownership, flying to Portland to meet up with Shawn Busse and Jim Kalb, a friend of 21 Hats who has already sold a portion of his business to his employees. The three owners planned to attend a conference promoting employee stock ownership, but things went somewhat awry. Jay and Shawn left the conference early, Jim canceled his flight, and as has happened before in his brushes with ESOP professionals, Jay walked away feeling

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22:46

Dashboard: The Good News About Gen Z

21 Hats Podcast ·

2023/02/13

This week, Gene Marks and Loren Feldman talk about what Gen Z values in a job. The research suggests it’s not the job -- it’s more about people and meaning. And that’s good news for smaller businesses, because those are things they can offer. But you might want to emphasize that in your job descriptions. Plus: Is this recession happening or not? And what will ChatGPT’s upending of search mean for all of the businesses who’ve been investing in SEO? They’re not going to be happy, says Gene.

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43:06

Walking Away From a Salary

21 Hats Podcast ·

2023/02/07

This week, in episode 142, Sarah Segal tells Shawn Busse and Jay Goltz why she’s decided to take her public relations business back after selling it two years ago to a larger firm so it could handle the back-end stuff and allow her to focus on public relations. For Sarah, the immediate result of the decision to break away has been an exhausting few months starting over, including reincorporating, finding health insurance, and reducing her own pay. Meanwhile, Jay suggests an old-school marketing

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