21 Hats Podcast - podcast cover

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 won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they had to lay off employees, how they wound up with way too much inventory, why they don’t have a succession plan, and even why they are concerned about their own mental health. Visit 21hats.com to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.
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Episodes

Dashboard: Are We Really Going to Ban TikTok?

This week, Gene Marks tells Loren Feldman that he thinks the ban signed by Montana's governor is a political stunt that could do real damage to businesses that have come to rely on the app. And yet, there seems to be momentum for similar bans in other states and even at the federal level. Plus: how to avoid ERTC fraud, why bankruptcies are skyrocketing, and should the business community be doing more to warn against risking default?

May 22, 202320 min

Marketing Workshop: I Didn’t Know It Was Going to Work

This week, Shawn Busse and Loren Feldman talk to John Garrett about his contrarian approach to newspapers, marketing, and competition. Garrett has built a Texas-based chain of print newspapers that has managed to outcompete established news organizations and digital platforms for both community engagement and local advertising. Not surprisingly, when he first took out a $39,000 credit card loan in 2005 and started telling people that his business model would feature a monthly print publication t...

May 16, 202353 min

Dashboard: Yes, It’s Time to Worry about the Debt Ceiling

This week, Gene Marks tells Loren Feldman that businesses should be making contingency plans in case there’s a default, especially if they rely on government contracts. Be careful how you spend and how you stash your cash. Plus: Gene gloats a bit about the end of the age of the worker (and then has some second thoughts). He also says reports of the death of the metaverse are greatly exaggerated and that it wouldn’t be so terrible if the government loses the ability to regulate.

May 15, 202318 min

I’m Not a Real CEO

This week, in episode 152, Jay Goltz, Liz Picarazzi, and Sarah Segal talk about the inherent conflicts between being an entrepreneur and being a CEO—and the different skill-sets each role requires. Does it make sense for the same person to do both jobs? Is being CEO even a full-time job? And when does it make sense to replace yourself as CEO? Liz says she’s thought about it. Jay, not so much: “Could I have found somebody 10, 15, 20 years ago who was a better manager? Sure. But it just wasn't wor...

May 09, 202344 minEp. 152

Dashboard: Solving Monopolies, Immigration, Tipped Wages, and the Debt Ceiling

This week, John Arensmeyer, CEO of the Small Business Majority advocacy group, and Loren Feldman talk about some of the most intractable problems confronting business owners. And John offers some reason for hope -- mostly, he says, because there’s a growing, bipartisan effort to level the playing field for smaller businesses. The debt ceiling, of course, is another matter.

May 08, 202318 min

Bonus Episode: Not Sold on ESOPs? There’s a New Alternative

This week, two special guests who have built highly successful companies talk about what they ultimately plan to do with those companies. Ari Weinzweig is co-founder of Zingerman’s Community of Businesses, a collection of mostly food-related companies that are an iconic part of Ann Arbor, Michigan. Brad Herrmann is co-founder of Text-Em-All, a software firm based near Dallas that helps organizations deliver personalized, informational, and emergency messages by text and by phone. Both Zingerman’...

May 02, 202350 min

Dashboard: Where’s the Money?

This week, Gene Marks takes Loren Feldman through a case study of how easy it is even for profitable businesses to get caught in a cash crunch. The problem, Gene explains, is that business owners often have to pay taxes on earnings that have yet to reach the owners. Where does the money go? To inventory, to capital expenditures, to accounts receivable among other places. How can owners avoid the crunch? By staying on top of their finances.

May 01, 202326 min

When CEOs Behave Badly

This week, in episode 151, our conversation starts with Shawn Busse and Jay Goltz trying to understand why CEOs keep going viral for their misguided attempts to rally the troops. Shawn suspects CEO screeds have always existed—they just haven’t been recorded. He also thinks they tend to come more from public company CEOs who are beholden to shareholders. Jay thinks they’re just morons. “I really don't understand how someone could be smart enough to run a big company like that,” he says, “and be s...

Apr 25, 202342 minEp. 150

Dashboard: America’s Economy Is Better than Americans Think

Yes, demand is tapering, and a recession is looming, Gene Marks tells Loren Feldman, but this is a great economy and a great country and people should stop complaining! Plus: Gene explains how some business owners get the state to pay for their employee training, how restaurants are finally adopting technology, and how to make sure your employees aren’t stealing from you. One tip: if you think an employee is stealing from you, send the employee on vacation.

Apr 24, 202321 min

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

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 fi...

Apr 18, 202348 minEp. 148

We’re Still Buying Inventory

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: Wi...

Apr 11, 202337 minEp. 149

Dashboard: Is There Really a Credit Crunch?

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.

Apr 10, 202326 min

Recession? That’s When You Need to Attack

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’...

Apr 04, 202351 minEp. 148

Dashboard: Winter Is (Still) Coming

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.

Apr 03, 202322 min

I Just Cut My Pay

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 sal...

Mar 28, 202349 minEp. 146

Dashboard: Gene Marks Is Not a Fan of Mandated PTO

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.

Mar 27, 202322 min

I Can’t Have a Handle on Everything

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 recen...

Mar 21, 202336 minEp. 146

Dashboard: Bank As I Say, Not As I Do

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.

Mar 20, 202319 min

For Wunderkeks, It Really Is Go Big or Go Home

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...

Mar 14, 202347 min

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

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.

Mar 13, 202322 min

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

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 t...

Mar 07, 202350 min

Dashboard: The Three Reports Every Business Owner Needs

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).

Mar 06, 202325 min

What It Means to Break $1 Million in Revenue

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?

Feb 28, 202347 minEp. 144

Dashboard: Coping With HR Issues Without an HR Staff

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.

Feb 27, 202320 min

Marketing Workshop: Selling Cookies on LinkedIn

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...

Feb 21, 202343 min

Dashboard: The Price of Tipping, Virtual Offices, and Men’s Underwear

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.

Feb 20, 202322 min

ESOPs Are Great. But Not for Me

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 convinced—co...

Feb 14, 202353 minEp. 143

Dashboard: The Good News About Gen Z

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.

Feb 13, 202323 min

Walking Away From a Salary

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 ...

Feb 07, 202343 min

Dashboard: So You Think Building a Business in the U.S. Is Hard?

Well, it is, but after spending a month in London, Gene Marks says inflation, regulation, and entitled employees make it even worse there. In fact, Gene says he’s going to stop complaining about conditions in the U.S. (We’ll see.) Plus: why Gene thinks even small businesses should offer unlimited PTO, how to make sure you don’t fall prey to one of the Employee Retention Tax Credit scams, and Gene’s list of things a small business can do with ChatGPT.

Feb 06, 202323 min
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