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: Gene Marks Would Rather Not Employ Gen Z

“I don’t have the time to deal with them because my resources are limited,” Gene Marks tells Loren Feldman this week. But he’s just fine hiring Millennials, and he explains why. Plus: The cheap money days may be over, but there’s a silver lining to that: Venture-backed businesses may actually have to operate like real businesses. And Chewy offers lessons in both customer service and social media.

Jun 20, 202225 min

I Think You Need to Hire a PR Firm

This week, in episode 112, we welcome a new regular to the 21 Hats Podcast crew: Sarah Segal, founder and CEO of Segal Communications, a public relations firm based in San Francisco. First, Sarah tells Jay Goltz and Liz Picarazzi how she built her firm. Then, Jay and Liz ask Sarah all of their questions about public relations: How much outreach should they do themselves? Should they hire a PR specialist or a full-service agency? Should they approach journalists directly or through a publicist? A...

Jun 14, 202249 min

Dashboard: Inflation, Recession, the Metaverse. Oh, My!

This week, Gene Marks and Loren Feldman talk about whether it’s time to panic about inflation and recession, how smaller businesses are managing their inventories through these unpredictable times, why businesses that take digital payments through a service like Venmo are going to have to be more careful, and what, if anything, the metaverse is likely to mean for the typical small business.

Jun 13, 202224 min

Bonus Episode: I Didn’t Appreciate It Until I Almost Lost It

This week, in a special bonus episode, Greg Wittstock, founder of Aquascape, explains how he invented the backyard pond industry, how he improvised a business model, and how he almost lost it all. After failing at franchising, Wittstock decided to give away his pond building expertise and marketing to landscape contractors in what he calls “a franchise system without a franchise fee.” And it worked. Always candid to a fault, he recounts how the business shot to $59 million in annual sales, why i...

Jun 10, 202242 min

Fire Your Franchise Consultant

As listeners to this podcast know, Dana White has a remarkable array of opportunities before her, including company-owned hair salons, franchised salons, salons on military bases, hair products, and POS software. But especially since the pandemic, she has struggled to get traction. This week, in episode 111, special guest Ami Kassar, an expert in small business finance, guides Dana through a discussion of how she might prioritize those opportunities and get them financed. Ami and Dana consider s...

Jun 07, 202239 min

Dashboard: A Gusher of Money

This week, Gene Marks talks us through the State Small Business Credit Initiative, or SSBCI, which is a tad complicated but well worth figuring out. While the actual offerings vary by state, as the name suggests, there is $10 billion on the table in the form of grants, loans, and venture capital that could conceivably help almost any business. Plus: the dangers of hitting customers with fine-print fees and surcharges, an assessment of New York City’s efforts to eliminate onerous regulations, and...

Jun 06, 202226 min

What Would Deming Say?

This week, in episode 110, Kelly Allan—a consultant who specializes in sharing the principles espoused by the late management guru W. Edwards Deming—returns to the podcast for a conversation with Paul Downs, Jay Goltz, and Laura Zander. After World War II, you may recall, Deming was sent to Japan, where he was largely credited with resuscitating the devastated economy. He of course went on to become tremendously influential here, too. And if you read his books or scan his “14 points” for managem...

May 30, 202255 min

The Early Warning Signs

“I see it, and I feel it,” Liz Picarazzi tells Shawn Busse and Jay Goltz this week, in episode 109, a conversation about the looming recession many are predicting. But Liz is not hunkering down. In fact, she has launched an ambitious marketing campaign that relies not on Google AdWords but on Google Alerts. She’s also taking some advice from Carey Smith, the founder of Big Ass Fans, that she didn’t want to hear when it was first offered. Plus: How some owners trap themselves in miserable busines...

May 24, 202249 min

Dashboard: It’s Still About Hiring

This week, Lou Mosca, COO of American Management Services, which works with small businesses all around the country, talks about why hiring—and not recession or inflation—remains his clients’ biggest concern and what he and his clients are still learning about recruiting. Plus: Lou sees banks overreacting and warns about the dangers of online lending.

May 23, 202217 min

Have You Looked at Your Employee Handbook Lately?

This week, in episode 108, Jay Goltz and Dana White talk about their employee handbooks. Do they take them seriously? Or is it just boilerplate? Has anything changed since the pandemic? Is the handbook the place to remind employees that they are hired at will and can be fired at any time with or without a reason? Are there issues that should not be addressed in the handbook? When was the last time they updated it? When was the last time they read it? “Me, personally?” responded Jay. “Actually pi...

May 17, 202245 min

Dashboard: The Marketing Crapshoot

This week, Gene Marks tells Loren Feldman why he thinks investing in small business marketing is a lot like going to Vegas or Atlantic City—especially if you don’t have good data. But, he says, there are things you can do to improve your odds. Gene and Loren also discuss why Gene is rethinking the CRM systems he recommends, why business travel is coming back stronger than many expected, and why we’re experiencing both a labor shortage and a wave of layoffs at the same time.

May 16, 202224 min

Does Firing People Ever Get Easier?

This week, in episode 107, Shawn Busse, Jay Goltz, and William Vanderbloemen discuss whether the old line about hiring slow and firing fast makes sense during a labor shortage. As William puts it, “What if you do have to hire fast? How do you do that? What if you do want to keep people even if you might have wanted to get rid of them before? How do you do that without ruining your culture?” Plus: How do you know it’s really time for someone to go? And what happens when employees share their sala...

May 10, 202245 min

Dashboard: Gene Marks Went Remote Years Ago. He Hates It

This week, Loren Feldman and Gene Marks resume their weekly conversations about the most important stories affecting business owners, starting with why Gene was ahead of his time in taking his business remote and why he thinks it’s left his company dysfunctional. Plus: what should owners take from the latest strong jobs report? And how will businesses be affected if the Supreme Court does indeed overturn Roe v. Wade?

May 09, 202219 min

My Deal Has Come Apart

This week, in episode 106, we start with an update of how 21 Hats has been doing since its sale brought new resources and new ambitions (Spoiler alert: It’s not going great!). Then, Dana White tells Shawn Busse and Jay Goltz about the progress she’s made on multiple fronts: attempting to sell franchises to revive her struggling Midtown Detroit location, to open new salons at Fort Bragg and in Dallas, and to secure financing. The owners discuss Dana’s financing options—venture capital, private eq...

May 03, 202251 min

The Anchor Price

This week, in episode 105, Shawn Busse, Paul Downs, and Liz Picarazzi talk pricing, specifically how they use an anchor price—the first number they offer prospective customers. Do they anchor low to avoid scaring anyone away? Or do they anchor high to disqualify unlikely buyers and to make the actual sale price feel more comfortable? Plus: Liz explains the remarkable, dream-come-true, my-product-in-Times Square PR gift she just received. Of course, this is entrepreneurship, so even when dreams c...

Apr 26, 202256 min

Bonus Episode: The Marketing Magic of Answering Customer Questions

This week, in a special bonus episode, Marcus Sheridan talks about the revolutionary strategy that he used to save his pool-building business during the Great Recession and that he’s been sharing ever since. That strategy is to volunteer answers to the questions your customers always ask—especially the questions you’ve been taught not to answer, at least not until you absolutely have to, such as those about pricing and potential problems with your product or service and who your best competitors...

Apr 19, 202242 min

Do You Really Want That Shiny Object?

This week, in episode 104, Laura Zander tells Shawn Busse and Jay Goltz about her eight-month roller coaster ride pursuing an acquisition. The deal would bring a new brand and profitable revenue at a reasonable price. To Laura, the creative challenge and opportunity are exciting—“really, really exciting”—but the financials are a concern. “Do I do this?” she asks. “Is it worth it?” And then there’s the broker, whose numbers don’t add up and who wants to collect his fee—including his piece of the ...

Apr 12, 202242 min

Do You Take Money off the Table?

This week, in episode 103, Shawn Busse, Paul Downs, and Jay Goltz discuss their philosophies about taking money off the table vs. reinvesting it in the business. Of course, you can’t take money off the table unless there’s money on the table. Paul tells us that he once calculated his average earnings for his first 22 years in business and they came to about $11 an hour. But he now expects to make more money in the next five years than he did in the previous 35. We also talk about content marketi...

Apr 05, 202248 min

What If I Get the Contract?

This week, in episode 102, Liz Picarazzi tells Jay Goltz that she’s pursuing multiple sales opportunities—and ponders what would happen if those opportunities actually came to fruition. Would her company, Citibin, be able to handle the additional volume? “In my fantasy world, where I am a lot,” Liz says, “I look at where this could go. And just like you, Jay, I go to, ‘How in the world would I produce all of these?’” Liz and Jay also talk about the pros and cons of pricing transparency: Do you v...

Mar 29, 202240 min

Why I Sold 21 Hats

This week, in episode 101, the tables are turned, as Loren Feldman announces the sale of 21 Hats and takes questions from Shawn Busse, Karen Clark Cole, and Jay Goltz. The buyer is Toby Scammell, founder of Womply, which provides software services to small businesses and helped more than a million of them obtain Paycheck Protection Program loans. Loren will continue as editor-in-chief, but as he explains, much of what this will mean for 21 Hats has yet to be determined—including, for example, wh...

Mar 22, 202244 min

We Are Survivors

This week, in episode 100, two years after the pandemic first hit, Shawn Busse, Jay Goltz, and Liz Picarazzi talk about what they’ve learned, what they’re doing differently, and whether their businesses have gotten weaker or stronger. Leading up to the pandemic, Shawn—still carrying scars from the Great Recession—did a series of workshops on how to prepare for the next recession. “And so in that regard,” he tells us, “we were really well prepared” for the pandemic. Plus: public companies are inc...

Mar 15, 202248 min

We Tried That Brand Thing. It Didn't Work.

This week, in episode 99, Shawn Busse, Paul Downs, and Jay Goltz talk about the tendency of many businesses to obsess about their logo, their website, and the need to drive more leads. To which Shawn suggests concentrating first on customer experience. And Jay agrees: “It's better business,” he says, “to make your customers happier than to keep trying to find new customers.” But Paul has his doubts: “You can have your internal house in order, as I do,” he says. “And you can have a great website,...

Mar 08, 202249 min

Somebody’s Hiring All of These People

This week, in episode 98, Jay Goltz tells Liz Picarazzi and Laura Zander that he’s had a revelation about The Great Resignation. Yes, he’s lost some people, but not necessarily his best people. “It shook the tree out,” he says, which is why he thinks businesses should be careful right now about hiring too quickly. Meanwhile, Liz talks about her latest product, a bear-proof trash enclosure, and why introducing it has been challenging. And Laura tells us what happened with the salesman she tried t...

Mar 01, 202244 min

We Don’t Have a Brand

This week, in episode 97, Paul Downs talks about why furniture makers traditionally have not stamped their names prominently on their work—and why he’s rethinking that now. That change of heart is the direct result of Paul’s unlikely experience connecting two very different businesses: One a Mennonite company manned by master craftsmen, and the other a startup manned by tattooed hipsters with a mastery of Kickstarter. Not only has the resulting culture clash changed the way Paul thinks about his...

Feb 22, 20221 hr 5 min

Why Not Become the Strategic Buyer?

This week, in episode 96, Shawn Busse, Karen Clark Cole, and Jay Goltz compare notes on some of the many choices they’ve made building their businesses, such as the emphasis they’ve placed on growth, the risks they see in growing through acquisition, and—as Karen has recently experienced—the rewards of being acquired. They also discuss whether The Great Resignation, despite forcing companies to pay higher wages and work harder to find and keep talent, just might be a good thing for business owne...

Feb 15, 202245 min

Dashboard: Is the Labor Shortage Easing?

This week, Loren Feldman and Gene Marks talk about why he thinks inflation is pulling workers back into the workforce. Plus: Is it a big deal that Apple is going to let businesses take payment by iPhone? And Gene explains just how easy it can be to steal money from a company’s bank account—and what you can do to protect your business.

Feb 14, 202221 min

Have You Considered Not Taking Investors?

This week, in episode 95, Jay Goltz, Liz Picarazzi, and Dana White talk about the advantages and disadvantages of bringing in outside capital and expertise—something both Liz and Dana have considered. “I have a background in Russian literature and credit card marketing,” says Liz. “I'm now a manufacturer, so if I could have an outside investor who either brought that to the table or could help me with it, that would be really valuable.” But of course, there are trade-offs. We also talk about Dan...

Feb 08, 202253 min

Dashboard: A Tale of Two Cities (Fort Myers and Philadelphia)

This week, Loren Feldman and Gene Marks talk about whether a four-day work week is a benefit small businesses can use to lure employees. Plus: Is your website ADA compliant? And what do you do if you get a complaint that it’s not? And Gene talks about why he prefers Florida’s response to the pandemic to Philadelphia’s, which he says is killing the city’s restaurants. But are Philadelphia’s restaurants suffering because they can’t seat the unvaccinated? Or is it because they can’t keep their cust...

Feb 07, 202224 min

The Game Has to End at Some Point

This week, in episode 94, Shawn Busse, Paul Downs, and Jay Goltz talk about their evolving succession plans. There are lots of options—selling the business, turning it over to a family member, selling it to an employee stock ownership plan, holding a going-out-of-business sale, just walking away—and they all come with advantages and disadvantages. Shawn, Paul, and Jay take us through their current thinking and also tell us whether their businesses are prepared for the possibility that they could...

Feb 01, 202254 min

Dashboard: Is Pay Transparency Good for Businesses?

This week, Loren Feldman talks to Lou Mosca, COO of American Management Services, about the growing trend of making salaries public—either because municipalities require it or because businesses choose it. Plus: if the economy is growing at its fastest pace in decades, why doesn’t it feel like it? And how should businesses plan? And a recent study found that more than half of the 2,000 workers surveyed had resignation letters already written. What does this suggest about The Great Resignation?

Jan 31, 202220 min
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