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.
Last refreshed:
Follow this podcast in the Metacast mobile app to refresh it and see new episodes.
Download Metacast podcast app
Podcasts are better in Metacast mobile app
Don't just listen to podcasts. Learn from them with transcripts, summaries, and chapters for every episode. Skim, search, and bookmark insights. Learn more

Episodes

Dashboard: Is America Really Experiencing a Startup Boom?

Well, yes, actually, but Gene Marks and Loren Feldman discuss two questions: One, what exactly is driving the boom? And, two, are the startups substantial enough to matter? Or is this just about people losing their jobs and driving for Uber. Plus: what would you do if you owned fast food locations in California where the minimum wage for fast food workers will jump to $20 an hour in April. And what are business owners to make of the case the Supreme Court heard last week about the constitutional...

Jan 22, 202425 min

The Worker Co-Op Solution

In this week’s bonus episode, Cameron Madill takes us on his succession journey, which began years ago when he started having conversations with older business owners, many of whom seemed to feel trapped. They’d had a lot of success, they were proud of the business they’d built, but they weren’t sure what to do with it or how to leave it. None of the usual options seemed terribly appealing. Hoping to write a different ending, Madill, now in his 40s, started looking for better options much earlie...

Jan 16, 202454 min

Dashboard: AI, TikTok, and the Rise of Women Owners

This week, Shawn Busse and Loren Feldman talk about some big changes coming to the world of small business. At his consulting firm, Kinesis, Shawn is already beginning to experience the impact artificial intelligence is having on his industry. He knows B2B business owners who are spending a lot of time on TikTok—and they’re not just watching dancing videos. And his client base has already shifted dramatically toward women-owned businesses.

Jan 15, 202421 min

New Year’s Resolution? Make. Some. Money.

This week, in episode 179, Shawn Busse, Paul Downs, and Laura Zander talk about why 2023 was so challenging for them and what they plan to do differently in 2024. “Last year was a year when I knew I was going to be making a bunch of investments and didn't expect to show much or any of a profit,” says Paul. “And I absolutely nailed that goal.” Shawn, meanwhile, thinks his new marketing scheme is working, and Laura is addressing her issues by going shopping — shopping, that is, for businesses. She...

Jan 09, 202449 minEp. 176

Dashboard: The State of Small Business, 2024

This week, John Arensmeyer, founder and CEO of the advocacy group Small Business Majority, tells us that he senses considerable optimism among the many business owners in his network notwithstanding some concern for looming policy and economic issues. Among those issues, John tells Loren Feldman are: access to capital, the cost of health care and health insurance, relations between franchisors and franchisees, price discrimination against smaller businesses, the burden of the new Corporate Trans...

Jan 08, 202425 min

This Is What It Takes to Build a Business, Vol. 2

This week, we take a look back at the conversations we had last year about the many rewards and responsibilities of business ownership, highlighting some of our happiest, smartest, funniest, and most difficult exchanges from the past year. Along the way, we discuss topics such as escalating salary demands, how much profit a business should make, a new way to sell a business, the problems with ESOPs, how to sell cookies on LinkedIn, breaking a million dollars in annual revenue, escaping the valle...

Jan 02, 20242 hr 11 minEp. 176

Bonus Episode: The Unlikely Plan That Launched Down North Pizza

So here was Muhammad Abdul-Hadi’s idea for a pizza joint: First, buy a building in one of the most troubled neighborhoods in one of the poorest big cities in the country. Open a restaurant despite having no experience in the food industry and do it during the pandemic when many restaurants are failing. And hire only people who, like Abdul-Hadi, are convicted felons. If that business plan sounds a little dicey to you, rest assured you would not be the first to suggest that to Abdul-Hadi. But he d...

Dec 19, 202348 min

Dashboard: Do the Math. Lean into A.I. Play Squash

In our last conversation of the year, Gene Marks tells Loren Feldman about the nine habits that he believes have helped him build a business. Those habits include meeting regularly with his accountant, meeting regularly with his clients, and over-paying his employees. Gene saves what he considers the most important suggestion for last: Make time to enjoy your family.

Dec 18, 202324 min

What Are Your Goals for 2024?

This week, in episode 177, Shawn Busse, Liz Picarazzi, and Jaci Russo discuss what they learned in 2023 and what they expect from 2024. After a tough year, Shawn is optimistic that his clients, having survived the turbulence of the past few years, are ready to spend money and try something different. Liz explains why she’s been willing to discount her products as much as 40 percent on Cyber Mondays and tells us about some new products she has in the works. Early in the year, Jaci, thinking she w...

Dec 12, 202346 minEp. 177

Dashboard: Your Last-Minute, Year-End Tax Moves

This week, Gene Marks shares his suggestions for anyone looking to save a little on taxes. Start with your retirement account. Better yet, start planning ahead for next year. Plus: What’s the best CRM for solopreneurs and microbusinesses? What artificial intelligence apps for business are worth trying right now? And what does Philly native Gene make of the $140 Philly cheesesteak?

Dec 11, 202324 min

We Need to Go Back to Marketing for Humans

This week, in episode 176, Paul Downs tells Jay Goltz and Jaci Russo about the latest developments in his year-long campaign to stop relying so heavily on Google AdWords. At a specially arranged, two-day marketing event, Paul got to sit down with a series of architects and designers who had already been vetted and who he hopes will become repeat customers. So far, Paul says, the results look promising. Plus, we also discuss: Do you write your website copy to please Google or to please people? Is...

Dec 05, 202345 minEp. 176

Dashboard: Don't Blame Your CRM

This week, Gene Marks talks through the latest developments in customer relationship management software, which is both his area of expertise and a real pain point for many business owners. Among other things, Gene tells us about the impact artificial intelligence is already having on CRM, including what A.I. makes better as well as what it makes worse. Plus: How do you get salespeople to use your system properly? And what should you do if you’re completely frustrated and ready to dump your syst...

Dec 04, 202328 min

Bonus Episode: Are Salespeople Built or Born?

It used to be that best practices in sales were pretty standard across the board. But since the pandemic and with the advent of artificial intelligence, says Lance Tyson, founder of the Tyson Group sales consultancy, it’s like the Wild West out there. Suddenly, everyone’s playing by different rules, and the best sales approach can vary, depending on the seller, the target, the industry, the region of the country. The keys, Tyson says in this week’s bonus episode, are to pay attention and stay fl...

Nov 28, 202351 min

Clients and Taxes and Bears, Oh My!

This week, in episode 175, Jaci Russo explains how she put an end to her eight-month drought of new clients. Jennifer Kerhin takes us through the bureaucratic nightmare of managing remote workers based out of state (“That is a headache that I don't wish on my worst enemy,” says Jaci, who has found a way to sidestep the problem). And Liz Picarazzi brings us up to date on her ongoing struggle to get her trash enclosures certified as bear-resistant. The common thread to these challenges may lie in ...

Nov 21, 202337 minEp. 174

Dashboard: It’s the Data, Stupid

This week, Black Friday and Small Business Saturday will represent hugely important shopping days for many retailers. But Gene Marks tells Loren Feldman that the sales those days generate aren’t necessarily as important as the data they generate -- so long as the retailers are smart enough to capture it. Gene also talks about why business owners need to understand that when they sign their tax returns, they—and not their accountants—are responsible for what the returns show. Plus: why Gene loves...

Nov 20, 202321 min

Start Up, Throw Up, and Grow Up

This week, in episode 174, Dana White drops a few surprises. When we began this podcast in 2020, Dana had two promising hair salons in Detroit that she’d named after her grandmother, Paralee Boyd. She had an innovative business model designed specifically for women with thick and curly hair. And she was on her way to winning a prestigious business plan competition. All of which presented her with a wide array of opportunities to consider. Would she continue to bootstrap? Would she franchise? Wou...

Nov 14, 202339 minEp. 174

The I-Hate-Marketing Approach to Marketing

This week, in episode 173, Shawn Busse tells Jay Goltz and Mel Gravely why he doesn’t want his firm, Kinesis, to be known as a marketing agency. Part of it is his sense that people just don’t trust marketers. But Shawn also believes that what Kinesis offers its clients is much more than just marketing. Hearing that prompts Mel to take us through his recent decision to spend a lot of money rebranding his construction business, which he says created alignment throughout the business and would have...

Nov 07, 202350 minEp. 173

Dashboard: Can You Fire Employees Who Won’t Return to the Office?

This week, Gene Marks warns business owners that the National Labor Relations Board has taken an action that could make it harder to fire employees who won’t come back to the office. But is that really the case? Gene’s also concerned about a new rule proposed by the Equal Employment Opportunity Commission that makes it even more important that business owners review their policies and training regarding harassment of employees. And then Gene reviews the case of an employee who filed some relativ...

Nov 06, 202324 min

Best of: Sometimes, Dreams Do Come True

If you’ve been listening to this podcast, you know we spend a lot of time talking about all of the things that can go wrong for a business owner. And yes, in part because we started recording these conversations just a couple of months before the pandemic hit, we’ve had plenty to talk about. Even this year, with the worst of the pandemic behind us, we’ve been talking about everything from excess inventory to lost clients to layoffs to ineffective marketing to surviving the valley of death. So, w...

Oct 31, 202343 min

Dashboard: It’ll Change Everything

This week, Shawn Busse tells Loren Feldman why he’s long been skeptical of big data, especially the data many businesses collect from their customers. What’s the alternative? Shawn suggests doing something radical and having actual conversations with your customers, especially your best customers. Shawn also talks about why it seems so many businesses are struggling even as the economy is surging, at least according to the latest GDP figures. Plus: What exactly is wrong with the titans of Silico...

Oct 30, 202326 min

And Some Days the Bear Eats You

This week, in episode 172, Liz Picarazzi tells Jay Goltz and Sarah Segal that her trip to a bear sanctuary in Montana to get her trash enclosures certified as bear-resistant did not go precisely as planned. Because of a logistical snafu, she has not yet obtained either the certification or her real goal: a marketing video of the grizzlies attempting to crack open her baited enclosure. Fortunately, things went better for Liz in a more traditional marketing venue, a trade show in Chicago where she...

Oct 24, 202342 minEp. 172

Dashboard: Gene Marks Expects an A.I. Backlash

For months, Gene has been telling us about all of the cool things we’ll be able to do with Microsoft’s Office 365 and Google’s Workspace when those companies integrate artificial intelligence into their platforms. Gene’s still excited about the possibilities, but he’s also more than a little annoyed, because both Microsoft and Google are planning to charge us quite a bit more for their A.I. enhancements. Gene also talks about automated invoicing, which he believes is going to displace a lot of e...

Oct 23, 202321 min

We Haven’t Signed a New Client in Eight Months

This week, in episode 171, we meet Jaci Russo, the co-founder and CEO of BrandRusso and the latest addition to the 21 Hats Podcast team. Jaci tells Jay Goltz and Laura Zander how she went from working for Barry Diller to starting her marketing agency. Jaci also explains why she recently decided to introduce a four-day workweek and why she thinks her agency has now gone eight months and counting without signing up a new client—the longest such stretch in more than 20 years in business. “I find it...

Oct 17, 202343 minEp. 171

Dashboard: The Insane Burden of Health Insurance

This week, we learn that Gene Marks and Bernie Sanders agree on something, which is that there are better ways to handle health insurance than making business owners responsible for providing it to their employees. Isn’t running a business hard enough without this financial and bureaucratic burden? Does it really have to be this way? Plus: Why Gene thinks what he calls “the era of the worker” won’t last forever. And what business owners need to know and do before they lay off or fire employees.

Oct 16, 202322 min

Bonus Episode: An Accidental Entrepreneur

It took a series of sad losses to turn banker Channon Kennedy into an entrepreneur. If a friend hadn’t lost his son and if Channon’s mother and sister hadn’t been diagnosed with cancer, she never would have designed, prototyped, manufactured, and started selling the Morgan Square , a tool that can save carpenters time while framing a project. CDhannon is just getting started, but we’ll keep in touch as her journey continues.

Oct 13, 202323 min

Bonus Episode: The Employee Engagement Industry Has Failed

In this week’s bonus episode, Bill Fotsch, a business consultant, explains why he thinks much of the effort that he and many others have put into creating employee engagement over the past three decades has been wasted effort—well intentioned, but wasted. The fact is, Fotsch says, employees today are no more engaged than they were some 30 years ago when the concept of employee engagement first gained currency. So what’s the answer? Fotsch has come to the conclusion that it’s something he calls “...

Oct 10, 202336 min

It’s Like Planning Your Own Funeral

This week, in episode 170, Jay Goltz tells Shawn Busse about the latest stop on his journey to figuring out whether an employee stock ownership plan is right for his business. Jay’s latest adventure includes waking up at 4:30 in the morning in Minneapolis too anxious to sleep—“Oh my God, what am I getting myself into here?”—and deciding to leave the seminar and drive back to Chicago. But on that six-hour return trip, Jay says his anxiety turned into clarity. In fact, he thinks he’s pretty sure h...

Oct 03, 202343 minEp. 170

Dashboard: About That Shutdown

When Gene Marks and I recorded this episode of Dashboard on Friday, we were pretty sure the government was going to shut down. That, of course, didn’t happen so you can fast-forward through our brief remarks early in the show—or perhaps you would enjoy hearing Gene state confidently that he’s known all along that a shutdown was inevitable. We also discuss what Gene’s been hearing from business owners as he criss-crosses the country talking to various groups. And Gene talks about the IRS’s decisi...

Oct 02, 202319 min

I’ve Never Had to Lay off Anyone Before

This week, in episode 169, Sarah Segal tells Shawn Busse that the other shoe has dropped. A couple of months ago, as she’s shared here previously, Sarah lost two big clients in one week. Now she takes us through her decision to lay off three of her employees, including what it means for the business and what it means for Sarah’s own role in the business. Before the layoffs, she had gotten to the point where she was working on the business—but now that’s changed. “I'm not working on the business,...

Sep 26, 202340 minEp. 169

Dashboard: Do You Know What Your Margins Are?

This week, Tracy Bech talks about why it’s important, from time to time, to review your margins, to compare them with those of others in your industry, and to look for ways they might be improved. You might even find ways to adjust your business model. The first step, of course, is to make sure you know what those margins are. Plus: when is it time to start thinking about next year?

Sep 25, 202318 min
For the best experience, listen in Metacast app for iOS or Android