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: Stop Taxing Tips? Really?

This week, Gene Marks notes that the two major presidential candidates happen to agree on something, which is that we should stop taxing tipped income. Unfortunately, Gene explains, it’s a boneheaded idea. Plus: Gene’s been looking into the progress that manufacturing companies are making adopting artificial intelligence applications, and he says—at least when it comes to manufacturing—the promise of AI is starting to get real.

Aug 26, 202423 min

Can We All Be Purple Cows?

This week, in episode 209, Shawn Busse, Jaci Russo, and Jay Goltz discuss what it takes to stand out these days, especially if your business—like most businesses—isn’t exactly the Next Big Thing. What about trash collection? What if your business is selling scrap metal? What if you happen to be one of 69 picture framers in Chicago? What’s an owner to do to stand out then? Is it enough to execute really well? Can any business make itself remarkable? Shawn, Jay, and Jaci all believe it’s possible,...

Aug 20, 202442 minEp. 207

Dashboard: Can Kamala Harris Win Over Small Businesses?

This week, Gene Marks offers some suggestions as to what it would take for the presumptive Democratic nominee to earn his vote and those of other small business owners. Suggestion No. 1: make clear that in the debate over whether to extend the Trump tax cuts she favors keeping the Qualified Business Income Deduction for owners of pass-through businesses. He’d also like to see her promise fewer regulations and more tax breaks for owners trying to sell their businesses.

Aug 19, 202434 min

Whose Advice Are You Going to Take?

This week, in episode 208, Paul Downs, Mel Gravely, and Sarah Segal talk about the tricky calculation all entrepreneurs must make between sticking to their vision and accepting advice. Sarah explains why she is reluctant to take advice from people who don’t really know the inner workings of her business, which is pretty much everyone. Paul, on the other hand, says taking advice from outsiders helped save his business during the Great Recession. And Mel talks about why he thinks every business sh...

Aug 13, 202449 minEp. 206

Dashboard: The Benefits of Childcare, AI, and Silly Marketing

This week, Gene Marks talks about three very different topics. First, he explains how helping employees find affordable health care can actually generate business growth, and he walks through the ways even very small businesses can help. Next, Gene weighs in on proposed legislation in California that is designed to keep AI models from causing catastrophic harm. And finally, he explains how a new hire just out of college helped a Chevy dealer create a sitcom parody that went viral. But did it sel...

Aug 12, 202423 min

A Silicon Valley Bootstrapper Tells All

This week, in episode 207, special guest Sharon Gillenwater lets us in on some dirty little secrets about Silicon Valley. She’s the founder of two businesses. The first one was backed by venture capital and then destroyed by venture capital. Despite that experience, Sharon tried to raise capital for her second business, Boardroom Insiders , a software-as-a-service marketing tool that helps businesses sell to the top decision-makers at big corporations. But this time, the VCs weren’t interested. ...

Aug 06, 20241 hr 1 minEp. 207

Dashboard: Dear ChatGPT: Do a SWOT Analysis of My Business

This week, Gene Marks reminds us once again that AI tools by and large still aren’t ready for prime time, but he does find a handful of people doing interesting things with AI—like getting a fresh take on the risks and opportunities their business is confronting. Plus: Gene and Loren Feldman discuss whether Gene is right that his business taxes will definitely go up if Kamala Harris is elected president.

Aug 05, 202433 min

Beyond Trust Falls: An Event Planner Plans an Offsite

This week, in episode 206, Shawn Busse, Jay Goltz, and Jennifer Kerhin talk about what it takes to plan and execute an employee retreat—especially in our post-Covid, more-remote environment. Do you go offsite? Do you take everybody? Do you delegate the planning? Do you try to measure the ROI? Jennifer tells us about the interesting responses she got when she encouraged her employees at her retreat to ask her anything. Shawn explains why he let his leadership team do the planning—and didn’t set a...

Jul 30, 202451 minEp. 206

Dashboard: What We Can Learn from CrowdStrike

This week, Gene Marks explains the global tech outage: what actually happened, how seriously we should take it, and what business owners should do (but probably won’t) before the next outage. Those lessons include: 1) Try to keep some paper handy. 2) Stay calm. The internet is going to go down from time to time. 3) Have a disaster-recovery plan. 4) And if you don’t have a disaster-recovery plan, go to ChatGPT. PLUS: Gene discusses the upheaval in the real estate industry and why the CEO of an HR...

Jul 29, 202424 min

When They’re Not Quite Bad Enough to Fire

This week, in episode 205, Paul Downs, Liz Picarazzi, and Jaci Russo discuss how they review employees and how they make the hard calls when someone is right on the cusp. The conversation starts with a couple of tricky situations that Paul is trying to think through and then progresses through several other issues: Do you use personality tests to avoid or resolve personality conflicts? Paul, Liz, and Jaci have very different takes on Myers-Briggs and the like. Do you make sure no one is ever sur...

Jul 23, 202455 minEp. 205

Dashboard: What Are You Seeing Out There?

As CEO of MultiFunding, Ami Kassar sees a lot of small business P&Ls, and he sees how banks are responding to loan applications. And in his view, the ground is starting to shift—although he’s not sure where we’re headed. But in times of uncertainty, he emphasizes, there are always opportunities

Jul 22, 202417 min

Family Businesses Aren’t Dysfunctional. They’re Disastrous

This week, in episode 204, Jay Goltz and special guest Cathy Caroll talk about family businesses, with Jay asserting that they are even more combustible than most people realize and with Cathy offering some smart coping strategies. We start with Cathy explaining how her own experiences in a family business propelled her to write a book, Hug of War , and to become a family business coach. Why are family businesses so difficult? Well, says Cathy, it’s because you’re trying to combine a family mind...

Jul 16, 202450 minEp. 204

Dashboard: Don’t Sleep on the SSBCI

This week, John Arensmeyer, founder and CEO of Small Business Majority, reminds us that the State Small Business Credit Initiative is sending billions of dollars through the states specifically for small businesses. Because every state is handling the money differently and there is no one-stop shop for information, there is some confusion—but the money is real and John explains how to figure out if you’re qualified. Plus: He also explains why he’s surprised some business groups are celebrating t...

Jul 15, 202420 min

A Successful Owner Chooses an Innovative Exit

This week, in episode 203, special guests Laura Anderson, founder of Local Ocean , and Peter Koehler, her succession-planning advisor , explain why Laura decided to sell her thriving seafood business in a transaction that created a business model that is neither widely known nor widely understood. It’s called an employee-ownership trust, and there are only about 50 of them in the United States. But their numbers are growing here and abroad, and for good reason. The trust model offers owners some...

Jul 09, 202457 minEp. 203

Dashboard: Is It Time to Panic About Deficits?

No, says Gene Marks, who — it may surprise you to hear — offers three main reasons he doesn’t believe business owners should panic over the U.S. government’s growing debt. That said, he does believe that we are likely to have to operate in an environment of higher inflation and higher interest rates for some time, and he says that is likely to require some adjustment in the thinking of business owners.

Jul 08, 202421 min

I Used to Sell to Consumers

This week, in episode 202, Paul Downs, Jaci Russo, and Sarah Segal talk about how they wound up pitching their products and services not to consumers, but to other businesses. They all agree that selling to business is more profitable, and they all agree that it has other advantages, as well. “In general,” says Paul, “it's easier to sell to businesses because the person you're talking to, it's rarely their money.” But some aspects of selling B2B can be harder. For example, how do you break throu...

Jul 02, 202455 minEp. 200

Dashboard: SCOTUS Unleashes a Tsunami of Regulatory Chaos

This week, Gene Marks and Loren Feldman discuss the Supreme Court’s decision, released on Friday, that takes authority to interpret laws passed by Congress away from federal agencies and gives it to judges. Whatever you think of the merits of the ruling, Gene points out, it creates tremendous uncertainty for businesses trying to comply with the law. For example, a new overtime rule is supposed to go into effect today. Should businesses start following it, Gene asks? Or wait to see what happens w...

Jul 01, 202423 min

This Is Not How This Ends

This week, in episode 201, we bring you what we’re calling an Entrepreneurial Fish Bowl with Chris Hutchinson. As you may remember, we recorded one of these at our 21 Hats Live event in Fort Worth, where I shared some of my challenges trying to build 21 Hats and got feedback from the group. We recorded that conversation and turned it into a podcast episode. This time, we’re doing the same thing except it will be Jaime Echt, founder and CEO of The Crafters Workshop, who is going to explain her ch...

Jun 25, 202449 minEp. 198

Dashboard: Yes, of Course, AI Will Eliminate Jobs

Companies don’t like to admit it, says Gene Marks, but that’s kind of the point. So far, it’s mostly big companies with millions to spend that have been able to replace humans with bots, but he believes smaller businesses will soon be doing the same thing. Should we be worried about that? He doesn’t think so. Plus: Why a lot of businesses still don’t offer 401(k) plans. And if job candidates want to bring a parent along to an interview, Gene says he’s fine with that.

Jun 24, 202420 min

What Will Businesses Do If SEO Dies?

This week, in episode 200, Shawn Busse, Liz Picarazzi, and Jaci Russo talk about how the marketing world is turning upside down. For decades, business owners have treated search engine optimization as something of a religion. They may not have been able to explain it, but they had faith that, if they obeyed the rules, Google would discover their sites and rank them. But search engines are getting a lot less generous about sharing links, and Shawn fears there’s an apocalypse coming for businesses...

Jun 18, 202452 minEp. 200

Dashboard: Why Business-Book Advice Doesn’t Work for You

This week, Shawn Busse talks about why the business-advice books we’ve all read often fall flat. Shawn says it’s because much of what they suggest is predicated on a traditional model of a business that makes widgets. As a result, that advice may work fine if you are a manufacturer, but it’s far less likely to help if your product or service is more customized. That may seem obvious but the thinking Shawn describes remains deeply embedded in the small business mindset. One example: the implement...

Jun 17, 202425 min

I Decided to Slow Our Growth

This week, in episode 199, Jennifer Kerhin tells Shawn Busse and Jay Goltz that she finally managed to take her first real vacation since starting her business almost 20 years ago. The vacation is part of a decision she made last year to regroup a bit, in part by backing off on her sales and marketing outreach. The goal is to give her team and herself a bit of a respite while they catch their breath and while Jennifer institutes processes that will improve operations. Of course, that raises an o...

Jun 11, 202456 minEp. 198

Dashboard: Can You DIY a Business Acquisition?

This week, Tracy Bech, who is co-author of the “60 Minute CFO” and who has bought and sold businesses herself, offers some guidelines on how to approach an acquisition. Some of it is looking at the numbers, of course. Some of it is understanding the story behind those numbers. And some of it is psychological, controlling your emotions and maintaining a willingness to walk away from the deal if something doesn’t break right. And by the way, Tracy says, it’s never a bad idea to use the same lens t...

Jun 10, 202422 min

The Year So Far? It’s Difficult Out There

This week, in episode 198, we get updates from Laura Zander, Sarah Segal, and Jay Goltz. Laura wonders whether the time she’s put into integrating her latest acquisition might have been better spent focusing on her core businesses. Sarah, who has shifted to pursuing smaller clients, asks Laura and Jay to articulate the PR pitch that would interest them. But how do you evaluate the effectiveness of a PR campaign? Does it have to generate sales? Plus: Jay explains why he views confronting his curr...

Jun 04, 202448 minEp. 196

Dashboard: Gene Marks Says CEOs Will Not Be Replaced By AI

This week, Gene responds to a New York Times article suggesting that CEOs should be among those worrying about whether artificial intelligence will take their jobs. For one thing, companies could save a lot of money replacing their leaders with bots. But Gene’s not buying it—although he does see Microsoft and Google making big progress with their AI offerings, so much so that he’s adjusting the services his own business offers. He says it’s time for owners to start paying more attention to AI.

Jun 03, 202427 min

How to Sell a Business That Won’t Sell

We’re calling it a We-SOP. The term, coined by Jay Goltz, refers to a business transition that is something of a do-it-yourself ESOP, or employee stock ownership plan, but without the expense and complication and debt of a full ESOP. It’s a transition that lets owners get money out of what has been their life’s work. It’s a transition that lets loyal employees keep their jobs and preserve the company’s culture. And it’s a promising solution for the Silver Tsunami of retiring Baby Boomers because...

May 28, 202448 minEp. 197

How to Waste Money on Marketing

It’s easy! Anyone can do it! This week, in episode 196, Shawn Busse, Jaci Russo, and William Vanderbloemen talk about a whole slew of marketing challenges. From strategizing for trade shows, to whether your logo has to tell a story, to understanding what constitutes a brand, to whether that iPad ad Apple pulled was terrible or brilliant, they discuss what makes marketing so difficult. It all starts, Jaci says, with the industry’s refusal to set standards: “I can't find another industry that trea...

May 21, 202457 minEp. 196

Dashboard: The Software Isn’t the Problem

You are. That’s Gene Marks’ story, and he’s sticking to it. This week, Gene talks about all of the people who love to hate on Workday’s HR platform, and he argues that whatever problems exist are really the fault of the companies using the software, not the company that makes it. Plus: Gene tells us what we need to know about the latest ChatGPT upgrade. Spoiler alert: He says we will long remember the spring of 2024 as the moment when the true power of artificial intelligence became clear, but s...

May 20, 202423 min

Yeah, I Can Hold Myself Accountable

This week, in episode 195, Mel Gravely tells Jay Goltz and Liz Picarazzi about his recently executed succession plan, including what’s worked and what could have gone better. The main thing that could have gone better, Mel says, is his purchase of another small business where he says he misdiagnosed the challenges the business is confronting: “I thought they just had a bad model and they weren't managing it well. It was worse.” All of which leads to a discussion of the role that a board of advis...

May 14, 202453 minEp. 195

Dashboard: Gene Marks Explains "Open" Banking

This week, Gene talks about an intriguing banking trend that’s come out of Europe and could be headed our way. It sounds a little dicey, but it could take some of the work out of applying for a loan. Plus: business owners say they expect artificial intelligence to increase--not decrease--their headcount. Could they be right? And can we all agree on the definition of a small business?

May 13, 202433 min
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