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

It’s Not a Circuit-Board Business. It’s an Asset

This week, in episode 224, special guest Karla Trotman explains, step by step, how she has managed to navigate the challenges and opportunities that only a family business can offer. Karla grew up around a manufacturing business, Electro Soft , that her father started, but she never intended to make a career of it. Instead, she found success in corporate America, but over time, she also came to realize the true wealth-building power of owning a business, any business. “It's not a beauty salon,” ...

Dec 10, 202451 minEp. 224

Dashboard: Do Small Businesses Have to Innovate to Succeed?

In many cases, Shawn Busse tells us this week, they do, which is why he believes all businesses should be innovating constantly. That’s a lot to ask of small businesses, many of which are just trying to make it to the next payroll, and Shawn acknowledges that there are exceptions. But if, for example, a private equity firm starts buying up your competitors and investing money in them, innovation may be your best hope. How do you get started? Shawn offers some concrete steps to consider if you wa...

Dec 09, 202420 min

It's a Pathetic Budget, But We'll Hit It

This week, in episode 223, Shawn Busse, Jay Goltz, and Sarah Segal talk about why they’re not going to hit their numbers for 2024 and what they’re expecting from 2025, especially regarding tariffs, immigration, and regulation. Shawn says his business has been producing and closing fewer leads. “Clearly,” he says, “we’ve gotta change something.” Jay doesn’t think furniture sales will recover until mortgage rates come down, and he’s bracing for tariffs and deportations that he hopes won’t actually...

Dec 03, 202454 minEp. 223

Dashboard: This Is 2025’s Killer App for Small Business

This week, Gene Marks tells us he’s found the next killer app for small business, and it’s not something that’s theoretical and might be ready sometime next year. It’s ready now, and it’s Google’s NotebookLM. Gene had reviewed it previously and found it wanting but took another look at the latest version and found it could do things like streamline a job search and spot anomalies in his financials. But Gene also offers a caveat for rolling out any AI app or even a CRM: if you don’t configure it ...

Dec 02, 202426 min

For Years, We Thrived Without Marketing. Now What?

This week, in episode 222, we bring you another Entrepreneurial Fish Bowl with Chris Hutchinson. These Fish Bowls are our virtual brainstorming sessions where we offer business owners the opportunity to pose a challenge they’re facing to a group of owners and entrepreneurs from the 21 Hats community. This time, our volunteers are Alvin Elbert, founder of A.R.E. Manufacturing , and his daughter Megan Perona, who explain that their company had its best year ever in 2022 but has seen business fall ...

Nov 26, 202452 minEp. 222

Dashboard: An Entrepreneurial Vision for America

This week, Victor Hwang shares some surprising reasons to be optimistic about entrepreneurship in America. For one thing, Victor, who is founder of Right To Start, an advocacy group, says that he can’t remember a presidential election where entrepreneurship was as much a part of the conversation as it was in this one. For another, he points to a series of policy changes at the local level that have made it far easier to start businesses and that he believes will serve as a blueprint for other ju...

Nov 25, 202428 min

The D.E.I. Backlash Hasn’t Changed Mel Gravely’s Story

In 2021, Mel Gravely wrote a book, Dear White Friend , that was aimed primarily at fellow business owners. In the book, Mel tried to make it easier for owners to have genuine conversations about race. He suggested strategies for those, perhaps motivated by the murders of Ahmaud Arbery and George Floyd, who might want to engage. He acknowledged that emphasizing diversity can be hard work. He acknowledged that some of his own efforts had failed. But he also pointed out that he himself had been, in...

Nov 19, 202440 minEp. 219

Dashboard: The AI Agents Are Coming!

This week, Gene Marks tells us that the first really meaningful AI applications aimed at smaller businesses will arrive in the coming months. Gene does offer some caveats, including his mantra: “Never buy the first version of anything from Microsoft.” But he also offers some tantalizing examples of things AI agents will do for business owners in the very near future, like qualifying sales leads and then putting a sales rep through a role-playing exercise to prepare for a specific client. What sh...

Nov 18, 202421 min

Managing the Unexpected Risks of Entrepreneurship

This week, in episode 220, Paul Downs and Jay Goltz talk about the risks they didn’t see coming. While everyone knows there’s a risk that a business can fail because it just doesn’t work, there are lots of other, less obvious risks. These are not the risks you lose sleep over, but they’re real, and if you don’t manage them, you can expose yourself needlessly to a slew of problems. Because most people learn about these risks the hard way, Jay and Paul set out to create a top 10 list of them, but ...

Nov 12, 202445 minEp. 220

Dashboard: Businesses Can Still Save on 2024 Taxes

This week, Gene Marks offers some timely tips on ways you can reduce your tax burden. As you probably know, it’s a good time to consider buying an electric vehicle or some capital equipment. But Gene also offers some less obvious suggestions. For example, if you’re looking to increase your employee compensation, there can be tax advantages to paying more of their health insurance coverage rather than giving them a raise. Also, if you own the business with a spouse, Gene explains how you might be...

Nov 11, 202420 min

I'm Not Building Wienermobiles My Whole Life

This week, in episode 219, special guest Travis LeFever shares the unusual journey he and his co-founder wife, Amanda, have taken to build Mission Mobile Medical, which makes mobile health clinics in Greensboro, NC. That journey started with Travis partnering in a construction business by taking out 39 credit cards to borrow $250,000. The business did well, and he eventually bought out his partner, but when Travis’ father died unexpectedly, he was moved to sell the construction business and look...

Nov 05, 202447 minEp. 219

Dashboard: Getting Job Candidates to Search for You

This week, Shawn Busse talks about something that everyone kind of knows but too few businesses emphasize: remarkable things can happen when businesses improve their workplace culture and let the world know about it. Shawn shares his approach to building a brand as an employer and explains why the payoff can easily be hundreds of thousands of dollars.

Nov 04, 202433 min

A Few Good Plumbers

This week, in episode 218, special guest Rich Jordan tells Shawn Busse and Jay Goltz what it was like buying a small plumbing business in 2020 despite having very little experience with either plumbing or business—but having spent 10 years in the Marine Corps. “When I reflected on my time in service and what I did well and what I enjoyed,” Rich tells us, “it was when I was on a small team with high stakes, far forward, far from the flagpole, responsible for making decisions and sustaining oursel...

Oct 29, 202453 minEp. 218

Dashboard: This Is How to Use LinkedIn

This week, Shawn Busse walks us through his LinkedIn strategy: how often he writes, what he writes about, what he posts on his own page, what he posts on the company page, and how he promotes his business without promoting his business. Most importantly, Shawn explains why he believes his posting helps Kinesis attract both employees and clients.

Oct 28, 202433 min

‘Things Are Going to Suck’

This week, in episode 217, Laura Zander tells Shawn Busse and Jay Goltz about her approach to buying businesses. Laura says she simply recognizes that for a period of time, life will be miserable for her and for her team. That’s what happened almost a year ago when she bought two businesses that were a challenge to integrate. And now, just as things have calmed down a bit, she expects it to happen again as she eyes another acquisition. It’s also what she expects to happen as she and her husband ...

Oct 22, 202444 minEp. 217

Dashboard: The Issues That Matter to Business Owners

With the election only two weeks away, John Arensmeyer, founder and CEO of Small Business Majority, talks through what’s at stake for small businesses, including what the campaigns are saying about taxes, regulation, immigration, tariffs, and manufacturing. Plus: Given the likelihood that, regardless of who wins the White House, a closely divided federal government is likely to be with us for some time, Arensmeyer also explains what small businesses can hope for at the state and local levels.

Oct 21, 202422 min

‘Being Civilized Ain’t Gonna Do It’

This week, in episode 216, Shawn Busse and Jay Goltz talk about the trendy job interview strategy of trying to get beyond canned responses by asking candidates unexpected questions along the lines of, “If you were a superhero, what powers would you have and why?” Or, “What animal best represents you as a person?” Not surprisingly, Jay isn’t a big fan of those questions, and he offers an alternative strategy that features four questions of his own design. Shawn does like to ask unexpected questio...

Oct 15, 202443 minEp. 209

Dashboard: Learning From Helene and Milton

This week, Gene Marks talks about the lessons business owners should take from the devastating hurricanes of recent weeks. Gene is confident that the communities will build back better than ever, but of course, not all of the businesses will make it. We’ve been reminded that disaster can strike anywhere. What should business owners do to prepare?

Oct 14, 202418 min

When to Pull the Plug, When to Pull the Trigger

This week, in episode 215, Mel Gravely, Jennifer Kehrin, and Liz Picarazzi start out talking about the pain of being fired by a long-time client. “It still stings,” says Jennifer, who nonetheless surprised her team by writing a note of congratulations to the CEO of the company that took the business. The conversation moves on to the tradeoff that comes with deciding between promoting managers from within or hiring them from outside the organization: What if your people aren’t ready? What if the ...

Oct 08, 202456 minEp. 215

Dashboard: Don’t Dismiss Those Side Hustles

This week, Victor Hwang talks about the remarkable road trip he recently completed in which he got a fresh perspective on the state of entrepreneurship across America. At a time when many of us are consumed with the election and politics and all of the things that divide us, Hwang, who is founder and CEO of Right to Start, a non-partisan advocacy group, met with entrepreneurs in cities and towns from Southern California, across the northern part of the country and down to Washington, D.C., and f...

Oct 07, 202426 min

Should I Buy the Family Business?

This week, in episode 214, we bring you another Entrepreneurial Fish Bowl with Chris Hutchinson of Trebuchet Group . As you may remember, this is a virtual exercise where we offer a business owner—or in this case a potential business owner—the opportunity to pose a challenge he or she is facing to a group of owners and entrepreneurs from the 21 Hats community as part of a brainstorming session. In this case, it was BaLeigh Waldrop who explained why she has mixed feelings about buying the Miller ...

Oct 01, 202441 minEp. 214

Dashboard: The Real Problem with EIDL Money

This week, Ami Kassar, founder and CEO of MultiFunding, explains how it’s almost as if these past few years we’ve run a grand experiment to see what would happen if the government gave lots of business owners more money than they knew what to do with. In many cases, the businesses got far bigger Covid loans than they could have hoped to borrow conventionally, and they got them without having to go through the standard application process. In other words, they got the money without having to deve...

Sep 30, 202416 min

We Have More Work Than We Can Handle

This week, in episode 213, Paul Downs, Jaci Russo, and Sarah Segal talk about how and when they start planning for next year. And here’s one happy challenge they’ve all confronted: What do they do when they don’t have the capacity to handle all of the work that’s coming their way? Do they staff up? If so, what happens if the work subsequently falls off? Do they create a backlog? Do they miss deadlines? Do they raise prices? Plus: Jaci shares an AI tool she’s been using to learn more about the de...

Sep 24, 202450 minEp. 213

Dashboard: We Are in a Talent Crisis

This week, Rob Levin, says there’s a talent crisis in America, but you wouldn't know it reading most business publications. That’s because the crisis is affecting smaller businesses much more than bigger businesses. Levin, co-founder and chairman of WorkBetterNow, which provides remote workforce and virtual assistant services to small businesses, says he keeps hearing the same thing from owners who come to him looking for help. They just can’t find good people. Levin offers several pieces of adv...

Sep 23, 202427 min

Why You Should Run Your Business on EOS (Or Not)

This week, in episode 212, Shawn Busse, Paul Downs, and Laura Zander call on their own experiences to assess whether the EOS operating system—as explained in Gino Wickman’s book Traction—lives up to its promise of freeing owners from frustration, helping them put the right people in the right seats, and generating all of the scale they want. Laura hired an implementer to install EOS in her business years ago. Paul took more of a do-it-yourself approach, picking and choosing from the book’s sugge...

Sep 17, 202450 minEp. 212

Dashboard: Shawn Busse and the $4,000 Hole

This week, Shawn explains how a plumbing job went awry -- and more importantly, what it says about the “professionalization” of the blue-collar trades. That professionalization—along with the accompanying private equity dollars and the roll-ups and the MBAs—has certainly brought benefits. But it seems there’s been a price to pay as well.

Sep 16, 202423 min

Is This the Succession Plan For You?

This week, in episode 211, Jay Goltz and special guests Peter Koehler and Jimmy Kalb discuss the hottest new thing in succession planning. You may recall that earlier this year Peter was a guest on an episode in which he explained how he helped Laura Anderson sell her seafood restaurant to what’s known as an employee ownership trust or a perpetual purpose trust. Both Jay and Jimmy listened to that episode and were intrigued. Both had questions for Peter. So we recorded a conversation in which we...

Sep 10, 202446 minEp. 211

Dashboard: The Confusion Over Small Business Taxes

This week, Gene Marks tries to sort through some confusion. First, he talks about Kamala Harriss’s proposal to 10X a small business tax deduction, which sounds great except that it’s not really going to help small businesses. And then he addresses the comments of a Houston CPA who asserts that small businesses have the best tax deal in America. Gene sees it a little differently.

Sep 09, 202429 min

Best of: Turning a Failing Nut Shop into Nuts.com

This week, I’m replaying an oldie but goodie, an episode that Shawn Busse and I recorded with Jeff Braverman, who turned his family’s failing retail business into a thriving ecommerce business. I’m replaying this episode both because Jeff has a great story to share, with lots of takeaways, and because—well, actually, because I took a little time off last week. But listen to this: Jeff walked away from a career as an investment banker and went to work in the family’s nut store, the Newark Nut Com...

Sep 03, 202452 min

How to SAVE a Customer

This week, in episode 210, Jay Goltz, Jaci Russo, and Jennifer Kerhin discuss some of the systems they’ve created that have made their businesses successful. Jay established a process that helps employees diffuse conflicts with angry customers. Jaci has a process that tracks the performance of her agency’s lead-generation efforts and has helped her target clients more precisely. And Jennifer recently created a process to deal with change orders that makes it easier to walk the line between offen...

Aug 27, 202442 minEp. 207
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