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PODCAST

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

business entrepreneurship

All Episodes

51:26

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

21 Hats Podcast ·

2024/12/10

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,” she

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20:03

Dashboard: Do Small Businesses Have to Innovate to...

21 Hats Podcast ·

2024/12/09

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 want

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54:26

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

21 Hats Podcast ·

2024/12/03

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

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25:34

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

21 Hats Podcast ·

2024/12/02

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

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52:01

For Years, We Thrived Without Marketing. Now What?

21 Hats Podcast ·

2024/11/26

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 off

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28:27

Dashboard: An Entrepreneurial Vision for America

21 Hats Podcast ·

2024/11/25

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

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39:42

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

21 Hats Podcast ·

2024/11/19

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 his

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21:01

Dashboard: The AI Agents Are Coming!

21 Hats Podcast ·

2024/11/18

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 should

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45:09

Managing the Unexpected Risks of Entrepreneurship

21 Hats Podcast ·

2024/11/12

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 I

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19:48

Dashboard: Businesses Can Still Save on 2024 Taxes

21 Hats Podcast ·

2024/11/11

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

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47:16

I'm Not Building Wienermobiles My Whole Life

21 Hats Podcast ·

2024/11/05

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 for

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33:00

Dashboard: Getting Job Candidates to Search for You

21 Hats Podcast ·

2024/11/04

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.

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53:00

A Few Good Plumbers

21 Hats Podcast ·

2024/10/29

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 ourselves

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33:21

Dashboard: This Is How to Use LinkedIn

21 Hats Podcast ·

2024/10/28

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.

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43:50

‘Things Are Going to Suck’

21 Hats Podcast ·

2024/10/22

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 Doug

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22:00

Dashboard: The Issues That Matter to Business Owners

21 Hats Podcast ·

2024/10/21

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.

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42:42

‘Being Civilized Ain’t Gonna Do It’

21 Hats Podcast ·

2024/10/15

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 questions,

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18:29

Dashboard: Learning From Helene and Milton

21 Hats Podcast ·

2024/10/14

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?

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55:58

When to Pull the Plug, When to Pull the Trigger

21 Hats Podcast ·

2024/10/08

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

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26:11

Dashboard: Don’t Dismiss Those Side Hustles

21 Hats Podcast ·

2024/10/07

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 found

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526 results

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