Episodes
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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 since then. For 40 years, A.R.E. grew slowly but steadily on word of mouth. More recently, however, the Elbert family has concluded that it’s time to do some real marketing. Like a lot of owners, though, they’re a little overwhelmed by the options, unsure where to begin, and wary of wasting money. They also happen to be going through a family ownership transition. The 21 Hats brainstormers begin by asking a lot of questions, including whether the owners have invested in search engine optimization, whether they’ve gone back to some of the customers they lost to China, and whether they’ve considered hiring a marketing agency.
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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 jurisdictions looking to cut red tape. As always, Victor brings news that has yet to reach most of us—including an issue he plans to address in 2025: standard lending rules that actually discriminate against entrepreneurs by making it harder for them to get a home mortgage.
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Missing episodes?
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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 words, “an affirmative action baby” and that that investment had paid off for his college, his previous employers, and the city of Cincinnati. It’s been less than four years since Mel published Dear White Friend, but of course that was a very different time. This week, he talks about the backlash that has ensued and the strategies he still believes can work for those who don’t consider diversity a dirty word.
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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 owners do now to prepare? “Beat up your vendors,” says Gene. “And clean up your data.”
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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 think—for those of you keeping score at home—we actually hit 11. Which led Jay to caution: “I by no means am telling anybody, ‘Oh my God, I don't sleep at night. I'm worried about all these things.’ I'm not worried about them. I just keep an eye on them.” Wait, says Paul. That’s another one: “The risk is that you let this thing live in your head and that it destroys your ability to focus on what you should focus on.” Okay, so that makes 12. And by all means, please let us know which ones we missed.
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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 benefit from reallocating how you distribute the earnings. And of course, pay those estimated taxes on time.
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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 something more meaningful to do with his life. That extended search led him, somewhat improbably, to overseeing sales for a company that manufactured specialty vehicles, including the Oscar Mayer Wienermobile. It was there that Travis had another life-changing experience when a nurse with a federal grant asked if he could build a mobile clinic to reach patients in underserved communities. That was the spark that led Travis and Amanda to cash in their insurance policies and start Mission Mobile Medical in 2020. The company, whose remanufacturing process allows it to create clinics in less time and for less money than its competitors, expects to hit $60 million in revenue this year.
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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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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 and figuring things out. So when I thought about that—small team, high stakes, self-sustained—small business kind of fit that bill.” Not surprisingly, it took Rich some time to figure out what he was doing with the plumbing business, but in just four years, through organic growth and a few acquisitions—while taking no outside capital—he’s gone from three plumbers and $1 million in annual revenue to about 90 employees and $20 million in revenue. Which is why, Rich tells Jay and Shawn, he keeps moving the goalposts, reassessing just how big he wants the business to be.
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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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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 proceed with their ongoing migration to Shopify. “Our sales are going to go down,” says Laura. “SEO is going to be rough. My biggest concern, honestly, is Doug's mental health. This whole process has been so stressful for him.” Shawn, Jay, and Laura also discuss how they feel about the possibility that the 20-percent Qualified Business Income deduction could go away next year, when it’s set to expire. You might be surprised by their answers.
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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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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, but specifically those that help him figure out whether a candidate is likely to work well with others. Plus: Shawn talks about what it was like attending the recent going-out-of-business sale of a company he had declined to take on as a client three separate times. Also, Shawn and Jay respond to a Reddit post, where a business owner asks what he can do about a large commercial client who simply refuses to pay a $40,000 bill. “Did I just learn a $40,000 lesson?” the devastated owner asks. “What now?”
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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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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 outsiders have more experience but aren’t as good a fit? And that leads to a discussion of how to decide when to press on with a venture that’s struggling—and when to give up on it. Not surprisingly, all three owners have some experience in this area. Of course, they also have experience with deciding when to start a business, but they have very different attitudes about risk. While Mel says he’s pretty much always ready to go, Jennifer tells us she’s been noodling on an idea she really wants to pursue for about five years.
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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 a whole bunch of people who are working together to build things. It’s a refreshing perspective.
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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 Waldrop furniture business that her parents own. As you’ll hear, BaLeigh has some real concerns: the business has been down of late, it’s predominantly brick-and-mortar, and she would have to work out an ownership structure with a younger brother. The 21 Hats brainstormers ask a lot of good questions, including whether the business is profitable, whether it’s been paying family members a market wage, and whether it owns the real estate. They also offer a lot of smart suggestions. Plus: it all ends with a very surprising offer from Jay Goltz.
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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 develop a plan for how they would spend it. “This is not going to end well,” says Ami.
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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 decision makers her agency targets. And the three owners respond to a case study in ADA-compliance litigation taken from a Reddit post: “What are we supposed to do about this?” a business owner who has been sued for having a non-compliant website writes in the post. “I am trying not to overreact, but having my savings and my income taken from me this way is just devastating.” Jaci, whose agency builds websites, says there is a way to protect against those lawsuits.
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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 advice that start with creating a culture that people want to be part of and then building your brand as an employer. We also talk about how he’s gotten his whole team hooked on using AI, in part through what he calls show-and-tell days.
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