21 Hats Podcast

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 current business challenges as a matter of triage. He also says that if he could write a check for $200,000 and solve his technology problems, he would do it in a heartbeat. Any takers out there?

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.

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 it can provide a sales path even for owners who have never managed to extricate themselves from their day-to-day operations. And in this week’s episode, we take you through an example of how it can work. Jay introduces us to Jill and Paul Choma, co-owners of a business, Gilded Moon Framing, that Jay recently guided through the We-SOP process. As you’ll hear, all three believe that what has worked—at least so far—for Jill and Paul could also work for many other business owners.

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 treats themselves so badly. Electrician, CPA, Realtor, hairdresser, nail salon tech, everybody else has some semblance of something to say, ‘I am a legit entity.’ Except our industry.” Which is part of the reason, Jaci says, that the constant refrain she hears from frustrated business owners who hire agencies is, “We paid them all this money. And we got nothing for it.” Plus: how do owners get past that feeling that they need to be the hardest worker in the office, the first one in and the last one out?

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 so far it’s mostly big businesses that are reaping the benefits.

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 advisors can play in helping an owner build a business. While Mel has said he wouldn’t run a lemonade stand without a board, Liz and Jay—like most business owners—have taken a different approach. The notion of having a board of advisors, Jay tells us, is something he struggles to get his head around. “I’ve been doing this for 45 years,” he says, “and I’ve never had anybody to answer to.” Plus: with the talk of tariffs getting louder, Liz updates us on her search for an alternative to manufacturing her trash enclosures in China. “We really have to have a Plan B,” she says. “We'd be stupid not to have a Plan B.”

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?

This week, in episode 194, Shawn Busse, Jay Goltz, and Jaci Russo talk about the new rules that may—or may not—ban non-compete clauses, increase the number of employees who must be paid overtime, and eliminate TikTok in the U.S. How much would those changes matter to each of their businesses? What might the owners do differently? Do the changes make sense? And why does it so often seem as if it’s small businesses that get caught in the cross-fire when the government tries to rein in abusive big businesses? On the question of non-competes, Shawn says he thinks they are often used by lazy businesses that haven’t done the real work of building loyalty with employees and customers. Plus: Do Shawn, Jay, and Jaci ever regret starting a business? Have there been times when they’ve thought about packing it in and trying something else? And also, are the terms “business owner” and “entrepreneur” interchangeable? Or do they carry different connotations? Might there be a better term? Jay thinks there is.

This week, Shawn Busse talks about his belief that, for all kinds of understandable reasons, business owners have been fixated on marketing tactics that amount to a losing battle of digital trench warfare. Over time, he says, those tactics have come to cost more and return less. But there are alternatives, and Shawn takes us through some examples. Plus: Are there lessons for smaller businesses in Walmart’s decision to place a big bet on a premium line of food.

The wrong way to make innovation happen, Ty Hagler says in this week’s special bonus episode, is to have a great idea and then go all-in trying to create it. That, he says, is a really expensive way to find out if your idea works. The right way to pursue innovation, he says, is to take your idea to customers so you can assess the pain points and opportunity spaces before proceeding. Hagler, who is founder and CEO of Trig, an innovation and design firm in North Carolina, also says he’s learned that the problem with focus groups is that the more people you have in the room, the less valuable the conversation tends to be. In fact, he says, one-on-one is best. He also says that brainstorming remotely can actually work better than in-person. Oh, and by the way, if your Mom tells you she loves your idea and will definitely buy your product as soon as it’s available, she’s probably lying.