21 Hats Podcast

Gene addresses the big legal settlement in which Visa and MasterCard have agreed to cap the fees they charge merchants for five years. He explains both why many merchants are disappointed in the settlement and why he’s perfectly happy to pay those swipe fees when his big-ticket clients pay with a credit card. Plus: Gene discusses the new IRS tax rules you should know about and how the bankruptcy code has made Chapter 11 less of a defeat and more of a strategic tool for small businesses.

This week, in episode 189, Paul Downs, Jennifer Kerhin, and Liz Picarazzi discuss the challenges couples face when one spouse is building a business. Liz says it was important to let her husband know that she spent years working on a business plan before leaving her corporate job to start her first business. Paul explains why, when times have been tough, he hasn’t always shared the bad news with his wife. And Jennifer says too many couples planning for one spouse to start a business focus on best-case scenarios rather than the more likely worst-case scenarios. She also suggests some important questions for couples to ask themselves, including this one: “Will she still have faith in him if the business fails?” Plus: Businesses fail all the time, of course, and Paul explains why he thinks it’s usually for one of three reasons. And four years after the pandemic arrived, we take a look back: What was each owner’s toughest moment? What was their best decision? How have their business models changed?

Obviously, there’s no one-size-fits all answer to that question, but this week Shawn Busse offers up a slew of smart considerations and guidelines to help business owners come up with an answer that makes sense for them. A couple of Shawn’s points: If you haven’t done so already, spend the money getting to know your customers better. Plus: it’s important to understand why digital marketing works for some but not for others.

This week, in episode 188, we offer you a taste of the 21 Hats Live event we held in Fort Worth two weeks ago. It’s a different kind of event where there are no speakers, only participants. It’s pretty much a three-day, peer-group session for business owners, where we share challenges and insights and make connections. There were 25 of us, including most of our podcast regulars.For me, the highlight was an exercise that Chris Hutchinson of the Trebuchet Group facilitates. He calls it a “Fish Bowl” because the idea is to have an owner stand up and expose everything about a specific challenge that he or she is confronting. Fortunately, we had one owner who was gracious enough to agree to reveal all, to answer any question. And that owner was, well, it was me, actually. The truth is, this was a priceless opportunity for me to get some feedback from a focus group of smart entrepreneurs who were already familiar with 21 Hats.It even got a little emotional, mostly because a couple of the owners were kind enough to say that, had it not been for 21 Hats, their businesses might not have survived the pandemic. That was moving to hear, to say the least, but of course, that alone doesn’t mean 21 Hats has a sustainable business model. We recorded the whole thing, and if you have any thoughts after listening to it, please send them my way.Sound engineer: Blake Sessions, Content Capital.

This week, Gene Marks tells us it’s time to update your clunky old technology. There was a time when he understood why owners said they were sticking with the old stuff because it wasn’t broken and they didn’t want to endure the pain of transitioning it. But those days are over, says Gene. If you have any hope of selling your business or passing it on to the next generation, it’s time to act. Plus: Why Gene thinks most owners need to get out of their offices more. And why he opposes a ban of TikTok.

This week, in episode 187, Matt Hoying, president of Choice One Engineering, explains to Shawn Busse and Jay Goltz how he created a DIY employee-ownership plan for his firm. Some 10 years ago, Matt’s predecessor as president tasked him with selecting an ownership structure that would engage employees and help Choice One be as successful as possible. That sent Matt on a mission of discovery in which he researched the pluses and minuses of every structure he could find—including employee stock ownership plans—before ultimately creating his own structure. Matt’s plan doesn’t enjoy the tax advantages of an ESOP, but it’s open even to part-timers, and it requires employees who want to be owners to make a financial investment in the business. In other words, they aren’t given ownership; they have to buy into it. Shawn and Jay quiz Matt on the choices he made and how the plan has worked out.

This week, the founder and CEO of Small Business Majority talks about whether he heard what he wanted to hear in Joe Biden’s State of the Union address, what he makes of recent court rulings asserting that the Minority Business Development Agency must support owners of all races, and what he makes of the growing demand from businesses for more immigration.

This week, in episode 186, Shawn Busse and Laura Zander discuss what exactly Laura’s job should be. She’s CEO, of course, and she’s been focused on acquisitions and growing the business, but she’s never really found someone to take over the big role she used to play, which leads to these questions: Should she go back to being her own chief marketing officer? Or does she need to go out and spend real money to hire one? And then, toward the end of the conversation, Laura actually devises a plan on the spot to sell yarn in a surprising and creative way, which perhaps answers the very question we’d been discussing. Plus: Shawn explains how having the right partner can make or break a business as he celebrates having made his final payout to his own former partner.

This week, Gene Marks offers to boldly go where no business owner has gone before. Few of us need to be convinced that artificial intelligence will be transformational, but even fewer of us have the time, energy, and capability to keep checking on which AI apps and platforms are worth using right now. Which is why Gene Marks has given himself precisely that assignment. This week, Gene reports back on what he found when he explored OpenAI’s GPT store for business owners. Did he find lots of useful stuff? Actually, what he saw reminded him of the iPhone app store (circa 2007). Plus: Gene also explains why divorce can be especially nightmarish for business owners and what they can do to prepare for and ease the pain.

This week, in episode 185, Jay Goltz, Jaci Russo, and Sarah Segal talk about whether it’s finally time for Jay to enter the brave new world of task-management software. That’s, in fact, what his two kids in the business are encouraging him to do. As it happens, Jaci and Sarah have tried most of the project-management tools out there—Monday, Basecamp, Asana—and they kind of love them, but with one caveat: They can be a lot of work. Which is all Jay needed to hear. After that, we talk about the challenges of managing credit cards and points, and Jay explains why, after 40 years, American Express is no longer what’s in his wallet. Plus: the owners tackle a question posed by an entrepreneur with a very new startup: “When does the anxiety of a new business subside?” asks the newbie, which prompts some laughter and this answer: The anxiety subsides in the 42nd year, says Jay, who’s been running his business for 42 years.