21 Hats Podcast

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.

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.

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.

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.

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 suggestions. And while Shawn hasn’t tried EOS in his own business, he has seen how it works in lots of client businesses. As a result, all three have strong opinions about what types of owners and what types of businesses are likely to do best with EOS. Laura, for example, tells us: “I think it's helpful for people like me 10 years ago, who just don't know what they're doing.”

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.

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 discuss what makes a business a good candidate for trust ownership. The issues we address include: Is this only for businesses that have a save-the-world type of purpose? How much does it cost to create an ownership trust? Can owners sell to a trust and still run the business as they wish? And perhaps the biggest question of all: What can go wrong?

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.

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 Company. “My dad and my uncle told me I was nuts,” says Jeff, but he made them an offer they couldn’t refuse. He would put the family’s snacks online—this was way back in the early dotcom days—and they wouldn’t have to pay him unless he actually sold some nuts. As it turned out, Jeff’s little internet play wound up unleashing explosive growth and consumed the business. And despite being a former investment banker, he managed to do that without taking any outside capital. Since we first published this episode Jeff has promoted himself from Chief Nut to Chair Nut.

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 offending customers and forfeiting profits. Plus: We follow up on some issues we’ve discussed in previous episodes. Jay told us recently that he’s cutting back on his advertising spend. Is that the best response to a softening market? Jennifer told us when she first joined the podcast about her long march through what is often called the valley of death. Is she still in the valley of death? And Jaci told us at the beginning of the year that she had two big clients that were ready to sign on. Did they in fact sign on?