21 Hats Podcast

This week, in episode 165, Paul Downs, Jay Goltz, and Laura Zander don’t hold back. Laura and Jay both say their sales are coming in well below expectations. Not surprisingly, Jay has a five-point checklist that he’s using to assess and address his shortfall. Laura’s situation involves a marketing team that she says has been feeling stressed and is coming apart, with lots of crying and arguing. “They’re just collapsing,” she tells us. Paul, meanwhile, says his sales aren’t bad, but he’s got one employee who’s been holding them back. The employee, who’s been with Paul for 10 years, has been spiraling of late, says Paul, who’s dreading what he calls “the toughest conversation,” a conversation he fears will leave the employee devastated. In such situations, Jay says, he’s found it helpful to rank himself from one to 10 on the hardass scale: If Mr. Rogers is a 1 and Jack Welch—the take-no-prisoners former CEO of GE—is a 10, where do you want to be? “If you pick four or five,” Jay says, “you're probably gonna go out of business.”

Gene Marks tells Loren Feldman that by almost any measure the economy continues to perform quite well. And yet, business owners don’t seem to believe it. Why is that? Gene says owners have some cause for concern. In fact, he expects a slight recession or slowdown in the next three to six months—of course he’s been saying that for more than a year now. “One of these days,” he says, “I’m going to be right.” Plus: Gene highlights two significant tax credits that most business owners don’t know about.

This week, in episode 164, Shawn Busse and Jay Goltz discuss a recent Business Journal report that a lot of business owners are feeling burned out. Why is that, and what can owners do to avoid it? And have either Shawn or Jay been there? Plus: Shawn brings us up to date on the leadership transition he’s initiated, and—believe it or not—Jay has had another revelation about ESOPs. Also, do business owners need better regulation or no regulation? And which regulations are annoying Shawn and Jay the most right now? For Shawn, it’s the nightmare of having employees in multiple states and having to figure out and comply with the various rules of each of those states.Show Notes:You can learn more about Shawn Busse’s September event Catalyst.Here’s the Business Journal article about business owner burnout.Here’s the podcast where Phil Hayes offers a fresh perspective on what it takes to do an ESOP.Here’s the conversation where Jim Kalb talked about his own ESOP.Here’s the most recent Dashboard conversation where I talk about regulation with Gene Marks.

This week, Gene Marks and Loren Feldman agree that artificial intelligence is becoming the biggest story in small business, with Gene highlighting a slew of AI tools that business owners can put to use right now. Gene also issues a warning that owners who do not start paying attention are taking a much bigger risk than they may realize. Plus: Gene also talks about team-building platforms that can help owners engage their employees, especially those working some or all of the time from home.

This week, in episode 163, Liz Picarazzi, Jennifer Kerhin, and Sarah Segal talk about whether they ever wish they could go back to their corporate lives. For Liz, there was a period during the early days of COVID. For Jennifer, it was when she made the transition from a consulting business to an employee business. These days, none of them can imagine going back—although Sarah did have a rough week recently when she lost two clients. “It's just the way of the world,” she tells us. “When businesses are looking to cut costs, it’s outside agencies that go first. But when it's two of your largest clients in the span of a week, it's like, ‘Really? Can I go dig a hole, put myself in it, and just stay there forever?’” What she’s actually doing, as we discuss, is figuring out some new ways to attract more clients. We also discuss whether everyone needs a business plan and whether the three owners ever wonder if someone else would do a better job running their businesses.

Yes, it’s August, but Tracy Bech — co-author of “60 Minute CFO” — tells Loren Feldman it’s not too late to assess where your business stands and take steps to hit your numbers. Tracy also talks about what prompted her to take her own financials seriously, what owners can do if their revenue isn’t meeting expectations, and why she kind of likes recessions but isn’t disappointed we haven’t had one.

This week, in episode 162, Jay Goltz tells us that, on second thought, he did learn something important watching HBO’s Succession. He still wants to work as long as he can—even if that means dying at his desk—but he now realizes, thanks in part to Logan Roy, that he needs to put a plan in place in case he were to get hit by that proverbial bus. This realization was also furthered by hearing the story of a 51-year-old entrepreneur who died in his sleep recently, leaving his wife to figure out how to keep their bank from calling its loans. As part of his hit-by-a-bus plan, Jay says he’s crossing streets very carefully, but also considering creating a board of advisors that will be able to offer advice to his survivors. But that’s a little tricky because, as you may have noticed, Jay’s not exactly a board-of-advisors kind of guy.

This week, Gene Marks tells Loren Feldman that the Silicon Valley notion that startups are threatened with extinction is ridiculous. In fact, new business openings have been surging. The real problem in Silicon Valley is the venture-backed business model. Plus: Gene also talks about a way for small businesses to help their employees get health insurance without having to actually offer health insurance. And Gene also tells us about a lesson in regulation he learned from an eight-year-old entrepreneur.

This week, in episode 161, Shawn Busse tells Jay Goltz and Jennifer Kerhin that he’s realized that his business, too—like Jennifer’s—is stuck in the valley of death that we first discussed a couple of episodes ago. Shawn’s realization prompts a discussion of what it takes to cross the desert and get out of the valley. We also have a surprisingly entertaining and enlightening conversation about insurance that makes clear why you should occasionally review what policies you have and why you have them. “I have something called directors insurance,” says Jennifer, “and I don't really even know what that is.” Shawn notes that he found a company that helped him reassess several of his insurance lines. “What I like about that,” he told us, “is that while insurance brokers are incentivized to oversell you, because they make commissions,” this company sells its expertise and not policies. Plus: we start the episode with Jay explaining why binge-watching HBO’s Succession brought back all of his worst nightmares about owning a family business.

This week, Gene Marks tells Loren Feldman that it’s hard enough trying to run a small business in 2023, but just try running one in a blue state, where he says businesses have been subjected to a tsunami of regulation mandating things like paid time off and safe working conditions. Gene also talks about what’s going to happen to all of that unused commercial office space and whether there’s any reason for businesses to try out the new Twitter clone, Threads.