21 Hats Podcast

This week, in episode 183, Paul Downs, Jay Goltz, and Sarah Segal talk about sexual harassment and where you draw the line with employees. Is it sexual harassment for one employee to ask another for a date? Is it sexual harassment to ask twice? Does it make sense to have a policy of zero tolerance? Or is it better to leave room for discretion and judgment? The conversation was sparked by a recent situation Jay experienced with an employee who had been with the company for almost three decades, having started at the age of 17. “It was a very sad thing,” Jay tells us.Plus: Sarah Segal asks whether it’s better to build her business on a bunch of small clients or a smaller number of large clients. And is being CEO a health risk? We begin the episode by talking about an eye-catching story the Wall Street Journal recently published noting that an increasing number of CEOs have been dying on the job, presumably because of the heightened levels of stress. I asked the three CEOs on the episode if they’ve been taking care of themselves—but they weren’t having it. Instead of thanking me for my concern, they chided me for highlighting an article they consider complete BS. Which, of course, is what we love about these guys. They call ‘em the way they see ‘em.

This week, Shawn Busse, who soon will be boarding an Alaska Airlines plane made by the Boeing Company to attend the 21 Hats Live event in Fort Worth, finds lessons for smaller businesses in Boeing’s struggles. For one thing, there’s always danger when combining the cultures of two different companies. Plus: Shawn, whose company, Kinesis, has been a certified B corp since 2016, talks about whether the certification is losing its luster.

This week, in episode 182, Shawn Busse, Jay Goltz, and Jennifer Kerhin respond to a somewhat depressing view of business ownership offered by an investor who buys businesses for a living. That view, essentially, is that for most owners, building a business is a daily knife fight of long hours, unexpected risks, slow growth, and meager returns. In this episode, I read most of the investor’s observations to Shawn, Jay, and Jennifer, and get their reactions, which hit upon a bunch of issues that are not widely understood—including how fast growth can destroy a business, how even a profitable company can go bust, and why a good metric to assess the health of a small business might be how many people have been crying in the bathroom this year. While Shawn, Jay, and Jennifer disagree vehemently with a few of the investor’s assertions—”Kiss my ass!” says Jay in response to one—they do acknowledge that he makes a lot of good points, which leads to an obvious question: Why would anyone do this? Why would anyone subject themselves to this kind of life? As you might expect, Shawn, Jennifer, and Jay have a response to that as well.

That, at least, is what Gene Marks is planning to do. Gene tells Loren Feldman that the new rules, which are scheduled to take effect in March, would have a profound impact on many businesses, including his—if they are actually enforced. But Gene’s not convinced that’s going to happen. Before you relax, though, Gene’s even more worked up about the new guidelines coming from the EEOC regarding harassment in the workplace. Very few businesses, he says, are prepared for what’s coming. One warning: when Gene talks about regulation, his language tends to get a little salty.

This week, in episode 181, Mel Gravely, Jaci Russo, and William Vanderbloemen talk about the possibility that, after several years of the Great Resignation and the labor shortage, some owners may have given away the store. We all know the risks of not offering employees enough. What are the risks of offering too much? How do you even know when you’ve crossed the line? The owners also discuss why this might be a good time to consider acquiring other businesses. “I think this is a time to double-down,” says Mel. And Jaci explains how she and her team are reviewing everything the company does to see if AI can be employed to improve each and every process. Oh, and one last thing: How exactly, in this day and age, are business owners supposed to keep track of all of the subscriptions—and all of the subscription log-ins—that they and their employees have acquired through the years? How much money are they spending on stuff they no longer use? “Thanks a lot,” responds Mel. “I’m starting to sweat.”

This week, Gene Marks tells Loren Feldman that while he’s excited about all of the great stuff we will eventually be able to do with artificial intelligence, business owners should stay away from Copilot for now. As with a lot of Microsoft products, Gene says, you just don’t want to be an early adopter. Plus, Gene explains his not-completely-obvious fraud-prevention strategy: Make your people take vacations.

This week, in episode 180, Jay Goltz, Jennifer Kerhin, and Liz Picarazzi discuss their efforts to get a better grasp of what drives their profits. They ask how much of their finances they should manage themselves. And how much should they rely on an accountant or a fractional CFO? When does delegation become abdication? Jennifer says she’s benefitted from hiring a fractional CFO who has taken an active leadership role, including setting up a database that helps Jennifer see in real time whether the fees she’s charging cover the labor she’s deploying. “Whatever she's charging me,” says Jennifer of her CFO, “it's absolutely worth it.” Liz, meanwhile, thinks she should be doing more herself. And Jay says he was paying big bucks for a full-time CFO until late last year. “And it was a complete waste of money,” he says, which is why he’s decided not to replace her. Plus: Liz reveals her secret strategy for marketing directly to municipal government officials, some of whom have started to use the term “Citibin” generically. And the owners respond to a question from the head of a cost-reduction service who wonders why she’s struggling so much to get business owners to try her risk-free service.

Well, yes, actually, but Gene Marks and Loren Feldman discuss two questions: One, what exactly is driving the boom? And, two, are the startups substantial enough to matter? Or is this just about people losing their jobs and driving for Uber. Plus: what would you do if you owned fast food locations in California where the minimum wage for fast food workers will jump to $20 an hour in April. And what are business owners to make of the case the Supreme Court heard last week about the constitutionality of federal regulation?

In this week’s bonus episode, Cameron Madill takes us on his succession journey, which began years ago when he started having conversations with older business owners, many of whom seemed to feel trapped. They’d had a lot of success, they were proud of the business they’d built, but they weren’t sure what to do with it or how to leave it. None of the usual options seemed terribly appealing. Hoping to write a different ending, Madill, now in his 40s, started looking for better options much earlier than most owners, and the one he landed on was an unusual choice: a worker cooperative. Now, there are aspects of this model that are likely to give some owners pause. For one, a co-op probably isn’t going to produce the biggest payday for a selling owner. And if the owner wants to stick around as CEO, he or she will have to report to a board, and that board can challenge any and all of the owner’s decisions. But Madill, as he explains in a conversation we recorded late last year, before he stepped down from his role as CEO, decided to sell to his employees anyway. Not only is he glad he did, he thinks co-ops are an option far more owners, especially those struggling to find a buyer, should consider.

This week, Shawn Busse and Loren Feldman talk about some big changes coming to the world of small business. At his consulting firm, Kinesis, Shawn is already beginning to experience the impact artificial intelligence is having on his industry. He knows B2B business owners who are spending a lot of time on TikTok—and they’re not just watching dancing videos. And his client base has already shifted dramatically toward women-owned businesses.