21 Hats Podcast

This week, Jaci Russo and Sarah Segal wrestle with a question that haunts many entrepreneurs: How do you bring your kids into the business—whether for a summer or for good—without messing up the business (or the kids)? For years, Jaci and her husband Michael quietly hoped their son Jackson might one day take over their marketing agency. Their unusual strategy? Never mention it to him—at least not until he’d demonstrated interest and not until he’d proven himself somewhere else. The approach seems to have worked: Jackson has joined BrandRusso, and Jaci has told him he’ll take over in four years. Which prompted Sarah to ask Jaci an obvious question, “What happens if he takes over, and he does a bad job?” As it happens, Jaci and Michael have thought about that, too. Plus: Jaci and Sarah discuss the merits of the new tech trend, especially hot in San Francisco, where more and more people are wearing AI-powered devices that can stealthily transcribe every conversation they have.

This week, Shawn Busse, founder of Kinesis, talks about finding ways to market authentically when so many of the standard tools of marketing are in flux. In Shawn’s case, that means holding an annual event where business owners -- and potential clients -- have the opportunity to come together to learn and interact in person. Of course, throwing such an event costs money. It’s a lot of work. And it’s not always easy to strike the right balance between education and promotion, but Shawn believes more businesses should try it.

A few months ago, John Abrams—author of From Founder to Future—joined us to talk about succession strategies and the different ways business owners can share ownership with employees. For his own business, John chose one of the more radical options: he turned his construction firm into a worker cooperative. Perhaps surprisingly, the more he described the co-op model, the more intrigued Jay Goltz became—although, predictably, Jay did retain a degree of skepticism. So we asked John to come back on the podcast to help Jay dig a little deeper: Are co-ops really all about democracy? Does someone on the loading dock get the same vote as the CEO? How do profits get split in the co-op model? How do losses get absorbed? How are loans secured without burdening frontline workers with personal guarantees? And perhaps most important: What can go wrong? In the end, I think surprising even himself, Jay failed to identify any real dealbreakers.Show Notes:Get a free trial of the Morning Report.Learn more about the Cooperative Fund of the Northeast.This is the podcast episode where Jay Goltz talks about how to do a We-SOP.

This week, Gene Marks makes a surprising claim: his business is “unsellable.” Never mind that it’s profitable. Never mind that it gave him the freedom to live the life he wanted and that it has left him and his wife financially secure for retirement. According to Gene, the business can’t be sold because it’s too dependent on him and because it has no IP, no exclusivity, and no moat. But is he right? Aren’t those the same challenges faced, for example, by countless HVAC and plumbing companies that private equity firms buy every day? Couldn’t Gene make his business sellable if he wanted to? What do you think? Is Gene leaving money on the table? Or has he just chosen the path that’s right for him and for his family?

Join Jenelle Etzel, a former punk rocker turned CEO of Living Room Realty, and Shawn Busse, CEO of Kinesis, as they explore the unusual paths to entrepreneurship. Jenelle shares her journey from living in a van to leading a successful real estate agency, emphasizing the importance of community and storytelling in building a brand. They discuss how creative backgrounds can enhance business strategies and tackle current real estate challenges. This engaging conversation is a tribute to the power of unconventional experiences in driving successful enterprises.

It was around Memorial Day in 2022 when Coca Cola stunned the beverage world by announcing it was shutting down production of Honest Tea. No one was more surprised than Seth Goldman, who had co-founded the brand and sold it to Coke. But within two weeks, he’d decided to do it all again, and by that Labor Day, bottles of his new venture, Just Ice Tea, were already landing on store shelves. And now, three years later, Just Ice Tea has exploded from $1 million in annual revenue to nearly $24 million to rank 88th on the latest Inc. 5000—more than two decades after Honest Tea first appeared on the list. Which makes this the perfect moment to revisit the conversation I recorded with Seth right before Just Ice Tea launched. In it, he shares how he processed Coke’s decision, why he sold to Coke in the first place, what compelled him to get back into the business, and what he learned working inside the world’s largest beverage company. And yes, I asked whether he could imagine selling this brand to Coke, too.

This week, Jimmy Kalb tells us how he built his electrical component business and, perhaps even more impressively, how he put a plan in place that has allowed him to walk away from his CEO role at the relatively young age of 63. One key: Jimmy has long been a process guy. For years, he’s been creating processes and handing them over to someone else to manage -- until he left himself with not all that much to do. Another factor: He only hires people right out of school, which is why his successor is in his early 30s and has never worked anywhere else.

This week, in episode 260, Liz Picarazzi tells Jay Goltz and William Vanderbloemen that she’s had a couple of big breakthroughs. For Liz, it’s been a challenging few years dealing with the tariffs while also trying to break into a promising new market. Despite the advice of some very smart people who encouraged her to conquer her first market —urban areas plagued by rats—before expanding into additional markets, Liz has spent several years trying to position Citibin to serve towns, parks, and resorts that need trash bins strong enough to withstand bears. For that investment to pay off, however, Liz would have to outsmart her nemesis, an especially ferocious competitor that goes by the name of Seeley. Plus: Jay talks about the plight of small retailers trying to survive while their industry collapses around them. And William tells us how he’s trying to keep up in the AI arms race between employers and employees.

Gene Marks, a seasoned CPA and writer for The Guardian, shares his insights on the struggles small business owners face with Google’s advertising monopoly. He discusses the potential of AI to disrupt this dominance, highlighting how tools like ChatGPT can reshape discoverability. Marks advocates for using YouTube as a more effective platform for promotion, emphasizing advantages like targeted advertising and tutorial videos. He also touches on professionalism in handling layoffs and the discomfort of sharing personal experiences in the digital age.

This week, in episode 259, Jaci Russo tells David C. Barnett and Kate Morgan how the hiring of her agency’s first top-level sales person went wrong. About four months ago, when Jaci first told us about this big step, she sounded thrilled. She said her new sales chief was a delight to be around, had hit the ground running, and had already lined up at least one impressive client. Unfortunately, none of that panned out. But Jaci, who is hardly the first business owner to have an important placement go off the rails, offered to walk us through her process to see what lessons we can all learn: Were the interviews flawed? Was the onboarding effort insufficient? Was it the executive recruiting firm she used? Was it the compensation structure? Or was it the remote-work arrangement? Plus: We also discuss the mounting evidence that companies have stopped filling entry-level positions. And should that trend continue, where will owners find the next generation of leaders?