This week, Cameron Madill, an entrepreneur who’s married to an entrepreneur, talks about the challenges of building a business while maintaining a relationship. Along with his own experience, Cameron has done lots of research, including interviewing more than 100 couples, and has also started a business to help couples balance marriage and entrepreneurship. Among other things, we discuss the difference between healthy passion for work and unhealthy passion, how to handle the most common issues that come up between entrepreneurial spouses, and the most important lessons Cameron has learned on this journey.

This week, in episode 263, we bring you another 21 Hats Brainstorm. Elan Daniel, who started a small-batch hummus business inspired by a memorable experience in Israel, is trying to figure out his best path to long-term viability. So far, he’s been selling at farmers markets and direct to consumers, making all of the hummus and all of the deliveries himself. Since February, his sales have been growing between 5 and 10 percent a week, but his growth is constrained by his refusal to use preservatives, which adds flavor but limits the product’s shelf life. So how should he proceed: Should he sell to speciality markets and restaurants? Should he try to sell to Whole Foods? Should he open his own hummus restaurant, or hummusiya? Should he try to introduce his hummus to the uninitiated or should he focus on connoisseurs? To help Elan think through his options, we convened a panel of 21 Hats Brainstormers and recorded this podcast episode. It’s brought to you by New Bridge Studios, which helps companies, creators, and causes connect their story to the bottom line. And by the way, if you have a challenge you’d like to put before a panel of business owners in our next Brainstorm, shoot me an email: [email protected].

This week, Eric Stites, founder and CEO of Franchise Business Review, talks about the state of the franchising world. How much money do you need to buy a franchise? How much can you make? What are the hot categories? What are the most common mistakes? We also talk about life on the other side: What makes a business a good candidate to become a franchisor? And is it possible to avoid the tension -- and litigation -- that so often arises between franchisees and franchisors? Plus: If you buy a franchise, are you an entrepreneur? Or are you just buying a job?

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:

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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?

In a few weeks, I’ll be in Portland, Oregon, for Shawn Busse’s always terrific Catalyst event. That trip has had me thinking about the city’s keep-it-weird ethos, the spirit that’s made Portland a hotbed for creative business building. My upcoming trip has also inspired me to revisit a podcast conversation Shawn and I recorded in early 2024 with Jenelle Etzel, who is founder of Living Room Realty. The boutique real estate agency has more than a hundred brokers and a reputation for doing things differently, but Jenelle didn’t set out to be a business owner. In fact, she majored in weaving (Shawn, for the record, majored in ceramics). She fronted a punk rock band. She lived out of a van. And yet, those experiences—especially learning how to manage people who didn’t technically have to listen to her and how to serve customers who’d been ignored by the mainstream—turned out to be perfect preparation for building a thriving business in a quirky city. It’s a story that says something about Portland, but even more about the unconventional paths that can lead to successful entrepreneurship.

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.