Photo: ©Buena Vista Pictures/Courtesy Everett Collection
Curious consumers can smell trouble from a mile away. In January, fans of canned fish smelled drama at Fishwife, a premium seafood brand aimed at “girls’ dinner”-obsessed millennials. Co-founded in late 2020 by friends Becca Milstein and Caroline Goldfarb, Fishwife transforms budget pantry items into gourmet daily snacks and stocks “shop-a-shop” alongside squeeze-out olive oil bottles and artisanal dried pastas. In three years, the company has landed features in several major publications, secured an adorable summer collection with Lisa Says-Garr, and projected annual sales of $5.8 million. So it wasn’t a surprise when Milstein, CEO of Fishwife, appeared on ABC’s Shark Tank earlier this year. What happened: She pitched alone.
In a TikTok posted shortly after the episode premiered, “Where’s Caroline?” writer and trend analyst Casey Lewis wondered. Lewis did a little research and discovered that Goldfarb had unfollowed Milstein on Instagram. More importantly, Fishwife, under its legal name Shrimp Girls Inc., had sued Goldfarb in 2023 for breach of contract, trademark infringement, and more. (The suit claims the company won “despite, not because of, Caroline Goldfarb’s efforts.”) “Frankly, I don’t care what happens in their personal lives. Starting a business with friends is very stressful,” Lewis blurted out in the video. Still, she couldn’t let go of the parasocial investment she’d built in the duo and their brand. “When I eat my rainbow smoked trout for lunch today, it’s not going to taste as good because I’m too worried about what’s going on with Becca and Caroline.”
The Fishwife split is one of many famous horror stories about businesses started by close friends. Aftermaths like the firing of Great Jones, which led to mass resignations of full-time employees at an Instagram-popular cookware brand, have been the subject of media-inspired investigations. Professional altercations have been dramatized in Oscar-winning films, such as “The Social Network,” which depicts the founding of Facebook. With 65% of startups failing due to founder troubles, joining forces with someone you’re already close to may seem intuitive, but mixing business and personal life carries great risks. Noam Wasserman, then a professor at Harvard Business School, surveyed 10,000 founders of early-stage technology and life science startups and found that after collecting a decade’s worth of information from annual surveys, teams of friends were the most unstable co-founder combination. Strangers worked just as well. This result has remained consistent through ongoing research. “By 2017, [we] “The data set has doubled in size,” Wasserman told me via email, “and subsequent analysis has confirmed our initial findings.”
It’s clear why someone would want to work with a friend: they’re proven best friends who already have a trusting relationship and enjoy spending time together. From a story perspective, a typical dorm story about two like-minded buddies racking their brains to solve a shared obsession is much more romantic than one without personal contact. But friends may underestimate the stress of the business and succumb when once small and overlooked cracks in their relationship widen under pressure. The baggage of existing dynamics can cloud their judgement and prevent them from making choices that are actually in the interest of the whole. Have you seen Romy and Michelle’s high school reunion? Consider how in that quintessential BFF comedy, the fictitious Post-it business that Romy and Michelle concoct just to fool their former classmate is enough to destroy their relationship. They bicker over who gets credit for the “invention” and hurt each other with their selfishness.
Agatha Kruk, a partner at the law firm Perkins Coy, which helps startups structure and scale, agrees: “My personal view is that close friends should likely not enter into a founding relationship.” Friends who dislike awkward conversations and are convinced that their relationship is infallible may neglect to define the responsibilities and procedures necessary to prevent long-term conflict. How will money be distributed? How will key decisions be made? What happens if someone says they want to quit? It’s awkward to imagine disaster scenarios when everything seems fine, but that’s smart business. In the case of Fishwife, Milstein and Goldfarb initially did not put down in writing how the shares would be distributed. “They discussed the issue but never issued a document,” the complaint states. This became problematic because Milstein assumed most of the responsibility and Goldfarb continued his thriving career as a television scriptwriter. After Goldfarb stopped contributing work to Fishwife in 2021, they began negotiating her departure. But she was not satisfied with the terms they outlined and made demands that Fishwife called “clearly unreasonable.”
Key inflection points test cohesion. “If you’re struggling to decide whether to continue fundraising or sell the business, or if one founder isn’t successful in a particular role and needs to step into another role, those moments can create an environment of discord,” Kruk continues. A third party can sow distrust. Founders doubt the other’s intentions, hire personal lawyers, and fight each other through proxies. In 2020, the relationship between Alex Cooper and Sophia Franklin (best friends and roommates and co-creators of the women’s locker-room-talk podcast Call Her Daddy) publicly fell apart after a contract dispute with parent company Barstool Sports. Franklin was convinced the two deserved better. With the guidance of her boyfriend, an executive at HBO Sports, she pitched Call Her Daddy to other prospects. Cooper, who wanted to stay at Barstool, was tired of the back-and-forth. “When I found out that the person I thought I was in business with had people who were heavily influencing her decisions, I had to make a decision for myself and my career,” Cooper explained in a YouTube video. Cooper ended up re-signing with Barstool, leaving Franklin feeling betrayed. “I found out later, [Cooper and Dave Portnoy, the Barstool CEO] “There were connections there that I 1,000 percent didn’t know about or have been involved in,” she said.
The disagreements get even more complicated when core friendship becomes an element of a company’s brand marketing. Such is the case with Great Jones, which sells not just vibrant enameled cookware but a feel-good lifestyle based on quality time with loved ones. The company’s founders, Sierra Tishgart (a former New York editor) and Maddie Moelis, both Forbes 30 Under 30 names, boasted about a 20-year friendship forged at summer camp. They paid homage to their history by offering their flagship Dutch oven in the same vibrant green as the camp’s color.
The implicit message behind Great Jones, like any social media-friendly consumer brand, is that it’s not just a company but a community, and consumers can pay to join this happy sisterhood. (Great Jones launched Potline, a text service that lets you request personalized recipe ideas and advice as if you were calling a friend.) In a 2021 Insider expose, Anna Silman reported that Great Jones employees envisioned the company as a “platonic ideal: a utopia for smart, driven young women.” But that illusion was shattered when Tishgart overtook Morris to become the face of the brand, the two feuded over financial strategy, and employees took sides and ultimately abandoned the company. (After all this happened, Great Jones told Insider that it was doing better than ever.)
Some of the core characteristics we have come to associate with friendship, such as its fluidity and openness, feel at odds with the structure necessary to sustain a business. Although I see friendship as a force that holds my life together (and many of my friends would say the same), I have never sat down with a friend to discuss the purpose of the relationship. What would that conversation look like? The evolution happens non-verbally and improvised. We sync up, then distance ourselves, making space for each person to follow their own path. Sometimes this seems like a mature choice, but sometimes it’s just misleading. The friendship might benefit from more clarity and commitment.
But there’s hope: friend-cofounder relationships don’t always work out. When Claire Mazur and Erica Cerullo launched their bespoke retail brand Of a Kind, they had already experimented with work patterns as undergrads on the University of Chicago’s College Events Committee. As Mazur puts it, their relationship was a kind of “intellectual friendship” based on shared interests. “We never really thought, ‘Am I even allowed to do this?'” They established and differentiated responsibilities, and over time developed confidence. They sometimes struggled with disagreements, a dynamic shared by other female cofounder teams they interviewed for their book, Work Wife. Mazur and Cerullo overcame their aversion to conflict with the help of management coach Ben Michaelis, who offers “one-third therapy, one-third management coaching, one-third marriage counseling” (couples counseling is all the rage in the tech industry). The pair has worked with him for more than a decade, and are launching their third business together.
“I remember this deep reluctance to think that if the business fell apart, our friendship would fall apart,” Mazur says. At one point, they faced the possibility that Of a Kind might not survive. “We had to talk through what that meant for us. We realized that the most important thing for us was to find a way to continue working together.” With clear contractual terms and outside support, tensions might be minimized. But Quinn Heraty, founder of the Heraty Law Firm, which specializes in podcasts and media, stresses that communication is key. “If co-founders can’t have the conversations they need to have about business issues, maybe they shouldn’t be starting a business together in the first place.”
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