Will Going Into Business Together Destroy Our Friendship?
Nosy consumers can smell trouble from a mile away. In January, tinned-fish fans caught a whiff of drama at Fishwife, the premier seafood brand for “girl dinner”–obsessed millennials. Co-founded by friends Becca Millstein and Caroline Goldfarb in late 2020, Fishwife had transformed a low-budget pantry item into the gourmand’s snack du jour, stocking “shoppy shops” along squeezable olive-oil bottles and dried artisanal pasta. In three years, the company had secured spreads in several major publications, an adorable summer collection with Lisa Says Gah, and a projected $5.8 million in annual sales. So it was no surprise when Millstein, Fishwife’s CEO, appeared on ABC’s Shark Tank early this year. What was: She pitched alone.
“Where’s Caroline?” writer and trend analyst Casey Lewis wondered in a TikTok posted shortly after the episode’s premiere. Lewis did some minor sleuthing and discovered that Goldfarb had unfollowed Millstein on Instagram. More significantly, Fishwife, under its legal name Shrimp Girls Inc., had sued Goldfarb in 2023 for breach of contract, trademark infringement, and more. (The company succeeded “not because of Caroline Goldfarb’s efforts, but in spite of them,” the lawsuit alleges.) “Frankly, it’s none of my business what goes on in their personal lives. It’s very stressful to start a business with your friend,” Lewis hedged in her video. Still, she couldn’t abandon the parasocial investment she’d developed with 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 going to be so worried about what’s going on with Becca and Caroline.”
The Fishwife split is one of many high-profile horror stories about businesses launched by good friends. Fallouts like the Great Jones ouster, which led the Instagram-friendly cookware brand’s full-time employees to resign en masse, have been the subject of buzzy media investigations. Professional quarrels have been dramatized in Oscar-winning films like The Social Network, about the founding of Facebook. Sixty-five percent of start-ups fail because of founder troubles, and while it may seem intuitive to join forces with someone you’re already close with, mixing the business and personal comes at great risk. After studying 10,000 founders from early-stage tech and life-science start-ups, gathering a decade’s worth of information from annual surveys, Noam Wasserman, then a professor at Harvard Business School, found that friend teams were the most precarious co-founder pairing. Even strangers were better off. This outcome has stayed consistent through continued research. “By 2017 [we] had doubled the size of the dataset,” Wasserman told me via email. “The subsequent analyses reinforced the early results.”
It’s clear why someone might want to work with a pal: They’re a tried-and-tested confidante with whom you’ve already established trust and enjoy spending time. From a narrative perspective, the classic dorm-room story of two scrappy mates putting their heads together to problem-solve a mutual obsession is far more romantic than one without that personal touch. But friends might underestimate the stress of enterprise, buckling as once minor, overlookable cracks in their relationship magnify under pressure. The baggage from preexisting dynamics might cloud their judgment, preventing them from choosing what’s actually in their collective best interest. Have you seen Romy and Michele’s High School Reunion? Consider, in that quintessential BFF comedy, how the hypothetical Post-it venture Romy and Michele make up solely to deceive their former classmates is enough to implode their relationship. The duo squabble over credit for their “invention,” wounding each other with their selfishness.
Agatha Kluk, a partner at Perkins Coie LLP who helps emerging businesses structure and scale, echoes, “My personal view is that more likely than not, close friends should not be in founding relationships.” Friends, averse to awkward conversations and convinced of their relationship’s infallibility, may skimp on defining responsibilities and procedures necessary to prevent protracted conflict. How is money allocated? How are crucial decisions made? What happens if someone wants to quit? It’s awkward to envision disaster scenarios when everything seems hunky-dory, but that’s smart business. In the case of Fishwife, Millstein and Goldfarb initially neglected to commit to paper how they wanted to distribute equity: “While they talked through the issue … they never issued documentation,” the lawsuit states. This became a problem as Millstein assumed the bulk of responsibilities while Goldfarb continued her thriving TV-writing career. After Goldfarb stopped contributing work to Fishwife in 2021, they began negotiating her exit. But she became dissatisfied by terms they sketched out, issuing demands that Fishwife called “patently absurd.”
Critical inflection points test unity. “If you’re having a tough time deciding whether to continue to capital-raise or sell the business, or one of the founders needs to step into a different role because they’re not successful in that particular role, those are the moments that can create the environment for discord,” Kluk continues. Third parties can sow distrust; suspicious of their counterpart’s intentions, founders hire their own personal lawyers and battle each other through surrogates. In 2020, the relationship between Alex Cooper and Sofia Franklyn — best friends, roommates, and co-creators of the female locker-room-talk podcast Call Her Daddy — publicly unraveled after a contract dispute with their parent company, Barstool Sports. Franklyn was convinced the duo deserved more. At the guidance of her boyfriend, an HBO Sports executive, she shopped Call Her Daddy around to other prospects. Cooper, who wanted to stay with Barstool, tired of the back-and-forth: “When I saw that the person that I thought I was in business with had a posse of people that significantly affect her decision-making, I had to make a decision for myself and my own career,” Cooper explained in a YouTube video. Cooper ended up re-signing with Barstool, leaving Franklyn feeling betrayed. “I found out later [Cooper and Dave Portnoy, the Barstool CEO] 1,000 percent had this relationship that I wasn’t aware of and not a part of,” she said.
Disagreements are further complicated when the central friendship factors into the brand marketing of the company. That was the case with Great Jones, which sold not only vibrant, enamel-coated cookware but a cozy lifestyle built upon quality time with loved ones. The company’s Forbes’s “30 Under 30”–winning founders, Sierra Tishgart (a former New York editor) and Maddy Moelis, touted a 20-year friendship forged at sleepaway camp. They paid tribute to their personal history by offering their flagship Dutch ovens in the same vivid green as the camp’s color.
The implicit messaging behind Great Jones, as with other social-media-friendly, consumer-facing brands, is that it was not just a company but a community — and that consumers could purchase their way into this happy sisterhood. (Great Jones launched a text service, “Potline,” where people could request personalized recipe ideas and advice, as if paging a friend.) In a 2021 Insider exposé, Anna Silman reported that Great Jones’s employees envisioned the company as “the platonic ideal of a utopia of smart, driven young women.” But that illusion was demolished as Tishgart edged out Moelis as the face of the brand, the two clashed over financial strategy, and employees took sides, eventually abandoning ship. (After all this went down, Great Jones told Insider it was doing better than ever.)
Some of the core attributes we’ve come to associate with friendship, like its fluidity and openness, feel antithetical to the structure necessary to maintain a business. Though I consider friendship the organizing force of my life — and many of my friends would say the same — I cannot recall a single time I’ve sat down with a friend to discuss intentions for our relationship. What would that conversation even look like? Evolutions occur wordlessly, improvisationally; we synchronize and then distance, creating space for each person to journey out on their own. Sometimes this seems like the mature option, while other times it’s just a recipe for miscommunication. Maybe our friendships could benefit from more definition and commitment.
There is hope, though. Not every friend co-founder relationship goes poorly. When Claire Mazur and Erica Cerulo started the bespoke retail brand Of a Kind, they’d already tested out their working dynamic as undergraduates on the University of Chicago’s college events board. Theirs was a sort of “intellectual friendship,” as Mazur describes it, founded on mutual interests. “There was truly never a consideration of like, Are we right to do this with each other?” They established and demarcated responsibilities, developing confidence over time. Sometimes they struggled to disagree, a common dynamic among other female co-founder teams they interviewed for their book Work Wife. Mazur and Cerulo overcame their conflict aversion with the assistance of a management coach, Ben Michaelis, who offers “one-third therapy, one-third management coaching, and one-third marriage counseling.” (Couples counseling has become fashionable in tech.) They’ve been working with him for over a decade and are working on their third business together.
“I remember a profound counterpoint to the idea that if the business goes under, will it destroy our friendship,” Mazur says. At a certain point, they did confront the possibility that Of a Kind might not survive. “We had to have the talk of, What does that mean for us? We had the realization that the thing that was most important to us was figuring out a way to continue to work together.” Clear contract terms and outside assistance might minimize tension. But Quinn Heraty, founder of Heraty Law who specializes in podcasts and media, stresses that communication is the bottom line: “If co-founders can’t have the conversations that need to be had around business issues, then maybe they shouldn’t be going into business together in the first place.”
Related