Illustrations: Xavier Lalanne-Tauzia

The Insider Guide to Avoiding a Co-founder Breakup

The complicated art of finding your professional soulmate finally has a roadmap

Courtney Rubin
Published in
12 min readOct 16, 2019

TThe screaming match was so loud you could hear it from the conference room two offices away. Drybar CEO John Heffner was trying to close a multi-million deal with investors, but he had to embarrassingly extract himself from the meeting, walk over to his co-founders’ shared office, and ask them to hush.

The inspiration for the epic fight? Red wine.

Let’s be clear: No one was drunk. It was 2016 and Alli Webb, a co-founder of blowdry chain Drybar, was furious when she learned that the then-seven-year-old company’s new Las Vegas location — its 63rd outpost, and its first with a full bar — would offer red wine. She had specifically banned it from her other locations for one very good reason: It was too messy. Her older brother and co-founder Michael Landau, who tended to defer to his sister on all things creative and hair-related (he’s bald), didn’t understand the fuss. It’s a full bar, of course it has red wine, he thought.

“Somebody has to have the final word, and it’s mine,” yelled Landau, a former corporate marketer. Eventually Webb backed down. But even as her brother describes the incident some three years later, she can’t help but interject: “Let’s add to that story that the red wine went in, and it never sold.”

The red wine fracas was a rare moment of discord for the siblings, who have since managed to build a business with $100 million in revenue that’s on track to hit 150 locations by the end of the year. But the argument triggered some baggage — sibling baggage — dating back to when the pair ran clothing boutiques together in South Florida some 20 years earlier. They fought so often and so bruisingly that when they first announced they were teaming up again to start Drybar, their parents responded: “You guys are out of your fucking minds.”

Whether co-founders are bound by blood like Webb and Landau or thrown together by matchmaking VCs, co-founder relationships are incredibly high stakes. Co-founder conflict is responsible for the failure of 65% of startups, says Harvard Business School professor Noam Wasserman, in his book, The Founder’s Dilemma. Oftentimes each co-founder…