Never think you’ve outgrown reality checks
In 2009, Sunil Nagaraj launched Wings, a dating app that promised to rewrite the rules of digital romance. By analyzing data from Facebook, Twitter, and even Netflix, it could identify compatible matches with unprecedented accuracy.
Wings went viral. Nagaraj and his team were on the verge of something revolutionary. Or so it seemed.
But as matches rolled in, users still preferred physical attractiveness over common interests. Blinded by their initial success, Nagaraj resisted conforming to the dating landscape’s established norms. Convinced they could reshape user behavior, the team leaned harder into data-heavy matchmaking, even refusing to show photographs until compatibility had been rigorously verified. But as it turned out, the very factors that made other dating apps frustratingly basic were exactly what made them popular.
Three years after launching, Wings filed for bankruptcy. Once confident that he could “fix” the dating industry, Nagaraj had instead learned a costly lesson: Some conventions exist for a reason.
Over the past thirty years that Tom Eisenmann has taught starry-eyed founders at Harvard Business…
