Thursday, April 3, 2025

Is Your Success Distracting You from the Crimson Flags Ahead? By Philip S. Naudus, The Startup, November 2024

Never assume you’ve transcended fact-checking.

Development feels wonderful until it doesn’t.

In 2009, Sunil Nagaraj launched a pioneering courtship app that revolutionized the digital landscape of romantic relationships. With data insights gathered from Facebook, Twitter, and Netflix, the algorithm can identify compatible matches with remarkable precision.

Wings went viral. Nagaraj and his team were on the cusp of a groundbreaking innovation. Or so it appeared.

Despite the influx of new matches, customers prioritized physical appeal over engaging activities. As the allure of initial achievement clouded his judgment, Nagaraj struggled to conform to the conventional standards of the courtship landscape. Confident that their platform could influence consumer behavior, the company doubled down on its data-driven approach to matchmaking, going so far as to withhold profile photos until thorough compatibility checks were complete. While it seemed counterintuitive, the same elements that initially rendered various dating apps frustratingly basic ultimately contributed to their widespread popularity.

Three years after its launch, Wings filed for Chapter 11 bankruptcy protection. Realizing that breaking the rules of courting came at a steep price, Nagaraj learned a valuable lesson: Conventions are established for a reason.

For three decades, Professor Tom Eisenmann has mentored idealistic entrepreneurs at Harvard Business School.

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