This episode is a post-mortem of Triangulate, a Harvard-founded dating startup that tried to match people based on their digital behavior rather than self-reported profiles — a smart idea executed in entirely the wrong order. We trace their trajectory from initial thesis through two named pivots (Wings and DateBuzz) to an honorable shutdown in 2011, and diagnose the real cause: testing solutions before validating problems. The deeper lesson is about founder psychology — the same overconfidence that gets a company started is what makes rigorous hypothesis testing so hard once momentum builds.