Vasu Kulkarni's path into venture is unusual: he grew up in India listening to basketball games on the radio before school, later walked onto Penn's JV team, and built his investing style around things like emailing founders in the middle of the night just to see how they respond, along with a belief that sports works best as a quick-proof launch pad for startups rather than their final destination. He also stands out for openly saying he'd have built his first company for less money outside New York, for collecting memorabilia and independent watches as a personal passion, and for basketball stories that have become part of his personal lore, like skipping his sister's wedding for the Final Four and a podcast built around a game of HORSE with President Obama.