Conversations With Tyler

Help us keep the conversations going in 2026. Donate to Conversations with Tyler today. Gaurav Kapadia has deliberately avoided publicity throughout his career in investing, which makes this conversation a rare window into how he thinks. He now runs XN, a firm built around concentrated bets on a small number of companies with long holding periods. However, his education in judgment began much earlier, in a two-family house in Flushing that his parents converted into a four-family house. It was there where a young Gaurav served as de facto landlord, collecting rent and negotiating late payments at age 10. That grounding now expresses itself across an unusual range of domains: Tyler invited him on the show not just as an investor, but as someone with a rare ability to judge quality in cities, talent, art, and more with equal fluency.  Tyler and Gaurav discuss how Queens has thrived without new infrastructure, what he'd change as "dictator" of Flushing, whether Robert Moses should rise or fall in status, who'