Underrated & Weird Parts of New York

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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's the most underrated NYC mayor, what's needed to attract better mayoral candidates, the weirdest place in NYC, why he initially turned down opportunities in investment banking for consulting, bonding with Rishi Sunak over railroads, XN's investment philosophy, maintaining founder energy in investment firms and how he hires to prevent complacency, AI's impact on investing, the differences between New York and London finance, the most common fundraising mistake art museums make, why he collects only American artists within 20 years of his own age, what makes Kara Walker and Rashid Johnson and Salman Toor special, whether buying art makes you a better investor, his new magazine Totei celebrating craft and craftsmanship, and much more.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded October 8th, 2025.

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Timestamps

00:00:00 - Intro

00:01:32 - Queens and NYC's geography

00:08:36 - New York City mayors and electoral politics

00:13:22 - Building a career in investing

00:18:50 - XN's investment philosophy

00:24:35 - Maintaining founder energy in investment firms

00:30:45 - The sociology of finance in NYC, London, and UAE

00:32:21 - How AI is reshaping investing

00:36:53 - Museum operations

00:42:21 - Favorite artists

00:50:39 - Tastes in art and how the canon will evolve

00:57:22 - Totei, a new venture