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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

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Dan Wang argues that China is a nation of engineers while America is a nation of lawyers, and this distinction explains everything from subway construction to pandemic response to why Chinese citizens will never have yards with dogs. His prescription: America should become 20% more engineering-minded to fix its broken infrastructure, while China needs to be 50% more lawyerly so the Communist Party can stop strangling individual rights and the creative impulses of its people. But would a more lawyerly China constrain state power, or just create new tools for oppression? And aren't the American suburbs actually sterling achievements where the infrastructure works quite well?

Tyler and Dan debate whether American infrastructure is actually broken or just differently optimized, why health care spending should reach 35% of GDP, how lawyerly influences shaped East Asian development differently than China, China's lack of a liberal tradition and why it won't democratize like South Korea or Taiwan did, its economic dysfunction despite its manufacturing superstars, Chinese pragmatism and bureaucratic incentives, a 10-day itinerary for Yunnan, James C. Scott's work on Zomia, whether Beijing or Shanghai is the better city, Liu Cixin and why volume one of The Three-Body Problem is the best, why contemporary Chinese music and film have declined under Xi, Chinese marriage markets and what it's like to be elderly in China, the Dan Wang production function, why Stendhal is his favorite novelist and Rossini's Comte Ory moves him, what Dan wants to learn next, whether LLMs will make Tyler's hyper-specific podcast questions obsolete, what flavor of drama their conversation turned out to be, and more.

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

Recorded October 31st, 2025.

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Timestamps
00:00:00 - American infrastructure and suburban life
00:05:18 - American vs. Chinese infrastructure buildouts...
00:12:25 - And health care investment
00:17:52 - Chinese suburbs
00:20:10 - The existing lawyerly influence in East Asia
00:25:12 - China's lack of a liberal tradition
00:29:35 - Why China's won't democratize
00:33:49 - China's economic disfunction
00:38:44 - China's expansionism
00:41:55 - Chinese pragmatism and bureaucratic incentives
00:46:50 - Chinese cities and regional culture
00:59:44 - James C. Scott, Zomia, and elite culture
01:06:27 - A 10-day Yunnan itinerary
01:11:57 - On Chinese arts, literature, and cultural expression
01:18:23 - The Dan Wang production function
01:30:34 - Tyler's grand strategy, or lack thereof

Cass Sunstein is one of the most widely cited legal scholars of all time and among the most prolific writers working today. This year alone he has five books out, including Imperfect Oracle on the strengths and limits of AI and On Liberalism: In Defense of Freedom. In his second appearance on the show, he brings his characteristic intellectual range to exploring liberalism's present precariousness and AI's implications for law and speech.

Tyler and Cass discuss whether liberalism is self-undermining or simply vulnerable to illiberal forces, the tensions in how a liberal immigration regime would work, whether new generations of liberal thinkers are emerging, if Derek Parfit counts as a liberal, Mill's liberal wokeism, the allure of Mises' "cranky enthusiasm for freedom," whether the central claim of The Road to Serfdom holds up, how to blend indigenous rights with liberal thought, whether AIs should have First Amendment protections, the argument for establishing a right not to be manipulated, better remedies for low-grade libel, whether we should have trials run by AI, how Bob Dylan embodies liberal freedom, Cass' next book about animal rights, and more.

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

Recorded October 10th, 2025.

This episode was made possible through the support of the John Templeton Foundation.

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