This is my second conversation with Josh Kushner, founder and managing partner of Thrive Capital. I recorded this conversation in October after publishing the Colossus cover story about him and Thrive. Given the overwhelming response, we created some breathing room before releasing it. Josh started Thrive in 2011. The firm now manages approximately $50 billion with a very small investment team. What makes Thrive different is how concentrated they are and how involved they get with their portfolio companies. We cover the iconic investments that defined Thrive: Instagram, Stripe, GitHub, and spend a lot of time on OpenAI. Josh explains how Thrive thinks about investing today and the three categories they're currently focused on. Josh also talks about building the firm, why they keep the team small, and what he's learned from A24 about enabling artists to do their best work. He shares personal stories that shaped him, including his grandmother's experience surviving the Holocaust, and lessons from Stan Druckenmiller, Jon Winkelried, and others at formative moments in Thrive's history. Please enjoy my great conversation with Josh Kushner. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠.  ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at ⁠Rogo.ai/invest⁠. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:43) Intro: Josh Kushner (00:03:46) How Thrive Has Changed Since 2023 (00:05:18) Thrive’s Entrepreneurial Culture (00:12:22) The Power of Small Teams (00:13:35) Sponsors (00:14:35) Concentration as Differentiation (00:16:16) The Github Deal (00:18:08) Lesson from Stan Druckenmiller (00:20:37) Leading Stripe’s $50 Billion Round (00:23:16) Instagram: Doubling an Investment in Days (00:25:43) Isomorphic: Thrive as an Enabling Technology (00:27:04) Thrive & A24 (00:28:19) OpenAI: The Product Josh Couldn’t Unsee (00:32:09) Pricing the OpenAI Investment (00:33:40) OpenAI and Power (00:35:26) Finding Joy in Hard Work (00:39:15) Inside View of the Tech & AI Landscape (00:42:28) Three Investment Categories Thrive is Focused On (00:44:37) Thrive Holdings: Inside-Out Disruption (00:48:54) Competition in Venture (00:50:49) Sponsors (00:51:48) Thrive’s Immutable Values (00:54:21) A Family Story of Survival (00:56:43) The American Dream (00:58:03) What Artists Can Teach Investors (01:00:26) Never Compromise Your Values (01:01:33) The Story Behind Josh’s Forever Watch