Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]

Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]

Author: Colossus | Investing & Business Podcasts March 28, 2025 Duration: 1:47:33
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of one conversations with N of one people. This is a rare opportunity to hear from one of the best investors of the past decade—Josh Kushner, founder and managing partner of venture firm, Thrive Capital. Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and, in it, Thrive led Warby Parker’s Series A, invested in Instagram, and incubated a business, which Josh co-founded, called Oscar. Their portfolio is stage agnostic and their track record includes many of the best known businesses from the past decade, including Spotify, Unity, Stripe, and Twitch among many more. Please enjoy my great conversation with Josh Kushner. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by WorkOS. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit WorkOS.com to Transform your application into an enterprise-ready solution in minutes, not months. ----- This episode is brought to you by Passthrough. Passthrough streamlines subscription documents, KYC, and AML compliance, so you can focus on running your fund, not managing paperwork. New SEC Update 31 CFR hits investment firms in under a year, and managers are getting ready for it now. If you think basic OFAC screening is enough, think again. You'll need continuous monitoring of your investors and all their beneficial owners across multiple watchlists, plus a comprehensive anti money laundering program. Passthrough has already processed 50,000 LPs and built the complete solution. Don't risk SEC deficiency letters, fines, or regulatory enforcement. Visit passthrough.com to get compliant now. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:00:00) Welcome to Invest Like the Best (00:05:14) Why do this podcast (00:08:14) The development of taste and quality  (00:12:20) CS Lewis tweet; The Inner Ring (00:18:14) Overview the founding story of Oscar Health (00:25:18) Learning to identify good problems and creating a business to solve it (00:27:43) The birth story of Thrive Capital (00:32:14) Lessons learned from creating the first three Thrive funds (00:39:44) Talent, recruiting and seeing potential in younger generations of people (00:47:40) Investments he made during the early foundation of Thrive that had significant impact (00:51:12) His analogy for investing in early versus late stage and styles of real estate investing (00:56:22) The current macro environment (01:00:57) Why he sold small stakes of Thrive (01:05:10) His philosophy on what makes a good product (01:10:10) His absence from crypto and why he refrained during the boom in 2021 (01:12:33) Thoughts about the opportunity set in FinTech today writ large (01:15:39) Lessons learned from his time spent with Marc Andreessen (01:17:43) Lessons learned from Stan Druckenmiller, Henry Kravis, and David Geffen (01:22:09) Firm values he thinks are very important (01:31:15) Vision as a key ingredient for founders (01:34:19) His view of the investment industry in the world today writ large  (01:44:48) The kindest thing anyone has ever done for him

Patrick O’Shaughnessy sits down with some of the most interesting minds in finance and industry on Invest Like the Best. This isn't about quick tips or market noise; each conversation is a deep, structured exploration of how these leaders think, make decisions, and build lasting success. You’ll hear firsthand about the frameworks and personal philosophies that drive exceptional returns, both in capital and in life. The discussions regularly venture into the technological shifts reshaping entire sectors, offering a forward-looking perspective crucial for any serious investor or operator. Produced by Colossus, this podcast serves as an ongoing masterclass for anyone looking to refine their strategy, whether they're managing a portfolio, running a company, or building something new. The value lies in the nuanced stories and concrete methods shared by guests, providing a rare level of insight that goes far beyond typical interviews. Tune in for thoughtful, substantive dialogue that challenges conventional wisdom and focuses on the principles of long-term value creation.
Author: Language: English Episodes: 100

Invest Like the Best with Patrick O'Shaughnessy
Podcast Episodes
Jack Kokko - Building AlphaSense - [Invest Like the Best, EP.404] [not-audio_url] [/not-audio_url]

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My guest today is Jack Kokko. Jack is the CEO and Founder of AlphaSense, an AI-powered search engine for market intelligence. He shares how AlphaSense began by aggregating fragmented financial data sources and evolved wi…
Jared Kushner - The Mechanic - [Invest Like the Best, EP.403] [not-audio_url] [/not-audio_url]

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Scott Wu - Building Cognition - [Invest Like the Best, EP.402] [not-audio_url] [/not-audio_url]

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My guest today is Scott Wu. Scott is the co-founder and CEO of Cognition, which is an applied AI lab that has created the first AI software engineer, which they call Devin. In just a year since founding Cognition, Devin…
Micky Malka - Building Ribbit - [Invest Like the Best, EP.401] [not-audio_url] [/not-audio_url]

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My guest today is Micky Malka. Micky is the founder of Ribbit Capital, a global venture capital firm that focuses exclusively on financial technology investments. He is a renowned investor for his adaptability and vision…
Ronnie Fieg - Building Kith - [Invest Like the Best, EP.399] [not-audio_url] [/not-audio_url]

Duration: 1:27:08
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Gabe Whaley - Building MSCHF - [Invest Like the Best, EP.398] [not-audio_url] [/not-audio_url]

Duration: 1:18:23
My guest today is Gabe Whaley, the founder and CEO of MSCHF. What began with viral internet pranks in 2014 has evolved into one of the most singular creative companies in modern culture. MSCHF’s work ranges from microsco…
Brad Jacobs - Think Big and Move Fast - [Invest Like the Best, REPLAY] [not-audio_url] [/not-audio_url]

Duration: 1:27:00
Today, we are replaying my conversation with Brad Jacobs. Brad’s resumé is remarkable. He has founded seven companies, all of which are billion-dollar or multibillion-dollar businesses. He has done 500 M&A transactions a…
Ernie Garcia - Leading Through Crisis - [Invest Like the Best, EP.397] [not-audio_url] [/not-audio_url]

Duration: 1:13:56
My guest today is Ernie Garcia. Ernie is the co-founder and CEO of Carvana. Ernie joined me on Founder’s Field Guide in 2021 and despite all that the business has gone through since that conversation, you’ll hear how he…