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Invest Like the Best with Patrick O'Shaughnessy

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Invest Like the Best with Patrick O'Shaughnessy
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  • Invest Like the Best with Patrick O'Shaughnessy

    William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

    17/03/2026 | 1 h 10 min
    William Hockey is the co-founder of Plaid and the founder and CEO of Column, a software company that owns a bank and powers Ramp, Wise, Bilt, Mercury, and others. He funded Column by borrowing against his Plaid shares and has never raised outside capital. 

    William talks about what owning 100% of his company allows him to do that other venture-backed founder cannot and the personal risk he took to do so. He shares how Silicon Valley's consensus culture produces consensus founders, and why becoming a founder has become too safe. He believes the best builders are specialists and explains with unusual clarity what it takes to become the best in the world at one specific thing.

    William also spends a lot of time in emerging markets which has given him a unique perspective of the power of the US dollar.

    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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

    -----

    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: William Hockey

    (00:03:49) Column: A Software Company That Owns a Bank

    (00:06:46) Finding Ideas in Emerging Markets

    (00:11:58) Why Constrained Societies Are More Innovative

    (00:16:02) What’s Wrong With Silicon Valley

    (00:19:28) Building a Business Without Raising Money

    (00:22:48) What Venture-Backed Companies Can't Do

    (00:28:39) Getting Margin Called

    (00:31:41) Starting Companies Has Become Too Safe

    (00:34:23) Why Employees Take More Risks Than Founders

    (00:37:09) A Maniacal Commitment to Research

    (00:39:09) Finding Boring Problems to Solve

    (00:41:45) Why Building a Second Company is Easier

    (00:42:36) Missionary vs. Mercenary

    (00:45:49) Funding a Company with Cash Flows

    (00:50:04) Perspective on the Venture Ecosystem

    (00:52:48) The Dominance of the US Dollar

    (00:58:37) The Future of Financial Services

    (01:02:06) Why Big, Inefficient Brands Win From AI

    (01:06:29) The Opportunity for Non-Consensus Founders

    (01:08:03) The Kindest Thing
  • Invest Like the Best with Patrick O'Shaughnessy

    Shyam Sankar - Celebrating Heretics - [Invest Like the Best, EP.462]

    10/03/2026 | 1 h 21 min
    My guest today is Shyam Sankar, the CTO of Palantir Technologies.

    In this conversation, we explore the ideas that shape how Shyam thinks about technology, talent, and national power. We discuss the origins of Palantir’s forward-deployed engineering model and the lessons he learned from Alex Karp about identifying people's "superpowers".

    We also talk about Shyam’s fascination with the "heretics" of American history, the unconventional builders who challenged bureaucracy and created many of the systems that powered America’s military and industrial success. Shyam argues that the United States must reindustrialize after decades of moving production overseas, and explains what we can learn from America’s industrial past.

    In a new Colossus profile, our Editor in Chief Jeremy Stern tells the story of how Shyam became one of the most important but largely unseen figures behind Palantir, tracing his journey from immigrant roots to employee #13 and the architect of the company's success and distinctive culture.

    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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

    -----

    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: Shyam Sankar

    (00:03:24) Defining Heretics in US Military History

    (00:05:01) The Story of Hyman Rickover

    (00:09:55) Formative Experiences & Worldview

    (00:14:50) Components of American Greatness

    (00:17:56) How to Unlock Talent

    (00:25:56) Palantir's Distinct Culture

    (00:28:15) Origin of Forward Deployed Engineering

    (00:34:24) What Does Palantir Actually Do?

    (00:36:19) Example: Airbus

    (00:40:20) State of the US Military Today

    (00:47:33) The U.S. Needs to Reindustrialize

    (00:52:19) Perspective of China

    (00:55:56) Our Key Asymmetric Advantages

    (01:00:57) Executive Orders for a Day

    (01:02:37) Negative Aspects of US Culture

    (01:04:47) Managing Rapid Pivots

    (01:09:17) Where Will AI Value Accrue?

    (01:12:37) Undeclared State of Emergency

    (01:15:45) Surprising Aspects of Palantir

    (01:17:50) To Do or To Be

    (01:18:50) Reflecting on Fatherhood

    (01:19:46) The Kindest Thing
  • Invest Like the Best with Patrick O'Shaughnessy

    John Arnold - China, Energy Markets and Fixing America's Systems - [Invest Like the Best, EP.461]

    04/03/2026 | 1 h 15 min
    My guest today is John Arnold. John is probably the most famous energy trader of all time and certainly the most successful. One of the things John talks about is cultivating the best seat in your industry – the seat with the best perspective, the most information, the best systems.. 

    John has been closely watching China's convergence in robotics, AI, and EVs, and shares his perspective from his recent trip to the country. We talk about the state of energy markets today – the misaligned goals and incentives, the NIMBYism that prevents building in America, and what he actually thinks about the wave of nuclear energy startups that everyone seems excited about. 

    John is also one of the most innovative philanthropists working today, applying that same analytical rigor to diagnosing structural failures across America — in healthcare, criminal justice, education, and beyond

    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 the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai.

    -----

    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) Episode Intro

    (00:03:43) Learnings from John’s Trip to China

    (00:06:28) The EV Industry in China

    (00:08:43) How Subsidies Create Intense Competition

    (00:10:54) US-China Relationship

    (00:12:42) The Cost of Greatness

    (00:14:52) Creating the Best Seat in the Market

    (00:19:30) Baseball Card Arbitrage

    (00:23:03) Trading Natural Gas Futures

    (00:24:59) Energy Market Making Explained

    (00:27:11) Why Energy is Exciting Again

    (00:31:14) Meeting the Increased Demand for Energy

    (00:32:53) Why Policy is the Biggest Threat to Progress

    (00:36:28) Fixing Energy Infrastructure in the US

    (00:39:29) Advanced Nuclear Technology

    (00:42:05) The Prospects of Energy Startups

    (00:43:44) Input Costs in Solar & Batteries

    (00:47:54) Geothermal Energy: The Most Exciting Sector

    (00:50:57) Housing Reform in the US

    (00:53:39) The Role of Philanthropic Foundations

    (00:57:00) Reforming the Criminal Justice System

    (01:03:48) Social Outcomes Downstream of Education

    (01:07:20) Misaligned Incentives in the Healthcare System

    (01:12:08) Journalism as a Public Good

    (01:14:17) The Kindest Thing
  • Invest Like the Best with Patrick O'Shaughnessy

    Dan Sundheim - The Art of Public and Private Market Investing - [Invest Like the Best, EP.460]

    24/02/2026 | 1 h 15 min
    My guest today is Dan Sundheim. Dan is the founder and CIO of D1 Capital Partners.

    He thinks about markets and businesses constantly, and has built a career entirely around that obsession. He manages over $30B across both public and private markets, with investments in SpaceX, OpenAI and Anthropic, and a public portfolio of names you may never have heard of.

    Dan shares the story of the short case he wrote on Orthodontic Centers of America and posted on Value Investors Club, which crashed the stock, and helped him land his first job.

    He shares why he backed Anthropic at a moment when many people told him it was the Lyft to OpenAI’s Uber, what reading Dario Amodei’s essays reminded him of Jeff Bezos, and how he thinks about LLM business models through the lens of Netflix and Spotify.

    We spend time on the extraordinarily stressful moment in early 2021 when GameStop hit the firm, and what Dan believes is the single biggest tail risk facing the global economy right now.

    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 the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

    -----

    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: Dan Sundheim

    (00:03:58) The State of Public & Private Investing

    (00:07:32) Investing in OpenAI and Anthropic

    (00:10:22) LLMs Business Model

    (00:14:13) How LLMs are like Netflix and Spotify

    (00:17:08) Focus v. Scope

    (00:22:43) The Bear Case for Hyperscalers

    (00:26:36) The Software Sell-Off

    (00:31:08) If Scaling Laws Stopped

    (00:32:18) Advice to a 12-Year-Old Investor

    (00:33:54) GameStop: D1’s Darkest Hour

    (00:37:14) The Pivotal Dinner with LPs

    (00:40:56) Staying Calm and Confident

    (00:42:08) Economic Optimism vs. Societal Uncertainty

    (00:44:26) Investing on SpaceX and Rivian

    (00:48:09) Why Dan Loves Shorting

    (00:48:51) Sources of Inefficiency in Today’s Markets

    (00:51:45) The Importance of Loyalty

    (00:53:11) Dan’s Group Chat for Founders

    (00:55:39) What Motivates Dan

    (00:57:28) Posting on Value Investors Club

    (01:01:46) What Dan Learned at Viking

    (01:04:22) The Beauty of Art

    (01:06:49) Under-appreciated Parts of the Global Economy

    (01:08:00) The US-China-Taiwan Collision Course

    (01:12:10) Good Leaders vs. Good Businesses

    (01:13:15) The Kindest Thing
  • Invest Like the Best with Patrick O'Shaughnessy

    Josh Kushner - Concentration and Conviction - [Invest Like the Best, EP.459]

    18/02/2026 | 1 h 3 min
    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.

    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 the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

    -----

    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

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À propos de Invest Like the Best with Patrick O'Shaughnessy

Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.colossus.com
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