Invest Like the Best with Patrick O'Shaughnessy - podcast cover

Invest Like the Best with Patrick O'Shaughnessy

Colossus | Investing & Business Podcastscolossus.com
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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Episodes

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

My guest today is Alex Sacerdote , founder of Whale Rock Capital Management. Whale Rock is a technology focused investment firm that manages more than $17 billion across hedge fund, long only, and hybrid strategies. Over the past three years it has been one of the best performing hedge funds, compounding at roughly 44 percent a year. Alex invests through a single lens that he has refined over twenty years. He looks for technology S-curves, durable competitive advantages, and underappreciated ear...

Jun 09, 20261 hr 12 minEp. 477

Dara Khosrowshahi - Uber's Bet on AVs, AI, and Building a Super-App - [Invest Like the Best, EP.476]

My guest today is Dara Khosrowshahi , the CEO of Uber. Before Uber, Dara ran Expedia for thirteen years. We start with why he took this job in 2017, and a big part of that story is Daniel Ek, who told him that life is not about happiness, it is about impact. We talk about what the chaos felt like on day one, and how his family leaving Iran when he was nine shaped the way he handles pressure today. We spend most of our time on autonomous vehicles and Uber's role as the demand aggregator in a worl...

Jun 03, 20261 hr 7 minEp. 476

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

My guest today is Dan Loeb , the founder and CEO of Third Point. Dan started Third Point in 1995 with a few million dollars, and today the firm manages over 24 billion across equities, corporate and structured credit, venture, and insurance. He is best known for his activist work at companies like Sotheby's, Sony, and Yahoo, and for the public letters he has written to boards over the years. What I find most interesting about Dan is how much his approach has evolved across thirty years. He came ...

May 28, 20261 hr 3 minEp. 475

Darren Farber on Iran, China, and the Rise of Neoprimes - [Invest Like the Best, EP.474]

My guest today is Darren Farber, and this is his second appearance on the show. Darren is a Managing Partner of Albion River, a defense-focused investment firm and he previously served as a special advisor to the Deputy Under Secretary of Defense. We recorded this conversation in the middle of the Iranian contingency, and we spent most of our time on what winning actually means in a theater like Iran. We discuss why magazine depth matters for the American industrial base, lessons from Ukraine, a...

May 26, 202646 minEp. 474

Gavin Baker - Watts and Wafers - [Invest Like the Best, EP.473]

Gavin Baker of Atreides Management discusses the physical constraints of AI—watts and wafers—and how they will shape its next phase. He explores solutions like orbital compute for power and TSMC's role in managing wafer supply, which could prevent an AI market bubble. The conversation also delves into the economic value accruing to frontier models, the challenges for AI-native founders, and the broader societal and geopolitical impacts of rapidly advancing AI.

May 20, 20261 hr 17 minEp. 473

Krishna Rao - Anthropic's CFO on Compute, Scaling to $30B ARR, and the Returns to Frontier Intelligence - [Invest Like the Best, EP.472]

My guest today is Krishna Rao , the CFO of Anthropic. The center of our conversation is how he navigates the decision around procuring and allocating compute, which he describes as the canvas on which everything else gets built. We talk about what he calls the cone of uncertainty, the three chip platforms Anthropic uses fungibly across Trainium, TPUs, and GPUs, and the daily meetings they run to allocate compute between model development, internal use, and serving customer demand. He explains wh...

May 13, 20261 hr 16 minEp. 472

Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.471]

Airbnb co-founder Brian Chesky shares insights from his journey, from industrial design to leading a global company, emphasizing the shift from traditional CEO roles to an intense 'AI Founder Mode' focused on extreme detail and direct engagement. He discusses the future of consumer AI, Airbnb's strategic pivot from 'home to person,' and the importance of intrinsic motivation over external adulation. Chesky also highlights the power of making problems small, the 'eleven-star experience' for radical innovation, and the crucial role of hiring top talent, drawing parallels with lessons from bodybuilding.

May 05, 20261 hr 15 minEp. 471

Paul Tudor Jones - Lessons From 50 Years in Markets - [Invest Like the Best, EP.470]

In this insightful conversation, renowned macro trader Paul Tudor Jones delves into his 50 years in markets, contrasting trading with investing and reflecting on lessons from figures like Warren Buffett. He expresses alarm over AI's unmanaged risks, advocates for watermarking, and offers his perspective on current market bubbles, including Bitcoin as an inflation hedge. Beyond finance, Jones shares his passion for philanthropy, the importance of effective communication, and his philosophy for a fulfilling life centered on kindness, family, and purpose.

Apr 28, 20261 hr 7 minEp. 470

Dylan Patel - The Infinite Demand for Tokens, Claude Mythos, and Supply Constraints - [Invest Like the Best, EP.469]

This is my second conversation with Dylan Patel . Dylan is the founder and CEO of SemiAnalysis, where he tracks the semiconductor supply chain and AI infrastructure buildout. This conversation is about the supply and demand of tokens. On demand, Dylan describes something completely explosive. He explains why the frontier model is the only model anyone wants, and willingness to pay for it is nearly unbounded. His own firm has gone from tens of thousands of dollars in AI spend last year to seven m...

Apr 23, 202645 minEp. 469

Alex Karnal - The Trillion-Dollar Health Revolution - [Invest Like the Best, EP.468]

Alex Karnal, co-founder of Braidwell, explores the "health stack" framework for proactive health, highlighting the transformative impact of GLP-1 and PCSK9 medicines. He details the inflection points in drug adoption, the barriers to access, and the scientific method of drug discovery. The discussion also covers how AI is set to revolutionize therapeutic development through automated labs and scientific superintelligence, signaling a deterministic shift in biology and a potential trillion-dollar revolution in public health.

Apr 21, 20261 hr 32 minEp. 485

Scott Nolan - SpaceX, Founders Fund, and Rebuilding American Uranium Enrichment - [Invest Like the Best, EP.467]

Scott Nolan spent 12 years at Founders Fund looking for the most important problems that no one else was funding. Then he found a problem so critical, and so ignored, that he couldn't find a company to back. So he started one. General Matter is rebuilding US uranium enrichment. The United States was the world leader in enrichment through the 1980s and then stopped entirely. Today roughly a quarter of US enriched uranium comes from Russia, a ban on those imports takes full effect in 2028, and the...

Apr 14, 20261 hr 16 minEp. 467

Alan Waxman - Private Credit and the Modern Financial System - [Invest Like the Best, EP.466]

My guest today is Alan Waxman , co-founder and CEO of Sixth Street, a $130B global investment firm. Private credit is one of the most discussed topics in markets right now, and there is a lot to make sense of. The current discourse is almost entirely focused on symptoms. Alan Waxman has spent the time diagnosing the root cause. Alan thinks about the financial system the way a historian would, studying the incentives, guardrails, and market structure that determine how things play out. In this co...

Apr 08, 20261 hr 2 minEp. 466

Sergey Levine - Building LLMs for the Physical World - [Invest Like the Best, EP.465]

My guest today is Sergey Levine , a professor at UC Berkeley and co-founder of Physical Intelligence . The company is building robotic foundation models designed to control any embodied system to do any task in any environment. Sergey argues that solving robotics at full generality is the right path, and that building systems that learn across many robots, environments, and tasks may be the more scalable approach than building narrow specialists. We discuss how these models can perform new tasks...

Mar 31, 20261 hr 7 minEp. 465

Mitchell Green - Lessons from Cold Calling 10,000 Companies - [Invest Like the Best, EP.464]

My guest today is Mitchell Green . Mitchell Green is the co-founder and managing partner of Lead Edge Capital, a growth equity firm that has spent 15 years building one of the most disciplined investment machines in the business. Unlike most firms chasing power law outcomes, Lead Edge is designed to deliver consistent returns by talking to thousands of companies a year, applying a rigorous eight-point criteria to filter down to a handful of investments, and leveraging a uniquely constructed LP b...

Mar 24, 202654 minEp. 464

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

William Hockey, co-founder of Plaid and CEO of Column, details his unique strategy of self-funding a bank-owning software company, defying traditional venture capital models by taking significant personal risk. He offers a critical perspective on Silicon Valley's consensus culture and how it stifles true entrepreneurial risk. Hockey also discusses the global dominance of the US dollar and the transformative potential of AI for large, often inefficient, financial institutions.

Mar 17, 20261 hr 11 minEp. 463

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

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 s...

Mar 10, 20261 hr 22 minEp. 462

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

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...

Mar 04, 20261 hr 16 minEp. 461

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

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 st...

Feb 24, 20261 hr 15 minEp. 460

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

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 portfol...

Feb 18, 20261 hr 3 minEp. 459

Alex Behring and Daniel Schwartz - Inside 3G Capital - [Invest Like the Best, EP.458]

My guests today are Alex Behring and Daniel Schwartz , Co-Managing Partners of 3G Capital. 3G has built one of the most distinctive firms in investing around a simple idea: there are only a handful of truly great businesses and even fewer great CEOs. Their model is to raise capital with the intention of making just one investment per fund, commit meaningful amounts of their own money alongside their partners, and focus all of their time and best people on that single opportunity. Their approach ...

Feb 10, 20261 hr 36 minEp. 458

Ben Horowitz - Backing America’s Future - [Invest Like the Best, EP.457]

Ben Horowitz explores how AI is reshaping company building, investing, and addressing societal challenges like inequality by democratizing opportunities. He shares a16z's ambitious mission to expand the technology market in America, drawing on lessons from Andy Grove and his father. The conversation also highlights unique applications of technology, including funding for the Las Vegas Police Department, and personal influences.

Feb 03, 202656 minEp. 457

Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

My guest today is ⁠Gokul Rajaram⁠ , Founding Partner at Marathon Management. Gokul is one of the most prolific product builders and investors of the last twenty years. He has built the core ad and product businesses at Google, Facebook, Square, and DoorDash, working at each company during its most formative scaling periods. Alongside his operating career, Gokul has invested in more than 700 companies, giving him an unusually broad view into how products are built and scaled. This conversation is...

Jan 29, 20261 hr 16 minEp. 456

Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]

This week is a special episode. Only David Senra could get me to be on the other side of the mic. Because I don’t plan on being interviewed often, I wanted to share this conversation, which I so enjoyed, with our audience. It went in a very different direction than I expected. We barely talk about investing or interviewing. Instead, we talk about finding an organizing principle for life, undiscovered talent, and the idea that “the reward for good work is more work.” We also discuss the principle...

Jan 20, 20262 hr 7 minEp. 455

Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]

My guests today are Tom Digan and Greg Stewart . Tom is the co-founder of Ladder , and Greg is its CEO. Ladder was my first angel investment. What followed over the next seven years is one of the most unlikely and dramatic business stories I’ve been a part of. Today, Ladder is the number one grossing fitness app in the App Store, approaching $100M in ARR with more than 300,000 paying members. But the path from near death to dominance involved debt collectors, leadership changes, and a full reset...

Jan 13, 20261 hr 14 minEp. 454

Reed Hastings - Building Netflix - [Invest Like the Best, EP.453]

My guest today is Reed Hastings , the co-founder and former longtime CEO of Netflix. Netflix is an example of two ideas that everyone talks about, but are extremely hard to do in practice. The first is finding a simple idea and taking it extraordinarily seriously. Reed talks about how even the DVD business was nothing more than a stepping stone toward streaming, which they envisioned from the company’s inception in 1997. The second is talent density, and what it actually takes to set and sustain...

Jan 06, 20261 hr 3 minEp. 453

Nick Kokonas - Know What You Are Selling - [Invest Like The Best, REPLAY]

Today, I am replaying my conversation with Nick Kokonas , one of my favorites from the show. Nick is the co-founder of 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. He majored in philosophy before becoming a derivatives trader and is now one of the most well-known names in the hospitality industry. In this conversation, Nick shares his experience of bringing a business mindse...

Dec 30, 20251 hr 18 min

Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS]

Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS] Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Ric Elias is the CEO and co-founder of Red Ventures, which has a portfolio of fast-growing digital businesses like Lonely Planet, The Points Guy, Bankrate, and large investments in a variety of other businesses across industries. He began the business in 2000 and ...

Dec 23, 20251 hr 25 min

Henry Ellenbogen - Man Versus Machine - [Invest Like the Best, EP.452]

My guest today is Henry Ellenbogen , founder and Managing Partner of Durable Capital Partners. Henry built his reputation at T. Rowe Price, where he led the New Horizons Fund and turned it into one of the best-performing small-cap growth portfolios in the country. In 2019, he left to start Durable. His philosophy is grounded in a simple belief that great investing is about understanding people and change. Henry has spent his career studying the rare 1% of companies that drive nearly all long-ter...

Dec 16, 20251 hr 48 minEp. 452

Gavin Baker - Nvidia v. Google, Scaling Laws, and the Economics of AI - [Invest Like the Best, EP.451]

My guest this week is Gavin Baker . Gavin is the managing partner and CIO of Atreides Management, and he has been on the show many times before. I will never forget when I first met Gavin in 2017. I find his interest in markets, his curiosity about the world to be as infectious as any investor that I've ever come across. He's encyclopedic on what is going on in the world of technology today, and I've had the good fortune to host him every year or two on this podcast. Gavin began covering Nvidia ...

Dec 09, 20251 hr 26 minEp. 451

David George - Building a16z Growth, Investing Across the AI Stack, and Why Markets Misprice Growth - [Invest Like the Best, EP.450]

My guest today is David George . David is a General Partner at Andreessen Horowitz, where he leads the firm’s growth investing business. His team has backed many of the defining companies of this era – including Databricks, Figma, Stripe, SpaceX, Anduril, and OpenAI – and is now investing behind a new generation of AI startups like Cursor, Harvey, and Abridge. This conversation is a detailed look at how David built and runs the a16z growth practice. He shares how he recruits and builds his team ...

Dec 02, 20251 hr 7 minEp. 450
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