Invest Like the Best with Patrick O'Shaughnessy

Gabe Stengel is the co-founder and CEO of Rogo, the AI platform for finance. He believes the best investors will spend the next several years reinventing their firms around AI, and Rogo is trying to build the infrastructure that allows them to do it.

We discuss how Rogo evolved alongside the frontier models, why the last mile and the harness around the models matter so much, what happens when every portfolio manager can deploy thousands of agents against a problem, and how AI could transform the way capital is raised, assets are priced, and deals get done.<...

Michael Moritz led Sequoia Capital for nearly two decades and backed some of the defining companies of the internet era. 

In his new memoir, Ausländer, he turns his attention to his own family, Jewish refugees who fled Nazi Germany and rebuilt their lives in Wales. 

We discuss the imprint his parents left on him, the method he used for decades of asking founders about their childhoods and the Time profile that ended his relationship with Steve Jobs. 

We also also cover Lee Iacocca, why Don Valentine hired him, Alex Ferguson's approach to mana...

My guest today is Walter Russell Mead. Walter is a columnist at the Wall Street Journal and the author of Special Providence and God and Gold, two of the best books written on American power. 

He has spent decades studying how the United States came to dominate the world, and our conversation is about whether it can keep doing so. 

Walter lays out the five step playbook that carried the Dutch, then the British, then America to global leadership, and why the same pattern keeps beating centralized continental powers. 

We discuss how Trump tur...

My guest today is Sarah Guo, founder and managing partner of Conviction, the venture firm she built to back AI-native companies from their earliest days. 

Sarah has become one of the most sought-after early-stage investors in AI, often the first check into the companies defining the frontier. 

In this conversation, we go inside that frontier: what the small group of people actually building AI believe right now, why some of the field's best researchers are wrestling with their own sense of purpose, and how close we are to robots in the home and a genuine ac...

My guest today is Neil Movva, founder of Sail. Sail is building what Neil calls a token factory, an inference company designed for a specific kind of future, one where AI agents run in the background for hours or days at a time rather than answering a human in real time. 

In that world, latency matters less and cost matters more, and Neil has built the whole company around driving the cost of a token as low as it can possibly go.

What makes this conversation special is that it is one of the most d...

My guest today is Ben Thompson, the founder and author of Stratechery. Ben is one of my favorite business thinkers and I love talking to him about everything happening in markets and technology. 

We go through every important company, including OpenAI, Nvidia, Intel, Apple, Microsoft, Google, and Amazon. We also discuss why he thinks it would be dangerous for the United States to win the AI race outright, what container shipping and the railroads of the 1870s tell us about the buildout, and why the binding constraint on all of this may be capital rather than compute. 

My guest today is Eric Vishria, a General Partner at Benchmark. 

Eric has spent his career in software and cloud, and few people know the history of these markets as well as he does. What makes him special is his ability to use that history to make sense of today. 

We discuss what the rise of AWS teaches us about AI, what he has learned from investing in Fireworks, Sierra, and Cerebras, and how the criteria for winning have changed for founders and investors. 

Please enjoy my conversation with Eric Vishria.

For...

My guest today is Gavin Baker, founding partner and CIO of Atreides Management. This is our seventh conversation, and just two months after Gavin's last appearance.

It's about the gap between what the market is doing and what companies are seeing. It's been a tough month or so for public AI names, but there's no sign of a slowdown on the ground in Silicon Valley.

We discuss the latest moves, contracted vs. spot GPU prices, the game theory of memory supply agreements, and why Claude has become the Walter Cronkite of the stock market. We...

My guest today is Sam Altman, CEO of OpenAI.

It's a conversation spanning the history, present, and future of OpenAI, from the origin of ChatGPT through Codex, hardware, and their new Jalapeno chip.

We discuss the early decision to buy compute at a scale nobody thought was rational, and the plan to build a gigawatt of new capacity every week. 

We talk about Kimi and distillation, the Hugging Face incident and what it means for the pace of AI development, and what it's like to raise kids who will grow up never knowing a...

My guest today is Matthew Smith. Matthew is the founder and CIO of Chronometer Partners, which invests in energy, industrials, materials, power and utilities, and related infrastructure.

For the last 18 months he and his team have modeled nearly every natural gas well, pipeline, and processing asset in the United States. He's reached a conclusion most of the market doesn't share. 

Starting in 2028, AI data centers and LNG exports will need more gas than the country can produce and deliver. By his math, the US could exhaust its working natural gas storage by 2030. In his words, t...

Today my guest is John Kim. John is one of the world's top and most prolific fundraisers. 

He was chief client officer at General Catalyst, where he helped raise many of the firm's flagship funds. He is now chairman and president of corporate development at Lila Sciences, a company building scientific superintelligence, where he has helped raise several hundred million dollars. 

He is also the author of The Tao of Fundraising. 

This conversation is really a guide on how to raise money from someone who has done it at the highest level. We tal...

My guest today is Jeremy Giffon.  Jeremy has been on the show before as one of our most popular guests, and this conversation is every bit as enjoyable as the first.

Over the last 18 months, Jeremy has had hundreds of conversations with founders and with the capital behind their companies. I don't know many investors with such a high rep count in the most interesting corners of private markets, so I asked him what he has learned.

We talk about what those lessons mean for founders and investors, why everyone has become subservient to the po...

My guests today are Gavin Uberti and Rob Wachen, the founders of Etched. 

A few years ago, when they set out to build a better AI chip than the largest companies in the world, almost everyone I called told me it could not be done. They have since done it, taping out a working chip on their first attempt and becoming the first hardware company founded after ChatGPT to do so.

They already have more than a billion dollars of customer demand for their first product, and have raised eight hundred million dollars to build i...

My guest today is Vlad Barbalat, the Chief Investment Officer of Liberty Mutual Investments, the $120 billion investment platform that sits within one of the largest insurance companies in the world. 

Vlad grew up in Soviet Moldova, came to America in 1990, and built a career that eventually led him to one of the most distinctive capital allocator seats anywhere in finance. 

Today we talk about how the mutual insurance structure creates a unique investment platform, what Liberty looks for in a new deal or partner, and what it means to build a career and a life in...

My guest today is Kareem Amin, co-founder and CEO of Clay. Clay has become one of the fastest-growing software companies of the last few years, valued at over four billion dollars. It helps companies find their best customers and reach them at scale.

But this conversation is about a lot more than Clay. Kareem is one of the most original thinkers I know. 

We talk about the statues he keeps at the center of how he runs Clay — truth, justice, and courage — and what those words demand of him in practice. We talk about risk, ambit...

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 earnings power. 

This conversation is a tour through how he applies that framework right now. We st...

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...

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 up as a credit and eve...

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, and what the rise of neo-prime defense companies will...

My guest today is Gavin Baker, founding partner and CIO of Atreides Management, and this is our sixth conversation.

The central theme is watts and wafers, the two physical constraints that in Gavin's view will dictate the next phase of AI.

On power, he thinks the near-term shortage starts to ease in 2027 and 2028 as new sources of energy come online, and that orbital compute solves it in the long term.

On wafers, he explains what is different this time from the dotcom bubble and why TSMC’s capacity decisions may be the single mo...

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 why the returns to frontier intelligence keep getting higher, especially in enterprise, and how Anthropic...

My guest today is Brian Chesky, the co-founder and CEO of Airbnb. Our conversation traces the path from his early training as an industrial designer at RISD through the pandemic moment that forced him into founder mode. 

He explains why he thinks AI founder mode will demand even more attention to the details and why founders are rarely good early CEOs.

He walks through his eleven-star exercise, which is a way of imagining the most absurd version of a customer experience to achieve product market fit. 

We also talk about what changed for hi...

My guest today is Paul Tudor Jones. Paul is the founder of Tudor Investment Corporation and one of the greatest macro traders of all time, known for calling and profiting from the 1987 crash and compounding capital at extraordinary rates over more than four decades.

Paul is also one of the most entertaining and interesting people I have ever met. He is full of stories and hard-earned lessons from a lifetime in markets that feels like several lifetimes compressed into one.

In this conversation, he shares how he thinks about trading as a constant battle of...

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 million this year.

On supply, we walk through the bottlenecks across memory...

My guest today is Alex Karnal. Alex is the co-founder and managing partner of Braidwell, a life sciences investment firm he built after spending 15 years at Deerfield Management.

The frame we use throughout the episode is the health stack. Alex talks about how most of the diseases that will claim most of our lives are already addressable with medicines that exist today. We work through the five layers of what a defensive health strategy looks like, why GLP-1 medicines represent the first commercial proof that people are ready to be proactive about their health, and why PCSK9...

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 advanced reactors everyone is counting on to power the next wave...

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 conversation, he traces the evolution of American finance from...

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 without being trained on them directly, and why everyday human actions remain the hardest problems in the field.<...

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 base of world-class executives and entrepreneurs. 

In this conversation, Mitchell walks through every component of the ma...

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 e...

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...

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 think...

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.

...

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...

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 has produced a series of iconic deals, including Burger King, Tim H...

My guest today is Ben Horowitz, the co-founder of Andreessen Horowitz. Since its founding in 2009, a16z has grown into one of the most influential firms in venture capital, reshaping how technology companies are funded and how power and ideas move through Silicon Valley and around the world.

This conversation focuses on sides of Ben’s story you don’t often hear. Ben reflects on the people who shaped him, including Nas, Andy Grove, and his father, and shares why he chose to personally fund new technology for the Las Vegas Police Department.

We also talk...

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 about how product building is changing with AI. We discuss the one thing Gokul believes is truly...

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 principles that guide how I think about buildi...

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 during the pandemic.

Tom and Gr...

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 an exceptionally high bar over decades as a company grows. 

We...