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Invest Like the Best with Patrick O'Shaughnessy

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

All episodes(100)

  • Intelligent Report
    Etched - Building AI Hardware to Make Inference Faster and Cheaper

    Published Jun 30, 2026

    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 mill

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    Vlad Barbalat - Investing $120 Billion in Permanent Capital

    Published Jun 23, 2026

    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

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    Kareem Amin - The Unusual Approach to Company Building

    Published Jun 16, 2026

    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 pract

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    Alex Sacerdote - How to Invest Through Technology Cycles

    Published Jun 9, 2026

    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 earn

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    Dara Khosrowshahi - Uber's Bet on AVs, AI, and Building a Super-App

    Published Jun 3, 2026

    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 world

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    Dan Loeb - Lessons from 30 Years of Investing

    Published May 28, 2026

    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 u

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    Darren Farber on Iran, China, and the Rise of Neoprimes

    Published May 26, 2026

    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

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    Gavin Baker - Watts and Wafers

    Published May 20, 2026

    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 capac

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    Krishna Rao - Anthropic's CFO on Managing Compute, Scaling to $30B ARR, and the Returns to Frontier Intelligence

    Published May 13, 2026

    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

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    Brian Chesky - AI Founder Mode

    Published May 5, 2026

    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

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    Paul Tudor Jones - Lessons From 50 Years in Markets

    Published Apr 28, 2026

    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, h

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    Dylan Patel - The Infinite Demand for Tokens, Claude Mythos, and Supply Constraints

    Published Apr 23, 2026

    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 mi

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    Alex Karnal - The Trillion-Dollar Health Revolution

    Published Apr 21, 2026

    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 commerc

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    Scott Nolan - SpaceX, Founders Fund, and Rebuilding American Uranium Enrichment

    Published Apr 14, 2026

    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

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    Alan Waxman - Private Credit and the Modern Financial System

    Published Apr 8, 2026

    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 con

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    Sergey Levine - Building LLMs for the Physical World

    Published Mar 31, 2026

    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 w

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    Mitchell Green - Lessons from Cold Calling 10,000 Companies

    Published Mar 24, 2026

    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 ba

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    William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy

    Published Mar 17, 2026

    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

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

    Published Mar 10, 2026

    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 sy

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    John Arnold - China, Energy Markets and Fixing America's Systems

    Published Mar 4, 2026

    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

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    Dan Sundheim - The Art of Public and Private Market Investing

    Published Feb 24, 2026

    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 sto

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    Josh Kushner - Concentration and Conviction

    Published Feb 18, 2026

    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 portfoli

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    Alex Behring and Daniel Schwartz - Inside 3G Capital

    Published Feb 10, 2026

    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 h

  • Intelligent Report
    Ben Horowitz - Backing America’s Future

    Published Feb 3, 2026

    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 te

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    Gokul Rajaram - Lessons from Investing in 700 Companies

    Published Jan 29, 2026

    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

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    Patrick O’Shaughnessy - Creating on Principle

    Published Jan 20, 2026

    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

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    Tom Digan & Greg Stewart - Building the World’s Best Fitness App

    Published Jan 13, 2026

    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 d

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    Reed Hastings - Building Netflix

    Published Jan 6, 2026

    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

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    Nick Kokonas - Know What You Are Selling

    Published Dec 30, 2025

    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 mindset

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    Ric Elias - The Art of Living Well

    Published Dec 23, 2025

    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

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    Henry Ellenbogen - Man Versus Machine

    Published Dec 16, 2025

    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-term

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    Gavin Baker - Nvidia v. Google, Scaling Laws, and the Economics of AI

    Published Dec 9, 2025

    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 a

  • Intelligent Report
    David George - Building a16z Growth, Investing Across the AI Stack, and Why Markets Misprice Growth

    Published Dec 2, 2025

    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 a

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    Palmer Luckey - Inventing the Future of Defense

    Published Nov 28, 2025

    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. Palmer Luckey is a relentless builder and original thinker. He founded Oculus, bringing virtual reality to the mainstream, and is now reshaping the future of defense and technology with Anduril. I hope you enjoy this conversation. Palmer is the founder of Anduril, which makes next-generation military technology for the US and its al

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    Martín Escobari - Inside General Atlantic

    Published Nov 25, 2025

    My guest today is Martín Escobari. Martín is Co-President and Head of Global Growth Equity at General Atlantic. We talk about General Atlantic’s unique founding story and how its long-term structure, including permanent capital, a single P&L, and partnership culture, allows it to invest differently than other growth equity firms. We discuss the firm’s global perspective and particularly why the premium on U.S. equities is creating compelling opportunities across international and emerging market

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    Ari Emanuel - The Anti-AI Bet

    Published Nov 19, 2025

    My guest today is Ari Emanuel. Ari runs one of the most influential portfolios in global sports, entertainment, and media. He oversees TKO, which includes the UFC and WWE, serves as the Executive Chairman of WME Group, and recently founded MARI, a new company focused on global events and live experiences. At the center of this conversation is Ari's anti-AI bet: as AI makes digital content cheaper and everyday work more automated, he believes the value will increasingly concentrate in live and ph

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    Wolfgang Hammer - The Power of Story

    Published Nov 11, 2025

    My guest today is my friend Wolfgang Hammer. Wolfgang is a successful film producer and executive who helped create House of Cards and ran several major studios, including Lionsgate, CBS Films and Miramax. He’s now building a new kind of film studio with support from Mitch Lasky and Marc Andreessen. Wolfgang also helps founders and CEOs use storytelling to better understand what they do, and why it matters. In many ways, this conversation is a manual for how to find that story and communicate it

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    Luca Ferrari - Building Bending Spoons

    Published Nov 4, 2025

    My guest today is Luca Ferrari. Luca is the co-founder and CEO of Bending Spoons, which he describes as 25 percent private equity and 75 percent technology company. Founded in 2013, Bending Spoons fully acquires and operates digital companies like Evernote, Meetup, Vimeo, and most recently AOL. Our conversation explores the unique model behind Bending Spoons, and the culture required to scale it. Luca shares exactly how their acquisition playbook works – from identifying promising businesses to

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    Kevin Kelly - Be Generous and Unique

    Published Oct 31, 2025

    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. Kevin Kelly⁠ co-founded Wired magazine and has published a number of seminal books and essays on technology over the past three decades. I have devoured everything Kevin has put out into the world and many of his ideas shape the way I live today. Our conversation explores media, family, money, his concept of the Technium, AI, and mo

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    Ken Langone - The American Dream

    Published Oct 30, 2025

    Today I am replaying my conversation with Ken Langone. Ken is a legendary American businessman best known for his co-founding of Home Depot. He is also a former director of the New York Stock Exchange and a passionate philanthropist. He shares with us a lifetime worth of wisdom, building Home Depot into a powerhouse and prioritizing his employees above all else. He says he still “bleeds orange” to this day. You’ll hear as he recounts his business endeavors, his strict belief in keeping your word

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    Karim Atiyeh - Building Ramp

    Published Oct 21, 2025

    My guest today is Karim Atiyeh. Karim is the co-founder and CTO of Ramp, the fastest-growing finance automation platform in history, reaching over $1 billion in revenue in just over five years. Ramp is, of course, also our presenting sponsor, so I’m obviously very biased in how highly I think about Ramp and about Karim. But, this interview was not part of that sponsorship, I simply view Karim as one of the best operators active today. Ramp is building what Karim calls "self-driving finance"—usin

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    Dan Wang - The US vs China In The 21st Century

    Published Oct 16, 2025

    My guest today is Dan Wang. Dan is a technology analyst and author who spent six years living in China studying its manufacturing ecosystem and tech development, best known for his new book Breakneck. Dan offers the most nuanced framework I've encountered for understanding US-China competition. We explore a critical asymmetry: it's far harder for the US to rebuild manufacturing capacity than for China to improve scientific research, with profound implications for AI, national security, and inves

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    Jesse Zhang - Building Decagon

    Published Oct 6, 2025

    My guest today is Jesse Zhang. Jesse is the co-founder and CEO of Decagon, one of the fastest-growing AI customer service companies. Decagon provides a centralized AI engine to auto-resolve issues at any time, in every language, and across every channel. Jesse shares his systematic approach to finding product-market fit by asking potential customers exactly how much they'd pay for solutions. We explore why customer service and coding have emerged as the two clearest AI use cases for enterprises,

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    Dylan Patel - Inside the Trillion-Dollar AI Buildout

    Published Sep 30, 2025

    My guest today is Dylan Patel. Dylan is the founder and CEO of SemiAnalysis. At SemiAnalysis Dylan tracks the semiconductor supply chain and AI infrastructure buildout with unmatched granularity—literally watching data centers get built through satellite imagery and mapping hundreds of billions in capital flows. Our conversation explores the massive industrial buildout powering AI, from the strategic chess game between OpenAI, Nvidia, and Oracle to why we're still in the first innings of post-tr

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    Rolex: Timeless Excellence

    Published Sep 26, 2025

    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. This Business Breakdowns on Rolex is a long-time stand out. The founder and executive chairman of Hodinkee, Ben Clymer, was the perfect person to take us through the ins and outs of this legendary brand. For the full show notes, transcript, and links to the best content to learn more, check out the episode page ⁠here⁠. ----- This ep

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    Barry Diller - Building An Entertainment Empire

    Published Sep 23, 2025

    My guest today is Barry Diller. Barry is the former CEO of Paramount Pictures, Fox Broadcasting, and the founder of IAC. He has been at the center of every major media transformation over the past five decades, from creating the Movie of the Week format to building the fourth broadcast network to executing 150 internet-era deals. Barry reveals his "creative conflict" philosophy - pushing smart, opinionated people past their endurance point to generate breakthrough ideas. He also shares stories o

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    Jeff Horing - Building Insight Partners

    Published Sep 16, 2025

    My guest today is Jeff Horing. Jeff cofounded Insight Partners and has been the Managing Director since 1995. This is one of Jeff’s first public conversations about building one of the world’s most successful technology investment firms with over $100 billion in AUM. Jeff reveals the mechanics behind Insight's legendary sourcing machine—60-80 people systematically calling companies worldwide. He explains their contrarian "one fund" strategy that deploys $12 billion across everything from $10M gr

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    Sam Hinkie - Find Your People

    Published Sep 9, 2025

    Today, we are replaying one of my favorite conversations with Sam Hinkie. Sam worked for more than a decade in the NBA with the Houston Rockets and then as the President and GM of the Philadelphia 76ers. And now, after years of personal investing, he has launched his own venture capital firm, 87 Capital. Every conversation I have with Sam is alive with insight, and this one is no different. We explore the idea of studying the "breadcrumbs" that someone leaves behind as a way to track their progr

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    Sean Feeney - Reinventing the Restaurant Business

    Published Sep 5, 2025

    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. Sean Feeney makes you want to be a better person, friend, and leader. Sean is the co-founder of Grove House Hospitality Group and the owner of Lilia and Misi, two of New York City’s most sought-after restaurants. He left his job in Trading to chase down a dream with Michelin star chef Missy Robbins. Sean leveraged his finance backgr

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    Justin Ishbia - Lessons from Acquiring 586 Companies

    Published Sep 2, 2025

    Today we are replaying my conversation with Justin Ishbia. Justin is the Founding Partner of Shore Capital. Shore is a private equity firm that invests in microcap businesses within industry niches. With $7 billion in capital deployed but an average transaction size of just $12 million, Justin has worked to build a system to drive success for hundreds of businesses through replicable operating procedures and championing young professionals. The firm has created a moat around volume with nearly 6

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    Joe Liemandt  - Building Alpha School, and The Future of Education

    Published Aug 26, 2025

    My guest today is Joe Liemandt. Joe is the Principal at Alpha School and the founder of Triliogy Software and ESW Capital. He became the youngest member of the Forbes 400 in the 1990s before vanishing from public view for two decades—only to emerge with a $1 billion bet that he can make kids learn 10x faster using AI. Joe has built an AI tutoring system so effective that students at his Alpha School literally beg not to take summer breaks, achieving 2x learning outcomes in just 2 hours with stan

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    Mark Bertolini - Performance During Pain

    Published Aug 19, 2025

    My guest today is Mark Bertolini. Mark is the former CEO of Aetna and the current CEO of Oscar Health. He shares one of the most extraordinary leadership stories I've encountered—surviving a catastrophic skiing accident that left him in chronic pain for 18 years while simultaneously leading one of healthcare's most successful corporate turnarounds. His personal experience navigating his son's life-threatening cancer battle and his own medical challenges fundamentally changed his approach to heal

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    Peter Lacaillade - Backing The Best Managers In Private Markets

    Published Aug 12, 2025

    My guest today is Peter Lacaillade. Peter is the Chief Investment Officer for Private Investments at SCS Financial and has built a notable private equity allocation platform within the wealth management industry. He shares his insights on how SCS's pooled vehicle structure has enabled them to compete with institutional giants, avoiding the adverse selection that plagues most wealth platforms. Peter shares his investment philosophy across lower middle market buyouts, emerging independent sponsors

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    Andrew Milgram - Full-Contact Capitalism

    Published Aug 5, 2025

    My guest today is Andrew Milgram. Andrew is the founder of Marblegate Asset Management, an alternative investment firm that invests in credit opportunities and special situations. He joins me to discuss his unique approach to distressed investing in the middle market, revealing how middle market EBITDA has declined 20-25% since 2019, creating what he calls the "K-shaped economy." His investment stories are legendary, particularly his $600+ million bet on NYC taxi medallions, which we go into in

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    Ramtin Naimi - Building Abstract

    Published Jul 29, 2025

    My guest today is Ramtin Naimi. Ramtin is the founder of Abstract Ventures, one of the most talked-about seed funds in Silicon Valley. What makes Ramtin's story so compelling isn't just his firm's remarkable track record—including early investments in Rippling, Solana, and dozens of unicorns—but also the unconventional path he took to get there. From running a hedge fund straight out of high school to filing for bankruptcy at 24, then bootstrapping his way to building a $2 billion AUM venture fi

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    Zach Dell - Powering the Future

    Published Jul 22, 2025

    My guest today is Zach Dell. Zach is the co-founder and CEO of Base Power Company. Base is a modern power company building a reliable and affordable home energy service powered by distributed batteries. We explore one of the most underappreciated machines in our world: the electrical grid. Zach walks us through the complex world of electricity infrastructure and explains why the 100-year-old grid is woefully unprepared for the explosion in demand coming from AI, electric vehicles, and industrial

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    Alan Waxman - Building Sixth Street

    Published Jul 15, 2025

    My guest today is Alan Waxman. Alan is the co-founder and CEO of Sixth Street, one of the most unique investment firms with a "go anywhere, do anything" mandate across asset classes, geographies, and time horizons, and over $110 billion in AUM. He describes his journey from CIO of Goldman Sachs’ Special Situations Group and the frameworks he brought with him to lay the foundation for Sixth Street. Alan details their famous investments like Spotify and Airbnb during challenging periods, their inn

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    Caryn Seidman-Becker: Rebuilding CLEAR

    Published Jul 8, 2025

    My guest today is Caryn Seidman-Becker. Caryn is the Chairman and CEO of Clear. She bought the company out of bankruptcy for $6 million in 2010 and built it into the identity platform millions use in airports and stadiums today. Her Wall Street background investing in Apple, Amazon, and Priceline taught her to recognize when products become platforms, which shaped her vision for Clear as the "definitive secure identity platform" far beyond travel. Caryn shares the gritty early days of literally

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    Jens Grede - Building SKIMS

    Published Jul 1, 2025

    My guest today is Jens Grede. Jens is the co-founder and CEO of Skims, the shapewear and clothing brand he co-founded with his wife Emma Grede and Kim Kardashian. Our conversation left my head spinning. Jens has this remarkable ability to be both creative and commercial. He puts brilliant frameworks into plain terms and knows consumer like the back of his hand. Jens explains how pop culture is the only remaining hack to the consumer economy in our fragmented media landscape and describes today’s

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    Charlie Songhurst – Lessons from Investing in 483 Companies

    Published Jun 27, 2025

    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. Charlie Songhurst is a brilliant strategist, accomplished executive, and prolific angel investor. This episode is one of my all-time favorite conversations, not just on the podcast, but period. Please enjoy this timeless discussion with Charlie Songhurst. For the full show notes, transcript, and links to mentioned content, check out

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    The Chainsmokers - Music & Markets

    Published Jun 24, 2025

    My guests today are Alex Pall and Drew Taggart, who you might know as The Chainsmokers. We explore their fascinating evolution from scrappy DJs to global superstars to serious venture capitalists with their fund Mantis. Drew and Alex share how the same high-touch, relationship-driven approach that built their music empire now defines their investment philosophy. Their framework for backing founders mirrors their artistic process: they invest in obsessive individuals who will pursue their vision

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    Jay Hoag - Keys to Successful Growth Investing

    Published Jun 17, 2025

    My guest today is Jay Hoag. Jay is the co-founder of Technology Crossover Ventures, known as TCV, which pioneered the growth investing category and has backed legendary companies like Netflix, Spotify, and Expedia over three decades. Jay explains how macro factors like regulation have become unexpectedly central to technology investing. He offers his contrarian take on today's market, arguing that consumer internet represents significant opportunity while most investors chase SaaS and AI deals.

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    Dinakar Singh - A Father’s Call To Action

    Published Jun 15, 2025

    My guest today is Dinakar Singh. Dinakar is the founder and CEO of Axon, the family office successor to TPG-Axon, which was a successful global long-short hedge fund. We wanted to share his story on Father’s Day to honor the person and the dad that Dinakar is. He shares one of the most extraordinary stories at the intersection of finance and medicine I've ever encountered. This conversation explores the highest-stakes investment themes—timing, concentrated conviction, exceptional team building,

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    Bill Gurley - The Gift and The Curse of Staying Private

    Published Jun 10, 2025

    My guest today is Bill Gurley. Bill was the general partner at Benchmark Capital. He joins me for his sixth time on Invest Like the Best with his most comprehensive market analysis yet, examining the realities reshaping venture capital. Bill tackles the uncomfortable math underlying today's venture returns, with companies staying private for far longer. He also walks through why no one—from GPs to LPs to founders—has proper incentives to mark assets accurately, creating a system-wide coordinatio

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    50X Season Two: Asurion

    Published Jun 6, 2025

    Today, we are dropping a special episode in the Invest Like the Best Feed. 50X is back, a fan favorite series from Will Thorndike and the team at Compounding Labs. Will's book, "The Outsiders," is one of the best business and investing books that you'll find. You'll hear him continuing his work in the hosting chair as he looks in detail at investments that have appreciated at least 50-fold.Season two features Asurion. Colossus is excited to partner with Will as he sits down with the management a

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    John Zito - Inside Apollo - [Invest Like the Best, EP.426]

    Published Jun 3, 2025

    My guest today is John Zito. John is the Co-President of Apollo Global Management. He shares how they've quietly built one of the most important financial institutions of our time, originating over $250 billion annually. John's thesis on the convergence of private and public markets - and Apollo's positioning to capture 100% of client portfolios rather than just alternatives allocations - offers a fascinating glimpse into where institutional investing is heading. We discuss the cultural and stra

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    Fidji Simo - Creating Delightful Consumer Experiences

    Published May 30, 2025

    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. In the midst of her transition to OpenAI, we are spotlighting the force that is Fidji Simo. She is the former CEO of Instacart and grew up in a small town in the South of France and was the first person in her family to graduate from high school. Since then, she has had a dazzling career with stops at France’s leading university, eB

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    Graham Weaver - Building Alpine

    Published May 27, 2025

    My guest today is Graham Weaver. My guest today is Graham Weaver. Graham is the founder of Alpine Investors, a large private equity firm targeting an interesting market inefficiency. Alpine focuses on the thousands of $20 million revenue businesses whose baby boomer owners want to retire, but lack succession plans. Alpine buys companies and installs 28-year-old military veterans and top MBA graduates as CEOs, leveraging 25 years of intellectual property on how young executives can successfully r

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    Gustav Söderström - How Spotify Thinks

    Published May 20, 2025

    My guest today is Gustav Söderström. Gustav is the Co-President, Chief Product Officer & Chief Technology Officer at Spotify. Gustav lets us behind the scenes on how Spotify thinks about the future of audio and video, and what leadership lessons he's learned from making mistakes and taking risks in a rapidly changing technological landscape. He shares fascinating insights on their synchronized team structure and how they have positioned themselves as "the R&D department" for the entire music ind

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    Asurion: The Early Days (‘95-‘01) with Kevin Taweel

    Published May 16, 2025

    Kevin Taweel

    Today, we are dropping a special episode in the Invest Like the Best feed. You will hear the first episode of ⁠50X⁠ Season Two – a series from Will Thorndike and the team at Compounding Labs, in partnership with Colossus. This episode is the first in a series of three on Asurion, the world’s leading tech care company with more than 300 million customers. In an interview with Co-Founder and Chairman ⁠Kevin Taweel⁠, we explore Asurion’s scrappy origins in roadside assistance, acquisitive entry int

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    Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

    Published May 13, 2025

    My guests today are Rick Ruback and Royce Yudkoff. Rick and Royce are Harvard Business School professors who teach their students how to search for, acquire, and run small business directly after graduation. It has been almost a decade since our first conversation, and unlike many past interviews that have become outdated due to technology or market changes, the core principles they shared about entrepreneurship through acquisition remain remarkably relevant today. They explore fascinating devel

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    David Senra - The Focused Few

    Published May 6, 2025

    My guest today is David Senra. David is the host of Founders podcast and a dear friend. This is our third time doing Invest Like the Best together and we have conversations like this one all the time. In today’s episode, David distills wisdom from 400 entrepreneur biographies into a single word: focus. He reveals why exceptional builders like Todd Graves and James Dyson create billion-dollar empires through obsessive dedication to simple ideas—whether perfecting chicken fingers or designing vacu

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    Cliff Sosin - Investing in Carvana

    Published Apr 29, 2025

    My guest today is Cliff Sosin. Cliff is the founder of CAS Investment Partners, a fund he started with $5 million in 2012 and has grown to $1.7 billion as of the last reported numbers at the end of 2024. At the time, CAS had only four positions. This conversation is different to our typical episodes. We start by talking about Cliff's investing philosophy but the bulk of this long discussion is a case study into his remarkable investment in Carvana. Cliff is one of the biggest investors in the bu

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    Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]

    Published Apr 25, 2025

    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. There aren't many people like Cyan Banister. Her life story is remarkable. She was homeless at a young age, dropped out of high school, and five years ago she suffered an extremely rare stroke. Yet, in spite of everything, she is one of the most optimistic and curious people you can hope to meet. Cyan is also one of the great angel

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    Matt Huang - Investing At The Frontier

    Published Apr 22, 2025

    My guest today is Matt Huang, co-founder of Paradigm, a leading crypto investment firm with over $12 billion in assets under management. Before launching Paradigm in 2018 with Coinbase co-founder Fred Ehrsam, Matt was a partner at Sequoia Capital, where he led many of the firm's crypto investments. It’s widely reported that Michael Moritz called Matt “the only regrettable loss in Sequoia’s history.”In our conversation, Matt shares his framework for navigating the often illegible frontier of cryp

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    Neil Mehta - Finding Future S&P 500 Companies

    Published Apr 15, 2025

    Today's guest is Neil Mehta, founder of Greenoaks Capital. In 2012, aged 27, Neil left D.E. Shaw to start Greenoaks with his friend Benny Peretz. One of their first investments was in Coupang, a South Korean e-commerce company led by founder Bom Kim. Neil was so convinced of Coupang's potential that he invested 40% of their initial $50 million fund into the company—a bet that eventually returned about $8 billion.Over its first 13 years, Greenoaks has backed legendary companies like Figma, Wiz, C

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    Michael Ovitz - Turning Potential into Prominence

    Published Apr 8, 2025

    My guest today is Michael Ovitz. Michael is the legendary talent agent and Co-Founder of CAA or Creative Artists Agency and he is joining me on Invest Like the Best for a second time. Michael started CAA in 1975 and over the next 20 years, he built it into the world's most formidable talent agency, changing Hollywood forever. He shares insights into how he identifies exceptional people across diverse fields - from Hollywood directors like Steven Spielberg to tech founders like Alex Karp of Palan

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    Darren Farber - The Business of Defense

    Published Apr 1, 2025

    My guest today is Darren Farber. Darren is a Managing Partner of Albion River, a private direct investment firm focused on acquiring companies that produce highly technical Defense Products & Services. He is a Former special advisor to the Deputy Under Secretary of Defense, a Former member of U.S. Department of Defense Task Force for Business and Stability Operations, and the list goes on and on. Darren is a wealth of knowledge in this space and someone I am grateful to have in the US corner. He

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    Josh Kushner - Building Thrive Capital

    Published Mar 28, 2025

    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

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    Gili Raanan - Cybersecurity Investment Playbook

    Published Mar 25, 2025

    My guest today is Gili Raanan. Gili is the founder of Cyberstarts, a VC firm focused on cybersecurity and the world’s first VC that is majorly backed by cyber entrepreneurs. Cyberstarts’ $50 million dollar first fund exploded to close to $2 billion in just three years. Gili describes cybersecurity today as "the perfect storm" where global conflicts and AI advancements are creating unprecedented threats. He talks about Cyberstarts' "Sunrise" methodology, which uniquely identifies customer pain po

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    Alex Wiltschko - Giving Computers A Sense Of Smell

    Published Mar 18, 2025

    My guest today is Alex Wiltschko. Alex is the founder and CEO of Osmo, a science and technology company giving computers a sense of smell. He set out on a mission to digitize our sense of smell and he describes how Osmo is teaching computers to both read and write scent. Alex was kind enough to walk me through the laboratory which you can watch in the video version of this interview on Youtube and Spotify, where he demonstrates their method to the madness. We discuss their first commercial appli

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    Kelly Granat - Investing At Lone Pine

    Published Mar 11, 2025

    My guest today is Kelly Granat. Kelly is the Co-Chief Investment Officer and Managing Director at Lone Pine Capital, one of the most storied and successful hedge fund and investment firms of the last several decades. We explore how investing has evolved since Kelly joined the industry and she shares insights into Lone Pine maintaining its edge through deep fundamental research and a collaborative culture. We discuss what makes great businesses and great investments, how leadership can transform

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    Devon Zuegel: How To Create A New Town

    Published Mar 4, 2025

    Devon Zuegel

    Devon Zuegel: How To Create A New Town - [Invest Like the Best, EP.413]My guest today is Devon Zuegel. Devon is the founder and president of the Esmerelda Institute, and she is creating a new town called Esmerelda in California wine country. Learning of Devon and her plan, I couldn’t help but wonder why there aren’t more people building new towns. She shares the origin story of her project Esmeralda, a modern reinvention of the Chautauqua community she cherished growing up, and we explore her fa

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    Doug Leone - Lessons from a Titan

    Published Feb 28, 2025

    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. There's nobody I've met quite like Doug Leone.Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion g

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    Chris Pedregal - Building Granola

    Published Feb 25, 2025

    My guest today is Chris Pedregal. Chris is the founder and CEO of Granola, an AI-powered notepad that transcribes your meetings and enhances your meeting notes. Chris shares fascinating insights on how humans have historically developed tools to extend our cognitive capabilities - from writing and mathematical notation to data visualization - and how AI represents the next frontier in this evolution. We explore competitive dynamics between model providers and application builders, and Chris shar

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    Ravi Gupta - AI or Die

    Published Feb 18, 2025

    My guest today is Ravi Gupta. Ravi is a Partner at Sequoia Capital and a host on Glue Guys, a podcast on the Colossus network that intersects business and sports. I wanted to have him back on Invest Like the Best to discuss his recent most recent blog post titled “AI or Die.” As both an investor and former Instacart operator and CFO, Ravi believes we're entering an era where the constraints that historically limited small teams are dissolving, creating unprecedented opportunities for those willi

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    Marc Andreessen - The Battle For Tech Supremacy

    Published Feb 11, 2025

    My guest today is Marc Andreessen. Marc is a co-founder of Andreessen Horowitz and one of Silicon Valley's most influential figures. He combines deep technical knowledge from his engineering background with broad historical understanding and strategic thinking about societal patterns. He last joined me on Invest Like the Best in 2021, and the playing field looks a lot different today. Marc goes deep on the seismic shifts reshaping technology and geopolitics. We discuss DeepSeek's open-source AI

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    Graham Duncan - Talent Whisperer

    Published Feb 4, 2025

    My guest today is Graham Duncan. This conversation will make you think about your life in new ways. This is a two-hour segment of a 4.5-hour interview I did with Graham last year. It stands alone as remarkable, but those who subscribe to Colossus Review will gain access to the full conversation. This will be true in future issues, too.In 2006, in his early 30s, Graham convinced Stuart Miller, CEO of home construction company Lennar, to let him manage $50 million of his family's wealth. A year la

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    Blake Hall - Combat, Service, and Innovation

    Published Jan 28, 2025

    My guest today is Blake Hall. Blake is the co-founder and CEO of ID.me, a secure digital identity network with over 100 million members. He was an officer in the United States Army and served our country for four years as a a rifle platoon leader, the battalion reconnaissance platoon leader, and as the battalion logistics officer. We explore his formative years in the military and transition into entrepreneurship. Blake shares powerful stories from his time leading scout sniper missions in Iraq,

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    Dylan Field - Designing The Future

    Published Jan 21, 2025

    My guest today is Dylan Field. Dylan is the co-founder and CEO of Figma and last joined me on Invest Like the Best in 2020. A lot has changed since then and we explore the evolving landscape of design and how Figma has been navigating AI while staying true to its founding vision of eliminating the gap between imagination and reality. Despite Figma's incredible success in becoming the default design platform, Dylan remains deeply motivated by helping users achieve their goals. He shares fascinati

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    Tal Zaks - Bridging Science, Medicine, and Returns

    Published Jan 14, 2025

    My guest today is Tal Zaks. Tal is a physician-scientist turned biotech executive and investor who served as Moderna's Chief Medical Officer during their COVID-19 vaccine development, giving him an extraordinary perspective on one of modern medicine's pivotal moments. His combination of medical expertise, platform innovation experience, and investing acumen allows us to explore the interconnected challenges of turning scientific breakthroughs into viable medicines while generating venture-scale

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    Gaurav Misra & Dwight Churchill - Building Captions

    Published Jan 7, 2025

    My guests today are Dwight Churchill and Gaurav Misra, co-founders of Captions, which uses AI to generate and edit talking videos and has grown to significant scale at remarkable speed. We explore a key distinction in AI: tackling bounded problems like video generation versus unbounded problems like general intelligence and what this means for building sustainable businesses. We also explore their unique data flywheel, why video generation could reach Hollywood quality within 18 months, and why

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    Jack Kokko - Building AlphaSense

    Published Dec 31, 2024

    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 with the advent of large language models to change the research experience completely. He speaks to their recent acquisition of Tegus earlier this year, reshaping the business and further supporting their expansion to serve all types of companies instead of exclusively investment f

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    Jared Kushner - The Mechanic

    Published Dec 20, 2024

    My guest today is Jared Kushner. Jared has lived more lives than just about anyone I know his age. He ran Kushner companies for years, investing in real estate in and around New York City. He owned the New York Observer. He was a senior advisor to President Trump in his first term. He now runs Affinity Partners, which we discuss in detail, a private equity firm built to find and execute unique investments around the world that stem from Jared's unique set of experiences in business and governmen

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    Scott Wu - Building Cognition

    Published Dec 17, 2024

    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 functions at the level of a junior software engineer, capable of handling complete engineering workflows from bug fixing to submitting pull requests. He is a former competitive programming champion and describes the field as simply “the art of telling the computer what you want i

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    Micky Malka - Building Ribbit

    Published Dec 10, 2024

    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 visionary approach and a believer in killing the thing that got you to where you are in pursuit of what’s next. We discuss his perspective on fintech’s evolution and why his firm boldly declares that “fintech is dead.” We dive into his theory of the "grid," which examines how knowledge

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    Chetan Puttagunta and Modest Proposal - Capital, Compute & AI Scaling

    Published Dec 6, 2024

    My guests today are Chetan Puttagunta and Modest Proposal. Chetan is a General Partner at venture firm Benchmark, while Modest Proposal is an anonymous guest who manages a large pool of capital in the public markets. Both are good friends and frequent guests on the show, but this is the first time they have appeared together. And the timing couldn’t be better - we might be witnessing a pivotal shift in AI development as leading labs hit scaling limits and transition from pre-training to test-tim

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    Ronnie Fieg - Building Kith

    Published Dec 3, 2024

    My guest today is Ronnie Fieg, founder and CEO of Kith. At age 13, Ronnie started working at David Z., an iconic New York shoe store, where he sold Timberland boots to Jay-Z and Wallabies to Wu-Tang Clan. He worked his way up from the stockroom and earned his first collaboration in 2007, when he worked with ASICS on new Gel-Lyte 3s. That collection sold out in a day after being featured in The Wall Street Journal, catching the attention of Adidas's president and launching his reputation as a cul

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    Gabe Whaley - Building MSCHF

    Published Nov 26, 2024

    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 microscopic handbags—the size of a grain of salt—to tax software that helps you file your returns by going on virtual dates with anime characters.Every two weeks, they release something new that challenges our assumptions about art, commerce, and culture. MSCHF is hard to define but Gabe

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    Brad Jacobs - Think Big and Move Fast

    Published Nov 22, 2024

    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 and raised $30 billion dollars of debt and equity capital. Currently, he is the Executive Chairman of XPO, a commercial trucking company that he started in 2011 and has grown into one of the largest logistics businesses in the world. He has also written a book that will be out in