Invest Like the Best with Patrick O'Shaughnessy

Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money - [Invest Like the Best, EP.487] Aug 18, 2026 4576 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

Eric Vishria - A Decade of Lessons Investing in Software & Hardware - [Invest Like the Best, EP.486] Aug 11, 2026 3954 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

Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485] Aug 4, 2026 3904 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, con

Sam Altman - How to Make an Abundant Future - [Invest Like the Best, EP.484] Jul 28, 2026 3213 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 Huggi

Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483] Jul 21, 2026 3397 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

John Kim - How to Raise a Few Billion Dollars - [Invest Like the Best, EP.482] Jul 14, 2026 3020 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

Jeremy Giffon - The Billion Dollar PDF - [Invest Like the Best, EP.481] Jul 7, 2026 4519 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,

Etched - Building AI Hardware to Make Inference Faster and Cheaper - [Invest Like the Best, EP.480] Jun 30, 2026 5241 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 mor

Vlad Barbalat - Investing $120 Billion in Permanent Capital - [Invest Like the Best, EP.479] Jun 23, 2026 4177 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

Kareem Amin - The Unusual Approach to Company Building - [Invest Like the Best, EP.478] Jun 16, 2026 3401 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

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477] Jun 9, 2026 4247 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 tw

Dara Khosrowshahi - Uber's Bet on AVs, AI, and Building a Super-App - [Invest Like the Best, EP.476] Jun 3, 2026 4037 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.

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475] May 28, 2026 3783 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. W

Darren Farber on Iran, China, and the Rise of Neoprimes - [Invest Like the Best, EP.474] May 26, 2026 2779 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

Gavin Baker - Watts and Wafers - [Invest Like the Best, EP.473] May 20, 2026 4611 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 lon

Krishna Rao - Anthropic's CFO on Compute, Scaling to $30B ARR, and the Returns to Frontier Intelligence - [Invest Like the Best, EP.472] May 13, 2026 4567 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 a

Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.471] May 5, 2026 4523 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,

Paul Tudor Jones - Lessons From 50 Years in Markets - [Invest Like the Best, EP.470] Apr 28, 2026 4013 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

Dylan Patel - The Infinite Demand for Tokens, Claude Mythos, and Supply Constraints - [Invest Like the Best, EP.469] Apr 23, 2026 2719 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

Alex Karnal - The Trillion-Dollar Health Revolution - [Invest Like the Best, EP.468] Apr 21, 2026 5540 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

Scott Nolan - SpaceX, Founders Fund, and Rebuilding American Uranium Enrichment - [Invest Like the Best, EP.467] Apr 14, 2026 4558 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 quarte

Alan Waxman - Private Credit and the Modern Financial System - [Invest Like the Best, EP.466] Apr 8, 2026 3739 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, stu

Sergey Levine - Building LLMs for the Physical World - [Invest Like the Best, EP.465] Mar 31, 2026 3995 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 sc

Mitchell Green - Lessons from Cold Calling 10,000 Companies - [Invest Like the Best, EP.464] Mar 24, 2026 3262 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-

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] Mar 17, 2026 4250 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

Shyam Sankar - Celebrating Heretics - [Invest Like the Best, EP.462] Mar 10, 2026 4898 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"

John Arnold - China, Energy Markets and Fixing America's Systems - [Invest Like the Best, EP.461] Mar 4, 2026 4549 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

Dan Sundheim - The Art of Public and Private Market Investing - [Invest Like the Best, EP.460] Feb 24, 2026 4518 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 cas

Josh Kushner - Concentration and Conviction - [Invest Like the Best, EP.459] Feb 18, 2026 3784 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.

Alex Behring and Daniel Schwartz - Inside 3G Capital - [Invest Like the Best, EP.458] Feb 10, 2026 5749 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 the

Ben Horowitz - Backing America’s Future - [Invest Like the Best, EP.457] Feb 3, 2026 3351 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 sha

Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456] Jan 29, 2026 4562 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 compan

Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] Jan 20, 2026 7600 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, undisco

Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454] Jan 13, 2026 4448 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

Reed Hastings - Building Netflix - [Invest Like the Best, EP.453] Jan 6, 2026 3753 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 comp

Nick Kokonas - Know What You Are Selling - [Invest Like The Best, REPLAY] Dec 30, 2025 4667 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 th

Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS] Dec 23, 2025 5115 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 la

Henry Ellenbogen - Man Versus Machine - [Invest Like the Best, EP.452] Dec 16, 2025 6478 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

Gavin Baker - Nvidia v. Google, Scaling Laws, and the Economics of AI - [Invest Like the Best, EP.451] Dec 9, 2025 5133 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

David George - Building a16z Growth, Investing Across the AI Stack, and Why Markets Misprice Growth - [Invest Like the Best, EP.450] Dec 2, 2025 4021 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

Palmer Luckey - Inventing the Future of Defense - [Invest Like the Best, CLASSICS] Nov 28, 2025 4509 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. Pa

Martín Escobari - Inside General Atlantic - [Invest Like the Best, EP.449] Nov 25, 2025 4219 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 p

Ari Emanuel - The Anti-AI Bet - [Invest Like the Best, EP.448] Nov 19, 2025 3744 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

Wolfgang Hammer - The Power of Story - [Invest Like the Best, EP.447] Nov 11, 2025 2552 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

Luca Ferrari - Building Bending Spoons - [Invest Like the Best, EP.446] Nov 4, 2025 4895 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

Kevin Kelly - Be Generous and Unique - [Invest Like the Best, CLASSICS] Oct 31, 2025 4099 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

Ken Langone - The American Dream - [Invest Like the Best, REPLAY] Oct 30, 2025 3008 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

Karim Atiyeh - Building Ramp - [Invest Like the Best, EP.445] Oct 21, 2025 6362 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 o

Dan Wang - The US vs China In The 21st Century - [Invest Like the Best, EP.444] Oct 16, 2025 5767 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

Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443] Oct 6, 2025 4932 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 ex

Dylan Patel - Inside the Trillion-Dollar AI Buildout - [Invest Like the Best, EP.442] Sep 30, 2025 7155 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 strate

Rolex: Timeless Excellence - (Invest Like the Best, CLASSICS) Sep 26, 2025 3751 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, tran

Barry Diller - Building An Entertainment Empire - [Invest Like the Best, EP.441] Sep 23, 2025 3275 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, op

Jeff Horing - Building Insight Partners - [Invest Like the Best, EP.440] Sep 16, 2025 5531 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 e

Sam Hinkie - Find Your People - [Invest Like the Best, REPLAY] Sep 9, 2025 4738 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 exp

Sean Feeney - Reinventing the Restaurant Business - [Invest Like the Best, CLASSICS] Sep 5, 2025 6467 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 Tr

Justin Ishbia - Lessons from Acquiring 586 Companies [Invest Like the Best, REPLAY] Sep 2, 2025 4491 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 pro

Joe Liemandt - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439] Aug 26, 2025 8852 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 Scho

Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438] Aug 19, 2025 5934 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

Peter Lacaillade - Backing The Best Managers In Private Markets - [Invest Like the Best, EP.437] Aug 12, 2025 5517 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. Pete

Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436] Aug 5, 2025 5649 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 st

Ramtin Naimi - Building Abstract - [Invest Like the Best, EP.435] Jul 29, 2025 6830 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 scho

Brad Jacobs - Think Big and Move Fast - [Invest Like the Best, CLASSICS] Jul 25, 2025 5126 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. Brad Jacob's simple principle of "think big, move fast" is one I think about often. 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

Zach Dell - Powering the Future - [Invest Like the Best, EP.434] Jul 22, 2025 4985 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

Alan Waxman - Building Sixth Street - [Invest Like the Best, EP.433] Jul 15, 2025 4493 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.

Caryn Seidman-Becker: Rebuilding CLEAR - [Invest Like the Best, EP.432] Jul 8, 2025 5275 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 "defi

Jens Grede - Building SKIMS - [Invest Like the Best, EP.431] Jul 1, 2025 5480 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

Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS] Jun 27, 2025 4086 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

The Chainsmokers - Music & Markets - [Invest Like the Best, EP.430] Jun 24, 2025 4712 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 founder

Jay Hoag - Keys to Successful Growth Investing - [Invest Like the Best, EP.429] Jun 17, 2025 2759 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

Dinakar Singh - A Father’s Call To Action - [Invest Like the Best, EP.428] Jun 15, 2025 2869 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 explor

Bill Gurley - The Gift and The Curse of Staying Private - [Invest Like the Best, EP.427] Jun 10, 2025 4822 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

Asurion: 50X Season Two - (50X, S2) Jun 6, 2025 11689 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

John Zito - Inside Apollo - [Invest Like the Best, EP.426] Jun 3, 2025 4657 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

Fidji Simo - Creating Delightful Consumer Experiences - [Invest Like the Best, CLASSICS] May 30, 2025 4333 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

Graham Weaver - Building Alpine - [Invest Like the Best, EP.425] May 27, 2025 5457 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 gradua

Gustav Söderström - How Spotify Thinks - [Invest Like the Best, EP.424] May 20, 2025 5073 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 tea

Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423] May 13, 2025 5332 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 e

David Senra - The Focused Few - [Invest Like the Best, EP.422] May 6, 2025 4897 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 empir

Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421] Apr 29, 2025 7275 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

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