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Invest Like the Best with Patrick O'Shaughnessy

Colossus | Investing & Business Podcasts

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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.joincolossus.com
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Welcome to the third episode of Section F - our Spy Movie Podcast track on Spybrary. Our Section F handpicked hosts and guests discuss their favourite spy movies both the classics and the hidden gems of spy films. Today Spybrary's Section F delve into the 1963 movie adaptation of Ian Fleming's From Russia With Love starring Sean Connery and directe…
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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 …
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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 thro…
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Is the German Spy Museum in Berlin worth your time? In this episode of Brush Pass on Spybrary, we take you inside this fascinating espionage attraction to uncover its best exhibits, hidden gems, and whether it’s a must-visit for spy fans. Spybrary’s on-the-ground team in Berlin – Station C's Matt Batten, David Morgan, and Father Richard Green – sha…
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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.…
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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 b…
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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 h…
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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 …
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Ever wonder what spy novels a real-life Special Forces and CIA operative can't put down? Former Special Forces & CIA Officer James Stejskal reveals his top five spy thrillers on Spybrary's Dead Drop 5. The Dead Drop 5 is back! In this much-requested Spybrary feature, our guest is embedded behind the Iron Curtain and can request five spy books, a ga…
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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 playi…
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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 …
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🔎 "Most mole hunts end in an unsatisfying fashion…" – David McCloskey Former CIA analyst-turned-bestselling spy novelist and The Rest is Classified Podcast Host David McCloskey returns to Spybrary for an illuminating conversation with journalist and espionage fan The Sunday Times' Chief Political Commentator Tim Shipman. From Langley’s shadowy corr…
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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 fo…
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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'…
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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 investi…
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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 buil…
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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 Tegu…
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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 privat…
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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 submit…
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Welcome to our book club episode on On Her Majesty’s Secret Service, Ian Fleming's eleventh James Bond novel and one of the most pivotal in the series. Spybrary host Shane Whaley introduces this James Bond Book club episode from the steps of the College of Arms in London, a location that plays a significant role in the story as Bond takes on a uniq…
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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 perspecti…
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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’…
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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…
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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 cha…
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Shane Whaley engages in a riveting discussion with historian and author Dr. Claire Hubbard-Hall. Known for her expertise in the history of women in intelligence, Claire brings to light the overlooked yet monumental roles women have played in British Intelligence. Her book titled Her Secret Service - The Forgotten Women of British Intelligence aims …
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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 co…
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Wilfred "Biffy" Dunderdale: A Life of Espionage On today's Spybrary, host Shane Whaley sat down with Lt. Col. Tim Spicer OBE, author of A Suspicion of Spies: Risk, Secrets and Shadows – The Biography of Wilfred ‘Biffy’ Dunderdale. The book offers a glimpse into the life of this iconic British spy. Drawing upon years of research, Spicer's biography …
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My guest today is Ernie Garcia. Ernie is the co-founder and CEO of Carvana. Ernie joined me on Founder’s Field Guide in 2021 and despite all that the business has gone through since that conversation, you’ll hear how he has the exact same demeanor and crystal clear vision for the business and its operations today. Carvana is one of the most remarka…
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My guests today are Andrew Homan and Chris Miller. Andrew has spent two decades at Maverick Capital and is a managing partner at Maverick Silicon, where he leads the firm’s technology investments. Chris is a professor at Tufts and the author of the New York Times best-selling book “Chip War,” which details the geopolitical battle to control the sem…
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‘Compelling and meticulously researched, the riveting life of a maverick Scottish spy.’ Charles Cumming Sir Robert Bruce Lockhart, a Scottish diplomat, spy and writer, led a life filled with adventure and intrigue. While his involvement in the famed Lockhart Plot of 1918 is often cited, there is much more to uncover about Robert Bruce Lockhart's li…
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My guest today is Boyd Varty. Boyd is a lion tracker, life coach, and storyteller who grew up in the South African wilderness, living amongst and tracking wild leopards. This is his fourth time on Invest Like the Best but the first in six years. Boyd is a perfect follow-up to my episode with Lulu Meservey unpacking the intricacies of storytelling a…
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Karla's Choice sees the return of John le Carré's George Smiley. Today we're joined by his son, the author Nick Harkaway, along with John le Carré fans Steve Ritterman and Matthew Bradford, Our host Shane Whaley hosts this fascinating discussion about Harkaway’s foray into his father John le Carré's iconic universe, particularly his latest novel Ka…
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My guest today is Tobi Lutke, the co-founder and CEO of Shopify. I have spoken to Tobi on this podcast twice before, first in 2020 and then again in 2022. Needless to say, a lot has changed since we last spoke, and we start by talking about the biggest change of all: AI. But I’ll remember this conversation for the next set of ideas we discuss: Foun…
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We have made it to Episode 250! Hear this special message from Spybrary founder Shane Whaley talking about Spybrary's future as well as a fun conversation Spybrarians, I need your intel! Eight years ago, I never imagined I'd be here, asking this question. When I launched the Spybrary Podcast, I had no idea we'd build a community of fellow spy enthu…
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My guests today are Matt Perelman and Alex Sloane, Co-founders and Managing Partners of Garnett Station Partners. GSP invests in the trillion-dollar franchise and consumer services industries. Matt and Alex started the firm in 2014 as MBA students when they bought 23 Burger King restaurants. Since then, they've invested in 26 other multi-unit busin…
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My guest today is Kareem Zaki. Kareem is a General Partner at Thrive Capital and has been at the firm for a decade. In an episode last year, Thrive's founder, Josh Kushner, told me he is the best healthcare investor in the world. Kareem has co-founded three healthcare businesses worth over one billion dollars. He also has expertise in financial ser…
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In this fascinating episode of the Spybrary Spy History Podcast, host Adam Brookes interviews Barry Werth author of Prisoner of Lies: Jack Downey's Cold War. This remarkable true cold war spy story of the longest-held prisoner of war in American history, John Downey, Jr., a CIA officer captured in China during the Korean War and imprisoned for twen…
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My guest today is Ray Ozzie, one of the great technologists, software developers, and entrepreneurs of our time. Ray is perhaps best known as the creator of Lotus Notes, a collaboration tool that revolutionized business communication in the 1990s. He later succeeded Bill Gates as Chief Software Architect at Microsoft, where he played a key part in …
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Prepare to experience Ian Fleming's James Bond novels as if reading them for the first time in the year of publication as we embark on this 007 James Bond literary adventure together. Shane Whaley - Spybrary Podcast Host Are you a fan of the Ian Fleming James Bond books? If so, you won't want to miss the latest episode of the James Bond Book Club p…
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My guest today is Ted Seides. Ted is the host of the Capital Allocators podcast and an investment industry expert. It’d been seven years since Ted and I last talked on the record, as he was one of my very first guests on Invest Like the Best. Now that Ted has a full-time focus on all things Capital Allocators and has stepped away from traditional i…
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In this riveting episode of the Spybrary Spy Podcast, guest host David Clark is joined by author and investigative journalist Tim Tate to dissect his latest espionage non-fiction book To Catch A Spy which examines the enigmatic and controversial history surrounding Roger Hollis, the former MI5 Director General, Margaret Thatcher, Peter Wright and t…
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My guest today is Lulu Meservey. Lulu is the Founder and CEO of Rostra, a company that partners with founders to level up their communications around all strategic initiatives, from hiring to fundraising. She is also on the board at Shopify. I have been recently fascinated by the challenge of founders telling their story and Lulu is an expert in co…
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In this captivating episode of the Spybrary Spy Podcast, join host Shane Whaley as he sits down briefly with the legendary actor Gary Oldman, who portrays the enigmatic Jackson Lamb in the hit TV adaptation of Mick Heron's "Slow Horses." Gary Oldman reveals how Jackson Lamb first appeared on his radar and the differences working with spy authors Mi…
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My guest today is Ric Elias. Ric 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 has grown it to now a global company with thousands of employee…
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A thrilling tick-tock recounting one of the most harrowing hostage situations and daring rescue attempts of our time—from the true-life espionage master and New York Times bestselling author of Operation Mincemeat and The Spy and the Traitor. Today on the Spybrary podcast, we're taking you inside the Iranian Embassy siege. Join us for a gripping ep…
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This week's episode is special because it marks the launch of a new Colossus show: Glue Guys. My guests this week are the hosts of the new show, Shane Battier, Alex Smith, and Ravi Gupta. Shane, Ravi, and Alex’s stories are remarkable. Each has been at the very top of their profession. Shane as an NCAA and NBA champion. Alex as the first pick in th…
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My guest today is Bret Taylor. His resume is absurd. He built google maps--famously rewriting the whole thing in a weekend. He was the CTO of Facebook in critical years. He founded Quip. He was the chair of the board at Twitter. He was the co-CEO of Salesforce...the incredible list goes on. Now, Bret is the co-founder of Sierra, a conversational AI…
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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. He is one of my favorite investors to talk to and this may be my favorite conversation with him. Gavin first started covering Nvidia as an investor at the turn of the millennium, making him the perfect gues…
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Today, we’re replaying a conversation between John Collison and Charlie Munger that we first aired on 5 December 2023. Charlie said, “The best thing a human being can do is to help another human being know more.” He does just that in this interview. Please enjoy, and may Charlie Rest in Peace. For the full show notes, transcript, and links to menti…
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On today’s episode, acclaimed spy authors Joseph Kanon and Paul Vidich sit down for an intriguing discussion that delves deep into the world of writing spy fiction. As many of you know, I’ve been lucky enough to share drinks, meals, and some unforgettable conversations with some of the best spy authors working today. And every time, I think to myse…
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