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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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Art of Investing

Colossus | Investing & Business Podcasts

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Art of Investing is a series of discussions with the world's best investors, company builders, academics, athletes, artists and human beings devoted to exploring the joys of compounding in all its forms.
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Making Markets

Colossus | Investing & Business Podcasts

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Making Markets explores the psychology and structure that make up markets all over the world. Each week, Eric Golden speaks to experts about a different market so you can see what actually happens when money changes hands. From mainstream stock and bond markets to esoteric niches like vineyards, antique art, and crypto, we explain the transactions that underpin our economy. Visit joincolossus.com to find more episodes, transcripts and a library of content to continue your learning.
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Making Media

Colossus | Investing & Business Podcasts

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How to build a media business by two outsiders learning the craft. Matt Reustle and Dom Cooke have decades of experience in investing but almost none in the media industry. In each episode, they talk to great media operators, document their own media building efforts, and dissect their favorite business content. Join these two content junkies in their fight to save long-form media against the attention span crisis. Join the resistance. Learn more and stay up to date at www.joincolossus.com. ...
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My guest this week is Bob Elliot, the CIO of Unlimited Funds. Before Unlimited, Bob was on the investment committee at Bridgewater and led Ray Dalio’s personal research team for a decade. I’m a big fan of Bob’s work and his twitter account and was excited to talk to him on all things Macro. We start by diving into the current market cycle and the U…
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My guest today is Pat Grady, a longtime growth investor at Sequoia and one of the firms senior leaders. Pat has been a part of a long list of legendary investments, ranging from Snowflake, Zoom, ServiceNow, Qualtrics, Okta, Hubspot, Notion, and OpenAI, among many others. There aren't many investors who reference as well at Pat, both inside and outs…
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My guest this week is Ben Gordon, the CEO of Fractal. At Fractal, Ben runs a unique strategy, providing farmers with equity capital and investors exposure to a differentiated and uncorrelated asset class. Ben starts by making the case for investing in farmland and explaining why institutional ownership remains low in the category. We then dive into…
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My guest today is Frank Blake. Frank is the former chairman and CEO of Home Depot. I recently interviewed Home Depot co-founder Ken Langone and became fascinated by the business’s impressive lineup of leaders through the decades. Frank led the company from 2007 to 2014 and shares how he carried on the legacy of Ken and the others, upholding their c…
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Today, we are replaying our conversation with Ho Nam, co-founder of Altos Ventures. As the numbers go, Altos is one of the greatest venture capital firms of the last quarter century. We unpack Ho's origin story and the values that shaped him most as a person and investor, and then we then turn to Altos itself. Altos has emerged as one of the most e…
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My guest this week is Adam Terry, the co-founder and CEO of Cantrip. A few weeks ago, Aaron Edelheit came on the show and made the pitch for investing in Cannabis Beverages. Today, we talk to one of the leading operators in this space. This was a fun conversation where we really got into the weeds, pun intended, into the science of a very complicat…
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My guest today is Adam Sandow. Adam is the chairman and CEO of SANDOW Companies and the executive chairman and founder of Material Bank. He has built an entire ecosystem of businesses and brands that have brought him into the game of media, materials, and beyond. From creating the beauty product subscription model to getting magazines in the hands …
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My guest today is Tony Cappell, the Founding Partner at Chicago Atlantic. In 2018, Tony saw an opportunity to do private credit in Cannabis and has since built Chicago Atlantic is the largest lender in the space. We start by talking about the early days of Chicago Atlantic. We then move on to the challenges of underwriting in Cannabis, his views on…
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My guest today is Howie Liu. Howie is the co-founder and CEO of Airtable, a no-code app platform that allows teams to build on top of their shared data and create productive workflows. The business began in 2013 and now has use cases built out for over 300,000 organizations. As Airtable begins to integrate AI and the latest LLMs into its product, H…
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My guest today is Tom Dunleavy. Tom spent a decade in traditional finance before moving onto Web3. Today he is the Managing Director of the Crypto VC firm MV Global. We start this conversation by exploring the current state of public and private crypto investing. Tom then outlines the process of raising capital, the role of Key Opinion Leaders, the…
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My guest today is Mark Groden. Mark is the Founder and CEO of Skyryse, a company on a mission to make general aviation as safe as commercial aviation and change the future of flying. As you may know, helicopter accidents are far more likely than airplane accidents, and Skyryse is revolutionizing helicopter flight through a safer and simpler univers…
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Today, we are revisiting our class with David Senra in honor of our upcoming event together. David is an absolute force of nature who is taking the world by storm with his podcast "Founders." In this class, we enjoy access to the full spectrum of learnings from his decade-long study of history's greatest entrepreneurs, artists, athletes, and leader…
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My guest today is Corey Kluber. For those who don’t follow baseball, Corey Kluber was a 3-time MLB all star and one of the great pitchers of the last decade. Today, he takes us on quick tour through his career and what it takes to succeed as an elite athlete. We also talk about the market for athletes, his strong views on childhood athletics, his p…
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Our guest today is Dan Shipper, the co-founder and CEO of Every. Every started at the beginning of the pandemic as a bundle of business newsletters written by different authors. While writing is still at the heart of the business, the model has shifted focus to a daily newsletter that is an essay on technology, productivity, or AI. Dan and his team…
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My guest today is Dev Ittycheria. Dev is the CEO of MongoDB, the developer data platform with tens of thousands of customers in 100 different countries. He joined the company as CEO in 2014, taking it public in 2017, and is now approaching a decade of leading MongoDB to become a go-to choice for the most sophisticated organizations around the world…
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Today’s teacher is Marcus Freeman, Head Football Coach at the University of Notre Dame. We discuss the power of relationships and how he talks with his players about the concepts of hard work and love, and we delve into what it takes to focus on inputs rather than outputs, especially as the college sports world is changing in unprecedented ways. Fo…
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My guest today is Nir Kaissar. Nir is the founder and portfolio manager at Unison Advisors and one of my favorite economic commentators/columnists at Bloomberg. Today, he joins us for a wide-ranging discussion on the US economy. We start with the disconnect between the strong economic numbers and the sentiment amongst the population. We then cover …
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My guest today is Nico Wittenborn. Nico is the founder of Adjacent, a venture firm that looks for what he describes as the “adjacent possible” for their next investment. Nico has zoned in on the consumer subscription market as his ideal candidate, making early investments in Calm App, Photoroom, and Oura Ring. Nico does virtually all steps of the i…
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My guest today is Aaron Edelheit, the CEO and Portfolio Manager at Mindset Capital. Aaron has spent his career practicing value investing in overlooked industries, like housing after the 2008 recession or Cannabis today. But we start the conversation by talking about another overlooked topic- burnout and the importance of disengaging from work. We …
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We are excited to share a great conversation with Mitch Rales, the co-founder of Danaher and one of the living legends in the world of business and investing. Consider that Danaher has annualized at over 21% for four decades, resulting in an 1800-times multiple on invested capital! This is Mitch's first long-form interview of any kind, and he cover…
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My guest this week is Marc Lasry. Marc is a pioneer of distressed debt investing and the CEO of Avenue Capital Group, which he co-founded with his sister in 1995. Avenue manages $13 billion today. More recently, Marc and Avenue have become active investors in sport. He owned the Milwaukee Bucks when they won the NBA championship in 2021, and has si…
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Today’s teacher is Mitch Rales, one of the most iconic business builders and philanthropists of our time. Consider that Danaher has annualized at over 21% for four decades, resulting in an 1800-times multiple on invested capital! You’ll learn from Mitch about the key inputs to his outlier success: why greatness is a journey that takes an unusual ti…
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Matt turns the mic on Eric for the quarterly recap where they reflect on a strong first quarter for 2024, the secular trends in market and investment structures, navigating the IPO market, and the next generation of investors. Please enjoy this episode of Making Markets. For the full show notes, transcript, and links to the best content to learn mo…
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This week, we bring you two titans of the podcasting world, Tim Ferriss and our very own Colossus chairman, Patrick O’Shaughnessy. We’re biased, but I think these two are two of the best interviewers in the world, and they recorded this conversation on Invest Like the Best for the 10th anniversary of Tim’s podcast. Matt and I thought you, our preci…
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My guests today are Bill Gurley and Michael Mauboussin. Bill is a General Partner at Benchmark, and Michael is the Head of Consilient Research for Counterpoint Global. While they are longtime friends with one another, I’d never heard them appear somewhere together so it was a real treat to be able to do this with the two of them. They are two of th…
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My guest this week is Brutus Clay. Brutus is the Chairman and CEO of Runnymede Farms, the oldest operating thoroughbred farm in Kentucky. He takes us through the fascinating world of breeding and racing thoroughbreds. We talk about the buy side in this industry and the similarity to Venture Capital and Private Equity. We end by talking about the ho…
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My guest today is Tim Ferriss. Tim is a writer, podcaster, and investor. He has written five best-selling books, has been an early-stage investor in Facebook, Uber, Shopify, & other household names, and is the host of one of the biggest podcasts in the world. He started The Tim Ferriss Show as an experiment in April 2014 and has deconstructed world…
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Today’s teachers are Drue Tranquill and Joe Schmidt, two of our very best former students. You'll hear about Drue’s improbable run to becoming Super Bowl champion with the Kansas City Chiefs and get to know Joe, a former walk-on at Notre Dame turned team MVP who went on to become a venture capitalist at Excel and now Andreessen Horowitz. Stepping b…
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Today we are revisiting this great episode with Jim Bianco, the founder and President of Bianco Research. Jim is well-known on Wall Street for providing macro analysis since the nineties. He takes us through his unique perspective on the economy. We start with his contrarian view on interest rates. We then cover the changes to the economy since COV…
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Our guest today is sports media veteran Mike Stricoff. Mike spent a decade producing live sports talk on national TV, first working at MLBN before moving to Fox Sports, where he helped launch Undisputed. Mike worked on that show alongside Skip Bayless, Shannon Sharpe, and others as the main line producer. In 2017, he left national TV for tech, goin…
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My guest today is 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's worth of wisdom, building Home Depot into a powerhouse and prioritizing his employees above all else. He says…
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My guest today is Yossi Levi, better known as Car Dealership Guy, who has quickly become one of the most popular voices in the auto industry. Last year, I spoke to CDG about the US Car Market and the business model of car dealerships. Today's conversation covers Yossi's personal story and media business. We start with a quick overview of his fascin…
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My guest today is Robin Dunbar. Robin is a biological anthropologist, evolutionary psychologist, and specialist in primate behavior. He is the man behind Dunbar’s number, a theory about the number of stable relationships we can maintain at once. Robin unravels the thread of research that led him to Dunbar’s number and describes how this plays into …
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Our teacher today is Chris Hansen, founder of Long Short Equity investor, Valiant Capital. Chris spun off from his early career at Blue Ridge to start Valiant and pursue his own unique investment thesis. We cover Chris's foray into investing in India, the training, temperament, and overall constitution of a great short seller, and building somethin…
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My guest this week is Bored, the pseudonymous Twitter personality who shot to prominence as Bored Elon. Bored spent over a decade in the video games industry, supporting the launch of 100+ game titles, and today, he takes us on a deep dive through the industry. We start by talking about Crypto Gaming, why it’s failed to deliver on its promise, and …
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My guest today is Sean Feeney. Sean is the co-founder of Grovehouse 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 background to write his own rulebook for the restaurant indust…
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My guest this week is Jannick Malling. At 13, Jannick was getting paid to make websites. 5 years later, he was an early employee at the high growth broker, Saxo Bank. Today, he’s a serial fintech entrepreneur and the co-founder and co-CEO of Public.com, an investing platform. In this episode, we dive into the brokerage industry. We talk about how n…
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Welcome back to Making Media. Our guest today is Emily Sundberg. Like many of our most creative guests, Emily has a wide-ranging background. For her day job, she writes her newsletter, Feed Me, which tracks valuable early trends in the consumer and brand space. If you want to know what's going to happen six months from now, read Emily's newsletter …
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My guest today is Dave Fontenot, founder of HF0. Born out of Dave’s experiences in monasteries across the world, HF0 is a twelve-week residency for repeat founders to supercharge their next venture. For 12 weeks, 10 teams of engineers relocate to HF0’s house in San Francisco. During the residency, everything is taken care of so their sole focus is …
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Our teacher today is John Crowley. It is difficult to appropriately describe John and the Crowley family's story without drawing comparisons to superheroes. Harrison Ford gave it a shot, and the result is Extraordinary Measures, a blockbuster movie he starred in, alongside Brendan Fraser and Kerry Russell. The movie is based on Gita Anand's book Th…
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My guest today is Paul Goodrich. Paul has spent his career organizing labor unions and fighting for labor rights. Today, he is the Vice President of Laborers' Union Local 151, a Massachusetts-based labor union for construction workers. In this episode, he makes a persuasive case for why we need labor unions and shows us the nuts and bolts of how th…
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My guest today is Anne-Marie Peterson. Anne-Marie is an equity portfolio manager at Capital Group, a storied investment firm managing 2.5 trillion dollars and getting ready to celebrate its centennial anniversary. Anne-Marie is a seasoned investor, approaching three decades in the industry, with nearly 20 of those years being with Capital. She has …
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My guest this week is the Anthony Pompliano, better known as Pomp. Pomp is an investor, entrepreneur and one of the biggest media personalities in the world of crypto. In today's conversation, we talk about Pomp’s early career, his evolution as a capital allocator, and how he views public and private investing today. We also talk about his early ca…
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Our guest today is Jack Davenport. Jack is the Managing Director and Co-Founder of British-based Goalhanger Podcasts. Goalhanger is the largest independent podcast network in the U.K. and likely the world outside of the U.S. Its stable of shows do 30 million downloads a month. Goalhanger got its first big breakthrough with the excellent history pod…
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My guest today is Aravind Srinivas. He is the founder and CEO of Perplexity, a startup that he describes as an “answer engine” built from scratch with AI. Aravind has set out for perplexity to become the most powerful answer engine backed by up-to-date sources. He helps me pick the technology apart, describing the behind the scenes of what it takes…
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Our teachers today are Daniel Eisen and Paul Yancich, co-founders of Arcadea Group. Arcadea is a private market, long-duration investor building a permanent home for high-quality, vertical market software companies. Today, we sit down with an example of next-generation talent in Daniel and Paul, who began Arcadea after having the rare opportunity t…
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My guest this week is Jim Bianco, the founder and President of Bianco Research. Jim is well-known on Wall Street for providing macro analysis since the nineties. Today, he takes us through his unique perspective on the economy. We start with his contrarian view on interest rates. We then cover the changes to the economy since COVID, such as remote …
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My guest today is Ali Hamed. Ali was first on Invest Like the Best six years ago. He was 26 at the time and four years into building his investing firm, CoVenture. Both then and now, Ali is an example of what’s possible when you think creatively. Six years later, CoVenture now manages two-and-a-half billion dollars, and Ali continues to find alpha …
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My guest this week is Haseeb Qureshi, managing partner at Dragonfly Capital. From making millions through poker before the age of 21, to going viral for an article on negotiation, to being hired personally by Naval Ravikant to be a crypto VC, Haseeb’s life could be a Netflix movie. We dive into that backstory and all he’s learned about the relation…
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Our guest today is Peter Kafka. If you've listened to media podcasts, you've likely listened to Peter's Recode Media. It has been a fixture in the industry for years. Peter recently announced he's going back to Business Insider, which is notable because he was the first hire way back when it was known as Silicon Valley Insider in 2007. Given Peter …
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