Invest Like the Best with Patrick O'Shaughnessy

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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

2D AGO

Gustav Söderström - How Spotify Thinks

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 industry. We discuss their integration of AI, their unique "bets board" process for allocating resources, and how they've evolved from a music service into a multimedia platform with over 650 million users. Please enjoy my conversation with Gustav Söderström. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ ----- This episode is brought to you by⁠ Ramp⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠ Ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠ AlphaSense⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠ Alpha-Sense.com/Invest⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠ Ridgeline⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠ ridgelineapps.com⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:27) Spotify's Journey Through Technological Shifts (00:06:28) The Impact of Generative AI on Consumer Products (00:09:36) AI in Coding and Productivity (00:11:11) Consumer Engagement and AI Playlisting (00:14:43) Strategic Frameworks and Decision-Making at Spotify (00:19:39) The Bets Process: Structured Innovation (00:31:11) The Future of AI and Business Models (00:44:31) The Future of AI and Inference Costs (00:46:21) The Concept of Computronium and Infinite Computing (00:47:02) David Deutsch and the Beginning of Infinity (00:48:55) The Power of Explanations and Human Understanding (00:54:03) Spotify's Free Tier and Consumer Needs (00:56:45) Spotify's Relationship with the Music Industry (01:03:03) The Rise of Podcasting and Audiobooks (01:15:45) Personal Interests and Continuous Learning (01:20:32) The Kindest Thing Anyone Has Ever Done For Gustav

1h 24m
MAY 13

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

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 developments in the search-fund ecosystem, including the bifurcation between funded searchers targeting larger companies and self-funded entrepreneurs finding success with smaller businesses. Rick and Royce share their accumulated wisdom on what makes a company worth buying, why the "magic is in the multiples," and how their students consistently achieve impressive returns through patient, value-oriented business acquisition. Please enjoy my conversation with Rick Ruback and Royce Yudkoff. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ ----- This episode is brought to you by⁠ Ramp⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠ Ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠ AlphaSense⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠ Alpha-Sense.com/Invest⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠ Ridgeline⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠ ridgelineapps.com⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:23) Changes in the Small Firm Acquisition Space (00:06:52) The Impact of SBA Loans on Acquisition Entrepreneurship (00:08:55) The Evolution of Entrepreneurship Through Acquisition (00:10:09) Risk and Return in the Search Fund Model (00:13:38) The Role of Investors in Funded and Unfunded Searches (00:19:33) Criteria for a Good Acquisition Target (00:28:36) The Growing Popularity of Self-Funded Searches (00:43:21) Challenges and Red Flags in Small Firm Acquisitions (00:49:47) Exploring Margin Expansion and Growth (00:51:02) The Impact of Practical Teaching in Business Education (00:52:12) Keys to a Successful Business Class (00:53:30) The Role of Theory in Practical Business Education (00:55:29) Challenges and Rewards of Teaching Business (00:57:46) Capital Allocation in Small Businesses (01:00:50) Advice for Aspiring Business Searchers (01:03:45) Value Creation and Business Lifecycle (01:08:20) Deciding to Leave Private Equity (01:11:20) The Future of Higher Education in Business (01:16:06) Ongoing Relationships with Former Students (01:18:45) Favorite Business Cases to Teach (01:24:46) Encouraging More People to Pursue Business Ownership

1h 28m
MAY 6

David Senra - The Focused Few

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 vacuum cleaners—while rejecting conventional growth timelines and investor pressure. David challenges us all to find the one thing we’d pursue even without recognition or reward, or what I like to call your life’s work. We discuss the concept of “anti-business,” raising capital as a founder, and decades-long commitment. Please enjoy this discussion with David Senra. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:43) The Essence of Focus in Entrepreneurship (00:09:20) The Value of Long-Term Commitment (00:17:41) The Importance of Simplicity and Mastery (00:37:11) The Miracle of Entrepreneurship (00:44:56) James Dyson's Journey to Success (00:47:03) The Importance of Passion in Business (00:49:12) Critique of Modern Consumerism (00:52:18) The Value of Craftsmanship (00:56:36) The Drive for Excellence (01:04:06) The Importance of Hiring Top Talent (01:09:54) Creative Financing Strategies (01:19:35) Defining a Founder

1h 21m
APR 29

Cliff Sosin - Investing in Carvana

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 business, which had a market cap over $60 billion in 2021, then fell 99%, survived, and now has a market cap approaching $50 billion again. While I hosted Carvana's CEO, Ernie Garcia, last year to get the inside perspective on managing through such turbulence, today we hear the investor's side of this extraordinary story. It is a singular episode and there are so many lessons in this rare opportunity to hear a major investor describe his decision-making process at every stage of the journey. Please enjoy my great conversation with Cliff Sosin. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:32) Early Career and Discovering Investing (00:06:49) Starting the Firm and Initial Challenges (00:08:41) Investment Philosophy and Market Realities (00:11:07) Building the Firm and Investor Relations (00:12:23) Defining a Good Business (00:17:31) Contained vs. Uncontained Businesses (00:20:30) Mental Models and Market Insights (00:35:13) The Role of ESG in Investing (00:39:26) The Carvana Investment Story (00:46:43) Carvana's Real Estate and Logistics Network (00:49:12) Reconditioning and Selling Cars (00:50:16) Carvana's Financing and Customer Service (00:51:43) Economies of Scale and Trust (00:54:40) Challenges and Management Insights (01:04:07) Operational Issues and Market Challenges (01:23:56) Questioning Carvana's Sales Strategy (01:24:17) The Role of Word of Mouth in Carvana's Growth (01:25:28) Identifying Early Adopters (01:26:00) The Impact of Market Conditions on Carvana (01:27:10) Carvana's Operational Challenges (01:28:10) Cutting Costs and Organizational Efficiency (01:32:19) The Apollo Deal and Debt Restructuring (01:39:21) The Psychological Toll of Investment (01:50:16) Future Investment Strategies and AI (01:54:48)The US Market and Investment Opportunities (01:59:51) The Kindest Thing Anyone Has Ever Done For Cliff

2 hr
APR 25

Cyan Banister - Investing for a Higher Purpose - [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. 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 investors of this era, having invested early in SpaceX, Uber, Postmates, and Deepmind to name a few winners. She became the first female investing partner at Peter Thiel’s Founders Fund and now invests at Long Journey Ventures. Our conversation is as much about investing as it is about the essence of life and how connecting with that will help us in our professional pursuits. It is also full of awesome stories about people and companies like SpaceX and Bill Murray. Please enjoy this great conversation with Cyan Banister. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: [00:00:00] Welcome to Invest Like the Best [00:04:06] Contrarian Thinking in Investing [00:05:30] Joining Founders Fund and Learning from Peter Thiel [00:11:15] Investing in Companies that Change Lives [00:14:00] The Importance of Overcoming Adversity for Founders [00:16:02] Personal Journey and Choosing Hope [00:20:56] Embracing Curiosity and Wonder in the Face of Adversity [00:21:20] Reconnecting with Our Inner Child [00:24:46] The Interruption and Resumption of the Conversation [00:27:20] The Power of Intuition in Business Decisions [00:32:28] The Story Behind the Investment in Uber [00:38:46] Conclusion: Following the White Rabbit of Curiosity [00:39:08] Investing in Uber: The Beginning [00:41:50] The Impact of Success: Personal Wealth and Privacy [00:50:22] The Intersection of Spirituality and Investing [00:59:34] The Bill Murray Experience: A Lesson in Presence [01:09:54] The Violin Kid: A Tale of Curiosity and Generosity [01:12:43] The Evolution of Investing: A Personal Journey [01:16:34] The Philosophy of Giving: The Universe's Return [01:17:36] The Spirit of a Venture Firm: Founders Fund [01:23:09] The Power of Integral Family Systems [01:28:41] The Trillion Dollar Question: Disrupting Hollywood [01:36:05] The Future of Artistry: AI and Creativity [01:41:39] The Power of Kindness

1h 27m
APR 22

Matt Huang - Investing At The Frontier

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 crypto, how his early investment in ByteDance (now worth 10,000x his initial capital) shaped his approach to identifying exceptional founders, and why he believes so deeply in crypto’s long-term potential. His firm, Paradigm, not only invests in many of the leading companies in the industry, it also builds open-source tools used by most of crypto. Matt has a rare blend of IQ and EQ that allows him to understand technical complexity, bring together unique talents, and ride out crypto’s notorious volatility. Whether you're crypto-curious or crypto-skeptical, I think you'll find his perspective valuable. Please enjoy my great conversation with Matt Huang. Matt Huang's Profile in Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:15) Matt Huang's College Years and Early Career (00:12:27) The Failed Startup and Lessons Learned (00:16:51) Matt's Pivotal Trip to China and ByteDance Investment (00:25:58) Sequoia's Culture of High Standards (00:32:51) Discovering Bitcoin and Crypto (00:39:33) Founding Paradigm (00:45:40) Building a Unique Investment Team (00:48:03) Challenges and Volatility in Crypto (00:53:10) The Relationship Between Legibility and Investing (00:58:40) Crypto as a New Financial System (01:05:19) The Importance of Stablecoins (01:09:54) AI and Crypto: The Next Frontier (01:16:19) Personal Motivations and Important Crypto Use Cases (01:29:23) The State of Regulation in Crypto (01:32:27) The Kindest Thing Anyone Has Ever Done for Matt

1h 32m
APR 15

Neil Mehta - Finding Future S&P 500 Companies

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, Carvana, Stripe, Discord, Rippling, and Toast—generating over $13 billion in gross profits with a 33% net IRR. Henry Kravis, one of Neil's early investors, describes him as "extremely disciplined" with "exceptional timing" who has "gone against the tide many times." Greenoaks operates with remarkable concentration: just 55 core companies across nearly $15 billion in assets, managed by only nine investment professionals. Their approach reflects their singular pursuit: finding companies that will become a meaningful part of the S&P 500. In our wide-ranging conversation, Neil shares this mission along with his framework for identifying exceptional founders, his concept of "jaw-dropping customer experiences," and how his grandfather's gun shop in India shaped his appreciation for builders of all kinds. Please enjoy my excellent conversation with Neil Mehta. Neil Mehta's Profile in Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:32) Connecting Craftsmanship to Career (00:07:45) The Concept of Jaw Dropping Customer Experience (JDCE) (00:09:48) Building a Successful Business: The Coupang Case Study (00:17:26) The Importance of Founders & Business Models (00:30:05) Greenoaks' Unique Approach to Venture Capital (00:37:54) A Memorable Encounter with Henry Kravis (00:40:52) Early Career and Lessons from Hong Kong (00:44:53) The Partnership with Benny (00:50:28) Navigating the Competitive Landscape (00:59:14) High Conviction Investments: TripActions, Rippling, and Carvana (01:07:00) Investment Strategy and Company Evaluation (01:13:23) Adventures in Emerging Markets (01:17:09) Challenges and Lessons Learned (01:26:16) Personal Values and Community Impact (01:32:16) The Kindest Thing Anyone Has Ever Done For Neil

1h 34m
APR 8

Michael Ovitz - Turning Potential into Prominence

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 Palantir and venture capitalists like Marc Andreessen. Michael is a force whose expertise extends beyond just people, as he has also become a master in creating institutional momentum, which you’ll hear in his involvement with the MoMA, Gulfstream, and more. We discuss his "pilot's checklist" for evaluating talent, the importance of time as his most valuable resource, and why he believes maintaining excellence is critical in any field. Please enjoy my conversation with Michael Ovitz. Subscribe to Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest-growing FinTech company in history, and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. I think this platform will become the standard for investment managers, and if you run an investing firm, I highly recommend you find time to speak with them. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:56) Spotting Talent and Building Institutions (00:08:01) The MoMA Story: Transforming an Art Institution (00:19:35) The Importance of Relationships and Time (00:24:32) Building Successful Boards and Teams (00:34:02) Insights on Leadership and Momentum (00:44:49) Building Blackstone and CAA (00:56:32) The Power of Momentum (00:57:25) Overcoming Fear of Failure (01:01:52) Strategic Partnerships and Global Influence (01:17:32) The Importance of Excellence (01:18:22) Mentorship and Legacy (01:34:00) The Future of Media and Technology (01:41:36) Pursuit of Happiness and Lifelong Learning

1h 42m

See All (517)

4.7

out of 5

2,207 Ratings

Loved the Kushner interview

Jan 21

ABSWeHa

Oh boy his parents should be so proud! Definitely a mensch.
There is no better.

09/19/2024

rabbiZ2019

Patrick has truly mastered the art of learning in public. He brings the most articulate guess, and trusts his audiences knowledge and intellectual level to be able to listen to the answers as they are presented without any editorializing. I feel like I have gained more from this podcast than years in business school.
Interviewing racists?

12/24/2024

J1980J

Interviewing racist Jared Kushner? Unsubscribe. “ Jared Kushner has praised the “very valuable” potential of Gaza’s “waterfront property” and suggested Israel should remove civilians while it “cleans up” the strip.”
5 star for Vlad

08/15/2024

Santa Famous

Ty