455 episodes

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

Invest Like the Best with Patrick O'Shaughnessy Colossus

    • Business
    • 4.8 • 135 Ratings

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

    Bill Gurley & Michael Mauboussin - Putting Theory into Practice

    Bill Gurley & Michael Mauboussin - Putting Theory into Practice

    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 the leading minds in their fields, and we combined their decades of expertise into one wide-ranging conversation. We discuss the different kinds of increasing returns to scale, the issue of regulatory capture, AI, and hardware. Please enjoy this great conversation with Bill Gurley and Michael Mauboussin.

    Listen to Founders Podcast
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick.
    -----
    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
    (00:03:38) Dissecting the Dynamics of AI, LLMs, and Market Disruption
    (00:05:06) The World of AI Investments and Market Trends
    (00:08:13) Integration of New Technologies in Business
    (00:15:27) The Power of Increasing Returns and Strategic Investments
    (00:22:26) Unpacking the Role of Intangibles in Scaling and Innovation
    (00:28:54) Transformative Potential of Open Source and Idea Recombination
    (00:34:42) The Complex Landscape of Regulation and Innovation
    (00:43:17) Today’s Venture Capital Ecosystem
    (00:47:08) Impact of Fewer IPOs and Private Market Dynamics
    (00:50:38) Capital Allocation in Zero Interest Rate Environments
    (00:54:44) The Evolution of Venture Capital and High-Stakes Investment Games
    (00:57:21) Exploring New Frontiers: AI, Energy, and Physical World Innovations
    (01:01:14) The Power of Learning by Doing
    (01:17:49) Working with Genius
    (01:26:47) The Value of Teaching, Writing, and Sharing Knowledge

    • 1 hr 32 min
    Tim Ferriss - Curating Curiosities

    Tim Ferriss - Curating Curiosities

    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-class performers ever since. Last year, his show crossed 1 billion downloads. Together, we deconstruct his podcast and approach to life. We talk about the art of interviewing, the business behind his podcast, and what motivates Tim to keep teaching through his writing and podcast. Please enjoy this great conversation with Tim Ferriss.

    Check Out Invest America 2024
    Listen to Founders Podcast
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick.
    -----
    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
    (00:03:32) The Evolution of Podcasting with Tim Ferriss
    (00:09:56) Crafting Meaningful Conversations
    (00:13:26) What Makes Tim Feel The Most Alive 
    (00:24:06) Who Tim Considers To Be His Mentors
    (00:29:06) The Ingredients Of A World Class Performance
    (00:31:06) The Business Side of Podcasting
    (00:43:15) Identifying Emerging Trends
    (00:50:12) Lessons From Building a Small, Efficient Team
    (00:52:32) The Power of Constraints in Personal and Professional Growth
    (00:53:10) Innovating Against the Grain (Anti-Video Experiment)
    (00:54:54) Navigating Fame, Money, and Power
    (01:02:00) The Impact of Sharing Difficult Stories
    (01:06:18) Meta-Learning: A Framework for Fast, Effective Learning
    (01:12:32) Reflecting on a Decade of Podcasting & What’s In Store
    (01:24:41) The Kindest Thing Anyone Has Ever Done For Tim

    • 1 hr 26 min
    Ken Langone - The American Dream

    Ken Langone - The American Dream

    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 he still “bleeds orange” to this day. You’ll hear as he recounts his business endeavors, his strict belief in keeping your word, and his true pride in his country, which he knows to be the land of opportunity. We discuss his work with Ross Perot, the idea of an upside-down hierarchy, and the power of loyalty. For anyone who may find it easier to follow along, we have a transcript of the episode on joincolossus.com. Please enjoy this conversation with Ken Langone.  

    Listen to Founders Podcast
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Tegus, the go-to destination for bold investing. The investment research platform trusted by 95% of the top 20 global private equity firms just got even better. Building on their solid reputation for expert insights, Tegus has expanded to become the first true all-in-one research platform. The new Tegus makes diligence faster, easier, and more convenient than ever before. Your Tegus license gives you access to over 70,000 expert transcripts, more than 4,000 fully drivable financial models, and exclusive datasets like company management checks, industry KPIs, hard-to-find non-GAAP data, and more. Tegus is the fastest way to learn about a public or private company and the most cost-effective way to conduct investment research — now all under one roof. Learn more and get your free trial at tegus.com/patrick.
    -----
    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
    (00:004:00) The Unforgettable Pitch to Ross Perot
    (00:08:37) Winning Over Perot with Honesty and Insight
    (00:16:08) The Art of Negotiation and Trust
    (00:19:31) Loyalty, Integrity, and the Power of Keeping Your Word
    (00:23:51) Home Depot's Culture of Service and Empowerment
    (00:29:16) Frank's Authentic Leadership and Its Impact
    (00:31:00) Transforming NYU Medical Center
    (00:33:45) Ken’s Investment Philosophy: Long Hold Only
    (00:39:56) The Power of Resilience in Business
    (00:45:37) The Kindest Thing Anyone Has Ever Done For Ken

    • 48 min
    Robin Dunbar - Optimizing Human Connection (Dunbar's Number)

    Robin Dunbar - Optimizing Human Connection (Dunbar's Number)

    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 every single person’s layers of human connection. It was fascinating to hear how his findings on social circles have implications for optimally structuring businesses and organizations, as well as the idea of homophily, all of which Robin thoughtfully explains. It was a treat to get to explore these topics with Robin Dunbar himself so please enjoy this great conversation.  

    Listen to Founders Podcast
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Tegus, the only investment research platform built for fundamental investors. Whether you’re trying to get up to speed on a new market or keep tabs on a portfolio company, Tegus is the end-to-end investment research platform you need. With Tegus, you can quickly understand a company's business model, drivers, benchmarks, and management quality. To monitor an entire market, download our pre-built financial models — or update your own with the latest data using Tegus’ new Excel Add-In. Tegus gives you all of this and more, all bundled into a single software license. Find out why 95% of the top 20 global private equity firms are Tegus customers. Learn more and get your free trial at tegus.com/patrick.
    -----
    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
    (00:04:39) The Journey to Discovering Dunbar's Number
    (00:07:28) Exploring the Layers of Human Connection
    (00:12:27) The Significance of the 1.5 Layer in Social Circles
    (00:16:55) Surprising Insights from Social Network Studies
    (00:20:40) Applying Dunbar's Number to Organizational Structures
    (00:27:51) The Science of Social Bonding in Primates and Humans
    (00:33:23) Unlocking the Endorphin System Without Physical Touch
    (00:34:10) The Power of Laughter, Singing, and Storytelling in Group Bonding
    (00:36:00) The Limitations of Digital Interactions for Building Relationships
    (00:39:51) Reviving Social Clubs and Activities for Workplace Bonding
    (00:44:40) The Importance of Homophily in Friendships and Social Networks
    (00:50:40) Challenges and Solutions for Overcoming Loneliness and Building Trust
    (00:53:45) The Impact of Technology, Religion, and Mental Health on Social Connections
    (00:61:47) Reflecting on Time as a Fundamental Aspect of Social Dynamics

    • 1 hr 2 min
    Sean Feeney - Reinventing the Restaurant Business

    Sean Feeney - Reinventing the Restaurant Business

    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 industry, crafting several establishments that now boast several thousand people on the waitlist any given night. His story is as entertaining as it is inspiring. As we go step by step through his business endeavors, he points out all of the times he was told “it’s just always been done this way” and how that revealed to him where he could innovate. Sean’s restaurants are the perfect example of building a business into the fabric of a community, collaborating with other brands in authentic ways, and staying true to yourself along the way. Please enjoy this awesome conversation with Sean Feeney. 

    Listen to Founders Podcast
    Join Positive Sum as a Research Analyst
    
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick.
    -----
    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
    (00:03:58) First Question - A Chance Encounter with a Michelin-Starred Chef
    (00:08:52) The Birth of a Culinary Partnership
    (00:12:49) Embracing the Genius Within
    (00:16:41) Innovative Approaches to the Restaurant Business
    (00:24:53) Creating Demand: The Art of Exclusivity
    (00:28:49) Learning from the Best: Insights from Kith's Success
    (00:34:21) Defining Exceptional Hospitality
    (00:44:20) The Power of Customer Relationships in Hospitality
    (00:52:31) Unlocking Team Potential 
    (00:53:33) The Philosophy of the Perfect Turn
    (00:54:05) Balancing Art, Commerce, and Satisfaction
    (00:56:13) The Impact of Authentic Experiences and Brands
    (01:03:24) The Evolution of a Hospitality Brand
    (01:06:38) Community Engagement and the Power of Simplicity
    (01:24:40) Creative Responses and Business Lessons Learned
    (01:36:05) Lessons From Working In The Restaurant Industry 
    (01:43:01) The Kindest Thing Anyone Has Ever Done For Sean

    • 1 hr 48 min
    Dave Fontenot - The Monastery of Code

    Dave Fontenot - The Monastery of Code

    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 coding and building. It’s one of the most interesting incubators I have come across and we discuss the model and its monastic origins in detail. Please enjoy this conversation with Dave Fontenot.

    Become a Research Analyst at Positive Sum
    Listen to Founders Podcast
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick.
    -----
    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
    (00:04:05) First Question - Dave’s Journey to Meditation and Monastic Life
    (00:07:25) From Monastery to Coding: Finding Flow in Programming
    (00:08:32) Creating Spaces for Uninterrupted Creativity: The Birth of HF0
    (00:20:24) A Day in the Life at HF0
    (00:25:15) Why 12 Weeks? The Philosophy Behind the Duration
    (00:27:14) Selecting the Brilliant Minds for HF0
    (00:31:43) The Thin Line Between Visionary and Crazy
    (00:34:39) Creating Space to Meditate 
    (00:37:24) The Economic Model Behind HF0
    (00:41:36) Building Successful Residencies
    (00:44:48) Expanding the Residency Model to Universities
    (00:52:52) Understanding Engineers and Hackers
    (01:02:01) The Kindest Thing Anyone’s Ever Done For Dave

    • 1 hr 3 min

Customer Reviews

4.8 out of 5
135 Ratings

135 Ratings

jacksres ,

Insightful and evergreen

Patrick is a philosopher and a futurist who also happens to be an investor. You don’t need to know anything about investing to get a lot out of this podcast; if you’re interested in how technology shapes culture, and what’s next for the world, look no further!

Kishereinoz ,

So so good

Absolutely love this podcast. Fantastic guests - only unimpressed by one or two guests so far and I’ve listened to all but a couple of episodes at this point. o'shaughnessy is hands down the best host in the game. Asks thoughtful questions and has no ego thus avoiding the awful unnecessary interruptions of the “me too” anecdote genre. I listen a lot when driving and have to constantly pull over to write notes down. Highly recommend

jaffass ,

Thought provoking and engaging

Started off with the Gavin Baker interview, now I’m hooked.

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