Invest Like the Best with Patrick O'Shaughnessy - podcast cover

Invest Like the Best with Patrick O'Shaughnessy

Colossus | Investing & Business Podcastsjoincolossus.com
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

Episodes

Kareem Zaki - Small Ideas Attract Competition - [Invest Like the Best, EP.392]

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 services, where he's led the firm's investments in companies like Ramp and Robinhood. It's a timely moment to have this discussion, with Thrive announcin...

Oct 08, 20241 hr 27 minEp. 392

Ray Ozzie - The Future of Intelligent Machines - [Invest Like the Best, EP.391]

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 the development of Azure, Microsoft's cloud computing platform. Ray's work has earned him numerous accolades, including induction into the Computer Hi...

Oct 01, 20242 hr 34 minEp. 391

Ted Seides - Investment Industry Paradigms - [Invest Like the Best, EP.390]

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 investing roles, he shares with us the wisdom he has gained from being a neutral third party with in conversations with countless industry experts. We ...

Sep 26, 20241 hr 1 minEp. 390

Lulu Meservey - Transforming Company Narrative - [Invest Like the Best, EP.389]

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 comms and a believer in creative problem-solving through effective communication and compelling storytelling. We discuss the evolution of media and its ...

Sep 24, 20241 hr 7 minEp. 389

Ric Elias - The Art of Living Well - [Invest Like the Best, EP.388]

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 employees. Ric walks us through the early struggles that have led to what is now a flourishing investing platform, but mostly this episode is a masterclass on...

Sep 17, 20241 hr 25 minEp. 388

Alex Smith, Shane Battier, & Ravi Gupta - What Makes A Glue Guy? - [Invest Like the Best, EP.387]

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 the NFL draft, 3 time-pro bowler, and 16-year NFL veteran. Ravi as a leader at KKR, and then as a critical leader turning around & building Instacart, a...

Sep 10, 20241 hr 23 minEp. 387

Bret Taylor - The Agent Era - [Invest Like the Best, EP.386]

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 platform for businesses, and he is the chairman of the board at OpenAI. We discuss the past, present, and future of AI agents: new programs that will...

Sep 03, 20241 hr 28 minEp. 386

Gavin Baker - AI, Semiconductors, and the Robotic Frontier - [Invest Like the Best, EP.385]

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 guest to discuss all things AI and investing. There is so much detail in this discussion and I’m incredibly grateful to Gavin for sharing his wisdom with ...

Aug 27, 20242 hr 31 minEp. 385

A Conversation with Charlie Munger & John Collison - [Invest Like the Best, REPLAY]

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 mentioned content, check out the episode page here. ----- This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern op...

Aug 20, 20242 hr 40 min

Vlad Tenev - Navigating Robinhood's Evolution - [Invest Like the Best, EP.384]

My guest today is Vlad Tenev. Vlad is the CEO and co-founder of Robinhood. It was such a treat to sit down with him and discuss the behind-the-scenes of a revolutionary business we all know well. He details Robinhood’s journey to zero-cost trading and what it means to build a consumer-centric financial product. Vlad believes in finding the harmonies across mathematics and art and applies this lens to everything he builds. We discuss Robinhood’s new credit card and more products on the horizon, t...

Aug 13, 20241 hr 18 minEp. 384

Sarah Guo - The Power of Conviction - [Invest Like the Best, EP.383]

My guest today is Sarah Guo. Sarah is the founder and CEO of Conviction, an early-stage venture capital firm built to serve AI companies. She started Conviction in 2022 after 9 years at Greylock because she believes AI is the most important technological advancement of our lifetime. In our conversation, Sarah discusses the challenges and rewards of leaving an established investing firm to start her own venture. She shares her unique perspective on the AI landscape and reveals her predictions for...

Aug 06, 20241 hr 13 minEp. 383

Hemant Taneja - Engineering Global Resilience - [Invest Like the Best, EP.382]

My guest today is Hemant Taneja. Hemant is the CEO and Managing Director of General Catalyst, the global venture capital firm you’ll hear us refer to as GC. GC has set out to build resiliency across critical industries worldwide. The firm leverages technology to retool sectors such as healthcare, energy, defense, and manufacturing and explores innovative capital structures to support founders and businesses. Hemant discusses how the firm is positioned to respond to the aftermath of crises, inclu...

Jul 31, 20241 hr 3 minEp. 382

Jeremy Giffon - Special Situations in Private Markets - [Invest Like the Best, Replay]

Today we are replaying one of our most popular episodes from last year with Jeremy Giffon. I spend all my time trying to find people who have some “singularity” to them. People who seem like they can do an N of 1 something. Having spent many days with Jeremy, he strikes me as one of those people. He was the first employee and general partner at private equity firm/holding company Tiny, which buys and holds internet and technology-focused businesses. Prior to that, he was on the founding team of ...

Jul 23, 20242 hr 43 min

David Senra - Passion & Pain - [Invest Like the Best, Replay]

Today, we are replaying what we call a forever episode, which are the few episodes of our show that we think will be as popular a decade from now as they are today. Every time I re-listen to this episode with David Senra, I leave wildly energized and wanting to share that feeling. So we are re-releasing it today for anyone who missed it the first time or hadn't yet discovered Invest Like the Best. David Senra has studied history’s great founders and entrepreneurs in more depth than anyone I’ve e...

Jul 16, 20241 hr 22 min

Martin Casado - Entering Uncharted AI Territory - [Invest Like the Best, EP.381]

My guest today is Martin Casado. Martin is a partner at Andreessen Horowitz and first joined me on Invest Like the Best in 2022. So much has changed since then, and it was awesome to have Martin back to discuss all of the different implications of this AI revolution. Before joining a16z, Martin pioneered software-defined networking and co-founded Nicira, which was bought by VMware for $1.3 billion in 2012. He has studied, built, and invested in digital infrastructure his whole career which has p...

Jul 09, 20241 hr 7 minEp. 381

Modest Proposal - AI Commoditization and Capital Dynamics - [Invest Like the Best, EP.380]

My guest today is Modest Proposal, joining me for our third conversation and the first in a few years. Modest is anonymous online, but one of the more thoughtful investors I know, overseeing a large pool of capital in public and private markets. He offers insight into many different corners of today’s landscape, covering AI’s frontier models versus open-source models, overcapacity issues in transportation in our post-COVID world, the potential economic impact of GLP-1 drugs, and more. Please enj...

Jul 02, 202456 minEp. 380

Robert Greene - Optimizing Your Reality - [Invest Like the Best, EP.379]

My guest today is Robert Greene, author of many books but perhaps most famous for his books "48 Laws of Power" and "Mastery." He has spent his life studying why people behave like they do and why some go on to build great things. I love his idea of finding your life's purpose, which we explore in detail. Please enjoy my conversation with Robert Greene. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episo...

Jun 25, 20241 hr 2 minEp. 379

Pat Grady - Relentless Application of Force - [Invest Like the Best, EP.378]

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 outside of his firm. We talk about investing, building an investing firm, and building enduring companies. Please enjoy this great conversation with Pat G...

Jun 18, 20242 hr 31 minEp. 378

Frank Blake - Leading By Example - [Invest Like the Best, EP.377]

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 culture of an inverted hierarchy and producing seven consecutive years of growth for the largest home improvement retailer in America. We discuss his h...

Jun 11, 20241 hr 3 minEp. 377

Adam Sandow - The Power of Print Media - [Invest Like the Best, EP.376]

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 of billionaires to transforming the design industry with overnight access to samples, when Adam starts a business he writes his own rulebook. We discu...

Jun 04, 20241 hr 5 minEp. 376

Howie Liu - Building Airtable - [Invest Like the Best, EP.375]

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, Howie has maintained a focus on an intuitive building experience, allowing anyone to build out their workflow within minutes or hours. We discuss the f...

May 28, 20241 hr 9 minEp. 375

Mark Groden - The Future of Flying - [Invest Like the Best, EP.374]

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 universal flying system. Mark is the quintessential example of somebody doing their life’s work and I have no doubt you will come to that conclusion for your...

May 21, 20241 hr 6 minEp. 374

Dev Ittycheria - The Database Evolution - [Invest Like the Best, EP.373]

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. We discuss Dev’s philosophy for constructing an exceptional enterprise sales organization, why he feels a leader must be incredibly judgemental to d...

May 14, 20241 hr 9 minEp. 373

Nico Wittenborn - Finding the Adjacent Possible - [Invest Like the Best, EP.372]

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 investing process on his own as he believes this allows him to be as close to finding the truth as possible. We discuss sharpening your intuition, eval...

May 07, 20241 hr 22 minEp. 372

Mitch Rales: The Art of Compounding - [Art of Investing, Forever Episode]

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 covers his entire history and business philosophy. Interviewing Mitch are Paul Buser and Rick Buhrman, who host the Art of Investing podcast on the Colossu...

May 02, 20242 hr 7 min

Marc Lasry - Making Bucks in Credit and Sports - [Invest Like the Best, EP.371]

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 since made investments in sports as diverse as sailing and bull-riding. In our discussion, we talk about his journey building a big investing firm, the ...

Apr 30, 20241 hr 8 minEp. 371

Bill Gurley & Michael Mauboussin - Putting Theory into Practice - [Invest Like the Best, EP.370]

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 incr...

Apr 23, 20242 hr 32 minEp. 370

Tim Ferriss - Curating Curiosities - [Invest Like the Best, EP.369]

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 abou...

Apr 16, 20241 hr 27 minEp. 369

Ken Langone - The American Dream - [Invest Like the Best, EP.368]

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 i...

Apr 09, 202449 minEp. 368

Robin Dunbar - Optimizing Human Connection (Dunbar's Number) - [Invest Like the Best, EP.367]

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 struct...

Apr 02, 20241 hr 2 minEp. 367