464 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 • 192 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

    Pat Grady - Relentless Application of Force

    Pat Grady - Relentless Application of Force

    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 Grady.

    Listen to Founders Podcast
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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    This episode is brought to you by Tegus, where we're changing the game in investment research. Step away from outdated, inefficient methods and into the future with our platform, proudly hosting over 100,000 transcripts – with over 25,000 transcripts added just this year alone. Our platform grows eight times faster and adds twice as much monthly content as our competitors, putting us at the forefront of the industry. Plus, with 75% of private market transcripts available exclusively on Tegus, we offer insights you simply can't find elsewhere. See the difference a vast, quality-driven transcript library makes. Unlock 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
    (00:05:48) Doug Leone's Leadership and Changes
    (00:06:54) Creating Internal Pressure and Structure
    (00:10:46) Sequoia's Team Values and Family Influence
    (00:13:40) Assessing Founders and Investments
    (00:20:28) Winning Competitive Investments
    (00:24:45) Pat’s Early Career at Sequoia
    (00:29:38) Memo Writing and Investment Criteria
    (00:35:20) Evaluating Companies Through Three Business Criteria
    (00:40:15) Building Sustainable Competitive Advantage
    (00:47:48) Turning Bad Numbers into Good Investments
    (00:51:20) The AI Frontier: Market and People
    (01:01:13) Harvey: The AI Legal Assistant
    (01:05:33) Sequoia's Platform Strategy
    (01:17:16) The Importance of Teamwork and Performance
    (01:26:07) Legendary Potential: Relentless Application of Force
    (01:28:37) The Kindest Thing Anyone Has Ever Done for Pat

    • 1 hr 30 min
    Frank Blake - Leading By Example

    Frank Blake - Leading By Example

    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 hyper focus on solving their customer’s problems before their own, investing time into the employee experience, and his intentionality with how he is perceived as a leader. Please enjoy this discussion with Frank Blake.

    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, where we're changing the game in investment research. Step away from outdated, inefficient methods and into the future with our platform, proudly hosting over 100,000 transcripts – with over 25,000 transcripts added just this year alone. Our platform grows eight times faster and adds twice as much monthly content as our competitors, putting us at the forefront of the industry. Plus, with 75% of private market transcripts available exclusively on Tegus, we offer insights you simply can't find elsewhere. See the difference a vast, quality-driven transcript library makes. Unlock 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
    (00:04:37) The Inverted Pyramid Leadership Model
    (00:08:38) Communication and Listening in Leadership
    (00:15:19) Lessons from Legacies of Great Home Depot Leaders
    (00:27:02) Frank’s Personal Leadership Journey
    (00:33:32) Reagan's Leadership Style and Influence
    (00:37:26) Key Responsibilities of a CEO
    (00:40:27) Delta's Leadership During COVID-19
    (00:46:45) Financial Strategies in Asset-Intensive Industries
    (00:47:27) Home Depot's Strategic Shift
    (00:53:33) Competitive Dynamics with Lowe's
    (00:55:36) Building an Effective Board
    (00:58:16) The Impact of Home Depot on Employees' Lives
    (01:01:52) The Kindest Thing Anyone Has Ever Done for Frank

    • 1 hr 2 min
    Adam Sandow - The Power of Print Media

    Adam Sandow - The Power of Print Media

    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 discuss the founding stories of his most interesting companies, his obsession with targeting pain points, and his philosophies for when to go all in and betting on himself. Please enjoy this great discussion with Adam Sandow.

    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, where we're changing the game in investment research. Step away from outdated, inefficient methods and into the future with our platform, proudly hosting over 100,000 transcripts – with over 25,000 transcripts added just this year alone. Our platform grows eight times faster and adds twice as much monthly content as our competitors, putting us at the forefront of the industry. Plus, with 75% of private market transcripts available exclusively on Tegus, we offer insights you simply can't find elsewhere. See the difference a vast, quality-driven transcript library makes. Unlock 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 
    (00:04:12) Building a Media Empire
    (00:06:01) The Birth of the Beauty Subscription Model
    (00:09:56) Revolutionizing Magazine Circulation
    (00:14:46) The Contrarian Approach to Media
    (00:16:08) The Origin of MediaJet
    (00:18:35) The Future of Print and Digital Media
    (00:27:25) The Genesis of Material Bank
    (00:35:23) Building a Compelling Model for Manufacturers
    (00:37:26) Innovative Logistics and Partnership with FedEx
    (00:40:32) The Importance of High-Quality Content
    (00:43:49) Building and Buying Media Properties
    (00:46:01) Creating Unique Value Propositions
    (00:54:22) The Role of Print in the Digital Age
    (00:58:41) Nurturing an Ecosystem of Businesses
    (01:03:37) The Kindest Thing Anyone Has Ever Done for Adam

    • 1 hr 4 min
    Howie Liu - Building Airtable

    Howie Liu - Building Airtable

    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 future of the platform in the era of AI, his perspective on horizontal versus vertical software solutions, and his crucial moments as a leader in building a critical component to the advancement of productivity. Please enjoy this discussion with Howie Liu. 

    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, where we're changing the game in investment research. Step away from outdated, inefficient methods and into the future with our platform, proudly hosting over 100,000 transcripts – with over 25,000 transcripts added just this year alone. Our platform grows eight times faster and adds twice as much monthly content as our competitors, putting us at the forefront of the industry. Plus, with 75% of private market transcripts available exclusively on Tegus, we offer insights you simply can't find elsewhere. See the difference a vast, quality-driven transcript library makes. Unlock 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
    (00:06:49) Exploring Horizontal vs. Vertical Software in the AI Era
    (00:11:00) The Future of Customized Applications
    (00:15:28) Perspectives on AI's Future and Enterprise Adoption
    (00:18:13) The Evolution of LLMs and Their Impact on Software Development
    (00:23:33) Harnessing AI for Business Transformation and Innovation
    (00:27:28) Reflecting on Airtable's Founding and Evolution
    (00:33:23) Airtable's Approach to Customer Engagement and Innovation
    (00:39:59) The Impact of AI on Platform Versatility and Market Penetration
    (00:46:00) Achieving Product-Market Fit and Initial Monetization
    (00:50:23) Scaling Up and Securing the First Unicorn Round
    (00:51:52) Rapid Growth and Organizational Scaling Challenges
    (00:55:00) Reflecting on Tough Decisions in the Business
    (01:02:55) The Role of Capital Allocation in Expanding Airtable
    (01:06:55) The Kindest Thing Anyone Has Ever Done For Howie

    • 1 hr 9 min
    Mark Groden - The Future of Flying

    Mark Groden - The Future of Flying

    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 yourself after listening to his story. He’s determined, through Skyryse, to drive aviation deaths down to zero, and we discuss all of the details, big and small, that have laid the groundwork for realizing this dream. Please enjoy this conversation with Mark Groden.

    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, where we're changing the game in investment research. Step away from outdated, inefficient methods and into the future with our platform, proudly hosting over 100,000 transcripts – with over 25,000 transcripts added just this year alone. Our platform grows eight times faster and adds twice as much monthly content as our competitors, putting us at the forefront of the industry. Plus, with 75% of private market transcripts available exclusively on Tegus, we offer insights you simply can't find elsewhere. See the difference a vast, quality-driven transcript library makes. Unlock 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
    (00:03:53) From Childhood Fascination to Professional Pursuit
    (00:05:47) Understanding General Aviation vs. Commercial Aviation
    (00:07:05) The Safety Gap in General Aviation
    (00:10:27) The Evolution of Aircraft Technology and Safety
    (00:16:20) The Mechanic of Flying a Helicopter
    (00:21:40) Justifying the Existing Dangers of Helicopter Flight
    (00:24:45) The Future of Flying Cars and Urban Air Mobility
    (00:27:23) Economies of Scale in Aviation and the Path Forward
    (00:35:26) The Evolution of Autonomous Flight
    (00:37:58) The Promise of SkyOS: Revolutionizing Flight with AI
    (00:42:04) Piloting the Future: How Automation Empowers Pilots
    (00:45:43) Exploring the Business of Flight and Future Innovations
    (00:51:08) What Is Holding Back The Future of Flying
    (00:57:08) Mission-Driven Innovation: A Personal Journey
    (01:00:46) The Kindest Thing Anyone Has Ever Done For Mark

    • 1 hr 6 min
    Dev Ittycheria - The Database Evolution

    Dev Ittycheria - The Database Evolution

    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 drive excellence, and how he plans to guide MongoDB through another technological transition. Please enjoy this conversation with Dev Ittycheria.

    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
    (00:03:39) A CEO's Perspective Of The AI Revolution
    (00:05:50) The Evolution of Apps From Trivial to Transformative
    (00:08:12) MongoDB's Journey From Startup to AI Era
    (00:10:03) Building a Modern Database Company: MongoDB's Story
    (00:13:19) The Long-Term Vision for MongoDB 
    (00:15:51) Dev’s Formative Experiences as a Tech CEO
    (00:19:18) The Art of Enterprise Sales
    (00:25:28) The Development of Dev as a Leader
    (00:29:01) Getting the Most Out of Your Talent
    (00:33:17) Managing a Multi-Product, Multi-Channel Enterprise
    (00:37:29) Dev’s Recruiting Philosophy
    (00:43:12) The Role of Leadership and Mentorship in Career Growth
    (00:46:08) Dev’s Deepest Worry With MongoDB
    (00:49:35) Personal Investment Philosophy and Identifying Potential
    (00:53:52) The Art of Leadership: Accountability and Development
    (00:57:50) Learning from Legends: Andy Grove's Management Insights
    (01:02:54) The Power in MongoDB’s Business
    (01:06:13) Up Next for Dev and MongoDB
    (01:08:34) The Kindest Thing Anyone Has Ever Done For Dev

    • 1 hr 9 min

Customer Reviews

4.8 out of 5
192 Ratings

192 Ratings

Babsie53 ,

Thank you

The quality of the questions are top notch. Learnings on learnings.

Duncinlym ,

What a gift thank you

Only recently discovered this podcast. I find it quite mind blowing that this level of content, network access and incredible intellect is available here for free. Just wish I had more spare hours to listen to all the back episodes.

StumpyWelshGit ,

Great show

I was an investment banker and PE professional for 20 years. Listened to my first 3 podcasts today and could have been in a meeting with old colleagues: no talking-down or ultra-basic explanations - just market pros talking to another expert with us listening in. Fantastic!

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