Invest Like the Best with Patrick O'Shaughnessy Colossus

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 MediaCore, which was acquired by Workday.
The focus of our discussion is on esoteric opportunities that exist in private markets and how misaligned incentives and coordination problems create special situations for people like Jeremy to invest in. The rest of the conversation is wide-ranging and covers everything from compensation advice to meeting your heroes. Please enjoy my discussion with Jeremy Giffon.

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 Step away from outdated, inefficient methods and into the future with our platform, proudly hosting over 100,000 transcripts – with over 25,000 transcripts added just this year alone.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.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
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.
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
(00:03:15) What defines the nature of a perfect business in his mind
(00:05:21) Key characteristics he’d look for in a perfect investment
(00:09:58) Coordination problems that excite him
(00:14:02) Raising funds and ghostship companies 
(00:16:17) Examples of a special situations transaction in private markets 
(00:18:55) Building up a sourcing mechanism
(00:22:18) The biggest mistakes he’s seen in buying and selling companies 
(00:25:42) Refining the underwriting process
(00:28:57) Thoughts about minimum rates of return and multiples on capital for the investments he makes 
(00:30:44) Being lazy enough to wait for good deals on enduring businesses 
(00:33:32) Why people do things they don’t like 
(00:35:47) Whether or not he feels like he knows what he wants in life
(00:42:58) Hiring CEOs
(00:44:54) Really good respective returns in low risk companies and why those opportunities continue to persist   
(00:47:05) Tactics for negotiating with and sourcing CEOs  
(00:50:37) Binaries - pre and post fall
(00:55:58) Being hard to kill
(00:59:15) His favorite interview question 
(01:06:07) Having an audience is incredibly underpriced 
(01:10:13) What else is significantly underpriced
(01:12:14) Things he feels are overpriced today writ large
(01:15:54) Criticisms of the cult of learning
(01:20:21) The one call that everyone needs to make 
(01:27:18) Meeting your heroes and having mentors 
(01:30:48) Notable differences between the business environments of Canada and the US
(01:33:13) Lessons learned from people he admires and models for seeing the world 
(01:35:35) Views he holds that would make people scratch their heads
(01:40:02) The kindest thing anyone has ever done for Jeremy 

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 ever met, and I’d wager more than anyone else alive. In this conversation, we cover many of the most common themes he’s discovered studying hundreds of entrepreneurs like Estée Lauder, John Rockefeller, Enzo Ferrari, and Edwin Land. Please enjoy this great conversation with David Senra.

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.
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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
[00:03:01] First question - When he first fell in love with reading
[00:07:01] What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders - Founders Podcast
[00:10:34] The first time he connected with someone as a positive role model that he was reading about 
[00:13:45] How often obsession is apparent in the founders he’s studied across hundreds of biographies 
[00:18:08] What is often behind obsession and how people listening can apply the lessons to their own lives
[00:22:45] The dynamic and relationship between inspiration and perspiration 
[00:27:11] Commonalities between the layers of leadership and support underneath founders
[00:31:52] Where else he’s seen ego rear its head in good and bad ways 
[00:38:34] How often do great founders break the law or enter gray areas of it 
[00:41:22] The role constant learning and listening plays in success
[00:45:12] Talking about how anything worth doing is worth doing to excess 
[00:52:18] Describing the soul of founders and businesses
[00:58:39] What he’s learned about all of these founders as it relates to marketing 
[01:04:38] A common story that process is often art 
[01:08:10] Who David's idols are in podcasting
[01:14:55] Major aspects of people he’s studied that haven’t been discussed yet
[01:19:55] The kindest thing anyone has ever done for David

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 primed him to go in-depth in this interview on the immense opportunities and challenges AI presents among creativity, policy-making, agentic systems, real-world data structures, and beyond. Please enjoy this conversation with Martin Casado. 

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
(00:01:48) The Future of AI and Creativity
(00:03:11) Economic Implications of AI
(00:04:33) AI's Impact on Content Creation
(00:08:21) Challenges in AI and Robotics
(00:12:16) Human Data and AI Training
(00:20:30) Investing in AI and Robotics
(00:26:00) Defensibility and Competition in AI
(00:33:22) Regulatory Considerations
(00:35:26) Internet Era Parallels and Security Concerns
(00:40:25) Open Source vs. Closed Source in Tech
(00:43:45) Market Annealing and Category Creation
(00:46:13) Data and Hardware Innovations in AI
(00:55:55) Agents and the Future of AI

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 enjoy my conversation with Modest Proposal.

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
(00:04:00) Comparison to Mid-2000s Commodity Markets
(00:07:18) The Role of AI and Power Consumption
(00:09:29) NVIDIA and the Future of AI Investment
(00:13:10) Commercialization of AI and Market Dynamics
(00:23:14) Public vs. Private Market Performance
(00:28:03) Post-COVID Capital Cycles
(00:30:32) Capital Expenditures and Post-COVID Market Distortions
(00:31:47) Amazon's Capacity Expansion and Market Inflections
(00:33:45) Challenges in Displacing Market Leaders
(00:37:50) Behavioral Barriers in GLP-1 Adherence
(00:39:58) Public vs. Private Market Allocations
(00:45:08) International Equities and Japanese Market Potential
(00:47:35) Market Structure and Trading Dynamics
(00:53:22) AI Models and Future Market Implications

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 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
(00:03:17) First Question - Exploring Reality and Human Behavior
(00:07:41) The Concept of Masks and Social Roles
(00:10:47) The Sublime and Social Conventions
(00:13:48) Writing 'The 48 Laws of Power'
(00:16:38) Defining and Understanding Power
(00:18:01) Historical Figures and Adaptation
(00:23:59) Modern Applications of Power Laws
(00:31:57) The Boldness of Deception
(00:32:54) Exploring Good and Evil
(00:35:56) The Art of Seduction and AI
(00:38:31) Defining Mastery
(00:42:44) Discovering Your Life's Task
(00:51:53) The Power of Observation
(00:59:56) The Kindest Thing Anyone Has Ever Done for Robert

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.
-----
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