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Colossus | Investing & Business Podcasts

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

My guest today is Micky Malka. Micky is the founder of Ribbit Capital, a global venture capital firm that focuses exclusively on financial technology investments. He is a renowned investor for his adaptability and visionary approach and a believer in killing the thing that got you to where you are in pursuit of what’s next. We discuss his perspective on fintech’s evolution and why his firm boldly declares that “fintech is dead.” We dive into his theory of the "grid," which examines how knowledge, wealth, and power are being transformed by technological changes, particularly through the rise of AI, cryptocurrency, and network states. And we also explore Micky’s deep interest in digital art and NFTs, which he sees as early indicators of broader cultural and technological shifts. You’ll soon hear how he is truly taking a generative approach on all fronts. Please enjoy this in-depth conversation with Micky Malka. 

My guests today 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 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. AlphaSense provides access to over 300 million premium documents, including company filings, earnings reports, press releases, and more from public and private companies. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegas help you make smarter decisions faster.
—
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. It’s also notable that many best-in-class businesses use Ramp—companies like Airbnb, Anduril, and Shopify, as well as investors like Sequoia Capital and Vista Equity. They use Ramp to manage their spending, automate tedious financial processes, and reinvest saved dollars and hours into growth. At Colossus and Positive Sum, we use Ramp for exactly the same reason. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus.
-----
Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
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
(00:06:37) The Rebel Spirit of Ribbit
(00:07:36) Ribbit's Unique Structure and Philosophy
(00:08:07) The First Fund and Institutional Partners
(00:09:03) Founding Principles and No Labels Approach
(00:13:44) Early Investments and the Crypto Angle
(00:16:42) The FinTech Evolution and Market Dynamics
(00:22:30) Navigating Challenges: The Robinhood Story
(00:28:57) The Global Digital Grid Concept
(00:36:09) The Future of Digital Identity and Tokenization
(00:41:00) The Role of Stablecoins in the Modern Economy
(00:50:16) The Challenge of Adaptability
(00:53:05) The Role of Heart in Business
(00:55:19) The Walmart Partnership Story
(01:00:07) Lessons from NuBank
(01:02:49) Building a Strong Team
(01:09:28) The Importance of Brand
(01:11:52) Art and Its Future
(01:17:20) The Impact of Better Money
(01:19:27) Reflections and Future Plans
(01:28:03) Handling Crises and Embracing Movement
(01:31:40) The Kindest Thing Anyone Has Done For Micky

Micky Malka - Building Ribbit - [Invest Like the Best, EP.401]

My guest today is Scott Wu. Scott is the co-founder and CEO of Cognition, which is an applied AI lab that has created the first AI software engineer, which they call Devin. In just a year since founding Cognition, Devin functions at the level of a junior software engineer, capable of handling complete engineering workflows from bug fixing to submitting pull requests. He is a former competitive programming champion and describes the field as simply “the art of telling the computer what you want it to do." Scott predicts AI will surpass the world's best competitive programmer within 1-2 years and sees this technology not as replacing programmers, but as democratizing software creation. We discuss the bottleneck in software development, the future of AI in various industries, and the challenges of leveling up Devin. Towards the end, you’ll also hear Scott do an insane card trick on me. You can find the video on our X and YouTube to grasp the madness fully. Please enjoy my conversation with Scott Wu.

Watch Scott play the card game.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.
-----
﻿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. AlphaSense provides access to over 300 million premium documents, including company filings, earnings reports, press releases, and more from public and private companies. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegas 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. 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.
-----
Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
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
(00:07:00) Discussion of Devin's current capabilities as a junior engineer 
(00:09:00) Early use cases and customer adoption 
(00:11:00) Comparison between IDE assistants and Devin's autonomous approach
(00:14:00) History of computer programming and its evolution 
(00:17:00) Scott's background in competitive programming 
(00:20:00) Future predictions for AI in software engineering 
(00:26:00) Explanation of AI agents and their significance 
(00:29:00) Technical details of how Devin is built 
(00:40:00) Impact on software engineering jobs and industry 
(00:47:00) Discussion of business model and pricing 
(00:52:00) Thoughts on AGI and its practical implications 
(00:59:00) Commentary on the competitive landscape 
(01:24:00) Future of AI adoption across industries 
(01:25:00) Card trick demonstration
(01:29:00) The Kindest Thing Anyone Has Done For Scott

Scott Wu - Building Cognition - [Invest Like the Best, EP.402]

My guest today is Jared Kushner. Jared has lived more lives than just about anyone I know his age. He ran Kushner companies for years, investing in real estate in and around New York City. He owned the New York Observer. He was a senior advisor to President Trump in his first term. He now runs Affinity Partners, which we discuss in detail, a private equity firm built to find and execute unique investments around the world that stem from Jared's unique set of experiences in business and government. This is one of our longest episodes ever because there was so much to discuss. We cover real estate, negotiation, geopolitics, his work in prison reform, Operation Warp Speed, and the Abraham Accords in the Middle East, business, investing, his family, and everything in between. Jared told me I could ask him about anything--and I really enjoyed doing so. Please enjoy my conversation with Jared Kushner.

My guests today For the full show notes, transcript, and links to mentioned content, check out the episode page here.
-----
﻿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. AlphaSense provides access to over 300 million premium documents, including company filings, earnings reports, press releases, and more from public and private companies. 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. 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 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.
-----
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
(00:08:45) Jared's Philosophy on Challenges and Success
(00:13:38) Real Estate Ventures: The 666 Fifth Avenue Story
(00:20:31) Lessons from New York Real Estate
(00:30:04) Diplomacy and the Middle East
(00:37:03) Leadership and Change
(00:41:14) Geopolitical Landscape and Future Prospects
(00:47:53) Affinity Partners: Vision and Strategy
(00:52:42) Navigating Market Shifts
(00:54:39) Case Study: Mexico Investment
(00:58:34) Global Investment Strategies
(01:02:42) Investment Philosophy and Principles
(01:07:04) Challenges and Problem-Solving
(01:23:14) Government Efficiency and Bureaucracy
(01:34:57) Stepping into the Spotlight
(01:37:19) Manifesting Success with Partners
(01:38:05) Learning from Brad Jacobs
(01:42:09) Middle East Economic Development
(01:46:08) The Qatar-Saudi Reconciliation
(01:52:25) Perceptions of Key Middle Eastern Countries
(02:07:34) Preparing for Trump's Return
(02:14:36) Early Days of Thrive Capital
(02:16:56) Helping Entrepreneurs and Building Thrive
(02:24:51) Lessons from My Father
(02:37:47) Future Vision and AI
(02:48:45) The Kindest Thing Anyone Has Ever Done For Jared

Jared Kushner - The Mechanic - [Invest Like the Best, EP.403]

My guest today is Jack Kokko. Jack is the CEO and Founder of AlphaSense, an AI-powered search engine for market intelligence. He shares how AlphaSense began by aggregating fragmented financial data sources and evolved with the advent of large language models to change the research experience completely. He speaks to their recent acquisition of Tegus earlier this year, reshaping the business and further supporting their expansion to serve all types of companies instead of exclusively investment firms. Jack has been navigating the AI revolution from its earliest days and you can feel his excitement when he talks about the future. We discuss building an agile platform, the importance of managing cultural integration, balancing AI capabilities with user trust, and the frontier for this technology. Please enjoy my conversation with Jack Kokko.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
-----
﻿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. AlphaSense provides access to over 300 million premium documents, including company filings, earnings reports, press releases, and more from public and private companies. 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. 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.
-----
Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
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
(00:08:32) The Evolution of AlphaSense and AI Integration
(00:10:24) Impact of Large Language Models
(00:19:24) User Behavior and Trust in AI
(00:26:24) Future of AI in Investment Research
(00:28:41) The Value of Proprietary Data
(00:31:24) M&A Insights and Lessons Learned
(00:32:59) The Tegus Opportunity and Investor Insights
(00:34:41) Building Trust and Cultural Compatibility in M&A
(00:37:33) Selling to Investors vs. Corporations
(00:40:46) Personal Motivation and Entrepreneurial Journey
(00:47:24) Breaking into the Corporate Market
(00:49:28) Future of AI and Foundational Models
(00:52:04) The Kindest Thing Anyone Has Ever Done For Jack

Jack Kokko - Building AlphaSense - [Invest Like the Best, EP.404]

My guests today are Dwight Churchill and Gaurav Misra, co-founders of Captions, which uses AI to generate and edit talking videos and has grown to significant scale at remarkable speed. We explore a key distinction in AI: tackling bounded problems like video generation versus unbounded problems like general intelligence and what this means for building sustainable businesses. We also explore their unique data flywheel, why video generation could reach Hollywood quality within 18 months, and why building advanced AI products doesn't require huge teams. Please enjoy this discussion with Dwight and Gaurav.

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 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.
– 
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.
-----
Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
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
(00:07:49) The Evolution and Impact of AI
(00:09:14) Challenges in Video Data and AI
(00:10:36) AI in Media Generation
(00:12:07) Building a Sustainable AI Business
(00:14:56) The Journey of a Video AI Company
(00:25:41) AI Video Editing and Creation Tools
(00:29:58) Future of AI in Video and Business
(00:37:51) The Future of Likeness in Video
(00:39:25) Training Models on Human Data
(00:41:15) Competitive Landscape and Copycats
(00:44:01) The Role of Research Talent
(00:46:25) Pricing AI Software
(00:51:51) Investor Perspectives on AI
(01:02:44) Lessons from Snap
(01:07:04) The Kindest Thing Anyone Has Done for Dwight & Gaurav

Gaurav Misra & Dwight Churchill - Building Captions - [Invest Like the Best, EP.405]

My guest today is Tal Zaks. Tal is a physician-scientist turned biotech executive and investor who served as Moderna's Chief Medical Officer during their COVID-19 vaccine development, giving him an extraordinary perspective on one of modern medicine's pivotal moments. His combination of medical expertise, platform innovation experience, and investing acumen allows us to explore the interconnected challenges of turning scientific breakthroughs into viable medicines while generating venture-scale returns. We dive deep into lessons from Moderna's mRNA platform, examine how emerging technologies might reshape drug development, and the fundamental question of what it means to make people healthier. For investors, entrepreneurs, and anyone interested in the future of medicine, this discussion provides a window into both the immense potential and profound challenges of advancing human health. Please enjoy my conversation with Tal Zaks. 

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 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.
– 
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.
-----
Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
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
(00:08:37) State of Medicine Today
(00:09:44) Investment and Innovation in Medicine
(00:13:14) Challenges in Biotech Investment
(00:17:18) Personalized Cancer Vaccines
(00:22:58) Investing in Biotech: Process and Considerations
(00:28:38) Multidisciplinary Approach in Pharma
(00:41:35) COVID-19 Vaccine Development
(00:46:27) Funding and Manufacturing Challenges
(00:48:01) Unprecedented Vaccine Safety Measures
(00:50:38) Public Perception and Trust Issues
(00:53:54) Future of mRNA and Nucleic Acid Medicines
(00:58:04) Personalized Medicine and Data Collection
(01:04:48) AI's Role in Healthcare
(01:08:34) Investment Strategies in Therapeutics
(01:14:57) The Human Element in Medical Innovation
(01:21:58) The Kindest Thing Anyone Has Ever Done for Tal

Tal Zaks - Bridging Science, Medicine, and Returns - [Invest Like the Best, EP.406]

Hedge Fund Manager and author Jeff Gramm talks with Patrick O'Shaughnessy about the history and current state of shareholder activism and discusses how Jeff invests himself, taking large positions and often board seats in undervalued companies.
 
 For comprehensive show notes on this episode go to investorfieldguide.com/gramm/
 For more episodes go to InvestorFieldGuide.com/podcast. 
 Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
 Follow Patrick on twitter at @patrick_oshag

Jeff Gramm – Activist Investing - [Invest Like the Best, EP.01]

Michael Mauboussin, Managing Director and Head of Global Financial Strategies at Credit Suisse, joins Patrick to discuss the current state of the asset management business, explore all of the stages of the investment process, and what edges might exist for those trying to beat the market. 
 
 For comprehensive show notes on this episode go to investorfieldguide.com/mauboussin/
 For more episodes go to InvestorFieldGuide.com/podcast. 
 Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
 Follow Patrick on twitter at @patrick_oshag

Michael Mauboussin – Active Asset Management - [Invest Like the Best, EP.02]

In this episode, Patrick and Jason Zweig reflect on investing, financial advice, books, and life in general. The method for living discussed in the last 30 minutes will be useful for everyone.
 Jason is the Intelligent Investor columnist for the Wall Street Journal and author of several books including his latest “The Devil’s Financial Dictionary.” His insights and advice are the results a life of critical thinking, reading, writing, humility, and curiosity. I think you are going to get a lot from this in-depth conversation. 
 Enjoy!
 
 For comprehensive show notes on this episode go to investorfieldguide.com/zweig/
 For more episodes go to InvestorFieldGuide.com/podcast. 
 Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
 Follow Patrick on twitter at @patrick_oshag

Jason Zweig – The Power of Serendipity - [Invest Like the Best, EP.03]

In this week’s episode, Patrick and Morgan Housel explore the differences between private and public market investing, how to foster innovation and creativity, how businesses are structured and organized, and how Morgan finds interesting books and topics to write about. Morgan is a prolific writer and researcher, who recently left the Motley Fool and is now a partner at the Collaborative Fund, a venture capital fund in New York City. Enjoy!
 
 For comprehensive show notes on this episode go to investorfieldguide.com/housel/
 For more episodes go to InvestorFieldGuide.com/podcast. 
 Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
 Follow Patrick on twitter at @patrick_oshag

Morgan Housel – Walking and Thinking - [Invest Like the Best, EP.04]

This week, to mark the two-year anniversary of the podcast, I offer a quick summary looking back and forward.

Trail Magic - Lessons from Two Years of the Podcast [Invest Like the Best, EP.104]

Trail Magic - Lessons from Two Years of the Podcast [Invest Like the Best, EP.104]

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