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.

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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.

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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. 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.

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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. 

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

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.

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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

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.

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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 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

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.

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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 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

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.

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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 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

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

My guests today are Chetan Puttagunta and Modest Proposal. Chetan is a General Partner at venture firm Benchmark, while Modest Proposal is an anonymous guest who manages a large pool of capital in the public markets. Both are good friends and frequent guests on the show, but this is the first time they have appeared together. And the timing couldn’t be better - we might be witnessing a pivotal shift in AI development as leading labs hit scaling limits and transition from pre-training to test-time compute. Together, we explore how this change could democratize AI development while reshaping the investment landscape across both public and private markets. Please enjoy this discussion with Chetan Puttagunta and Modest Proposal.

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 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.

–

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.

-----

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

(00:05:30) Introduction to LLM Scaling Challenges

(00:07:25) Synthetic Data and Test Time Compute

(00:08:53) Implications of Test Time Compute

(00:11:19) Public Tech Companies and AI Investments

(00:16:58) Small Teams and Open Source Models

(00:29:02) Strategic Positioning of Major AI Players

(00:35:49) AGI and Future Prospects

(00:46:50) AI Application Layer and Investment Opportunities

(00:54:18) The Paradigm Shift in AI Reasoning

(00:55:34) Investing in AI-Powered Solutions

(00:58:46) Economic Impacts of AI Advancements

(01:00:19) The Future of AI and Model Stability

(01:02:52) Private Market Valuations and Compute Costs

(01:05:05) Infrastructure and Utilization in AI

(01:12:50) The Role of Hyperscalers and GPUs

(01:18:02) The Evolution of AI Applications

(01:27:56) Philosophical Questions on AGI and ASI

(01:34:31) The Importance of Innovation Hubs

My guest today is Ronnie Fieg, founder and CEO of Kith. At age 13, Ronnie started working at David Z., an iconic New York shoe store, where he sold Timberland boots to Jay-Z and Wallabies to Wu-Tang Clan. He worked his way up from the stockroom and earned his first collaboration in 2007, when he worked with ASICS on new Gel-Lyte 3s. That collection sold out in a day after being featured in The Wall Street Journal, catching the attention of Adidas's president and launching his reputation as a cultural icon.

In 2011, he founded Kith, which has become one of the most influential brands in footwear, fashion, and culture. The business sells a unique curation of products that includes exclusive Nike sneakers, Armani suits, Versace robes, watches, cars, and even $10 ice creams.

Our conversation is one of the best examples of life's work I've ever recorded - it explores how Ronnie's pure love of product has shaped everything from a campaign with Jerry Seinfeld to his creative direction for the New York Knicks. Please enjoy this excellent conversation with Ronnie Fieg.

Sign up for the Alphasense panel discussion hosted by Patrick.

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

(00:06:10) The Journey to Shoot Jerry Seinfeld

(00:09:44) Understanding Consumer Desires

(00:12:04) The Queens College Project

(00:15:51) The Evolution of Kith Stores

(00:18:03) Ronnie's Early Passion for Collecting

(00:21:56) From David Z to Kith: The Retail Journey

(00:41:36) The Birth of Kith: Friends and Family

(00:46:40) Origins of Kith: From Concept to Brand

(00:47:18) Building Community and Relationships

(00:47:51) The Birth of Kith Stores

(00:48:43) Footwear Passion and Store Design

(00:49:59) The Evolution of Kith Products

(00:50:52) Storytelling Through Film

(00:57:01) Collaborations and Iconic Partnerships

(01:03:38) The Influence of Travel on Design

(01:09:15) Balancing Business and Creativity

(01:16:06) Reflections and Future Aspirations

My guest today is Gabe Whaley, the founder and CEO of MSCHF. What began with viral internet pranks in 2014 has evolved into one of the most singular creative companies in modern culture. MSCHF’s work ranges from microscopic handbags—the size of a grain of salt—to tax software that helps you file your returns by going on virtual dates with anime characters.

Every two weeks, they release something new that challenges our assumptions about art, commerce, and culture. MSCHF is hard to define but Gabe says their goal is to “monopolize a feeling” and subversion is the rare constant. Their most viral creation, the Big Red Boot, took over the internet in 2023.

Our conversation explores how a West Point dropout built a company that thrives on breaking rules, but it's also about something bigger - the power of unbridled creative expression and what happens when you build a business around it. I hope it inspires you to think about what your version of mischief could be. Please enjoy this fascinating discussion with Gabe Whaley.

Sign up for the Alphasense panel discussion hosted by Patrick.

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. 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.

–

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.

-----

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

(00:06:50) Defining Mischief's Unique Creativity

(00:11:09) The Origin Story of Mischief

(00:12:53) Early Digital Projects and Virality

(00:20:33) Transition to Physical Products

(00:33:07) Navigating the Art World with Mischief

(00:39:52) Entering the Fashion World

(00:42:37) Mischief's Creative Process

(00:44:51) Structured Brainstorming and Idea Vetting Process

(00:46:38) The Role of Rules and Boundaries in Creativity

(00:48:39) Interacting with Venture Investors

(00:51:07) The Big Red Boots Phenomenon

(00:54:48) Supply and Demand in Creative Projects

(00:58:08) Protecting Creativity and Overcoming Challenges

(01:00:11) Lessons from West Point

(01:05:25) Fashion as Utility and Fantasy

(01:09:47) Recruiting and Team Dynamics

(01:11:56) Navigating Crossroads and Future Goals

Today, we are replaying my conversation with Brad Jacobs. Brad’s resumé is remarkable. He has founded seven companies, all of which are billion-dollar or multibillion-dollar businesses. He has done 500 M&A transactions and raised $30 billion dollars of debt and equity capital. Currently, he is the Executive Chairman of XPO, a commercial trucking company that he started in 2011 and has grown into one of the largest logistics businesses in the world. He has also written a book that will be out in January, titled “How to Make a Few Billion Dollars”. Brad’s energy is infectious and our conversation unpacks his strategies for M&A, his propensity for speed, and methods for earning team buy-in. Please enjoy my great conversation with Brad Jacobs.

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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 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.

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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.

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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. 

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

(00:00:00) Welcome to Invest Like the Best

(00:07:11) Identifying key factors in a market before investing

(00:10:07) Gleaning insights from early acquisition experiences

(00:13:43) Delving into the seller's mindset during a business sale

(00:17:51) Weighing pre-built against organic growth strategies in acquisitions

(00:27:49) Engaging constructively with Wall Street

(00:29:36) Discussing the substantial buyback of XPO shares

(00:33:16) Ambition as a recurring theme in entrepreneurial success

(00:35:17) Emphasizing the need to facilitate team agility

(00:37:35) Highlighting the joys of post-acquisition integration

(00:41:09) Drawing lessons from Ludwig Jesselson's principles

(00:45:34) Comparing the risks and rewards of early versus late adoption

(00:49:09) Reflecting on errors made in trend analysis

(00:53:59) Strategies for implementing new technologies in enterprises

(00:56:59) The significance of thought experiments in strategic decision-making

(01:01:00) Recalling transformative events from his early years

(01: 02:22) Outlining what makes a meeting 'electric'

(01: 06:53) Sharing experiences with exemplary leadership

(01:12:37) Deciding the right time to step away from a business

(01:23:45) Philosophies for leading a fulfilling life

(01:27:53) The kindest thing anyone has ever done for Brad