Invest Like the Best with Patrick O'Shaughnessy

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. 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 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

My guest today is Ernie Garcia. Ernie is the co-founder and CEO of Carvana. Ernie joined me on Founder’s Field Guide in 2021 and despite all that the business has gone through since that conversation, you’ll hear how he has the exact same demeanor and crystal clear vision for the business and its operations today. Carvana is one of the most remarkable business turnaround stories in recent history, and Ernie gives us a raw and candid explanation of navigating through a 99% stock price decline and ultimately emerging stronger on the other side. I don’t know many leaders who could survive this. He credits his team of A players again and again for successfully weathering the storm and maintaining morale. We discuss leading through crisis, building for the long term, and a focus on ruthless prioritization and efficiency gains. Please enjoy my conversation with Ernie Garcia.  Check out our new print publication Colossus Review. 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 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 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.  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 (00:06:00) Carvana's Journey (00:07:38) Facing the COVID-19 Challenge (00:08:12) The Rise and Fall: Carvana's Rollercoaster (00:10:05) Leadership and Resilience in Tough Times (00:14:32) Handling Drawdowns and Communication (00:16:58) Maintaining Calm and Leadership (00:18:19) The True Story of Carvana's Journey (00:20:36) Navigating Market Challenges (00:23:40) Learning to Say No (00:30:35) Project Management and Accountability (00:34:22) The Importance of Player-Coach Leadership (00:35:53) The Importance of Vertical Integration (00:40:43) Customer Experience and Vertical Integration (00:41:41) Navigating Economic Variables (00:43:52) Building Resilience in Business (00:45:27) Balancing Personal and Professional Life (00:48:57) Efficiency and Growth in Carvana (00:59:02) Insights on Investors and Entrepreneurship (01:02:42) Lessons from Family and Origins of Carvana (01:11:22) The Kindest Thing Anyone Has Done For Ernie

My guests today are Andrew Homan and Chris Miller. Andrew has spent two decades at Maverick Capital and is a managing partner at Maverick Silicon, where he leads the firm’s technology investments. Chris is a professor at Tufts and the author of the New York Times best-selling book “Chip War,” which details the geopolitical battle to control the semiconductor industry. Together we get into a comprehensive discussion on the semiconductor ecosystem and the silicon backbone of our digital age. Andrew and Chris share insights on how venture capital is navigating this complex industry and what it means for the future of computing. We discuss the AI-driven revolution in chip demand, the geopolitics of semi-manufacturing, and the next wave of innovation beyond NVIDIA. Please enjoy my conversation with Andrew Homan and Chris Miller. 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 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.  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 (00:06:28) Intel's Historical Success and Current Challenges (00:08:22) The Paradigm Shift in Technology (00:11:44) AI and the Future of Semiconductors (00:19:02) Political and Economic Considerations in Chip Manufacturing (00:29:28) Investment Perspectives and Market Dynamics (00:45:46) The Mobile Paradigm Shift: Apple vs. AT&T (00:46:49) Corporate Strategies in the AI Transition (00:48:02) NVIDIA's Dominance and Potential Vulnerabilities (00:51:27) The Future of Edge AI (00:57:02) Powering the Data Centers of Tomorrow (00:59:42) The Semiconductor Startup Ecosystem (01:05:08) The Role of Government and Global Dynamics (01:07:28) Investment Strategies and Market Dynamics (01:10:57) The Future of the Semiconductor Industry (01:25:52) The Kindest Thing Anyone Has Ever Done For Chris And Andrew