Invest Like the Best with Patrick O'Shaughnessy

My guest today is Caryn Seidman-Becker [https://www.linkedin.com/in/carynseidmanbecker/]. Caryn is the Chairman and CEO of Clear. She bought the company out of bankruptcy for $6 million in 2010 and built it into the identity platform millions use in airports and stadiums today. Her Wall Street background investing in Apple, Amazon, and Priceline taught her to recognize when products become platforms, which shaped her vision for Clear as the "definitive secure identity platform" far beyond travel. Caryn shares the gritty early days of literally hunting down hardware in airport storage facilities and rebuilding the entire business from scratch. She embodies an incredible "bias for action." We discuss turning around a business, scaling a platform, and why she believes your face will soon be your key to everything. Please enjoy my conversation with Caryn Seidman-Becker. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠here [https://joincolossus.com/episode/rebuilding-clear/].⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. 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. Go to⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/]⁠ ⁠Arcana⁠⁠ [https://www.arcana.io/]. Arcana is the world’s most advanced portfolio intelligence platform, trusted by institutional investors managing trillions in AUM — including market neutral, long-short, long-only, and capital allocators. Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and idio, construct optimal portfolios, and decompose performance at incredible granularity. Visit⁠ ⁠arcana.io⁠⁠ [http://arcana.io/] to request a demo and learn more. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/]. 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. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:43) The Vision for CLEAR (00:09:08) From Wall Street to CLEAR (00:13:42) The Origins of CLEAR (00:14:23) The Bankruptcy and Rebirth of Clear (00:34:41) Building the Business Model (00:47:46) The Future of Airport Innovation (00:48:33) Investing Insights and Strategies (00:52:17) The Importance of Free Cash Flow (00:55:26) Biometrics and Privacy Concerns (00:59:40) Expanding Clear's Vision (01:04:13) Personal Mission and Genetic Screening (01:12:28) Leadership and Company Culture (01:14:23) Future of Technology and Identity (01:25:38) The Kindest Thing Anyone’s Ever Done For Caryn

My guest today is Jens Grede [http://linkedin.com/in/jens-grede-833431b7]. Jens is the co-founder and CEO of Skims, the shapewear and clothing brand he co-founded with his wife Emma Grede and Kim Kardashian. Our conversation left my head spinning. Jens has this remarkable ability to be both creative and commercial. He puts brilliant frameworks into plain terms and knows consumer like the back of his hand. Jens explains how pop culture is the only remaining hack to the consumer economy in our fragmented media landscape and describes today’s cultural shift as "clamoring for comfort" in uncertain times. We discuss individual voices trumping institutions, moving at the speed of culture rather than corporate planning cycles, and why big brands will increasingly win. Please enjoy this fascinating discussion with Jens Grede. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠ ⁠⁠⁠⁠here.⁠⁠⁠⁠⁠⁠⁠ [https://joincolossus.com/episode/building-skims/] ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. 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. Go to⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠ [https://www.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 [https://www.ridgelineapps.com/]. 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. Head to⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:18) The Power of Pop Culture in Business (00:09:28) The Role of Individuals vs. Institutions (00:11:27) Cultural Shifts: From Hip Hop to Country (00:18:36) The Resurgence of Fallen Brands (00:24:33) The SKIMS Origin Story (00:33:42) Building a Strong Product and Brand (00:36:14) The Partnership with Kim Kardashian (00:49:18) Effective Content Creation in Popular Culture (00:50:55) Decision Making in Real-Time (00:51:35) Leveraging Popular Culture for Brand Success (00:57:28) The Role of Networks and Individual Voices (01:14:38) The Future of Status and Digital Influence (01:16:20) Investing Insights and Long-Term Views (01:20:39) Scaling SKIMS and Future Plans (01:23:52) Reflections on Entrepreneurship and Personal Growth (01:29:49) The Kindest Thing Anyone Has Ever Done For Jens

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people.  Charlie Songhurst [https://www.linkedin.com/in/charlessonghurst/] is a brilliant strategist, accomplished executive, and prolific angel investor. This episode is one of my all-time favorite conversations, not just on the podcast, but period. Please enjoy this timeless discussion with Charlie Songhurst. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠here⁠ [https://joincolossus.com/episode/songhurst-lessons-from-investing-in-483-companies/]. ----- This episode is brought to you by ⁠⁠WorkOS⁠⁠ [https://workos.com/]. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠⁠WorkOS.com⁠⁠ [https://workos.com/] to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit ⁠joincolossus.com/episodes⁠ [https://www.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 [https://www.joincolossus.com/newsletter]. Follow us on Twitter: ⁠@patrick_oshag⁠ [https://twitter.com/patrick_oshag] | ⁠@JoinColossus [https://twitter.com/JoinColossus] Show Notes (00:00:00) Welcome to Invest Like the Best (00:01:25) Stack ranking the vices of power, money, and fame (00:02:41) Memorable response to the stack ranking question (00:03:13) Best scenario to explore this stack ranking concept (00:03:55) Other ways to rank founders (00:04:44) Quick look at this career (00:05:16) Time at Microsoft (00:06:03) Features he looks for in startups (00:10:55) Managing the declining curve of productivity (00:14:55) Why founders are often unique people (00:14:57) ⁠Jeff Gramm Podcast Episode⁠ [http://investorfieldguide.com/gramm/] (00:15:04) ⁠ Aliens, Jedi & Cults⁠ [https://medium.com/balance-io/aliens-jedi-%EF%B8%8F-cults-b1d52b681b8] (00:09:43) How early entrepreneurs need to make recruitment a serious part of their work (00:23:06) How successful founders win the best candidates (00:25:27) The East Coast vs. West Coast investment strategies (00:30:40) When it’s time to bring in quantitative factors into early stage investing (00:34:36) The markers that pop up in companies that hit (00:37:22) Boring but successful investments (00:39:28) Investor aesthetics (00:41:29) Characteristics of investors that he believes are important to success (00:42:57) Impacts of Covid and some of the permanent changes that have happened as a result (00:47:49) Investing opportunities in the local community (00:49:13) His take on cryptocurrencies (00:53:47) Most misvalued asset in the world (00:55:16) Investing opportunities in Europe (00:57:34) Make up of his 483 investments (00:57:58) ⁠Matt Clifford Podcast Episode⁠ [http://investorfieldguide.com/clifford/] (00:59:17) Curation as a skill (01:01:54) Timing and startup success (01:05:11) Kindest thing anyone has done for him

My guests today are Alex Pall [https://x.com/TheChainsmokers] and Drew Taggart [https://x.com/TheChainsmokers], who you might know as The Chainsmokers. We explore their fascinating evolution from scrappy DJs to global superstars to serious venture capitalists with their fund Mantis. Drew and Alex share how the same high-touch, relationship-driven approach that built their music empire now defines their investment philosophy. Their framework for backing founders mirrors their artistic process: they invest in obsessive individuals who will pursue their vision regardless of external validation, much like how they've remained authentic to their sound despite industry pressures. We discuss parallels between creative iteration in music and venture investing, particularly around managing failure, maintaining intentionality in an age of abundance, and the importance of taste as a differentiating factor. Please enjoy this fascinating discussion with The Chainsmokers, Alex Pall and Drew Taggart.  For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠ ⁠⁠⁠⁠here.⁠⁠⁠⁠⁠⁠ [https://joincolossus.com/episode/music-markets/] ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. 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. Go to⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/]. 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. Head to⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] to learn more about the platform. –  This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] ⁠Arcana⁠ [https://www.arcana.io/]. Arcana is the world’s most advanced portfolio intelligence platform, trusted by institutional investors managing trillions in AUM — including market neutral, long-short, long-only, and capital allocators. Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and idio, construct optimal portfolios, and decompose performance at incredible granularity. Visit ⁠arcana.io⁠ [http://arcana.io/] to request a demo and learn more. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:16) The Creative Process Behind Songwriting (00:07:33) Exploring the Emotional Depths of Music (00:11:50) Navigating the Music Industry and AI (00:17:45) The Importance of World Building in Music (00:21:27) Finding Your Creative Itch (00:35:04) The Chainsmokers' Journey and Work Ethic (00:40:37) The Business Side of the Chainsmokers (00:45:43) Venturing into Tech and Investments (00:51:39) The Evolution of Mantis (00:53:11) Overcoming Celebrity Investor Stereotypes (00:55:20) Supporting Founders Like Record Labels (00:57:26) The Art of Collaboration (01:04:02) The Grind to Success (01:13:49) Investing Insights and Evolution (01:26:39) The Kindest Thing Anyone Has Ever Done for Drew and Alex

My guest today is Jay Hoag [https://www.tcv.com/team/jay-hoag]. Jay is the co-founder of Technology Crossover Ventures, known as TCV, which pioneered the growth investing category and has backed legendary companies like Netflix, Spotify, and Expedia over three decades. Jay explains how macro factors like regulation have become unexpectedly central to technology investing. He offers his contrarian take on today's market, arguing that consumer internet represents significant opportunity while most investors chase SaaS and AI deals. We discuss investing in new technology versus commercialization, TCV’s evolution from cold-calling to AI-powered sourcing of 11 million companies, and their three-person unanimous investment committee structure. Please enjoy my conversation with Jay Hoag.  For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ ⁠⁠⁠⁠here.⁠⁠⁠⁠⁠ [https://joincolossus.com/episode/keys-to-successf%E2%80%A6growth-investing/] ----- This episode is brought to you by⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. 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. Go to⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/]. 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. Head to⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] to learn more about the platform. –  This episode is brought to you by⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:18) Market Conditions and Investment Opportunities (00:06:57) Consumer Internet Businesses and AI (00:09:04) Technology Commercialization Challenges (00:11:30) Public vs. Private Market Dynamics (00:15:32) Growth Investing and Competitive Dynamics (00:22:34) History and Resilience of TCV (00:26:32) Understanding the Firm's Investment Lifecycle (00:27:06) Evolution of Sourcing Strategies (00:28:33) The Role of Data Intelligence in Sourcing (00:29:41) Internal Investment Process at TCV (00:34:31) Challenges and Strategies in Long-term Investments (00:41:15) Reflections on the Investment World (00:43:48) Personal Insights and Final Thoughts