Invest Like the Best with Patrick O'Shaughnessy

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. Brad Jacob's simple principle of "think big, move fast" is one I think about often. 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 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 is a true force of nature, and I hope you enjoy his episode. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by ⁠⁠⁠WorkOS⁠⁠⁠. 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 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.  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 Show Notes (00:00:00) Welcome to Invest Like the Best (00:02:11) Identifying key factors in a market before investing (00:05:07) Gleaning insights from early acquisition experiences (00:08:43) Delving into the seller's mindset during a business sale (00:12:51) Weighing pre-built against organic growth strategies in acquisitions (00:17:20) Defining the elements of an ideal business (00:22:49) Engaging constructively with Wall Street (00:24:36) Discussing the substantial buyback of XPO shares (00:28:16) Ambition as a recurring theme in entrepreneurial success (00:30:17) Emphasizing the need to facilitate team agility (00:32:35) Highlighting the joys of post-acquisition integration (00:36:09) Drawing lessons from Ludwig Jesselson's principles (00:40:34) Comparing the risks and rewards of early versus late adoption (00:44:09) Reflecting on errors made in trend analysis (00:48:59) Strategies for implementing new technologies in enterprises (00:51:59) The significance of thought experiments in strategic decision-making (00:56:00) Recalling transformative events from his early years (00: 57:22) Outlining what makes a meeting 'electric' (01: 01:53) Sharing experiences with exemplary leadership (01:05:02) Strategies for maximizing team potential (01:07:37) Deciding the right time to step away from a business (01:08:58) Unveiling unexpected challenges in entrepreneurship (01:18:45) Philosophies for leading a fulfilling life (01:21:04) Finishing How To Make A Few Billion Dollars (01:22:53) The kindest thing anyone has ever done for Brad

Zach Dell, co-founder and CEO of Base Power Company, dives into the complexities of the electrical grid and the urgent need for updates to meet rising demand from AI and electric vehicles. He introduces innovative solutions like distributed home batteries that not only offer backup power but also support the grid. Dell emphasizes the pivotal role of affordable energy in driving human progress, discusses the evolution and financing of battery technologies, and outlines Base's unique approach to energy management for Texas homeowners.

Alan Waxman, co-founder and CEO of Sixth Street, takes listeners on a captivating journey through innovative investing. He shares insights from his days at Goldman Sachs and how they shape Sixth Street's unique strategies. Waxman discusses significant investments in Spotify and Airbnb during tough times, and the exciting sports partnerships with Real Madrid and FC Barcelona. He emphasizes the importance of an ego-less hiring approach and Sixth Street's 'face the tiger' philosophy, which encourages a culture of collaboration and adaptability in dynamic market landscapes.

Caryn Seidman-Becker, Chairman and CEO of Clear, transformed a bankrupt company into a leading secure identity platform. She recalls the early gritty days of sourcing hardware and rebuilding the business. Caryn shares insights on evolving identity verification, emphasizing innovation's role. She discusses balancing decisive actions with reflective leadership, tackling challenges in the travel industry, and embracing technology. With a vision for the future, she believes your face will soon become the key to everything, revolutionizing how we interact with security.

Jens Grede, co-founder and CEO of Skims, dives into the captivating intersection of pop culture and commerce. He argues that understanding consumer behavior is crucial in today's fragmented media landscape, noting how cultural shifts demand comfort and authenticity. Grede discusses the resurgence of brands like Abercrombie & Fitch and the importance of adapting to market changes. He highlights the unique challenges of scaling a fashion label while maintaining cultural relevance and emphasizes the evolving trust dynamics in digital media, where individual influencers are gaining prominence.

Charlie Songhurst, former head of strategy at Microsoft and prolific angel investor, shares invaluable investing insights from his experience with nearly 500 companies. He discusses the contrasting investment philosophies of the East and West coasts, emphasizing the importance of balancing quant and qual strategies. The conversation delves into navigating remote work while exploring cryptocurrencies like Bitcoin and Ethereum. Additionally, Songhurst highlights the complexities of investing, the influence of strong mentorship, and how hiring dynamics shape startup success.

In this engaging discussion, Alex Pall and Drew Taggart, the duo behind The Chainsmokers, unveil their transition from music superstars to insightful venture capitalists with their fund, Mantis. They explore the parallels between creativity in music and investing, advocating for authenticity and the importance of taste. The pair shares their personal journeys, emphasizing the significance of resilience through failure and maintaining intentionality in an oversaturated market. Their insights into building connections and navigating the business landscape remind us that passion and people drive both music and investment.

In this engaging discussion, Jay Hoag, co-founder of Technology Crossover Ventures, shares his pioneering insights into growth investing. He emphasizes the importance of macroeconomic factors affecting technology investments and presents a contrarian view that consumer internet holds significant potential over the trending SaaS and AI sectors. Jay reveals how TCV has evolved from traditional cold-calling to AI-driven sourcing, and he dives into the unique structure of their three-person investment committee, showcasing the balance between aggressive and conservative investment strategies.

Dinakar Singh, founder and CEO of Axon, shares a heartfelt journey marked by his child's battle with spinal muscular atrophy (SMA). He explores the emotional and financial motivations behind his commitment to developing life-saving drugs. Discussing the challenges of gene therapy and the pressing need for innovative treatments, he highlights grassroots efforts and collaboration in the biotech industry. Singh emphasizes the importance of community support and reforms to improve access to essential medications for families facing rare diseases.

Bill Gurley, a general partner at Benchmark Capital, shares his in-depth market analysis, focusing on the often-overlooked issues in venture capital as companies remain private longer. He discusses the misaligned incentives among GPs, LPs, and founders, leading to valuation challenges. The conversation also delves into the transformative impact of AI, likening it to past technology revolutions, and examines its implications for investment strategies. Gurley offers vital insights on adapting to the shifting investment landscape.