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. In the midst of her transition to OpenAI, we are spotlighting the force that is Fidji Simo [https://twitter.com/fidjissimo?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor]. She is the former CEO of Instacart and grew up in a small town in the South of France and was the first person in her family to graduate from high school. Since then, she has had a dazzling career with stops at France’s leading university, eBay, and Facebook. Fidji spent the better part of a decade at Facebook where she led the Facebook App before joining the online grocery platform, Instacart, in mid 2021. We talk about Fidji’s consumer product experiences, Instacart’s role within the grocery ecosystem, and delve into her personal philosophy on leadership. Please enjoy this wide-ranging discussion with Fidji Simo. For the full show notes, transcript, and links to mentioned content, check out the episode page here [https://joincolossus.com/episodes/80275266/simo-creating-delightful-consumer-experiences]. ----- 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 (00:03:51) Comparing her experiences with Facebook and Instacart (00:06:22) The dimensionality of creating great consumer products online (00:07:50) How Instacart uses AI now and her advice to other companies who are ready to incorporate AI into their business (00:15:41) What being a pragmatic technologist means to her (00:18:02) Influences in younger years that led to her career path in technology (00:21:00) The landscape Instacart seeks to build and how major key players within the industry are involved (00:27:09) Data algorithms and their role in helping consumers (00:29:24) Scale around the original core business (00:32:12) The functional difference between Instacart shoppers and delivery drivers  (00:34:59) Issues with fully automated grocery store facilities (00:37:32) Insight into working with brands and consumer brand loyalty  (00:43:16) Her vision for the future of Instacart (00:46:58) The possibility of becoming the major software platform for most retailers (00:49:34) Her principles for capital allocation (00:52:34) Common misperceptions about Instacart from prospective investors (00:54:21) Her philosophy of seeing the magic in team members (00:56:46) Expanding knowledge while managing a complex business environment   (01:01:01) When she felt the most helpless in her career (01:03:46) Insight into generative AI and how it could shape the online grocery experience (01:08:00) The role of content and its importance for businesses like Instacart (01:11:10) The future of AI personalities and customizing your shopping experience (01:12:35) The kindest thing anyone has ever done for her

My guest today is Graham Weaver [https://www.grahamweaver.com/]. My guest today is Graham Weaver. Graham is the founder of Alpine Investors, a large private equity firm targeting an interesting market inefficiency. Alpine focuses on the thousands of $20 million revenue businesses whose baby boomer owners want to retire, but lack succession plans. Alpine buys companies and installs 28-year-old military veterans and top MBA graduates as CEOs, leveraging 25 years of intellectual property on how young executives can successfully run established businesses. Alpine's CEO-in-training program is now the most applied-to job at Harvard, Stanford, and Kellogg business schools. We discuss the past, present and future of their unique approach. Please enjoy my conversation with Graham Weaver. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠ here.⁠⁠ [https://joincolossus.com/episode/building-alpine/] ----- 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 (00:05:13) The Journey to Private Equity (00:06:59) Early Influences and Personal Growth (00:09:54) The Power of Wrestling and Rowing (00:11:45) Choosing Your Path and Making Decisions (00:14:48) College Goals and Rowing Success (00:18:05) Lessons from Early Business Ventures (00:26:24) Founding Alpine and Early Challenges (00:34:46) Core Beliefs and Talent Development (00:39:07) Fun Board Meetings and Team Dynamics (00:40:42) Platform Building 101 (00:44:08) Talent and Training Programs (00:49:12) Employee and Customer Engagement (00:52:27) Financial Outcomes and Asymmetric Returns (00:55:52) Incentivizing Young CEOs (01:00:26) The Role of Emotional Intelligence (01:02:45) The Alpine CEO in Training Program (01:03:40) Teaching at Stanford and Influential Mentors (01:07:58) Helping Students Find Their Passion (01:10:22) Visualizing Your Future Self (01:11:19) Scalability of Coaching (01:12:15) Personal Growth Through Teaching (01:16:16) The Role of Executive Coaching (01:24:45) Lessons from a Bad Deal (01:31:50) Daily Routines and Success (01:36:13) The Future of Private Equity (01:35:24) Unleashing Heroes at Alpine (01:38:09) The Journey of Building Alpine (01:41:31) The Kindest Thing Anyone Has Ever Done For Graham

My guest today is Gustav Söderström [https://www.linkedin.com/in/gustavsoderstrom/?originalSubdomain=se]. Gustav is the Co-President, Chief Product Officer & Chief Technology Officer at Spotify. Gustav lets us behind the scenes on how Spotify thinks about the future of audio and video, and what leadership lessons he's learned from making mistakes and taking risks in a rapidly changing technological landscape. He shares fascinating insights on their synchronized team structure and how they have positioned themselves as "the R&D department" for the entire music industry. We discuss their integration of AI, their unique "bets board" process for allocating resources, and how they've evolved from a music service into a multimedia platform with over 650 million users. Please enjoy my conversation with Gustav Söderström. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ [https://joincolossus.com/episode/how-spotify-thinks/] ----- 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 (00:05:27) Spotify's Journey Through Technological Shifts (00:06:28) The Impact of Generative AI on Consumer Products (00:09:36) AI in Coding and Productivity (00:11:11) Consumer Engagement and AI Playlisting (00:14:43) Strategic Frameworks and Decision-Making at Spotify (00:19:39) The Bets Process: Structured Innovation (00:31:11) The Future of AI and Business Models (00:44:31) The Future of AI and Inference Costs (00:46:21) The Concept of Computronium and Infinite Computing (00:47:02) David Deutsch and the Beginning of Infinity (00:48:55) The Power of Explanations and Human Understanding (00:54:03) Spotify's Free Tier and Consumer Needs (00:56:45) Spotify's Relationship with the Music Industry (01:03:03) The Rise of Podcasting and Audiobooks (01:15:45) Personal Interests and Continuous Learning (01:20:32) The Kindest Thing Anyone Has Ever Done For Gustav

Today, we are dropping a special episode in the Invest Like the Best feed. You will hear the first episode of ⁠50X⁠ [https://www.50xpodcast.com] Season Two – a series from Will Thorndike and the team at Compounding Labs, in partnership with Colossus.  This episode is the first in a series of three on Asurion, the world’s leading tech care company with more than 300 million customers. In an interview with Co-Founder and Chairman ⁠Kevin Taweel⁠ [https://www.linkedin.com/in/kevin-taweel-29300393/], we explore Asurion’s scrappy origins in roadside assistance, acquisitive entry into handset insurance, contentious capital allocation decisions, and much more.   In each episode of 50X, we look in detail at an investment that has appreciated at least 50-fold. From the seat of the professional investor and occasionally the CEO, we explore its origins, evolution, and eventual outcome, studying key themes around long-term value creation ranging from operations, capital allocation, and culture to pivotal buy and sell decisions. To enhance the quality and depth of our interviews, we rigorously study each asset in advance, diving into all available public and private resources. Make sure to subscribe to ⁠⁠50X⁠⁠ [https://www.50xpodcast.com] in your preferred podcast player.⁠ [http://50xpodcast.com/]   For the full show notes, transcript, and links to the best content to learn more, check out the episode page⁠ here.⁠ [https://joincolossus.com/episode/asurion-the-earl%E2%80%A6ith-kevin-taweel/] —- 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 ⁠System Six⁠⁠ [https://systemsix.com/], a searcher-owned outsourced bookkeeping and accounting services firm that has been a great partner to us at Compounding Labs.  With the right modern tools and a strong team, System Six will eliminate headaches for you and give you time back so you can focus on growing your business. Whether you're a CEO or CFO stuck in the weeds, or an investor trying to support your CEOs and portfolio companies, reach out to hello@systemsix.com and mention the podcast for your first month of ongoing bookkeeping free. —- 50X is a property of Colossus, LLC. For more episodes of 50X, visit⁠ joincolossus.com/episodes⁠ [https://www.joincolossus.com/episodes]. Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠ [https://thepodcastconsultant.com/]). Follow us on Twitter: @50Xpodcast | @joincolossus Show Notes (00:00:00) Welcome to 50X (00:01:59) Sponsorship: Ramp (00:03:16) Sponsorship: System Six (00:04:24) Introduction to Kevin and Asurion (00:05:55) Kevin’s Background Pre-Asurion (00:13:31) Origin of Kevin’s Search Fund (00:19:51) Acquiring Road Rescue (00:28:03) Operating Road Rescue (00:39:21) Early Success: Hold or Sell — a Critical Early Decision? (00:44:51) Entry into Handset Insurance: Acquiring the Merrimac Group (00:52:31) Vertical Integration (00:58:31) Capital Allocation in the Search Fund Period (01:02:31) TA Investment

My guests today are Rick Ruback [https://www.hbs.edu/faculty/Pages/profile.aspx?facId=6543] and Royce Yudkoff [https://www.hbs.edu/faculty/Pages/profile.aspx?facId=589675]. Rick and Royce are Harvard Business School professors who teach their students how to search for, acquire, and run small business directly after graduation. It has been almost a decade since our first conversation, and unlike many past interviews that have become outdated due to technology or market changes, the core principles they shared about entrepreneurship through acquisition remain remarkably relevant today. They explore fascinating developments in the search-fund ecosystem, including the bifurcation between funded searchers targeting larger companies and self-funded entrepreneurs finding success with smaller businesses. Rick and Royce share their accumulated wisdom on what makes a company worth buying, why the "magic is in the multiples," and how their students consistently achieve impressive returns through patient, value-oriented business acquisition. Please enjoy my conversation with Rick Ruback and Royce Yudkoff. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ [https://joincolossus.com/episode/entrepreneurship%E2%80%A6ough-acquisition/] ----- 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 (00:05:23) Changes in the Small Firm Acquisition Space (00:06:52) The Impact of SBA Loans on Acquisition Entrepreneurship (00:08:55) The Evolution of Entrepreneurship Through Acquisition (00:10:09) Risk and Return in the Search Fund Model (00:13:38) The Role of Investors in Funded and Unfunded Searches (00:19:33) Criteria for a Good Acquisition Target (00:28:36) The Growing Popularity of Self-Funded Searches (00:43:21) Challenges and Red Flags in Small Firm Acquisitions (00:49:47) Exploring Margin Expansion and Growth (00:51:02) The Impact of Practical Teaching in Business Education (00:52:12) Keys to a Successful Business Class (00:53:30) The Role of Theory in Practical Business Education (00:55:29) Challenges and Rewards of Teaching Business (00:57:46) Capital Allocation in Small Businesses (01:00:50) Advice for Aspiring Business Searchers (01:03:45) Value Creation and Business Lifecycle (01:08:20) Deciding to Leave Private Equity (01:11:20) The Future of Higher Education in Business (01:16:06) Ongoing Relationships with Former Students (01:18:45) Favorite Business Cases to Teach (01:24:46) Encouraging More People to Pursue Business Ownership