Invest Like the Best with Patrick O'Shaughnessy Podcast

My guest today is Bill Gurley. Bill was the general partner at Benchmark Capital. He joins me for his sixth time on Invest Like the Best with his most comprehensive market analysis yet, examining the realities reshaping venture capital. Bill tackles the uncomfortable math underlying today's venture returns, with companies staying private for far longer. He also walks through why no onefrom GPs to LPs to foundershas proper incentives to mark assets accurately, creating a system-wide coordination problem. And, we dig into the investment implications of AI as a platform shift, ranging from evaluating AI revenue quality to international competitive dynamics. Bill offers crucial perspective on playing the game both as it exists today and as it may evolve. Please enjoy my conversation with Bill Gurley.



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. Ramps 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 to sign up for free and get a $250 welcome bonus.



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. Head to ridgelineapps.com to learn more about the platform.



This episode is brought to you by Arcana. Arcana is the worlds 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 to request a demo and learn more.

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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

(00:05:23) State of the Union: Venture Capital Edition

(00:07:58) The Rise of Mega VC Funds

(00:09:38) Zombie Unicorns: The Overvalued Giants

(00:17:29) The IPO and M&A Market Stalemate

(00:24:08) The AI Wave and Its Impact

(00:26:03) Private Markets and LP Liquidity Issues

(00:29:57) The Future of Capital Markets

(00:37:49) Advice for Founders in a Changing Landscape

(00:39:27) The High-Stakes Game of Capital Battles

(00:41:35) AI: The New General Purpose Technology

(00:42:57) Challenges and Opportunities in AI Revenue Models

(00:44:37) The Role of Founders in the AI Revolution

(00:46:44) The Impact of Time and Liquidity on Venture Capital

(00:50:35) Navigating the Future of Venture Capital

(00:58:45) International Dynamics in the AI Race

(01:13:58) Advice for Founders in the AI Era

Today, we are dropping a special episode in the Invest Like the Best Feed. 50X is back, a fan favorite series from Will Thorndike and the team at Compounding Labs. Will's book, "The Outsiders," is one of the best business and investing books that you'll find. You'll hear him continuing his work in the hosting chair as he looks in detail at investments that have appreciated at least 50-fold.Season two features Asurion. Colossus is excited to partner with Will as he sits down with the management and investors behind this legendary investment. We kick off this special drop with a short interview that I did with Will on everything he learned studying this business, followed by the full three-part series.







Learn more and dive into our research at ⁠50xpodcast.com⁠

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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. 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 ⁠Oberle⁠. Oberle is a specialty insurance brokerage providing insurance services to search funds, independent sponsors, family offices, and private equity firms.

Oberle supports its clients with a comprehensive insurance due diligence covering a wide range of items, including commercial insurance, Employee Benefits, key person life insurance, and reps and warranty coverage. Additionally, Oberle has a thriving personal lines practice, designed for entrepreneurs seeking a higher-level service and expertise when it comes to insuring one’s home, vehicles, and valuables.

If you’re interested in connecting with the Oberle team:  ⁠https://oberle-risk.com/50x⁠

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This episode is brought to you by ⁠System Six⁠, 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 headache 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 [email protected] mention the podcast for your first month of ongoing bookkeeping free.

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50X is a property of Colossus, LLC. For more episodes of 50X, visit⁠⁠⁠ joincolossus.com/episodes⁠⁠⁠.

Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠).

Follow us on Twitter: @50Xpodcast | @joincolossus



Show Notes

(00:00:00) Welcome to 50X

(00:04:52) Patrick interviews Will Thorndike

(00:18:16) The Early Days (‘95-‘01) with Kevin Taweel

(01:24:44) The Flywheel Era (‘01-‘07) with Kevin Taweel

(02:24:32) Retracing the Path to 100 times 50x with Irv Grousbeck

My guest today is John Zito. John is the Co-President of Apollo Global Management. He shares how they've quietly built one of the most important financial institutions of our time, originating over $250 billion annually. John's thesis on the convergence of private and public markets - and Apollo's positioning to capture 100% of client portfolios rather than just alternatives allocations - offers a fascinating glimpse into where institutional investing is heading. We discuss the cultural and strategic elements that drive John, Apollo’s merger with Athene, the idea of artistry at scale, and the evolution of capital markets. Please enjoy my conversation with John Zito. 



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. 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 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. Head to⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠ to learn more about the platform.

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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. 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.

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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

(00:05:55) The Rise of Apollo and Credit Markets

(00:08:05) Innovations in Asset Management

(00:11:42) The Role of the US in Global Capital Markets

(00:15:26) The Future of Asset Management and Investment Strategies

(00:21:03) The Impact of Interest Rates on Investment

(00:25:27) Apollo's Business Model and Growth

(00:25:17) The Changing Landscape of Private Markets

(00:46:03) Apollo's Culture and Vision

(00:47:54) The Importance of Company Culture

(00:52:52) The Future of Private and Public Markets

(00:57:50) Building a Great Origination Platform

(01:02:03) Exciting Deals and Personal Stories

(01:14:47) The Role of AI and Future Opportunities

(01:22:16) Maintaining Company Culture Amidst Change

(01:24:06) The Kindest Thing Anyone Has Ever Done For John

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. 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.

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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.

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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. 

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

(00:03:51) 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. 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.⁠⁠

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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. 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. 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. Head to⁠⁠ 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).

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