Graham Weaver - Building Alpine - [Invest Like the Best, EP.425]
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.
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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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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
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1:29:57
Gustav Söderström - How Spotify Thinks - [Invest Like the Best, EP.424]
My guest today is Gustav Söderström. 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.
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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.
–
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
(00:05:27) 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
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1:23:33
Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]
My guests today are Rick Ruback and Royce Yudkoff. 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.
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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.
–
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
(00:05:23) 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
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1:27:52
David Senra - The Focused Few - [Invest Like the Best, EP.422]
My guest today is David Senra. David is the host of Founders podcast and a dear friend. This is our third time doing Invest Like the Best together and we have conversations like this one all the time. In today’s episode, David distills wisdom from 400 entrepreneur biographies into a single word: focus. He reveals why exceptional builders like Todd Graves and James Dyson create billion-dollar empires through obsessive dedication to simple ideas—whether perfecting chicken fingers or designing vacuum cleaners—while rejecting conventional growth timelines and investor pressure. David challenges us all to find the one thing we’d pursue even without recognition or reward, or what I like to call your life’s work. We discuss the concept of “anti-business,” raising capital as a founder, and decades-long commitment. Please enjoy this discussion with David Senra.
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.
–
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
(00:05:43) The Essence of Focus in Entrepreneurship
(00:09:20) The Value of Long-Term Commitment
(00:17:41) The Importance of Simplicity and Mastery
(00:37:11) The Miracle of Entrepreneurship
(00:44:56) James Dyson's Journey to Success
(00:47:03) The Importance of Passion in Business
(00:49:12) Critique of Modern Consumerism
(00:52:18) The Value of Craftsmanship
(00:56:36) The Drive for Excellence
(01:04:06) The Importance of Hiring Top Talent
(01:09:54) Creative Financing Strategies
(01:19:35) Defining a Founder
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1:20:37
Cliff Sosin - Investing in Carvana - [Invest Like the Best, EP.421]
My guest today is Cliff Sosin. Cliff is the founder of CAS Investment Partners, a fund he started with $5 million in 2012 and has grown to $1.7 billion as of the last reported numbers at the end of 2024. At the time, CAS had only four positions.
This conversation is different to our typical episodes. We start by talking about Cliff's investing philosophy but the bulk of this long discussion is a case study into his remarkable investment in Carvana. Cliff is one of the biggest investors in the business, which had a market cap over $60 billion in 2021, then fell 99%, survived, and now has a market cap approaching $50 billion again. While I hosted Carvana's CEO, Ernie Garcia, last year to get the inside perspective on managing through such turbulence, today we hear the investor's side of this extraordinary story. It is a singular episode and there are so many lessons in this rare opportunity to hear a major investor describe his decision-making process at every stage of the journey. Please enjoy my great conversation with Cliff Sosin.
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.
–
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 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.
-----
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
(00:05:32) Early Career and Discovering Investing
(00:06:49) Starting the Firm and Initial Challenges
(00:08:41) Investment Philosophy and Market Realities
(00:11:07) Building the Firm and Investor Relations
(00:12:23) Defining a Good Business
(00:17:31) Contained vs. Uncontained Businesses
(00:20:30) Mental Models and Market Insights
(00:35:13) The Role of ESG in Investing
(00:39:26) The Carvana Investment Story
(00:46:43) Carvana's Real Estate and Logistics Network
(00:49:12) Reconditioning and Selling Cars
(00:50:16) Carvana's Financing and Customer Service
(00:51:43) Economies of Scale and Trust
(00:54:40) Challenges and Management Insights
(01:04:07) Operational Issues and Market Challenges
(01:23:56) Questioning Carvana's Sales Strategy
(01:24:17) The Role of Word of Mouth in Carvana's Growth
(01:25:28) Identifying Early Adopters
(01:26:00) The Impact of Market Conditions on Carvana
(01:27:10) Carvana's Operational Challenges
(01:28:10) Cutting Costs and Organizational Efficiency
(01:32:19) The Apollo Deal and Debt Restructuring
(01:39:21) The Psychological Toll of Investment
(01:50:16) Future Investment Strategies and AI
(01:54:48)The US Market and Investment Opportunities
(01:59:51) The Kindest Thing Anyone Has Ever Done For Cliff
About Invest Like the Best with Patrick O'Shaughnessy
Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com
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