Robert Robotti, President and CIO of Robotti & Company Advisors, joins host Michael Mauboussin to explore a lifetime shaped by value investing. With deep roots in accounting and formative experiences auditing firms like Tweedy, Browne, Bob shares how those early exposures led him to a career buying underfollowed, undervalued companies. In this episode, Bob discusses how his contrarian approach has thrived amid market inefficiencies, especially in cyclical industries and under-the-radar public firms. He breaks down key investments, including Builders FirstSource and Tidewater, and explains why capital allocation, aligned incentives, and patience are critical to long-term success. He also addresses private equity, passive investing, and how AI might affect the future of both business operations and markets — and much more!

Key Topics:

• Introduction (0:00)

• Bob's upbringing and early exposure to entrepreneurship (2:09)

• How auditing Tweedy, Browne sparked Bob's interest in value investing (4:17)

• Learning through Tony Pustorino and practical accounting (4:32)

• Early influences from Walter Schloss, Joe Reilly, and Tweedy, Browne (5:39)

• Experience working with Mario Gabelli (6:57)

• Founding Robotti & Company and the original value edge (8:54)

• Explaining pink sheet stocks and early investment strategies (10:00)

• Philosophy on intrinsic value and discounted investments (14:31)

• Mispricings from passive investing and cyclical businesses (16:24)

• Views on private equity vs. public markets (19:27)

• Being a generalist with deep knowledge in housing and energy (21:45)

• Simplified valuation approach and the Builders FirstSource case (23:41)

• Portfolio construction, sizing, and turnover explained (28:58)

• Maintaining a patient capital base (33:38)

• The Tidewater investment: thesis, board involvement, and strategy (36:42)

• Capital allocation philosophy: buybacks vs. dividends (49:08)

• Executive incentives and importance of management quality (51:02)

• How Robotti sees AI impacting business and investing (53:13)

• Thoughts on traditional business education and tangible assets (57:13)

• Geopolitical risks, China's influence, and global economic concerns (58:03)

• And much more!

Mentioned in this Episode:

• Robotti & Company Advisors

• Tweedy, Browne

• Gabelli & Company

• Builders FirstSource

• Tidewater Inc.

• Amrep Corporation

• Pulse Seismic Inc.

• Museum of American Finance

• U.S. Securities and Exchange Commission (SEC)

• Lucadia National

• Third Avenue Value

• Canadian Natural Resources

• Think Again by Adam Grant

• Grit by Angela Duckworth

• Teaming by Amy Edmondson

• Quit by Annie Duke

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In this episode, host Tano Santos sits down with Richard Brekka, founder and managing partner of Second Alpha, to examine the lesser-known world of secondary investing in private technology companies. With decades of experience—from venture capital to secondary transactions—Richard shares his journey through private equity at Chase and CIBC, his role in building and reviving companies like Gomez Inc., and how that led him to identify a unique investment niche. He explains the mechanics of sourcing deals in illiquid markets, using data and AI to surface hidden gems, and the psychology of getting deals done. The discussion also explores valuations, exits, and policy implications of private market access for 401(k) investors, plus the impact of AI on business fundamentals and much more!

Key Topics:

● Richard's early exposure to entrepreneurship and finance (3:29)

● Lessons from Arthur Laffer and University of Chicago MBA experience (6:15)

● Early career in private equity at Chase and learning value investing (8:12)

● Starting Dolphin Equity Partners after CIBC and early challenges (14:06)

● The rise and fall—and rebirth—of Gomez Inc. (17:18)

● Discovering secondary investing through Gomez's cap table (23:58)

● The founding and investment strategy of Second Alpha (26:29)

● Understanding the structure and dynamics of the secondary market (30:21)

● How Second Alpha sources deals and builds its data pipeline (35:49)

● The process of deal execution and managing rights of refusal (41:11)

● Case study: Prove Identity and growth through secondaries (52:29)

● Thoughts on liquidity, valuation, and 401(k) access to private markets (55:35)

● AI's impact on private companies and investment strategies (59:19)

● Book and podcast recommendations (1:01:34)

● And much more!

Mentioned in this Episode:

● Second Alpha

● Chase

● CIBC

● Gomez Inc.

● Prove Identity

● TouchCommerce

● Arthur Laffer

● Acquired (podcast)

● Warren Buffett – Berkshire Hathaway Annual Letters

● Berkshire Hathaway Annual Shareholder Letters

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Amit Wadhwaney, founding partner and portfolio manager at Moerus Capital Management, joins hosts Tano Santos and Michael Mauboussin to trace his unorthodox journey from Bombay to Concordia to founding a value investing firm focused on the balance sheet. Along the way, he discusses his early exposure to Marty Whitman, lessons from Third Avenue's international expansion, and what led him to start Moerus.

Amit outlines the core of his investment approach—asset-based valuation, downside protection, and long-term holding periods—and explains why macro factors are typically disqualifiers, not drivers, in his process. He shares insights into portfolio construction, the role of currency risk, and how Moerus identified undervalued opportunities in places like Argentina, Japan, and the gold sector.

Key Topics:

● Growing up in India and finding investing through chemical engineering and economics (3:04)

● Discovering Marty Whitman via an obscure academic book on value investing (5:05)

● Lessons from selling real estate during Quebec's post-referendum panic (9:23)

● Joining MJ Whitman and watching Third Avenue evolve (11:12)

● Pioneering international value investing at Third Avenue (17:05)

● Founding Moerus Capital: philosophy, culture, and investment constraints (24:38)

● Moerus's asset-based investment framework (28:48)

● Managing macro risk and volatility through conservatism, not forecasts (30:41)

● Risk management: internal, external, and business model-related risks (33:00)

● Portfolio construction, position sizing, and concentration limits (46:39)

● Currency exposure and when to hedge (49:12)

● Case studies: Grupo Galicia and Despegar during Argentina's political shift (51:15)

● What keeps Amit up at night: industrial policy, broken immigration, and political gridlock (1:00:52)

● What Amit is reading—and what the Norton Simon Museum can teach investors (1:03:39)

● And much more!

Mentioned in this Episode:

● Moerus Capital Management

● Third Avenue Management

● MJ Whitman

● Marty Whitman

● Grupo Financiero Galicia

● Despegar.com

● Wheaton Precious Metals

● Major Drilling Group

● Dundee Corporation

● UniCredit

● LATAM Airlines

● Journal of Economic Literature

● Shubik and Whitman's The Aggressive Conservative Investor

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Bill Ackman, founder and CEO of Pershing Square Capital Management, joins hosts Michael Mauboussin and Tano Santos to trace the arc of his investing journey—from his early days in real estate finance to founding Gotham Partners and eventually building Pershing Square into a $30 billion firm. Bill discusses formative moments that shaped his thinking, including his controversial early short of MBIA, the painful lessons of the Valeant episode, and the transformation brought about by adopting a permanent capital structure. He also unpacks his investment philosophy, the importance of durability and moats, and his team's approach to risk, activism, and concentrated investing. Along the way, Bill offers thoughts on AI, higher education, and what excites—and concerns—him about the future — and much more!

Key Topics:

● Bill's near-death experience and early independence (2:19)

● Skills learned at Harvard and lessons from rowing and sales (3:50)

● Real estate foundation and Gotham Partners launch (6:44)

● Early credit derivative bet and discovery of MBIA issues (12:23)

● Formation and lessons from Pershing Square (19:02)

● The three eras of Pershing Square and the importance of permanent capital (21:03)

● Bill's investment philosophy and focus on durable moats (27:31)

● Thoughts on capital-light, network-effect businesses (33:58)

● How Pershing Square handles portfolio concentration and risk (36:30)

● Impact of AI and the resilience of activist investing (40:17)

● Student pitch trends and what makes a strong investment case (43:25)

● What Pershing looks for when hiring investment professionals (47:29)

● What worries and excites Bill today (51:34)

● Recommended reading and X as a research tool (54:34)

● And much more!

Mentioned in this Episode:

● Pershing Square Capital Management

● Gotham Partners

● MBIA Inc.

● Farmer Mac

● Herbalife

● Valeant Pharmaceuticals

● General Growth Properties

● Hilton Worldwide

● Uber Technologies

● Universal Music Group

● Brookfield Asset Management

● The Financial History of Berkshire Hathaway by Adam Mead

● The Compounders: Lessons from 50+ Stories of Business Growth by Travis Wiedower

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In this episode, hosts Tano Santos and Michael Mauboussin speak with Kristin Gilbertson, CIO of Access Industries and former CIO of the University of Pennsylvania Endowment. Kristin shares her early interest in economic development and her unique journey through the World Bank, Stanford Management Company, and into managing a major university endowment. She outlines how risk awareness and preparation helped her successfully lead through the 2008 financial crisis and gives detailed insights into asset allocation, manager selection, and the nuances of family office investing. Kristin also discusses career strategies for students interested in the endowment and wealth management space and much more!

Key Topics:

● Kristin's early life and interest in economics (3:33)

● Influential professors and academic inspirations at Harvard (4:10)

● Experience at the World Bank and the Young Professionals Program (10:09)

● Joining Stanford Management Company and portfolio repositioning (15:05)

● Moving to Penn and addressing portfolio gaps and alumni engagement (18:26)

● The responsibilities and structure of a university CIO role (22:00)

● Building Penn's VC exposure and getting into Sequoia (26:20)

● Kristin's investment philosophy and fixed asset allocations (34:34)

● Kristin's role at Access Industries and managing a family office (38:16)

● Differences between endowments and family offices (41:10)

● Concerns about mega-cap stock valuations and ETF opportunities (46:34)

● And much more!

Mentioned in this Episode:

● Pioneering Portfolio Management by David Swensen

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In this episode, host Michael Mauboussin sits down with Seth Klarman, CEO and portfolio manager of The Baupost Group. One of the most influential practitioners of value investing, Seth shares his formative stories — from arbitraging coins as a kid to launching Baupost in 1982 — and reflects on his decades-long investment philosophy. They explore timeless principles of market inefficiencies, the importance of temperament, specialization versus generalization, the role of patient capital, and the challenges and opportunities ahead for investors in today's world. Seth also opens up about technology trends like AI, the evolving market structure, and the enduring lessons from Graham & Dodd — and much more!

Key Topics:

• Seth's early entrepreneurial ventures and coin arbitrage (2:10)
• Lessons from working at Mutual Shares with Max Heine and Michael Price (4:12)
• Starting Baupost and managing the founding families' wealth (10:53)
• Core principles behind value investing and market inefficiencies (13:06)
• The impact of indexing, ETFs, and passive investing trends (16:42)
• Generalists vs. specialists in investment research (19:06)
• How Baupost evaluates opportunities across asset classes (21:13)
• Why value investing combines a contrarian streak with a calculator (23:51)
• The importance of meeting management teams and assessing intent (26:44)
• Building and educating a long-term oriented client base (29:06)
• Managing behavioral biases and fostering the right temperament (31:21)
• Current market outlook and where Baupost sees value today (34:03)
• How AI is changing research and efficiency at Baupost (36:54)
• Broader applications of the "Moneyball" mindset (40:13)
• The difference between an analyst and a portfolio manager (44:01)
• Seth's views on risk, business ethics, and business education (45:50)
• What worries Seth about the future — and what excites him (48:11)
• Book recommendations from Seth Klarman (51:42)
• And much more!

Mentioned in this Episode:

• Margin of Safety by Seth Klarman
• Security Analysis by Benjamin Graham & David Dodd (Seventh Edition)
• Moneyball by Michael Lewis
• Lost & Found by Kathryn Schulz
• Being Wrong by Kathryn Schulz
• The Light Eaters by Zoë Schlanger

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In this episode of Value Investing with Legends, Tano Santos and Michael Mauboussin sit down with Kent Daniel, Professor of Finance at Columbia Business School, to discuss his journey from physics at Caltech to leading research in behavioral finance and quantitative investing. Kent shares insights from his academic work and his years at Goldman Sachs, including his critiques of the Fama-French model, the role of intangible information in asset prices, and the implications of short selling constraints. The conversation spans decades of market evolution, empirical challenges, and the behavioral patterns that continue to shape financial theory and practice.

Key Topics:

● Introduction by Tano Santos and Michael Mauboussin (0:00)

● Introduction of guest Kent Daniel and his academic and professional background (0:48)

● Kent shares his early life, education at Caltech, and influences like Richard Feynman (3:31)

● Transition from physics to finance, MBA at UCLA, and entry into PhD program (5:46)

● Kent's dissertation on time variation in asset returns and statistical test power (8:02)

● Discussion on behavioral vs. rational explanations for return predictability (11:51)

● Kent's time at University of Chicago during the rise of behavioral finance (15:18)

● Challenge to the Fama-French three-factor model with characteristics vs. covariances paper (22:40)

● Behavioral finance classic: Overreaction and underreaction explained through psychology (27:31)

● Discussion on tangible vs. intangible information in financial markets (36:04)

● Current research on short selling, borrow costs, and market inefficiencies (41:40)

● Kent's experience at Goldman Sachs and practical application of academic research (50:02)

● Reflections on the quant crisis and build-up of leverage pre-2008 (56:26)

● Discussion on value investing post-2008 and limitations of book-to-market (57:00)

● Kent's nuanced view on market efficiency and the role of frictions (1:02:16)

● Views on indexing, ETFs, and financial market design (1:06:11)

● Kent shares what excites and worries him about the future of markets (1:08:09)

● Kent's current reading and listening recommendations (1:10:07) And much more!

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In this episode, Cliff Asness joins Tano Santos and Michael Mauboussin for a conversation that spans the evolution of quantitative investing, lessons from market crises, and the enduring tension between risk and behavioral explanations in finance. From his formative years at the University of Chicago under Gene Fama to building AQR into a quant powerhouse, Cliff reflects candidly on theory, performance, and how markets may have become less efficient in recent years.

Key Topics:

• Tano and Michael return from sabbatical and reflect on recent academic and classroom experiences (0:00)
• Overview of Cliff's career and contributions to quant investing and academic finance (1:13)
• Cliff recounts his underachiever label, how standardized tests changed his path, and why he chose Penn's M&T program (2:54)
• How Cliff's coding work for Andy Lo inspired his academic path and led to Chicago (5:03)
• A breakdown of the 1992 and 1993 Fama-French papers, and how they reshaped asset pricing (8:45)
• Cliff discusses the theoretical divide between Fama and Thaler and his own evolution toward a behavioral perspective (13:08)
• Memories of presenting momentum to Fama, intellectual honesty, and voice-shaking dissertation defenses (17:13)
• Why Cliff chose Goldman over academia, his role in developing Goldman's quant group, and the influence of LTCM (22:00)
• Launching in August 1998 during the Russia default; early drawdowns and lessons from the tech bubble (27:50)
• How quant signals hold up, risks of crowding, and the difference between short-term and long-term capacity (34:32)
• Momentum held, but value strategies collapsed. How AQR dealt with long underperformance (43:31)
• Valuation starting points can obscure long-term performance; recent decades viewed in proper context (49:22)
• Cliff's provocative "Less Efficient Market Hypothesis" and three key drivers: indexing, interest rates, and social media (50:54)
• Is passive investing weakening price discovery? Reflections on Sharp's arithmetic and Grossman-Stiglitz (54:12)
• How echo chambers and meme stocks challenge traditional models of rational price formation (58:28)
• Why companies aren't issuing more equity despite sky-high valuations, and the fading role of smart capital allocators (1:00:46)And much more!

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In this episode, Michael Mauboussin, adjunct professor at Columbia Business School, hosts Phil Ruvinsky, Managing Director and Head of the Fundamental U.S. Growth Team at BlackRock. With extensive experience in the investment industry, Phil shares his journey from law to finance, discusses his investment philosophy, and explains the importance of sustainable competitive advantages. The conversation explores the evaluation of management, the impact of AI on the competitive landscape, and the nuances of portfolio construction. Phil also highlights the role of macroeconomic factors and regulatory changes in investment decisions, shares his thoughts on the future of active management in an increasingly indexed market, and much more!

Key Topics:

• Introduction to Phil's career and background (1:06)

• Transition from law to investment and early career challenges (2:15)

• Importance of business school in shaping investment philosophy (3:47)

• Recommended books for new team members (4:22)

• Utilizing competitive strategy analysis in investment decisions (5:50)

• Unique characteristics of technology, media, and telecom sectors (7:03)

• Analysis of return on invested capital in different business models (9:10)

• Approaches to valuation and use of different tools (10:25)

• Evaluating the importance of management in investment decisions (12:15)

• Impact of AI and generative AI on the competitive landscape (14:17)

• Application of AI in the investment process (18:07)

• Trends in market concentration and their implications (20:26)

• Effects of indexing and rules-based investing on markets (23:27)

• Corporate governance, capital allocation, and executive compensation (25:35)

• Differences between being an analyst and a portfolio manager (28:02)

• Portfolio construction and risk management (29:38)

• Considering macroeconomic factors in investment decisions (32:00)

• Concerns and excitement about the future (34:21)

• Phil's book recommendations (35:58)

• And much more!

Mentioned in this Episode:

• Digital Empires: The Global Battle to Regulate Technology by Anu Bradford

• Expectations Investing: Reading Stock Prices for Better Returns by Michael Mauboussin

• Competition Demystified: A Radically Simplified Approach to Business Strategy by Bruce Greenwald

• The Platform Delusion: Who Wins and Who Loses in the Age of Tech Titans by Jonathan Nee

• Napoleon Unleashed: A History of the Revolutionary, Emperor, and Military Genius who Reshaped Europe and Defined Modern Leadership by Aeon History

• Meditations by Marcus Aurelius

• Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts by Annie Duke

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In this episode, hosts Tano Santos and Michael Mauboussin speak with Anu Bradford, the Henry L. Moses Professor of Law and International Organization at Columbia Law School, to discuss the intricate dynamics of global technology regulation. Anu is recognized for her deep expertise in international economic law. Her pivotal books "The Brussels Effect" and "Digital Empires" explore how significant regions like the US, EU, and China shape technological standards worldwide. The conversation probes the complexities of regulating big tech companies across different legal and political landscapes, highlighting the significant influence of European regulations on global markets. She also touches on the impact of regulatory practices on innovation, the challenges of enforcing extensive digital laws, and the future trajectory of global tech governance. This episode offers a comprehensive look into the power struggles and cooperative efforts that define international technology regulation and much more!

Key Topics:

• Introduction to Anu Bradford and her background (04:01)
• The unique position of the EU in global regulatory practices and its impacts (10:48)
• Detailed exploration of "The Brussels Effect" and its significance (12:56)
• Global market influence through regulatory strategies (17:02)
• The challenges and methodologies of tech regulation in the EU, US, and China (31:55)
• The role of data security and privacy in international relations and tech regulation (43:06)
• Future challenges and directions in global technology regulation (52:47)
• The preservation of liberal democracy in the digital age (54:51)
• Anu's book recommendations (58:56)
• And much more!

Mentioned in this Episode:

• Digital Empires: The Global Battle to Regulate Technology by Anu Bradford
• The Brussels Effect: How the European Union Rules the World by Anu Bradford
• Chip War: The Quest to Dominate the World's Most Critical Technology by Chris Miller
• Underground Empire: How America Weaponized the World Economy by Henry Farrell and Abraham Newman
• High Wire: How China Regulates Big Tech and Governs Its Economy by Angela Huyue Zhang

Thanks for Listening!

Be sure to subscribe on Apple, Google, Spotify, or wherever you get your podcasts. And feel free to drop us a line at [email protected].

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