DiscoverInvest Like the Best with Patrick O'ShaughnessyAlan Waxman - Building Sixth Street - [Invest Like the Best, EP.433]
Alan Waxman - Building Sixth Street - [Invest Like the Best, EP.433]

Alan Waxman - Building Sixth Street - [Invest Like the Best, EP.433]

Update: 2025-07-153
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This podcast features Alan Waxman, co-founder and CEO of Sixth Street, a firm with a unique multi-strategy investment approach and significant assets under management. Waxman details his Goldman Sachs experience, emphasizing critical thinking and risk-reward analysis. He explains Sixth Street's framework for quantifying risk and return, considering business quality, capital structure, and market conditions. The firm's culture prioritizes collaboration, hiring "nice people who are over themselves," and fostering a respectful work environment. Waxman discusses successful investments like Spotify and Airbnb, highlighting the firm's adaptability and bespoke solutions. He explains Sixth Street's unique capital structure, "Tao," allowing for large investments while maintaining smaller fund sizes. The discussion also covers the development of investment themes, time allocation, the growth of private markets, and the importance of mentorship and talent development. Waxman emphasizes the "one-life principle," curiosity, and proactively addressing challenges ("facing the tiger"). He also highlights overlooked risks, including AI's impact on the job market and responsible wealth management. Finally, he discusses Six Three's vision, emphasizing long-term investment and a strong, positive culture, using annual offsites and hypothetical future visits to assess its enduring values. The podcast underscores the importance of a collaborative business model, efficient time management ("future self" concept), and a high return on time investment (ROTI).

Outlines

00:00:00
Introduction to Sixth Street's Investment Philosophy

The episode introduces the concept of "life's work" in investing and the importance of finding "maniacs on a mission." It introduces Alan Waxman and Sixth Street, highlighting their unique investment approach and substantial assets under management. The discussion also touches upon Ramp, a financial operations streamlining platform.

00:03:40
Alan Waxman's Career and Sixth Street's Approach to Risk and Return

Waxman recounts his Goldman Sachs experience and details Sixth Street's framework for quantifying risk and return, considering factors like business quality, capital structure, and market conditions.

00:13:43
Sixth Street's Culture, Recruiting, and Key Investments

Waxman discusses Sixth Street's recruiting process, culture, and proudest investments, including reflections on the 2008 financial crisis. He shares stories behind investments in Spotify and Airbnb.

00:37:38
Sixth Street's Capital Structure and Investment Strategies

Waxman explains Sixth Street's unique capital structure, "Tao," and the process of developing investment themes, emphasizing primary research, relationships, and cross-platform collaboration. He also discusses investments in sports and live entertainment.

00:52:04
Firm Management, Private Markets, and the Future of Investing

Waxman discusses time allocation, firm management, the growth of private markets, and the increasing competition for top GPs.

01:01:25
Mentorship, Talent Development, and Overlooked Risks

Waxman discusses his mentors, sources of inspiration, talent development, and overlooked risks, including the impact of AI and responsible wealth management.

01:09:40
Six Three's Culture, Vision, and Long-Term Approach

The speaker discusses Six Three's collaborative business model, the "future self" concept, time optimization, and their vision for long-term investment and a strong, positive culture. They detail methods for maintaining this culture.

Keywords

Life's Work


A deeply fulfilling and personally meaningful career pursued with intense dedication.

Maniacs on a Mission


Individuals intensely focused on achieving a specific goal with relentless drive.

Unitizing Risk and Return


A framework for evaluating investments by quantifying risk and return across different factors.

Multi-strategy Investing


An investment approach diversifying across various asset classes and strategies.

Face-to-Tiger Philosophy


Proactively engaging with challenges and refusing to shy away from difficult situations.

Bespoke Investment Solutions


Tailored investment strategies designed to meet specific client needs.

Private Alternatives


Investment options outside of traditional public markets.

Holistic View of Workplace Culture


A management approach considering employee well-being and collaboration.

Future Self Planning


Proactive planning for long-term goals, considering future needs and aspirations.

Return on Time Investment (ROTI)


Maximizing the value derived from time spent on activities.

Q&A

  • What is the core investment philosophy of Sixth Street?

    Sixth Street prioritizes a multi-strategy approach, focusing on unitizing risk and return across various asset classes and adapting to changing market conditions.

  • How does Sixth Street's unique capital structure, "Tao," contribute to its success?

    Tao allows Sixth Street to write large checks while maintaining smaller, opportunity-sized funds, combining scale with agility.

  • What are key elements of Sixth Street's culture?

    Sixth Street emphasizes a collaborative, values-driven culture prioritizing teamwork and a willingness to face challenges.

  • How does Sixth Street approach talent development?

    Sixth Street uses a demanding yet supportive approach, employing personal business plans and mentorship.

  • What are some overlooked risks in the current investment landscape?

    Waxman highlights the potential impact of AI-driven productivity gains on employment and the need for responsible capital allocation in wealth management.

  • How does Six Three's business model differ from others?

    Six Three prioritizes long-term investment and a strong, collaborative culture, emphasizing teamwork and respect.

  • What is the significance of the "future self" concept?

    The "future self" concept guided career choices, prioritizing efficient time management to maximize future family time.

  • How does Six Three maintain its positive culture?

    Six Three uses annual offsites and hypothetical future visits to assess and maintain its collaborative and positive culture.

Show Notes

My guest today is Alan Waxman. Alan is the co-founder and CEO of Sixth Street, one of the most unique investment firms with a "go anywhere, do anything" mandate across asset classes, geographies, and time horizons, and over $110 billion in AUM. He describes his journey from CIO of Goldman Sachs’ Special Situations Group and the frameworks he brought with him to lay the foundation for Sixth Street. Alan details their famous investments like Spotify and Airbnb during challenging periods, their innovative sports partnerships with Real Madrid and FC Barcelona, and their $30 billion "TAO" vehicle that allows them to write billion-dollar checks while keeping individual fund sizes matched to opportunities. We discuss hiring people without egos, enabling a truly multi-strategy approach, and Sixth Street’s "face the tiger" philosophy. Please enjoy this great conversation with Alan Waxman. 




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.


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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


(00:04:57 ) Introducing Alan Waxman and Sixth Street


(00:05:58 ) The Formative Goldman Sachs Years


(00:10:21 ) Unitizing Risk and Return


(00:14:23 ) Facing the Tiger: Sixth Street's Culture and Values


(00:34:51 ) Spotify and Airbnb: Case Studies in Investment


(00:39:20 ) Ambitious Investment Strategies


(00:40:40 ) Strategic Partnerships in Sports


(00:41:23 ) Navigating COVID with Airbnb


(00:43:36 ) Risk and Return Analysis


(00:46:56 ) Investing in Sports and Live Entertainment


(00:52:23 ) Developing Investment Themes


(00:55:29 ) Balancing Leadership and Investment


(00:57:30 ) The Importance of Culture


(01:10:33 ) Future Self and Long-Term Vision


(01:15:09 ) The Kindest Thing Anyone Has Ever Done For Alan

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Alan Waxman - Building Sixth Street - [Invest Like the Best, EP.433]

Alan Waxman - Building Sixth Street - [Invest Like the Best, EP.433]

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