
Invest Like the Best with Patrick O'Shaughnessy
Hosted by Patrick O'Shaughnessy
Written by a model from the transcript; not yet reviewed.
Patrick O'Shaughnessy is joined by Alan Waxman, founder and leader of Sixth Street, for a detailed historical examination of the guardrails, incentives, and market structures shaping the modern financial system. Waxman traces the evolution of finance through three distinct systems, beginning with the 1933 Glass-Steagall Act up to the post-Global Financial Crisis era governed by Basel III and Dodd-Frank. They analyze the recent rise of private capital, the dangers of asset-liability mismatches, and the behavioral shifts driven by the factory model of investing. The conversation also covers the impacts of creative destruction and artificial intelligence across industries, alongside practical systems for personal organization, team development, and leadership.
The episode opens with sponsor advertisements for Ramp, Rogo, and WorkOS, followed by the host’s welcome and episode overview.
Patrick introduces Alan Waxman, founder of Six Street, and outlines the historical framework of financial systems—System One, Two, and Three—spanning from 1933 to the present.
The discussion covers the deregulation of 1999, the rise of leveraged banks, and the buildup to the 2008 crisis, highlighting the role of asset‑liability mismatches and leverage.
Waxman describes the transition to narrow strategies, the proliferation of single‑strategy vehicles, and the impact of COVID‑19 on capital deployment and risk appetite.
Waxman details the regulatory changes after 2010, the creation of Basel III and Dodd‑Frank, and how these reforms shaped the modern private‑capital landscape.
Waxman proposes principles for responsible private‑capital investing, emphasizing matched liabilities, prudent underwriting, and clear purpose.
The discussion turns to the role of AI and software as catalysts for change, exploring opportunities and risks across industries.
Waxman shares insights on building a resilient, learning‑oriented team at Sixth Street, highlighting the importance of adaptability in a fast‑changing environment.
The host explains his dual‑sheet method for left‑brain priorities and right‑brain creative ideas, and how he revisits them annually.
He discusses revisiting 25 years of right‑brain notes to find relevant insights and align them with current goals.
The conversation turns to the firm’s practice of having every employee create a personal business plan to clarify priorities.
They explore how different age ranges (20‑30, 30‑40, 40‑50, 50‑60) shape learning, ambition, and mentorship.
Three Eras of Financial Regulationinsight
Alan Waxman outlines the historical framework of the American financial system by dividing it into three systems, starting with the 1933 Glass-Steagall Act.
Glass-Steagall and The Wild Westdata
Before the 1929 crash and subsequent 1933 legislation, the financial system operated without strict guardrails, leading to 9,000 bank failures.
Repeal of Glass-Steagall in 1999story
Global competition from European banks uniting commercial and investment banking activities drove the repeal of Glass-Steagall in 1999.
Basel III and Post-GFC Guardrailsstrategy
Passed by G20 nations in 2010, Basel III imposed strict capital and liquidity restrictions on commercial banks to prevent excessive leverage.
The Factory Model of Investinginsight
The factory model drives firms to industrialize fundraising first, which forces them to lower underwriting standards and accelerate deployment.
Fee-Related Earnings Multiplesdata
Fee-related earnings multiples for asset managers expanded from 10 to 15 times in the early 2010s to over 25 to 30 times recently.
The Brain Personal Organization Systemstrategy
Alan Waxman explains his paper-based system of tracking strategic priorities, health goals, and contacts to maximize the return on time.
Facing the Tiger Ethosinsight
Sixth Street applies a core ethos of running directly toward difficult problems and market disruptions rather than avoiding them.
“The reason all this history is interesting to me is that ultimately, it's about the incentives and the ways that investors and investing firms make money.”
“If you are going to raise a narrow strategy, just direct lending or just private equity, you need to govern the amount of inflows that come in.”
“When those problems happen, instead of pointing fingers, we have just a saying from day one of our firm is that we look at the problems head on.”
“I think the biggest thing when you look at the human being is human beings in general don't change.”
“I have a lot of Hawaiian friends, your hui. The hui is the term for your group, your posse, having those experiences of climbing up the mountain together.”
My guest today is Alan Waxman, co-founder and CEO of Sixth Street, a $130B global investment firm. Private credit is one of the most discussed topics in markets right now, and there is a lot to make sense of. The current discourse is almost entirely focused on symptoms. Alan Waxman has spent the time diagnosing the root cause. Alan thinks about the financial system the way a historian would, studying the incentives, guardrails, and market structure that determine how things play out. In this conversation, he traces the evolution of American finance from the 1929 crash through Glass-Steagall, the GFC, and Basel III to explain how we arrived at what he calls the factory model, the industrialization of liability-gathering and asset deployment that he believes is the root cause of everything happening in private markets today. This is my second conversation with Alan, our first one is one of my favorites from last year. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- 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 Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. ----- 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. Visit WorkOS.com to transform your application into an enterprise-ready solution in minutes, not months. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- 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. Visit ridgelineapps.com. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Timestamps (00:00:00) Welcome to Invest Like The Best (00:02:43) Intro: Alan Waxman (00:04:35) Financial System Guardrails & Incentives (00:05:56) System 1: Pre-1933 to 1999 (00:07:39) Glass-Steagall Legislation (00:10:46) Deregulation & Rise of System 2 (00:12:27) Leverage, GFC, and System 2's Collapse (00:14:25) Basel III, Dodd-Frank, and System 3 (00:15:32) Why System 3 Could Be the Best Ever (00:19:04) Behavioral Shifts Starting in 2018 (00:19:52) The Factory Model (00:24:33) Acceleration of Factory Model (00:28:25) FRE Multiples and GP Incentives (00:34:59) Wealth Channel & Asset-Liability Mismatches (00:36:15) Why This Won’t be the Next GFC (00:45:31) AI, Creative Destruction & Opportunity (00:49:35) Alan’s One-Sheet Brain System (00:55:01) Lessons by Decade: Hui (00:59:28) Face the Tiger
11,724 words · 3 speakers
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