Bill Ackman: The Biggest Fight of His Life

Sep 29, 2026 Episode Page ↗
Overview

Bill Ackman, founder and CEO of Pershing Square Capital Management, discusses his investment philosophy, distinguishing innovation from hype, and the mistakes that reshaped his process. He also shares the deeply personal story of his daughter Lucy's brain hemorrhage and his plan to build a world-class brain institute.

At a Glance
13 Insights
1h 17m Duration
19 Topics
6 Concepts

Deep Dive Analysis

Daughter's Brain Hemorrhage and Recovery Journey

Founding a Brain Institute for Recovery and Longevity

Personal Coping Strategies and Managing Multiple Responsibilities

Building a Stable and Aligned Team at Pershing Square

Understanding Investment Bubbles and AI's Market Impact

Advice for Founders on Raising and Spending Capital

Distinguishing Public vs. Private Market Investing

AI's Influence on Investment Risk and Business Value

Pershing Square's Investment Process and Philosophy

Lessons Learned from Past Investment Mistakes

Evolution of Activism and Public Influence

Personal Use of AI for Medical Decision Support

Investing in Infrastructure and Experiential Assets

Transforming Howard Hughes into a Modern Berkshire Hathaway

Keys to Berkshire Hathaway's Enduring Success

Importance of Permanent Capital in Investment Management

Involvement with Bremont Watch Company

Recruiting CEOs and Judging Character

Public Misconceptions and Defining Personal Success

Arterial Venous Malformation (AVM)

A brain condition where arteries connect directly to veins, bypassing the capillaries, leading to excessive pressure that can cause a vein to burst and bleed into the brain.

Investment Bubble

A market phenomenon driven by human nature, FOMO, and abundant capital, where increasing money flows into a specific trade, leading to overvaluation until the bubble eventually bursts.

Super Durable Growth Companies

Businesses characterized by market dominance, high profitability, strong balance sheets, and the ability to consistently maintain or gain market share and pricing power over extended periods.

Asymmetric Bet

An investment strategy where the potential payoff is very large relative to the amount of capital put at risk, typically based on a contrarian view of macro events.

Permanent Capital Entity

An investment vehicle, such as a closed-end fund, where the capital remains invested even if shareholders sell their stock, enabling a long-term strategy and opportunistic buying during market downturns.

Modern-Day Berkshire Hathaway

A business model that leverages an insurance operation to generate 'float' (negative cost liabilities) and then invests that capital into common stocks and other businesses for high compounding returns, without significant stock dilution.

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What is an arterial venous malformation (AVM) and how does it cause brain hemorrhage?

An AVM is a brain structure where arteries connect directly to veins, bypassing capillaries, leading to excessive pressure that can cause a vein to burst and bleed into the brain.

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What is the typical medical response to a severe brain hemorrhage?

Doctors typically perform surgery to release pressure on the brain by removing a portion of the skull, but this is often not done if more than five hours have passed due to assumed brain death.

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How can wearable tech like an Oura Ring or Apple Watch potentially detect a medical emergency like a brain hemorrhage?

A sudden spike and drop in pulse combined with a fall detection alert could indicate a serious medical event, prompting an immediate alert.

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How does Bill Ackman manage multiple demanding roles and responsibilities?

He relies on a highly experienced and trusted team at Pershing Square, delegating operational tasks and focusing on strategic thinking, and structures his entities with independent boards.

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What defines an investment bubble?

A bubble occurs when human nature, FOMO, and abundant money lead to overvaluation in a particular trade or sector, eventually resulting in a burst.

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What advice does Bill Ackman give to founders raising capital in a hot market?

Raise capital now, but spend it judiciously, treating every dollar as your own, and don't assume that freely available capital will last forever.

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How does investing in venture-stage companies differ from public market investing for Pershing Square?

In venture, the investment is more a bet on the founder's ability to adapt and navigate challenges, as the original idea often changes, whereas public market investing focuses on established, dominant businesses.

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How does AI impact investment decisions and risk assessment?

AI significantly increases the risk of disruption for businesses, requiring investors to be extremely thoughtful about the durability of 'moats' and the long-term viability of companies.

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Why did Bill Ackman's firm stop short selling?

Short selling is inherently asymmetric in reverse, with finite upside and potentially infinite downside, and can lead to costly market dynamics and personal attacks.

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What is Bill Ackman's advice for ordinary people looking to invest?

Start young, invest consistently through dollar-cost averaging into index funds, and avoid holding cash while waiting for the market to drop.

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Why did Pershing Square initially sell Netflix and then buy it back?

They sold it when management's new information (ad model, subscriber miss) broke their original high-certainty thesis, then bought it back later when Netflix executed well on the new strategy and the stock price became attractive again.

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What is the core idea behind transforming Howard Hughes into a 'modern-day Berkshire Hathaway'?

The strategy is to leverage the cash flow generated from the self-liquidating real estate assets to build and invest in an insurance operation, using its 'float' to compound capital at a high rate, similar to Warren Buffett's model.

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What are the key elements of Berkshire Hathaway's success?

Key elements include permanent capital, a long-term view, control allowing for independent decision-making, talent for investing, and the ability to recruit strong management, all without significant stock dilution.

1. Prioritize Exercise for Focus

Engage in daily physical activity, such as tennis, to achieve complete focus and mental clarity, using it as a form of meditation to clear your mind from daily stressors.

2. Cultivate Long-Term Team Trust

Build a stable, transparent, and candid team over many years to foster deep trust, ensuring honest communication regarding risks and rewards in any venture.

3. Raise Capital Judiciously (Founders)

If raising capital in a hot market, do so, but spend it extremely carefully, treating every dollar as if it’s your own, and do not assume that easy money will last forever.

4. Invest in Super Durable Growth

Focus investments on dominant, highly profitable companies with strong balance sheets and a very low risk of disruption, aiming for long-term ownership that you’d be happy to hold for a decade.

5. Maintain Investment Checklist

Engrave investment principles on a ‘stone tablet’ or use a detailed checklist to ensure discipline, avoid common mistakes, and consistently adhere to core criteria for business quality and management.

6. Avoid Short Selling

Recognize that short selling presents an inverse asymmetry, where potential losses are infinite while gains are finite, making it a fundamentally risky and often ‘shitty business’.

7. Leverage AI for Medical Decisions

Utilize AI as a powerful research tool to vet medical decisions, especially for complex health incidents, and encourage medical professionals to check their work with AI for enhanced accuracy.

8. Start Investing Young with Index Funds

For ordinary investors, begin investing as early as possible with dollar-cost averaging into index funds for long-term market exposure, rather than attempting to time the market.

9. Adapt Investment Thesis to New Info

When new information emerges that is inconsistent with an original investment thesis, either significantly increase the position if the new information is immaterial or exit if the thesis is fundamentally broken.

10. Judge People Quickly and Holistically

When recruiting or evaluating individuals, assess for passion, capability, energy, honesty, and character, as these essential qualities can often be determined effectively within a short interaction.

11. Design Business for Permanent Capital

Structure investment vehicles with permanent capital (e.g., closed-end funds) to avoid forced liquidity decisions during market panics and enable opportunistic buying during downturns.

12. Focus on Nutrition in Recovery

Recognize the critical role of high-quality nutrition in brain and physical recovery, advocating for optimal food choices, especially in hospital or rehabilitation settings, as typical hospital food is often inadequate.

13. Maximize Social Interaction for Recovery

Emphasize the absolute criticality of socialization and emotional support for individuals recovering from severe brain injuries or other devastating health events, as it significantly aids recovery.

The thing that you need to think through is the risk of disruption. And what AI has done is massively increase the risk of disruptions.

Bill Ackman

The more time the brain is under pressure, the more damage that can take place.

Bill Ackman

I have this view that you, every bad thing, something good comes from it.

Bill Ackman

The power of Zoom. So I did, I would do a Zoom meeting for 45 minutes, and then I would go spend 15 minutes with my daughter.

Bill Ackman

The professionals breaking out right now aren't the most talented ones. They're the most visible ones. That's their edge.

AI Avatar (Shane Parrish)

I weight the person more than the idea because often the original idea is not the idea that turns out to be the success.

Bill Ackman

If you look at our most successful investments, they've usually been cases where we've done something that someone hasn't done before.

Bill Ackman

I never actually liked short selling because it's asymmetry in reverse, right? You can lose infinity and your amount you can make is finite.

Bill Ackman

You can actually influence the administration, the course of history with a tweet, which is pretty cool.

Bill Ackman

I think every doctor should actually be checking their work with, with, you know, Dr. Claude or pick your favorite website, favorite AI.

Bill Ackman

I think the key is to, one, start young. So the sooner you can start putting aside money that you can invest for the long term, the better for your retirement, you know, the power of compounding.

Bill Ackman

My definition has always been, I want to have the greatest, beneficent impact on the largest number of people.

Bill Ackman

Pershing Square Investment Process

Bill Ackman
  1. Identify potential 'super durable growth companies' from a long-followed library of businesses.
  2. Two team members conduct a deep dive, starting with SEC filings (10Ks, 10Qs) and conference call transcripts.
  3. Assemble key issues and questions to fully understand the business.
  4. Utilize expert networks to speak with former employees, industry experts, and competitors to gather insights.
  5. Build a financial model to assess the business and potential returns at current prices.
  6. The two-person team creates a presentation deck for the full investment group.
  7. The full investment team, including Bill Ackman and CIO Ryan, discusses the investment, with Ackman and Ryan also conducting independent assessments.
  8. Decide to make an investment or identify any remaining open issues for further research.
  9. If open issues are identified, the team goes back to do more work and reconvenes for further discussion.
5 hours
Typical maximum time for brain hemorrhage surgery to save someone Beyond this, brain death is often assumed.
19 hours
Duration of pressure on Lucy's brain before surgery Significantly longer than typical surgical window.
40%
Percentage of skull removed for brain pressure release To allow the brain to expand beyond the skull.
3.4 acres
Size of the site for the brain institute Located on 65th and 11th Avenue in New York.
2
Number of IPOs Bill Ackman did from his daughter's hospital room Two Pershing IPOs from room 1107 at Mount Sinai Hospital.
August 8th
Date Lucy was moved out of the hospital After extensive hospital care.
9:00 AM
Approximate time of unusual pulse spike on Oura Ring data Indicated a potential medical event for Lucy.
9 years
Duration the core investment team at Pershing Square has been together With a couple of new additions, showing low turnover.
45%
Bill Ackman's ownership stake in Pershing Square Part of the alignment structure.
35%
Investment team's ownership stake in Pershing Square Contributes to strong alignment within the firm.
8
Number of Bremont watches Bill Ackman bought for gifts After discovering the brand in London.
47%
Pershing Square's ownership stake in Howard Hughes Allows for a long-term, controlling view.
$4 billion
Value of condominiums under contract in Hawaii (Howard Hughes) In the process of being delivered.
$300 million
Annual net operating income from Howard Hughes' real estate assets Historically reinvested in real estate.
$300 million
Additional capital put into Vantage Holdings since acquisition To build the insurance operation.
70% real estate, 30% insurance
Current capital allocation of Howard Hughes By capital.
70-75% insurance, 25% real estate
Target capital allocation of Howard Hughes in 5 years Aims to accelerate transformation from real estate to insurance holding company.
28%
Employee ownership of Pershing Square Holdings Part of the permanent capital structure.
$500+ million
Employee investment in Pershing Square USA Demonstrates internal commitment to the entity.
60
Bill Ackman's age at his birthday in May A moment of reflection on life and impact.
106
Age Bill Ackman's grandmother lived to Despite smoking and drinking.