Summary

Ackman sees AI as a genuinely transformational technology wrapped in unmistakable bubble behavior. He cites the same startup raising $50 million at a $400 million valuation and, two weeks later, another $50 million at $1 billion; another raised a Series A at a $5 billion valuation. Founders should raise while capital is abundant but “treat every dollar as if it were your own money,” because a loud reset will come and “people will lose a lot of money.”
AI has raised the probability that apparently dominant businesses simply disappear, making moat analysis harder than at any point in Ackman’s career. Investors valuing 10, 20, or 30 years of cash flows must now imagine disruption that even Warren Buffett missed during the internet transition. AI may dramatically lower incumbents’ costs—Ackman says Cognition can modernize banks’ COBOL systems in days rather than months—but whether shareholders retain those savings depends on pricing power.
Pershing Square distinguishes public-market durability from venture investing’s dependence on a singular founder. Public holdings should be dominant, highly profitable, strongly financed businesses whose management can be replaced if needed; early-stage companies are bets on people who can survive the failure of their original plan. Ackman disliked Bom Kim’s 2009 plan to build a Korean Groupon but backed Kim, who ultimately turned Coupang into what Ackman calls “the Amazon of South Korea.”
A billion-dollar position usually begins with years in Pershing Square’s “library” of researched companies. Two team members study filings, calls, competitors, former employees, experts, and valuation; Ackman and the wider team independently challenge the work before deciding. AI helps with research, but Ackman doubts it will originate the non-consensus trades that produced Pershing’s best outcomes: pandemic credit-default swaps, distressed equities, or pre-crisis protection on AAA credit.
Ackman is turning Howard Hughes from a discounted real-estate vehicle into a “modern Berkshire Hathaway” built around insurance and permanent capital. Pershing owns 47%; land sales, roughly $4 billion of contracted Hawaiian condominiums, and about $300 million of real-estate net operating income are intended to fund Vantage Holdings rather than further property accumulation. He says today’s roughly 70% real-estate/30% insurance mix may move to roughly 70–75% insurance within five years.
His daughter Lucy’s catastrophic brain hemorrhage redirected Ackman’s capital, relationships, and attention toward brain recovery. After roughly 19 hours of pressure on her brain and removal of about 40% of her skull, she recovered her cognition and humor while gradually relearning movement, speech, and vision. Ackman closed on a biotechnology building within 60 days and signed for remaining plots totaling 3.4 acres to build a patient-centered institute spanning rehabilitation, brain-computer interfaces, AI-assisted therapy, nutrition, and longevity: “I literally feel like I was created to help her.”
The recurring investment lesson is to preserve optionality and leave when confidence, not merely price, breaks. Pershing sold Netflix after management abruptly reversed its “never advertising” position, later rebuying only after the ad model, cash generation, and valuation improved; it abandoned short selling because the payoff is capped while losses and personal conflict are not. For ordinary savers, Ackman’s prescription is simpler: start young, compound through index funds unless willing to do serious company work, and do not sit indefinitely in cash because the market looks expensive.

Deep dive

1. Lucy’s near-fatal hemorrhage became a mission to reinvent brain recovery

Ackman describes Lucy as a healthy young woman with what doctors called an arteriovenous malformation: blood bypassed the capillary system, overloaded veins in her brain, and eventually caused one to rupture. She was found face down and barely breathing only after failing to collect luggage for a friend’s wedding; Ackman says wearable data suggested the event occurred around 9 a.m., and she endured roughly 19 hours of pressure before surgery.
Surgeons relieved the pressure by removing about 40% of her skull so the brain could expand. Ackman says he learned only weeks later that operations are generally not attempted after more than about five hours because brain death is presumed; the family initially did not know what the outcome would be.
His instruction to the medical team was a “dare to be great” speech: assume unlimited resources, examine the newest technologies, and discover everything potentially useful. Lucy recovered her cognition, personality, and sense of humor; walking is returning, she can produce roughly 15 of 17 vowel sounds and is learning consonants, while her vision has shown some progress.
Ackman moved his office to the hospital and conducted two IPOs from room 1107—45 minutes on Zoom, then 15 minutes with Lucy. Her mother’s daily presence and friends’ constant visits reinforced his conviction that social interaction is absolutely necessary for rehabilitation: “Everyone loves Lucy, and she gets an amazing return from this.”

2. The rehabilitation system stops paying long before recovery stops

Ackman’s indictment is fundamentally about incentives: neurosurgeons are paid to operate, not to oversee years of recovery, while insurance may cover only six weeks of rehabilitation. A Massachusetts General rehabilitation leader told him that an ordinary patient might never receive surgery—or might be discharged to a nursing home and die of pneumonia within months.
A first-rate speech therapist can cost $500 an hour, yet patients may improve for years. Ackman sees AI as a way to make persistent speech therapy broadly available, allowing the standard of care Lucy received through “financially unlimited” resources to reach people whose families cannot stop working to manage rehabilitation.
Within 60 days, Ackman closed on the vacant biotechnology building at the corner of 65th Street and Eleventh Avenue and signed a purchase contract for remaining plots totaling 3.4 acres. The planned Ackman-Oxman brain institute will focus on brain and physical recovery—“fundamentally longevity”—with clinical care, rehabilitation, technology, research, socialization, and nutrition designed around the patient.
He expects brain-computer interfaces, Neuralink and roughly a dozen other companies, better neural data, and AI interpretation to create new options. Ackman imagines glasses that act as cameras and transfer visual information to the visual cortex; he relays Elon’s claim that within five years people could have better eyesight than humans currently do. He presents this as hope for Lucy, not a capability available today.

3. Wearables could turn unexplained falls into actionable medical alarms

Ackman says Lucy’s Oura data showed an unusual pulse spike around 9 a.m., followed by an unusual drop. He proposes combining that pattern with a separately detected fall: if a sharp physiological change coincides with someone falling, a wearable should escalate rather than assume the person merely fell or became intoxicated.
The lost hours matter because brain damage increases while pressure remains untreated. Apple Watch already has a fall notification; Ackman says Oura should offer similar emergency functionality and believes the company is working on it.
His broader design brief extends even to hospital food. Serving pancakes, syrup, and orange juice after a heart attack epitomizes a fragmented system; the institute will treat food as “critically important,” alongside surgery, rehabilitation, technology, and long-duration follow-up.

4. Pershing Square’s culture is now an asset that operates without its founder doing everything

When Ackman founded Pershing Square, he generated the ideas, directed the analysis, and personally handled activism. Twenty-two years later, the investment team has remained unchanged for about nine years, with several new employees, creating what he calls a culture of “transparency and frankness” in an industry accustomed to lucrative employee turnover.
Ackman now generates a minority of portfolio ideas, though he retains an important vote; Ryan, whom Ackman identifies as the IT director, and the investment team carry much of the process, while Ben oversees many business functions. The structure gives Ackman time for strategic projects without requiring Pershing Square itself to depend on his daily presence.
Ownership reinforces the arrangement: Ackman says he owns about 45% of the management company and the team roughly 35%. He contrasts Pershing’s properly paid, focused directors with something he believes he read about conventional closed-end funds: six directors represented on as many as 86 boards. “It’s hard to do real management” at that scale.

5. AI’s venture boom has the classic anatomy of a bubble

Ackman defines a bubble as a human feedback loop: people make large profits, outsiders develop fear of missing out, and more capital chases the same trade until prices are reassessed and the bubble cracks. Railways, cars, transistors, and the internet all paired real technological change with speculative excess.
AI is “the most transformational technology” of his lifetime, yet private markets already show “crazy things.” The same company raised $50 million at a $400 million valuation and another $50 million at $1 billion two weeks later; he has also seen a company raise a Series A at a $5 billion valuation.
His advice to founders is to raise capital now without adopting the spending rate implied by abundance. During the internet bubble, Barron’s published a rundown of public internet companies’ remaining cash and burn-rate runway shortly before the market broke; when easy financing vanished, businesses needing another round within three months disappeared.

6. AI makes every long-duration investment thesis more fragile

Ackman’s valuation framework is the present value of lifetime cash flows, with the near years weighted most heavily. Anyone making an illiquid investment should be comfortable owning it if “the stock market closed for 10 years,” which requires predicting the business—not merely the product—10, 20, or 30 years forward.
AI has sharply increased the “risk of failure.” Ackman invokes Buffett’s inability to anticipate every internet-created disruption—Wikipedia destroying World Book—as a warning that today’s investors are “guaranteed to look foolish” on some holdings whose apparent moats prove narrower than expected.
Cognition illustrates the upside: Ackman says its software can rewrite banks’ legacy COBOL systems into modern code in days rather than months, materially reducing operating costs. The unresolved investor question is who captures the benefit; when every bank adopts similar tools, competition may pass savings to customers rather than expand shareholder margins.
The development cadence is itself destabilizing. Microsoft’s consequential 1.0-to-2.0 upgrades once took years; AI products can receive updates with significant consequences every few days, closer to a Tesla receiving important software overnight. That does not “scare” Ackman so much as force continual reconsideration of whether a company’s moat is genuinely wide.
Ackman also says AI helped him make medical decisions for Lucy and that every doctor should check their work with Claude or another preferred AI.

7. Infrastructure may win from AI even when application economics remain uncertain

Ackman calls Brookfield “incredibly well managed” across infrastructure, financing, and construction. Because demand for computing appears effectively endless, data centers and power provide a comparatively direct way to participate in AI’s buildout: Brookfield can supply a meaningful part of the physical “spine.”
He is more guarded about the barbell thesis that digital abundance makes live sports increasingly valuable. Games offer an intensely human experience to people otherwise sitting alone, but teams are priced “more like works of art than financial enterprises”; many do not earn money because owners may spend every dollar they are allowed to spend on expanding the franchise.
Asked whether he would buy a sports team, Ackman’s answer is simply “No.” The emotional scarcity may be real without satisfying his valuation discipline.

8. Venture success depends more on the founder than the original business plan

In public markets, Pershing wants dominant, highly profitable businesses with strong balance sheets, durable share, expansion potential, and pricing power. The CEO matters, but if management is inadequate, Pershing believes it can find a better successor.
Venture investing reverses that hierarchy. Pre-revenue or loss-making companies consume cash while searching for a model that can eventually fund itself, so the founder’s ability to change direction matters more than the plan presented at the first meeting: “Often the original idea is not the one that turns out to be successful.”
Ackman’s best example is Coupang. In 2009, Bom Kim proposed a Groupon-like business in South Korea—a model Ackman thought was terrible—but made a convincing case for Korean e-commerce and impressed him personally. Kim navigated the obstacles and built what Ackman describes as South Korea’s Amazon, largely unrelated to the original pitch.

9. A billion-dollar check starts with a library, a price, and institutionalized dissent

Pershing follows attractive businesses for years in a “library,” often completing the work before valuation permits ownership. A company trading around 35 times excess profit may not offer the targeted return above 20%, so the team waits for COVID, the “SaaS apocalypse,” or another dislocation; that software reset created an attractive entry into Microsoft.
Typically two team members begin with 10-Ks, 10-Qs, earnings-call transcripts, expert networks, former employees, competitors, and industry specialists. They build a model and identify unresolved questions; Ackman and roughly five teammates who did not conduct the original work then challenge the thesis before capital is committed.
AI currently serves mainly as a research tool, not a model builder. Since every investor can access similar systems, Ackman expects differentiation to remain in nonstandard thinking and synthesis—the creative leap behind buying pandemic credit-default swaps, investing in bankrupt equities, or selling protection against AAA credit before the financial crisis.

10. Pershing’s durable-growth strategy is paired with rare, asymmetric macro bets

Ackman attributes Pershing’s post-2010 resilience to continually raising its quality threshold rather than adhering mechanically to statistical value. The core remains “super-resilient growth,” but macro dislocations can produce exceptional returns when Pershing holds a differentiated view and finds an instrument with limited capital at risk.
The firm was about a week ahead of the consensus in anticipating a global COVID shutdown, then concluded that huge inflation would force interest rates higher. These were structured so the potential payoff greatly exceeded the amount committed.
Large losses around 2015 and 2016 prompted Ackman to engrave the principles on a metaphorical “stone tablet”: simple, predictable, free-cash-flow-generating businesses; large and liquid public companies; appropriate management; and a reluctance to short equities. The checklist exists because intellectual confidence alone had not prevented avoidable mistakes.
Short selling offers “asymmetry in the opposite direction”—limited gains and theoretically unlimited losses. Pershing made most of its money on the MBIA situation through credit-default swaps rather than short sales of shares. A later short in a company Ackman declines to name attracted Carl Icahn, squeeze dynamics, media attacks, and legal pressure; longs, by contrast, tend to create allies as everyone benefits together.

11. Netflix shows why a broken thesis matters more than recovering the loss

Netflix entered Pershing’s library after missing subscriber-growth expectations. Ackman considered it a dominant business, bought a substantial position, and found management aligned with Pershing’s analysis—including an emphatic assurance that Netflix would “never” introduce an advertising model.
Three or four weeks later, another subscriber miss left management visibly shocked, and it abruptly said advertising was necessary. Ackman’s rule was binary: if the new fact is immaterial, the lower price warrants buying much more; if it breaks the thesis, exit. The widening range of outcomes no longer met Pershing’s requirement for exceptionally high confidence.
Pershing sold, took the tax loss, and redeployed into Alphabet rather than insisting on winning the money back the same way. Netflix subsequently built a successful advertising business, generated more cash, and won the streaming war; after the valuation first became unattractive and later fell roughly by half, Pershing bought it again.

12. Howard Hughes is designed to convert land into an insurance compounding machine

Howard Hughes emerged from Pershing’s General Growth investment during the financial crisis. Pershing bought 25% after the shares had fallen 99%, to half a percent of their prior value, pushed for an unavoidable Chapter 11 restructuring, and separated unwanted land and master-planned communities; unusually, both General Growth and the spun-out Howard Hughes appreciated.
Ackman likens the master-planned communities to SimCity. In The Woodlands, a roughly 150,000-person community near Houston, Howard Hughes owns the residential and commercial land, sells residential parcels to builders, and develops the commercial assets a growing town requires; related holdings sit in Texas, Las Vegas, Hawaii, and Phoenix.
Pershing now owns 47%. Howard Hughes has about $4 billion of Hawaiian condominiums under contract and roughly $300 million in real-estate net operating income; instead of continuously recycling proceeds into more property, it will maintain the communities and direct the surplus toward Vantage Holdings, a property-and-casualty insurer.
The Berkshire analogy is specific: profit on underwriting creates a negative cost of capital, while Pershing manages the investable assets. Howard Hughes has already added $300 million of Vantage capital; Ackman says the mix may move from roughly 70% real estate today to 70–75% insurance within five years, while limiting dividends, options, and share issuance.

13. Permanent capital preserves the right to wait

Charlie Munger once told Ackman that Berkshire’s most underestimated advantage was that “circumstances almost never forced us to make a decision.” Ackman has built Pershing around the same option value: investors may sell publicly traded shares during a panic, but their sale does not withdraw capital from the underlying fund.
Employees own about 28% of Pershing Square Holdings, hold a similar direct-and-indirect interest in Howard Hughes, and invested roughly $500 million in Pershing Square USA. Those anchor positions align the organization while permanent structures let Pershing buy during crises instead of liquidating to meet redemptions.
Ackman says traditional hedge-fund capital leaves both when performance is poor and when it is excellent but an allocator becomes overexposed. Constant fundraising consumed his attention and contributed to Pershing’s largest investment mistake; abandoning redeemable capital means that merely approximating historic returns could, by his calculation, produce a trillion-dollar asset base in 20 years.

14. Judgment, humility, and time define Ackman’s endgame

Bremont is his cautionary counterexample. He discovered the watch by chance, invested as though it were a hobby, and admits he “did not do proper due diligence,” relying instead on his assessment of the founders’ character; an unsuccessful boutique expansion consumed capital before Ackman backed CEO David Serrato, bought effective control, and became non-executive chairman.
His preferred CEO-search method lowers execution risk: find someone who has already solved the problem, then conduct a 360-degree review with former colleagues and competitors. That process led Pershing to Brian Nikola during Chipotle’s food-safety crisis; Ackman looks for obsessive passion, ability, energy, honesty, and character, though he concedes his people judgment “hasn’t been perfect.”
For ordinary investors, the dividing line is effort. Anyone selecting businesses must devote real time to study and homework; everyone else can sensibly use index funds, which have beaten most active managers. Start young, harness compound returns, and do not remain in cash merely because the market appears expensive.
At 60, Ackman frames the remaining horizon as perhaps 20–25 healthy years, notwithstanding his grandmother living to almost 106 and his hope that AI and better drugs extend longevity. Investment success means clients can retire, educate their children, and buy a home; personal success means “a meaningful life,” beginning with family and extending, he hopes, through a brain institute that benefits as many people as possible.

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