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Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses

June 03, 2026 / 29:59

This episode features Bill Ackman, CEO of Pershing Square, discussing investment strategies, AI's impact on business, and the evolution of his investment philosophy.

Ackman shares insights on his approach to long-term investments, emphasizing the importance of business quality and durable growth. He reflects on his early days as an activist investor and how his strategies have evolved over time.

The conversation touches on Ackman's views about OpenAI and its leadership, particularly praising the CFO, Zara, and discussing the potential of AI in various industries. He highlights the need for companies to adapt to AI's disruptive nature.

Ackman also discusses his investments in major tech companies like Microsoft, Meta, and Amazon, arguing that they are undervalued compared to newer firms. He reflects on the challenges of assessing business models in the AI landscape.

The episode concludes with Ackman explaining his strategy for the Howard Hughes Corporation, aiming to build a long-term compounding machine through smart investments in insurance and real estate.

TL;DR

Bill Ackman discusses investment strategies, AI's impact, and his evolving philosophy at Pershing Square.

Episode

29:59
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One of the most provocative and
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interesting investors in the country,
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>> a legendary activist investor,
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>> Persing Square CEO and founder, Bill
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Aman.
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>> Taking a short position and going public
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with it is a pretty serious business.
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Interestingly, some of the best
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businesses in the world are trading at
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the lowest multiples.
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>> We're kind of the rebirth of the closed
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end investment company universe.
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>> What did you think of Zara, the CEO of
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OpenAI? I'm sorry, CFO. Felt like the
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CEO. Yeah, I I was
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>> stop with that stuff.
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>> Uh, actually I was super impressed. Uh,
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made me a lot more bullish on Open AI
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and I thought
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>> right
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>> I thought she should be CEO of OpenAI.
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>> That's what I thought.
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>> I think Sam should be I think Sam should
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be chair. I think he's much better.
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>> There was a question I wanted to ask her
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that we didn't get time which was what's
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it like working with Sam?
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>> I mean that could have been like three
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hours in a documentary.
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>> I wanted to kick this off. So thank you
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so much for being here. We've tried a
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number of times to get you to all in and
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it's great to to finally have you. You
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obviously are a legend that doesn't need
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much of an introduction lately in the
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last number of call it years or months
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or quarters or what have you. It seems
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like your investment philosophy may be
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changing your model uh where you've been
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activist and you've entered positions
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and exited positions and lately you've
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talked a lot about more kind of
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permanent long-term holdings. would love
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to hear a little bit about if that is
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actually a change and how your evolution
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and your investment model has kind of
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changed over over time.
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>> Sure. So I would say the biggest change
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over time is an appreciation for the
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importance of I call business quality
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long-term durable protected
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non-disruptible growth. I would say
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early days you're smaller more liquid
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investor. You don't have to think as
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long term as you become a bigger
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concentrated investor. Uh and over time
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you learn the importance of durable kind
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of growth. That's the most important
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factor. Uh I would say I'm as activist
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as I've ever been. Um but more of it's
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on uh Twitter than than uh I would say
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in the corporate context. And the reason
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for that is when I started in uh Persing
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Square, no one sort of knew who we were.
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And so I actually one of our first
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investments was Wendy's International.
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Wendy's owned Tim Hortons, the Canadian
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coffee and donut chain. And the value of
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Tim Hortons was more than the entire
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value of Wendy's. So we had this very
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simple idea. Buy Wendy's spin-off Tim
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Horton's double our money. And uh we
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bought 10% of the company and I called
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the CEO and he didn't return my call and
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I called him again. He didn't return my
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call. I literally couldn't get a return
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phone call. That was the beginning. Uh
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so we actually called a friend who
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worked at Blackstone and Steve
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Schwarzman agreed to write a fairness
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opinion on what Wendy's would be worth
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if we spun off Tim Hortons. We kind of
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mailed it in and filed it publicly and 6
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weeks later they spun off. Wow.
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>> And then the CEO finally called me back
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and uh he thanked me um and he had
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gotten fired. Um and and uh but he
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thanked me cuz he had a huge exit
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package and and he was very happy. But
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so in the beginning we couldn't get a
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return phone call so we had to and we
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were small so we had to go to a
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conference and we had to you know do
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presentations and go on CNBC. What
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happens over time is you join boards of
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directors you become known as an
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investor. you know, we're kind of a
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constructive shareholder. Um, I know
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pretty much every CEO in the S&P 500
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either directly or one person removed
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and, you know, maybe I age, we've aged a
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bit. Um, but you build kind of a
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reputation and today we buy a stake in a
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company. Sometimes they'll put out a
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tweet saying, you know, we welcome
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Purging Square as a shareholder, but
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they open the door for us. You know, in
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the beginning, we had to bang down the
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door and today so we we get very deeply
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involved in our companies if it's
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needed. uh other companies we own.
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There's no nothing for us to do just be
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to you know just clap.
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>> So you aren't you aren't considered a
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value ad investor at this point.
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>> Yeah. But we only want to add value. I
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the conversation last night was kind of
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an interesting one. You know the best
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investments are one where you don't need
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to join the board and do anything. Well,
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that may be in a startup, but in a
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mature business, it may be.
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>> No, I think in in the public company
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context, one of the valuable things we
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can do that, you know, the problem of
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being a public company today is kind of
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the the very short-term nature of
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markets, analysts, etc. And obviously to
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run a business, a business is a, you
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know, a good one is a forever thing. And
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you want to make decisions in the
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context of decades sometimes or
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certainly three, five years. And how can
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you do that when someone's asking about
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the tax rate in the second quarter? Um,
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and having a big shareholder on the
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board where you can kind of test ideas
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out with the big shareholder before you
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expose them to the public or the big
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shareholder can say, "I'm supportive of
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this initiative even though it's going
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to hurt earnings in the next few
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quarters is a helpful thing."
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>> I just want to connect this last
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conversation with Sarah to this. Um, are
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you an investor in the AI complex and
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how do you underwrite business model
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quality from what you see on the outside
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in in the entire complex?
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>> I mean, yes, effectively we're an
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investor. Actually today we own
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Microsoft, we own Meta, we own Amazon.
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Uh actually I think you're either
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directly or indirectly you're invested
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in AI.
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>> Yeah.
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>> Or it's a threat. So you have to you
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have to understand it.
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>> Um how do I think about AI in a business
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model context?
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>> Business model quality. Yeah.
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>> Look, when you're a concentrated
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investor or investor generally and your
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long-term investor, the most important
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and most challenging thing to do is
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determine what's the risk of disruption.
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What's the risk of two guys, two women
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from Stanford in a garage, you know,
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coming up with something? That risk, I
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think, has gone up uh dramatically. This
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is the greatest era in history to to
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build a business, right? There's
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unlimited access to compute, you know,
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certainly for a startup, uh unlimited
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access to capital, uh and a lot of
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incredible talent, which means that the
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probability of your being disrupted has
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gone up enormously. So the hardest thing
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you have to do as an investor is
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understand you know and and that's
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really where we spend most of our time.
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>> What's your tendency in a moment like
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this then? Do you swing towards the
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chaos or do you reposition to things
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that are maybe more durable and
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defensible from AI where the
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disruptibility is less
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>> what's interesting about markets is
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people always bring their eye to the new
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new thing. Um and the new new thing is
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sort of chips and semiconductors and
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energy and that's where you know uh the
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shorter term capital's going what tends
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to happen is really high quality things
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get left behind. Um, and the same thing
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really happened, you know, I was I was
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there in 2000, you know, when the in the
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in in that sort of bubble. This is, you
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know, this is different. I'm not saying
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this is um, but there's some analogies
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and the analogies are people got excited
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about internet stocks and Bergkshire
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Hathway traded at the lowest valuation I
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think it ever traded out of it history
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is people said, "Okay, that's all old
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stuff." I think a similar thing is
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happening today in a in a sense to
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Amazon and Meta, Microsoft. Those are
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the ones that
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>> these are these are old-fashioned
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companies in kind of this, you know, the
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open AI.
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>> So, they're undervalued in your mind.
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>> Yes.
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>> What else is undervalued?
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>> What about the SAS apocalypse? So, is it
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oversold at this point?
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>> Uh, again, I think it's a careful
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analysis. I worry more about a
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Salesforce um than I do about your kind
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of um I think you got to do the work. I
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think it's one company at a time, but I
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think if you know, if you're a software
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company today, you have to be as AI
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enabled as you can. you can't I I think
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there have been sort of monopolistic
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type profit taking off of customers when
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someone had a kind of a niche software
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product they're charging you know 30,000
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a year or something like this I think
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those companies are really at risk uh
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you know Microsoft when the average
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customer is paying I don't know 50 bucks
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a seat or some small number uh that
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platform is worth a lot more uh less of
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risk
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>> I want to go back um to co because you
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had an incredibly ly viral moment where
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you were on CNBC at that moment and you
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pounded the table and you said this is
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what's going to happen and literally the
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market just ripped and you you were well
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first it went traded massively down you
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were right on that side of the trade and
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then you were on the right side of the
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trade when it ripped back up and then I
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think it was maybe a month or two ago I
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think publicly you basically pounded the
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table and said this market's going way
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higher can you just put us in your head
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like where does that desire to be so
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active and
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you know it it gives you so much room to
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be wrong but then when you're right it
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does add to the lore of Bill Aman of
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which you have a lot. So how do you
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balance that? Where does it come from?
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Like why in these moments do you just
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get so convicted that the that the
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conviction just has to spill out and
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then you're just so out there?
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>> So I've always been like uh my high
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school yearbook epithet was most
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verbose. Uh, and
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>> and that and actually my my friend uh
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actually lives around here. Uh, he his
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quote that he put next to my name in my
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yearbook. It says, "A closed mouth
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gathers no foot." That was his. And so
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that's kind of what I've lived by. I've
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always had this sort of desire to speak
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the truth about things. And um, you
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know, was just talking with Jake
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actually. We had breakfast this morning
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uh, and we're talking about my Rhonda
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uh, post. You remember that one? So like
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you know there's just certain things
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that need to be shared and discussed but
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with respect to markets I actually what
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happened was I was concerned about the
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country because I felt we needed to have
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basically a twoe pause you know this is
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March of uh or February I guess it was
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March of 2020 and I assumed we were
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going to just do a short-term shutdown
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let the virus cool down as hospitals
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were kind of getting overwhelmed and uh
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the president hadn't done that yet. I
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was kind of surprised by this and that
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that was what inspired me to go on TV as
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a way to reach uh President Trump and
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say, "Look, we need to shut down the
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country just for two weeks." You know,
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my uh and I said, "Look, you do this,
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okay? The virus will blow over. Stocks
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are at an incredibly cheap valuation. If
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we handle this correctly, you're going
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to make a ton of money." And we're
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buying. You know, valuation is like a
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tether on the market, right? When it
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gets too high, it's like this rubber
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band that's stretching and inevitably it
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bounces back. But it works the other way
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as well. When stocks get too cheap,
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there's this, you know, the the rubber
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bands actually pulling valuations up
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>> and and so there there are certain
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moments where it gets to that place. And
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sometimes actually if you call that out,
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it causes people to have kind of a
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psychological reset.
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>> What happened recently that caused you
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to call that out?
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>> Stocks just got crazy cheap. Just
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incredibly cheap of really high quality
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companies,
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>> right? what you find extremely cheap in
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fundamentals. fundamentals based on you
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know what's the value of a financial
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assets the present value of the cash it
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generates over it life on that basis
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stocks of really high quality companies
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are really cheap
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>> is there any way to underwrite and you
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know I don't want to pick on specific
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companies but we have the three that are
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going public and then you have like a
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palunteer let's say and these things
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have become very popular in pop culture
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in maxing on subreddits on you
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know the public's consciousness high
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netw worth individuals wanting to buy
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into SPVS that are double
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loaded and then getting wiped off the
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cap tables. Is there any way to
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underwrite 100 times revenue, 50 times
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revenue, 150 times revenue in these
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companies or are these just tremendously
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overvalued because of the demand side?
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>> I think you underwrite a SpaceX the way
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you underwrite a venture capital
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investment.
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>> Interesting. Explain that. Unpack it.
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>> So, everyone here invests in venture,
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right? you know, you bet on, you know,
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who's running it, right? The talent is
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enormous. Um, it's people. They taught
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me, I had a professor business school.
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He said, "People, opportunity, context,
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deal." So on people, SpaceX,
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>> one of one.
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>> Yeah. Opportunity, one of one context,
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you know, incredible. And actually, you
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know, feel bad for Blue Origin, but not
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harmful to SpaceX. The fact that, you
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know, they're their biggest way behind.
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>> Then you get to deal.
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>> Okay. That's the more complicated
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question for SpaceX. Again, we don't
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know what the valuation is going to be,
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but if it's a billion, a trillion750
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billion, then you say, okay, well, let's
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think 5 years out. What does this
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company look like? You know, what is
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Starlink? What's the trajectory of
00:12:13
Starlink? You know, SpaceX is, you know,
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near monopoly in terms of lowcost space
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launch. That's going to become
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increasingly important. And even Amazon
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is going to have to become an even
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bigger customer because they're not, you
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know, Blue Origins, you know, and and
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time, I would say, has become
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increasingly valuable in the AI era,
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right? You you delay a model. We were
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talking, David and I were talking about
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the administration and and his kind of
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stepping in for the president not to
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sign that executive order to kind of
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slow us down.
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>> Allegedly,
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>> you lose a month. You lose a couple of
00:12:43
months today and it means a lot. So I
00:12:44
think the only question I have and I
00:12:46
haven't done the math. I you know I
00:12:47
actually invested in X. I invested in
00:12:49
XAI. I'm in an SPV. Ron Baron said Bill
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you got to invest in SpaceX. So So I'm
00:12:55
I'm I'm in. So now I have So obviously
00:12:57
I'm rooting for kind of a good outcome.
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I just does I haven't done the
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>> Yeah, you have to.
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>> What about
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sorry
00:13:06
>> uh enthropic open AI Palunteer also fall
00:13:08
into this category. Do you underwrite
00:13:10
those as venture investments as well?
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And have you done the the work on those?
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They're venture investments that do what
00:13:15
what's helpful is they're not seed or
00:13:18
series A, right? They're, you know, D or
00:13:21
E, but they're still like venture
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investments. These companies have proven
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they can generate a lot of revenues.
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>> And actually, I was just saying on
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Sarah, I thought she had a very very
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thoughtful
00:13:30
>> uh explanation on how they think about
00:13:32
committing capital, right? And and
00:13:34
that's the thing I haven't heard from on
00:13:36
Open AI, which is why if I were Open AI,
00:13:39
I would be getting that message out
00:13:40
because, you know, from the outside,
00:13:42
you're like, it's a pretty interesting
00:13:43
business model. You got a company that's
00:13:44
spending making capital commitments.
00:13:46
They're massively in excess of, you
00:13:48
know, revenues and how do you do that
00:13:49
and get, you know, it's it's degree of
00:13:51
difficulty, I would say, is hard.
00:13:52
>> Your perch um on the boards of let's
00:13:55
call it these more traditional Fortune
00:13:57
500 type businesses and your
00:13:58
conversations with those CEOs, how are
00:14:01
they thinking about AI? Is it something
00:14:04
that they're tipping into into with
00:14:06
pilots? Are they doing transformation
00:14:08
initiatives? Do they think this doesn't
00:14:10
really apply to us? We'll deal with it
00:14:12
later. What what's your sense of how
00:14:14
they're adopting or embracing AI?
00:14:16
>> I would say every CEO in America today
00:14:19
is like, how do I use AI? How how does
00:14:21
it apply to my business? How is it a
00:14:23
threat? Uh they got to find an internal
00:14:25
champion. They maybe have to recruit
00:14:26
someone from the outside. I would say
00:14:27
it's on the hierarchy of things they
00:14:29
worry about. It's probably number one as
00:14:31
both an opportunity and a threat. So if
00:14:33
you're not paying attention to it, you
00:14:35
you'll I mean your board is going to be
00:14:37
you know asking you first question every
00:14:39
meeting about what you know what how we
00:14:41
dealing with the AI threat, how are we
00:14:43
dealing with the AI opportunity. So it's
00:14:45
absolutely top of mind.
00:14:46
>> Are you seeing much early success? I
00:14:49
mean are through your you know again
00:14:50
through your visibility into these
00:14:52
companies. I mean there's a lot of mixed
00:14:54
signals that we get like McKenzie did a
00:14:56
study and said that 95% of enterprise
00:14:59
initiatives actually fail. Jamaath,
00:15:02
you've made this point around 8090 that
00:15:04
a lot of these enterprises don't really
00:15:05
know how to deploy AI. The the um you
00:15:09
know the fanciest title in Silicon
00:15:10
Valley these days is a for deployed
00:15:12
engineer which is basically a like an IT
00:15:15
consultant who can close the gap between
00:15:18
the promise of AI and the ROI of it. And
00:15:21
I think people are just trying to figure
00:15:23
out like how do we how do we use this
00:15:25
thing? I mean have you seen much actual
00:15:27
success? Is this the is this the
00:15:29
question right now? house is how do we
00:15:30
bridge this gap?
00:15:31
>> So I haven't seen much success
00:15:34
>> uh other than I mean I give you the
00:15:36
Persian square
00:15:37
>> story you know we're tiny little company
00:15:39
how we're using AI today the first use
00:15:41
case is really on the legal side um and
00:15:44
um you know kind of almost almost we
00:15:46
call it compliance back office type you
00:15:48
know functionality I think we're still
00:15:50
super super early in terms of big
00:15:52
companies using AI effectively.
00:15:54
>> Can I ask um or test a thesis with you?
00:15:57
you know the the venture underwriting
00:15:59
model where you think about people
00:16:00
you're underwriting a founder and their
00:16:02
capacity to lead and redirect the
00:16:04
organization in a changing environment
00:16:07
and technology environment market
00:16:08
environment and whatnot and we have seen
00:16:11
repeatedly similar success at scale if
00:16:13
the company is still founder where the
00:16:15
founder feels like they have the
00:16:16
authority to make all the radical
00:16:18
decisions needed to make sure that that
00:16:20
company persists and changes as needed
00:16:22
in a changing environment. Have you
00:16:24
looked at founder-led companies versus
00:16:26
non-founder-led companies where perhaps
00:16:29
the founders really do have an inherent
00:16:31
advantage in being able to navigate this
00:16:33
these changing environments and actually
00:16:35
generate outsized returns over time? And
00:16:37
I asked this particularly as it relates
00:16:39
to the SAS apocalypse and if you take a
00:16:40
look at the companies that are founder
00:16:42
led today versus not. If you're not
00:16:44
founder led, you have an incentive to
00:16:45
not make a mistake and get fired. If
00:16:47
you're founderled, you don't give a
00:16:48
Your job is to make sure the
00:16:49
company
00:16:50
>> Yeah, I think the answer is exactly what
00:16:51
you said. I think the problem is that
00:16:52
the average life of an S&P 500 CEO is
00:16:55
probably, I don't know, four years or
00:16:57
three year, three and a half years or
00:16:58
something like this and you're focused
00:17:00
on, you know, kind of shorter term
00:17:02
compensation. You don't generally don't
00:17:03
have a big economic stake in the
00:17:05
business. You're a founder. This is your
00:17:07
entire life. It's your entire
00:17:08
reputation. It's not like you're going
00:17:09
to go get another job. You you got to
00:17:11
kind of make it work. And also when
00:17:12
you're in the boardroom, you have the
00:17:14
authority of either being a major
00:17:15
voting, you know, voice or or a u you've
00:17:19
got a huge economic stake in the
00:17:20
company. You know, when we join a board
00:17:22
of a company, we're often the largest or
00:17:24
sec the largest non index fund type
00:17:26
shareholder. That kind of gives us, you
00:17:28
know, a little bit of a disproportionate
00:17:29
voice in the boardroom. Imagine if you
00:17:31
have that and you're CEO of the company,
00:17:33
right? So I think that does give you and
00:17:35
and also if you've gotten to be a
00:17:36
successful founder over time uh
00:17:38
guaranteed that you've made a number of
00:17:40
very challenging call calls over time
00:17:42
that turned out to be right otherwise
00:17:44
you wouldn't be there. And so you look
00:17:45
at Mark Zuckerberg right when he bought
00:17:47
I don't know Instagram everyone was like
00:17:49
shocked at the price paid or WhatsApp
00:17:51
you know these seemed like you know sort
00:17:52
of outside the you know the company only
00:17:54
had whatever 19 employees or something
00:17:55
when he paid a billion something. Um but
00:17:58
you make enough of those calls um and uh
00:18:02
you can make the other challenging call.
00:18:04
>> Is this antithetical to a Ben Graham
00:18:06
investing model like you have to have a
00:18:08
different set of skills as an investor
00:18:09
to to identify this talent for?
00:18:11
>> Yes. I mean Ben Graham is a really
00:18:14
important voice for investors and that
00:18:16
he said look you got to think about a
00:18:17
business a stock certificate is an
00:18:20
interest in a business as opposed to
00:18:21
just this piece of paper. That's
00:18:22
probably one of his most important kind
00:18:24
of apherisms. But he was investing for
00:18:26
the most part in liquidations. He was
00:18:28
invest you know in the days of Ben
00:18:30
Graham where there weren't there's no
00:18:32
Edgar system and in order to get a 10K
00:18:35
filing you had to go to the headquarter
00:18:36
of the company. there were a lot of
00:18:37
stocks trading at, you know, basically
00:18:38
the cash on the balance sheet and his
00:18:40
business model was, you know, buying
00:18:42
these things at stupidly cheap prices
00:18:43
and eventually um but Bened Graham made
00:18:46
most of his money investing in, I don't
00:18:48
know, Geico or something uh you know,
00:18:50
not
00:18:50
>> tell us um a little bit about, you know,
00:18:53
there's this sort of activist and
00:18:54
significant shareholder, but then
00:18:56
there's Howard Hughes and you've talked
00:18:58
a little bit about Berkshire Hathaway
00:19:00
2.0 or just being inspired by that.
00:19:02
Chimapi, you were inspired by it for a
00:19:04
long time.
00:19:04
>> Oh, Bill just took Persian Square
00:19:05
public.
00:19:06
>> Yeah. But with with the Howard Hughes
00:19:08
Corporation specifically, tell tell us
00:19:10
about that effort because you're
00:19:12
operating that business.
00:19:13
>> There's a book uh I think it's called
00:19:14
the financial history of Berkshire
00:19:16
Hathway. That's for geeks. Um, basically
00:19:19
this guy uh went back and read every 10
00:19:23
Q whatever he actually went through the
00:19:24
filings, looked at every deal that
00:19:26
Buffett ever did and you follow him over
00:19:28
uh 60-year period of time and the vast
00:19:31
majority of the value he created at
00:19:32
Bergkshire was through it actually the
00:19:34
ownership of an insurance operation and
00:19:36
what's interesting about insurance is
00:19:38
that uh you know running an insurance
00:19:41
company you have two jobs one is you you
00:19:43
know write business right you take risk
00:19:45
um you collect premiums in exchange for
00:19:47
the obligation to pay future claims and
00:19:49
then you get that you get money up front
00:19:52
and you responsibility is to invest that
00:19:53
money. Uh the vast majority of insurance
00:19:56
companies focus only on the liability
00:19:58
side of the balance sheet. Buffett was
00:19:59
really the first to do focus on actually
00:20:02
more on the asset side of the balance
00:20:03
sheet than on the liability side. And
00:20:05
over time on the liability side if you
00:20:07
if you manage the assets of an insurance
00:20:09
company well and the liabilities well
00:20:11
you can build this enormously profitable
00:20:13
compounding taxefficient machine over
00:20:15
time. And the question is, why haven't
00:20:17
other people done this? And the answer
00:20:20
is if you're really good at investing,
00:20:22
you go work for a hedge fund, you go
00:20:24
work for Fidelity, you go work for
00:20:26
Wellington, but you don't go work for an
00:20:28
insurance company. So the insurance
00:20:30
company's ability to recruit investment
00:20:31
talent is very limited. Buff Buffett
00:20:34
owned half the company. He was really
00:20:35
good at investing, which is why it
00:20:36
worked. So what we're doing is we're,
00:20:38
you know, Buffett started with a crappy
00:20:39
textile company, effectively liquidated
00:20:42
it over time, reinvested in insurance,
00:20:44
and then invested the assets. Well,
00:20:47
Howard Hughes is actually a really
00:20:48
interesting company, but it's a business
00:20:50
that Wall Street has not cared about for
00:20:51
a long period of time. We created it out
00:20:53
of the bankruptcy of of General Growth.
00:20:56
It was a spin-off of all the other
00:20:57
assets, and it's a company that owns
00:20:59
these small cities. So, I bet a lot of
00:21:01
people here have heard of Summerland
00:21:03
because uh a lot of the tech community
00:21:05
has moved from California to Las Vegas,
00:21:07
but we own this small city, 26,000 acres
00:21:11
of land. Uh we own all the commercial
00:21:14
land, we own all the residential land,
00:21:15
we sell lots of home builders, we build
00:21:17
a downtown, we build buildings. Uh it's
00:21:20
a bit like the Irvine company. You know,
00:21:22
Don Brand created probably hundred
00:21:24
billion dollars of personal wealth
00:21:25
managing a small city. So super cool
00:21:27
company, but the time frame is decades
00:21:30
as opposed to quarters. So Wall Street's
00:21:33
never cared. It's always traded at a
00:21:34
huge discount. So Buffett bought into a
00:21:36
textile business at a discount to
00:21:37
liquidation value at $63 a share, you're
00:21:40
owning Howard Hughes at a discount to
00:21:42
liquidation value. What we're doing is
00:21:43
instead of reinvesting all the cash the
00:21:45
business generates into real estate,
00:21:47
we're going to reinvest all the cash
00:21:48
into insurance. Uh we're next within the
00:21:51
next week or so,
00:21:52
>> you're in the business of building this
00:21:53
flywheel. We're going to build this into
00:21:55
a compounding machine over the next 50
00:21:57
years. It's something I've always wanted
00:21:58
to do. We have the benefit of
00:22:01
understanding both the insurance side of
00:22:02
the business and we can manage the
00:22:04
assets well and you can buy it at, you
00:22:06
know, whatever 60 cents on the dollar.
00:22:08
>> How do you think about investing the
00:22:09
assets of this insurance company? So,
00:22:11
>> so what Buffett did is he took 100% of
00:22:12
the insurance float and put the money in
00:22:15
short-term treasuries. So he took no
00:22:16
risk on kind of policyholder funds and
00:22:19
he took 100% of the surplus of the
00:22:21
insurer the equity and invest in common
00:22:23
stocks and that's what we're going to
00:22:24
do. Um and I think we can build a really
00:22:26
profitable insurance company. We're
00:22:28
starting at a very small scale. The
00:22:30
company's got like a $4 billion market
00:22:31
cap and the goal is to build it into a
00:22:33
trillion dollar thing over time
00:22:35
compounding. The other thing Buffett did
00:22:36
well is that he didn't issue any stock
00:22:38
or not for a very long time. So they you
00:22:40
know he started with a million shares
00:22:42
and today he has effectively like a
00:22:43
million. this is the future for very
00:22:45
talented managers like yourself versus
00:22:48
the traditional long short fund or do
00:22:50
you think they sit side by side?
00:22:51
>> I think it's hard to do this because you
00:22:53
need control of a public company and you
00:22:56
have to be not in a get-richquick
00:22:58
mindset and there if you're in the
00:22:59
get-richqu it's easier to go to Citadel
00:23:01
or Millennium or one of these.
00:23:02
>> Why does it have to be public?
00:23:04
>> Why does it have to be public? It
00:23:06
doesn't doesn't have to be public.
00:23:07
>> Why did you choose to take it?
00:23:09
>> Uh you know we we got here by accident,
00:23:12
right? So the most successful equity
00:23:14
investment we've ever made is we bought
00:23:15
this company called General Growth. We
00:23:16
bought the stock of a company going
00:23:17
bankrupt. Sort of the most contrarian
00:23:19
investment you can make. Stock went from
00:23:21
you know uh $20 billion market cap to
00:23:23
100 million and we bought a basically uh
00:23:27
a third of the company or 27% of the
00:23:30
company at uh $200 million market cap
00:23:32
and there was 27 billion of debt and the
00:23:34
bankruptcy emerg and the strategy we
00:23:36
said is look the assets are worth more
00:23:37
than liabilities. we're going to do the
00:23:39
first uh restructuring where the equity
00:23:42
gets to keep their investment in the
00:23:43
company. Two years later, we emerged
00:23:45
from Chapter 11. The stock went from 34
00:23:46
cents to $34. But part of the
00:23:49
restructuring was spinning off this
00:23:50
thing called Howard Hughes. And it was
00:23:52
really all of the junk that didn't
00:23:53
belong in the company that the analysts
00:23:55
hated. Um and so we did it uh sort of an
00:23:59
inadvertent investment. And you know, 15
00:24:02
years later, we haven't really created
00:24:03
much value with it. So we said, "Look,
00:24:05
we've got to you know, the market
00:24:06
doesn't like this thing. the market a
00:24:08
company has to earn a return in excess
00:24:10
of its cost of capital in order for a
00:24:12
stock to go up and the you know Elon's
00:24:14
done an amazing job keeping the cost of
00:24:15
capital of his company's really low you
00:24:17
know SpaceX goes public at a trillion
00:24:19
750 billion will probably be the lowest
00:24:21
cost of capital equity capital
00:24:24
transaction in the history of the world
00:24:26
the problem with this company because
00:24:27
it's real estate because it's
00:24:28
development because it's land ownership
00:24:30
the market says the cost of capital is
00:24:31
really high and you can only earn a
00:24:33
certain return of real estate so what
00:24:34
we're doing is we're repurposing the
00:24:36
real estate assets and we're
00:24:38
transforming the company into a much
00:24:39
higher returning kind of business.
00:24:40
>> The last few years you've become
00:24:42
incredibly famous. I mean just to kind
00:24:43
of put a fine point on the word. How
00:24:45
does that change and influence the way
00:24:48
that markets work because like you know
00:24:50
your voice gets amplified now. You also
00:24:53
have other places where other voices get
00:24:55
heard many people's whose names you
00:24:57
don't even know. You go into Wall Street
00:24:58
bets it's every random Tom Dick and
00:25:00
Harry with an opinion. tell us the way
00:25:03
the markets have changed with notoriety,
00:25:06
fame, social media influence, not just
00:25:08
yours, but in general.
00:25:09
>> Yeah, I don't think markets have changed
00:25:11
as a result of anything that's happened
00:25:13
with me or follower growth on on
00:25:15
Twitter. I think the Ryan Cohen guy, you
00:25:18
know, the GameStop guy.
00:25:20
>> Yeah.
00:25:20
>> You know, that is a change in markets
00:25:22
when um you know, a stock can trade at a
00:25:26
valuation well above its value simply on
00:25:30
the personality and the ability to
00:25:34
>> vibes
00:25:34
>> to to gather up, you know, armies of
00:25:37
followers. You know, the the fascinating
00:25:39
thing about liquidity and valuation is
00:25:43
the higher a stock price goes, and it's
00:25:46
going to sound sort of intuitive, but
00:25:49
it's not, the more valuable the company
00:25:51
becomes. You know, there's actually the
00:25:54
increase in value of the company
00:25:55
increases the value of the company,
00:25:57
right? Because it lowers the cost of
00:25:58
capital, it gives you more flexibility,
00:26:00
gives you the ability to issue stock,
00:26:03
raise capital, acquire other businesses.
00:26:05
And so, you know, getting back to the
00:26:07
Elon example, uh it's really his I would
00:26:11
say he's a better example of this. We've
00:26:12
not taken advantage of this at all.
00:26:14
Maybe we should,
00:26:15
>> but he built an army of believers and
00:26:17
followers
00:26:18
>> uh that enabled uh Tesla to be built.
00:26:22
>> Um you know, let me end as we wrap up
00:26:25
with a somewhat of a pointed question.
00:26:27
You're an incredible investor. If there
00:26:29
are people, if we want to be maximally
00:26:31
aligned with Bill Aman,
00:26:34
is the best way to be an LP in Persing
00:26:37
Square or is it best to go into the
00:26:38
market and buy?
00:26:40
>> So, we have two I think there are three
00:26:43
ways you can invest with us that are all
00:26:45
different and will achieve different
00:26:46
things. One is something entity called
00:26:48
Purging Square, which is the management
00:26:50
company at Purging Square. I think it's
00:26:51
one of the most interesting kind of
00:26:53
intellectually businesses because it's a
00:26:56
uh it's the entity that receives fees on
00:26:58
these three permanent capital vehicles
00:27:00
we manage. So, it's a royalty on the
00:27:02
compounding of investments in these
00:27:05
entities and there's no capex in the
00:27:07
business. So, we're going to pay out
00:27:08
basically all of our profits and we're
00:27:10
going to grow as quickly as the
00:27:12
underlying assets uh compound. So if you
00:27:14
invested a dollar in Persian Square, you
00:27:17
know, 22 years ago, that's that became
00:27:21
um you know uh 20 uh I think I should
00:27:26
know this number. It's like 27 or 28
00:27:29
times net of all fees. Wow. Okay. Over
00:27:31
over 22 years. Had we charged the fees
00:27:33
of this public vehicle, uh that number
00:27:36
would have been um you know uh 37 times
00:27:39
I'm sorry, no more in the something in
00:27:41
the mid-40s. Okay. What this means is we
00:27:43
now have a public vehicle that charges
00:27:45
only a 2% fee. We've got a one in London
00:27:47
that charges an incentive fee. If we
00:27:49
compounded the rates we have
00:27:50
historically, we'll have 35 times the
00:27:53
assets under management uh in 22 years.
00:27:55
So we'll go from 25 billion of assets to
00:27:57
something approaching a trillion. We
00:27:59
don't have to hire another person uh and
00:28:01
we don't have to spend another dollar if
00:28:03
you will on overhead. That that's a
00:28:04
pretty interesting business. So I like
00:28:05
that one. So Persian Square, if you want
00:28:07
to invest with us as a investor, invest
00:28:09
in something called PSUS and you own a
00:28:11
portfolio of our best ideas and it's
00:28:13
trading at an 18% discount to cash. You
00:28:16
want to believe that we can build the
00:28:17
next Bergkshire Hathaway, you own Howard
00:28:19
Hughes. We got three different ways.
00:28:20
>> Yeah, I bought some Howard Hughes. I
00:28:21
think following you on Twitter and going
00:28:24
the going direct movement does allow you
00:28:27
to communicate directly your vision and
00:28:30
and that actually makes it much easier
00:28:31
to to place the bet. And so I I do think
00:28:33
it has a profound impact because prior
00:28:36
to your extremely long tweets that have
00:28:40
been parodyied now there's an incredible
00:28:43
meme of a Bill Aman tweet coming in
00:28:45
which is
00:28:46
>> you did that extended iPhone that's a
00:28:48
foot tall.
00:28:48
>> No it was that was my Halloween costume
00:28:51
>> for last year.
00:28:53
>> You would have written something
00:28:54
shorter. You just didn't have the time.
00:28:55
Yeah.
00:28:57
>> Yeah. I guess uh I don't let other
00:28:59
people read, you know, um my
00:29:00
>> Do you do you like have anybody read it?
00:29:04
>> On the uh the Rhonda tweet uh which had
00:29:06
some legal implications, I did have my
00:29:08
communications guy and a lawyer
00:29:10
>> a friend who's a lawyer read it, but I
00:29:12
only gave him a few minutes cuz I was so
00:29:13
excited. Once I write something I really
00:29:15
like, I just want
00:29:16
>> Yeah. I agree. I agree. And the
00:29:19
torpedoes
00:29:21
does this too. He starts getting a
00:29:23
little bit frantic when he's writing
00:29:24
something and then he's like it and he
00:29:25
just hits.
00:29:26
>> I just hit that.
00:29:27
>> By the way, it's a very powerful thing
00:29:29
to be able to share your view and push a
00:29:30
button and reach 2.2 million people. So,
00:29:32
I I'll I'll have to Why don't we just a
00:29:34
picture on stage and I'll send it out.
00:29:35
>> Hell yeah. That's great. Let's do it.
00:29:37
>> Liquidity.
00:29:38
>> Gone all in.
00:29:39
>> All right.
00:29:41
Thank you.
00:29:56
Hey,

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Episode Highlights

  • Bill Aman on Investment Philosophy
    Bill Aman discusses the evolution of his investment strategy towards long-term durable growth.
    “The biggest change over time is an appreciation for business quality.”
    @ 01m 28s
    June 03, 2026
  • The Importance of Valuation
    Aman emphasizes the significance of valuation in the stock market and its psychological impact.
    “Valuation is like a tether on the market.”
    @ 09m 58s
    June 03, 2026
  • AI as an Investment Opportunity
    Aman shares insights on investing in AI and its implications for businesses.
    “Every CEO in America today is like, how do I use AI?”
    @ 14m 19s
    June 03, 2026
  • The Founder’s Dilemma
    Being founder-led means you have a personal stake in the company's success.
    “This is your entire life. It’s your entire reputation.”
    @ 17m 05s
    June 03, 2026
  • Buffett's Investment Strategy
    Buffett focused on managing assets effectively, creating a compounding machine.
    “You make enough of those calls, and you can make the other challenging call.”
    @ 17m 58s
    June 03, 2026
  • Transforming Real Estate
    Repurposing real estate assets can lead to higher returns for companies like Howard Hughes.
    “The market says the cost of capital is really high.”
    @ 24m 31s
    June 03, 2026
  • Power of Social Media
    The ability to share insights directly can amplify influence in the market.
    “It’s a very powerful thing to be able to share your view and push a button.”
    @ 29m 29s
    June 03, 2026

Episode Quotes

  • We're kind of the rebirth of the closed end investment company universe.
    Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses
  • A closed mouth gathers no foot.
    Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses
  • Stocks just got crazy cheap. Just incredibly cheap of really high quality companies.
    Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses
  • This is your entire life. It’s your entire reputation.
    Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses
  • You make enough of those calls, and you can make the other challenging call.
    Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses
  • The market says the cost of capital is really high.
    Bill Ackman: Investment Strategy, What the Market is Missing, How AI Breaks Businesses

Key Moments

  • Investment Evolution01:28
  • Market Valuation09:58
  • AI Insights14:19
  • Founder-led Success17:05
  • Buffett's Strategy17:58
  • Real Estate Transformation24:31
  • Social Media Influence29:29

Words per Minute Over Time

Vibes Breakdown

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