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Transcript of Bill Ackman Interview: Holy Grail of Investing Podcast

The Contrarian Playbook That Built a 36 Billion Dollar Empire Bill Ackman

Editor’s Note: In this episode of The Holy Grail of Investing, billionaire hedge fund manager Bill Ackman of Pershing Square sits down with Tony Robbins and Christopher Zook to explain how he thinks about risk, downside protection, and long-term investing. Ackman covers his concentrated, activist approach, the launch of Pershing Square USA (PSUS), his plan to build Howard Hughes into a “Berkshire Hathaway for the next generation,” and the lessons he has learned from his biggest mistakes. Whether you invest in public or private markets, this conversation offers practical insight into contrarian thinking, market psychology, and building lasting wealth. This interview was premiered on September 8, 2026.

TRANSCRIPT:

Introduction

TONY ROBBINS: (00:00:00 – 00:00:06) Hey everyone, welcome to the Holy Grail of Investing Podcast. I’m Tony Robbins, along here with my partner and co-host Christopher Zook.

TONY ROBBINS: (00:01:21 – 00:02:07) Bill’s known for his willingness to take on the contrarian view, maintain his conviction when consensus disagrees, and really make concentrated investments based on an extraordinary depth of research and understanding. And his investment returns, as you’ll learn, have been extraordinary.

Today, we’re going to discuss how Bill thinks about risk and downside, the importance of long-term investing, active ownership, and the evolution of public and private markets, and what investors can learn from someone who’s really willing to think a bit independently. So, Bill, first of all, you’re a legend in the business and it’s just a pleasure to meet you. Thanks for joining us on the podcast.

BILL ACKMAN: (00:02:07 – 00:02:08) Yeah, delighted to be here.

Bill Ackman’s Origin Story

TONY ROBBINS: (00:02:09 – 00:02:54) Thank you. Listen, your investment philosophy has always been something that people have stood out for, your ability to stand out from the crowd. But before we get into that and the way you evaluate risk and so forth, we’d like to start out with a little background. Everybody knows someone’s background, kind of their origin story, so to speak.

And I remember reading a story about you where they said you bet your father, I think your bar mitzvah money, for a couple thousand dollars of the money that you would get a perfect 800 score on the SAT. So it sounds like you’ve had some confidence early in life. Tell us a little bit, if you would, about that story, but also what really started you out in the financial business almost 34 years ago. What pulled you to it? Was it numbers? Was it people you knew? We’re curious to know how you kind of started out to move in the direction of the path where you are today?

BILL ACKMAN: (00:02:55 – 00:03:07) Sure. So the first on the story, I was a pretty cocky kid. And then I had pre— they— was the year before I did the SAT, they released a couple of SATs. So I had taken them. So I had a pretty good idea how I was going to do.

TONY ROBBINS: (00:03:08 – 00:03:08) Okay.

BILL ACKMAN: (00:03:08 – 00:03:35) And I bet my dad— but I would consistently do perfect on the verbal and I’d somehow miss a few questions on the math. So I bet my dad that I get 800 on the verbal because that I thought was kind of a lock. And I had $2,000, which was my kind of life savings, more from odd jobs than from bar mitzvah money, I would say. But the Friday before the Saturday of the test, my dad canceled the bet.

TONY ROBBINS: (00:03:36 – 00:03:36) Oh wow.

BILL ACKMAN: (00:03:37 – 00:03:38) Yeah. And I—

TONY ROBBINS: (00:03:38 – 00:03:42) was that a mercy? Was that a mercy decision, or—

BILL ACKMAN: (00:03:42 – 00:04:05) I think he was worried he was going to lose, and $2,000 was real money, and he had— my dad was a successful guy, but he was an entrepreneur in the mortgage brokerage business, and he had a couple years we didn’t make any money. And ’87, which is when I took that test, was a bad year. No, it wasn’t ’87, it would have been ’83.

TONY ROBBINS: (00:04:05 – 00:04:05) Okay.

From Real Estate to Value Investing

BILL ACKMAN: (00:04:05 – 00:06:32) It was not a good year in the real estate business. And he, I think he didn’t want to lose $2,000. And anyway, I ended up getting one question wrong, so I was actually very happy that he— That’s that story.

In terms of investing, so I actually, after college, I went to work for my dad, and his kind of real estate little boutique. And I was selling office buildings, arranging financing, things such as this. And it seemed to me that the people having more fun were the people making the investments as opposed to the people providing the service, if you will, the kind of investment banker type. At one point, I said to my dad, I said, look, I’d really like to learn how to be an investor. Who’s a good investor in your friend group? He recommended a guy by the name of Leonard Marks, who he said was a fantastic stock market investor.

I went to see this guy. He recommended I read a book, a famous book, Ben Graham’s “The Intelligent Investor.” I read it and I was like, wow, this is pretty cool. The next thing I read was a Berkshire Hathaway, Warren Buffett annual letter. And the Buffett stuff is obviously very compelling, and it kind of draws you in. And I started getting obsessed with it.

I would— McGraw-Hill had a bookstore on 50-something and 6th Avenue. It was the best business bookstore in New York. This is obviously pre-Amazon. And I’d go over there. And during lunch, from 12:00 to 1:00, I would just read books. Yeah. And anything I could find on investing. And that’s how I got captured by it.

And then I went to Harvard Business School for the purpose about learning how to be an investor.