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Doug Leone

๐Ÿ‘ค Speaker
328 total appearances

Appearances Over Time

Podcast Appearances

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

It's truth be known for the first 20 years, I did not know whether he had a heart. It was all pure business. It was all for the cause of generating returns for our clients, most of which are endowments and foundations. So for the first, I would say, 15, 20 years, He was visionary, but extremely tough, and certainly dedicated to the cause.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

It's truth be known for the first 20 years, I did not know whether he had a heart. It was all pure business. It was all for the cause of generating returns for our clients, most of which are endowments and foundations. So for the first, I would say, 15, 20 years, He was visionary, but extremely tough, and certainly dedicated to the cause.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

At his eulogy, I was very amused and interested to find out from his kids that they spoke of him as having his huge heart when he went home. And it was really interesting how he segregated his work life from his home life. As he got older and developed a sense of history and put himself in perspective of other leaders, there were certain things he did not want to do.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

At his eulogy, I was very amused and interested to find out from his kids that they spoke of him as having his huge heart when he went home. And it was really interesting how he segregated his work life from his home life. As he got older and developed a sense of history and put himself in perspective of other leaders, there were certain things he did not want to do.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

He did not want to be one of the older folks that stuck around too long. He had images and knowledge of other leaders his age or a little younger that were falling asleep in meeting, and there was starting to be a drag on their partnerships. And he was very cognizant. of not wanting to do that.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

He did not want to be one of the older folks that stuck around too long. He had images and knowledge of other leaders his age or a little younger that were falling asleep in meeting, and there was starting to be a drag on their partnerships. And he was very cognizant. of not wanting to do that.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

And the other thing he was very cognizant of is, boy, how do we leave Sequoia in the best possible place for the next generation? And it was interesting that he chose, and I say chose as if he's pointed us out, he had his own subtle way of choosing. assigning Carrie, maybe two of us at 10% more than the other folks. That's how he chose leadership.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

And the other thing he was very cognizant of is, boy, how do we leave Sequoia in the best possible place for the next generation? And it was interesting that he chose, and I say chose as if he's pointed us out, he had his own subtle way of choosing. assigning Carrie, maybe two of us at 10% more than the other folks. That's how he chose leadership.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

That he chose younger folks that he was willing to mentor. And I would just say that the heart showed up and it was a transformation. Not a transformation out of weakness, but a transformation out of wisdom. And you get to see his heart and how much he deeply cared and how much he cared to mentor and how much he loved youth and how much he loved new ideas and so on.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

That he chose younger folks that he was willing to mentor. And I would just say that the heart showed up and it was a transformation. Not a transformation out of weakness, but a transformation out of wisdom. And you get to see his heart and how much he deeply cared and how much he cared to mentor and how much he loved youth and how much he loved new ideas and so on.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

So very, very, very interested, very interesting human being for the time in which he lived. He would sell shares at 2 billion, not buy shares at 2 billion. Back in his day, if you reached 2 billion or 3 billion, that was a huge exit. So there was the learning curve of a world that was changing at a rapid pace. He understood that he wasn't going to adjust to that world. He got out of the way.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

So very, very, very interested, very interesting human being for the time in which he lived. He would sell shares at 2 billion, not buy shares at 2 billion. Back in his day, if you reached 2 billion or 3 billion, that was a huge exit. So there was the learning curve of a world that was changing at a rapid pace. He understood that he wasn't going to adjust to that world. He got out of the way.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

He never asked a question unless he was asked. The only comments he made once he stepped down, comments when he was asked for his opinion. I found that extremely interesting. He was the ultimate of what the, if you will, the old king should do. In fact, I model my behavior, now being the old king, to his. Never intrusive, always helpful, always ready to assist, but never second-guess.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

He never asked a question unless he was asked. The only comments he made once he stepped down, comments when he was asked for his opinion. I found that extremely interesting. He was the ultimate of what the, if you will, the old king should do. In fact, I model my behavior, now being the old king, to his. Never intrusive, always helpful, always ready to assist, but never second-guess.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

I remember attending a meeting with a founder. And as we walk out of the meeting, Don only wrote in green ink, yellow pads and green ink. And in green ink, he left a note on the table, said, Doug, not fit to listen to founders. And he just left it there for me to see. And in this new day and age, everybody wants weekly feedback. Why should I do better? This and that.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

I remember attending a meeting with a founder. And as we walk out of the meeting, Don only wrote in green ink, yellow pads and green ink. And in green ink, he left a note on the table, said, Doug, not fit to listen to founders. And he just left it there for me to see. And in this new day and age, everybody wants weekly feedback. Why should I do better? This and that.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

Let me tell you, you read that note from Don Valentine, that's all the feedback you need for the next 12 months. You have to break that feedback down. What does he say that? You certainly don't go in his office and say, Don, what do you mean by that? You know what you mean. And you understand maybe you were too aggressive, the wrong style.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

Let me tell you, you read that note from Don Valentine, that's all the feedback you need for the next 12 months. You have to break that feedback down. What does he say that? You certainly don't go in his office and say, Don, what do you mean by that? You know what you mean. And you understand maybe you were too aggressive, the wrong style.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

The other side of being too tough, he was tough on founders. But keep in mind, we were dealing at a time where we were investing in semiconductors. The founders were not the 22-year-old who created new industries because of the internet or mobile. They were engineering managers at a chip company that started a new company, maybe ages 40 to 50.

Invest Like the Best with Patrick O'Shaughnessy
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

The other side of being too tough, he was tough on founders. But keep in mind, we were dealing at a time where we were investing in semiconductors. The founders were not the 22-year-old who created new industries because of the internet or mobile. They were engineering managers at a chip company that started a new company, maybe ages 40 to 50.

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