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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]

Those founders, once they misbehave or something goes wrong, they really can't be saved. They're too opinionated, too big. As opposed to a 22-year-old that you certainly can make head of products or head of strategy or head of something. So it was a different time where the aggressiveness to those founders was far greater, which if you implement that, that in 2023 would ruin your reputation.

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

Those founders, once they misbehave or something goes wrong, they really can't be saved. They're too opinionated, too big. As opposed to a 22-year-old that you certainly can make head of products or head of strategy or head of something. So it was a different time where the aggressiveness to those founders was far greater, which if you implement that, that in 2023 would ruin your reputation.

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

That's both the good side and the bad side of being tough. I think you have to overlay the issue of time. Maybe that was appropriate for 1978. It certainly would not have been appropriate in 2020. But internally, He knew how to get you going. And it wasn't the same style for everybody. He happened to know that I needed a good bash on my head to reprogram myself. He knew what I needed.

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

That's both the good side and the bad side of being tough. I think you have to overlay the issue of time. Maybe that was appropriate for 1978. It certainly would not have been appropriate in 2020. But internally, He knew how to get you going. And it wasn't the same style for everybody. He happened to know that I needed a good bash on my head to reprogram myself. He knew what I needed.

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

But on the other hand, just to give you a little sense, when everybody wanted me out as an associate because I was insufferable, it was Don that saw something and said, quote, give the kid more time. So within that toughness, frontally, there was enormous support when you weren't looking. And boy, I think that's the best way to lead and manage.

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

But on the other hand, just to give you a little sense, when everybody wanted me out as an associate because I was insufferable, it was Don that saw something and said, quote, give the kid more time. So within that toughness, frontally, there was enormous support when you weren't looking. And boy, I think that's the best way to lead and manage.

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

To answer the second part of your question, it meant essentially being an unguided missile. It means over competitiveness, do what it takes. Doug, go take that hill. I went and took that hill because that was the mission and the cause and nothing else really mattered. And immaturity plays a role. Lack of experience plays a role. And quite frankly, lack of track record.

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

To answer the second part of your question, it meant essentially being an unguided missile. It means over competitiveness, do what it takes. Doug, go take that hill. I went and took that hill because that was the mission and the cause and nothing else really mattered. And immaturity plays a role. Lack of experience plays a role. And quite frankly, lack of track record.

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

So you are a no track record, abrasive, pain in the ass young man. with a New York accent and clearly a kid from the street. While that doesn't play, that's really not the best marketing message. Now, some people saw through that and they saw a genuine human being. And they work well in those cases. Contrast that with now. I have a bit of a track record. I am a little more mature.

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

So you are a no track record, abrasive, pain in the ass young man. with a New York accent and clearly a kid from the street. While that doesn't play, that's really not the best marketing message. Now, some people saw through that and they saw a genuine human being. And they work well in those cases. Contrast that with now. I have a bit of a track record. I am a little more mature.

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

a little smoother, you know, a coat of paint, not to mislead, but that's the way you lead your life, a little more wisdom. Suddenly, I went from insufferable to charming, and I'm aware of that. And I chuckle because I was not as insufferable then as I was viewed, and I'm not as charming now as I'm viewed. but I'm very well aware of the Marcom transformation.

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

a little smoother, you know, a coat of paint, not to mislead, but that's the way you lead your life, a little more wisdom. Suddenly, I went from insufferable to charming, and I'm aware of that. And I chuckle because I was not as insufferable then as I was viewed, and I'm not as charming now as I'm viewed. but I'm very well aware of the Marcom transformation.

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

And I find it amusing just understanding what human nature is. Everybody tries to position things and now the world is full of baloney and three quarters of stuff you read is not true, blah, blah, blah, blah, blah, blah.

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

And I find it amusing just understanding what human nature is. Everybody tries to position things and now the world is full of baloney and three quarters of stuff you read is not true, blah, blah, blah, blah, blah, blah.

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

First of all, when we look for founders, we also look for Sequoia partners, investors, young people. The same set of traits, use the word insufferable, use the word he doesn't listen, she doesn't listen, or he's belligerent, she's belligerent. Those that other people may view as a negative, we actually view as a positive.

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

First of all, when we look for founders, we also look for Sequoia partners, investors, young people. The same set of traits, use the word insufferable, use the word he doesn't listen, she doesn't listen, or he's belligerent, she's belligerent. Those that other people may view as a negative, we actually view as a positive.

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

Because in order to get something done in life, you can't just walk down Main Street and be a sweetie pie. We look for outlier people, whether it's founders or investors, and outlier people do extraordinary things. Outliers, what do I mean by that? Extra driven, for whatever reason. Maybe daddy told them they weren't good enough and they want to show daddy how good they are.

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

Because in order to get something done in life, you can't just walk down Main Street and be a sweetie pie. We look for outlier people, whether it's founders or investors, and outlier people do extraordinary things. Outliers, what do I mean by that? Extra driven, for whatever reason. Maybe daddy told them they weren't good enough and they want to show daddy how good they are.

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

Maybe they have a twin brother. Twins have a way of competing with one another. They love one another, but they compete with one another. Maybe they failed miserably in their first startup. They're embarrassed and so on. So we look for those things. And sometimes, believe it or not, genetics. I've actually met some people that I'm now convinced they were just wired that way.

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

Maybe they have a twin brother. Twins have a way of competing with one another. They love one another, but they compete with one another. Maybe they failed miserably in their first startup. They're embarrassed and so on. So we look for those things. And sometimes, believe it or not, genetics. I've actually met some people that I'm now convinced they were just wired that way.