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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]

Partner, someone a little older, are they on the right side of an argument? Do they have the courage to have an opposing point of view when six people have another point of view? You're about to be partner. Do you have a history of being right? When you're on five boards, can you point to two that we are going to generate? Knowing we all made the investments, but you were the one that pushed it.

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

Partner, someone a little older, are they on the right side of an argument? Do they have the courage to have an opposing point of view when six people have another point of view? You're about to be partner. Do you have a history of being right? When you're on five boards, can you point to two that we are going to generate? Knowing we all made the investments, but you were the one that pushed it.

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

That's how we measured it. Are you a good human being? Do you use the we pronoun a lot? Are you likable to founders? Can you win situations? Do you have the smarts to ask for help? Because we don't care if you win and ask for help. That's a win. That's an everybody win. But you know what's terrible? When you lose by yourself because you had the ego or you didn't read the tea leaves right.

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

That's how we measured it. Are you a good human being? Do you use the we pronoun a lot? Are you likable to founders? Can you win situations? Do you have the smarts to ask for help? Because we don't care if you win and ask for help. That's a win. That's an everybody win. But you know what's terrible? When you lose by yourself because you had the ego or you didn't read the tea leaves right.

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

Those are the things we look at.

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

Those are the things we look at.

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

Here's the thesis. Here's one or two reasons why one of it, and that's 17 reasons. Here's the supporting data. Here's the opposing data. An intellectual honest memo that gives you both sides, but then argues at the end that in spite of both sides, you think side A is more important for the following three reasons, and therefore we recommend that investment.

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

Here's the thesis. Here's one or two reasons why one of it, and that's 17 reasons. Here's the supporting data. Here's the opposing data. An intellectual honest memo that gives you both sides, but then argues at the end that in spite of both sides, you think side A is more important for the following three reasons, and therefore we recommend that investment.

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

With an appendix with the reference checks that either are the full reference or a summary two lines on top, because not everybody's going to read the whole reference. And you do that in three pages, not in 32 pages, not in these investment banking, let me show you how hard I work, 35 pages that nobody reads. Nobody reads. A two to three page memo, we all read.

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

With an appendix with the reference checks that either are the full reference or a summary two lines on top, because not everybody's going to read the whole reference. And you do that in three pages, not in 32 pages, not in these investment banking, let me show you how hard I work, 35 pages that nobody reads. Nobody reads. A two to three page memo, we all read.

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

Frank Slootman, who's, when you net it out, the execution is 90% of the goal. Execution is strategy for breakfast. And he executed, take no prisoner. Don't give me this bologna that you need. Cappuccino on 9-15 to be productive. No crab. Everybody buys in. Go, go, go. Because if you want a great culture, nothing builds a great country like winning. And all the other things are irrelevant.

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

Frank Slootman, who's, when you net it out, the execution is 90% of the goal. Execution is strategy for breakfast. And he executed, take no prisoner. Don't give me this bologna that you need. Cappuccino on 9-15 to be productive. No crab. Everybody buys in. Go, go, go. Because if you want a great culture, nothing builds a great country like winning. And all the other things are irrelevant.

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

David Velez of NewBank, probably the second best CEO I've been in business with after Frank. Frank has great execution. David Velez has vision and very strong execution and the blend of the two. And then I'll probably bring Elon, if he's serious. We're not talking about should I be CEO of Twitter. Elon on point to discuss scale of ambition. Those would be my three dinner guests.

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

David Velez of NewBank, probably the second best CEO I've been in business with after Frank. Frank has great execution. David Velez has vision and very strong execution and the blend of the two. And then I'll probably bring Elon, if he's serious. We're not talking about should I be CEO of Twitter. Elon on point to discuss scale of ambition. Those would be my three dinner guests.

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

Let me give you the investment thesis on NewBank. The best investment thesis are very simple. Let me give you the new bank investment thesis in 30 seconds. The seven largest market cap company in Brazil are all banks. I went to see four banks on every corner. Let's go try to get a credit card. You wait in a line outside. You finally get let in. Six weeks.

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

Let me give you the investment thesis on NewBank. The best investment thesis are very simple. Let me give you the new bank investment thesis in 30 seconds. The seven largest market cap company in Brazil are all banks. I went to see four banks on every corner. Let's go try to get a credit card. You wait in a line outside. You finally get let in. Six weeks.

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

He says, we think we can upend us with technology. So when he came to us, we only gave him one word of advice. Don't build a fintech company. Build a technology company that does fintech. We were going to beat him on fintech. That was, to me, the clarity of the opportunity. Or Drew Houston, who told us of Dropbox, who explained there were these 16 products and why they all sucked.

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

He says, we think we can upend us with technology. So when he came to us, we only gave him one word of advice. Don't build a fintech company. Build a technology company that does fintech. We were going to beat him on fintech. That was, to me, the clarity of the opportunity. Or Drew Houston, who told us of Dropbox, who explained there were these 16 products and why they all sucked.

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

And let me tell you what a great product. Just total clarity. You and I would have understood it. Look, I'm assuming you're a smart guy. I'm a smart guy. Yes, I program a few languages, but you just understood it. You came out of that meeting. Of course, we're going to be investors. It's never something you scratch your head. You have to go to your AI expert and say, what does this mean?

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

And let me tell you what a great product. Just total clarity. You and I would have understood it. Look, I'm assuming you're a smart guy. I'm a smart guy. Yes, I program a few languages, but you just understood it. You came out of that meeting. Of course, we're going to be investors. It's never something you scratch your head. You have to go to your AI expert and say, what does this mean?