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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]

No, you have to share the dough appropriately. And in my case, I never called us a family. I thought family's bullshit. I've got members in a family I have to endure forever. Can't get rid of them. I told people we are high performance and pick your nouns. We're a performance team. If you don't believe in sports, production, a movie, and maybe the investors are the actors.

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

No, you have to share the dough appropriately. And in my case, I never called us a family. I thought family's bullshit. I've got members in a family I have to endure forever. Can't get rid of them. I told people we are high performance and pick your nouns. We're a performance team. If you don't believe in sports, production, a movie, and maybe the investors are the actors.

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

Maybe the investors are the goal scorers. But you know what we need? We need trainers. We need coaches. If you're a movie, we need a director, a producer, a makeup artist. And it takes everybody. And so just believing internally. That's what we need.

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

Maybe the investors are the goal scorers. But you know what we need? We need trainers. We need coaches. If you're a movie, we need a director, a producer, a makeup artist. And it takes everybody. And so just believing internally. That's what we need.

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

And incorporating into the investment business into what I think is the most fabulous culture of any partnership in the investment area is really our secret sauce.

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

And incorporating into the investment business into what I think is the most fabulous culture of any partnership in the investment area is really our secret sauce.

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

Well, first of all, in my opinion, it's gone from a high margin cottage industry to a lower margin mainstream business. And when you see that, you see all types of peoples coming in. You start having all these cycles, momentum cycles, down cycle. In a momentum cycle, you hear things from people that have never made a dime, don't know what they're doing. Raise as much money as you can.

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

Well, first of all, in my opinion, it's gone from a high margin cottage industry to a lower margin mainstream business. And when you see that, you see all types of peoples coming in. You start having all these cycles, momentum cycles, down cycle. In a momentum cycle, you hear things from people that have never made a dime, don't know what they're doing. Raise as much money as you can.

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

Screw the venture guys. Give them as little equity as you can. And without being self-serving, I think those are the wrong types of messages. The messages are raise as little money as you can to get to the next milestone. Find an investor in the same way you'd find an engineer. It's not, I just got a term sheet.

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

Screw the venture guys. Give them as little equity as you can. And without being self-serving, I think those are the wrong types of messages. The messages are raise as little money as you can to get to the next milestone. Find an investor in the same way you'd find an engineer. It's not, I just got a term sheet.

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

Achieve balance on your board and your company so that you are in some ways a force to behave correctly. And in the momentum cycles, and we've seen them before, whether it was 97 to 99 or 6 to 08 or 20 to 22, all these horrific habits got involved where CEOs wanted, I want to be a unicorn. And venture guys were fighting all over, that were stepping over their feet to try to do that.

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

Achieve balance on your board and your company so that you are in some ways a force to behave correctly. And in the momentum cycles, and we've seen them before, whether it was 97 to 99 or 6 to 08 or 20 to 22, all these horrific habits got involved where CEOs wanted, I want to be a unicorn. And venture guys were fighting all over, that were stepping over their feet to try to do that.

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

And what we have right now is a bit of a shit show. You know, a whole bunch of companies. There's companies with 500 million in the bank. A billion in the bank, I heard of one. with maybe an $80 million run rate and no growth perspective. They don't know what to do. Bad habits all over the place. And that's what happens during, quote, wonderful time. All these lousy habits are built.

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

And what we have right now is a bit of a shit show. You know, a whole bunch of companies. There's companies with 500 million in the bank. A billion in the bank, I heard of one. with maybe an $80 million run rate and no growth perspective. They don't know what to do. Bad habits all over the place. And that's what happens during, quote, wonderful time. All these lousy habits are built.

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

You're in times like these, Where I'm much more optimistic, you have real founders coming out. There's a lot more balance between investors and founders. That helps founders. It doesn't hurt founders. There's still people that are willing to invest. Now it's AI. We'll invest in AI.

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

You're in times like these, Where I'm much more optimistic, you have real founders coming out. There's a lot more balance between investors and founders. That helps founders. It doesn't hurt founders. There's still people that are willing to invest. Now it's AI. We'll invest in AI.

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

There is a lease in the water, a little more of a restraint, a little more thought process of who do I want to bring as my next 10-year partner? Not, I got a term sheet last Thursday. Very different. Got a term she likes Thursday is I walk into a bar and the first male or female that talked to me, I got married.

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

There is a lease in the water, a little more of a restraint, a little more thought process of who do I want to bring as my next 10-year partner? Not, I got a term sheet last Thursday. Very different. Got a term she likes Thursday is I walk into a bar and the first male or female that talked to me, I got married.

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

As opposed to, no, I met and dated someone for a year, six months, or whatever it is, or three months. Got to know them a little bit. I decided our value system was going to be aligned. We decided to get together and build a company. These are much healthier times. And like everything else in life, reality is usually the opposite of what it seems. Tough times, healthier times.

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

As opposed to, no, I met and dated someone for a year, six months, or whatever it is, or three months. Got to know them a little bit. I decided our value system was going to be aligned. We decided to get together and build a company. These are much healthier times. And like everything else in life, reality is usually the opposite of what it seems. Tough times, healthier times.