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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]

Simplicity, crystal clearness, something a mere mortal can understand. If you can't describe it and you can't understand it, you're out to lunch. Singularity of purpose. When I go to the store, I buy a pencil because I want to write. I don't buy a pencil because I want to write. I scratch my back with a tip. It doesn't work like that.

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

Simplicity, crystal clearness, something a mere mortal can understand. If you can't describe it and you can't understand it, you're out to lunch. Singularity of purpose. When I go to the store, I buy a pencil because I want to write. I don't buy a pencil because I want to write. I scratch my back with a tip. It doesn't work like that.

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

Singularity of vertical market early on because you want to be narrow. You have no resources. You've got to be narrow. Oh, we're chasing these four vertical markets. It sounds good. But in order to do that, you have to have marketing that talks four different languages for four markets. And maybe you have to have engineering that develops different features for every market.

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

Singularity of vertical market early on because you want to be narrow. You have no resources. You've got to be narrow. Oh, we're chasing these four vertical markets. It sounds good. But in order to do that, you have to have marketing that talks four different languages for four markets. And maybe you have to have engineering that develops different features for every market.

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

A little company can't do that. So be at the bullseye as sharp as you can and then start to expand in concentric circles when you get your legs under you in that vertical market. That's what I look for in positioning.

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

A little company can't do that. So be at the bullseye as sharp as you can and then start to expand in concentric circles when you get your legs under you in that vertical market. That's what I look for in positioning.

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

So keep in mind that we as board members, our job is to make these founders very capable and successful. You lose the founder, you lose the soul of a company. There's no question about that. And telling the founders cuts a little bit of the pinky. And you want a founder with 10 fingers and 10 toes.

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

So keep in mind that we as board members, our job is to make these founders very capable and successful. You lose the founder, you lose the soul of a company. There's no question about that. And telling the founders cuts a little bit of the pinky. And you want a founder with 10 fingers and 10 toes.

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

But there are certain times where the thing is off the rails, that it's worth a small piece of the pinky to get back in the right direction. First, what I try to do, instead of telling, I like showing. So let me give you an example. Your VP of marketing stinks. If I say that, it means nothing to a founder. But if I say, I'd like you to meet these three VP of marketing from other companies.

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

But there are certain times where the thing is off the rails, that it's worth a small piece of the pinky to get back in the right direction. First, what I try to do, instead of telling, I like showing. So let me give you an example. Your VP of marketing stinks. If I say that, it means nothing to a founder. But if I say, I'd like you to meet these three VP of marketing from other companies.

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

Let me tell you what happens nine times out of 10. They come back and they say, holy shit, the guy we have or the gal we have is nothing like this guy. Duh. So try to show, not tell. Build trust, which doesn't get built day one. It really gets built with the first time the CEO founders in a pinch and he understands you're there to help him out.

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

Let me tell you what happens nine times out of 10. They come back and they say, holy shit, the guy we have or the gal we have is nothing like this guy. Duh. So try to show, not tell. Build trust, which doesn't get built day one. It really gets built with the first time the CEO founders in a pinch and he understands you're there to help him out.

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

So once you have trust, which is really the foundational layer, it's the grease that makes all business runs. And once the founder understands maybe you have a little experience, a compliment is incredible talent. And once you show the founder without telling the founder, and once in a while you have to tell because maybe you don't have the time to show, but you better do that once a year.

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

So once you have trust, which is really the foundational layer, it's the grease that makes all business runs. And once the founder understands maybe you have a little experience, a compliment is incredible talent. And once you show the founder without telling the founder, and once in a while you have to tell because maybe you don't have the time to show, but you better do that once a year.

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

It's very rare. That's what you do. Those are the actions that you take. And you want to come out of that in a win-win. You want to come out of that with an enlightened founder who's extremely happy and better in his role rather than having achieved your goal of a new VP of marketing where the founder feels like his knees were cut off.

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

It's very rare. That's what you do. Those are the actions that you take. And you want to come out of that in a win-win. You want to come out of that with an enlightened founder who's extremely happy and better in his role rather than having achieved your goal of a new VP of marketing where the founder feels like his knees were cut off.

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

Well, the first thing to understand, is it a broad product? Is it a widget? If you have a widget, it's simplicity. If you have a widget, you do less account-based management. because you've got 10,000 accounts that you can call. So that becomes a volume play. You build something a little more complex with a little more of a solution cell versus a widget cell. A pencil is a widget.

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

Well, the first thing to understand, is it a broad product? Is it a widget? If you have a widget, it's simplicity. If you have a widget, you do less account-based management. because you've got 10,000 accounts that you can call. So that becomes a volume play. You build something a little more complex with a little more of a solution cell versus a widget cell. A pencil is a widget.

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

A solution is you've got to tell a story. Fewer accounts, you better have your story right per account. So you have to understand what that is. You have to make a guesstimate of what percentage of your leads comes from BDR versus salespeople. I will tell you that early on, it's a Rolodex of the salesperson. First, you got to make those decisions.

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

A solution is you've got to tell a story. Fewer accounts, you better have your story right per account. So you have to understand what that is. You have to make a guesstimate of what percentage of your leads comes from BDR versus salespeople. I will tell you that early on, it's a Rolodex of the salesperson. First, you got to make those decisions.