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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]

When one of our partners or associates, they describe a company or the issues facing a company, and the founder comes in the next Monday, and what we heard the week before has nothing to do with what the founder says, that's a huge warning sign. There are many, many things. At the end of the day, you gotta have this spidey sense. You have this amorphous early stage, five, six people.

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

When one of our partners or associates, they describe a company or the issues facing a company, and the founder comes in the next Monday, and what we heard the week before has nothing to do with what the founder says, that's a huge warning sign. There are many, many things. At the end of the day, you gotta have this spidey sense. You have this amorphous early stage, five, six people.

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

Would you really go and spend the next 10 years with them? Not understanding you're investing somebody else's capital and playing the laws of percentages. You know, if I just make 20 investments, two will work. Really not giving a shit about your investors, founders, and so on. Those are the failure modes.

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

Would you really go and spend the next 10 years with them? Not understanding you're investing somebody else's capital and playing the laws of percentages. You know, if I just make 20 investments, two will work. Really not giving a shit about your investors, founders, and so on. Those are the failure modes.

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

Think of Google. Competitive Vantage was architected in a product. Think of many companies. Think of ServiceNow. It was simple workflow. You asked me to do something that you need a PC, it goes to someone, I fill that workflow, I give you a PC. Couldn't be any simpler. Clarity of thought of what the easiest way to do workflow.

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

Think of Google. Competitive Vantage was architected in a product. Think of many companies. Think of ServiceNow. It was simple workflow. You asked me to do something that you need a PC, it goes to someone, I fill that workflow, I give you a PC. Couldn't be any simpler. Clarity of thought of what the easiest way to do workflow.

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

But that got built upon and built upon, built upon, and there's a history of the simple utilities

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

But that got built upon and built upon, built upon, and there's a history of the simple utilities

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

becoming platform because the founder has a vision how to do that so i've seen it both ways look sometimes you build a utility and you're stuck that there's just no way to go but these little seemingly simple utility for which you get purchase orders for which allows you to now have a two-way conversation with a customer what else do you need

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

becoming platform because the founder has a vision how to do that so i've seen it both ways look sometimes you build a utility and you're stuck that there's just no way to go but these little seemingly simple utility for which you get purchase orders for which allows you to now have a two-way conversation with a customer what else do you need

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

These bottom-up things tend to be, for me, way more interesting than these top-down, monolithic, big solution for a million dollars. I like these 25, 30K, quick and solve a point product. Now we've got 100 customers. I love those the best.

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

These bottom-up things tend to be, for me, way more interesting than these top-down, monolithic, big solution for a million dollars. I like these 25, 30K, quick and solve a point product. Now we've got 100 customers. I love those the best.

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

I remember in the days of the consumer type internet, a competitive advantage was a 30-day head start. Competitive advantage was a founder who can run like crazy. So yeah, it's change. It's not always technology. Sometimes it's the first one in. Sometimes there's many late market entrants that have come in and have said, I've seen all the mistakes. So all these rules, you've got to be first.

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

I remember in the days of the consumer type internet, a competitive advantage was a 30-day head start. Competitive advantage was a founder who can run like crazy. So yeah, it's change. It's not always technology. Sometimes it's the first one in. Sometimes there's many late market entrants that have come in and have said, I've seen all the mistakes. So all these rules, you've got to be first.

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

You better write it in pencil. All your principles, ethics, careful due diligence, those get written in pen. But all these other things, competitive advantage, should you build an imperfect product and get to market early? Sure. Should you build a perfect product that takes longer? Sure. If you look at what Steve Jobs did, everything he put in your hands, that was not some rev one cheap shit.

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

You better write it in pencil. All your principles, ethics, careful due diligence, those get written in pen. But all these other things, competitive advantage, should you build an imperfect product and get to market early? Sure. Should you build a perfect product that takes longer? Sure. If you look at what Steve Jobs did, everything he put in your hands, that was not some rev one cheap shit.

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

So there's many ways to heaven. There's many ways. The trick is to understand where you are and break it down to first principle. If I'm selling a hardware software product with a cost of goods to millions of people, I probably don't want a very shitty first product. If I'm selling a simple utility and I need customer feedback, I want to get that out there, especially in the consumer marketplace.

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

So there's many ways to heaven. There's many ways. The trick is to understand where you are and break it down to first principle. If I'm selling a hardware software product with a cost of goods to millions of people, I probably don't want a very shitty first product. If I'm selling a simple utility and I need customer feedback, I want to get that out there, especially in the consumer marketplace.

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

piece of software. I want to get that out as quick as possible, as imperfect as possible, knowing that Rev1 is the wrong product, but at least we're talking. So don't have a textbook.

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

piece of software. I want to get that out as quick as possible, as imperfect as possible, knowing that Rev1 is the wrong product, but at least we're talking. So don't have a textbook.