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Patrick O'Shaughnessy

๐Ÿ‘ค Speaker
8519 total appearances

Appearances Over Time

Podcast Appearances

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

One of the most interesting investor questions, and I'm curious for your answer from the perspective of a builder and a technologist, is that the degree to which these horizontal model companies are going to destroy

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

or be very bad for old software companies, because over time it will be trivial to spin up your own Slack that has features that you want for your company.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

And it's very reliable in all those same ways that Slack is, and therefore Slack's in a lot of trouble.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

How do you think about that question?

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

Obviously, public markets seem to think software is a lot of trouble.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

The multiples are really, really low.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

How much would you be worried if you ran a good, solid, but older software company today?

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

How do you think about stickiness in this era, just as a general concept, when the friction for creators to build something that new is so low, you can do whatever you want really fast.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

How is anyone going to use anything for a long period of time?

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

You've been so lucky to work for some of the most well-known CEOs and founders of this modern era.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

I'd love the chance to ask you a little bit about each of them and what you learned from them.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

And then more generally, just things you've learned about what great leaders do to run companies.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

But maybe going all the way back to Google and starting with Larry and Sergey, what did you learn from watching them operate and lead?

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

Before we leave Google, you had this interesting idea about communication and Eric Schmidt, obviously another key Google person.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

Can you tell the story about him presenting the company strategy using nothing but images?

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

This is an interesting example of communication.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

Do you remember a specific image?

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

I'm so interested by this exercise.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

It seems potentially productive for anyone to try to jam what they're trying to say into only images.

Invest Like the Best with Patrick O'Shaughnessy
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

And so I'm trying to pin down an image and how you arrived at it.