Patrick O'Shaughnessy

What is the literal format that you do in your email?

What is the structure that you do personally?

How transparent should one be in that?

As a leader of a business, I can tell you what's top of mind, but a lot of it either might be sensitive or I would worry about scaring people or worrying people about something that I'm thinking about or worrying about.

What keeps me up at night might create stress in the business.

Where should one draw the line in terms of how candid they are?

I want to talk about ads and everything you've learned about building an incredible ads product.

You've built the two most important ad systems in the world.

What business ideas don't work in advertising?

What are the business models that just are doomed to fail?

What would you be worried about if you were one of these fairly monopolistic owners of a massive ad network like the ones we've discussed?

We could throw Uber and Amazon in the mix, Stardash, Facebook, Google.

If you were there running their ads businesses, what would scare you?

There's a new battle happening for that first category, which is a new interface to be owned.

We know ChatGPT does.

I'm curious if you think being the first mover matters to build a new ad network because there's Gemini, there's Anthropic, there's a bunch of people that have tons of users using this new interface.

How do you think about the landscape of the new potential entrance to build the next dominant ad network?

What advice would you give these various parties?

Picking that well, you've talked about like a North Star metric.

What are the attributes of a good North Star metric?