People are building apps that are doing super-crazy things, and there's a lot of talk about modeling and microtargeting. Facebook can predict when people are going to break up, and Target is able to predict if a woman is pregnant before she knows just based on the type of lotion she bought.

The first thing is - and this is very important - I support the unmonitored use of the Internet for everyone. It doesn't matter what country you're in or what you do for a living - everyone should have the right to an unmonitored Internet.

We developed our product called Dashboard, which was a software tool that was designed to be a virtual campaign office to help volunteers communicate and collaborate through emails and interacting online. It was our attempt to take an offline field office and merge it online.

What I do think is important is this idea of a 'privacy native' where you grow up in a world where the values of privacy are very different. So it's not that I'm against privacy but that the values around privacy are very different for me and for people who are younger than my parent's generation, for whom it's weird to live in a glass house.

PayPal's been around forever. How do we use that platform to solve the future of commerce?

I wonder which is ultimately more creepy: shopping at Amazon or using Facebook?

'Data scientist,' as a profession, is largely a fad.

Myself, I have a philosophy degree and a fake computer-science degree. I say fake because I really didn't learn anything.

I usually hire people who have very exemplary work experience. Where they went to school, or what degree they have, really has no play into the hiring decision.

If there's a wall, we break it down and go through it.

I spent a lot of time hacking, doing all this stuff, building websites, building communities, working all the time, and then a lot of time drinking, partying, and hanging out. And I had to choose when to do which.

Not every time you open Messenger do you want an Uber, but when you do want an Uber, it appears. That is the goal.

In technology startups, there's a lot of winging it.

I can only speak to the Democrat side, but for the Democrats, everything is aggressively measured, and what that means is if you're going to use Snapchat, you're going to use it for a reason, not just for fun.

My career choice has largely been what I wanted to do. I always knew that technology would be one of the threads.

I would still describe myself as a hacker. I still remember feeling the magic, the sense of discovery, when I first connected to a bulletin board. It seemed like the world was somehow brighter, the greens were greener. Like I'd stepped through a portal to the other side. I knew back then that things would never be the same again for me.

There are a lot of people who are unable to take a break to clear their minds. I imagine they are the ones who need it the most.

Chicago's a flyover city. I don't think we should try to change that. But it would be really cool if we had a little more opportunity for investors to come hang out.

Photo management software is terrible. Mylio is pretty good - but disrupts the 'natural' flow of things: i.e. Apple Photos.

Taking time to do something slower than you normally would is a privilege that should not be ignored.

It was on a bulletin board that I first learned about hacker culture, the 'Let's just break through this wall and see what's on the other side' mentality.

There is the egoism of technologists. We do it because we can create. I can handle all of the parameters going into the machine, and I know what is going to come out of it.

If you want to go and build a company that exists in Silicon Valley, then you should go and do it there. But if you want to build a company that is Australian, that represents your culture and your being, then you should do it in Sydney.

We were orbiting around the idea of intent and context. We would take the bus into work, and if you said, 'Here's a shirt you might like,' and I open it on my mobile phone, I'm not going to pull out my credit card and wallet. We thought, 'How does someone do this? An e-mail to yourself, or you try to remember?'