I grew up in Greeley, Colorado, in a house without a television set. I was a very nerdy kid: I used to play 'astronaut' and eat bouillon as astronaut food. We also had tons of books.

I've had a lot of bosses that I didn't agree with, but the worst boss was very much me myself. So, I can't let myself slack off, and if I do slacking off, I'm the one that's yelling at myself. I've worked with a lot of different employers, and none of them have been as aggressive as I have been.

The opportunity to step away from everything and take a break is something that shouldn't be squandered.

The team that I had built was all white dudes with the same perspective on things that was at times comfortable and easy, but we weren't as innovative as our competitors.

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?'

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.

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.

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.

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

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

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.

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.

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.

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

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.

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

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

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.

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

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.

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

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

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

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

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.

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.

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.

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.

Our goal is to solve a problem for the retailer, not to solve a problem for my ego - which is big.

I find that I often forget that people come from all over. In interfaces, products, experiences, and building for people, we always forget that people are not us.

When I give talks, I often quote from a button I received at a Google event: Always Be Creative. I use it to illustrate how important creativity is in technology and business.

I want to involve creativity more in technology and business. It is obvious that for us to be successful, a healthy relationship with creativity is needed.

Advice is always awesome because it never makes any sense when you compare it all together. It always contradicts other advice. I love advice.

Instagram is amazing, and I enjoy sharing photos there. However, I don't think it is where my photos will go to live.

The thing about Snapchat is it is ephemeral, so you don't - it's not like a video that you post to YouTube and then everyone can see it. It's this video that you get to share this kind of very intimate experience again, this very kind of genuine experience with another person in a more one-on-one sort of way. And I really appreciate that.

We see these wonderful apps that really have changed our world in many good ways such as Uber or Airbnb, but at the same time, they're drastically changing the workforce. And they're changing them so much that the industries themselves are not able to keep up.

I programmed computers every day. And one of my favourite apps we built was this thing called Awesome Updater, that all it did is send you a tweet randomly that was like, 'Yo, you're awesome.'

When you have a good vision and a very large capability of impact, that's very powerful.

When you read Trump's tweets or see candidates interact online like Jeb did with Hillary, you're like, 'Yes, it's just like my friends.' That's the magic.

If you get a WhatsApp message, you're probably going to open it. That's the interesting thing.

Startupfest is a very positive conference. I think a lot of it has to do with how different culturally it is from other startup or tech conferences.

I never would wish technology failing on any sort of opponent or enemy.

TechStars offers a network, and being a part of that network is an awesome opportunity.

If there's one thing about Chicago, we take care of our own.

My entire career has been based around commerce. The Obama campaign was famous for raising boatloads of money online. My question is how do you make conversions better through mobile and e-mail.

All of this conversation about chat and assistance lays the groundwork for what I would look at as the future of commerce.

I really think we have a future ahead of us where chat is obviously a big part of it, but I don't think the context of having that little assistant in your pocket is necessarily the only place where it will be.

Crowdsourcing is the future. However, if you don't trust your users to build/create/upload awesome work, they won't trust you with their crowd capital.

We didn't want to waste time by sending our volunteers to Republicans; we sent them to the undecided.

Presidential campaign and White House are two aggressively separate things. They still think I'm the weird kid in the corner, so I don't have much power. But I'll definitely do something to help.