This idea of, there's a locked door; how do you open it? You don't necessarily care what's behind it; you're just more excited about opening the lock... It's not about finding the treasure; it's more about defeating the puzzle.

You can tell charlatans when they say 'big' in front of everything.

Very smart people are often tricked by hackers, by phishing. I don't exclude myself from that. It's about being smarter than a hacker. Not about being smart.

Before I was hired by Obama's team as the CTO for his 2012 re-election campaign, I had certainly never been involved with anything of that nature before. Yet, I somehow knew I could do the job. I attribute that confidence to my experience as a hacker and the subsequent willingness to take risks.

In the U.S., it's all about turnout, which means you have to appeal to every single Democrat to get them to vote.

Mobile usage is going up; mobile conversion is not.

Data is what powers all of us and our lives. It is ubiquitous among our now-connected lives. I love how it is now the oxygen of our Internet world.

I try and wake up relatively early. I listen to some music and check Twitter. I also make sure I weigh myself and check how long I slept. I do that because knowing that data seems better than not knowing it.

I think there are a lot of hurdles between a normal consumer brand figuring out their mobile strategy - let alone their chat app strategy - and programming a Facebook Messenger chatbot.

When you walk into a field office, you have many opportunities. We'll hand you a call sheet. You can make calls. You can knock on doors, and they'll have these stacks there for you. They'll say: 'Harper, you've knocked on 50 doors. That's great. Here's how you compare to the rest of them.' But it's all very offline.

First of all, a giant corporation probably shouldn't be being hacked by teenagers. I put that on the corporation, not the teenagers. Teenagers are going to do what teenagers are going to do - rebelling. But if they're able to hack a big corporation, that seems like the corporation should be better at security.

The digital team who were running Twitter, they weren't just going to put out a tweet for fun. They're going to try and figure out how do we measure the impact. Then they'd tweet it, and if it worked, great.

Oftentimes in tech, people think, 'I'm the only one that has this.' I call them the Atlas People. They're like, 'The weight of the world is on the shoulders. I'm the only person who can solve this problem.' But you can't do that.

Google Photos is great. I enjoy using it to curate my photo collection online. The integration on iOS to Apple Photos is a bit too much voodoo for me.

Books have literally powered most of my life. Whether as a stress relief when doing hard things or as vacation fodder, they are a constant and important part of my life.

I'm not a very patient person in general.

I am patiently waiting for the singularity.

We are often celebrating technology and codes, but we don't really think about the creative side.

When I called people and said, 'Hey! Do you want to work for the president?' they usually said yes. I had 2 people say no. One person said no because they were a Republican; one person said no because they're a Libertarian.

I have to say that you don't really know stress until you know that the path of the free world is resting a little bit on your shoulders.

I'm a white male in power. In many cases, I'm the enemy.

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.