HARPER REED

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.

The advice I used to give to engineers I hired was, 'Don't eat the pizza.' Sometimes when you walk into these high-pressure environments, it's, like, doughnuts everywhere and all these little cakes.

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.

When you go from building T-shirts to software for a presidential campaign used by a cast of millions, it's pretty easy to think, 'OK, we can build something pretty big.'

A lot of people are buying things on the Internet - not just white men.

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.

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.

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.

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'm not a very patient person in general.

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

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

One of the things that I used to make sure I'd do was to always make sure I'd have dinner at home because I needed that disconnect from work. Even when it was crazy, I'd go home at, like, 10 o'clock and have dinner. That way, I had time where I could decompress a little bit and then go back in.

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.

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

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.

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

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.

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.

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.

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?'

I don't drink coffee; I drink a lot of green tea and water.

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

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