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

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

" 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. "

" 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. "

" 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. "

" 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. "

" The information diet of a senior campaign staffer is insane. We were all addicted to our chosen email delivery devices and were aggressively tethered to them. It made sense and wasn't an issue during the campaign because of the importance of the situation. However, once the campaign was over and we were successful, the information flow dried up. "

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

" 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. "

" 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?' "

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

" 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. "

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

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

" 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. "

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

" 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. "

" 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. "

" 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. "

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

" The main ideas for us are scale, stability, and audience. "

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

" 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. "

" When I look for new books, I often struggle to find things that challenge and entertain me. This has caused me to spend a number of cycles thinking about where I can get the serendipitous book discovery experience that we had in physical book stores. "

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

" 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. "

" I would say Silicon Valley and New York have inflated salaries. "

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

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