Obama's tech guru on the TalkTalk hack: 'I put that on the corporation, not the teenagers'
As a kid, Reed explored hacker forums and entertained himself by messing around with code as part of his self-confessed "punkness."
Reed was responsible for Project Narwhal, the highly praised tech infrastructure that got voter information to Obama campaign workers across the country.
Now he's joined PayPal, after his mobile payment startup Modest was acquired by the company earlier this year.
Given his hacker-done-good credentials, I thought I'd ask Reed what he makes of the recent TalkTalk hack that looks like it was carried out by teenagers.
Reed told me on a visit to London this week: "Obviously this is a very nuanced thing because I don't think people should be committing crimes. That's pretty clear.
"But 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."
TalkTalk has been hit by 3 hacks over the past year. The latest, last month, was originally thought to hit all of its 4 million customers, but turned out to affect a little over 159,000 customers.
Reed says: "Security is very difficult. You have to be very careful about security and I think often times people just forget, they don't invest in the right things."
TalkTalk says the hack will cost it £35 million. 3 teenagers and a 20-year-old man have been arrested across Britain and Northern Ireland in connection with the hack.
It looks like those involved in the hack weren't doing it for any malicious or financial reasons, but were trying to show off their skills and earn online "street cred." Reed says he hopes the teenagers involved aren't punished too severely, as he can relate.
He told me: "It really is just about seeing if you can do it. That's why the young hacker story is so complex and hard for people to understand."
"When I was growing up my parents and people that were older than me used to tell me stories of how they basically used to hack cars and build hot rods. That's what they had.
"By the time I was in high school, cars were too complex to really do that do, so you start hot rodding other things - you start playing on the internet and doing interesting things."
Reed has had his own run-ins with the law. In a post on Medium talking about his background in hacker culture, Reed recalls a visit from the Bureau of Alcohol, Tobacco, and Firearms while he was at school, after he told another student how to make a bomb - something he'd learned on an online anarchist bulletin board.
And he tells me: "What's OK is changing as well. Things we were doing in High School probably wouldn't be OK now. We made a video game map of our high school to go and play a death match inside of. It wasn't like we were shooting our students, but could you image? You can see the story right now: 'Kids make 3D model High School shoot 'em up'."
But Reed thinks there's a socio-economic element to a lot of hacker culture that gets overlooked. He says: "One of my favourite books about hackers is Masters of Deception about this hacking group in the 1990s. Many of them didn't come from wealthy families. These are kids that are very intelligent, they just happen to be misdirected."
Rather than punishing teenagers after they do things like the TalkTalk hack, Reed thinks governments and companies should be taking proactive action to encourage talented coding kids to focus on legal activities.
He says: "My parents are very supportive, they helped redirect my technology attitude and my punkness into positive things. If they weren't there, what would have happened? It wasn't like I didn't have those skills. It's about how do we make sure that these kids that are so talented, how do we push them into the right space."