Ten years ago, journalist David Kushner got a phone call from a Harvard student asking him to come meet him in the back of a bar in New York City to talk about a fledgling social network called Facebook. When he arrived, he was greeted by a 6’5” blonde rower: Cameron Winklevoss, an identical twin. Winklevoss wanted to tell Kushner about a peer named Mark Zuckerberg whom they claim had stolen their idea for his site.

“At the time when Facebook wasn’t the Facebook we now know, this story was interesting,” he tells me over breakfast in New York this December, “but it seemed like just another pissing match between disgruntled geeks.” Kushner followed the lede anyway, and the Rolling Stone piece that followed brought the story of Facebook’s contested origins to the public.

In his 25-year-long career reporting on the internet, Zuckerberg was just one of many tech icons interviewed by Kushner before they were tech icons: Julian Assange, the makers of Grand Theft Auto, and the creators of Doom and Quake, to name a few. He’s dived far beneath the world of Silicon Valley junkets and conferences to break scoops from the internet’s dark underbelly as well— including a profile of Silk Road’s founder plus features on Anonymous hackers and hactivists fighting for internet freedom and anti-secrecy.

“Last year was the year the internet got caught with its pants down,“ he tells me in a no-bullshit demeanor, as we reflect on a year of tech news that included the fappening, gamergate, a collapse in the value of cryptocurrency Bitcoin, and the Sony hacking. Starting next Thursday, Kushner will bring his deep knowledge of the tech world, hacker culture, internet privacy and secrecy to his new column The Digital Underground for Playboy.com. It’s clear his seasoned perspective is needed more than ever.

Over poached eggs and coffee, we chatted about what he’ll bring to the new column along with the past, present and future of life on the internet.

PLAYBOY: How did you first get your start reporting on the Internet?

KUSHNER: I was part of the Atari generation. I grew up playing video games in Florida. And then in college, I got really turned on to new journalists—Hunter thompson, Tom Wolfe. I booked Thompson to come speak at my college in the early ‘90s and met his agent. From there, I got my first job at the agency, which also represented Timothy Leary, who introduced me to Mondo 2000, an early cyberculture magazine which I started writing for.

PLAYBOY: Mondo 2000?

KUSHNER: It was a beautiful glossy mag made by a bunch of freaks and geeks out in Berkeley. The internet was still very underground then: scientists, government people, deadheads, gamers, hippies, Star Trek fans— an eggheady scene. It was very much a feeling of being in an underground club.

PLAYBOY: How did opportunities to write about tech develop from there?

KUSHNER: There were some guys in New York who wanted to start a BBS or bulletin board system called SonicNet. The idea was to try to do Rolling Stone on the internet, but before there was the web. I got a job with them. This was really, really early. There was no such thing as chat even, but SonicNet’s idea was, “let’s get some musicians, artists, celebrities to come in and do chat.” There was no filtering; it was chaos—like a Reddit AMA in a moshpit. I had to literally explain what the internet was to record labels—”It’s kind of like an interview, but it’s on a computer.” Only progressive, open-minded artists did it. Radiohead came on. David Byrne came on.

PLAYBOY: What were some exciting, early tech milestones that still feel important today?

KUSHNER: I remember when Netscape—the first browser—came out in 1994. That was the holy-shit moment. That was the day that everything totally changed. And that’s when magazines started to get interested. Traditional media was saying ‘What’s going on.” I was an expert by default because I had been in the club that people now wanted to join.

PLAYBOY: How did your career change once old media realized it need to enter the digital era?

KUSHNER: I started a column on digital culture for Spin magazine, and everything kind of rolled from there— articles for Rolling Stone, then my first book Masters of Doom in 2004, which is about the guys who made the seminal shooters, Doom and Quake.

It was the birth of a medium. It’s pretty amazing to have seen that and have been writing about that. It was fortuitous to be there at the right time. Some of the people that I’ve met have gone on to do some really interesting things; some have ended up dead or in prison.

PLAYBOY: How does that perspective and sense of history enrich the work you’re doing today?

KUSHNER: Whenever I see things happening like the Sony hack, or the ‘fappening’ or the success of Flappy Bird, I’m always looking at these things in the context of this greater evolution. I’m thinking about it in terms of what lead up to Flappy Bird: what does this moment in mobile gaming mean? To me, right now is a renaissance for game development in the mobile world that’s similar to the PC world in the ‘90s. It was like indie rock, anybody with a computer could make a game.

Obviously it’s become much more mainstream, but there’s still something very rock-and-roll about it. Anyone can pick up the guitar and play a song; now we live in an age when anyone can sit down at a computer and create the next Facebook or the next Grand Theft Auto— that part of this world is very exciting and will always be exciting.

PLAYBOY: What does it mean to be a hacker in 2015 as opposed to in 1995?

KUSHNER: Today when the average person hears the word ‘hacker’ they think criminal, but really the word didn’t mean that originally—it was just someone who liked to get under the hood of tech. What’s different now, I think, is you kind of don’t need to be a programmer to be a hacker any more. You just need to be someone who can problem-solve and find solutions.

PLAYBOY: It goes without saying that internet culture changes almost too quickly to stay on top of it. What’s next?

KUSHNER: We’re still in the pong years of this new medium. I think it’s really, really early, and I don’t think we have any clue as to what’s ahead. We’re on a very fast trajectory into the ether and we can’t keep up with it —but we can cover the stories, and put them into that larger context, whenever we can.

David Kushner is an award-winning journalist and author of seven books. His articles have been published by The New Yorker, Rolling Stone, New York Times Magazine, and Wired, among others.

His weekly tech column for Playboy.com, The Digital Underbelly, launches Thursday, February 6.