Nick Bilton

Nick Bilton

Special Correspondent, Vanity Fair. Author of upcoming "AMERICAN KINGPIN"

THIS CHAT HAPPENED ON May 11, 2017

Discussion

Nick Bilton
Nick Bilton@nick_bilton
Hi - I'm Nick Bilton, Special Correspondent for Vanity Fair and bestselling author of HATCHING TWITTER. I recently wrote AMERICAN KINGPIN: The Epic Hunt for the Criminal Mastermind Behind the Silk Road, a true-life thriller about the rise and fall of Ross Ulbricht, aka the Dread Pirate Roberts, the founder of the online black market Silk Road. Through thousands of hours of research and interviews and millions of words of documents and chat logs, I was able to tell the complete story of Ross and the rise and fall of Silk Road. It all started when a 26-year-old libertarian idealist and former Boy Scout, launched "a website where people could buy anything anonymously, with no trail whatsoever that could lead back to them." He called it Silk Road, opened for business on the Dark Web and was christened as the Dread Pirate Roberts. The site grew at a tremendous pace, soon processing hundreds of millions of dollars in sales of drugs, hacking software, forged passports, guns, grenades, poisons and possibly even people's body parts. I'm delighted to be here--ask me anything!
Matt Mayberry
Matt Mayberry@mattmayberry · Hacking Human Behavior at @BoundlessAI
Hi Nick. I love your pieces in Vanity Fair. Did you get any indication that Ross had an endgame for the Silk Road? Was their a certain amount of money he wanted to bank or achievement he wanted to reach? With all the money he had made, why keep running it?
Nick Bilton
Nick Bilton@nick_bilton
@mattmayberry I don't think it was ever about the money for him. He was caught with tens of millions of dollars in Bitcoin on his laptop and thumb-drives, and yet he was living in a 1,200-a-month apartment, was wearing the same clothes his girlfriend had bought him 5 years earlier in college and had $2 — yes, two dollars — in cash in his pocket. From all of his writings that I've read, I think his end game was really that he believed he could win the War on Drugs.
Priscilla Burch
Priscilla Burch@d_no_vator · Founder/CEO - Fun Club
Hi Nick, I want to give "special thanks" to you for writing one of my first books I've read to jump start my knowledge of the startup world, which I believe EVERY entrepreneur (especially in the tech world) should read. That book in particular gave me a gory sneak peek into how backstabbing, conniving and cut-throat people can really be INSIDE of the business, the things that the outside world may never see or see when things have already hit the fan. So thank you for that!!! I could ask you things about your current positions as a Special Correspondent for VF, being a best-seller of Hatching Twitter and now American Kingpin, yet what we all as people tend to overlook as we are on about our day, kicking ass and knocking things out the park...is to ask how the heck a person is doing. So Nick, how the heck are YOU doing? How's life treating you? And what advice do you personally have for an African-American, Female Founder & CEO, in Tech? Congrats on ALL your accomplishments and best wishes in your future endeavors! Best, Priscilla
Nick Bilton
Nick Bilton@nick_bilton
@d_no_vator Priscilla, thanks for the lovely introduction! I'm good and very excited to talk to more people about American Kingpin. As for how I'm doing — thanks for asking — I'm exhausted. But, another cup of coffee should solve that problem.
Priscilla Burch
Priscilla Burch@d_no_vator · Founder/CEO - Fun Club
@nick_bilton You bet! And I will definitely check American Kingpin out.
Nick Bilton
Nick Bilton@nick_bilton
@d_no_vator The chaos and drama in American Kingpin will make Hatching Twitter seem like reading about a game of bingo at the local rectory. (In other words, I think you'll like the new book.)
Priscilla Burch
Priscilla Burch@d_no_vator · Founder/CEO - Fun Club
@nick_bilton I love those type of reads, so I'm sure I'll enjoy it!
Emily Hodgins@ems_hodge · Operations @ Product Hunt
Hi Nick, thanks for joining us today. What is your writing process?
Nick Bilton
Nick Bilton@nick_bilton
@ems_hodge My writing process is similar to the way I write news articles, columns and magazine features. I report, report, report, talking to as many people as possible about the subject I'm working on, and gathering as many details as I can (in the case of the Silk Road, this included photos, videos, chat logs, diaries, social posts etc.) and then gathering everything into one place. I actually do a fair amount of writing in my head before I stick anything on paper (well, on my screen to be precise). Then, when I'm finally ready to write, I just let it pour out of me. For example, with American Kingpin, I probably spent 2 years reporting the book and thinking about the structure, and then about 4 months actually writing it.
Jacqueline von Tesmar
Jacqueline von Tesmar@jacqvon · Community at Product Hunt ⚡️
What's the best advice you ever received and how did this impact you?
Nick Bilton
Nick Bilton@nick_bilton
@jacqvon This is a great question. Some years ago, I was struggling with what I wanted to do with my career, and a friend said: "Imagine where you would like to be in 5 years and then work backwards to figure out how you got there." It was probably the smartest advice I've ever heard.
Theoharis Dimarhos
Theoharis Dimarhos@theo_dimarhos · Marketing+Biz Dev at AngelouEconomics
Nick, what have you found to be the best tips on interviewing someone and to get them to open up?
Nick Bilton
Nick Bilton@nick_bilton
@theo_dimarhos More often than not (especially with books) sources want to ensure that the record is going to be accurate and the truth will be out there, and I think it's a matter of convincing them that is the case. Sometimes, in order to get someone to talk, I divulge what I know, almost like putting all my cards on the table and hoping they do the same.
Theoharis Dimarhos
Theoharis Dimarhos@theo_dimarhos · Marketing+Biz Dev at AngelouEconomics
Nick, what have you found to be the best tips on interviewing someone and to get them to open up?
Brendan Beirne
Brendan Beirne@brendanbeirne · Product / strategy, Joojoo
Where do you see dark web shenanigans going over the next five to ten years? Does it become a larger / more influential part of the internet, or does the cybersecurity community get a handle on it?
Nick Bilton
Nick Bilton@nick_bilton
@brendanbeirne It's already larger! There are countless new websites out there on the Dark Web for drugs and weapons and hacking tools. The difficult part for authorities in the U.S. is that the biggest sites are believed to be located in Russia and Asia, which means the Feds can't do much to stop them unless foreign governments assist. 10 years from now, as technology pervades even more areas of our lives, I think it's only going to be more difficult to track.
Velina Ivanova
Velina Ivanova@velinaivanova
How did your opinion of Ross Ulbricht change as you were getting to know more about him and his motivation for creating the Silk Road?
Nick Bilton
Nick Bilton@nick_bilton
@velinaivanova My opinion of Ross definitely changed through the reporting process. There were so many people who knew him in the real world who said he was altruistic, kind and compassionate, which I think remained true (and still does). But the people who worked with him as the Dread Pirate Roberts on the Silk Road, saw him morph over they years he ran it, eventually changing as he became so powerful, and that power blurred his ability to see how the site he had invented was harming people, in addition to helping them.
Emily Hodgins@ems_hodge · Operations @ Product Hunt
What are your top tips for someone who wants to start a career in writing?
Nick Bilton
Nick Bilton@nick_bilton
@ems_hodge 1) Read. Read. Read. I am a voracious reader (mostly fiction books) and have learned so much about style, writing, and form by devouring other author's great novels. 2) Don't be afraid to just write and publish something. There are people who get so caught up in the tiny details that they never finish anything. Nothing is every going to be finished, there's just going to be a version of it that you show other people.
Craig Snowdon
Craig Snowdon@snowyislington · Head of Business Development, Abintegro
What surprised you most about writing this book?
Nick Bilton
Nick Bilton@nick_bilton
@snowyislington I think the thing that surprised me most was how Ross's website (and management style) was so similar to other startups I had written about in Silicon Valley. He had read the same books most of the successful CEOs read, he had the same unquenchable drive to see his product succeed (even ordering "hits" — or so he thought — on people who stood in his way) and in the same way Google and Facebook offer perks to their employees, Ross did too, giving them bonuses and organizing movie nights and book clubs. The major difference, of course, is that those other CEOs decided to disrupt the taxi, hotel or communications industries; Ross went after illegal drugs.
Ben Tossell@bentossell · newCo
What is something that you believe in that others might disagree on?
Jake Crump
Jake Crump@jakecrump · Community Team with Product Hunt
What's your morning routine?
Nick Bilton
Nick Bilton@nick_bilton
@jakecrump My morning routine *used* to be: wake up at 6am, quickly check my email (but don't reply to any), have two cups of coffee and write 1,000 words before 8am. Now, my morning routine is: wake up at 6am, get my 2-year-old son out of bed, change his diaper, help my wife with the other baby (3 months old), make breakfast, and spending the rest of the morning changing diapers and ensuring the 2-year-old doesn't attack our dog, stick something into a wall outlet. I don't get to start writing until about 10am now, but I love my new morning routines.
Seth Williams
Seth Williams@sethbwilliams · Designer, Product Hunt
What is your definition of success?
Nick Bilton
Nick Bilton@nick_bilton
@sethbwilliams Do work that fulfills you. It doesn't matter what it is, just something that makes you feel proud. (And it's not about how successful that work is perceived by others, because if it is you'll feel great by the highs and sad by the lows, so it's much more about the process and growing at a skill.) Most importantly though: family and friendships.
Jake Crump
Jake Crump@jakecrump · Community Team with Product Hunt
What is your most used app?
Nick Bilton
Nick Bilton@nick_bilton
@jakecrump Oooh, good question. It used to be Twitter, but I delete it from my phone on a regular basis because it's such a time-suck. Probably in this order: iMessages, Instapaper, Kindle, Camera, Podcasts and Audible. (You?)
Sachin Benny
Sachin Benny@sachin_benny
Hey Nick, What advise do you have for an aspiring entrepreneur moving to the United States at the age of 25? P.S: Loved your article on Vanity Fair "Why HollyWood as We know is over", which is how I came to read a lot of your work