Nick Bilton

How Silk Road started: a 1600-SAT libertarian who grew mushrooms to prove a point

Nick Bilton recounts how Ross Ulbricht, a smart Austin kid with libertarian ideals about drug legalization, combined the Tor browser and Bitcoin into a proof-of-concept marketplace, then grew his own mushrooms to seed it, and became the biggest drug dealer on the internet.

“And he decides that drugs should be legal, uh, and the government should not be able to tell you what you can and cannot put in your body. And the only reason that the drugs lead to these, you know, to deaths and murder and so on and so forth is because the government has so much control over it. And so he takes The Onion Browser, which is, is the secret browser that you can, uh, where the dark web exists. And then he takes Bitcoin, which both kind of come along around the same time. And he creates this proof of concept, which is this website called the Silk Road.”

Replace research databases with an LLM you can just query

For his new investigative project, Bilton stuffs millions of words of source material into Google's NotebookLM and queries it directly, replacing the Excel spreadsheets and custom databases he used to build by hand.

“What's been interesting is I have this new project that we're doing and we've been using LLM, Google LLMs notebook. And so now we stuff millions of words into these things and I can just query it. Whereas before we had to build like Excel spreadsheets and databases and like, it was very, very complicated the way we did it.”

Steal thisDump all your raw source material into NotebookLM and query it instead of building spreadsheets.

Reconstruct a scene from photo timestamps and GPS math

To write nonfiction that reads like a novel, Bilton geolocates his subject by reverse-engineering photo timestamps: three pics (departure, Golden Gate Bridge, arrival) let him calculate the campground was ~45-50 miles out, find it, sit in the exact spot, and describe the smells.

“One was when he left, and I, we could figure out the street because we could, you know, see the angles and the street signs. The next was when he was driving over the Golden Gate Bridge, and then the third was when he got to the campground. And we could tell timestamps, so we just did the math and we're like, okay, it's probably 45 to 50 miles away. And then we looked in the circle around San Francisco and then we found these different campgrounds and I went to one and there, there we are at the campground.”

Everyone has a reason to talk; your job is to find what they want

Bilton's two-decade reporting lesson: sourcing isn't about breaking news, it's relationships. People always want something (credit, fame, catharsis, revenge), so figure out the motive and give them a reason to talk.

“It's like, it is literally just relationships. And, and what you have to do is you have to figure out— you need these people to talk to you, and you have to figure out how to make them want to talk to you. And so, for example, everyone has a reason.”

Steal thisBefore any cold outreach, ask what this person wants out of talking to you, then offer it.

The best product Jack Dorsey ever made was Jack Dorsey

A Twitter board member's line that Bilton calls the best quote he ever got about Dorsey: everything a founder does is storytelling, and a company's story matters more than its product.

“the best quote I ever got about Jack Dorsey, and I've written a lot about him, was, um, from one of the board members years ago, uh, who said the best product Jack Dorsey ever made was Jack Dorsey.”

The best product Jack Dorsey ever made was Jack Dorsey

A Twitter board member's line that Bilton calls the best quote he ever got about Dorsey: everything a founder does is storytelling, and a company's story matters more than its product.

“the best quote I ever got about Jack Dorsey, and I've written a lot about him, was, um, from one of the board members years ago, uh, who said the best product Jack Dorsey ever made was Jack Dorsey.”

The real origin of Twitter: a stolen idea from Noah Glass

Bilton retells how Twitter actually emerged from an 11-person Odeo hack day where Jack Dorsey pitched 'Status' (an AIM-away-message clone), but Noah Glass reframed it around friendship and the stream, then got pushed out by Dorsey, who later claimed the idea originated when he was a kid listening to fire trucks.

“And so they all start bringing these ideas together and it's truly, it's like 11 people in the room. It, it is a collaboration between all of them. And what Noah has this realization is he's a very emotional guy, very smart, and he's like, it needs to be about friendship. It needs to be about connecting with your friends, and that is what it's about. And so he brought this humanity to it.”

Steve Jobs talked Bilton out of his own story over the phone

A tipsy Bilton took an hour-long call from Steve Jobs that convinced him not to run a story the way he'd planned; days later he replayed it and realized Jobs had killed the correct story. A veteran reporter named it the 'reality distortion field.'

“And so John Markoff, who is a veteran reporter, I told him and he goes, he just says, It's the reality distortion field. And I was like, what's that? And he goes, Jobs, Jobs invented it. And, and every time I would talk to him from time to time, and every time it was the same thing. It was like this, he had this ability to make you believe that what you were doing was not the right story and that this was the way to do it.”

Jobs denied saying something on the record until Bilton checked the tape

At a private New York Times editorial meeting, Jobs flatly denied to Bilton that he'd ever called Apple TV a 'fourth leg' of the stool. Bilton later pulled up the video and confirmed Jobs had said it verbatim, but the whole room believed Jobs.

“Um, and he goes, I never said that. And I was like, no, I'm, I, you know, you said that. I'm pretty sure you said that. And he goes, I never said that. He goes, I've never said that about Apple. Apple Television's an experiment for us. We're just playing with it.”

Jeff Bezos had it all, then threw it away in a midlife crisis

Of all the tech titans Bilton covered, Bezos was the one who seemed to have it all: brilliant, beloved by employees, devoted to family with MacKenzie. Then he divorced and reinvented himself as a bodybuilding 'raver,' which Bilton reads as a midlife crisis.

“And then, uh, and then they got divorced and he ended up, uh, in a very, very different relationship. So I, um, uh, and now you like, he's like this bodybuilding looking like raver. So he, I think he had it all, but for whatever reason he had like this midlife crisis that made him throw it all away. I don't know.”

Jobs and the orange juice: brilliance with no compassion

Walter Isaacson told Bilton how Jobs reduced a waitress to near-tears over pulp in his fresh-squeezed orange juice, justifying it as pushing her to be the best waitress she could be. Bilton uses it to show Jobs paired genius with a lack of compassion.

“And he says, if, if she's chosen to be a waitress for her living, then she should be the best waitress she can be, and it's my job to push her to do that. And it's like, no, you don't know her backstory. You don't know like where her life has gone and why and things like that.”

Don't write about people until you've been written about yourself

Bilton credits a Bill Keller line that changed how he reports: you shouldn't be allowed to write about others until you've been written about. Being on the receiving end taught him to keep compassion while still telling the truth.

“And he used to say, I don't believe people should be able to write about other people until they have been written about themselves. And I learned that when I— people started writing stories about me and I was like, oof, that feels awful. Like, that sucks.”

Steal thisBefore you criticize someone publicly, imagine the same scrutiny aimed at you, then edit for compassion.

The fix for broken media isn't left or right outlets, it's one that holds both

Bilton argues 90% of media is opinionated garbage and the system is broken; the solution isn't a right-wing or left-wing publication but a single place where right, center, and left writers debate respectfully in the same room.

“You need a place where there are people who have right-wing point of views and centrist point of views and left-wing, and they're all in there together and they're debating it and they're respectful of each other. And maybe they disagree, but they are all there. And the problem is the New York Times is all left and the Wall Street Journal is all right and so on and so forth.”

Save the Cat: the page 1/5/30/90 screenplay beat structure

Bilton breaks down the 'Save the Cat' screenwriting template every movie follows: protagonist on page 1, premise by page 3-5, antagonist intro, the turning point at page 30, and the third act by page 90, and argues modern short-form audiences no longer have patience for it.

“Um, by page 3, you have discovered what the movie's about. By page 5, there's the introduction of the antagonist. By page 30, every single movie, if you go back and watch on page 30, which is 30 minutes in, it's the changing moment. It's the, you know, it is the Joseph Campbell, like, this is when the journey begins. And, and then by page 90, you've entered the third act”

Add smells to your storytelling, the trick murder mysteries use

Bilton's biggest takeaway from studying how-to-write-murder-mysteries books: most writers forget to describe smells, but layering in smells, sounds, and textures pulls the reader into the scene far more than plot alone.

“people forget to describe smells, um, and murder mysteries always do. And it's like, and it brings— it really brings you in. It's, it's wild to see how it can add like this extra layer, like sounds, smells, you know, the noises”

Steal thisWhen writing a scene, deliberately add a smell, a sound, and a texture, not just what things look like.

Bitcoin Bonnie and Clyde: the only two people who wanted BTC to fall

Bilton's Netflix doc covers a couple who stole $72M in crypto and tried to launder it, but Bitcoin kept doubling, eventually making the stash worth $8.4 billion at its peak, leaving them as the only two people online rooting for the price to drop.

“This couple that had stolen $5.4— well, they stole $72 million in crypto and then were trying to launder it. And they were the only two people on the entire internet who wanted the price of Bitcoin to go down. And they had— every time they were trying to launder it, it would double and double and double and double and double. And to the point that it was at one point at its peak was worth $8.4 billion.”