In this episode of the My First Million podcast, host Sam Parr recounts a personal encounter with Ross Ulbricht, the founder of the darknet marketplace Silk Road. Sam describes meeting Ross at a party, discovering that Ross lived nearby, and later learning of Ross's arrest when police swarmed his local library. He explains Silk Road as an eBay‑style platform for illicit goods that generated roughly $2 billion in sales over two years, and notes that Ulbricht allegedly amassed about $10 billion worth of Bitcoin before being seized. Sam also shares how a conversation with Billy Draper (son of venture capitalist Tim Draper) led him to buy a small amount of Bitcoin in 2013, gifting it to family members who later profited when the price rose. The discussion touches on Tim Draper’s purchase of the government‑seized Bitcoin—initially reported as $20 million, later suggested to be in the hundreds of millions—highlighting how this event introduced Sam to cryptocurrency. Throughout, Sam reflects on Ross’s charismatic personality, his alleged attempts at hiring hits, and the broader cultural impact of Silk Road and early Bitcoin adoption.
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Silk Road, and it sold $2 billion worth of merchandise in only 2 years. Okay, so in 2014— my year's maybe off— in 2014, I think, or '13 or '12, I went to a party and I met this guy there named Ross, and he was pretty good-looking and tall, and so he definitely kind of stood out because it was all nerds. And we just started talking and I was flirting with this girl and he swoops in and takes her home. And I was like, Ross, it's us. I started talking to him and friended him online and whatever. And I friended him online.
That's what I do when you win.
Well, I wasn't angry at him because I wasn't angry at him because I was like, damn, he was pretty charming. Whatever. Became friends with him. He turns out he lived— he lived down the street from me. Well, a few months later, I walk home and I walk by the library that I live next door to and there's all these police there. And I go home and find out what happened. And I had heard of this thing called the Silk Road. I'd heard about this. I knew about this for a couple of— about a year or two. And I go home and I look up what happened. They go, Ross got— Ross Ulbricht was arrested and for being the founder of Silk Road. And I was like, explain Silk Road if you don't know what it is. So Silk Road, it's a It was like eBay, but for drugs and murder. And you could buy anything online and use Silk Road. And it sold $2 billion worth of merchandise in only 2 years. And Ross was the sole owner. And now if we look at Bitcoin price, he had roughly $10 billion in Bitcoin that he had made.
And it got seized or he has it. He's in jail.
And so what happened was he was at his library or at the library next door to my house, the Glen Park Library, and he was up stairs on the computer doing deals or whatever, running the business. And the feds had been tracking him, and he tried to kill— like, he hired— he did a couple hired hits, um, jeez, where he tried to get someone killed. And but the person on the other end was an FBI agent, so they went and staged the murders. And he did that multiple times, so he thought he had killed 3 or 4 guys, right? And, uh, when I got home, I looked it up. I was like, holy shit, that's Ross. I know Ross. He was this guy the whole time.
And so you had hung out with him before?
Yeah.
And what was he, a cool guy? Did he say— what did you ask? What do you think?
He was just like, just like, just a guy, just a charming—
like, did you know he ran—
I looked him up on LinkedIn. He said he was an equities trader or like a bank, like some—
technically true.
Yeah. And like, I had friends on Facebook and he was like, hey everyone, I'm selling my truck for $2,000. I mean, when he had tens of millions of dollars of Bitcoin. And I go to my office the next day. I go, I talk to this guy named Billy. I go, Billy, did you hear about this Ross guy, this Silk Road thing? And Billy, his father was Tim Draper.
Right.
And I go, Billy, this thing your dad is talking about, this Bitcoin thing. And he goes, yeah, I saw that. That guy get arrested. He's buying a lot of it. And I was like, should I? And he goes, yeah. And I was like, well, I don't know anything about this Bitcoin thing. But if your dad says to do it, sounds good to me. So I went and bought a little bit of it. And then for each family member that year in 2000, I think it's 2013, I bought like $200 of Bitcoin for each family member as a present. And they all laughed at me. And then a few years ago, when I got to $20,000, they each made like $5,000.
Right.
And that was how I heard about Bitcoin.
That's amazing. And so, so Tim Draper ended up buying all the seized Bitcoin.
I think it was like $20 million worth of Bitcoin.
I think it was more than that, dude. I think it was like in the hundreds. I think it was like $200 million of Bitcoin or something. I don't remember.
I think maybe I think his initial purchase at the time time was $20 million and it ballooned to billions.
I see. Okay.
And he bought it from the government.
He bought it like at a discount, essentially, to the market, right?
I think he paid $20 million, but this is all public. And that is how I found out about Bitcoin.
