Waiting To Be Signed · interviews on generative art, on-chain
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Interview // SEP 2025

Jammasterlee

Title: Can't Live A Normal Life
Role: Generative artist
Duration: 51m
Hosts: Will & Trinity
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#078 · Can't Live A Normal Life
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Will: All right, hello and welcome everyone to a very special episode of Waiting to Be Signed. I'm joined today by Steven Lee, also known as Jammasterlee on TikTok and Twitter. A lot of you listening probably won't know who he is or why he's on the show, so I'll throw it to Steve right away to tell us who he is. Give us an introduction.

Jammasterlee: What got me on the map, so to speak, was a fateful, crazy decision I made around 2020, during the rise of Bitcoin's third bull run. I basically said, fuck it, I'm going to quit my job. I was disgruntled — actually, it's more profound than that, but we'll get into it. I threw everything away and plowed it all into Bitcoin at once. I ran into this kid who convinced me, and he was super into leverage. So my whole life went triple-leveraged onto Bitcoin, which meant that if it dropped more than 30%, I'd lose everything, but if it didn't, I'd cash in big. That post went viral-ish, at least within that crowd, and I built a pretty good niche following for a bit. I tracked everything — that's probably the one thing I did right during that bull run, keeping that diary going so people could watch it all happen in real time.

Will: I found you on TikTok, probably some of your earliest posts, right around when I was starting to get interested in crypto myself. I don't know how the algorithm worked, but it started showing me your stuff — we were also geographically close, since I was living in Brooklyn at the time. I got immediately intrigued and caught up in it. That earliest phase of your account was probably the biggest in terms of engagement, right?

Jammasterlee: Yeah.

Will: Tell us a little about your background before TikTok, and why you decided to put it all out there. Had you even known much about crypto or Bitcoin before meeting that kid?

Jammasterlee: I knew nothing about Bitcoin. I've been reviewing my TikToks, and there's a video a couple months in where I'm on camera saying, "I actually know nothing about Bitcoin" — this is after I'd already put all my money into it. I wouldn't say I was a working stiff exactly, but I was selling insurance. I've always liked doing my own thing, always wanted to find a way to hack the whole income question. In insurance you generate renewal income and you're kind of your own boss, so I did that for a while. It was challenging, interesting — a little bit countercultural, honestly. I was sort of the bad guy in it, and I liked that role. I did a good job, but at some point it turned on me. I started to hate it, and it got into my bones. I was telling a friend the other day that at one point I was diagnosed with pneumonia, shingles, and Crohn's at the same time, and the only thing that got me through it was weed butter, I swear. I was miserable, and it was killing my body.

After about ten years of that, I was so broken my sister said, "Dude, you have to quit. You need to change something." She'd seen a couple of my breakdowns — it made her cry once, just watching my body give out on me. So I moved to New York City, where she was living, and during the height of COVID I went to a singles event because there was nothing else to do. I didn't even expect to meet girls — I just figured there might be some other desperate guy there I could become friends with. I just needed friends. That's when I ran into Bitcoin Bill, and that's how the ball started rolling.

Will: What about TikTok itself — why did you decide to document it, and did you have a plan? Your earlier videos do seem like you were leaning into being a lifestyle or content creator. And you're now working on editing all of it into a larger project.

Jammasterlee: Right, that's the art piece.

Will: That's the art piece — so there is art here. This is an art podcast, so there's an art component to this.

Jammasterlee: Disqualifies.

Will: There were points in the earlier content where it seemed like you were trying to lean into being a content creator — there's an episode where you interview someone on the street. Was that just a plan that evolved as it went? I also remember you mentioning a passion for film in your earlier videos. Was that part of the plan with the whole Bitcoin move?

Jammasterlee: I'd been doing some filming a few years prior, but I could never quite make up my mind — it felt like such a scary thing to jump into, and I'm the kind of person who, if I do something, I fucking do it. I need to sink my teeth into something to get into it. I'd done street interviews before — I love doing interviews, like what you're doing right now. I fucking love it, especially spontaneous ones. There were a couple of times I thought, this is my life's calling, but I couldn't quite follow up on it.

When I did the Bitcoin thing — I should explain how he sold me on it. Bitcoin Bill had two phones, this hardcore trading guy, showing me both of them: "Yeah, I made $300,000 yesterday." Then he tells me, "I had a dream. I came back from the future to tell you Bitcoin hit $300,000 in 2027." And I was so hungry for something magical, transcendent, fantastical — because my life was just selling insurance: "Hi, do you have disability insurance? Have you thought about what might happen if you get injured?" Ten hours a day of that. So I was like, fuck it, I love the story, this is great. I threw my whole life onto it and thought, let me film this — I thought it was going to be a great story.

Will: COVID was the thing where suddenly I had all this time, and I was just gaming, dude — filling the gaps between meetings, mornings, whatever, since you couldn't do anything else. My wife was like, "You play all these strategy games — you should learn how to make money, apply this to something with your time. Stop gaming."

I'd actually heard about Bitcoin way back in 2012 or 2013, when it was like $14. I was making $35,000 a year and thought about buying $500 worth. But older guys at my work — rightfully suspicious, not knowing what it was — told me the government was going to make it illegal, that I'd just lose my money, and $500 was a lot to me then, so I didn't do it. They were Gen Xers, not boomers, with their lives already in order — they didn't need something like Bitcoin's upside. I did.

Fast forward to 2020, 2021, I start investigating it again and have this epiphany: if there's going to be a thing that makes millennials and Zoomers rich, it's this. It's the new land. Everyone complains you can't get a house, they're too expensive, they're not building them — because Boomers and Gen Xers already have all that locked up and aren't letting us in. This was the new virtual land that's actually real and provable, on the blockchain. That's what got me into it. I also got into some bad stuff along the way — Cardano, Polkadot — not even that bad, comparatively, but I say that to say: I totally feel you, because even going back to the early Bitcoin days, I think a lot of people feel that same financial despair. You think, I wish I could 10x — if I just 10x my money, I'd have so few problems. But how do you do that?

Jammasterlee: Right, and this seemed like one of the only vectors to do it.

Will: Back to your story — you meet Bitcoin Bill and decide to quit, put in all your savings, liquidate your tax-deferred accounts, and eventually even take equity out of your house.

Jammasterlee: Yeah. Refi.

Will: What was your goal there? What would "rich" have looked like for you? What were you hoping to hit, and what was your process? It sounds like it started spontaneous, but at some point you must have sat down and mapped out how you were actually going to buy things. Walk us through that.

Jammasterlee: Going back to what you said — there's no way I can get ahead, no way I can have that great life or feel like I've risen above, especially as a guy. I think that first video I made, where I said fuck it, fuck the government, I'm quitting my job and putting everything on this — that plucked the same chord, that resonance people felt. That was my goal on an ideological level: I was chained and shackled, and I wanted to break the chains. Honestly, there wasn't a well-thought-out, logical plan. Bill had the whole mastermind thing going, and I was just along for the ride — whatever he told me to do, I did.

I was on Binance — I don't even know if you can use it anymore, but back then, in the Wild West days, all you needed was a VPN and you could get on there with all sorts of leverage available. My thinking was that if I could get somewhere around $10 to $20 million, I could cruise off the interest. So it was about half a million to $600,000 into the coin, and then triple leverage that, and it could very quickly become—

Will: You don't even need to hit $300K Bitcoin if you're using leverage to get to that number, right?

Jammasterlee: Right — if it had just gotten to like $80K, I think I would've gotten close, because I was in other coins too and got pretty lucky on some. I got into SHIB as it was blowing up and went something like 20x on $50,000 — some ridiculous amount of money. It's just crazy because, as you say, you're slaving away. You're just fucking slaving away. For me, I had a pretty good gig in some sense — I could make anywhere between $100,000 and $200,000 a year. That's pretty good money for me anyway. But you're crushing yourself for it. And with SHIB, I think I made $800,000 in a week.

Will: Whoa.

Jammasterlee: And dude, you go cross-eyed. Everyone's like, "Oh, I would have sold." And maybe you would have, but that crack goes to your head. You've never felt euphoria like that.

Will: I remember feeling excited just watching Bitcoin go to $60,000, and ETH touch the $4,000s. I was just like, holy crap. And I also didn't sell. I rode through the entire thing.

Jammasterlee: Down to $18, back up to—

Will: Yeah, I just rode it because we didn't put in nearly that amount — I was just kind of dabbling. But I remember, even at the levels I was playing at, that anxiety on the way up, the cortisol just being like, oh my God, do I have to log in, do I have to trade, texting people I know who work at this or that crypto company like, "What's your opinion?" And the narrative, of course, was that Bitcoin was definitely going to $100,000 that cycle.

Jammasterlee: Yeah, this is the end of the cycles now. It's just gonna become normal.

Will: And I had a spreadsheet. I was sitting down thinking, well, if Bitcoin goes to $100K, then we'll have this much, and that means ETH is probably gonna go here. And that's crazy, because we got ETH super cheap, like $300. So if ETH goes to $6,000, that's a 20x on our ETH. And I'm looking at this thinking, this is so sick — I've just conjured all this money out of thin air, only to have it fall out. And then, of course, everyone post-top calling it like, "It was so obvious, look at this indicator, that indicator" — the revisionist history of it all.

Jammasterlee: Dude, it's such a toxic environment. Horrible.

Will: And a lot of people making content — not like you, but people doing the charts, trying to tell you which shitcoin to buy and all this.

Jammasterlee: I was trying to be the voice of reason in that space, because everyone was just, "I want 20x on this, 100x on this," meanwhile they're sitting in this shit apartment where you can just tell they don't have it, you know what I mean? They were guys like us, buying crypto, trying to scrape together that glorious Instagram life, that music-video life. And someone comes along like, "Oh, I have the answer," and you don't care who it is — you just want that answer and you'll take it from anyone. I was really careful to post all the shit that I went through.

Will: I think you posted very earnestly and honestly, in retrospect. At the time, though, especially in the first few months of your account, I was on the side of the disbelievers — like, this guy's doing a character. I thought it was amazing content either way. But I'm convinced now, if you want to resolve the rumors: I don't believe you were doing a character.

Jammasterlee: I wish it were so, you know.

Will: How did that feel — posting this stuff and having people come to the comments saying, "This isn't real, you're doing a bit"? Was that entertaining, or was it actually scary? How did you feel about that?

Jammasterlee: I thought it was hilarious. It made me think, yeah, you really don't know what's real. And I also felt like there's almost no way I can defend myself — what am I gonna say? There's nothing I can do to convince you I'm real if you don't believe it at that point, because the more I say, the less real I seem. "No, guys, I'm really real" — it's like, of course he'd say that. So I just found it amusing.

I'm the kind of person who hates lying. I'm honest to a fault — terrible at lying, first of all, because I have a terrible memory. If you tell me a secret, I'm good at keeping it because I'll forget it. I'm just all over the place, so for me to lie is an absurd proposition. I just don't. So yeah, I just found it funny.

Will: Even now, as you're reviewing that old content and putting it together, do you see it differently — like, you get it now? You were very exuberant, and I think there was something about your attitude, this "fuck it" energy, paired with the seriousness of this huge life move you were making. I think that combination felt hard to believe for people. But at the same time, from what you're saying, I can understand it as a manifestation of something — people watching didn't necessarily know the despair you were feeling. You mentioned it a little, but you never got too deep into the physical symptoms of how your job was affecting you. You just said, "I couldn't do it anymore." I don't remember you going further than that.

Jammasterlee: Oh yeah.

Will: So I think it's easier to understand in retrospect why you presented it that way. But I'm also curious — even though this is vlog content, you're still putting a version of yourself online. Was there a sense of performance or character to it? Like, is there an honest version of Steve that you put online that's a little different from the Steve who lives day to day? Or does it feel really one-to-one? Even for me making this show, I feel very authentically me, but I'm still conscious that it's being recorded and it's going to go out there — so there's a bit more discipline or self-censorship in how I behave here that's probably slightly different from just normal me. I don't know if you'd say anything similar about yourself.

Jammasterlee: In retrospect, now that we're talking about it, I think it's a compliment that people thought it was fake — because I was dramatizing the gestalt everyone was feeling. The fantasy character they had in their head, I was actually doing it. I was the guy crazy enough to actually do it.

Are you into astrology at all?

Will: I have a lot of secondary exposure to it through my wife and friends, but I don't know how to do the deep charts like they do.

Jammasterlee: I'll nerd out on it for one second. I have three planets in Gemini in my Midheaven — your Midheaven is your publicly-facing persona, how you present to the world. I have three, and Gemini is all about communication; someone who's Gemini would love doing this. Basically, that means I constantly have a movie reel in my head of myself as I'm doing things. I'm always watching and narrating myself — I'll do it while washing dishes, while getting ready for bed. It's this weird thing I do. I think that's why I desperately need to film myself. I'm on this reel, and I want to present this reel.

So I'd turn the camera on for those all-in moments, you know — the coin drops, the coin goes up 15%, I just bought a huge bag, I dropped another $60,000, I leveraged up even more. I'd turn the camera on because these were the movie moments. And I think there was an awareness — when the camera was on, I wanted my face to show what I was actually feeling. I wanted that to tell the real story.

Will: You went through a lot of phases with the channel. The earliest stuff, which is what I've seen from your edits so far, is still in the bull market — Bitcoin's on its way up. There are scares in there too, because even though you're playing with leverage, there was the move up, then back down, then up again.

Jammasterlee: And then the retrace, yep.

Will: As a mild spoiler, eventually things do start to go wrong. And there are other phases — you end up trying to learn to trade.

Jammasterlee: Yep, yeah.

Will: I'm trying to remember the other pursuits — I think you still had money in crypto, but you'd clearly lost a good portion of it, and you didn't want to go back to normal work.

Jammasterlee: Can't do normal life.

Will: Were Bill or other folks you'd met — I imagine your channel exposed you to a wider NYC crypto community — were they encouraging you into trading? Or were you just consuming content from other people doing that kind of charting? Maybe talk about what happened, because obviously Bitcoin didn't make you rich to the level you'd hoped, but you were trying to salvage it, trying to find ways to turn this into an actual profession. I'm kind of teeing up the next video for you to talk about.

Jammasterlee: Yeah, basically — we're on the way up, and speaking of iconic, cliché stories: we'd rent these race cars, these super powerful cars, and take them out on the highway. There was a moment we let this girl drive, and she almost killed us all. I remember narrowly avoiding that and thinking, man, this is such a cliché moment — like straight out of Too Fast Too Furious or whatever. We were partying a bunch, and it just kept going up.

Then we had that scare with the double top, and on the trough we were freaking out. Then it went back up even higher, and we thought, we're golden, we're in the golden age of the new crypto era — getting super high on that. Then it had the massive crash. I got woken up in the middle of the night, I think by my sister, saying, "The coin dropped, are you okay?" I immediately called Bitcoin Bill, and you're just clicking like mad trying to sell.

Will: Yeah.

Jammasterlee: I don't know if you traded on ETH during that time — I don't know how the network handles capacity now, but back then it could not handle it well. I remember watching my health factor. If you've ever traded on leverage — hopefully you haven't, but if you have — there's a health factor, a number. If you have no leverage, the number is 1.

Will: Hmm.

Jammasterlee: Something like that. You're totally fine at 1. If it drops below 1, you're about to get liquidated. And I saw it go from 3, to 2, to 1, and then it got to 0.95, 0.9. I'm like, dude, I'm fucked. And the money's still there, but the ETH network just couldn't crunch it out fast enough. By the time ETH caught up to me, the coin had rebounded above my liquidation level. But at that point I'd already lost about 80% of my original investment. Fifteen years of hard work just vaporized. And of course, what do you do when you lose in Vegas? You go right back in trying to make it back. So we just crash traded, all in, and then it goes up and we never sold, and then it goes back down and we lose even more, and we're getting destroyed on gas fees. I think that whole experience taught me one thing: Wilson, man, I just can't do normal life.

Will: Yeah.

Jammasterlee: I just can't do it. It won't happen. The end story is I finally got scammed because I thought someone else could trade for me. Lost another $30,000 to $60,000. And I was like, okay, I should start sending out my resume. Then at one point I just thought, I can't go back to an office.

Will: And that's when you got into the TA, doing the paper trading and stuff for a while, I remember. There's some other stuff I can't quite remember since it hasn't made it into your cut of the movie yet. But during all of this, the tone obviously changed, and I'm sure people weren't super nice to you once you started to lose. There were probably some kind folks pulling for you in the comments, but I'm sure there were a lot of mean ones too. Making content through that whole arc — kudos for committing to it, because it's easy to make content when you're feeling up.

Jammasterlee: Your shit's awesome, yeah.

Will: And you have a lot to talk about.

Jammasterlee: You guys are all stupid, yeah, totally.

Will: It's a whole other thing to commit and keep doing it when things go the other way. Was there ever a point with the TikTok channel where you thought about quitting, or where it started having negative effects on you because of how people were interacting with it? I don't know if you ever had issues with people harassing you outside of TikTok, but I know that happens to people. Was there a point where you were like, I'm outta here?

Jammasterlee: Can't do this anymore.

Will: Right. What kept you going? I have a bit of a guess — maybe you just got so into making it, into the astrology thing and all that. But did you ever almost quit, or have you always been really convicted about keeping the channel going?

Jammasterlee: What's funny is the only time I've ever really stopped making TikToks is right around now, mostly because nothing's really happening — I'm just cranking away at other projects. But there was one guy, Cactus Pits, who did get to me. I banned him for a month, let him back on, then banned him again, because he had some really vicious zingers. One time I said, "Maybe I'll start a podcast," and he goes, "Yeah, you can call it Broke Rogan."

Will: Wow.

Jammasterlee: That one hurt. I told my friend, and he was like, "You know, it is kind of funny though." And I was like, yeah, I know. But I kind of loved the whole circus of it. I was always aware that what I was doing was utterly unhinged, ridiculous, out of proportion, and I wanted it to be entertaining for people. The crash is the best part — there's this person outside of myself going, no, no, keep going, keep the film running, this is gold. I don't know if it's sadistic or whatever, but above all, I just wanted to tell the story.

Will: Was there a point, especially as your situation got worse, where you had an intuition — not quite a premonition, but a sense — that you could actually do something with this content? I know it's hard to monetize on TikTok; you have to be massive. Did it ever occur to you, even years ago when things were rough, that this period of your life could become something — like this movie you're trying to put together now? Or even if not something huge, just something that helps you get back to even?

Jammasterlee: I really was in love with the story. I was enthralled by filming something real. I think part of it was compassion, or empathy, because I was one of those guys who felt beaten down. I didn't feel like a winner. I didn't feel like I could ever be famous, or live a life I was proud of, if I didn't somehow rise above the fold — and that just meant money. It's hard to see how money wouldn't solve almost all your problems. It's just hard not to see that.

What I really wanted while filming the downfall — what I was sort of aware of as I filmed it — was, maybe this will help some other guy who got his ass kicked. Maybe it'll help someone else not feel so shitty. And then I felt like, well, if I film this part, I'd need some story where I come out of it, where I show: look, you can survive this.

Another thing I was thinking — even at the bottom, Wilson, even when shit was falling apart, even when I got scammed — there was a point where I was so traumatized by the whole thing that my mom said, "Just go watch a movie." She was horrified. She took me to Fast and Furious Part 9. Dude, every car crash scene, I couldn't even watch it.

Will: Yeah.

Jammasterlee: I was just thinking about my money the whole time. But I was consciously aware that I was happier even during those times than I ever was selling insurance.

Will: Hmm.

Jammasterlee: I was living my life. I was making my own decisions. I wasn't being funneled into the rat race, this preset path you have to walk to be considered a good citizen so you can retire comfortably and nothing bad ever happens to you. I just couldn't do that, man. That shit was horrible.

Will: There was a point in the series — I don't know if it was because of your family or your own self-discovery — where you got into Gamblers Anonymous.

Jammasterlee: Yeah.

Will: You were working with a sponsor and not trading. I think this was after a lot of the paper trading and TA stuff. Eventually you said you stopped doing that too. What was that like, and what encouraged you to get into it in the first place? I can guess, but—

Jammasterlee: Haven't you been listening, Wilson?

Will: Yeah, but what was it like? I know it's probably something you're not supposed to talk about much, but to the extent you can — what was it like, and why did you decide to leave it? Or have you gone back and forth, or have you resolved that this isn't an addiction thing?

Jammasterlee: It was an up and down process. I remember thinking, I gotta stop, I gotta get out, I need help. New York offers free gambling addiction counseling — God bless them. I've since gone more conservative, but those liberal programs really help. I'll just call her Jenny. We'd talk a little bit. At the time I was trying to work at a restaurant making fuck-all — $15, $20 an hour, actually kind of what I'm doing now — and I'd think, I can't do this, and jump back into Bitcoin. Ride the wave, look at Bitcoin Bill's lavish lifestyle. So then I'd quit the counseling. But once I got scammed, I was like, okay, that's it, and I went back to it for real. It wasn't a group, just me and her over Zoom. I still see her — once a month we check in. It's beautiful.

Will: Did that also lead you toward exploring religion and faith, or did you already have exposure to that beforehand? There's definitely a turn in your self-care and recovery process where you get into religion and philosophy.

Jammasterlee: Getting kicked in the face multiple times really forces you to look in the mirror. I'd always wanted to make more spiritual content, I guess — content where I try to get people to be vulnerable, where we get to see their soul in a way even they don't expect. I used to do street interviews with that goal. My very first one, I had this guy tell me he'd been invited to this weird prostitution ring, and some of the prostitutes were underage, and it freaked him out. This was my very first interview on the street, and his face is on camera.

Will: Why are you telling me this, dude?

Jammasterlee: I know. I told him, this is for my YouTube channel, do you mind doing it? He knew everything and that I was going to post it, and he seemed really comfortable with it. That blew me away.

I think the appeal was sort of a return to that. It's weird, because I'd always thought of myself as a pretty spiritual person. I guess I was, but the Bitcoin thing exposed a side of me that was very much enraptured and entranced by the story of money and what it can do for you — the story of fame and fortune. Letting go of that was excruciating, genuinely painful. Many nights crying, depressed as fuck for several months.

Will: Were there any books or philosophers — what did you gravitate toward? I get the sense you've explored a lot, but what helped you most come through to the other side?

Jammasterlee: Strangely enough — the crypto bros will appreciate hearing this — Jordan Peterson. I must have googled "meaning in life" or something. I was so low, and Peterson just kept popping up in my feed. At first I dismissed him — "he's not giving any trade advice" — and I got rid of him. Then he came up again after I'd hit bottom.

I had this moment lying in my bathtub, the shower just dribbling onto my face as I lay there, and I remember asking myself: do you want to go on?

Will: Right.

Jammasterlee: Do you wanna just keep doing life? There was this part of me inside — and maybe this is why I kept filming — that was like, "Yeah, dude, you're doing great." I don't know where the fuck that came from. The whole time there was just this joyful presence, and I construed it as sort of like God. I was like, why the fuck is he so cheerful? My life is just — I've totally fucked myself up.

So from that moment, I started listening to Jordan Peterson. He had so many great little things he'd say. One of them was, "The nobler the aim, the better your life." And that's a very interesting thing to know. I was getting into the whole dopamine thing and how your brain works — you can only feel good if you're moving towards a valued goal. So then the highest goal — he had this thing, "the greatest good of which you can conceive." I liked that, because I used to go to church and they'd always say, "You have to do the mission of God." And I was always like, I don't know what I'm supposed to do. Am I supposed to take you by the shoulders and say, "Believe in Jesus"? Is that what I'm supposed to do? Like, do you, Wilson? Do you know Jesus is the way? It just never really appealed to me.

But "the greatest good of which you can conceive" — I'm like, oh, well, the greatest good I can conceive of is to make videos that help people grow, or help them feel like they're known. So that's what kind of started the comeback, I guess you could say.

Will: Well, your room looks very clean, so I think he would approve.

Jammasterlee: Step one, man. Took me six months to clean this room.

Will: And then I told you we weren't using the video for this and you're like, goddamn.

Jammasterlee: I almost just shut it off, dude.

Will: Like you were gonna walk away from the whole thing. I'm not a huge fan of Peterson personally, but the way I approach any religion or philosophy is: if it's helping people and it's not hurting me, then that's good.

Jammasterlee: That's a good baseline.

Will: There's probably aspects of what he says that aren't so good, but it sounds like you've crystallized around the parts that are pretty unobjectionable — "have noble goals and pursue them" isn't exactly controversial. So it's awesome that was helpful to you. What about Bitcoin Bill — are you still in touch with him, or any of the other characters who float in and out of the story? He's the one who's most consistent. Are you still friends? Was he someone who was just rich and playing this whole time? How wrecked did he get in all this? You said he's still living a pretty good lifestyle.

Jammasterlee: I actually don't know. I assume he is — he was living a pretty good lifestyle when I got wrecked. He got wrecked too, but he'd been close to $100 million. He was $60 to $80 million at one point. He had 30,000 ETH at one point, which was utterly disgusting — bigger than Grayscale, bigger than a lot of the names you hear about in the media.

So I don't know how he's doing now. But I think Bill really was living out his calling. He'd lost big fortunes multiple times and it never really deterred him from trying again — it was probably just the life he was cut out to do. Our relationship, though, was unhealthy. Codependent isn't quite the right word, but we kind of fed off each other. He was sort of the god and I was sort of the worshiper — a messianic figure, or a demagogue, take your pick. I'd feed his ego, we'd always show up at parties together, and I was sort of his security blanket in some sense, being the adoring fan. When things were good, it was great. But when it turned, there was a lot of finger-pointing, a lot of wanting to blame him. There's an aspect of that which is fair — he may have abused some of his influence — but I think he just didn't know any better either. And I'm a man; I had to own my own demise. Short story: we're not friends anymore, we don't really talk. The other day I was thinking, I've done worse, I've done horrible things to people too. Shit happens.

Will: I can't help myself with things like this, because the way I like to add value is to hear ideas and expand on them — so take it or leave it. I know Bill was never shown on the channel, and maybe he doesn't want his face out there, but it could be a really poetic moment in your project to actually get him on and talk about it after the fact. You seem to have moved past a lot of the bad feelings — it could be powerful to reminisce with him, and also find out whether he's even aware of a lot of the content you've made since you parted ways.

We can cut this if you want, but it just popped into my head: that could be a great button on the end of the story of this movie — if he'd do it, which he probably wouldn't if he doesn't want to be doxxed.

Jammasterlee: I really appreciate you saying that. That's a really interesting idea. Wow. That's powerful.

Will: I just wanted to get it out while I was thinking about it.

Jammasterlee: No, that's really interesting.

Will: As a viewer of your content — and I'm pretty sure I've seen all of it — one of the big questions I have is, what is up with this guy? What's he like? Because in the moments where you film, he's off screen, we don't hear his voice, we just hear you talking: "Bill's over there, he's got his two phones and a laptop, we're having a trading session."

Jammasterlee: The unveiling of Bitcoin Bill.

Will: That would be interesting to see. So, let's talk about what you're up to now. You're pulling all these TikToks down and editing them together, which is surely a hell of a process. Do you have a ballpark of how many total hours of content you've put online? It's something like four years of content, calendar-wise — but how many hours?

Jammasterlee: 2020 to 2023, probably, at least for the core story. It's a shitload. I was looking at five or six videos a day, and it took me something like five months to get through it all. They were short videos, so maybe it was only 40 hours total, maybe 100 — I don't know. It's a bit of a bear to put together. I've done three rounds of edits, and I'm on the fourth round now, realizing I need to splice it up more just to keep it moving. It feels like a giant jigsaw puzzle — a million pieces you're trying to organize by color and then put together.

Will: And you're talking about editing just this first chapter, right, not the whole thing? Is there more content you've edited beyond what you've shared with me, or have you just focused on that first chapter or so?

Jammasterlee: I've sifted through the entire story — three rounds of sifting, trimming, cutting whole videos. So I've been through the entire story up until New Year's of 2022, I think — the year I cleaned my room. My room was finally clean, and right now I wait tables on the weekends and crank through Torah and ancient Hebrew during the week — I'm pretty into the spirituality thing these days. That feels like a good stopping point for the series, right at New Year's, ten days out. I was nervously hoping shit wouldn't blow up on me, since I'd already been fired from a couple jobs trying to get back to a normal life. Even waiting tables felt inadequate — not an illusion exactly, but it still didn't feel like real life, which was fine, because I didn't want real life.

But I'd fucked up so badly with Bitcoin, with getting scammed, with losing jobs. My mom ended up in the hospital during this from stress, and I think it was from watching me go through it. I felt like the biggest fuck-up — my relationship with myself was all but destroyed. So there was the room-cleaning, and also temper tantrums at work, I almost got in a fight — I was a little unhinged. But it started to come together, and I'd really mastered myself by the ten-day countdown to New Year's. That's the last video I've edited so far.

Will: How long do you think the finished thing will be in total — two hours, three hours, once it's condensed?

Jammasterlee: I hope to get it under two hours, just so people will actually watch it. As a content creator you're always worried about length — I don't want it too long. But it depends.

Will: It depends on your plan for releasing it, too. Do you imagine people watching it through a website, buying it in chunks or episodes? Or do you want it shown at festivals or something like that? Those don't have to be mutually exclusive. I work in video games, and there's a company called Double Fine that sometimes takes five or six years to make a game. They have a documentary crew embedded with them the whole time, funded and paid, but with basically no editorial control over the final cut.

Jammasterlee: Huh.

Will: They finish the game, then release the documentary, all on YouTube. It's not 90 minutes or two hours — because it's covering that many years, it ends up being like 12 hours total, but chopped into episodes of 20, 30, 40 minutes each.

Jammasterlee: So they do chop it up.

Will: Yeah. I think YouTube practically requires that, but it also helps the storytelling to have distinct milestones, moments where things happen. I love that series — I recommend it to everyone, you don't even have to be a gamer, because it's not about playing the game, it's about making it and the people involved. You see people get hired, people get fired, and they're very transparent and open about all of it.

Jammasterlee: It's a relatable story.

Will: A lot of people understand what it's like to work.

Jammasterlee: Exactly. How to build something and—

Will: I'll send you the links so you can see what they're about — it's a great example of how to do long-form documentary really well. I hope they continue doing it, because — kind of a spoiler — they've made two of them, and at the end of the second one, their company got bought by Microsoft. They're literally talking to legal and the business dev guy, trying to make sure they can still make these documentaries once they're absorbed. I don't know if they got a resolution to that, but I really hope so, because those things are so raw and so fascinating.

Jammasterlee: They're gold. They really touch you.

Will: None of the people in it are actors — they're all real, dealing with their own shit.

So, have you thought about how you're going to release your movie?

Jammasterlee: Honestly, no. I'm realizing I have my own style I'm trying to go for, and I'm just experimenting with it now. I haven't thought about release at all. I don't know if anyone would watch it, if it'd be good, or if I should hire someone. Actually, it makes me a little sad thinking about the Microsoft buyout — that seems to be the goal of every startup. That's when they get put out to pasture: bought out, absorbed into the monolith.

Will: For them it wasn't really the goal — they'd been an independent company making games for twenty-some years. Did you ever play games as a kid? They made Day of the Tentacle and Maniac Mansion.

Jammasterlee: I had Donkey Kong, dude.

Will: This would've been the '90s — early PC gaming stuff. They even had Jack Black doing voice acting before he was famous.

Jammasterlee: He's a good guy.

Will: Yeah, and because of that relationship he still comes back and does VO for them from time to time, probably at a dirt-cheap rate. But given how long they spend on their games and how over budget they go, getting bought out seemed, from my read, like a necessity to continue as a company.

Jammasterlee: They just couldn't sustain the model they had.

Will: Right — so to keep the team together and have some hope of continuing to do what they do, they have to cross their fingers and pray that getting folded into this big conglomerate doesn't mess them up too much.

Jammasterlee: Doesn't just absorb them into the Borg.

Will: I think we've touched on everything, but here's a question: after you release the movie, what are you going to do? Keep filming and doing TikTok? You're going to get all this time back — you won't be editing constantly anymore. More philosophy and religious stuff? Start speaking Hebrew on TikTok?

Jammasterlee: I still touch it every day — doesn't take much time, maybe 20 or 30 minutes. Good process. Now I'm moving toward wanting to do lectures online — I'm working on a YouTube video about how the Bible might have gotten written. I just love ancient history. I'm a gamer at heart, a fantasy gamer at heart, so anything ancient and fantastical, I'm in. I guess you could call me religious, but I'm also down with the Atlantis story, pyramids as power plants, aliens — all of it.

Will: I have a total soft spot for Graham Hancock stuff. I'm always like, okay, but why is it like that? The flood myths — why do all these cultures around the world have the same flood myth?

Jammasterlee: Yeah, the flood myth is really interesting.

Will: I'm a conspiracy-minded person, but I try to keep some distance from it. Then I heard him on Duncan Trussell and Rogan and thought, whoa, this guy is—

Jammasterlee: I got so into it the first time I heard him. I sent a clip to a friend like, "Dude, did you see this?" He just thought I was a psycho.

Will: I haven't kept up with what Hancock's doing now, but his whole comparison of different cultures and their iconography — I think the issue is he's asking questions that are hard to answer, so they're very open-ended, and he's picking one particular interpretation.

Jammasterlee: He's a little fantastical, but I appreciate it.

Will: He's doing a character, and it's his living — he does a good job making it interesting, speaks well. There's a non-zero chance he's right, and I wouldn't be as vociferously saying he's wrong as some other people are.

Jammasterlee: Don't spoil the party, man. We're just having a good time over here. I read Hero with a Thousand Faces — my friend sent me that book. It gets more rigorous about the similarities in the hero story across cultures. He even made a case for cannibalism, which I thought was really interesting.

Will: I don't know that one.

Jammasterlee: Child cannibalism. He explained what it was and why they did it, and I remember reading it thinking, "Oh, that actually kind of makes sense." That surprised me. That'll be a good soundbite, right?

Will: Take that out of context.

Jammasterlee: "Jammasterlee supports child cannibalism." Can't wait for that headline. If anyone cares enough.

Will: Big recommendation on that — I find it super entertaining, and it's awesome to hear someone come up with those ideas, to understand what people are capable of. Do you have anything you want to plug? Your TikTok and Twitter are both @jammasterlee, we'll link them below so people can catch up before the movie comes out. Do you have an estimate for when you might finish this project?

Jammasterlee: The fourth round of edits is definitely the most challenging, because I'm really trying to compose it. Maybe a year, something like that.

Will: Are you open to people reaching out if they want to help, take a watch, or give feedback? A lot of New York City people listen to this.

Jammasterlee: Hit me up, man, 24/7. I'm super down — I could use all the help I can get. I don't know how much I can pay you, but it'll be a passion project.

Will: For anyone listening: the idea of taking a bunch of TikToks that are already pre-curated — you've done a lot of the heavy lifting already.

Jammasterlee: A lot of the sifting is done. You're looking at the meat and potatoes, at least.

Will: Steven, thank you so much for coming on. It took a lot of trust to let some random guy hit your DMs.

Jammasterlee: That was the hardest part, actually. Smooth sailing from there.

Will: I get it, because in crypto you're so used to people scamming.

Jammasterlee: So much shadiness.

Will: I appreciate you having trust — we talked a few months ago and I explained what I'm about and what the show's about.

Jammasterlee: You've been great.

Will: It's a big thing to talk about — this chunk of your life. We've talked a lot on the show about how a lot of artists have gotten into this crypto game with NFTs, made money, and somehow ended up with nothing, wondering what happened.

Jammasterlee: Right.

Will: I think it's a relatable story, and I'm sure a lot of collectors have had big swings too, being in the crypto space.

Jammasterlee: You get that euphoria, and then it's just a crazy tidal wave.

Will: Definitely go check out Steven's content — Jammasterlee, links below. And when your project's out there, let us know — we'll post it on Twitter and share it around, because I think anyone in the crypto art space will find this really interesting for a variety of reasons. Thanks so much for taking the time to come on.

Jammasterlee: You'll be the first to know. Thanks for not being a rug pull. This has been really enjoyable.

Will: Let's leave it there — hope everyone listening enjoyed it. We'll be back in a couple weeks with another Waiting to Be Signed episode. Thanks again, Steve.

Jammasterlee: All right, man.

Will: Bye.

Jammasterlee: Bye. We're waiting, always. We're waiting to be signed.

Change log

  • Initial transcript — auto-transcribed (AssemblyAI) and readability-edited.