The Exchanges

Q So did you, did you know Tiago or you basically just took his course, got to know him and then he became your business partner?

A Mostly the second. I just really admired Tiago. I still do. And I was like, wow, this guy understands something about information capture, something about sort of the creative process, something about online education that I would really like to learn from. And the man and his system just radically transformed my life. And so I reached out to him. I remember we had lunch in San Francisco. And I called him on a rainy day in New York City, December seventh, 2000 and, and 18. And he, in a five minute conversation said, sure, um, I'm happy to do it. And at the time I had very little money. And right around then I got a 20,000 dollar grant from Tyler Cowen's Merchant Ventures program, took that 20,000 dollars, hired a Hollywood film crew, flew them down to Mexico City. We made these Seven video modules, and in 10 days, came up with all the concepts that would eventually form the bedrock of Rite of Passage, and here we are now.

AI assessment note: “Mostly the second. I just really admired Tiago.”

Q you had a little bit of that. Like you took the 20,000 dollars. You're like, I'm going to take this bet. Uh, I hope it works out, but could you talk a little bit more of how you were feeling at that time? Like, did you feel like, oh my God, if I spend all this money and it doesn't work out and you know, this is, this is it.

A I had nothing to lose. I had nothing to lose. I mean, I'm a born entrepreneur. There's no working for anybody else. My dad was an entrepreneur. I grew up under that. And my dad always made me believe that I could do it. There was no other option. It was just an option of whether I'm gonna do it now, whether I'm gonna do it later. And I remember I knew very early on that having an online audience, especially around ideas and something that you know about the world is super valuable. I remember after I got laid off from my job, My first and only job. I called my dad and I said, Hey, I'm going to go build an audience. And I have the worst plan for two years, the best plan for 10. And I think that was totally right. That was more than half a decade ago. And those first two years were brutal. And I think over a 10 year time horizon, it's going to turn out really well, but there's no other option for me, man. This is what I do.

AI assessment note: “I had nothing to lose. I had nothing to lose. I mean, I'm a born entrepreneur.”

Q I felt like. Words had been very similar to how podcasting is. Podcast discovery is notoriously difficult. It's notoriously hard to start a podcast, unless you have an audience already, start a podcast, disseminate it, distribute it, get it seen, get it listened hundreds of thousands, thousands, even hundreds of times. And it's because the platforms don't lend themselves well to share ability. Do you agree with that or not?

A Yeah, totally. And I would just add Substack in here. I think Substack has done a lot of the same things that Twitter's had. And especially now Substack is doing a great job of recommending newsletters. That's what people need help with distribution. It used to be that anyone could start their own blog, but those blogs wouldn't get read. And now if you're writing on Substack. If you're writing on Twitter and your stuff is good, it'll be seen and it'll be seen by people who you wouldn't be able to meet in real life. And that is something worth taking advantage of. And rite of passage is a five week program where people learn exactly how to step into this world and put it to use for them.

AI assessment note: “Yeah, totally. And I would just add Substack in here.”

Q going, you know, going deeper into religion because it is in a lot of ways unpopular, like an R group. Am I, am I misstepping by saying that? I feel like an R kind of crew of people. Like, I don't know a lot of people posting and writing about religion and going deep and, and, and kind of having a, a pastor over here and a rabbi over there.

A Yeah, I mean, I, like, I think that's ridiculous. You know, I think that I looked at a lot of the secular and atheist perspectives on, and I say this as someone who's not religious, but I just looked at a lot of people around me and I would ask, why are you not religious? And their answers for why they're not religious, I thought was very shallow when I looked at the average person and I said, Hey, I don't know what my answer is, but whether I'm religious or not, I better have a good answer for why I think that The different perspective is false. You know, it's Charlie Bunger saying, hey, you should understand the other side's opinion better than they do, what they think better than they do. And for me, I don't care what Christians do. I care what the Bible says. And that's what I want to focus on. And I want to know this stuff well, because I think that that's what it means to be an educated Westerner. I think that this is a core thing. And I think a lot more people should be learning about it. Not to be religious, but because it's important to know the Bible, because so much of your life, if you live in the West, this book, the Bible, the Old and New Testament, influences your life each and every day, and understanding that moral framework, how the stories that are told influence the Constitution and the laws of the countries that you live in, I think it's an important thing …

AI assessment note: “I don't care what Christians do. I care what the Bible says.”

Q what would a rite of passage look like for XYZ vertical? And I'm wondering, first of all, do you have any ideas where you're like, oh, I wish someone would build, you know, rite of passage for XYZ. So that's one question. And the other question is, you know, are you tempted To, you know, basically expand your curriculum. Like, what does this look like in 10 years, let's say?

A I don't know, but a lot of how I think about what the company wants to be is I sort of work back with who are my heroes and what is the fact that they're my hero, the fact that they are, that I'm so interested in what they did, how they built their career. I sort of ask, what is it about what they did that's really interesting to me? And the person I'm just obsessed with is Walt Disney. I went to Disneyland earlier this year. And I flew out to Orange County to just say, what can I learn from Disneyland that I can then apply to Rite of Passage? And I basically want Rite of Passage to be like Disneyland for writing. I eventually want to have houses around the world where people can come in and have conversations that embody the Rite of Passage spirit, test them out to greatness. What does it mean to sort of be surrounded by People who've actually added something to human civilization. You know, there's no coincidence that right behind me, I have the story of civilization books right here by Will and Ariel Durant. I have a whole collection from Michelangelo and Da Vinci. Like I want this room to basically be this holy place, this sort of cathedral of knowledge. And I would love to build. Places around the world that embody that. And I want rite of passage to feel like Disneyland. And some of the things that Walt did that I thought was fascinating is like, for example, when Walt wa…

AI assessment note: “I basically want Rite of Passage to be like Disneyland for writing.”

Q identity, shared language, shared rituals. It comes from very much deeply rooted in religion, um, in lots of ways. And I've, I've heard you actually talk about religion before on other podcasts. You know, I know you're a student of religion, but could you talk a little bit about maybe some similarities that you see with what you're building at rite of passage and interestingly enough, how religion is structured?

A Yeah. It's funny that you talk about the, the, the similarities. I never have them be similar. So I'm just going to go on the religious tangent of why I think that this is important. And then we can sort of horseshoe and sort of try to connect these two things. I haven't really thought about that before. Um, but so I'm secular, I grew up Jewish, and I had this realization that the Bible is the core text of Western civilization. And the more that you look at it, you realize that the moral framework That we have, whether you're atheist, secular, or Christian Jewish, it is all within this Judeo-Christian tradition. And even the most atheist of Westerners actually have a quite Christian moral framework. And you see this in the Constitution, right? We hold these truths to be self-evident that all men are created equal. It's not self-evident at all that that's the case. That sort of builds on John Locke's ideas, and that then goes back to the Bible. And I realized that when I, I was basically swimming in, in Christian waters, and I didn't understand the Bible. So every week I Do a Bible study with the teacher every Sunday morning for two hours. And I am deeply obsessed with learning what the Bible says, going through it. And then I also work with a Chabad rabbi in town so I can get a different perspective. And, you know, part of this is my own journey to find faith. And part of this …

AI assessment note: “So I'm just going to go on the religious tangent of why I think”