#141 Ryan Holiday's Secret Weapon - Billy Oppenheimer on growing in Philadelphia, almost going to law school, role models, working with Ryan Holiday, his research process, the notecard system, skiing, and the downsides to fame

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today I am talking with my guest who's joining me for tea in my home, Billy Oppenheimer. He is a writer, super curious human. Also happens to be a research assistant for Ryan Holiday. Excited to dive into all this today, explore what it's like working for a creator, your own creative journey, some of your own ahas along the way from travel, the creative path, et cetera.

Welcome to The Pathless Path.

[01:40] Billy Oppenheimer: Good to be here, Paul. I'm a fan of your work, the podcast, the book was, really helpful for me to sort of make sense of the journey I've been on. So I'm happy to talk with you more.

[01:55] Paul: Awesome. So one of the things I talk about in the book is our scripts we grew up with, right? The default path I talk about. And we've talked a bit about this in Austin. What, what were the stories and scripts you grew up with that shaped life for you growing up?

[02:13] Billy Oppenheimer: So I feel pretty fortunate because when I think back on childhood and like middle school, high school, I didn't have anything. My parents weren't pushing me to go down any, any sort of path. They were no real expectations beyond just like sort of just blind support of— I'm the youngest of 3 and I feel like they just by the time it got to me, they— it wasn't like—

[02:41] Paul: it's always way more chill on the youngest, right?

[02:44] Billy Oppenheimer: Yeah, I think I— there's less eyes on me and just my parents were supportive of whatever I wanted to do. And I didn't have any real— my dad was an entrepreneur, had his own company, and my mom worked for him in the business and So it was influential for me to see that and that there was never any pressure to do this or that. It was sort of just, I was on my own almost.

[03:16] Paul: Awesome. So your dad, you wrote about your dad, you wrote this thing. I didn't realize till later he had money. And were you shocked by that or just, the messages you were getting from him, which was not money-centric, and it turned out he was pretty successful.

[03:38] Billy Oppenheimer: Yeah, one of the things I now can sort of in hindsight kind of appreciate, or I think what he was sort of intentional about was money just wasn't a big deal. It wasn't something that was talked about. I had no clue what he was making with the how we were in terms of like middle class. I didn't have any sense of any of that.

[04:02] Paul: Where'd you grow up?

[04:04] Billy Oppenheimer: In Philadelphia, in a suburb outside the city. And yeah, it just wasn't a thing I thought about. Now looking back, I just like, I think it was, it definitely shaped some of the choices I make because that was, I never factored in money along the way. I still—

[04:23] Paul: You didn't even pick it up from society? I mean, Philadelphia, you're getting a lot of messages from your peers, I imagine.

[04:30] Billy Oppenheimer: Yes, I definitely, like, throughout high school and college, I thought I was going to go sort of the New York City finance or the business path because a lot of my friends in high school and college, that's sort of just— that was kind of what I— all I knew was like, those were the options.

[04:52] Paul: I found your lacrosse page on Lehigh's page and there's like a trivia about you. Have you read this in a while?

[05:01] Billy Oppenheimer: No.

[05:02] Paul: You know that's up there? No. So you wrote that. First, first off was like one of your role models was Johnny— like, who's the quarterback? Johnny— he was like very famous in high school but panned out in college. I'll have to pull it up.

But yeah.

[05:24] Billy Oppenheimer: I don't know. I'm not like a big football fan.

[05:28] Paul: But you said your dream jobs were to be to work at a law firm or Wall Street.

[05:34] Billy Oppenheimer: Really?

[05:34] Paul: Yeah.

[05:35] Billy Oppenheimer: Okay.

[05:36] Paul: That's exactly what you said. What is your dream job? Law firm or Wall Street?

[05:40] Billy Oppenheimer: Yes. Okay. That does. I mean, I don't— I don't remember that, but it is. That is where my head was at in college. And I actually I put, as you said, I played lacrosse.

So I remember I had a meeting with our assistant coach my junior year and we were just sort of talking about like career stuff and what I was thinking for after college. And I sort of told him I was thinking maybe law school. And I think I was landing on that just as like I wanted to have some, some like certainty in what I was telling people. Because when that conversation came up, I sort of just liked the idea of saying I might be going to law school.

[06:19] Paul: Yeah.

[06:21] Billy Oppenheimer: And he— my assistant coach was— he set up a phone call between me and one of his college teammates who went down the law track. And he was like, if anything, you'll, you'll, you'll learn maybe about like what path to go down. So he set up a call and I remember I was asking him all about his, his journey and he was like, Honestly, if I had to do it again, I wouldn't do it. And if I had any advice to you, I'd say don't go to law school.

[06:51] Paul: So many lawyers.

[06:53] Billy Oppenheimer: Yeah.

[06:53] Paul: Are like this. Yeah. But nobody ever listens to that. Did you listen?

[06:57] Billy Oppenheimer: I took it like from that conversation. I was like, law school is off the table.

[07:02] Paul: One convo.

[07:03] Billy Oppenheimer: Yeah. And I didn't even really know the guy that well, but he was so like— I remember the phone call and just like, wow, like Why would you—

[07:12] Paul: maybe do you think your coach was wanting you to talk to him to discover that?

[07:16] Billy Oppenheimer: Yes, because it's his— it's one of his good friends. And I think he knew that he was kind of miserable in that as a lawyer and super successful. And he still— I actually saw him like not too long ago. The first time I met him in person, I was like, I don't know if you remember this, but you're the one that talked to me about going to law school. He's like, no, I remember the conversation well.

[07:36] Paul: That's amazing. And you said you would look around when you were younger, maybe after this conversation, of people 1, 3, 5, 10 years ahead of you. Were you consciously doing that and seeking out people and looking for models, or was it just something you always paid attention to?

[07:53] Billy Oppenheimer: I think I, um, I'm more aware of it in the last couple years than I've— it was— it's long been like a subconscious thing for me because Even with sports, like the way I would with lacrosse, for instance, I would watch my favorite players and then I'd go out and like try to do what they did. And it's been my— that's my approach with writing and now with just like kind of career stuff. But I remember having that realization after college when I was like just kind of traveling, doing the ski bum chasing winter. And I thought I was going to do that for like at least the next 5 or 10 years because I just— it was so much fun. Um, and I was listening to Ryan on a podcast and he was talking about how he, um, one of the things he like learned from, or one of the reasons he wanted to work for Robert Greene, was like he liked the life Robert got to live and he wanted to go be close to that.

I was like, oh, that's interesting. And then I started to look around, like the people that are 10 or 15 years down this track that I'm on. And it kind of just, I was like pretty scared by that. I was like, I don't—

[09:12] Paul: The ski bum path. Right. Yeah. There are some people that seem to genuinely enjoy that, right? Yeah. You meet people in these communities and they're thriving, but there's also people who you can tell they're kind of yearning what if I had done this, right?

[09:25] Billy Oppenheimer: And I could, I could see like waking up in 40 years and just being like, what did I do? You know, it would have been a great— like, I would have got to ski a lot. It would have been kind of like an easy, chill, fun life. But then it's just like, man, I didn't like do much.

[09:43] Paul: Yeah.

[09:43] Billy Oppenheimer: So then that's when, um, I became like more like, all right, now let me go find someone who is 10 years ahead of me with like a life I, I would want.

[09:56] Paul: So outside of Ryan, uh, who else were some of those models for you?

[10:01] Billy Oppenheimer: Um, Robert Greene is definitely a huge—

[10:04] Paul: what about it though? Like just sitting around and writing?

[10:07] Billy Oppenheimer: I like that they—

[10:08] Paul: like Robert, he's a deep thinker.

[10:11] Billy Oppenheimer: Deep thinker. Um, like his job is just to like read and find stories and then bring that back to his writing. And if you like call Robert, it'll go straight to his voicemail. And he's just, you know, he's just like reading and he's just like on this relentless search for material that he can use in his writing. And I just— yeah, those are my two big like role models right now for sure.

[10:41] Paul: Did you have any anti-models besides the 40-year-old ski bums?

[10:45] Billy Oppenheimer: Uh, no, I don't know. I haven't like specifically pointed out someone who's like, yeah, that's not where I want to go. I'm more focused on like the people that I look up to and are doing work that, um, and have carved out just like the day-to-day-ness of a life that, yeah, um, that I would want.

[11:07] Paul: Awesome. So I, I've read the story about reaching out to Ryan, but at what point, um, What were you doing? Where were you? Who were you surrounded by in those key communities?

[11:20] Billy Oppenheimer: I was— so I— what I was doing was I was— I'd spend the Northern Hemisphere's winter in Colorado, and then I was going to New Zealand for their winter. And I was—

[11:33] Paul: I was chasing winter.

[11:35] Billy Oppenheimer: Chasing winter. Yep. And I was between seasons. I was home about to get on a flight back to Colorado. And prior to, like a year and a half prior to that, I'd started a blog that I was just sort of like keeping, basically only could conceive of my family reading it. So it was, I was just writing to kind of like keep people up to date with what I was doing and that kind of thing.

And my uncle, I saw him like between New Zealand and Colorado and he recommended one of Ryan's books.

[12:12] Paul: Which one?

[12:13] Billy Oppenheimer: Perennial Seller. Because he was like, if you— he was a fan of what I was doing. He like, liked my writing and he was like, you should think about taking this serious. And if you do, I just read this great book, like, wow, you should read it. And I read that book on the flight to Colorado. And, you know, at the back of the book it's like also by author.

So I ordered like his 3 or 4 other books and just like went down the rabbit hole of his work.

[12:44] Paul: What did that mean to you, your uncle sort of leaving? I mean, that stuff is huge.

[12:49] Billy Oppenheimer: It was huge because he is like kind of like— I don't know if notorious is the word, but like he's a regarded in our family as like a reader, and he himself is a writer.

[13:02] Paul: What kind of writing?

[13:04] Billy Oppenheimer: He's nonfiction, historical stuff. Huge Churchill fan. He's working on a Churchill book.

[13:12] Paul: Nice.

[13:13] Billy Oppenheimer: But it was like, yeah, for him to say he likes something about the writing was kind of cool.

[13:22] Paul: And What do you think he saw?

[13:25] Billy Oppenheimer: I don't know. I'm a little— I like, I think anyone that looks back on, on like their writing, even still for me today, like if I look back on stuff like 3, 4 months ago, I'm like, ooh, I don't know about that. Um, but I think there were like glimpses of like some good stuff. And, um, I actually was like, prior to finding Ryan's work, I was kind of gravitating towards a similar style. Of like storytelling from like what I was reading, stuff I was reading to tying it to like what I was learning in those travels. So it was, I think part he was like, this will be a good book if you want to take this serious, but also like a similar style.

[14:05] Paul: Yeah. So talk to me about reaching out to Ryan. You realized he was in the same town or town over, right? Yes.

[14:15] Billy Oppenheimer: Yes. Well, so no, I—

[14:16] Paul: You had emailed him first.

[14:18] Billy Oppenheimer: Yeah, emailed him and like June of 2018, after, I think by that point I read like 4 or 5 of his books and everything that he had published online and reached out to him, just offered to like help with the research stuff. And that led to a few like odd projects here and there. And then he was in Vail to give us, he was speaking at some conference and he posted a run on the app Strava, which I used at the time to like record runs. And I was walking out of my apartment to like go for a run, and I saw he had like just finished one in Vail. I was like, ah, that's weird. I wonder what he's doing here.

So I just, I emailed him. And prior to that, it hadn't come up like where I live, so he had no idea. I was like, how long you in town? Be awesome to meet in person. He's like, oh, I fly out tomorrow, but if you come to the, this conference, like, we'll find some time before or after. So I went to, to the thing and listened to him speak.

And then like afterwards, people were trying to like get some time with him and just keeps like doing this. He's like motioning me to like follow him and I'm like, all right. So then he like breaks away from the crowd and then we go upstairs. He's like waiting for his rental car to pick him up. And in that like 5 minutes, we just like chatted. I asked him a couple of questions and he was like, it's really good that you came out.

Like, we've been We've actually been looking to like bring on someone full-time. Like, would you have any interest? So yes, I just sort of jumped on that and then been working for him in that capacity since then.

[15:53] Paul: That's pretty amazing. He's, he's had— I sense he's had a big impact on many people. It's funny, and one of our mutual friends, Sky King, also cold emailed Ryan about the same time, thinking about leaving. Yeah, thinking about leaving his job and like saying, here's my vision for podcasting. And Ryan was like, go do it. Here are the books you need to read.

[16:14] Billy Oppenheimer: Interesting.

[16:14] Paul: Like a lot of why he ended up coming to Austin as well. It's a very similar story told on the podcast. You can look it up.

[16:22] Billy Oppenheimer: Wow, that's cool. Yeah, I, so I think I, the time between first emailing him and that, um, meeting in Vail, I think it was like 3 or 4 months. So in that time I was doing like odd projects for him. Um, so I would like go teach skiing and then I'd come back and like work on whatever I had to work on with Ryan. And then like what, um, he would have me like transcribe— like he would do like prior to starting the Daily Stoic podcast, he would do interviews on, on the site and he would record them with the— so like I, I transcribed like a 2-hour conversation between him and Robert. I did like a, a kind of summary piece of Epictetus' Discourses for the blog.

He would send me like a quote he had come across and like, can you find me the original source? Just like random stuff.

[17:20] Paul: Yeah. And this kind of stuff is so underrated. I don't think people understand like how powerful it can be just to be willing to do like grunt work.

[17:30] Billy Oppenheimer: Well, even, right, yeah. And now, like, when I see a quote, my, like, instinct is to go find the original source. And, like, I don't know if that would have came— it's just through, like, seeing how he tracks stuff down is like, it's— that has rubbed off on me. But also, yeah, the grunt, the grunt work. And, like, I just remember, like, transcribing that conversation and just being like, wow, no one's— like, I'm the only person that's, that's listening to this conversation. It's pretty cool.

But it was, yeah, it was just like random, random stuff. And it's still kind of like that. Like, I might have an email from him now, like an image from a book he's reading. It's like, hey, can we find— can we like triangulate this story?

[18:09] Paul: Yeah.

[18:10] Billy Oppenheimer: And then we just— I just sort of like go digging for like more on that.

[18:14] Paul: Yeah. And how do you—

[18:15] Billy Oppenheimer: what does your research process look like with Ryan specifically or just stuff like that?

[18:21] Paul: Like, how would you go— how would you approach that? Obviously, you start with Google and might go to books.

[18:29] Billy Oppenheimer: So everything, for the most part, a lot of what we read is biographies. And he's looking for stories. So if he finds a story about the Queen in one biography, he wants to triangulate it to see maybe in the telling in this other book, there's a, there's like a quote that this biographer didn't use. So what I'll do is like I'll grab a section of the story and like quote search it in Google and then filter like by the other books and see what, like, who else is telling the story. And then I'll order those books and, and go find that, like, that story and just put all the core details and things left out and the version he read into a document and just like send that to him.

[19:22] Paul: Yeah, this is such an underrated thing. I feel like so many people are communicating at like the abstracted layer of like current knowledge. Yeah. And just sort of— it's so easy to just go into the books and find out what people said and then like go like even one layer deep.

[19:41] Billy Oppenheimer: Yeah.

[19:41] Paul: You're usually finding things that nobody else is looking into. But if you go two layers deep, you can suddenly get really interesting themes. And I mean, it's a lot of what I did in my book. I would just like go like this. People say things changed after World War II. Why don't we just go see what people are actually saying at the time and connect the dots that way?

[20:04] Billy Oppenheimer: Yes. Yeah, for sure.

[20:07] Paul: And you embrace the note card system that Ryan is famous for.

[20:11] Billy Oppenheimer: Yes.

[20:13] Paul: How do you feel about fully digital systems?

[20:17] Billy Oppenheimer: Um, I, I think it's like, find what works. The, the thing I often see with the digital system for most people is they just copy and paste things into it for the most part. And I'm a— and Ryan's a believer, and I'm learned from him, is like using time as a filter. So like one of the important parts of the no-card system is after you read the book is like setting it aside for some time. Because if you like, if you've ever like underlined stuff in a book and then you go back through and you're like, actually, it's not as interesting as I, as I originally thought.

[20:54] Paul: This happened to me last week. Yeah, I was like taking, it was like folding down pages and going back. I'm like, why did I highlight this?

[21:01] Billy Oppenheimer: Right.

[21:01] Paul: Not interesting.

[21:02] Billy Oppenheimer: But like the novelty of it, I think, is like Oh, I've never seen that before. I'm going to highlight it. But, but so like for people with digital systems, they're capturing all of that. So then all—

[21:13] Paul: there's no like cutting process.

[21:15] Billy Oppenheimer: Yeah. So when I go back through a book, I might have like half the pages earmarked, but I'm only making like 5 or 6 note cards because it's like, what, what is still holding up is interesting. So that's why I think if you can get yourself to do that digitally, but I think digital just is like, it lends itself to copy and paste.

[21:38] Paul: Yeah, this is ultimately the problem with the digital world. There's, there's too much information. There's no synthesis, right? Yeah. This is the huge upside of writing online. If you can synthesize, add taste or discernment to ideas, you can add a lot of value for people.

[21:56] Billy Oppenheimer: Yes.

[21:58] Paul: So what I sense like working for Ryan is like your version of actually working in banking, right? Or lawyer, except it's aligned with the life you actually want to live. But what I mean by that is you're learning a very, like, it's an intense process. You're getting a lot of reps, right? And this is what I learned in consulting. Consulting was great practice for getting a ton of reps, synthesizing and making sense of information.

I probably spent about like 8 years too long doing that. I could have gotten most of the lessons in 2 years. Yeah. But yeah, what has that been like? It's hard to realize those things in the time too.

[22:39] Billy Oppenheimer: Really hard. But the coolest part of it is, so everything I've written for 4 or 5 years now has had to go through Ryan's filter. When I write a draft of anything, he, he like goes through and is like, it's not there yet. And he'll tell me why. And then I have to like, he doesn't fix it. I have to like keep reworking it until it's ready.

And now I'm— my draft one is further along than my draft one a couple of years ago because I'm starting at further along that spectrum. Like I'm starting closer to like where Ryan wants it. So it's brought my level up, you know?

[23:24] Paul: It's like playing tennis with somebody that's good. Yeah. Yeah.

[23:28] Billy Oppenheimer: And I think like the taste and discernment thing, I think that's one of the ways to develop taste is like getting writing for rejection. Um, so what does that mean? So Obviously when I send him a draft, I think it's good. And if I didn't have to go through him, like if I was still just writing on my blog for those years, I would have just kept submitting like those first drafts that I thought were good. But he's like, nope. And now I have to like rework and rework.

And through that process, now it takes me less time to get through his rejection. But I think it's like if without him editing the stuff, I wouldn't have progressed.

[24:12] Paul: Yeah. Once you experience that too, it sucks when you don't have that.

[24:17] Billy Oppenheimer: Yes.

[24:17] Paul: Right? Like if you don't have people pushing and challenging your ideas, it can feel like, okay, I need to find this. I need to find people to battle test my writing.

[24:26] Billy Oppenheimer: Yeah. Well, I, so I did that piece with Every recently and the best part of that process was like, they had 3 or 4 people on their team giving me feedback. And same thing, like, I thought the first draft was really good, but then they're pointing out stuff that, like, I'm blind to.

[24:42] Paul: Yeah, it was amazing. I saw some behind the scenes too. Your first, your first draft was not that good. It was—

[24:49] Billy Oppenheimer: no, it was, it was a mess. And it was like—

[24:52] Paul: but it had the core argument. You could see the path, right? Yeah. So it's like, okay, there this is something worth writing. And it's like, okay, how do you get it to the endpoint? Is somebody giving feedback?

It's very hard, but it's 90% of it is just knowing how to iterate yourself for sure.

[25:10] Billy Oppenheimer: And their one like sort of major piece of feedback was like, we, we really like it. The argument is solid, but we want more of you in it. And I, I like, like to keep myself out of it for the most part.

[25:22] Paul: Well, you, you have been out of it. Yeah, you're writing. You're writing Ryan's stuff. Yes.

[25:30] Billy Oppenheimer: But even still with my own, I prefer to like tell stories from what I'm reading, not like stories that I've experienced because it's just like less interesting to me. Like what I've— my own stuff.

[25:43] Paul: And you've leaned more into your own writing. What has that process been like in terms of finding your own voice? Because I'm guessing your style is not Ryan's style, right? You can pick up some tools and tricks from him, um, and like general vibe, but yeah, ultimately not your influences.

[26:06] Billy Oppenheimer: Yes. Well, I mean, the, the process has been— and he's been super— it was, it was him that was like a year and a half ago, he was, he was like, if I think you should start putting your own stuff out there, like what if you're still working for me at this capacity and 2 or 3 years, like, we both, we both messed up. And you, like, the way you're gonna progress is if you start putting work out there.

[26:28] Paul: So yeah, this is, this is something Robert Greene writes in Mastery.

[26:32] Billy Oppenheimer: Yep.

[26:33] Paul: Right, about the 3 phases of apprenticeship. Embed yourself in a system, learn the system.

[26:37] Billy Oppenheimer: Yeah.

[26:38] Paul: Um, and then the second step is when people often wait too long, which is like, you need to go do your own thing. And that can take many forms. I think the nature of work and part-time work and all those things enables more ways to remix that. But how are you thinking about that? Like, it's a year and a half after you made that comment.

[26:58] Billy Oppenheimer: Um, I, I'm pretty happy with like, I feel like I'm on a good trajectory. Yeah. And Ryan like continues to be a huge supporter of my stuff, like mentions the newsletter on podcasts and links to it. And it's, it's slowly— my stuff's growing. I'm getting good feedback from people and I feel like I'm finding— I'm just like still obsessed with like the craft of writing. And I still feel like I'm working on that.

And the newsletter has been helpful because it's, it's called this, it's called Six at Six on Sunday. So I'm locked into a publish time. And without that, I could— like, I love it.

[27:45] Paul: 6 PM?

[27:46] Billy Oppenheimer: Yeah, sometimes a little after, but Austin time, you could play with that. Yeah, depending on where you are somewhere in the world, it has to be 6. But, um, because otherwise I could— I love the research and I could just continue to, um— so it's been good to have like the newsletter as a forcing function to like publish stuff and get feedback. And then some of the article stuff I take more time on, but Yeah, I'm just like, want to keep—

[28:14] Paul: And how do you structure that? Like, is that a full-time thing? Like, how do you think about spending your time and working on other stuff?

[28:24] Billy Oppenheimer: Well, like the Notecard system, I've been doing that for 3 years or so. So a lot of the stuff I'm using in the newsletter is like things I taken a note of within the past couple of years. So I have a lot of material to work with and I'm just constantly adding to that like stock of, of stuff. So I try to carve out like an hour or two a day to read and just like consume things that I can use in my own stuff. But then also it's like the work I do with Ryan. Sometimes if I read something that's— I'm like, that's not something he would want to use, but like, I like that.

I'm going to, I'm going to hold on to this. So sometimes like the— my, my— I'm like on the clock for him, but I'm finding stuff I can use.

[29:09] Paul: Yeah, that makes sense. It's great alignment. And I know Ryan talks about this idea of like a collection of influences sort of shaping your own style.

[29:18] Billy Oppenheimer: Yeah.

[29:19] Paul: Who are some of your biggest influences?

[29:21] Billy Oppenheimer: Well, along with, with Ryan and Robert, Morgan Housel is a big influence on me. I sort of— I think he— what he does with like finance and investing is sort of what Ryan does with philosophy.

[29:35] Paul: Yeah.

[29:35] Billy Oppenheimer: Like using, using stories like that seemingly have nothing to do with finance and then tying it back. And I like that style of like a story from like this domain and how it relates to this thing over here. And it's something I try to do. It's basically all the newsletter is, is like 6, like disparate things. But here's the through line between them. Those, those are like, I'd say, And I also, through the work with Ryan, like I'm constantly engaged with Marcus Aurelius, Seneca, epic, like those, I'm always in those books and I see how it is.

[30:10] Paul: Do you feel like you're in Rome sometimes?

[30:13] Billy Oppenheimer: Yeah, no, but I'm like—

[30:16] Paul: Can you picture yourself in that time? I mean, you must get so steeped in that.

[30:20] Billy Oppenheimer: Yeah, it's funny, like, when Ryan and Ryan will call, like, I was just reading meditation, like, you know that passage where Marcus— and then we're like on a first name basis with Mark, and it feels like we kind of, we kind of know him. And I do this with like, um, like I was just reading this Dr. Seuss biography, and my girlfriend and I were like talking about, um, she, she was talking about like potentially like where would you, where would be your dream place to live? And I was like Uh, La Jolla, California.

[30:52] Paul: Yeah.

[30:53] Billy Oppenheimer: And she's like, what? Why? It's like, that's where Ted lived.

[30:56] Paul: Dr. Seuss. Yeah.

[30:57] Billy Oppenheimer: And she's like, who's Ted? And now I like, I do that with the people I read about. Um, but yeah, I do. I, it's weird. I do feel like I know Marcus Aurelius because I just spend so much time with his, his journal.

[31:11] Paul: Nice. I like it. Talk to me about Australia. What were, what were some of the ahas for you when you arrived in Australia? It seems like that was a big mindset shift for you.

[31:23] Billy Oppenheimer: It was huge. And it was big because I went there and just sort of dropped in on— it wasn't like traveling. It was like I moved there. And I was experiencing life in a culture that in some ways was similar, but in other ways was very different. Just to like have that perspective. And one of my first nights in Australia, I was like, so I went there to play and coach lacrosse.

So I was immediately like embedded into this lacrosse team. And a lot of the guys on the team were about my age. So like when I arrived, we went and had like dinner and then went to a bar after. And I remember I was like talking to one of the guys or I was talking like some stranger at the bar. And I asked him like, oh, like, what do you do? You must be American.

Like, that was like a giveaway that like I asked him what he did for work.

[32:21] Paul: I feel like this is a universal experience for Americans abroad, really realizing how obsessed we are with work in this culture. Yeah.

[32:28] Billy Oppenheimer: But it was also just like, what else was I going to ask this stranger? Like, yeah, you default to like, what do you do? And that quickly like got kind of like expunged from my— like, I stopped asking that. And I still like—

[32:43] Paul: do people have a default question there? What's the latest wave you caught? Or—

[32:47] Billy Oppenheimer: yeah, well, there it's like they don't— no one cares what you do for like the work culture.

[32:54] Paul: Even in like the corporate world, people won't know. Wow. Feels like I should go to— I should be sending some books to Australia.

[33:02] Billy Oppenheimer: Well, they'd be like, yeah, we get this.

[33:04] Paul: They're like, what the hell? Why?

[33:05] Billy Oppenheimer: The Pathless Path is like their path.

[33:08] Paul: There's like, what's the default path? Yeah, but I have heard from Australians too that there is a pretty solid, uh, default path there. One friend in Australia told me like the dream is like a second home outside of the cities on the water with a boat. Um, so maybe you just didn't—

[33:28] Billy Oppenheimer: I was in—

[33:29] Paul: I was—

[33:29] Billy Oppenheimer: I was in Perth. I was on the West Coast and like, so I guess if you do research, like the outside. Yeah, like if you do research, like where should I go abroad? And like, Perth will not— will probably not come up. It's on—

[33:43] Paul: that's probably where I'd end up then.

[33:44] Billy Oppenheimer: Yeah. So it was— I think if I went to like Sydney, yeah, I would have met more people like that.

[33:50] Paul: But it's like New York versus Austin.

[33:53] Billy Oppenheimer: Yes. Yeah, definitely.

[33:55] Paul: In New York, they ask you right away, what do you do? I'm like, oh God. In Austin, they're like, I don't even know. They're like, where do you typically walk on the path?

[34:05] Billy Oppenheimer: Your favorite coffee shop?

[34:06] Paul: Coffee shop. Yeah. Where do you go to the gym? Yeah. But yeah, you still have that in Austin too. But yeah.

Any other shifts for you from just living and traveling? And you were working for Ryan while still traveling?

[34:23] Billy Oppenheimer: Not in Australia.

[34:24] Paul: So you came back to the US, you started work for Ryan and you sort of stayed in the US?

[34:29] Billy Oppenheimer: No, then I was in New Zealand for winter.

[34:31] Paul: So you were still traveling a bit. What was that experience like? Working for somebody you admired and basically doing what you wanted most days as well?

[34:42] Billy Oppenheimer: I think I was like— it was interesting because I was prior to the work with Ryan, I was like very addicted to skiing. And it was interesting to see that that was like turning off. Like I was like, I actually don't want to go ski today. Like, I'd rather read this book.

[34:57] Paul: Wow. What do you think that is? You think that's just the power of like the creative act?

[35:02] Billy Oppenheimer: Maybe.

[35:03] Paul: It's—

[35:04] Billy Oppenheimer: I feel like I also had like 400 straight days of skiing, so I think I was getting quenched to like— yeah, I think I was like scratched the itch.

[35:12] Paul: But skiing is something that hardcore skiers can do this forever.

[35:17] Billy Oppenheimer: Yeah, well, I mean, I'm going next weekend. Like, I still, I still love to do it, but it was—

[35:22] Paul: the optimal amount was not zero skiing for you. Yeah, yeah.

[35:25] Billy Oppenheimer: Um, like one weekend a winter is— now I'm good with that.

[35:29] Paul: Really? Yeah. Wow.

[35:31] Billy Oppenheimer: But it was, it was interesting to see, um, like it was all I, I did, thought about. I like would come home from skiing and like watch YouTube of like skiers, and I was very obsessed with it. And then, and then suddenly not.

[35:46] Paul: Yeah, it was just you were enjoying the other work you were doing. You were excited to wake up and dive into that. Yeah, go into ancient Rome.

[35:55] Billy Oppenheimer: Yep.

[35:56] Paul: With your buddy Marcus. Yeah. Yeah.

[35:59] Billy Oppenheimer: And I was, I was getting really interested in like in the way that I once was obsessed with like getting better at lacrosse, for instance. Like I was, I was aware that I was having that same feeling towards writing and I was wanting to like the time that I was spending on skiing, I'd rather work on the craft of writing.

[36:20] Paul: And you still enjoy it?

[36:22] Billy Oppenheimer: Writing?

[36:22] Paul: Yeah. Yeah. Oh, yeah. What, what about it?

[36:27] Billy Oppenheimer: Do you know, like, that— so the, the psychologist Scott Barry Kaufman.

[36:33] Paul: Yeah.

[36:34] Billy Oppenheimer: I heard him recently talk about how, like, they, they somewhat recently, like, discovered there's, like, a dopamine pathway that he calls, like, the nerdy, the nerdy pathway. And you get, like, a dopamine hit from, like, information. And I feel, I like think I've got that. Like when I get excited about like this idea and like, oh, I read this other story that, and putting those together and then trying to like put that in a format that in like the written form is really exciting to me. And so like on a Sunday, if I have it my way, I'm just like in my room with no cards trying to do that. And like make those connections and I get like pumped about it.

[37:16] Paul: Totally get this. Yeah, I'm wired the same.

[37:19] Billy Oppenheimer: Yeah, the nerdy pathway.

[37:20] Paul: I have the nerdy pathway. Yeah. Yeah. So we're info drug addicts.

[37:26] Billy Oppenheimer: I think so.

[37:27] Paul: Who just happen to be alive when this sort of addiction is high status.

[37:32] Billy Oppenheimer: Yes. I actually heard David Foster Wallace talk about this where he, he was doing research and he was spending time in halfway houses. And he was like, he could see what they— their addiction to like drugs. He was like, because of where I grew up and all I had around me was books, my compulsion is for books. And he like identified a similar compulsion, but like it's just like what happens to be around. And for him it was books and for them it was, yeah, it was something else.

[38:02] Paul: But do you think we all need something like this? And like, that's what's getting so many people addicted to social media, just because like there's a deficit of maybe healthy addiction.

[38:14] Billy Oppenheimer: Maybe. Yeah, yeah. Like, for, for me, it was like that obsessiveness for a while was, was directed towards skiing, and now it's, it's been replaced by something that seems to me to be more important.

[38:29] Paul: Um, well, also as positive externalities Yeah, right. It might enable you to—

[38:34] Billy Oppenheimer: I don't even make a living.

[38:35] Paul: It might enable you to make friends. But yeah, go ahead.

[38:38] Billy Oppenheimer: I don't even mean like it is objectively more important. Like, I just mean like for some reason in my mind I'm more interested in this, and that's where— yeah, now I'm like, I don't think about skiing, I think about this thing.

[38:51] Paul: Do you think you'll lose this by something else in the future?

[38:55] Billy Oppenheimer: I'll never say never, but I do— I think to me it's a good sign that like I want to spend— I do not want to go out tonight because I want to be able to wake up early and like read and make note cards. And I'm like excited that like that's a thing.

[39:09] Paul: Reading and making note cards on a Saturday morning. That can be the title of this episode. Yeah.

[39:15] Billy Oppenheimer: Yeah.

[39:16] Paul: I think there is like this creative act of continuing to show up and write. There does seem to be something that feels inherently sustainable. To it. Like, I feel good and nourished and energized after I'm doing these things. Do you feel the same?

[39:33] Billy Oppenheimer: Oh yeah. No, it's like I sometimes— um, yeah, it's like hard to fall asleep because you're just— you've got a few ideas that you're trying to string together. And, um, yeah, sometimes I wish I could just like turn, turn that off, but I definitely feel that.

[39:54] Paul: Yeah, one way to cope is just to find all the other ideas people. Yeah, this is why we've connected, right? I think it's, it's been so cool for me to meet other people like you. For 10 years I lived in the corporate world where people were not these ideas, didn't have the nerdy pathway, right? And people would kind of dunk or say cynical stuff when I'd bring, isn't this amazing? Isn't people like, ah, you're full.

And like, I learned to like suppress and quiet that. And I didn't realize there were so many other people with this same nerdy pathway in the world. I think writing online and sharing ideas helps you like quickly find the others because you put these ideas out there and people are like, oh crap, you too? Yeah, yeah.

[40:44] Billy Oppenheimer: No, it is, it's like a magnet for So my, like, recent rabbit hole I've been going down is animal courtship. Animal courtship, like animals in, like, the natural world, like how they attract a mate.

[40:57] Paul: Have you seen the Ricky Gervais standup on this?

[40:59] Billy Oppenheimer: No.

[41:00] Paul: Oh, you have to watch that.

[41:02] Billy Oppenheimer: But it was like, so the bowerbird, for instance, like builds these elaborate bowers, they're called. They're just like nests and they like decorate them with, with they'll like paint them with cherry— like they'll splatter cherries on it and like paint it. And the like precision of the geometry of like how it appears to the female— the female is like trying to get a sense of like, is this bird smart enough to like take care of us, you know? But I was like, I'm— as I'm reading about, I'm like, oh, this is like—

[41:33] Paul: so they need to understand Euclidean geometry.

[41:35] Billy Oppenheimer: Yeah, it's very wild. It's like very complex what they do, but it's like to show what they can do to attract people with like, oh, I like these colors you used in this bower. Like, let's hang out. And I read that. I was like, it's kind of like what's been happening to me is like putting stuff out there, what I'm interested in, what like I can do. And it's like attracts people that have similar interests.

[42:03] Paul: Yeah. So we're all just bower birds putting our geometric shapes out into the world.

[42:08] Billy Oppenheimer: They all are doing something like that. Like peacocks.

[42:10] Paul: Yeah, I love it. Any other mating rituals?

[42:17] Billy Oppenheimer: Oh, bird-of-paradise. If you like search YouTube for bird-of-paradise dancing rituals, they like learn from their father a dance, and then they like choreograph it, and then they like practice and wait for a female to come and like show them what they can do. And there's like funny videos where like the bird watches and then flies away, and like The narrative is like, even when you put on your best performance, it doesn't always work out.

[42:44] Paul: Wow. It's so good. This is such a good metaphor for writing, right? It's like you think you ship a banger and then nobody says it. Exactly.

[42:52] Billy Oppenheimer: Exactly.

[42:54] Paul: That's amazing. So when you said in your same interview, senior year, it looked like it was this trivia. You said if you had $1 billion, Yeah. And you had made it, you would go to the mall and buy a bunch of stuff. And then when you were checking out, you would say, hold on, anything my boys want.

[43:17] Billy Oppenheimer: So yeah, that sounds about right.

[43:21] Paul: Whatever. Whenever I was— whenever I made it, I would take care of—

[43:26] Billy Oppenheimer: I still have that, like, dream.

[43:27] Paul: Yeah. Yeah.

[43:28] Billy Oppenheimer: I've just like, it's all me, boys.

[43:32] Paul: And have you started to embrace any of this? Like, are there ways to inject that now? Because I don't think you need a billion dollars to like buy what your boys need in the store.

[43:42] Billy Oppenheimer: Yeah, no, I mean, I, I would want to do like, guys, like I booked this cabin in Montana for the week on me. Flights are booked. Like those sorts of things, like experiences where we can— because we're all sort of like spread out now. So it'd be cool to like on my dime, bringing everyone together would be cool.

[44:05] Paul: I love that idea. Uh, what, what have you seen? I know Ryan is built out of a team and you've gotten a front, uh, eye view on that. Yeah. What have you seen in terms of the kind of people that succeed in this type of environment?

[44:25] Billy Oppenheimer: Um, people who are already doing the thing before Surf of work. And it doesn't even have to be like— so one of the things Ryan liked about me was that I was writing this blog into the void. And to him it was like, yeah, that showed pure motivation.

[44:40] Paul: Like, I love that.

[44:41] Billy Oppenheimer: He doesn't need to see you published in the New York Times. He's like, are you just like doing it because you like to do it? And it's almost more impressive that you're doing it with no one reading.

[44:50] Paul: He didn't know about your uncle though. No, he didn't.

[44:54] Billy Oppenheimer: He didn't. Um, but that, um, so like when he was hiring someone for the bookstore, he hired this girl who had this blog where she reviewed books just as an excuse to like reach out to publishers and say, I review books, can you send me some? And it would like fund her, her reading. And she— and Ryan was like, done. Like, he loved— so like those sorts of things, people not waiting for like permission to do it. but they just are like, they have this need to do it.

[45:24] Paul: And what are the things you've all learned as a team in terms of what you— I think Ryan, other people in the creator economy are really creating these new sort of media.

[45:35] Billy Oppenheimer: Yeah.

[45:36] Paul: Um, teams. And it's really hard, I think, from talking to people. But what are some of the things you've learned, um, from your perspective?

[45:45] Billy Oppenheimer: I think it's been helpful to like just have people own one part of it. So early on it was like I was juggling the, the podcast, the email, his personal stuff, and it was— I was just sort of like, it was hard to handle all that. And then when we bring someone on, it's like, all right, you're main— all your— you're the YouTube guy, you're the podcast guy.

[46:09] Paul: Specialization works.

[46:11] Billy Oppenheimer: Yeah, just being able to— because And everyone on the team has like their own— I'm not the only one that's like trying to do my own stuff creatively. So like, can people just like own one part of it and then also be able to like get some energy from doing their own stuff?

[46:30] Paul: What's something that surprised you working with Ryan that you couldn't have predicted?

[46:36] Billy Oppenheimer: His— so if I didn't see the way he is day to day, I would think he was just always like at the computer writing. But it's, it's not. He's like, he's living a life. If you ever go over to the books, like the Painted Porch where his office is, he'll be like in his office for like 10 minutes and he'll write a Daily Stoic email. And then he's like downstairs on the back porch, like with his kids, comes back up, writes something, loads them into the stroller, goes for a walk for like an hour. Comes back.

So he's like in and out. He's doing stuff. It's not like 8 hours in front of a computer screen all day, which I would have assumed.

[47:16] Paul: Yeah, that's interesting. I think from reading his stuff, I picture like he wakes up and just like locks in for 4 hours.

[47:22] Billy Oppenheimer: Yeah, he's like a very efficient writer. So he can like— if you ever see him in a Google Doc just writing Daily Stoic stuff, it's like It's as if he's transcribing something. It's nonstop. And then you like click, click, next line, like mic drop, next thing. And he can, he can like bang out and they're like really well written. Whereas for me, if like he's like, hey, could you draft up something quick for like this Daily Stoic thing?

That might take me 2 hours because I'm like, to get ideas clear in my head takes a long time. But he's just like very fluid.

[47:58] Paul: What are some of the opportunities you're seeing given— I mean, he's, he's a larger creator. There's many that are running even bigger enterprises. But what are some of the opportunities you're seeing? I think one thing I always struggle with is I'm sort of playing the solo game. Yeah. And I don't even know what opportunities I don't know about.

Right. So like How are you all— like, do you guys have strategy meetings about, like, no, talking about these things? It's sort of just like Ryan. So he's still kind of running it in solopreneur mode in terms of, like, his instincts and direction?

[48:34] Billy Oppenheimer: For sure. Yeah, it all stems from him. Um, and he, he gets— he has eyes on, like, everything that goes out. So, like, the— you— like, our YouTube producer doesn't ship anything unless until Ryan, like, sees it and signs off on it. So he's still, like, He knows everything that's going on. He gives people like the freedom and like the encouragement and like the, you know, I can feel empowered to like go write this article in like the way I want to do it and then get his feedback on it.

But nothing goes out the door without like him signing off on it.

[49:13] Paul: That's fascinating. What are some of the opportunities in the creator economy you think are emerging?

[49:22] Billy Oppenheimer: Hmm, I don't know.

[49:24] Paul: Um, like, I know you and your team are focused more on YouTube.

[49:29] Billy Oppenheimer: Well, so for us, everything is like, this is on YouTube. Yeah. Yes. I mean, but it's— it all exists to get back to the newsletter.

[49:39] Paul: Yeah.

[49:39] Billy Oppenheimer: Like, we want to get— we want to get people back to the email list, and most of the The content on YouTube, the podcast is adapted from stuff we've written.

[49:49] Paul: Yeah. Well, ultimately it's all driven to get back to books, right?

[49:53] Billy Oppenheimer: Right.

[49:53] Paul: Books is kind of the center of gravity for everything.

[49:56] Billy Oppenheimer: Yes. Which I still think like email, like it should be the focus.

[50:02] Paul: Yeah, that makes sense. Because that's sort of— that's also like an on-ramp to get a taste of the writing as well. Right. And then you might level up. Write the books, but I guess you could serve a lot of people through newsletter as well. Yeah.

What about you? Like, what are your models? Obviously Ryan and Robert are models for you for paths to follow, but also the world is changing. What sort of things are you excited to create in the future? Is it books? Is it newsletter?

Other things you're thinking about in the future?

[50:32] Billy Oppenheimer: Yeah, newsletter for sure is like my main focus right now.

[50:36] Paul: Um, do you want to write a book?

[50:39] Billy Oppenheimer: I think so. Like, I have sort of a vague sense that I would like to, but I don't know. It hasn't— I haven't like found the idea that's like consumed me yet.

[50:47] Paul: Sounds like you're like me a little bit. We're just like, yeah, book sounds interesting, but I didn't really know I wanted to write a book until it was like, oh, now it's time. Yeah, the idea has sort of chosen me.

[50:59] Billy Oppenheimer: Yeah, no, I sort of— I definitely believe that, like what we were talking about with like sort of the obsession with this one thing and then that switch. Like, I feel like I will get obsessed with an idea that I will then be— I'll go, okay, I think this is a book, but I haven't found that yet.

[51:15] Paul: Any other threads that you're feeling pulled by now outside of, uh, bird mating rituals or animal mating rituals?

[51:25] Billy Oppenheimer: That's my main thing right now, uh, and that should keep me busy.

[51:29] Paul: There's a lot of animals, a lot of animals living and extinct.

[51:33] Billy Oppenheimer: Well, like my main— I, like Ryan, I mostly read biographies. I'm really into Dr. Seuss, as I said, Charles Schulz, the Peanuts creator, like creators that— like Bob Dylan had that, this line that he was a musical expeditionary, like he just liked to like study the great musicians before him. I feel like I'm trying to like read about all, all my like creator heroes right now.

[52:06] Paul: That's awesome. Yeah, it seems like we've lost touch with this, or maybe this is a huge opportunity too, because I think listening to David Senra's Founders Podcast—

[52:19] Billy Oppenheimer: so good—

[52:20] Paul: you realize A lot of these people were using previous models from previous generations, many of which we've never heard of.

[52:28] Billy Oppenheimer: Right.

[52:29] Paul: Right. And it almost seems like in the modern world, we're so caught up in the never-ending now that we're not looking to these models. But there's so many interesting examples. And just like you can have your writing style guides, you can have sort of your life models. And I sort of realized I unconsciously have been doing that over the years.

[52:50] Billy Oppenheimer: Yeah, I can't think of any— like, all of my favorite— and it doesn't matter, domain, musicians, filmmakers, they all talk about just being students of the history. And it was like they became obsessed with the thing. Yeah. And it's like, all right, for some reason the instinct is like, let me go, who is the best before me? I want to like learn from them. And I've seen that in like every— everybody I've been drawn to has a similar impulse to go like, Like David Sander is a great example, and I talk to him about this a lot.

Like, I send him like examples of people talking about calling them— like, uh, Quentin Tarantino calls himself a film historian, and he's like, no one paid me to do it. I was just like, in my mind I am. And I see this like musicians, athletes. So that's— I want to just like go deep on, on some of—

[53:40] Paul: who are some of the most interesting examples of like the modern— like, what is an archetype of modern creator? Can follow because the lessons are really the same. It's just like channels and media. Yeah.

[53:52] Billy Oppenheimer: Um, let me think. Like, sort of a cliché one is Walt Disney. Like, he kind of was doing a version of— in, in the way that creators like branching out into like YouTube and podcasts, like he was doing that.

[54:08] Paul: Yeah.

[54:08] Billy Oppenheimer: With—

[54:09] Paul: well, at first he was just a freelance Cartoonist. Cartoon designer, right? And he was just doing it for other people.

[54:15] Billy Oppenheimer: Yeah. But then there are also like Charles Schulz is sort of the opposite of that where he was like, I just love cartoons. I'm not going to go anywhere outside of this. And I kind of like, that's kind of like a Robert Greene type. Like he's just like, I love books. Um, and he has, he, people help like take his, his video stuff and get it on, on other mediums, but Robert is just like a single focus on the written word.

So I think there's like— and Ryan's more of like a Walt Disney type, I feel like. And I think me, like, I would lean towards Robert in this way more. Like, I would rather just focus on books and the written word and not get too distracted by video.

[55:03] Paul: Yeah, like me. Well, I don't know. I'm just saying, like, I actually like doing a variety of different things, and I think I used to try to talk myself into, oh, what if you did one thing and went all in? Yeah, I never liked that. I don't— I lose energy.

[55:22] Billy Oppenheimer: I'm like, you're like, I've tried on that, it didn't work.

[55:26] Paul: Yeah, exactly. And maybe I'm lying to myself, but well, the book, I did sort of go all in on a year, but during that year I was also learning Chinese and running some training programs with companies on teaching consulting skills. Yeah. So it was like that, that felt like a very alive mix for me.

[55:46] Billy Oppenheimer: Well, so this is back to like the, the influences thing. I also think part of that is like if you step back and like, why am I drawn to these? These types of people, you can learn a lot about like what you should pursue. Like, why do I like this person's work so much? There's probably something like I can learn from that.

[56:04] Paul: Have you read Luke Burgess's book Wanting? I'm reading it now and he talks about this, right?

[56:09] Billy Oppenheimer: Yeah. He really brings that desire.

[56:12] Paul: Yeah. He brings it alive better than anyone I've ever seen. I'm only halfway through the book, but it's so good. And he's talking about— he's like, the people you're attracted to can give you information, right? Mimetic desire doesn't have to be bad. There's a dumbed-down version of it where you can just like want the big house because everyone wants the big house.

But you might be inspired by somebody and you can use them as a model and just really self-reflect and say, okay, is this making my life better?

[56:41] Billy Oppenheimer: Yeah, I was listening to Andrew Huberman on a podcast recently and he said when he was in, in grad school, he was like basically in isolation, like in his lab. And he made a list of his favorite, like, scientists that he had read about, and he hung it up in his office. And he was like, I later came to find out this is what's called introjection.

[57:03] Paul: Introjection? Introjection. Did he make that up?

[57:05] Billy Oppenheimer: No, it's a real thing.

[57:06] Paul: Oh, wow.

[57:06] Billy Oppenheimer: It's like, so it's the process of, like, inheriting the qualities of others. And, like, reading does this, but also just, like, having for him, that list of people that he's constantly thinking about, like, what do I love about that person? And like, that's becoming part of him.

[57:22] Paul: I love that. Um, yeah, I, I was just, um, with Danny Miranda, I was telling you, and he said something to me a few weeks ago. He's like, Paul, I think your book's gonna sell a million copies. And I'm— I, I found that really interesting because I wouldn't generate that thought.

[57:43] Billy Oppenheimer: Yeah, but now it's in there.

[57:46] Paul: So I'm asking myself, what would it take for me to— like, how do I— how would I even arrive at such a thought? Like, I just don't have these natural ambitious energies. And I think a lot of people who meet me realize this pretty quickly. It's like, Paul's totally underselling himself, or like, yeah, totally missing the obvious opportunity. So I've been trying to like, okay, how do I put on the Danny Miranda mode and think of ways that are still creative and fun and in flow of my life? And it's a really interesting thing to do.

So I've been trying to do that just with some of my friends who think differently than me.

[58:27] Billy Oppenheimer: Yeah, I mean, I find this when, if you listen to a lot of Jocko, you're more likely to like wake up when your alarm goes off and like eat healthy because like part of you is thinking like, what would Jocko do? And I do find that with like podcasts or reading, like some of that you're like consciously thinking about when you're making decisions. You're like, what would Charles Schultz do? He would— okay, I'm gonna do that. But yeah, even just like Danny Miranda implanting that in your head, that works too. Like just conversation, like It's interesting what gets lodged in there from—

[59:07] Paul: How do you think about ambition?

[59:10] Billy Oppenheimer: I really resonated with what you said about like, I tried it on and I like, I'm not a big goals guy. Like I've tried that and I just, I'm not like, I can't remember them or like continue to be aware of them. And I'm more of, I want— and this might be delusional, but it's like I want to just do— I feel like these things I'm doing, if I just keep doing it, good things will happen. And it's like when I've— if I think back to 2, 3 years ago, anything I would have like made as a goal actually would have been like— I couldn't have conceived of better things that happened, you know?

[59:51] Paul: Yeah.

[59:53] Billy Oppenheimer: Um, so it's like what— there's things right now that if I set a goal, like, I wouldn't be able to conceive of happening. And I'm like, I like that. I like that, like, letting that sort of unfold.

[01:00:04] Paul: Yeah, I think that's a similar thing for me. Um, I think you wrote somewhere that the creative act is about not knowing what's going to emerge, right? Um, I don't, I don't remember exactly where you wrote this, but it's like kind of the joy of finding out, right? Yeah. Yeah. I think I'm way more inspired by that in my own path than like having a goal.

Goals are so boring for me. Like the million books is interesting because it's like, well, that would— okay, what behavior should I change? But I can't be driven by that. That does nothing for me.

[01:00:44] Billy Oppenheimer: Yeah.

[01:00:45] Paul: But I think like you, like I'm sending my newsletter tomorrow and I have like a couple ideas. I'm like, all right. We want to like tie these out, like finish the writing. I can only think like 1 or 2 weeks ahead of time with work.

[01:00:57] Billy Oppenheimer: Same.

[01:00:59] Paul: Yeah.

[01:00:59] Billy Oppenheimer: Do you know the like lead versus lag indicators?

[01:01:03] Paul: Yeah. Yeah, of course. I used to work in the business world.

[01:01:05] Billy Oppenheimer: Right, right. So this is, this is your lingo. I really like that concept of like lead measures or like so, so in the example of like Danny Miranda saying like a million copies. So like that would be like a lag measure. But like, what are the things you can do that would actually like make that kind of, what's the word, not obvious to happen, but like that would be a natural unfolding because you're taking these lead, you're using these lead indicators that you're doing like on a day-to-day basis that it's just like a matter of time for that to happen. So I like to think about that.

And I feel like some of the things I'm doing, like the note card system, I think of as like, these are like lead measures. 'Cause what this note card I'm making is gonna pay off at some point. I don't know when, but I'm going to use this.

[01:01:49] Paul: Yeah, I, I love that. I think for me, it's— I think about I was on a path I didn't like and didn't want to stay on. So the biggest goal for me is to avoid being on a path I don't like, right? So that's self-awareness. I'm on a path I like now, and I think a lot of it is just like intuition and vibes, right? And the lagging indicators are often things like your uncle saying, this is good.

And you being like, oh, people like this. And then like people reaching out and saying they like it. I actually got bolder with putting my book out into the world after many people were like, this is a good book. Yeah. Now there's some fear stuff there probably I need to work through. But yeah, it was like, oh yeah, all right, something's happening here.

I can't cool. I don't quite know where it's going, but it's just like I just need to play the game I can play, which is just keep writing. That's super easy for me. Yeah.

[01:02:49] Billy Oppenheimer: And I mean, that the book is at 12,000+ copies without you thinking once about like, how do I market this thing? That should be to you, it's like, okay, this is helping people. Maybe I should actually put energy into it because like you almost— it's Now it's like, you should do the work for like more people to know about it, 'cause it's obviously working.

[01:03:12] Paul: Yeah, this is the thing I'm sitting with now. It makes me uncomfortable you saying this.

[01:03:17] Billy Oppenheimer: Yeah.

[01:03:19] Paul: But yeah, we need, we probably both need like an ambition coach.

[01:03:25] Billy Oppenheimer: Danny, if you're listening.

[01:03:27] Paul: Danny can be our goal coach.

[01:03:28] Billy Oppenheimer: Yeah.

[01:03:29] Paul: He'll just be like, million, no problem, you'll pull it off. It's gonna be great.

[01:03:33] Billy Oppenheimer: Yeah, I don't know. I actually don't want that.

[01:03:36] Paul: No, no, no. I think that there's downsides to fame, right? Have you seen that, um, with Ryan? Any of the downsides of that?

[01:03:45] Billy Oppenheimer: Um, people just like coming to the bookstore and expecting him to like drop what he's doing to talk to them. And it's like, if he gives everyone that stops by 20 minutes, like, his week's gone.

[01:03:57] Paul: Yeah, he wouldn't have a life.

[01:03:59] Billy Oppenheimer: I know. And not— people don't see all the others that come by and try to do the same thing. So it's like they take it like personal, and it's a tough spot because it's like he has, he has work to do. Um, it's not like that he doesn't want to, but— and I— yeah, I don't know. That's— that always, when it happens and I see it from afar, it makes me uncomfortable. Um, but I mean, aside from that, I don't I've not really seen.

[01:04:25] Paul: Awesome. What— where should people go to learn more about Billy Oppenheimer, what you're working on?

[01:04:35] Billy Oppenheimer: And I have a website, billyoppenheimer.com. I'm on— I'm pretty active on Twitter.

[01:04:42] Paul: You're not related to Robert Oppenheimer?

[01:04:46] Billy Oppenheimer: No.

[01:04:47] Paul: Okay.

[01:04:48] Billy Oppenheimer: I always get like people like ask this.

[01:04:50] Paul: That's a good book. Oppenheimer. Yeah, I think I recommended it to you before. But anyway, Billy billyoppenheimer.com. Um, Six at Six, 6 PM Austin time, or wherever Billy happens to be on Sundays. Yeah, check it out.

Um, always really interesting stories. I love your writing. It's super, um, it's tight. It does remind me of like Morgan Housel, so it's good stuff. Keep going, man.

[01:05:14] Billy Oppenheimer: I appreciate that.

[01:05:15] Paul: And Twitter, do you want people to follow you there?