The pseudonymous figure talks fame, life decisions, and podcasting.
Jake is a pseudonymous blogger and podcaster who has published under the name ‘Blog of Jake’ since he left his job in investment banking. He also has a podcast called Pod of Jake, where he’s interviewed dozens of outstanding figures moving the world forward. He’s incredibly unique in that he’s managed to build a brand anonymously in a world where being online seems to come at the cost of privacy.
Jake
Alex: [00:00:00] Jake is a pseudonymous blogger and podcaster who's published under the name blog of Jake since he left his job in investment banking. He also has a podcast called Pod of Jake where he's interviewed dozens of outstanding figures moving the world forward. He's incredibly unique in that he's managed to build a brand anonymously in a world where being online seems to come at the cost of privacy.
He's a guy I really look up to and I had a great time chatting with him. We talked about fame, life decisions, and podcasting. Hope you enjoy.
Cool, man, you want to jump into this?
Cause I've got, I've got quite a few questions here.
Jake: [00:00:41] Yeah, let's do it.
Alex: [00:00:41] All right. Awesome. You know, I I'd say like, first of all, it's a bit, yeah. An interesting dynamic talking to you because usually whenever I hop on a call with anyone just to like pick their brain about whatever I'm able to do research beyond what they do and some of their work online, like, I'll understand like, oh, it's this person they're from here.
There's some context given to that. And obviously it's like not really doable with you because you're, you've chosen to have this pseudonymous personality online, which I think is a really interesting choice, especially in an age where you know, many of us are so like an inclined or almost there's such an emphasis on, on building some sort of likeness online or building like a personal brand.
And you've managed to do that without actually sharing your identity, which I think is really interesting. So I know you've touched on this before, but I think it's really crucial to the whole. The whole talk here is what was that decision like to, you know, refrain from saying, Hey, my name is whatever, this is me online, and then build a brand off of that.
Jake: [00:01:51] Yeah, that's a good question. So it's funny because sort of the way that things develop can be so different from the way or the reason why they started. I've spoken about this, like you said, a couple of times before, I'm going to try to take a little bit of a different angle here just for the sake of, you know, not becoming a broken record and start conflating this story for that I tell with like what actually happened.
Maybe I'll, I'll do a couple of sort of diverse takes. So I've talked about how I sort of started by you know, why I started by, by being pseudonymous or anonymous. I don't even think I knew the word synonymous hardly at the time. I just thought of it as being anonymous. But I did have this sort of brand with the blue dot.
Use a name, Jake, you know, and that's, you know, that's my name. My first name is just popular enough where it can be synonymous without a last name. And so I started out that way more or less you know, maybe a number of reasons and maybe just an instinct, but one of the like silly reasons they're not silly, but like you can get a sense of how this develops in a sort of weird way.
Like part of the reason I started that way, it was just because I had just quit my job in investment banking. And I didn't want people like looking up, you know, what I was doing after quitting. And, you know, my old boss is seeing that I'm writing about like philosophical stuff on some like random blog and like, you know, still out of work or whatever it is.
I don't really care about that so much anymore. It's just, it's not that I care for him not to see it. I just don't really think about it anymore. It's been a couple of years now and I don't, you know, for better or worse, I don't really think about my resume too much anymore. I don't even really think about like, obviously I've, you know, friends in a social network from, in the real world who knows my real name.
They know what I'm doing with the bog yeah. Podcast. But if you don't sort of mix the two, you know, your, your online presence and your in-person presence and who you are and who you've been in your past and everything, you'd be surprised. It's like, you know, I haven't been exposed yet. I'll put it that way.
So I appreciate it sort of your, your compliment on like must be a little bit difficult to like, to your point, it's, it's easier to build a brand on sort of your likeness and like the biggest piece of your likeness, or at least a huge piece of your likeness is like your face. Yeah. And if you don't show your face, people don't really have like this, you know, they just like, can't really think of you.
It's like hard to like think of a voice or like, whatever. So, I mean, I have the blue dot there. Like maybe people can think of that, but it's just not as easy to attach to. It's not as easy to like trust a faceless. So I do think it was sort of, if you were trying to build an audience as quickly as possible, I think it was probably a counterproductive move.
And something that probably has and continues to slow, like for example, the popularity or audience growth of of the podcast or my blog or my Twitter or whatever it is. But I'm sort of the past for me, at least, and, and sort of what I wanted to do. I'm not shouting into a void or writing into a void anymore.
Like people do listen. People like you will reach out from time to time. And it's all, it's all become very, very worthwhile. And I wouldn't consider sort of using my face and full, not full name anytime soon for, for the reason of sort of like growing more quickly or something like that. Yeah,
no, it's interesting the way you put it in terms of, you know, your unlikeness being sort of an advantage in that way.
And I think about that a lot. I think. You know what fame entails a lot, and I tend to split it into two categories, but I think you're a good example that it can be sort of split again. And that's just in the sense that I feel like there's two halves to it. Right. You have your name and you have your face.
And so you have I always give the example of like George Clooney, very recognizable face, very recognizable name. That's like sort of your classic movie star sort of persona. Whereas, you know, the worst case scenario in my mind is being recognized, having a recognizable face, but not having any name recognition in the sense that you don't get.
You're not afforded the you know, the, the luxury of like privacy, but you're also not afforded the advantage of having any sort of leverage with your name. And then on the other end of the spectrum, which in my mind is like best case scenario. I think some people might disagree is are people like George Soros or like Wes Anderson?
Where if, if you saw these guys walking down the street, like you would have no idea who they are, but you know the name instantly. Right. And I think you're sort of proving in many ways that you can split that again, because there's no likeness right in front of the camera here and there's no full name.
It's just it's Jake. So I think this pseudonymous thing is interesting. And I think it's, it's sort of, it seems like a newer phenomenon in many ways. I don't think that was really a thing before. But I've got to ask, is it, is it like a privacy thing? Cause it doesn't sound like it's started off on that.
It's just sort of a buffer for you professionally.
No, it, it, it is. So the part that I probably have talked about a little bit, but I'll, I'll mention here, it directly relates to like what you just said. I did think early on, you know, so I don't start things. I think this is a general rule. Like I don't start things I don't expect to become, you know, big and successful for the most part, you know, alcohol, like, I guess there's probably exceptions that are, but when I started the blog, I expected to write a lot.
I expected in, you know like ultimately for a lot of people to end up reading it. I dunno if that was going to be in a year or after I'm dead, but eventually, like, I didn't expect to be totally irrelevant. And so I did have privacy on my mind. And what you mentioned about like, you know, being recognized in public being, I think it's pretty undebatable that that's maybe for like, Some people it's, that's a good thing or whatever, but I think for the vast majority of people and myself included, that is like a major, negative repercussion of, of you know, being, you know, sort of an outer or being famous basically, and I think that it's, it's easier to sort of have that issue, that what I would call a problem than than most people think you don't actually have to be George Clooney.
Right. Especially the way that things work today, if you have 20,000 followers on Twitter and you know, you live in New York city, you'll probably get recognized. And, and the reason I think that I don't know, like from experience or anything, but you know, how many people think about how many people do you know, like that you've actually met, like throughout your lifetime, from like high school and grade school and college and work and, you know, family and friends and friends of friends and all of these people.
You know, thousands of people, but not like a hundred thousand people. Right, right. But if you've ever spent time in, in a major city, in New York, Chicago, LA, San Francisco, whatever, you know, you'll, you'll run into people. You recognize who, who recognize you. And so why shouldn't the same be true for having 20 or 50 or a hundred thousand followers.
And I, you know, in a couple of years or whatever, I have 2000, it's not 20,000 or a hundred thousand, but these things grow. And it's, you know, you can only, it's sort of an irreversible thing to share your face and your full name, whereas you can always choose to share later on. And so I sort of preserve that option from the beginning, pretty consciously for a lot of the reasons that you mentioned.
And I do think it's valuable to sort of have that process. And it's interesting. I never, I guess I've not explicitly thought about like splitting the name from the face in the way that you sort of described, but the ideal to your point, something I have thought a bit about is like, how can you leverage sort of popularity or fame without, without sort of that sacrifice on privacy.
And so even like, it's actually just really hard to be synonymous. And then, like I said, I'm not Satoshi or anything. Like plenty of people know who I am and what I'm doing like Satoshi is like, and maybe some people know about him too, but at least it hasn't gotten out yet. And there's a lot of reasons that it would have gotten out if people knew.
So he did like a really good job with it. I've met a little softer if someone really wants to spend the time, they may or may not be able to figure it out. I think I've done a pretty good job, but but basically like it's, the world is not built for people to be synonymous. There's no, your customer information.
You know, it's just, it's not easy. Everyone has a camera. If someone sort of figures out that you are who you are and wants to take a picture and reveal that, and they're right, then, like you could deny it or whatever, but like that's sort of it. But I think one of the things I think about a lot is like, there's actually pseudo pseudonymity is a spectrum.
So like I said, it's Toshi Nakamoto is on one end of the extreme where it seems that no one knows who he is or was. And I'm pretty far along that side of the spectrum, but there's also like, you know, so lady Gaga, right? Like, I don't know, I've used this as an example before, like, I don't know her real name.
I know it's like out there and I can find it with a Google search, but I don't care. So I don't know it. And basically to your point on like name and face, I've sort of flipped that where like people, if they really, really want, you know, it's not a Google search, maybe eventually it will be. If I got it's like exposed to whatever.
It's, it's a lot harder than a Google search to figure out who I am. So if you really want to, maybe you can, but at the very least, like I'm not going to be recognized in New York, not anytime soon, at least even if I had 20 or 50,000 followers. So it's an interesting dynamic and you know, for people who, who want to do this sort of thing, and it's, you know, they're not that far along yet.
If, if these are the sorts of things that sound interesting to them, that they agree with, I recommend sort of starting from scratch and biting the bullet and doing it for sure.
Alex: [00:11:24] And moving along there, like to your advice for people that wanted to start at you yourself took a bit of an unconventional path here.
Again, another thing you talk about a lot, so if you want to take a different angle here, that's fine. But it's, it's I think difficult not to mention, right? Like you, from what I can tell were coming out of college or whatever, in a pretty Typical path, you know, going into investment banking, doing that for a few years and then ultimately coming to the decision to quit.
And you know, from, from what I've read and heard you talking about, it was basically just like, okay, it kind of felt like the right time to do it. Everything was in place. You wouldn't be screwing yourself or anybody else by leaving at that time. What was it in you? And I think this goes a little bit deeper into just general, like decision-making when it comes to larger, more weighty, substantial decisions in life like that, what was it in you that sort of compelled you to do that?
Jake: [00:12:19] So, I mean, I'll start, you mentioned framework, I'll start with one that was useful. It was definitely a combination of a lot of different factors. Like I mentioned, a bunch of which were practical, like just the fact that you know, oh, I had just gotten my bonus, which in banking is like 50 plus percent of your overall compensation for the year.
And, you know, so if you leave halfway through the year, halfway through your bonus, you're leaving like a quarter of your, you know, a quarter of your, a year of compensation on the table, basically that you've sort of earned if you allocate the bonus over the portion of the year. It was a good time for me in terms of like my deals, where I just closed a couple of more deals.
And so leaving my group, I wasn't sort of screwing anyone or my individual teams. And not that, you know, I think a lot of people you gotta do what's right for yourself at the end of the day. So you know, had that been, not the case. I think I, I hopefully would have sort of had the. Enough like self prioritization to, to go and sort of manage the situation fine and do it anyway.
It's not like, like, I think a lot of people just they worry about what other people think too much at the end of the day. Like you could say that it would be, there's a little bit of a tangent, but you could say that it would be selfish of me to leave my team and like have them pick up the work on deal flow or whatever.
But it's not really that that's not really the issue. And in my opinion, it's, it's still, it's, it's always selfish because basically I, I don't really care. Like, I mean, I, I do care about these people or whatever, but the, the real reason I would be, it would be basically an excuse because I care what those people think of me.
I wouldn't want them to not like me for leaving. That would really be the root of it. So anyway, this wasn't really a factor cause it was a great time. That dimension my lease was running up, so I didn't have any big recurring expenses on the books, so I could sort of quit and not have the the income coming in.
And, and that would be okay for, for at least, you know, several months or something like that. So a lot of practical reasons a couple of other sort of reasons. So I'd gone into banking in the first place with an open mind. You know, as you know, it's, it's a somewhat traditional, like ambitious person path who, you know, someone who wants to make money and have a good career.
And, you know, it doesn't mind doing the work and everything like that, and sort of a similar story of how I got into it in the first place and everything like that. And I went in with an open mind, some people go in and they start recruiting for the next thing right away. I didn't do that. I didn't want to have one foot out the door on day one.
But I sort of did have this mindset of like, okay you know, after like I'm sort of committing to this for two years, If after that point, it's not something that I want to be doing. Long-term if I realized that, you know, at that point or before that point I'll be in a pretty good situation financially to just leave what, whether I have a job or not.
And so I think the seed was planted from the beginning. And you know, I did sort of come to the conclusion that this wasn't something I wanted to do for the next 40 years. And so as the two year mark sort of approached it, wasn't like one day I woke up and just had this like huge realization. It just sort of got closer and closer to being something that I felt was a reasonable thing to do.
And something that I wanted to do and a risk that I wanted to take. And I had previously dropped out of college after my freshman year. So I sort of had a taste with like going for an untraditional path and just dropping out of something. And I'd taken a little bit more of a risk. So all of that sort of helped as well.
And then the framework you asked for a framework, like one of, one of the big frameworks that actually helped me. Well, two of them I'd say one was Tim Ferris in his book, which I'd read at the time, sort of good timing. His, his book, the four hour work week, he talks about sort of I don't remember exactly what it was, but it had something to do with like the fact that a lot of times seemingly risky decisions, things that you're scared to do are a lot more reversible than, than they might seem.
So I realized like, okay, what's the worst case scenario here. I could probably find another job somewhere within finance. It, it might not be banking. It might be with sort of a worst from, or something like this, but like, I'm not going to be on the streets. Right. Like I'm gonna be able to make some money and I'll be fine.
So that was one and then another was Bezos regret minimization theory or framework for gravity because it basically. He tells this and talking about, you know, when he left his hedge fund job, I think in his early thirties and started Amazon, he basically projected himself forward to like, AJT I think now he does a, he does age 90.
I heard him talk about recently, cause he's a little bit older now, but either way you project yourself really far ahead and think about, you know, w what are you more likely to regret? And I couldn't, I couldn't see a way of regretting that I didn't do a third year in banking. But I could see a way of regretting not taking this leap at a time where everything had sort of aligned and you know, sure enough, two years later, almost as one of the best decisions I've made.
Alex: [00:17:11] That's really cool. That second one, I think about a lot. Just really the sense that there's, there's one life, right. To do whatever it is that you want. And there's, you know, a million different factors that might keep up, keep us in one place or doing any particular thing. So I think it is important to sort of take that deathbed sort of a mentality every now and then, and say, you know, in the grand scheme of things, maybe it isn't that important or in the grand scheme of things will I have actually regretted doing this?
Does this matter that much? That first one is really cool though. The, the whole like fear setting thing, right. Where you're
Jake: [00:17:44] exactly where you're looking
Alex: [00:17:46] forward and basically asking yourself like, Hey, what is actually the worst that could happen here? Like, am I going to end up on the streets?
You know does this actually matter that much? If everything, you know, hit the fan, like what I actually be in that bad of a position and more oftentimes than not, like, I think the answer is no, like your, your, your, your fears tend to sort of Become exaggerated in your head a little bit. So I think that's also a really important exercise to take.
But you know, after having gone through all of this, right, deciding to take that leap, why was it that you decided to start, you know, doing the blog stuff, doing the podcast stuff? Cause I, I think I mentioned like way earlier on when we just hopped on the call. I know for me it was sort of, I still think it's sort of a selfish decision in many ways.
Cause I was never like a guy that was into podcasts. I was never a guy that was like, I'm a fan of the, the medium. I was just really, really interested in learning from people. And the writing aspect of that really helped me sort of solidify that in my own head. And you know, if I could share it with people, I think that was, that was like a, a cool side effect.
But I'm interested why that was sort of what you chose to dedicate a lot of time.
Jake: [00:19:00] Yeah. So for me, it came in like three chapters, the way that I sort of see it. So I started by quitting and I had a one-way ticket to Italy with my girlfriend, like a week after that or something like that and spend a week out there.
And then you know, another week or so in Paris bomb, I said alpha dot point. And at that point I decided I would start writing a little bit. I had previously traveled just after I graduated college, I took a two week road trip with a couple of friends around the states from drove from east coast to west coast over the course of a couple of weeks and just took some notes, sort of like on my phone as I went and not like a lot, but just once or twice a day, like take out the phone and capture some, some highlights or lowlights or interesting things from the day or whatever.
And then when I got back, I spent like maybe two or three weeks, just basically writing that all up into a book about the experience. No, this is not something that I've shared, but it's one of the things that I'm more happy that I've done. It's just really, it's a cool time capsule for me. And I didn't know that I would go on to do the blog and the podcasts, which also serve as like these much larger time capsules in a way, especially the blog where I just wrote like a couple of hundred posts over the course of a year or so, but either way, like really had enjoyed that experience.
And now I find myself traveling again by myself this time. And there's not much to do besides, you know, you can read and write and sight, see and eat and drink and that's pretty much it. So I started riding a bit and then left Europe and went to Japan. And my buddy was coincidentally sort of took a similar path to like banking and but had a more sophisticated plan to spend a year traveling the world.
Decided to meet up with him in Japan and had an awesome time there for a few weeks and then realized like, you know, he was going on to travel the world and I could have hung out with him for a while longer. But but I realized like, you know, I sort of earned myself this free time and I wasn't just going to travel for the sake of traveling.
Like I, I wanted to travel when I quit. That was really exciting to me. And then after a month and a half or whatever it was, I wanted to be back and I wanted to sort of get to work and take advantage of this time that I'd earned myself to try to not just enjoy like some short period, but actually find something that I could do while I had control over where I was, what I was doing, basically everything and enough money to support myself for a while to hopefully find something that I could start doing that could allow me to do that for.
You know, longer than just a stop gap year in the middle of my career or whatever. And then who knows if I'd have sort of the guts to do that again. So as I started writing no, as like a means to make money, but just again, it was sort of the most natural thing I thought of that I could do by myself. I didn't want to just like impulse start a company without an idea that I was super passionate about.
I think I've always thought of myself as like an entrepreneur and founder type of person, but I think to start a company for any reason, other than feeling sort of an obligation that you absolutely have to do it like a responsibility just by how excited about this idea that you are and, and the feeling that you have to do it.
I think if it's anything short of that, if it's motivated by wanting to be a founder, for example, or wanting to not have to go get a job work for someone else, I don't think it's gonna work. Maybe it'll work, but I don't think it's worth the. The challenge of starting a company and the fact that that can be, you know, a multi-year to decade long commitment and struggle for a lot of it potentially.
So I just started writing and I had a lot to, to write unlike traveling when I was just sorta like, write about my experience and go on tangents here and there with the blog. It's a new thing every day. And I just wanted to write and publish something every week day. And like I said, you know, being synonymous and like, there was a handful of people that knew I was even writing and I wasn't really writing for anyone I was writing for myself.
And it's developed over time, but now sort of the gist of it and, you know, learned a lot from writing and just sort of enjoyed the experience as also doing a lot of running at the time. I'm sort of just a building like discipline patients and a number of other things probably that maybe I didn't even realize, but.
After six or seven months that I realized, again, like similar to travel, I could just keep doing this, like riding around in a, but eventually I'm gonna run out of money and I'd want him to start a podcast for at least two or three years. Before I had even listened to podcasts, I figured out I really kinda wanted to start one for the same reason.
You said like how to I'd always been interested in reaching out to people I wanted to talk to. And it's always like, the thing that I wanted to do with these people was like, basically record a podcast, like have a conversation and actually just not have it just be for me, but like share that conversation with others.
And I don't know, maybe like the root cause for that, but there's something certainly beyond the obvious, like I think there's just something cool about that. And and so I started the podcast and then things just sort of took off and I'm not talking about like audience numbers or anything like that.
It's still relatively small the show, but I've been able to talk with 70 plus people at this point in the form of podcast episode, and just so many amazing people who have been really gracious to, to spend some of their time with me. And you know, I'm just super grateful for the way everything has turned out.
And so sort of am where I am now and now I'm actually working as well. But but on something that I'm really excited about and I wasn't looking for a job, I I wouldn't have started working if there wasn't something that, again, I sort of felt compelled to do something that just, I couldn't say no.
Alex: [00:24:55] Did the response catch you off guard at all? Because I know it did for me, not necessarily with like a podcasting thing, but just in the sense of, you know, maybe a year and a half ago now when I started. Actually doing this and taking it a bit more seriously, it being, just reaching out to people who I thought were doing cool things, just to sort of pick their brains about any questions I had.
I was just really taken aback by the number and especially like the caliber of people who were willing to, you know, get back to me or hop on a phone for 30 minutes or anything like that. Did that take you by surprise at all?
Jake: [00:25:36] Yeah. I mean, people, some people are just like really good people, like nice people.
They you know, I, I try to pay it forward as much as I can and we'll continue to do so, but I would say there was half of it that surprised me and half of it that didn't maybe. So the half that did not was like you, I think I had been sort of doing this for years prior. Just reaching out to sort of random people with questions here and.
Like I remember, I trying to think there there's a few now, now they're just all sort of taken over by, by like the podcast that I've just made up, made a real habit out of it. But I had some pretty interesting people respond in the past. I remember like one that comes to mind was the guy from the big shore, like the real guy who Christian bale Pitt plays in the oh yeah.
So I had emailed him in college about something rather like literally like it was like investing in wine or investing in almonds or something. Cause he had this thesis on water. I don't even remember what it was, but you got back. And so I'd always been doing this and sort of people had already, you know, my friends who, who knew these people, I would get in touch with, they were surprised, but I wasn't surprised anymore.
I didn't expect the response from everyone I emailed, but I expected responses from a percentage of them. Right. And so I was confident that I'd be able to get some great guests, but. I was not, I did underestimate what, you know, what I be capable of and it's not anything personal to me. It's actually, I think it was a result of not appreciating that people would be much more inclined to do it, to do a podcast than they would to answer your individual questions or do a one-on-one phone call because the podcast, you know, a thousand people listen or whatever it is, they could share it with their audience.
I sort of like a nice piece of a nice piece of content, a nice window into how they live and what they think about and questions they want to answer and things like that. So it's just like a much more leveraged form of time. And I think people appreciate that whether consciously or subconsciously a lot more than I expected and I didn't expect it at all.
I just like, wasn't thinking about that completely. So it's like a total multiplier on, on what I could already do in terms of responsiveness and still get a ton of nos and a ton of non-responders. You know, the SS make it much more than worthwhile.
Alex: [00:27:55] Totally. I'm interested. How would you say I'm sure.
Yeah, this is affected it in some capacity. I know it has for me, but how would you say your interests have evolved over time? Just in having conversations with people in writing about stuff? Because something, I think about a lot, I think in general is just the number of like potential outcomes in life as like a function of how much random shit you try out.
And for me, being able to talk with a lot of people has sort of been a way of leveraging that in a way. Like, obviously I'm not going to be able to go off and work in like a longevity research lab and then like turn around and go work on like space factories, and then turn around. And you know what I mean?
But being able to talk with people like that gives me a much better sense of what that actually looks like. Would you say that your interests have sort of changed in a way just based off of that sort of idea?
Jake: [00:29:00] Yeah, I think so. And I think I think there's like certain interests that maybe maybe show themselves like in different ways or like sort of fit for different mediums.
If that makes sense. I'll explain that. Basically when I was writing I was writing mostly sort of on like principles or like philosophies. You know, not like technical philosophy that you would like learn in school, but just like my own sort of thoughts on how to live and like how to make decisions, for example.
And then like here and there, I read about a given thing that interested me, but I certainly wasn't like going deep on longevity or writing a ton about crypto or anything like that. But when it came to talking with people on the podcast and thinking about who I wanted to talk to, those were the types of people.
I want to talk to people who are building the future. Basically I wanted to to sort of like one of my one of my core sort of things that, that I think about is like trying to understand the future and communicate that to others. Like, I dunno why, I dunno if that's a good thing even to do, but that's just like, something that I like to do is I try to figure out where things are.
And be able to like, share that with people. And I think the podcast, it's not necessarily me doing that, but by curating this group of people who I have on and then asking them questions and talking with them and sharing my thoughts here and there, it sort of accomplishes that. And so I've definitely gone a lot deeper in conversation on, on topics like crypto and longevity.
I spend a lot of time usually talking with people about their entrepreneurial stories, which lends itself a bit more towards the types of stuff that I would write about, like, how did you make this decision? How did you make that decision? Some of the questions similar to like what we've discussed thus far today.
So it's sort of like a combination. And I guess one thing I didn't, didn't so much foresee is like because like, if I, if I get a few big names and. It becomes easy for me to get a lot of great guests from the crypto space, but it's hard to, you know, it's still hard for me to get an NBA player.
Like I haven't gotten one yet. You know, I haven't really asked that many, but I've asked a few. And so I think with the nature of a podcast and also your audience, you know, at this point, I know my audience cares about crypto. They care about longevity, maybe not all of them, but like at the very least they care about sort of the future and sort of that like to hear entrepreneurial stories and things like this.
I don't know if they want to hear a basketball player, but I'd love to talk with you know, Carmelo Anthony or whoever it is. And or, or, you know, just random, like whoever, like there's all sorts of categories of interesting people that I would love to talk to, but it gets because it gets easier to get these big name guests in these certain niches that I've already seen.
Fleshed out a little bit. It tends to get narrow and narrow over time, but it's important to me to keep that like generalist mindset sort of like, I think of Joe Rogan as being pretty generalized, even though he's, he's got like a lot of fighters, a lot of comedians, a lot of actors, but it's pretty, he's also got like, you know, he's had Aubrey de gray and the vol he has all sorts of people.
And so, you know, not necessarily talking about his podcasting style, although I think there's a lot to be emulated there as well, but in terms of like his generalist approach, I think that that's really impressive to me. And something that I want to focus on moving forward is continuing to actually broaden the scope of the types of people I talk to rather than just go deeper and deeper.
That's just a personal preference of sort of what I want to do and who I want to talk with. I think
Alex: [00:32:49] that's a great thing to be able to do as well. Like not only. The platform or the show that you have like a good excuse to be talking to these types of people to begin with. It also sort of broadens horizons a little bit, you know, like, I don't know.
Would you say that you've developed any like really strong convictions, just purely based on talking with people that you didn't have before? I, a lot of this is conversation for me is literally just been like, self-reflection like, oh, I've noticed this. Have you noticed this as well? So I'm curious, have you developed anything like that?
Jake: [00:33:19] Well, so one thing I should add to my last thing is that not only getting guests, does it make it easier to get guests of, you know, like interests or in like industries and things like that, but also you develop understanding and, and you learn things about these different spaces. You get more familiar.
And so preparing for conversations with other people in these spaces gets, you know, it's, you, you barely have to do anything in some cases. So it's. Really significantly harder to continue to broaden because you have to, at least for me, like, I like to be really well prepared, just like, just like you seem to be it just makes for a much better conversation.
I think it's a, you know, that's hard if you're going into, if I just have someone who's into nuclear energy on all of a sudden, which I did like gotta figure out what's going on with nuclear energy. So there's a lot of dynamics that, that sort of incentivize getting narrower and narrower, at least staying as however narrow you begin.
So I think going broad is, is challenging, but, but for me worthwhile something that I've learned or gained conviction in from having people on podcasts, I mean, broadly crypto, sure, sure. But something more interesting, I think is. Maybe it's just the people I I've sort of invited on, but I don't do, I like some people I sort of have already followed in the past, but you can only closely follow so many people.
I'm not talking about just like following on Twitter, but actually like listening to their podcasts and reading what they write and things like this. And so for a fair number of the people I found on the show, I do 90% of my consumption of their, you know, public output, whether it's podcasts or writing or whatever, after they agree to come on.
Right. Like I get the idea that there's someone I'd be interested in talking to, then I invite them. And when they say yes, then you delve in, right? Like, yeah, I go to work. It wouldn't be possible for me to invite enough people that I would get enough yeses to do what I'm doing if I didn't do it that way.
And so I do take some risk of inviting someone on who I don't know. That well you know, not at all from personal experience, but you, you can get to know someone in my opinion from most of them on other podcasts and things like that. And so I do run the risk of having sort of people who I could potentially regret having on for, for whatever reason.
There are just people I find like unreasonable, which is something that, to me, like there's not a lot of things that, that bothered me. But when, when people are just like totally unreasonable, it's it's hard for me to have a conversation sometimes. And you can just, you can often just ignore sort of like the sticky subject or whatever it is.
But what I found is that people, no matter how they look on Twitter or basically that or whoever they're, you know, however, they look on Twitter from their own tweets or however, they're sort of reflected to you from society's thoughts on that person or you know, the comment section on their tweets.
or what, you know, random, you know, insert newspaper or media outlet here has to say about them. People tend to be a lot more reasonable than they're made out to be. That's at least something that I've gained conviction in and become convinced of. And certainly there's unreasonable people out there, but I think they are few and far between, and maybe just on on a a couple of certain subjects, but I think there's just a tendency to get these characatures of who people are from what they tweet, even myself, like my tweets.
You can't really, you can know a couple of things about me or whatever, and like get a little bit of a sense of what I'm about and what I do and who I am, but you're much better off reading the blog or listening to me on a podcast or whatever. It's just, you know, and the worst worse than my tweets would be to go and read someone else's tweets about me or.
You know, if, and when there's a media outlet, that's reporting on me, I'm sure that'll be like the worst thing ever. So it's just interesting, like people, I think are, you know, one more reasonable and two just nicer than, than you might expect in a lot of cases. And that's sort of one of the benefits of just meeting a lot of new people through the podcast and having these interesting conversations.
You mentioned
Alex: [00:37:32] the like interview prep sort of process that you went through and being like really well-prepared I don't know if you've had a similar experience, but especially in the beginning for me, like the first, maybe five, like interviews that I did, I literally had word for word exactly what I wanted to say, like laid out.
And I remember having Sort of this moment where I realized that I was using it as as a bit of a crutch. So like, it sounded fine. Obviously it comes with the cost of being a little bit too rigid in the sense that like, if something comes up, it's much harder to sort of take the conversation in that direction.
But I think it's a skill that you have to develop and you're gonna, like, some of them are going to have to be bad, right? Like there's a few that I've put out that I'm like, you know maybe not my greatest work, but you have to, you have to start with that. Right. Or else you're just sort of using that as a crutch for the entire time that you're doing any of these things.
Did you start off like that? Did you start being like way over prepared? Are you still someone who just enjoys, like having every single possible outcome, like mapped out, ready to go? What do you think of?
Jake: [00:38:39] Yeah, it's a good question. In my opinion, probably the most important question when it comes to, you know, the, the art or the skill of, of podcasts.
I hope I'm getting better at it. I don't know for sure. But hopefully practice is helping when I started. I was, you know, not exactly like you, but similar to doing, you know, hours and hours and hours, days and days of prep. Especially for, you know, I started right off with a bang, like my first episode with Aubrey de gray was someone I really admired and, and didn't want to show up unprepared.
And the fourth episode was with metallic. That's insane. I remember like, yeah, I spent, yeah. I dunno like you schedule it for not that far out, so you don't have that much time in absolute terms, but within those two weeks or whatever it was that I had, it was like my day job was getting to, you know, re read stuff from metallic and learning from listening to his podcasts and everything like.
So I spent a ton of time, but for whatever reason, I never I never really scripted it that hard, where it was like exactly in order, perfectly formed questions I didn't spend. I never spent a lot of time writing questions. And I wondered for a while if I was, I sort of foolish because I would spend, like I said, you know, in some cases like 25 plus hours consuming, and then I would spend like one or two on the actual sort of document that I had accumulated of just notes, sort of like getting that into formulated questions or even just coherent bullets.
And so I just ended up with this. Like, I'd spent a lot of time getting to sort of learn things about this person and their perspective and developing interesting areas to discuss with them, but not a lot of time actually thinking just independently from just consuming, consuming. And so I think that's like sort of an important difference as well, because on the one hand you probably could gain sort of like you could probably benefit from spending some time just thinking with like paper which I, I, haven't done so much of consumption.
I've spent a ton of time throughout the life of the podcast. And in terms of like preparing a document with some notes I've definitely trended, although I didn't start off with like a firm script, I've definitely trended towards less and less scripted questions. Just because there's this there's benefits, like you said, of going with the flow of the conversation and asking questions based on curiosity, not an agenda and granted like that, but there's also benefit to the agenda, which is like, like, so Keith or boy was one of them.
Scripted, you know, as sort of a negative word, but like I had a lot that I wanted to discuss with them very specifically. And it was like a really insight rich episode I thought, because I knew where I was going and I actually sort of had the flow preplanned in a way, or at least it into like a few different major categories I wanted to cover, which I had like subtopics and sub-questions within.
So there's benefits to both, but sometimes the less prepared conversation I think is a little bit easier to listen to. Even if it's not quite as dense with like information or insight or whatever it is. So yeah, I think there's a, there's a negative that can come from being too scripted, but I don't think that there's a negative that can come from just spending time getting to know your guests and how they think and what they've talked about in the past.
And, you know, a side benefit is it's always nice. I think as the guests. Like you, you start talking about something and then the host can, you know, shine the mirror back on you or whatever, and reflect back at you and say like, bring up another point that you had made in the past that's related. And then you can all of a sudden go deeper on this point that they had only touched on, on another podcast or only touched on in a blog post that they'd read or whatever it is.
So a big fan of preparation, but also certainly appreciate the the benefit of spontaneity.
Alex: [00:42:47] Definitely. So I've got one more for you. Just a little bit more broadly, you know, just in the sense that you don't seem to have that much of an issue making these big leaps, be it career wise, just larger decisions in life or anything else.
What's what do you see as being the next big move for you? Or what do you see yourself doing, you know, some years out? Are you someone that like plans that or is it something that you just sort of take away.
Jake: [00:43:14] Yeah, I'm certainly a believer in risk taking. I read your recent blog on that. And I agreed with it pretty wholeheartedly.
And also actually you mentioned before sort of believing in and accumulating a diversity of experiences, which, which I agree with as well. And they sort of, I think they're related in a way you sort of have to take risks to do different things, frequently start different things. You know, to start something, you usually have to add something and there's usually like risk involved in both pieces of that, for sure.
So but in terms of me like goals for the future, I don't plan that far out. And if I really have I might have sort of loosely formed ideas of what the future might hold for me. And, you know, part of it's like sort of being entrepreneurial and, you know, I want to be. Very successful by my own definition, which is continuously evolving.
And not, not easy to define, even for me now I know like a bunch of things that contribute to it, but it's not like I'm working towards this very specific thing. It's more so just moving in a certain direction, trying to make the most of life. And just making turns as I see fit and changes in direction as I see fit right now, you know, I'm a year almost to the day of having started the podcast.
And I plan to continue to do it for hopefully a long time and maybe I'll take breaks. Like I don't want to just do it for the sake of doing it. I want to do it so long as I'm still excited about it. And but, but I do see it being like something similar to like my blog. I haven't actually written in a while, but it's up there and like, I'll continue to write.
I, I, I imagine like, I'll come back to it for periods of time. Then go away from it again. So the podcast of you similarly but right now I just started working on this project called 1729. It's at 1720 nine.com. People can go check it out and I'm just like going all in on that. I think it's a a very exciting venture that, that I'm just, you know, I'm not afraid to just sort of throw myself into something.
And that's where my attention is right now with the podcast, just sort of being an interesting side side hobby that I like to do, and it doesn't take too much work. So, and I get to meet really interesting people and talk to really interesting people. So I can't tell you too much about five years from now, but at least for the near term, 1729 in the podcast, I think is as far as work goes, that's, that's where my folks still be.
Alex: [00:45:40] All in, man. That's awesome. I appreciate it. Thanks so much for the time.
It means a lot, really.
Jake: [00:45:44] Yeah, of course. Have a good rest of the day.
Alex: [00:45:46] You too, man.