The Almanack of Naval Ravikant by Eric Jorgenson | with guest Caitlin Rozario

0:01Caitlin Rozario:Welcome to Business Book Club, the show where top entrepreneurs break down the most powerful insights from the world's best business books. I'm your host Sam Brown, and today we're diving into The Almanac of Naval Ravikant by Eric Jorgensen. They say money is the transfer of wealth, but wisdom is the transfer of experience. Today's book is arguably the highest density collection of business wisdom released in the last decade. Naval, the famed Silicon Valley founder and investor, is famous for saying that you should escape competition through authenticity. But what does that actually look like in practice?

0:39Caitlin Rozario:To help me deconstruct this, I'm joined by Caitlin Rosario, the founder of Interlude. I wanted Caitlin for this specific book because she lived one of Naval's core lessons in real time. She realized her productivity app felt like work, while teaching it felt like play. So she shut down the software side of the business and pivoted to work in her zone of genius. We'll get into that in just a minute. In this episode, we discuss how to find your specific knowledge, why you should keep a smile file to hack your brain's negativity bias, and why being a rat in a race isn't the insult that you think it is.

1:16Caitlin Rozario:So let's get into it. Caitlin, I asked you, what was the most impactful book on your life? And you chose The Almanac of Naval Ravikant. why? Thanks for having me, Sam. As you know, it was very difficult for me to pick one book, but this really was at the top of the pile for me. And I think as entrepreneurs, we are really busy and we've got a lot on, but this necessarily being a collection of tweets and interviews and meditations on those things, it's really easy to read. It's super actionable. I got through this in no time at all. So while I'm really glad that we're going to get to distill things here, it's also something that I think people can just pick up and as you said, flick to something and get something from it.

1:53Building specific knowledge will feel like play to you, but will look like work to others. Okay, that's great. So why does Naval say that building specific knowledge is important? So I think we need to go back to what is specific knowledge. Because I remember the first time I read this, well before I got the book, I was like, okay, I think I know what you mean, but what is it? So I went and did some background reading. And remember, a lot of this book is tweets, so context you have to kind of dig for sometimes. So to read the full quote, it says specific knowledge is found much more by pursuing your innate talents, your genuine curiosity and your passion.

2:27It's not about going to school for whatever is the hottest. It's not by going into whatever field investors say is the hottest. And actually he goes on to talk about how it's not even necessarily academic or business focused. He uses gamers as an example. And he was like, gamers have this really specific knowledge of world building and even things like coordination and stuff like that, that people who don't do that don't know how to do. So he uses that as an example of deep, specific knowledge that is built up by just going really into something. So it's about being really immersed in something and being really detailed about it.

3:07Naval's always talking about having these mental models available to you. And this seems like a mental model that would help you decide on what you should be working on. Because the second part of this is that it'll feel like play to you while it feels like work to others. So yeah, how do you think the sort of play aspect comes into this? Yeah. So I think obviously there's always going to be work that feels like work to you in general. But I think the point of this is about optimising for the things that do feel like play to you. And so this really, really clicked for me when, like you said at the beginning, we pivoted interlude from an app to workshops because me and my partner, we were upskilling the whole time.

3:48And I'm so glad that we did it, but like that was really, really tough, really tough. But while we were doing it, we were doing these workshops as part of our onboarding process because we wanted to have a really strong kind of psychologically led onboarding process. And these workshops are doing really, really well. And I kind of was thinking about it and I was like, okay, I love doing the learning and research for them. I love designing them and I love presenting them. And we decided to shut down the app on a Wednesday. And that was the end of it. And then on the Thursday, I was like, hang on a minute, maybe we could be doing these workshops as a full-time thing.

4:24And this had already been in my head. I'd read this a little while before. And I remember so clearly, I've got a notebook upstairs where I've got this drawn out. And then I was thinking about the Japanese concept of ikigai, which I'd heard of before, but I hadn't really internalized it, which is the cross section of something that you love, something that is good for the world, something that you can get paid for, and something that you're good at. I was like, this is it. Okay, this is it. For me, the specific knowledge, I was like, if we break that down into learning, curating, and presenting, most people think learning is really dull.

5:01A lot of people don't read because I think it's boring. The curation bit, I think, can only come if you're learning. If you're not learning, then what can you curate for people? And then famously, public speaking is one of the biggest fears globally, but I love it. I thrive off it. I remember so clearly that day and getting my notebook out and the idea of ikigai and this idea of specific knowledge and play coming together. And I was like, here it is. This is what it is. So this was like a really genuinely very impactful idea for me. Yeah, that's super cool that you were able to sort realize that as you were kind of closing the app.

5:35My partner teases me about reading business books for fun. We went to a spa retreat last year and I read Smart Brevity, a book on copywriting and influence, the psychology of persuasion, while I was just sort of sat around a pool. And I would do this anyway. I think Novartis says this in the book, if he'd got no sort of financial reward from doing this, he would be building businesses and thinking about how to invest and that sort of for 16 hours a day, seven days a week anyway. It just does it for fun. So really leaning into that is the way I suppose that you should decide on where to spend your time and what you should kind of lean into.

6:10Yeah. And I think as entrepreneurs, we have that privilege, you know, where other people don't. And I think if I said this in a general audience, people would be like, but my boss tells me what to do, which is true. And I do believe that we have some autonomy there anyway. It's kind of the whole founding principle of interlude is having a of autonomy over your work. But as entrepreneurs, we actually are building our futures, we're designing our futures. And I was very lucky that I was able to learn that lesson, that the app felt like work and the workshops feel like play. And I was able to make that transition.

6:42So I think that if anyone is in that situation where you're running a business that feels only like work and feels really difficult and like you're trudging through mud, how could you tweak some parts of it to really build on the bits that feel like play. And just for your sanity and your mental health and your physical wellbeing, it can make such a massive difference. It did for me anyway. Yeah. So true. Another massive bit of wisdom that Naval talks about in the book is we don't really put much effort into thinking about things like where we're going to work, what sort of job we're going to do.

7:12Did you do anything yourself to figure out what feels like play to you or did that kind of come naturally and it was like a realisation? Yeah, a bit of both. So the workshops were a necessity. We did a lot of research. There's a fantastic website called growth design, growth.design. And it's about the psychology behind product building and things like that. We learned a lot from that about onboarding. So the workshops were a bit of a necessity where my partner was like, you're good at talking. Can you do this? And I was like, okay, cool. And we kept getting really good feedback on them. And then because I was doing them as part of like online onboarding, I started getting some opportunities to do them in person.

7:53And then I kept getting this good feedback. And I was like, hang on, maybe I'm good at this. And I always think about how I used to get told off for talking too much in school. And now I'm like, people pay me for it. So it's, it kind of, I didn't go out to start doing it, but I did always think that I'd want to get paid for public speaking, but it wasn't really on my radar. But then once I started realizing and getting that positive feedback, that really helped. And I'd say another tip in that sense from my coach actually, is when you get that positive feedback, screenshot it and save it to an album, whether it's about you, your product, your ideas, whatever it is, whether it's LinkedIn comments, customer feedback, reviews, save them all in one place so that you can go back and you have a bit of a thread going through of what that thing looks like.

8:39And then you can start to see visually what they're all saying. And that can give you a bit of an indicator. That's awesome. I've never heard that before. I'm definitely going to start doing that because it's so easy to forget the positive feedback that you get and so easy to remember all of the negatives. So that's an awesome tip. That's how we're wired. Our brains are wired for that. So, you know, we have to override the negativity bias that keeps us safe. Mine's called love. Some people call it a smile file, things like that. And it's just, yeah, it's really helpful when you're feeling low to be able to just be like, okay, my default when I feel like that is to go and look at that and build myself up a little bit.

9:15Nice. That's way more healthy than just scrolling social media. Escape competition through authenticity. So why do you want or need to escape competition? So this one is really important. When I started out in the startup world in 2020, I've always thought of myself as a kind of learning by learning person. Like I love studying. I've got a few degrees, things like that. In fact, I did an MBA because I was like, oh, well, I'm starting a business. I should probably do an MBA. I love doing it, but I wouldn't say it's the route that you have to take. But the kind of spiral that I got into was that I started to, I felt like I didn't know anything.

9:57And there are so many people in the startup world telling you, because they're building their personal brands or they're promoting their product, what they did, how they did it. And at first that was really helpful. But actually what I found is after a while, I started to doubt my own convictions and my own decisions and my own opinions, because there was always someone who had raised more money, who had a more developed product, who had more customers, who was saying something else. And I think ultimately that did cause our business to suffer. But I think actually more than anything it caused me to suffer because I really lost a huge amount of confidence through that.

10:31And so again, when we had this pivot, one of the big things I've been working on is doing it my own way and being like, okay, yes, it's really helpful to see what other people are doing, but I've built up a bit of a better filter and a barrier where I'm able to appreciate things and be like, that's cool. That's interesting, but not necessarily suck everything in because all advice sounds like good advice when you don't know what to do. So another thing that he said that I've written down as relating to this is like, every human is different. Don't copy. And it's easy to say that. But then the next thing that he says, I think really explains it, which is, and it's really relevant to what I'm doing.

11:09And I think what a lot of founders are doing, which is if you are fundamentally building and marketing something that's an extension of what you are, no one can compete with you on that. And I think for me, interlude from the beginning has been based on my own experiences. It is to this day, I'm not saying that I know how to make work perfect and to make productivity completely un-toxic. I'm learning that while I'm going through, and it's a co-creation building process. I'm the one doing it. I'm the one delivering it. So why would I do that in the same way that other people are doing it? Because that's their thing.

11:44And that comes back to that authenticity point. Because if you're building something that is you, essentially, it has to be you all the way through. Otherwise, people feel it. They might not know why, but they feel that they know that it's incongruous in some way. Yeah. And I suppose that what it also does is it puts a barrier up or like a moat around what you're doing as well. Nobody else is going to make interlude the same way as you can because they don't have your experiences and your expertise through life. One thing that you said here, which I loved, all advice sounds like good advice when you don't know what to do.

12:19And that's so true. It just reminds me of another quote that Val said in the book, which is he knows a lot of well-read people that he doesn't think are very smart because they read the wrong books or they started off with the wrong foundation of books. And then everything else that they read after that was kind of filtered through the first books that they read. So their worldview was based on the first few sort of foundational books. and if you don't know which advice to take, it all sounds like good advice and you don't have the knowledge and the filter to understand which is the good advice and which isn't.

12:49I actually heard that advice right at the beginning from my friend James Timmons, who owns some brunch restaurants called Utter Waffle. He was the chef on our app back in the day. He said right at the beginning, don't listen to everyone's opinions because they are taken out of context and you need to get good at picking which ones. And that's probably the best advice I ever heard, but I didn't understand how to do it. And we spoke at the beginning about building mental models. And I think looking back, that's the mental model I wish I'd built. And the one that I'm working on now, which is taking something, looking at my specific experience and being like, which bits can I take from this?

13:25And actually, I think this is really relevant to this book in particular, which is that part of the reason why I like it is that I think that it's written in a way where he's kind of like, this is what I think, you can take it or leave it. Like, it's weirdly like really confident. And like, this is how things are. But also very much like, I don't really care if you disagree or there's that's the confidence I think is like, here's what I think here it is. But I think that that is then paired with, I'm talking about myself in the past now. And I think I see this very clearly, especially on social media.

13:59I think we've got a bit of a reluctance to pass things out these days, I think because we're so used to short form media now, we're all looking for a quick thing, a quick fix. I know myself, I was always looking for a course to tell me what to do. Instead of being like, okay, I have to just dig into this and figure it out. I was always looking for someone to have laid out the five steps for me to figure the thing out. Those things can be helpful, but I think they should be supplemented by rigorously interrogating things over and over. and that's a muscle, right? If you say every time a piece of information comes your way and you're like, okay, that's interesting, relevant to me, yes, no.

14:36Or is it something you want to be like, okay, I'm going to act on that. I just took everything as I'm going to act on that, which is exhausting. So I think that we need to get much better at doing that, making that decision-making muscle, but also being like, everyone is just writing from their own context. And I think there's a lot of things in this book that people could be up in arms about, but I decided when I was reading it to not do that and to be like, that's your opinion and your experience, I'm going to take what I want from it. There's particularly a bit where he says, I would argue with my girlfriends and even today with my wife, I don't do that.

15:08That's not a problem I solve. I still argue with my mother when she hands me little to-dos. I just don't do that. I'd rather hire you an assistant. And I wrote in my notes, I was with him up to this bit, but how much wealth is worth being an arsehole? But at the end of the day, if that's where he's at and his family like we don't know his family could be there oh silly naval you know like

15:30Caitlin Rozario:okay yeah i think a lot of people i hope he doesn't do it in an asshole way yeah right kind of guy exactly but he writes in a he writes in such a very matter of fact yeah so but i think a lot of people and my first thing was to be like outraged for the women in his life but actually like we don't know what his home life is like we don't know what that context is and so i think that this book was actually really helpful, not just the learnings, but practically it was really helpful for me to get into that take it, leave it, take it, leave it kind of mental model. Yeah, 100%. You can read all the books you like, but if you don't put any of it into practice, you'll never learn how it relates into your life.

16:08On the subject of impact, what impact does leaning into your own authenticity have? What's been the result of that? I realized that I am the competitive advantage in my business. And when I was thinking about these lessons, I was trying to think about how they relate to each other as well. So I've decided that the best thing for me to do for my business is to really double down on the things that feel like play to me, but feel like work to others, and doing that in an authentic way and not copying other people. Because other people could have exactly the same things that feel like play, but they're going to do it in a very different way to me.

16:43So it's really helped me to think, okay, what is it that I do differently and better than everyone else? And one of the things that I've really doubled down on with this is a lot of people are out there calling themselves experts. And I don't think that that term should be used so lightly. And I've even been on a few podcasts and talks and things where people are like productivity expert. And I'm like, I'm not, I am absolutely not a productivity expert. What I think I am is a very, very good curator. I think that I'm really good at being like, I can take in a huge amount of information. I have really, I'm a quick learner.

17:18I have really good retention. I've always been good at this for other people. Worse for myself, as we've been talking about, but I'm really good at being like, oh, this is really helpful. Here's this thing. Or putting things together that other people may not have come across because I've got such a broad range of interests. And I used to think, oh God, I need to be a productivity expert. But now I actually think that my breadth of interest and knowledge and learning is what makes what I do singular. So I'm really leaning into that now. Why acceptance is vital to success. I love that. And what does Naval say about this?

17:50I know he's somewhat of a philosopher nowadays as well. His book sort of touched on aspects of happiness and relationships and a lot of different things in life. So how does acceptance relate to success? I wanted to bring two quotes together for this because I think that it creates a really interesting dialogue between them. The first quote is, I'm not going to be the most successful person in the world and nor do I want to be. The second one is, I think just being aware you're a rat in a race is about as far as most of us are going to get. I remember I was on a plane and I read that and I was like, but I'm special.

18:28But then I was like, actually, I've never had aspirations to be out of the rat race. It was kind of a cathartic thing to read. I was like, I've never wanted to be the person who sells all my worldly goods and goes and lives in a mountain. I like working. I like living in the city. I like being part of this ecosystem. And so at first that was really like to me, but actually I was like, no, I am a rat in a race. And he says the best case is that I'm a rat who might be able to look up at the clouds once in a while. And I was like, that should be okay. Yeah. That really struck a chord with me as well.

19:03Just stopping to appreciate it. Just every once in a while, just realizing what you're doing is, yeah, it's great. Yeah, for sure. And I think that he talks as well in this part about death and he talks about it in a really almost joyful way where he's like, we're all going to die. So you may as well take some ownership and figure out what you want to do. And there's a bit where he says that's really deep. And he says, what if this life is the paradise we were promised and we're just squandering it? Again, I'm just sat on this Ryanair plane like, okay, right. And it really made me think about, I had a chat with a lovely entrepreneur called Danny Matthews, who's a brand expert.

19:47He is actually an expert and also has a cafe in the Cotswolds, which is really cool. And he was talking about figuring out what success meant and how he was given a huge contract, had some unbelievable health problems just due to burnout and stress, and that him and his wife sat down and they mapped out what their perfect life looked like. And then they realized that it was minuscule compared to what that contract was. And he was like, why am I literally, quite literally killing myself for something I do not even want? And that resonated so much with me because I felt the same when we were building the app.

20:24I was so unwell. For three years, I was very unwell, mentally, physically, emotionally in a very bad place. I was like, why am I doing this? Naval actually quotes Homer in the Eliad, which says, everything is more beautiful because we're doomed. You'll never be lovelier than you are now and we'll never be here again. And all of this kind of existential stuff really did come together to be like, what do I want? What do I actually want to achieve? And what do I need to accept? And those two things together, I think, when you bring those together and you see where you are on that, and obviously it's going to go up and down, there's going to be wiggle room, but where you see where you are in that, it's really liberating.

21:06You could take it in a kind of nihilistic, morbid way, but I found it a very liberating idea. Yeah. You have to be in the right headspace to kind of go down that route, I think. But going into it from the perspective of, I'm only here once and that's why it's important. It's definitely something that's going to add to your joy or happiness, or as Navar likes to say, your peace that you have in life. I've heard so many people talking about like the most successful people they know are just on this treadmill they've conditioned themselves to be working 20 hours a day seven days a week sort of hard businessmen who won't let up at all and it's not like a fun place to be but they're not any more happy than someone who's actually taken a second and thought about it I think that's so interesting because I certainly found that I was working to a definition of success that was put forward rather than what I thought success looked like for me.

22:02And I wish I'd thought about that sooner. And I would really, really recommend everyone listening to this, if you haven't, sit down and map out what success looks like financially, for your company, for yourself. Cal Newport, one of my other favorite thinkers, he calls this lifestyle-centered career planning. So what's the life you want and how do you have to work to get that life? And what I think is so interesting about what you said is people say the most objectively successful people and then all these terrible things, are they successful then? Because we measure success just in, this isn't a new idea, but I think we haven't internalized it, therefore we have to keep repeating it.

22:38Just because it's success, it's financial, it's the big company, it's the big valuation, it's the big salary, it's the headcount, all of those things. But if you're miserable, can we possibly call that success? I don't think so. And when we were looking at this a few weeks ago and we started thinking about it, one of the quotes that I found that he said is, the hardest thing is not doing what you want, it's knowing what you want. I think that is one of the truest things in the book. And we saw this at the Paris Olympics with Adam Peaty, right? Already got a gold. The gold was amazing, but then it was very well documented how miserable and unhappy he was.

23:17And I actually remember listening to him on the High Performance podcast and I was like, this man is whoa like he sounded the flat affect you know he was being really open about his struggles but he did not sound like he was over them you know and then we saw him win that silver and i think that the interview i heard was kind of commiserating with him and kind of being like he did so well anyway and he was trying he was at pains to say no this is the biggest success of my career because it was a silver and i've got the medal but my kid is here i'm happy i'm healthy and I think that we're all striving for the gold.

23:52And sometimes if we've interrogated it and we're like, the gold is what I want, then fine. But I'm quite happy actually with bronze, if it means that I'm healthy and I'm happy and my relationship is in a good place. So that I think is, it sounds so existential, but I wish I thought about it sooner. And I wish I paid more attention to it because I would have saved myself a lot of actual physical pain and mental anguish if I thought about it sooner. Yeah. Were there specific steps that you took to go down that route? I know you talk about the planning. Was there a framework that you used? How did you do that?