The Rich Roll Podcast - The 5 Types of Wealth: Sahil Bloom On Why Time, Friends, Mind & Body Always Come Before Money

Episode Date: January 27, 2025

Sahil Bloom is a Stanford athlete turned finance executive whose life took an unexpected turn when a friend's observation catalyzed a complete reevaluation of success. This conversation explores his ...perspective on wealth, which transcends traditional metrics to embrace a more expansive definition of abundance. We discuss his framework of the Five Types of Wealth, the power of tiny actions to reshape destiny, and how to deploy your attention toward what truly matters. He shares profound insights on nourishing relationships, differentiating between urgent and essential, and finding purpose through service. Sahil is wise beyond his years. Enjoy! Note: In celebration of Sahil's appearance on the podcast, we're giving away three signed copies of his transformative book. Subscribe to the newsletter at richroll.com/subscribe for a chance to win. Show notes + MORE Watch on YouTube Newsletter Sign-Up Today’s Sponsors:  Momentous: 20% OFF all of my favorite products  👉livemomentous.com/richroll On: High-performance shoes & apparel crafted for comfort and style 👉on.com/richroll Roka: Unlock 20% OFF your order with code RICHROLL  👉ROKA.com/RICHROLL Calm: Get get 40% off a Calm Premium subscription 👉 calm.com/richroll Check out all of the amazing discounts from our Sponsors 👉 richroll.com/sponsors Find out more about Voicing Change Media at voicingchange.media and follow us @voicingchange

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Starting point is 00:02:19 Is this the moment I'm supposed to feel happy? If I continued living the way I was living, I was gonna wake up in 50 years and wonder what the fuck just happened. Sahil Bloom is redefining what it means to be truly wealthy. A former Stanford baseball player turned private equity executive, Sahil faced basically a crisis of conscience when he realized that what he was pursuing was actually at odds with what mattered most in his life. Everything looked like it was going well on the outside, and on the inside everything
Starting point is 00:02:52 was slowly but steadily falling apart. So he walked away from his lucrative career and basically invented a new one, a path that better aligned with his values and prioritizes personal growth. Insights he now shares with the millions of people across the world that subscribe to his newsletter and follow him on social media. And along the way, Sahil defined a new and more expansive way to think about wealth.
Starting point is 00:03:18 One that goes beyond finances to consider relationships, time, and wellbeing. All of which he explores in his new book, The Five Types of Wealth. We're living in this world where you are having to run faster and faster just to stay in the same place. You spend your time on things that actually aren't progressing you in the direction of your goals,
Starting point is 00:03:39 in the direction of the things that are going to move the needle. Later is just another word for never. You are always in control of taking a few tiny actions that will lead you to be slightly better off tomorrow. Your wealthy life will involve money, but in the end, it is going to be defined by everything else. Thanks for coming out here, man. Thanks for having me.
Starting point is 00:04:04 It's a thrill to be on the other side of this. Well, thrilled to have you here. Can't wait to talk to you about the book. I was just mentioning a few moments ago, you did a fantastic job. It's quite an accomplishment and you should be very proud. I'm excited for the world to enjoy what you've created. That means a lot to me.
Starting point is 00:04:23 Yeah, plenty of ideas to explore in that, but I wanna understand your personal story a little bit better. There's certain facets of your backstory that are very similar to mine and many that are very different. But essentially, I wanna start at the beginning, but the sort of thumbnail or cliff notes
Starting point is 00:04:41 of the whole thing is you were an NC2A baseball player, went into finance, became this private equity guy, and around the time of the pandemic, had a little bit of a sort of reawakening of self and did this pivot, this life pivot, this career shift away from what you were doing into a more public facing sort of service oriented occupation of your own creation
Starting point is 00:05:10 in which you started sharing wisdom and helpful advice that quickly escalated and put you in a position to be this sort of influential authority on a variety of topics around wellbeing that led to this book and you sitting across from me today. Yeah, I mean, it's been a crazy journey. The last few years in particular, but I feel like all of it started a long, long time ago.
Starting point is 00:05:40 And for me in particular, I feel like the common thread through my entire life has been this seed of this idea around the rejection of common convention and rejecting these kinds of cultural defaults that we so often just find ourselves accepting and embracing in our own lives. And I reflected a lot on that
Starting point is 00:06:00 in the context of the writing process here and more just in the context of my own sort of inner work, that I think that part of my DNA, if you will, really came from my parents. And this experience that I think they had in choosing their relationship over the cultural conventions that would have said not to do that and how that has kind of led to this entire lineage
Starting point is 00:06:26 and this trickle down effect through my own life, through my sister's life and through the family and the creation of all of that that's followed. Well, explain that a little bit more because the story around like your mother and your father's relationship is pretty extraordinary. Her coming from India and how they met and the kind of high stakes that were involved in them being together. Yeah, so my mom, as you know, her coming from India and how they met and the kind of high stakes that were involved
Starting point is 00:06:46 in them being together. Yeah, so my mom, as you said, my mom was born in Bangalore, India, born and raised. She in, let's see, 1978 applied in secret to come to college in the United States. She was the youngest daughter and really everything about her life had sort of been planned out for her.
Starting point is 00:07:06 She was gonna have an arranged marriage in India to a man and live the life that followed. And for whatever reason, she rebelled against that, decided to apply to school, got a scholarship to come to Mount Holyoke in South Hadley, Massachusetts. And it seems like my father kind of lived this like very similar parallel track in his own life.
Starting point is 00:07:26 His whole life had been planned out for him. He was from a Jewish family in the Bronx, New York, on the other side of the world. And his whole life had been planned out for him by a rather domineering father. He was gonna go into academia, get a nice stable job, marry a nice Jewish girl and live his whole life. And for whatever reason,
Starting point is 00:07:44 my parents had their paths cross in a rather unlikely twist of fate. They crossed paths for only two weeks at Princeton University. My dad was finishing his dissertation there for his PhD. My mother was working in the library to pair away through a master's program she was just starting. And my mom was the bold one, went up to him and asked him if he wanted to go out and get ice cream.
Starting point is 00:08:07 And about an hour later, they were on their date. And it's so funny hearing my mom tell the story because my father said to her, my family, my father will never accept us. And my mom was so blinded by his use of the word us that she completely missed the message, the underlying message of what he had said. And unfortunately, my dad was right.
Starting point is 00:08:26 And his father was not accepting of this courtship and told my father that he had to choose between my mom or his family. And he made what I imagine was the most challenging decision of his life, which was to leave his family and choose love, choose my mom. And to this day, I have never met, I never met either of my father's parents.
Starting point is 00:08:54 His father passed away many years ago. His mother is still alive. I've never met her. My dad has four siblings. I've only met one of them. I first cousins out there that I've never met. Just this one decision. It's pretty hardcore.
Starting point is 00:09:09 I mean, it's one thing to issue an ultimatum like that, but then to follow through on it for decade after decade. Cause those things tend to sort of come around with time. Right? And the fact that it never did, and you never met your grandparents on your father's side. Yeah, time, it's a funny thing, right? Like I have the perspective that time doesn't heal anything
Starting point is 00:09:33 when it comes to relationships. I think in a lot of other areas of life, time has an ability to heal, physical trauma, time has ability to heal. But with relationships, I have found that those hard conversations avoided are like a debt. And when you take on that debt, you're going to have to repay it with interest
Starting point is 00:09:54 at some point in the future. And the problem is when that interest builds so much over so many years, it just becomes overwhelmed. With no installment payments, right? Yeah, that is interesting. That's an interesting idea. Yeah, you think that, well, I think it also depends what stage of life you're in when the disagreement occurs.
Starting point is 00:10:12 Like if it happens earlier in life, it sort of becomes this entrenched neural pathway. But there is this idea that with time, it'll just kind of fade into the background. And you're right, like that's actually not the case. There's that saying that sometimes there's just too much water under the bridge. And I think with something as big as this,
Starting point is 00:10:34 you know, the other thing I'm just aware of is there's two sides to every single story. And obviously I accept and embrace my father's side of the story and the decision that he had to make and how challenging that was. But I'm sure the story that the rest of his family was told was a different one. I can't imagine that his father told the story
Starting point is 00:10:55 the exact same way that my father did. And at the end of the day for me, people often ask me like, oh, have you ever wanted to go and meet your grandmother, meet your father's mother? To me, that would have to come from my dad. It would have to be that he wanted to go do that or that my mom wanted to go do that.
Starting point is 00:11:10 Because my mom has experienced a lot of grief associated with being the reason that my father had that challenging decision to make and that breakup from the family. I have always taken the position that my mom is like the best person in the world to me. And anyone that wasn't okay with her is not okay in my book. I have never been the one to kind of push the issue.
Starting point is 00:11:33 But if my father or if my mother came and said that they wanted to go see my grandmother, I'm sure I would go do that. And her gambit of course, was that she was so far away from home. And the fear with her family was that she would find an American to marry and never return to India, which is exactly what happened.
Starting point is 00:11:50 So there was risk on both sides of this equation. Yeah, and when my mom introduced my dad to her parents, they were not okay with it. The idea of her going and marrying an American man was not according to their plan. They got over it though. They got over it when they saw that my father had left his family for their daughter.
Starting point is 00:12:09 And I mean, what greater sign of love and of that feeling of connection can you exhibit than that? And ultimately my grandfather and my grandmother on my mom's side ended up taking my dad in as a son, basically in the family. And so that feeling of connection to that Indian side, to the Indian culture grew much, much stronger as a result of this.
Starting point is 00:12:31 And for my father, I mean, the feelings of connection that he had with my mom's parents were enormous. Well, your relationship with your parents is kind of an extraordinary thing. And probably, you're somewhat of an outlier in that regard, like the reverence and regard and respect that you have for both of them and the manner in which you demonstrate that through many of your bigger life decisions
Starting point is 00:12:53 is like aspirational. And I think that to your point around social convention, like I kind of wanna return to this idea because this is sort of a, kind of a core theme in the book and all the work that you do. Yes, like their relationship represents a transgression of social conventions. But then again, within that,
Starting point is 00:13:18 there were a lot of social conventions that were adhered to and reinforced in your life, right? On some level, your mom is a very traditional like Indian mother that comes with all of the kind of expectations around academic excellence and what kind of profession you're gonna pursue. And your dad is a professor at Harvard, right? Like, so there's a traditional, you know
Starting point is 00:13:38 kind of sensibility around all of this. So I'm curious around like your relationship with social convention and what led to you trying to, kind of find ways or why did you feel compelled to break these because it seems to me that you were raised very much within the constraints of these social conventions, which were incentivized and reinforced.
Starting point is 00:14:01 Yeah, I think that's a great point. And I think in both of those cultures, like my mother on the Indian side and then my dad coming from an academic background, academic performance and achievement was very much the standard in our household. And I don't know if that was as much about a cultural convention as it
Starting point is 00:14:19 was about a standard of excellence that my parents held us to. My parents were big believers that there were sort of two key pillars to a strong relationship. One is high expectations, and the other one is high support. And both my parents believed that,
Starting point is 00:14:35 that they had high expectations for us all the time. They thought that we should achieve at an extremely high level, but they were also willing to raise us up on their shoulders with the support to go and meet those expectations.
Starting point is 00:14:47 And if you just think about that, high expectations in the absence of high support is a big issue. That's a recipe for resentment. When someone expects a whole lot from you, but they're not willing to actually support you to go reach that. My parents always managed that and provided both.
Starting point is 00:15:01 I always felt like, yes, they had high standards, but also, yes, they were willing to help lift me to those standards. The unfortunate thing and how it manifest in my own life was from a young age, I have an older sister who's three and a half years older than me. And she was very, very academically oriented and high achieving.
Starting point is 00:15:24 And what would happen over and over again was my sister would go through a school and have the best grades, do everything that my parents could possibly want from her. I would get to class the first day and the teacher would say, oh, you're Sonali's brother and have this like bright look in their eyes,
Starting point is 00:15:39 in for another star student. And within a week or two, they would inevitably be disappointed because I was kind of a, you know, I was a jerk off. Like I was a kid trying to find himself. I was more into sports and running around and not as academically oriented. And unfortunately what ended up happening was
Starting point is 00:15:57 I started telling myself this story that I was not the smart one. And my sister was the smart one and I was the athletic one or I was something else. And when you tell yourself that story, what I have found in my own life is that like these original stories self-perpetuate. It's very easy to find evidence to confirm that story.
Starting point is 00:16:17 It's very hard to do anything that conflicts with that story that you tell yourself. So at every stage of those early years of my life, I was just reinforcing this belief that I wasn't the smart one, that I was not as capable as my sister, that I was not capable of achieving on the level that would make my parents proud.
Starting point is 00:16:35 And that internally bred a lot of insecurity in who I was and in what I was doing. And my parents at every turn tried to break that. They constantly told me how much I was capable of, that I was smarter than my sister, that I was capable of so much more than what I was doing. But when you tell yourself that story, it's very hard to hear the opposite.
Starting point is 00:16:57 You need to learn it for yourself. You need to do the inner work in order to kind of break those early patterns. So you're creating this own internal sense of insecurity. That's like, let's just call it not evidence-based, right? Cause you're basically, you know, moving up the chain, you know, doing all the things, right? So you obviously did well enough in high school.
Starting point is 00:17:20 You got into Stanford and you were an athlete who was successful enough to be able to play at Stanford, which is a top level baseball team. I don't know if they still are, but I know they were when you were there and they were when I was there. So it's hard for the average person to think like, why would this guy be insecure?
Starting point is 00:17:38 Like look at his stature in life as a young person at a place where anything is possible and everything is available. Yeah, it's hard to justify and rationalize insecurity. We had a conversation about this earlier. You look around at some of the most successful people in the world and look at their actions, the things they're doing on a daily basis,
Starting point is 00:17:57 the way they're interacting with the world. You see insecurity all around you. It is almost completely dislocated from the actual results that the person is creating. And oftentimes for some of the most high achievers, insecurity is the thing that actually allows them to go and do these extraordinary things.
Starting point is 00:18:14 The unfortunate thing is that it is not conducive to a life of fulfillment or happiness. You're constantly searching for that external thing that will fix how you feel internally. And so even, I mean, in high school, you mentioned that I did well enough to get into college. I did not do very well academically. I just so happened that I worked hard enough
Starting point is 00:18:33 at being able to throw a baseball hard enough that I kind of found the side door into getting into Stanford. While I was there, I also really just like continued to consider myself an athlete. I was not studying, I wasn't going to classes. I wouldn't take the hard class because I was scared that it would expose me as not smart.
Starting point is 00:18:52 And again, back to that idea of those stories, those stories you tell yourself, hold you back because you don't give a hundred percent because you're afraid of what will happen if you do and still fail. You're afraid of that idea, like that idea about who you are getting broken, that internal ego.
Starting point is 00:19:10 And when you're pursuing your entire life on the basis of these insecurities, you're not making rational decisions. You're not making the decisions that are right for you. You're making the ones that you think are going to make you feel good. The stories we tell ourselves about who we are and what we're capable of hold, you know,
Starting point is 00:19:28 so much power in terms of driving results in the real world. And the truth of the matter is those stories are not true, whether they're positive or negative, usually they're negative. They're not really that rooted in reality by and large. So I thought a lot about this and I'm trying to sort of crack the code on the process of untangling those stories
Starting point is 00:19:52 and figuring out how to tell a new story that will take up residence in the way those old stories seem to persist. And I think it's very difficult to do. And I think it begins with acknowledging that all of that stuff that you're cycling in your mind is indeed just a story and doesn't have to be the story that you continue to tell,
Starting point is 00:20:15 but it's very difficult to like override that kind of default network. I think the common themes that you see in people that have managed to do it is a massive sharp acute traumatic event. And that versus years and years of therapy and inner work. And I think over and over again, I have seen that that traumatic acute event,
Starting point is 00:20:40 it's the rock bottom moment for the addict, right? Like you have the rock bottom moment and that ends up propelling you to change. And that in people that I have seen that have been able to kind of make those changes, change those narratives has been the most important thing in hindsight. And it's obviously also the darkest moment of their life,
Starting point is 00:20:57 the period of maximum pain. There's this concept in ancient Indian traditions called Kala Chakra. It's like the idea of the wheel of time. You have this endless cycle in the universe of creation, destruction, and then rebirth. And it's that period of destruction and that knowledge that rebirth is on the other side of it.
Starting point is 00:21:16 The knowledge that as Rumi says, the wound is where the light enters you. That is sort of what allows you to actually have that rebirth on the other side. I mean, yeah, before the Phoenix can rise, it has to burn, right? So these ground zero, you know, come to Jesus moments are actually divine moments in which we suddenly have this willingness and opportunity to reconstruct our lives
Starting point is 00:21:38 in new and interesting ways. But that choice is always available to us. Like you don't have to have that happen to you in order to make change. And yet it seems that we're hardwired to need that in order to kind of make that mindset shift and follow it up with action. It's very uncomfortable to ask the questions
Starting point is 00:22:00 when you're not having that dark moment, right? It's like the idea that it's much harder to be on a good path that isn't yours than it is to be on a bad path. A bad path screams at you every day to make a change. That's the rock bottom moment. You're like, I have to make a change in my life. The kind of like, okay, the good path that isn't quite yours
Starting point is 00:22:20 is much harder to make a change from because there's a lot of things that are telling you that it's fine, that it's good. There's kind of the, there's the tension that exists. And so I've often found there's a couple of questions that help. I mean, one is Mark Twain is kind of famously purported to have said, it ain't what you don't know
Starting point is 00:22:37 that gets you into trouble. It's what you know for sure that just ain't so. Asking that more regularly in your life, what do I know for sure that just ain't so, asking that more regularly in your life, what do I know for sure that just ain't so is a pretty helpful exercise because there are things that you automatically assume about your life that just aren't real. They're just completely fabricated.
Starting point is 00:22:55 And what if you believed the exact opposite? Every time I told myself that I wasn't smart, what if I flipped that on myself and just said, what if I believed that I was extraordinarily intelligent?, what if I believed that I was extraordinarily intelligent? What would be the decision that I would make here? And how might that look different than what I'm currently doing and operating? Well, that's challenging your operating system
Starting point is 00:23:14 and your default assumptions, but that also gets into kind of curiosity and imagination, which you write about in the book. And I kind of want to return to, but just to kind of follow through on this idea of the relationship between traumatic life moments and change, when I think about your story, so I see you just kind of like fast forward
Starting point is 00:23:35 through your trajectory. You're this upwardly mobile guy who's got all this stuff going for him. You're at Stanford, you're playing ball, you get injured. So there's a little bit of self-reflection that occurs with that. But fundamentally, you're playing ball, you get injured. So there's a little bit of self-reflection that occurs with that. But fundamentally you're interested in that traditional path of upward mobility.
Starting point is 00:23:51 So you go into finance, you end up in private equity, you're being paid very handsomely. Where is the traumatic event that catalyzes, you know, the dramatic life pivot because it appears or it feels a little bit like you are one of those people who volunteered for it. But my Spidey sense is there's more going on in the personal story.
Starting point is 00:24:12 And maybe you had to meet your maker in a little bit of a more profound way than comes across in kind of how you share publicly. Yeah. There's a lot that goes on under the surface in people's lives that we don't see. You obviously know this, and your own experiences, people you've interacted with.
Starting point is 00:24:31 I made every decision from the time I was 15 until the time I was about 30 years old to try to create this appearance of that upward mobility, to try to achieve those markers of success that would lead to the external affirmation that would, I thought, make me feel good, that would destroy that insecurity, where I would one day wake up and feel like I made it,
Starting point is 00:24:53 I've arrived, this is great. And on that entire journey, which was largely grounded around these external markers of success, money being the main one, everything looked like it was going well on the outside. And on the inside, everything was slowly, but steadily falling apart. And that included everything from my relationship
Starting point is 00:25:15 with my wife, who is the most important person in the world. You met in high school, right? Like you guys have been together for a very long time. Since I was 15 years old. My relationship with my wife was really suffering for a very long time. Since I was 15 years old. My relationship with my wife was really suffering for a number of reasons. The biggest one being that I feel like I was living someone else's life.
Starting point is 00:25:32 And when you do that, it takes a lot of energy to play a role. And when you play a role, you can't be authentic to yourself and your relationships. My relationship with my parents was suffering. I was living 3000 miles away, seeing them once a year. Obviously it's come through, but very close with them. And that was painful and something that was being masked.
Starting point is 00:25:51 My relationship with my sister was almost non-existent. I had created this dynamic of resentment and competitiveness in our relationship because of what I mentioned earlier that was harming it. My health was suffering. I was drinking six, seven nights a week, partially for work and then partially just to feel some level of numbness and escapism. My mental health was suffering. All of these other areas of my life and I started to just have this
Starting point is 00:26:16 sensation really when COVID hit in 2020 that I was winning the game. Everything said I was winning the game. Like this is what winning looks like. You're getting promoted, you're making more and more money, you look like you're successful, you have a house, you have a car. The things that I thought I wanted when I was 20 years old, I had them. And I had this sensation of, is this it? Is this the moment I'm supposed to feel happy?
Starting point is 00:26:39 And the most formative moment of this entire journey came in the middle of May in 2021. I went out for a drink with an old friend who I hadn't seen in a while. And we sat down and he asked how I was doing. And I said, good, I'm busy. It's kind of the stock response that we give people, you know, the like, punt the question.
Starting point is 00:27:01 And he looked at me and sort of just looked through me and said, how are you doing? And I told him that it was starting to get challenging being so far away from my parents, wasn't seeing them, our relationship was withering. And he asked me, how old are they? And I said, they're in their mid sixties. And he said, how often do you see them?
Starting point is 00:27:21 I said, about once a year. And he looked me square in the face and just said, okay, so you're going to see them 15 more times before they die. And I remember just feeling like the whole room closed in, like I got punched in the gut. And it wasn't about our relationship in that moment. It wasn't about anything other than the fact that I had the realization that the time I
Starting point is 00:27:54 had left with the people that I cared about most was so finite that I could count it on a few hands. And I realized in that moment that if I continued living the way I was living, I was gonna wake up in 50 years and wonder what the fuck just happened. And that night I went home, had a few more drinks, and I passed out on the floor of our house.
Starting point is 00:28:33 The next morning, my wife found me there and obviously was concerned. And I got up and just told her that I thought we needed to make a change. And this came at a time in my relationship with my wife that was really challenging. We had been trying to conceive for about the prior year and unfortunately had been unable to. You know, and that's a, it's something that a lot of people don't talk about publicly. There's a stigma associated with it. We bottle it up, we keep it to ourselves, and that's what we had done. And I felt like my wife was carrying that as her burden.
Starting point is 00:29:16 And I was not man enough at the time to help carry that burden or to accept it as mine to carry with her. So in that moment, her acceptance of this idea that we needed to make a change was the most powerful thing in the world to me. This idea that she sat there with me in the mud. She was there in that moment. She saw the pain that I was experiencing and she recognized it.
Starting point is 00:29:43 And we had built our entire life in California. She had a job, I had a job, things were good. Within 45 days, we had left California, sold our house, I had left my job and we moved back to the East coast to be closer to our families. And the most incredible thing in it all was that within two weeks of getting home, my wife got pregnant. It was just this full circle moment of when your life is out of alignment, when energy is out of alignment, nothing is possible. And when it comes into alignment,
Starting point is 00:30:26 suddenly everything falls into place as it should. I apologize for getting emotional. No, I appreciate the candor and the openness, man. It's a very relatable thing to go through. I think a lot of people go through, you know, their version of what you just explained. And, you know, we were talking earlier and you mentioned, you were talking about this idea of the arrival fallacy,
Starting point is 00:30:49 this premise that we make so many big decisions on is that we're aiming our compass in a certain direction on the assumption that when we arrive at that destination, that whatever it is that we're searching for, we will find it and it will make us feel how we've always wanted to feel. And when we discover that it doesn't, it's an existential crisis
Starting point is 00:31:13 and that can be your rock bottom moment or you can delude yourself that it's just over the next peak on the horizon. And that's what most people do. And the fact that you were able to kind of see this, early in life, frankly, much earlier than I was able to, is a credit to your self-awareness, but also like the depth of your value system.
Starting point is 00:31:37 Because it's one thing to say, oh yeah, I'm only gonna see my parents 15 more times. Well, I'll convince myself that I'll double that or whatever and just continue along your path. But that make that kind of significant life change is not a small thing. And the fact that your wife got pregnant after that, like, yes, alignment is important.
Starting point is 00:31:58 And I've seen that get played out so many times when you're out of alignment, you're banging your head against the wall and things just don't come easy if they come at all. And once you kind of course correct and you create that alignment between your actions and your values, suddenly there's a sense of ease
Starting point is 00:32:15 and things come towards you rather than you having to chase them. It's a beautiful way of saying it. The arrival fallacy is one of my favorite concepts and ideas because I felt my life was really a perfect example of that. There was always the end of your bonus, right? Like, oh, I'm gonna feel so different.
Starting point is 00:32:34 That's when I'm gonna have really made it and you're gonna get it. And then you get there and you immediately start just looking around like, what did other people get? Oh, why didn't I get this? Why didn't I get more? Oh, next year is gonna be even better. I can get more that next year. And you constantly have that feeling of the never enough to every area of your life. You're just feeling like
Starting point is 00:32:53 it's this constant treadmill. And after my son was born, I had this experience. I was walking him around out for a walk one afternoon. He wouldn't sleep other than when we pushed him in a stroller. So I was out for a walk with him and this old man came up to me and approached me on the sidewalk and just said, I remember standing here with my newborn daughter. She's 45 years old now.
Starting point is 00:33:18 It goes by fast, cherish it. And in that moment, I had this sensation of this is it. Like the good old days are happening right now. And in that moment, I had this sensation of this is it. The good old days are happening right now. I'm gonna be 90 years old someday, hopefully, and look back on this as the good old days that I'm living in. Like I have actually arrived in this moment
Starting point is 00:33:35 and there's nothing more that I want. And I can't fully articulate the feeling of peace that comes with that, the feeling of acceptance that comes with, this is where I wanna be, there's no place I would rather be than in this present moment with these people. And I feel like since then,
Starting point is 00:33:53 I've been able to harness that, I've been able to find that in different areas of my life. I'm no longer sitting one-on-one having a conversation with someone worrying about the email I'm missing or checking my phone or thinking about what the next thing is that I need to do, having that stress. I can be present with people. And the impact that that has,
Starting point is 00:34:14 the ripple effects into every area of your life are profound. I own a bunch of spectacles. I own a bunch of spectacles and I made the grave error the other day of donning a normal non-ROKA pair on my indoor trainer when I was riding my bike indoors. And I got to tell you, it was a disaster. Every three to five seconds, I had to take my hands off the handlebars and push my glasses back up my nose until I got so frustrated I just tossed him aside. This is the dilemma of every active but optically impaired person I
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Starting point is 00:35:59 This show is sponsored by BetterHelp. As we enter 2025, we each have 365 blank pages waiting to be filled. So maybe you're ready for a plot twist or perhaps there's a chapter of your life you've wanted to revise. But it's not about resolutions that fade by February. It's about becoming the author of your own story. Therapy can be like having an editorial partner on this journey.
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Starting point is 00:36:56 You complete a questionnaire to match with a licensed therapist and you can switch therapists at any time without incurring extra costs or any charges. Write your story with BetterHelp. Visit betterhelp.com slash rich roll today to get 10% off your first month. Well, as somebody who has kids that are older, I can tell you that that's true. My oldest isn't 45 yet, but he's 29.
Starting point is 00:37:28 And my youngest is 16 already. And it is like, I can't, she was a baby yesterday. And you talk about this in the book, this idea also that you think that your kind of role as a parent is a more extended period of time than it actually is, because by the time they get to be 12 or 13, like it's kind of like they, in a healthy way,
Starting point is 00:37:49 start to differentiate from you and then their life becomes about their friends and other things as it should. But the point is like, you don't have that much time and those moments are really precious. So to be able to see that and value it and follow it up with like not just actions, but like big decisions that basically drive your life in that direction.
Starting point is 00:38:13 Yeah, there's this concept from ancient Greece that there are two types of time. They had two words for time, Kronos, which is linear kind of the normal way that we think about time. And then Kairos, which is this idea that there are specific moments in time that have higher importance.
Starting point is 00:38:28 They're elevated moments. It's this qualitative textured nature. And that is very true for your own life. There are moments, there are windows of time where certain people, certain things carry higher importance. And unfortunately we live in a world where people love to say later, right? You're on the chase for something.
Starting point is 00:38:47 You're on the chase for whatever your professional ambition is. So you say later a lot. You say, well, I'll spend more time with my kids later, or I'll focus on my health later, or I'll, you know, build these relationships later, spend time with my parents later. And unfortunately, later is just another word for never. Because by the time you're ready to do those things, they're no longer there. Your kids aren't gonna be eight years old later.
Starting point is 00:39:09 You're not gonna have your health in the same way when you're 60. Your parents may not be around later. And that is the fundamental tension that we all need to ask more questions about to navigate. It's like, how do I balance my desire to build something, my desire to go after some of these ambitions that I have for myself
Starting point is 00:39:27 with the fact that these moments are passing you by if you're not present in them. So you contextualize all of this in terms of these five different pillars of wealth and your own journey kind of emerged out of realizing that by focusing on this singular idea of what wealth was, was driving you away from being truly wealthy, which is to be happy and fulfilled and purpose-driven and the like.
Starting point is 00:39:52 The first pillar of which that is the first one in the book is time, you know, I'm like, I wanna dig into that because I think that's the most interesting of all of these pillars. But in your kind of synthesis of how you practice or kind of set your life up so that all five of these types of wealth are getting properly nourished, you talk about the difference between looking at it
Starting point is 00:40:16 like an on-off switch and more of like a dimmer switch and where you're kind of focusing your energy in terms of your relationship to these various pillars is very much a function of what stage of life you're kind of focusing your energy in terms of your relationship to these various pillars is very much a function of what stage of life you're in. Yeah, so this is a really important concept because the traditional wisdom, go back to the idea of like the cultural standards around these things, is that your life
Starting point is 00:40:38 and these different areas of your life has to exist on an on-off switch. People will tell you, you can only pick a couple, right? You have to pick professional life and social life, or you have to pick your health and your professional life, and you can't have the other things. You can't have the family that you want during this window. You can't have the health you want if you're focusing on one area. And I just fundamentally reject that. The reason is because I think you can operate on dimmer switches. And what do I mean by that? Well, there are ways where you can make progress in every area of life by just focusing on
Starting point is 00:41:11 the one or two things that have real leverage to them. You don't need to go to every single friend dinner or cocktail event or party in order to progress your social wealth, in order to build relationships. What you need to do is send the text when you're thinking about the person. What you need to do is take time to call someone for five minutes to check in on them. It's the tiny little actions that we can make progress
Starting point is 00:41:36 in all of these areas. So again, viewing them as a dimmer switch, not falling into the trap of saying, well, if it's not optimal, then it can't be beneficial because that's just not true. We know it's not true for health. If I don't have an hour and a half to go work out, that doesn't mean I should do nothing.
Starting point is 00:41:51 It means maybe I should go for a 15 minute walk or a five minute walk because in all of these areas of life, the reality is that anything above zero compounds, but you have to do it daily. You have to actually show up and punch the clock on all of these things. And the other concept you allude to, which is really central to the whole idea of the book is this idea that your life has seasons and what you prioritize, what you focus on in any one season may change.
Starting point is 00:42:22 And the important part of that is you don't have to optimize everything at every point in your life. Your 20s are actually a great time to prioritize building financial wealth, building a financial foundation that will compound for the rest of your life. Your 30s and 40s when your kids are young may be a great time to prioritize the time and energy you give to them because they're not gonna be five, 10 years old for the rest of your life. And you can shift across them.
Starting point is 00:42:50 The most real example I have of this is my wife. She's a high powered fashion designer, was like rising through the ranks in a very competitive industry, working at Gap and a bunch of the different companies underneath that umbrella. And when my son was born, she made the decision that she wanted to really prioritize being a mother.
Starting point is 00:43:10 That is something that comes with a lot of stigma attached to it in the society we live in today, particularly if you live in certain areas of the country. A lot of people were constantly questioning her about that. They say, oh, you're just gonna be a mom. Just a mom is the phrase that people use, which by the way is a very hurtful phrase that I think we just need to abolish.
Starting point is 00:43:32 Because from having seen it now and understanding what that means, the hardest job in the world and the most important job in the world and not valued by society in the way that it should be. Taking that aside, the idea that life has seasons was extremely empowering to her because it's a reminder that she can prioritize my son
Starting point is 00:43:53 during this season and any other children we may have and then return to these other areas of focus in a later one. She can go start her own line in a later season. She could go back and work in a later season. You're not making a decision that has to perpetuate for the rest of your life. You have these comings and goings.
Starting point is 00:44:10 The idea that you can turn this dimmer switch and that there are these seasons or chapters in your life is an important story to replace the more traditional story which is, well, if I do this, then I can't do that. Or if I do this, it comes at the cost of this. Or the case of the very ambitious 20 something who's approaching their, this decade, doing exactly what you're recommending,
Starting point is 00:44:41 which is like, I'm gonna go all in, I'm gonna start to build my career and create a foundation for, you know, kind of financial viability. But the problem is that all of this sort of incentives that surround that young person begin to capture them. And then you get stuck. Like you're, I mean, just imagine the associate
Starting point is 00:44:59 at a law firm and then it's just up the partner track. And the higher you move up, the harder it is to leave. And often if there's unhappiness, you know, with that person, they're going to compensate by overspending, you know, further imprisoning themselves to a life that is at odds with the thing that, you know, is ultimately gonna make them happy. And that just becomes, you just becomes more and more distant.
Starting point is 00:45:26 So that's the trap. And that's the trap that a lot of people fall into that I'm so grateful that I was able to find an escape hatch from and as did you. It's pretty common. And all of your social environment at that point is keeping you stuck in that. Because if you leave,
Starting point is 00:45:44 then you're threatening your status within your tribe. And it's also not well-received because if the people that you're working with also aren't unhappy, then suddenly you're a threat. Yeah. Because if you could do it, then they can do it. And it all comes back to the scoreboard. Maybe it's because I come from an athletic background,
Starting point is 00:46:02 but I think of scoreboards with all of this. And money was the default scoreboard. It is the default scoreboard. Maybe it's because I come from an athletic background, but I think of scoreboards with all of this and money was the default scoreboard. It is the default scoreboard. It's partially because it's so easily measured. It's very easy to just put a number to money and to say like, okay, here's my scoreboard. And what happens is Peter Drucker said this, what gets measured gets managed. The thing that you can easily measure ends up being the thing that you optimize around. It's the only thing that you focus on. And part of what I'm trying to get at is that we need to fix our scoreboard. The scoreboard is broken. There are all of these other areas of your life that are not on your scoreboard. So as a result, you play the game wrong. You do the thing. You continue to chase whatever the nicer thing is.
Starting point is 00:46:40 You chase the CS Lewis, the inner ring. like you keep peeling the onion and keep going further and further until there's nothing left. And I really think that what I'm trying to push and what I'm trying to make sure that people understand when they come away from this book is this idea that your scoreboard has much more than money on it. And when you make a decision, when you think about designing your life,
Starting point is 00:47:00 when you manage these different seasons, you need to factor in all of the different types of wealth. If someone came and offered you $100 million today to do something for the next three years, you would, if on the old scoreboard, say, hell yeah, right, $100 million, that's the only thing that matters to me, money. But now if you were to tell the person,
Starting point is 00:47:19 well, you're gonna have to work 120 hours a week, you're gonna be away from your family 350 days out of the year, you're gonna work on work 120 hours a week. You're gonna be away from your family 350 days out of the year. You're gonna work on things that you absolutely hate and you're not gonna be able to work out. Well, hold up. Now the whole calculus changes, right? There's a whole lot of money.
Starting point is 00:47:34 Yes, that's good. But there's a whole lot of bad on these other types of wealth. I'm not seeing my family. Social wealth takes a hit. My purpose and meaning and my growth is gonna take a massive hit because I'm working on things I hate.
Starting point is 00:47:44 My health is gonna take a huge hit because I'm working on things I hate. My health is gonna take a huge hit. My time is gonna be effectively zero. So a decision that felt really obvious on the old scoreboard feels obvious in the other direction on a new scoreboard. And so it's an importance of understanding what that scoreboard is for your life. The things that you are going to prioritize
Starting point is 00:48:00 and think about as you make these different decisions. You say in the book, you know, there's this idea that when you have that kind of awakening moment that you realize like the sort of standard thing to sort of say about it is, I realized I was playing the wrong game. And you're like, no, you were playing the game wrong. Like there is a game, you're just thinking about
Starting point is 00:48:20 what that game is incorrectly. And the game is what? I presume if you were to define it, it's to lead your life in a way that you're moving in the direction towards happiness, love, connection, meaning, purpose, like all of these things that the happiness scientists, people like Arthur Brooks are talking about
Starting point is 00:48:41 are the drivers of feeling like you're fulfilled in the life that you're living. I wanna wake up on an average Tuesday and be excited to live my life. Honestly, at the end of the day, that's how I think about it. Because Tuesdays normally suck in a normal world. And Monday, you kind of have some energy,
Starting point is 00:48:59 but Tuesdays usually suck. I wanna wake up on Tuesday morning and be excited to live my life. And that's by the things that I'm doing, the people that I'm gonna be around. And this book is really like a thesis on like, okay, let's work our way towards this in a very systematic way that involves pillars,
Starting point is 00:49:16 techniques and this scorecard like idea. But it really begins with this idea of having a, like all of it snaps into focus when you have this, what you call like life razor. So explain what that idea is. Have you seen Apollo 13? Sure. So in Apollo 13, the climactic scene,
Starting point is 00:49:37 you know, they're in space and they have to reenter the atmosphere. And they have to do it without the help of any of their computer equipment. And so they're trying to figure out how they're gonna do these like series of complicated calculations in order to do this, because if they come in too shallow,
Starting point is 00:49:52 they're gonna skip off into space, and if they come in too steep, they're gonna explode. And there's this one moment where Tom Hanks says, he thinks he knows the way to do it. He kind of pans the ship, and all you see is this tiny triangular window, and he pans pans it and the earth just comes into the center of the window. And what he says is that if he can keep the earth in the window as they go, it's going to keep them on the exact right trajectory in order to reenter the atmosphere safely. What that really
Starting point is 00:50:19 is, is what I refer to as a life-raiser. It's a single point of focus that allows you to cut through the noise in life. It allows you to navigate through whatever chaos, whatever storms might hit your life and come. And I think the best tangible example that I've seen recently was Mark Randolph, he's one of the founders of Netflix, shared this piece that he had this concept
Starting point is 00:50:43 of never missing a Tuesday dinner. And that no matter what, he was starting Netflix, things were crazy, chaotic, running this startup. No matter what, at 5 p.m. every Tuesday, he would leave and go have dinner with his wife. And when I spoke to him, the thing that really comes across is that it's not about the dinner, it's not about the date, it's about the ripple effects into all of these other areas of life. It's about the identity that it's not about the dinner, it's not about the date, it's about the ripple effects
Starting point is 00:51:05 into all of these other areas of life. It's about the identity that it defines about who you are. And so when I talk about this life-raiser concept, what I talk about is the concept that you need something like that. You need your version of the Tuesday dinner or the earth in the window. You need the single defining statement that you can make
Starting point is 00:51:24 about who you are make about who you are and about how you are going to make decisions in your life. Mine is that I will coach my son's sports teams. And there's really three characteristics that I would say come across with that. One is that it is controllable. I can control whether or not I am able to make the time to do that and show up and be there.
Starting point is 00:51:46 The second is that it is ripple creating, meaning that has ripples into every other area of my life. It means that I have to be the type of father that he wants to have around. It means that I'm the type of husband that my wife is proud to see with my son. It means that I'm the type of community member that shows up and supports the other children.
Starting point is 00:52:04 It has ripples. And then the third one is that it is identity defining. Meaning I can say, what would the type of person that coaches my son's little league teams do in this situation? If someone comes and offers me an attractive financial opportunity that may come with some hit to my character,
Starting point is 00:52:23 or maybe morally ambiguous. Well, what would the type of person who coaches my son's sports teams do? I probably wouldn't do that because I will never jeopardize my relationship with my son and how he thinks of me and the respect he has for me in this moment for whatever amount of money.
Starting point is 00:52:40 You're creating an archetype and then you can measure your decision-making against that archetype, which I think is super helpful. And you have all these examples of other people's versions of it. Like I'm the kind of person who never lets a friend cry alone, or I'm the kind of person who reads my kids bedtime stories
Starting point is 00:52:57 or whatever it is, it's a rubric, right? So when you have those difficult decisions where it's not a 10 or a one and you're in that middle place and it's easy to tuck yourself into something that you probably shouldn't do, it's a measuring stick that kind of tells you exactly where you're at.
Starting point is 00:53:12 Although I will say, Sahil, there is a little bit of a flaw in your life-raiser, and it has to do with the control piece. One is your son's two, right? Two and a half, yeah. So it's presuming, it's presuming that your child is gonna wanna play sports. Totally.
Starting point is 00:53:29 It could be anything though. It could be that a coach is drama. If I know anything, it's that God is gonna throw you, like to use a baseball analogy, he's gonna throw you a curve ball. I believe that. He's already thrown several. Obviously it's adaptable.
Starting point is 00:53:42 Like the ethos of it I get, and I think it's easily applies to anything. It creates like a very clean visual. And I'm sure if your son decided he didn't wanna play sports and he wanted to be a theater kid or whatever, it's the same idea applies, right? Yeah, I'm excited to be a ballet dad.
Starting point is 00:54:01 As the new kind of young dad who was a college athlete, it's like, well, of course he's gonna play. Yeah, I mean, we create our own, we definitely impose our own will on how we think our kids are gonna, what they're gonna be excited about. If there's one thing I've learned, by the way, about being a dad that I've changed my mind on,
Starting point is 00:54:19 it's that you can't teach your kids anything. They come out with a kit and you just have to hope to embody the values that you want them to learn. You share a set of values, you put guard rails up and you rush in to support where their curiosity leads them. That's a beautiful way of articulating it.
Starting point is 00:54:36 And it's not going to lead in the direction that you suspect. Or that you want it to. Or that you want, yeah. My mom still wants me to go to medical school. Yeah, me too. I'm suspect. Or that you wanted to. Or that you want, yeah. So- My mom still wants me to go to medical school. Yeah, me too. I'm 58. I mean, I swear to God until I was 30,
Starting point is 00:54:51 my mom would annually ask me, am I sure I don't wanna go for medical school? Yeah, yeah, yeah. The Indian genes die hard. So yes, your job is to rush in and to support their curiosity. But it sounds like you had really good role models for that, your parents did that for you, right?
Starting point is 00:55:09 Yeah. And then, and this is the key, is detaching from any kind of expectations around what that might look like. And that's where you run into issues around like, cause you know, when you have a kid, you're always imagining like, oh, it's gonna be like this,
Starting point is 00:55:27 or what happens if this happens or whatever. And in my experience, it's always different from that. And your kids become your greatest teachers and they push you in directions that, you know, you didn't see coming. And like anything, those are your growth opportunities. Yeah, I think we also either reject or amplify what we experienced with our own parents
Starting point is 00:55:53 in how we parent our children. And I think about my own father and my relationship, and my dad is in many ways my best friend in the world. I don't tell him that. I don't feel like I've articulated that to him. Even now I'm reflecting in this moment that it's a shame that I say this to you and not to him. And I should probably leave here and tell him that.
Starting point is 00:56:15 And I just think about our relationship and how so much of who I am as a person has formed through seeing the way that he showed up for my sister and I as a father and as our number one cheerleader. The way that he worked as hard as he worked on things that lit him up throughout his life but then always had time to come in the backyard and play catch with me in the evening when I'm sure he was exhausted when I'm sure that he didn't want to, and I'm sure that he knew he had work to do late at night. And I remember a formative moment in our relationship
Starting point is 00:56:51 when I called him to tell him that I could no longer play baseball. My shoulder was hurt, this is my last year at Stanford. And I was so scared to make that phone call. I had totally come to terms with it. I mean, my arm hurts so bad every time I threw, I knew I couldn't do it anymore. But I was so nervous to make that phone call
Starting point is 00:57:10 because so much of our relationship had been built on a baseball field. From the time I was two years old playing catch with him until the time I went to college and all of those years, he had been my throwing partner, he had been my coach, he had been my supporter, he came to all of our games and I was scared that he would be disappointed that it was gonna hurt him that I was walking away from this and I remember calling him and telling him and
Starting point is 00:57:38 He just said I don't care. I can't wait to Be in the front row cheering you on and whatever you do next in your life. And the way that he's lived that out, he showed up at the finish line, surprised me at my first marathon. Like stupid, right? Like I'm just an adult running a marathon.
Starting point is 00:58:00 The way that he shows up at the front row of like events that I do now when I'm speaking or something that's going on, he's sitting there taking notes in the front row so that he shows up at the front row of events that I do now when I'm speaking or something that's going on. He's sitting there taking notes in the front row so that he can give me feedback, so that he can be a partner to me. That is just amazing. And I know that it's because he's rejecting what he felt he was missing from his father. And I'm the beneficiary of that. So now when I think about my own relationship with my son, it's amplify the hell out of that. Do those things to the 10th degree,
Starting point is 00:58:28 continue to push that legacy forward in time. Because that relationship, I mean, that father-son connection is such a powerful one if we allow it to be. Yeah, you guys went to India, I know, recently also, and yeah, you shared with me, he's like taking notes at some talk you were giving or something like that.
Starting point is 00:58:48 I was like, wow. He was sitting in the front row. Someone took a picture of him taking notes in the front row of my event. And you're like, my dad's a Harvard professor. My dad is not, he doesn't need a whole ton of advice. It's like a Harvard professor sitting there studiously taking notes.
Starting point is 00:59:02 And it's because after the event, he's gonna sit down with me and he's gonna say like, oh, I really liked how you said this. I made a note that I thought you could have articulated this slightly better. He's giving me feedback, right? He's a truth teller in my life. And that goes back to what I said at the beginning,
Starting point is 00:59:15 high expectations. He has expectations of me that I'm going to be the best speaker in the world, that I'm gonna deliver this message better than anyone else. But he's pairing that with high support. He's sitting there actually doing the work and spending the time to help me meet those expectations that he has. High expectations are tricky though.
Starting point is 00:59:34 You know, it is interesting that when you got injured playing baseball, that you had trepidation around calling him. Like even with all of that support, high expectations are, you know, come with all kinds of pressure and that sense of, you know, disappointment that comes if you can't measure up. I felt a lot of pressure my whole life. I still feel pressure, a lot of it self-imposed.
Starting point is 00:59:58 I fundamentally have always believed that I was capable of more than what I was doing. And that's a double-edged sword, man. And you probably see it in almost everyone you talk to on the other side of this table. I know you felt it in your own life, that desire to go and perform, to build, to execute, to do those things. that desire to go and perform, to build, to execute,
Starting point is 01:00:31 to do those things, it's challenging to wrestle that beast in the other areas of your life, because you have the tendency to just go head down on something and wake up a year from now, and you let every other area of your life get hurt. And so it's why this book has been such an important idea to me, I mean, what I say is that it's a manifestation of my own journey. It's me wrestling with this stuff every single day.
Starting point is 01:00:53 I by no means have figured everything out and lived the perfect life. And I try to get that across in everything that I share. Like I'm not a guru. I don't have all the answers for you to live the perfect life. What I can do is help you ask the right questions. I can help you wrestle with the questions
Starting point is 01:01:10 because that's the journey I'm on. It's wrestling with the questions every single day, screwing up, coming back from it, getting better hopefully over periods of time. Yeah, to be somebody who knows that they have a certain amount of potential and if they plug in in the right way, it could be a certain thing, but the cost of that, like weighing that against the cost of that, you know, and the value set around parenting and your marriage
Starting point is 01:01:37 and all those other things that you know will get sacrificed as a result and still making the decision to, you know, step back from that thing and perhaps not lean all the way into your potential and direct it in a different way that is consistent with, you know, these other values so that they don't get sacrificed. A big part of it for me, what has helped, and I'll offer it in case there's someone out there listening that this might help is shifting my purpose away
Starting point is 01:02:07 from being something that was my job to something that I can connect to every area of my life has been really helpful. There's this common tendency to say that like, you have to find purpose in your work. And I just reject that fundamentally. I think you need to be able to connect your work to your purpose, but your purpose can be a higher order
Starting point is 01:02:30 thing that you can connect to multiple areas of your life. My purpose, as I define it today, is to create positive ripples in the world. And I can certainly connect that to my work, writing to things I share that I think I can create action and people that will improve their lives. But I can also really connect that to my work, writing to things I share that I think I can create action and people that will improve their lives. But I can also really connect that to the house I am building, to my family, to the people, to my wife,
Starting point is 01:02:51 to my son, to the ripples that I can create in their lives, my parents' lives, my sister's life, and our relationship, how it's transformed. That is really important to me because then I can channel ambition towards any of those areas. It's not only towards work. Right, that mission statement is like a holding company
Starting point is 01:03:09 for all the other sort of things that, all the other aspects of your life, like it's an umbrella concept, it's broadly applicable such that, you can measure your decisions against it and your mission is not exclusive to some type of vocation. Yeah.
Starting point is 01:03:29 One thing I do wanna say and mention, because I just said it, now it's triggered the train of thought, is I alluded to earlier the fact that I created this really harmful dynamic with my sister for many years of my life, almost entirely my fault in hindsight, because I had created this story
Starting point is 01:03:50 that she was the smart one and I wasn't. And that manifest as a lot of resentment and competitiveness towards her, where I constantly felt like she was making me look bad. And like, why was she achieving all of these things? And I wasn't able to do those. And it made me feel a sense of resentment towards her. And as a result, we almost had a non-existent relationship
Starting point is 01:04:13 for the first 30 years of my life. And it made my parents so sad. My mom, I can't imagine the sadness that she felt around that for many years because your sibling is the one person who knows you from start to finish. Like they are there through your entire life. Your spouse won't be, your parents won't be.
Starting point is 01:04:31 It's, that's the person that you're in the trenches with your whole life. And something really beautiful happened after this whole life transition, which was that my sister had a young son 11 months before my son was born. Roman was born in May of 2022. My sister and her husband and their son
Starting point is 01:04:53 came down to visit us. And I was holding my son and she was holding hers and we took a picture together. And I just remember in that moment, having this crazy sensation that my sister and I were meeting for the first time. This idea that you can know someone for your entire life, but have never met them truly,
Starting point is 01:05:16 never seen them in the way that they are meant to be seen. And it was a reminder to me in that moment that there are going to be people and relationships that for no apparent reason blossom in a new season of life in a way that they never did. People that are going to love you deeply that you literally have never met yet. What does your sister do now? She is an entrepreneur. She remains very high achieving. She is a great, great mom and the CEO of a health technology company in Boston. Yeah. I'm in the process of
Starting point is 01:05:54 reconnecting with my sister. You know, we weren't like, you know, out of communication, but that relationship is not as, has not been as nurtured as it could have been. And I'm in the process of trying to reconnect that. It's a really powerful thing. I mean, I would say I would have characterized my sister and my relationship the same way you just did. It wasn't an outwardly, you know, there wasn't outward animosity.
Starting point is 01:06:23 It was just this under the surface bubbling where you feel this layer of tension that exists. And I had to explicitly say, I mean, I had to say something to end that. Just say like, look, I, for many years of my life, I felt this way. It was created through my own stories that I was telling myself.
Starting point is 01:06:42 I'm now come to terms with that, changed that and have shifted the narrative in my own life. And I apologize and I want us to be there for each other. That's the person who my son will go to if something were to happen to my wife and I. I mean, it's such an important relationship and there's just so much beauty in that recognition that just because a relationship hasn't been there
Starting point is 01:07:09 doesn't mean that something can't change, that you can't take an action to change. So much of our feeling of being stuck in life, my own sensations of being stuck in life prior to this transformation are driven by this idea that you cannot, you don't feel you have the power to take an action and create an outcome in any area of your life.
Starting point is 01:07:30 You don't feel like you can do something and create the desired outcome. And once you start to feel that, you start to change that and realize that you can do something, you can create an outcome in your life. It doesn't matter where that starts, that bleeds into every other thing that you do. Because that recognition changes everything. You reassume the outcome in your life. It doesn't matter where that starts, that bleeds into every other thing that you do. Because that recognition changes everything.
Starting point is 01:07:47 You reassume the power in that moment. You recognize that you do have control over the outcomes that you have in your life. We're brought to you today by Calm. At the start of every new year, we hear a lot about resolutions. But what's the plan? And how are you going to handle the stress when life interferes with your plan? Well, don't worry about it because I got what you need all in one place, and that place
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Starting point is 01:08:52 which cover everything from financial stress, habit building, and even stoic wisdom, courtesy of Ryan Holiday, all of which have been very meaningful inputs in my commitment to sustainable growth. So stress less, sleep more, and live better with calm. of which have been very meaningful inputs in my commitment to sustainable growth. So stress less, sleep more, and live better with Calm. For listeners, Calm is offering an exclusive offer of 40% off a Calm Premium subscription
Starting point is 01:09:14 at Calm.com slash Rich Roll. Go to CALM.com slash Rich Roll for 40% off unlimited access to Calm's entire library. That's calm.com slash richroll. You strike me as somebody who has a lot of self-awareness and always has had a lot of self-awareness. You wrote this open letter to yourself like 10 years ago. And there was one sentence in it that stuck out for me and where you write to yourself and you say,
Starting point is 01:09:55 you have a lot you hide from the world. You're insecure. You compare yourself to everyone but yourself. You're so afraid to fail that you always seem to choose the safe path. You've got work to do, don't run away from it. So it takes a lot of self-awareness to even think about the idea of writing an open letter to yourself
Starting point is 01:10:18 to be open 10 years later. And it takes a lot of self-awareness to have that sense of who you are and what your challenges are, you know, at a younger age. And you seem to now have a lot of self-awareness around like around the sort of growth that awaits for you. And I'm bringing this up because I'm interested in your thoughts around the relationship
Starting point is 01:10:46 between self-awareness and the ability to change. There's this sort of adage in recovery that self-awareness will avail you nothing. And I don't know if that's true. Like I think self-awareness is really important because you can't make that change until you can kind of see yourself clearly, but self-awareness is not enough.
Starting point is 01:11:08 It's sort of like going to therapy and just talking about your problems and never actually putting them into motion. And I think sometimes self-awareness can get in the way because you're just talking about the thing and you delude yourself into thinking you're actually doing something when you're just sort of like engaged
Starting point is 01:11:24 in some kind of mental masturbation about it. Yeah, it's almost like the mental model I would frame it around is like this idea that there's an awareness action gap. And the goal in life is to have a razor thin gap between your awareness and the action associated with that awareness. Most of us and me for most of my life,
Starting point is 01:11:47 you reference that 10 year old letter, there was an enormous gap between awareness and action. I didn't do anything about that for 10 years or almost 10 years. That was in 2014, I wrote that letter to myself. It was 2021 when I made the change, before I'd even opened the letter in my own life. And this is the problem with all self-help content, self-improvement in general is it's
Starting point is 01:12:14 dopamine from information. It's dopamine from awareness. You go read a book, you're like, oh, I read a book. I'm smarter now. Well, you didn't do anything about the book. You didn't do anything about the one thing that you learned. And it's the same for me when I write that letter, like you get the awareness and you feel good about yourself
Starting point is 01:12:30 because you have the awareness. So you go to the therapy session and you feel good about the awareness, but what are you doing about it? Where is the action? You need to shrink that gap that exists. And what I try to get across in everything I put out is what is the one tiny action that you can take right now?
Starting point is 01:12:49 Because sitting around and planning out the perfect action and how I'm gonna change the trajectory of my life in 10 years, I'm gonna do this, this and this, doesn't matter. What you need to do is create the like little bit of momentum today, whatever that tiny little thing is that you can do. And as I said, that's how you change your life.
Starting point is 01:13:06 That's where you convince yourself that like, oh, I took that tiny action and something happened. So I changed in some tiny way. It's the first thing I say to any young person who comes to me and says they're feeling lost in life is wake up early and work out for 30 straight days. You set your alarm at 6 a.m., 5 a.m., whatever time and wake up and do a workout. And it has nothing to do with making money, it has nothing to do with your career,
Starting point is 01:13:29 it has nothing to do with any of those other areas. What it has everything to do with is rewiring your brain to recognize that you can do a thing and create an outcome. And when you do that, when you convince yourself of that, you become completely invincible, unstoppable. It changes your relationship with your own potential because you see the results
Starting point is 01:13:47 and in the context of fitness and exercise, like you physically see yourself change, and 30 days is enough to have some kind of change that then kind of plants the seed and gives you that encouragement to then apply that skill across the board into other areas of your life. But truly the only time that you can practice it
Starting point is 01:14:08 is in the immediate moment. We're so captured by stories about who we are based upon the past and imagining, sort of caught up in a fantasy of what might happen. And we're asleep at the wheel in terms of actually living our life because the only moment it's actually happening is right now and this is the only moment
Starting point is 01:14:29 in which you have any agency to do anything about it. So we love to cast our gaze and talk about what we're gonna do tomorrow or these grand plans or what our to-do list is, but the brass tacks of it is atomic habits. That's what moves the needle. It's the tiny things that you do every single day anonymously that aren't sexy
Starting point is 01:14:49 and aren't gonna get traction on X where you're like a big rock star. But the truth is it's like, it's really mundane bullshit that actually moves the needle of your life. Yeah, I say that the boredom of routine is a tax on long-term success. We all create this impression that like the most successful people in the world
Starting point is 01:15:10 have these glamorous, gorgeous lives, like event to event, gala to gala, jets, yachts, all those things. When in reality, what underlies all of that is this boring daily grind of the basics. There's every single day executing against those little things, those things that add up. And the big challenge is that the inspiration that you get,
Starting point is 01:15:35 the feeling, the dopamine hit from awareness or from information is perishable. If you don't go act on it right now, you will not act on it. It's like the whole idea of later. Not only is it perishable, it actually works at cross purposes with your goal because it convinces you that you actually already did something.
Starting point is 01:15:52 That's the problem, right? Like pull any self-help book off the shelf. If you actually did everything it said, your life is gonna get better, right? So why do we have a new one? Like every week there's a new, there's this like thousands of these books, right? They're all valid in some regard.
Starting point is 01:16:07 I'm sure there's universal truths that you can find on in every single one of them. The problem is we read them. And to your point, like sort of think that we've actually done something when all we've done is load ourselves up with information that ultimately is useless unless it's translated. It was funny because in the actual writing
Starting point is 01:16:28 and publishing process, this was a fairly significant point of contention that I really wanted this book to be filled with things that you can actually go and do. So you get the theory and the construct and the idea that these five types of wealth matter and you get all the awareness that comes with that, the information that comes with that, it leads to the questions that you're talking about with people.
Starting point is 01:16:50 But I want people to go and actually build these other types of wealth. And the construct that I had around that was to include these guides at the end of each section, these sort of battle tested science backed principles that can lead you to building these types of wealth and have this idea of like, here's the one week jumpstart, here's the thing that you can do right now. And a lot of the publishing houses when I was originally pitching the book started to feel like it's too broad, it's getting too big. And you know this, the traditional publishing industry really wants you to get laser focused on a single topic. And it's why I think the meme has perpetuated
Starting point is 01:17:26 that most of these books are 15 page blog and then 175 pages of filler. And I really didn't wanna do that. I wanted something where people would actually change. I say that my purpose is to create these ripples. Ripples aren't created through awareness, through information. Ripples are created through action.
Starting point is 01:17:43 It's the actual rock hitting the pond creates the ripple. And you need people to go out and take action. You need, if it's normally 5% of people that act on a book, what does it look like for it to be 10? How does that change way more people's lives? How does it change the lives of the people they go out and interact with? Because if you read something
Starting point is 01:18:03 and you go interact with your partner a little bit more effectively, or you go spend a little bit more present energy with your child, or you show up to work with a little bit more energy, that has lasting effects for other people in your world as well. What do you think is the differentiator
Starting point is 01:18:21 between somebody who could read your book and then turn around the next day and start taking action and the person who reads it and doesn't like, do you have a sense of the qualitative difference between those two people? Like what is it that gets in most people's way? And what is the kind of unifying quality that people who actually know how to like kind of move their lives forward, hear the information
Starting point is 01:18:47 and go, oh, that'll make my life better. I'm gonna do that. Accountability, one person in your life that you're gonna be on the journey with around these concepts. I have time and time again found that environment is the thing that holds people back from making actual change,
Starting point is 01:19:04 from taking action in their life. And there are scientific evidence that the people you surround yourself with impact your outcomes. The Pygmalion effect is this idea that when people around you have high expectations for you, you rise to the level of those expectations. So the people you surround yourself with
Starting point is 01:19:20 are actually impacting your ability to change your trajectory. And if you can find one person that you're going to enact change with, that you're gonna have the little group text with where all you say is like done at the end of the day when you did the one thing, that changes everything. It's the reason 75 Hard is such a self-perpetuating idea.
Starting point is 01:19:42 It's not because the workouts are great or because reading 10 pages a day, it's because you create a community of people that are trying to grow together. And then you stick to it. You don't wanna let the other people down. You don't wanna be the one person that doesn't say done in the group chat.
Starting point is 01:19:55 So you keep doing it. But when you lack that, when you're on your own, it takes an incredible amount of energy when you're solo to do something. I mean, it's again, it's like, how hard do you work out when you go to a gym and there's a lot of people looking at you versus in your own house by yourself?
Starting point is 01:20:11 The quality of the people that you surround yourself with is when you talk about environment, I mean, that's a core piece to that obviously. And you're somebody who's been very conscious about the people that you kind of surround yourself with. And you also like in the book, like how many people, like you went out and like talked to so many just normal people, right?
Starting point is 01:20:36 Elderly people, people from all walks of life. And you tell these stories throughout the book, like what you learned from all of these people. So you're like actively soliciting wisdom and input from a wide swath of sources. Like, I know that like you're friends with Tim Cook and he's sort of a mentor, but to me, what speaks to your character more is like all
Starting point is 01:20:59 of these other kind of like anonymous people that obviously there was some commitment on your part to like go out into the world and spend time with tons of different people to help you figure out like how you were going to, you know, direct your energy. Yeah, I mean, do we really need another book about how billionaires are successful?
Starting point is 01:21:18 It's funny, whenever I tell people that I wrote this book, they're like, oh, so did you interview, you know, Tim Cook, or did you interview like all these really wealthy people? And I'm like, not really, because how is that relatable? How is that interesting in terms of how you can change your life today? It's aspirational maybe, but it's not relatable to what you are going to do.
Starting point is 01:21:37 The billionaire's life is not relatable to me, by the way, let alone to anyone else that's out there reading. What is relatable is Alexis Lockhart, who reached out to me in response to a newsletter, who experienced a tragedy of really impossible to comprehend proportions in her life, and who found a path coming out of that. And through that path has redefined what a wealthy life looks like to her,
Starting point is 01:22:07 who exemplifies the things that I'm trying to talk about in the book that I'm trying to get across. And when I think about, again, creating action, those are the stories that create action because you see yourself in them. The most important piece with all of this is I need to be able to find myself in someone in that book. I need to be able to see myself in someone, in book. I need to be able to see myself in someone,
Starting point is 01:22:25 in someone's story so that I can see, okay, there's the path, there's the thing, there's the thing I'm gonna attach myself to to actually go and create change. It shrinks that gap between the awareness and the action. And if there's one thing I've learned, it's that you can learn just as much, if not more from the conversation with your Uber driver than you can
Starting point is 01:22:46 the conversation with the billionaire. It just goes back to that idea of asking the right questions. And when you're interested in questions and not necessarily their answers, you'll be amazed what you can discover. And you talk a lot about listening, which I think is a skill most people are really poor at. Me included, by the way.
Starting point is 01:23:09 But if you learn how to do it well, it becomes like a superpower and the world becomes your university. Yeah, I recently spent time with the gentleman that founded Humans of New York. You know, that thing. Brandon Stanton. He goes up to people on the street
Starting point is 01:23:29 and just asks them questions. And he articulated it as when you are truly listening in a conversation, it's as though you disappear and the other person is free to be their full self and to share things. I thought that was such a beautiful way of articulating it because the tendency and the
Starting point is 01:23:46 standard is what's called level one listening. It's me listening, which is like I sit here and as you're talking, I'm just running these trains of thought. Everything you say, I'm relating to myself. You're talking about some run that you did. I'm like, oh, I should really run today. I haven't run yet. I need to do this.
Starting point is 01:24:02 It's like a form of conversational narcissism. Like I'm relating everything you're saying to something in my own life. And the point is recognizing it so that you can shift it, so that you can default to level two listening, which is you listening. It's me actually hearing everything you're saying, creating this map of who you are
Starting point is 01:24:22 and of your interests of the things that you care about. That's when I'm able to disappear and just allow you to show up as your full self. What was the most surprising thing that came out of all of those conversations that you had that ended up being an idea in the book that you didn't foresee? I mentioned Alexis Lockhart.
Starting point is 01:24:42 I was turning in the book. I was about a week away from turning in the book when I got an email from a woman in response to one of my newsletters. And I read the email and she told it, articulated some of her story. And I emailed my editor 10 minutes later and just said, I'm not turning it in next week.
Starting point is 01:25:03 I need to spend more time with this woman. That story, I would argue is the most impactful story that's told in the book. Because the way that she articulated the loss that she experienced and the impact that it had on how she has navigated life and on the message that she wants to share with the world was so powerful. And I felt so much gratitude for the fact that she was willing to allow
Starting point is 01:25:32 me to tell that story. It was a beautiful example too of when you share things with the world, you sort of cast out these like magnets. And every piece I've ever written, anything that I've ever shared, is this tiny little magnet that is sitting out in the world working for you without you knowing it. She responded to a piece that I had written 12 months before. It wasn't like some new thing that I had sent out.
Starting point is 01:25:59 She happened to send it back to me, right at this point when I was about to turn in this book. And I think the book is made significantly better for the fact that that happened. It was like you expand your luck surface area by sharing things, by putting these things out. The chance event, the lucky event of her seeing and responding, it was lucky.
Starting point is 01:26:17 But at the same time, I sort of engineered that luck. For sure. I wanna talk a little bit more about time. You were talking about like Kronos and Kairos, the difference between the linear progression of time and time more as a function of like energy and attention and intentionality. And it was really interesting the way that you kind of,
Starting point is 01:26:39 you presaged this whole idea by talking about the history of humanity's relationship with time, which is one that went from worship, I wrote it down from worship to measurement to understanding to control. And this notion that we have now today, like more time and this advanced ability to make productive use of it.
Starting point is 01:27:04 And yet the control that we desire remains elusive. And of course, we're surrounded by more distractions and more kind of addictive things that are like vying for that attention that makes it more difficult, of course. But among all of the kind of pillars, this is the one that I struggle with the most. I love this idea of time as wealth,
Starting point is 01:27:30 but nature abhors a vacuum and distraction is always a convenient sort of way to fill the vacuum of those in-between moments in your life. And it's something that kind of eats away at your soul if you're not really intentional about carving out and protecting and creating boundaries around your time so that you can not just deploy your attention where you want it to go,
Starting point is 01:27:58 but also to enjoy the experience of your own life while you're living it. There's this scene in Lewis Carroll's Through the Looking Glass where Alice and the Red Queen are running together and they keep running faster and faster. And Alice has this realization that although they're running faster and faster, they're not actually moving. They're not actually passing anything. And the Red Queen says, oh, you actually have to run twice as fast in order to get anywhere.
Starting point is 01:28:27 We are really living in that reality in many ways. We're living in this world where you are having to run faster and faster just to stay in the same place. And I think many people feel that way. It's called the Red Queen effect. It's the idea that you actually do have to run faster than your environment in order to make progress. It's from evolutionary biologies.
Starting point is 01:28:45 Like you have to actually evolve faster than your competitors, your surroundings in order to survive. And the challenge is people spend their time and invest their time into what I would call and what I do call low leverage activities. You spend your time on things that actually aren't progressing you in the direction of your goals,
Starting point is 01:29:07 in the direction of the things that are going to move the needle. And I think the best example of someone who does the opposite that we can learn from is Lionel Messi and the way he plays soccer. If you go and actually Google search, Lionel Messi walking, you'll get a half a million hits. He has probably the most talked about walking habit
Starting point is 01:29:24 in the world. Before the World Cup, there was all of these articles about how you were gonna see him just like lazing around the field. And even in the like, in the World Cup final, right before they won and before that goal that tied the game, he's like walking, he's literally walking around the field.
Starting point is 01:29:39 If you go and watch the replay and kind of just like looking around, staring off into space, it looks like a scene from before the game started or after it ended. And it's actually the most important match of his life in the like hundred seventh minute. It's strategy, not laziness. He's conserving all of his energy to deploy it into the one moment that
Starting point is 01:29:59 really counts into the one action that he knows is going to drive the highest leverage and going to create the outcome that he wants. It's the exact same thing as Warren Buffett and the way that he knows is going to drive the highest leverage and going to create the outcome that he wants. It's the exact same thing as Warren Buffett and the way that he makes investment decisions. He focuses all of his energy on the things where he can actually make a difference and says no to everything else.
Starting point is 01:30:16 The challenge is that most of us view no as something that we don't understand. It's like a foreign language to us saying no to things. We say yes, we default to yes. Every commitment, every new thing we're asked to do, every email, every cell phone notification, and everything that comes in is a stimulus and we immediately owe it a response.
Starting point is 01:30:36 There's this fake urgency that we create. And I think Cal Newport has done the best job of shifting the paradigm around this. Slow productivity is his new book is fantastic. To just say, and deep work as well, to just say that the tried and true way to create extraordinary outcomes is not by doing more. It is actually by doing less, but better.
Starting point is 01:30:59 Essentialism at its finest. Isaac Newton and his miracle year. It's like locked in a room for one year, focusing all his attention in one spot and one point in time creates a lifetime worth of outputs. That might not happen if not for the epidemic that they were facing, the plague ravaging Europe. But that concept and then spending the time
Starting point is 01:31:24 actually thinking about what are those activities in your life? What are those two or three things that are really going to progress you forward so that you can shift your time and energy to be focused on those makes a big difference. What's the relationship with discipline in that equation though?
Starting point is 01:31:39 Because it's one thing to say, look, you've got to put this down and you got to, this is where your attention needs to go. If you want to move forward on this thing that you're claiming you care about, right? In practice, we're human beings, we're flawed. You know, we like shiny objects and red wagons and things like that.
Starting point is 01:31:56 And it's very easy to like throw us off track. And so, yes, you need discipline. You need accountability to your point earlier. What are the drivers of like putting that into practice for somebody who actually struggles with this? Yeah, I struggle with this by the way. I have very low attention span. The biggest thing that has changed the game for me
Starting point is 01:32:16 has just been adding a real structure around time boxing my day. What I mean by that is just having windows of time during the course of the day that don't need to be super long, I do an hour, that is going to be focused on a specific thing. And what you can make sure when you do that is that you have enough blocks during the day that are really hyper focused on those couple of things that matter.
Starting point is 01:32:40 And the other thing that you benefit from there is you leverage Parkinson's law, this idea that work expands to fill the time allotted for its completion. Email is the biggest example of that. It's very easy to email throughout the entire course of the day if you just graze on it. You end up grazing on these low value tasks. By time blocking things out,
Starting point is 01:32:59 you give yourself one window or two windows during the day. When you're going to email, when you're going to respond to texts or notifications, you condense all of that activity. You end up actually doing it more efficiently and better. You send better responses because you're focused, but also you don't allow it to bleed into the time that should be deployed into those things that matter.
Starting point is 01:33:18 What is the thing that you struggle with the most with this? Is it the phone? Is it saying yes, the cool stuff that you get invited to go do? Is it the phone? Is it saying yes to cool stuff that you get invited to go do? I don't have a problem with saying yes because I've fundamentally given up on being liked by everyone. I spent 30 years of my life wanting to be liked.
Starting point is 01:33:36 And what I realized is that people will like you when you say yes to everything, when you avoid hard conversations, when you let things slide, when you never create boundaries and real ones actually love you when you do the opposite of those things. So I've given up on being liked
Starting point is 01:33:52 and just focus on my real friends, the people that I really care about. The one that I really struggle with is compartmentalizing that barrier between work and family. I really struggle with turning off to make sure that when I'm with my son or with my wife, I'm really with them. Cause you work at home, right?
Starting point is 01:34:13 So you're around it all the time. And that becomes, yeah, it's difficult to have those hard outs on that kind of stuff so that you can attention shift. And your kids pick up on it. If you have your phone in between you, I mean, my new rule is that I don't wanna have my phone between me and my son.
Starting point is 01:34:30 And if I'm gonna do something, it needs to be in another room because I realized I was just having too many moments where he was trying to play with me or say something and I was doing something right here. And what I realized is that time and energy are not the same thing. So like, yes, I was with him in that moment
Starting point is 01:34:44 from a time perspective, but my energy was somewhere else. And kids and people in general pick up on energy, not time. You can spend an hour with your spouse, but if you're on your phone or you're doing email the whole time, that was not an hour of value that you got out of that. Versus 10 minutes where you were truly disappearing because you were listening to them
Starting point is 01:35:05 can be extremely powerful. Yeah. What is your rubric for making decisions about where you invest your time and what kind of boundaries you create to separate work from the other parts of your life beyond like I'm the guy who's gonna coach my kids' sports teams.
Starting point is 01:35:24 Like that's fine as a kind of macro, kind of global rule, but in the day to day of like, should I do this? Should I do that? I need to call this person back, but this thing is happening. Like the kind of brass tacks of just daily life that all of us have to kind of navigate.
Starting point is 01:35:42 Yeah, I have one given up on the idea of urgency. Very few things in life actually need to be replied to right now. I used to be someone that prided myself on like responding to every text right away or responding to every email that same day. You know, I swerved off the road one time trying to respond to an email from a partner like on my computer while I was driving,
Starting point is 01:36:07 like crazy shit that we do to try to like feed that urgency monster. And I've completely given up on that. I've just recognized frankly that like, there's nothing in life that's truly that urgent. And if you know what your two or three things are that really matter, maybe one of those is my relationship with my wife and son, maybe one of those is like
Starting point is 01:36:27 this book project and maybe there's one other thing, those things can get my attention, I'll reply to them very quickly and the rest of the stuff, maybe it's gonna take a week. But really just giving yourself that grace to recognize that like, I don't need to be stressed if I don't reply to someone's text right away. The unfortunate thing is that
Starting point is 01:36:44 sometimes that leads to people not liking you I don't need to be stressed if I don't reply to someone's text right away. The unfortunate thing is that sometimes that leads to people not liking you, or it leads to people feeling like you're no longer as close as you once were. And that is just a reality of life that you are going to lose friends when you kind of change the way that you're living along these journeys.
Starting point is 01:37:02 The other just like simple rule that I have now is one that I use to fight my natural optimism around new opportunities. I don't know if you do this too, but like whenever a new opportunity comes my way, I have a tendency to be like, this is the most exciting opportunity in the world. And to fight back against that,
Starting point is 01:37:18 I always ask myself, if this is gonna take twice as long and be half as profitable as I currently think, would I still do it? And if the answer is yes, then it might be something that I'm gonna lean into. But normally that like initial new opportunity optimism, you get proven wrong because things do just take way longer.
Starting point is 01:37:37 Like a book project, I thought I was gonna write this book in a year, I'm sitting here three years later and we're just having it come out. You need to fight back against that optimism. We never have more time later. So like the, it's called the yes damn effect. It's this idea that like we say yes.
Starting point is 01:37:54 Yeah, yeah, yeah. This is like a major malfunction of mine. Like if it's far enough off in the horizon, like I'll say yes to like anything, right? And you have that rule around like, would you do it if you had to do it today and would you do it like today, even if it, what is it like it's twice as hard?
Starting point is 01:38:11 Yeah, it's gonna be twice as long and half as profitable. You think it's going to, yeah. That's a really good kind of like. We always think we're gonna have more time in the future and you inevitably will not. You will get there and be like, ah, shit, why did I say yes to this thing? I shouldn't have.
Starting point is 01:38:25 And we've done that over and over again. So it should be an easy rule for people to follow because you felt that in your life. Back to this transition that you made during the pandemic. So the pandemic happens, you're at home, you're navel gazing or like, you know, you know, having a moment about like how you're living your life.
Starting point is 01:38:43 How did you actually make that transition of getting out of finance when you have a family and you have expenses and all of that, I'm sure you had money put away or whatnot, but going from that and stepping into this kind of unforeseen relationship with risk to do something different where maybe it wasn't even clear what that actually looked like.
Starting point is 01:39:10 I had taken a lot of tiny actions over the year before that in hindsight, I can connect the dots and say that I was kind of setting myself up. In the moment, I was just following my energy and that was in the form of writing. I had started writing on Twitter, I guess what's called X now in May of 2020. And from then until the time when I made the big transition, May of 2021, I had grown my platform from being, I don't know, roughly 500 followers when I started
Starting point is 01:39:38 to 150 or so thousand followers. And on the back of that, there had been some seeds of business that had started to pop up. A lot of founders, either friends or people that I had invested in, were coming to me asking like, how do I grow a platform? It's valuable for fundraising or employees
Starting point is 01:39:57 or whatever it is. And so I'd started doing a little bit of, just on the side talking to people, helping. And in the moment where I had to make the transition, the fact that I had taken all of those actions for a year was really empowering. People call these things like a leap of faith, right? You're taking this big leap of faith to make a change.
Starting point is 01:40:16 And the reason a leap of faith is so scary is because you have a fundamental asymmetry of information and evidence, meaning I know a whole lot about my life where I am right now. I know that I can live the life. I have all the information and I have all the evidence to suggest I can live here.
Starting point is 01:40:34 The other side of that leap, I have no information and I have no evidence that I can build a life there. So it feels like this like hundred foot leap with this enormous chasm down below. You can shrink that a whole lot by gathering information and by creating tiny little bits of evidence. Because every single ounce of information evidence you create shrinks it. It makes it feel like a more manageable step.
Starting point is 01:40:57 So when I actually had to functionally do that, I was scared because I had never been an entrepreneur. I had never frankly even thought that I could be one. And when I said we need to move, my initial thought was I'm gonna go join another investment firm. And I said that to my wife. I said like, I think I'll just, you know,
Starting point is 01:41:14 I'll interview, I should be able to get a job on the East Coast. And she said to me, can't you just do this thing you've been doing on the weekends, like full time? This like, you're writing writing the things you're doing, like, can't you just do that? I had literally never thought about it.
Starting point is 01:41:28 The idea of being an entrepreneur, doing my own thing, never crossed my mind. And it was only through her belief in me and through her questioning that foundational assumption that I had had about what was next, that I was led to like, oh, I can actually remake my entire life. It's not just a geographic change.
Starting point is 01:41:45 It's a geographic change, a career path change. I mean, it's gonna be my entire life that I'm gonna go and make a shift around. Yeah. The sort of behind the scenes kind of thing at play here, though, is when you describe like the asymmetry and all of that, it's like, I'm looking at you and I'm like, this guy's such a quant, you know what I mean?
Starting point is 01:42:06 He's like trying to like, he's trying to like write the code for this whole thing. And in truth, what really moved the lever was your wife, who has this heart centered perspective and isn't thinking in terms of risk analysis and asymmetry. She's just like, that doesn't light you up. This does like the emotional kind of like spiritual piece here, which is, yes, I have all this evidence
Starting point is 01:42:37 about what my life is like right now. And that keeps me stuck, but I also know how it makes me feel. And I know the extent to which is, you know, kind of degrading my soul. And this other thing that is Kairos oriented, that's like giving me life force and energy. Yeah, there's not a lot of evidence,
Starting point is 01:42:59 but your wife sees what you couldn't, which is that's all the evidence that you need in order to kind of motivate that leap into something that is unknown. I have never until this moment had that articulated to me or understood that as well as I do now. We had known each other since she was 14, I was 15 years old.
Starting point is 01:43:23 And so in thinking about that even, what you recognize is she probably knew me and could see me better than I could see myself. And the reality underlying all of that and the energy underlying all of that and the heart that was not exposed in the work that I was doing prior, she could see that. There was nothing wrong with the work I was doing.
Starting point is 01:43:44 And I loved the people I worked with and it just wasn't for me. The energy, the life force, as you said it, wasn't there. And sometimes in life, all it takes is one person believing in you, understanding you in those moments when you can't see yourself. And if you have that, if you have one person in your life like that can't see yourself. And if you have that, if you have one person in your life like that, you're lucky.
Starting point is 01:44:08 And for her to say, I'll go on this ride with you, even though, yeah, it might be uncertain. Yeah. It will be uncertain. It will be uncertain. Yeah, yeah, yeah. Like you were like this crazy Twitter superstar. Like you have like a million followers there, right?
Starting point is 01:44:23 And I think you were sort of first well-known because you were one of the first people to like do threads before like threads were a thing. And that got like a bunch of attention and traction, but you've really built this powerful community around these ideas that you share, which clearly you think a lot about and write extensively now and now in this book
Starting point is 01:44:44 and in your newsletter, but that was sort of the backbone upon which you kind of created this architecture for everything that you're doing now, right? It all began on Twitter. All began on Twitter. If you create value, you receive value in return. I feel like this is something that gets lost
Starting point is 01:45:01 in all of the career advice that you see out there. It's like, everyone wants to give career advice and no one wants to say that like these basics actually still hold true. Create value for people. You'll do great in your life and in your career if you create value for everyone you're around. I mean, that's a long-term strategy, right?
Starting point is 01:45:18 So I'm curious around how you immunize yourself from the incentives of audience growth that seem to capture a lot of people and then begin to drive them into directions that are contrary to their kind of value set. You say long-term games. I think that everyone likes to say they're playing long-term games
Starting point is 01:45:40 until they actually have to do long-term stuff. It's like there was a meme going around a while back that said that like, everyone likes to wear Carhartt but no one likes to do Carhartt shit. You know, no one wants to actually do that. The way that I've always thought about this. Cosplay. Yeah.
Starting point is 01:46:01 The way that I've always thought about this with having a platform is that in the path I was on, there was a track, right? You knew that, like from lawyer days, there's a track. There's a 30, 40 year career track from joining as an analyst to becoming a partner and riding off into the sunset, retiring, you get your gold watch and you're kind of done. There was no path in the world that we operate in. No one is setting up a track for you. There's no retirement plan. There's no like, okay, here's what I'm gonna do
Starting point is 01:46:28 in years zero to 10, and then here's where I'm gonna be years 10 to 20. That doesn't exist. And that's really disconcerting. And so when I went into it, the first thing I asked myself was what is the thing that makes this a 20 or 30 year journey that I'm on? What is that? To me, that is trust. Trust is the thing that makes this a 20 or 30 year journey that I'm on, what is that?
Starting point is 01:46:45 To me, that is trust. Trust is the atomic variable. It's not likes, views, follower growth, it's not any of those things, it's trust. You need some group of people to deeply trust you. The only way that you can build trust is through real raw authenticity. It's not through growth hacks.
Starting point is 01:47:06 It's not through whatever the latest, greatest trend is or whatever that fancy thing is that people want to do and jump on. It's through building real authentic connection with people. And that extends to one-to-one connection. Maybe it's one to many, but whatever it is, it's trust that has to be the focus. You can build a whole lot of commerce on top of trust. That's what, you know, go back 50 years, P and G, Johnson and Johnson, they owned trust
Starting point is 01:47:31 because they owned all the airwaves. They owned radio, TV, magazines, all of those things. So they built commerce on top of it. Now we're in a world where the trust is decentralized rapidly. And you can build a node of trust for yourself, but it has to be that you are focusing on trust, not on those other things.
Starting point is 01:47:48 And so on my whole journey, you can go back and look at anything I've ever done. I was never following some trend. I've never like jumped on the, hey, let me do a thread on Ted talks. That'll change your life or like Chrome extension. I just never done it because I don't care to grow a bunch of followers
Starting point is 01:48:05 that don't know who I am. I want people to know who the values that I am all about, to know about my family, to know about the journey that I've been on. And there are gonna be people that don't like that and don't wanna follow me and that's fine. If I'm not for you, that's great. You should find people that lift you up
Starting point is 01:48:20 that you feel energized by. That shift in focus has been, at least in my own mind, what has allowed me to avoid the perils of audience capture as some people have called it. Yeah, trust is the most valuable asset. And it's also the thing that, you know, most people who are creating and sharing on social media
Starting point is 01:48:42 have the loosest sort of relationship with. It's also the easiest thing that can be destroyed, right? And so I think for that reason, it's the thing that's most important to like preserve and protect. Yeah, it's like Warren Buffett has that quote about, it takes like 20 years to build a reputation and just 10 minutes to destroy it.
Starting point is 01:49:02 Right. It's the same thing. I mean, you're a perfect example of this and you've seen this now because you've been around and doing this for so long. The number of people that have come and gone during the time that you've been creating and doing this, it's hundreds, hundreds of big people that were like really well known and that were crushing it
Starting point is 01:49:19 and that everyone thought was gonna be the next big thing. But it's hard if you're chasing trends and if you're losing, honestly, it all connects because I felt like for so many years of my life, I was just playing a role and fulfilling someone else's definition of what my life should look like. I didn't wanna do that again. That's exhausting.
Starting point is 01:49:40 You might be able to do that for a year, three years, maybe five years, but eventually you are going to get tired of putting on an act, putting on a show. And so if you were going to share genuinely and authentically about your life, it has to be real. It has to be the journey you're on. And the benefit of that is you can do that forever.
Starting point is 01:49:56 I never run out of content because the content is how I'm living my life. It's what I'm doing. It's the people I'm talking to. So when you interface with social media, as somebody who is kind of creating in that ecosystem consistently, like it's a shifting landscape also.
Starting point is 01:50:15 And most of the kind of discourse is around like what's working and what's not, to your point of me being around for a minute, like, yeah, like I just, I do my thing, dude. You know, I'm a tortoise. I just show up every week. You know what I mean? And I have seen a lot of people come and go.
Starting point is 01:50:31 Sometimes that's because of a reputational issue, but often it's because people are caught up in, you know, the kind of short-term gains and they haven't created something that has real value, let alone a kind of workflow that is sustainable for the long haul. So I'm always thinking about the other kind of types of wealth because, you know, if my marriage falls apart or I'm not there for my kids, or I don't have time
Starting point is 01:51:00 for my friends or my fitness or the other things that nourish my life, then there's no way that I'm gonna be able to continue to show up for this, which is something I've been doing for like 12 years now. And I still love it, but I love it because I have to pay attention because I have dimmer switches in these other areas of life.
Starting point is 01:51:19 Like I think there's this binary idea on this on-off switch sort of thing about how you have to be and how you have to live in order to, you know, do something great. You know, you have to go all in and you gotta block out the world. And maybe, yeah, maybe there is a brief season of life in which that is important,
Starting point is 01:51:42 but you have to create counterbalances for that, like in the way a pendulum has to swing, like it's either it's a dimmer switch or a pendulum, like it has to swing back into balance. So we think of it as these on-off switches, you go all in, or there's this other pressure that your life has to be perfectly balanced every single day, right?
Starting point is 01:52:00 Like all five of these types of wealth have to be boxes checked before your head hits the pillow every night. And I think that that creates a pressure that people can't really sustain or live up to. Yeah, it's balanced in the micro versus the macro, right? Like it doesn't necessarily- What is your timeframe, right? Like, yeah, like my life is not balanced on a day to day
Starting point is 01:52:23 or even week to week basis, but on a yearly basis. Absolutely. And you know yourself well enough to create that in your life, right? Like I know right now I am in a season of unbalance during this window while I'm gonna be trying to push this book out into the world. And I'm trying to impact millions of people.
Starting point is 01:52:41 And this is a big part of what I wanna be able to tell my son that I do and the impact that I'm creating in the world. And that means that I'm away, right? I'm away right now. I'm away next week. I'm away the week after that. And that's tough. That's not balance in the micro, but it is in the macro
Starting point is 01:52:58 because I know what it's going to imply. And I know that I'm going to be able to reset and make sure that you do have the week when you're just there, when you're present. Putting too much pressure on yourself to be perfect in the days is kind of a waste of energy. Right? Like you want to be perfect in the years. You want to be perfect when you zoom out because the days look like this.
Starting point is 01:53:19 And what really matters is the trend line. People obsess over their current location and not enough on like, okay, but what is the trend line. People obsess over their current location and not enough on like, okay, but what is the trend line of where you are? You're going to sit in your current spot and look around at all the people around you and say like, well, I'm not doing great because I'm 30 and I haven't, I didn't hit Forbes 30 under 30. So I'm not doing great. Well, if your trend line is going like this, and you're in this spot, that's pretty damn good versus the person that like is way above you but their trend line is flat. You're going to pass them.
Starting point is 01:53:46 You're going to continue to do better and better. And so shifting that narrative in your own head away from like the comparison of where do I sit relative to everyone else, worrying about how everyone else's grass looks rather than focusing on watering yours. You reference Arthur Brooks a couple of times in the book and specifically you kind of quote this thing
Starting point is 01:54:08 that he always says when people ask him like, what are the drivers of happiness? And he says, friends, family and a relationship with the divine, right? Arthur is a deeply religious person. His faith is very important to him, but his evidence-based work also supports the idea that faith is kind of a crucial element in happiness.
Starting point is 01:54:35 So I'm curious around like what that looks like or means to you. I mean, it's not one of the pillars in your book. So how would you kind of couch yourself in that context? I am a very spiritual person. I am not a religious person necessarily in terms of one particular faith, but I grew up in a household that had everything.
Starting point is 01:55:03 I mean, my mom grew up Hindu, my dad grew up in a Jewish household. We have a number of Muslim family members. My mom has a lot of Buddhist tendencies. I mean, we grew up with everything and I am deeply connected to a variety of different cultures as a result. And I feel very lucky for that.
Starting point is 01:55:19 And you know, it's sort of in my like, mutt background, my mixed background to be connected to all these different types of people. My view on spirituality is that it runs the gamut across of several of these types of wealth. I talk about the idea of space in mental wealth. So idea that you need to create space in your life. Victor Frankl talks about our power being in the space
Starting point is 01:55:40 that we can create between stimulus and response. So much of our life is like this immediate response to every stimulus. And spirituality is probably the primary way that most people do create that space. It's through connecting with God, through your higher power, it's through prayer, it's through meditation practice, it's through walking.
Starting point is 01:55:59 Any way that you can create that space in your life creates mental wealth. The other thing and why I think personally that faith is such a key connection point for happiness is because of the feeling of community. It's the feeling of connection to something bigger than yourself. And we've seen that time and time again,
Starting point is 01:56:19 that acting in the service of others, acting in the service of something bigger than just you is probably the most tried and true pathway to being happy. It's one of the steps in the 12 steps. Service, community, unity. Yeah, I mean, your life expands in lockstep with your commitment to serve others. And the premise behind service to others is this humbling notion.
Starting point is 01:56:48 It's like a dose of humility that you're not the center of the universe and it's a cure for your self obsession that there are more important things at play. And so to practice service is to humble yourself to that notion and that can take the form of some faith doctrine, but just being available to other people, I think is sort of a religious act in and of itself without a doctrine.
Starting point is 01:57:16 Yeah, I've also just found interestingly that when I focus on money, I make dumb decisions and I do dumb things. When I focus on service, I focus on creating value, when I focus on ripples, I actually make more money too. And I'm happier. You also create time. It's that inconvenient thing that you think
Starting point is 01:57:40 is occupying time you really need for something else. But when you practice it, suddenly all those other things end up getting done and they get done in a more neatly packaged way than they would have otherwise in my experience. That idea of creating time is a really good one. And one that I often reflect on because people will say like, oh, you can't create time. You have your window and you never know when it's going to be up and
Starting point is 01:58:08 one day you're going to wake up and you're going to die. And it couldn't be further from the truth, right? Like at the very beginning of this, we had the conversation about I had 15 more times that I was going to see my parents. We took an action. We moved back across the country. That number 15 is now in the hundreds. I see my parents every other week. They get to spend tons of time with my grandson and experience all the joys and the love that comes with that.
Starting point is 01:58:34 I mean, we literally created time. We created moments with the people that we care about by taking an action, by doing something. We bent, I have these graphs in the book that show how much time you have with different people. We bent the curve by taking an action. And again, it goes back to that idea. Like you have to know that you have the power
Starting point is 01:58:52 to actually change things in your life. You're not a victim that just has to, you know, kind of give in to these twists of fate that come your way. You can actually take actions and change how time operates. So what is your message to the person who says to you, well, this is all great, but like, look at you and you went here and you had this and you don't understand how complicated my life is.
Starting point is 01:59:17 And, you know, I don't have the agency that you have and it must be nice. Or, you know, I just can't get my head around how I could actually make those decisions and do it in a way that wouldn't be irresponsible because of the way my life is set up. Yeah, I mean, the first thing is it doesn't have to be dramatic.
Starting point is 01:59:38 Dramatic change is what captures attention, but as we've talked about, the tiny changes are the ones that actually create outcomes. And you are always in control of taking a few tiny actions that will lead you to be slightly better off tomorrow. There's this, the last scene in the movie, The Martian, which is one of my favorite movies, Matt Damon is talking about how he survived his time
Starting point is 02:00:00 on Mars and he just says, you just solve one problem and then you solve the next one and then you solve the next one and then you solve the next one. And if you solve enough problems, you get to come home. I love that phrase because it really is true. When we're in a bad spot or when you have some huge problem in your life, it's just this enormous wall in front of you.
Starting point is 02:00:18 And that is the reason people don't act. It's this huge wall. You can't imagine going and scaling this big wall. But all you really have to focus on is just the one little step. It's just solving the one problem. And so for anyone out there that feels that way, it's just that. It's take the one tiny action today. It's like wake up early and do the workout. Text the friend. Like if you feel like you don't have a relationship with someone that you should, send them a text, give them a call. If you feel like your body is not where it should be, do the one workout.
Starting point is 02:00:47 If you feel like your time is not in the place where it should be, audit your calendar. Look at where your energy is going during the course of the day. Do the one tiny thing that is gonna leave you slightly better off tomorrow. And what is the core idea beyond that that you want people to take away from the book? Your wealthy life will involve money, but in the end, it is going to be defined by everything else. Recognizing that today and then taking actions to actually drive yourself in the direction of that is the most important thing.
Starting point is 02:01:29 I wish I read this book 25, 30 years ago. Well, you read it now. Yeah, yeah, yeah. Amazing, man, thank you. Like I said, at the outset, the book is really quite an accomplishment and it's incredibly thorough. Like it's not a short book.
Starting point is 02:01:45 It's easy to read, but there's a lot in there. There's a lot. And I think it's, you know, I said, I wish I had read it when I was younger, but I think there's something in there for every single person at whatever stage of life that you find yourself in, whether you're an empty nester or a kid who's, you know, looking at graduating from school and trying to figure
Starting point is 02:02:06 out what's next. So thanks for writing it and thanks for coming and sharing with me today. Thank you so much for letting me share. That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guests, including links and resources related to everything discussed today, visit the episode page at richroll.com where you can find the entire podcast archive, my books, Finding Ultra, Boising Change and the Plant Power Way,
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