396. The Illusion of Success, Mindset of Consistency + Discipline & Building a Long Lasting Business Model with Sahil Bloom
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Welcome to the podcast. Thank you so much for having me. I'm thrilled to finally be able to make it happen in person. Finally, I know. Same. How is it having a two-year-old? Oh, gosh. Oh, we're going to dive straight into it on the heavy stuff. Yeah, I know. So our kids are basically the same age, right? What's your birthday? Yeah, May 23rd. Okay, so May 16th. So we're literally both right in the mix. Two-year-old is absolutely insane. And I have a boy. I know you have a girl. And the...

I think you get paid back for whatever you gave your parents. And people say that. And I think it's the reality for us now because I was apparently a crazy child and gave my parents tons of grief. And now I just see that in my son. And it's terrifying in the most fun way. He's a complete madman, but he's having so much fun. And it's intoxicating to see your child...

sort of learn about the world. And there's literally nothing better in the world than seeing your kid smile. And so like the fun that he has exploring and being curious and seeing the world around him and falling and hurting himself and all those things. I just, I mean, I can't imagine life without it now. - I know it's crazy 'cause I didn't think I would love it this much.

And then it just feels like every week it gets better and better. Were you a kid person? Like, were you someone that always wanted? Okay. I always wanted kids, but I wasn't a kid person. Like my idea of hell on a weekend was being invited to a kid's birthday party. Whereas now I live for that shit. I'm like, oh my God, I can't wait. That's still my definition of hell. The, uh, I'm bad with like, um,

I feel like in most of our 20s, I wasn't sure that I wanted to have kids. And it was in hindsight just like I was selfish and I was just like happy traveling. I mean, you're so carefree. And now looking back on it, I'm like,

What did we do with all of our free time? All of this time that just existed, I don't know what we possibly did with it. We had the freedom to just go on dates every night, but we somehow didn't. We had the freedom to travel every weekend. We somehow didn't. It's just funny to think back on what you almost can't imagine what your life was like before it and the changes around it, but I wouldn't have it any other way now.

- I know, I was, me and Steven were driving back from somewhere the other day and Noemi wasn't in the car with us. And I said to him, can you remember, what did we do on weekends before we had her? And the two of us couldn't remember. We're like, did we just like waste all this time or work? Like you can't even remember, it's crazy. - And like, what did you talk about? - Yeah. - It was like so much conversation now as a parent.

revolves around like funny things your kids do and not in a bad way, not in like a boring way. It's just your kid provides so much both entertainment, fear, stress, anxiety, like on a daily basis. There's a hundred things that they did that are like funny to talk about, crazy to talk about, scary. And so it's like, it's for us at least, it's been a really incredible thing in our relationship because I do feel like

it's just created so much appreciation, connection, closeness, gratitude on a daily basis. And part of that is...

We both just feel so grateful for having a son that's healthy, that is having fun, that we're able to be around, that his grandparents are able to be close by. And we weren't always sure we were going to be able to do that. And so there's a lot of gratitude that just comes from that. Yeah, it makes you appreciate all the simple things so much more than before. I mean, when you see, I don't know if your daughter does this, but like my son, when he sees like little things, he does this thing where he goes, what?

And it's true childlike wonder with the most random thing. He'll open a little storm gutter drain and see that there's a hole with water in it. And it's the most amazing thing in the world. He wants to throw stuff in it and mess around with it.

And you remember that there are a lot of amazing things around you that you just aren't appreciating on a daily basis because now we have responsibilities and we're busy and we're running around to a million things. But if you actually slow yourself down and sort of like take the lesson that you're seeing from your children, there's a lot of beauty that you're missing out on in life.

that you all of a sudden become aware of again. I know. The slowdown piece as well. When I'm playing with her and really just fully focused and it slows me down, I'm like, oh, this is something I need to access more.

I could talk about kids all day. We're not going to do that. I do want to come back later on and talk a little bit about how fatherhood has, if it has changed you. But going back, I want to start with your early career. What did you first get into? What was your career background? So,

So I left. So I played baseball in college. I was at Stanford. I was on a baseball scholarship. And for most of my life, I had identified around being an athlete and playing baseball and probably naively thought that I was going to

play professionally and be some like star athlete like a lot of young boys do. But it took me a little longer to realize that wasn't going to be the case. And so it was probably around my like junior or senior year. I hurt my shoulder, realized it wasn't going to happen. And I had to find my footing in the classroom and figure out what was next. Like what did life look like? And, and,

I always knew I wanted to be quote unquote successful. I just didn't know what that meant. And so I defaulted into the first definition of it that we almost all accept, which is just making a lot of money. And I decided like, okay, let me pursue the path that is going to allow me to make a lot of money. So I went into finance.

And I joined a private equity fund in the Bay Area that was just getting started. That was mostly because it was a fantastic group of people, great opportunity to just be like early on in a fund's life and trajectory, a small group, tight knit, really like a collegial environment. And coming from sports in that background, it felt like a really good fit. And so I spent my first

seven years full-time, basically just marching down that path, like on a partner track to go and become a partner at a private equity fund, which is a very lucrative career track and a very...

a very grindy career track. You work long hours. I mean, you're working 70 to 90, 70 to 100 hour weeks pretty consistently and learning a ton, drinking from a fire hose. But probably after about like three or four years, I knew that

internally, at least, that it wasn't for me. Like it was a path that I had sort of defaulted into rather than one that I had really designed for myself. And it was because of this default definition of success. And so it was a career track that like outside looking in, if you would ask people around me, they would have said I was winning, like I was successful and I was doing great. But internally, I was seeing everything differently.

deteriorating. My health was suffering because I wasn't sleeping enough, I wasn't working out, I wasn't doing the things I needed to do to take care of myself. My relationships were suffering because I was stressed, I wasn't present, I wasn't there for my wife in ways I needed to be, for my friends, for my parents, for my sister. And so I started seeing

all of these other areas of my life were really hurting while it looked like I was really winning or that I was really successful. And that was when I started to realize

I needed to make a change and that there was, um, there were alternative paths out there, but I had to take the leap to actually go and find them and see what they looked like. But I spent, um, I spent seven years walking down the path, have nothing but amazing things to say about the people there, um, learned so much. It set me up financially in terms of like a nice, uh, base and security. Uh, but I fundamentally believe that, uh,

you get one shot at life and not taking the time to think about what your ideal life looks like and like designing the way you want to live is a mistake. That doesn't mean you're always going to be able to actually affect that and live that designed life, but not taking the time to think about it is a big mistake. There's this beautiful letter that Hunter S. Thompson, the author, wrote.

He wrote it to a friend when he was 20 years old, and he talks about the fact that you shouldn't conform your life to a set of goals. You should try to figure out the way of life that you want to have and then design a path to go and achieve that way of life rather than just pick a career track or pick a goal and march towards it. And I really felt that way. I wanted to design...

way of life that felt real, clear, balanced, and conducive to the broader set of values that I had about what success looked like to me. Was there a specific experience you had in those seven years that made you think that way? Or was this just a natural thing that kept coming up for you? I would say that you can tell when someone is truly energized by the thing that they are doing on a daily basis. And I knew pretty quickly that

There were people around me that were deeply energized by investing, by private equity, and that I was not. And you can see it. Like if you, I knew that I could execute consistently, be disciplined. I could work as hard as anyone else. I could do all those things. You weren't going to be able to beat me at those things. But if I wasn't truly immersed and like nerding out on that thing, I was never going to be the best in the world at it or have a chance to be one of the best in the world at it.

When you find the thing that actually energizes you and you're willing to work extremely hard at it consistently, then no one can touch you. I mean, there's absolutely no competing with you at that thing. And so my fundamental belief, like after a few years, was just I need to find the thing that lights me up, the thing that actually gives me that energy, the thing that I feel like I would do whether or not you paid me.

And were you finding glimpses of that thing while you were still working there or did it take you quitting to figure out what that was? No, I started finding it because of COVID. So because of the amount of hours that you're working in a career track like that, you literally don't have the time to explore the range of other things that are out there. So, I mean, I was working 80 to 100 hour weeks by necessity and that's

that's part of how you learn. That's part of how you're growing in those careers, but you don't have time outside of that to explore anything else. It's why when young people come to me for advice, one of my biggest pieces of advice early in your career is to explore, take different jobs, leave a job after a few years, try something else, go and travel, do something entrepreneurial and fail. Um,

Join different clubs, communities, all of those things because what you're doing is you're creating a map of the world of all of these different opportunities that exist so that you can figure out what is giving you energy so that you can go deeper on that in your 30s, 40s, 50s, 60s. You need to find your thing and then you need to dedicate all of your attention and focus to it. But you can't find your thing unless you explore. So it took me having the room to explore to

in order to find that thing. And COVID was that, right? Like COVID all of a sudden hit, we're stuck at home. I have no social life. I'm no longer traveling three or four days a week. I'm not working 80 to a hundred hours a week. Cause I don't have commutes. I don't have quite as much work going on. Like there's just not as much happening. And that was when I started writing and, um,

That became the kind of thing that I was like, oh, this is a craft I really enjoy. I'm starting to see that it can impact people in some way. I can create something sitting at my desk and someone around the world reads it and then is taking an action in their life that might positively impact them. How cool is that? And so I started to feel that feeling of leaning in, that feeling of your eyes lighting up, that feeling of...

you're that first energy when you start something new and you're starting to figure it out. I felt like I was on the starting line of something meaningful. I love this. So tell me a little bit about that journey then during COVID, what you were writing and, and did you start to see traction and how, how did that start to cement itself in your mind as like, wait, this could be something I could do as a job. Yeah. Um, so I started May of 2020, so a few months into COVID, um,

And originally I was writing... It was on Twitter. I had like 500 followers at the time. And I was writing...

basically about business and finance. And that was because that was what I knew well from my job. So I was like, I understand this. And my little like secret sauce is going to be that I'm going to simplify these things for normal people to understand. So rather than trying to be like an expert that talks in fancy terms and jargon and acronyms, I'm going to be the person that like brings it down so that anyone can understand it and engage with it and empower people to take control in that way.

And I was kind of the first person doing that on Twitter and delivering it in a way that was really easily consumable and actionable. And it started immediately to sort of get traction. Like the first thing I put out got shared a bunch.

which gives you the dopamine hit, starts to build the momentum. You start thinking like, oh, this is fun because it's successful and because you enjoyed the process. And so I kept doing it. And basically it was like, I'm just doing this on the weekends. I'm like spending some of my free time writing, researching, creating. And by about like...

like September, October of that year, it had grown to 50 or 75,000 followers. And I started to see people asking me about different business things. And I started to see people asking me for like deeper pieces of content. And so that was when I was like starting to have the wheel spinning on, maybe there are businesses that can be built around this. But I don't know if you recall, like at the time,

The whole creator thing wasn't really yet like no one thought of it as a professional track. There were creators out there for sure and YouTubers and all these different platforms. But there were very few that had done that from Twitter as a base that actually hadn't really started the whole like newsletter boom hadn't started yet.

Um, so I didn't, there was no pattern, if you will, that I could just go follow. There wasn't like, okay, here's the track. I'm going to go plug myself into this track and go build my career this way. Um, it was very much just like the path in front of you is like for one foot is lit up and you just like walk that one foot and then another foot is lit up and you walk a one foot, um, and doing that over and over and over again. Yeah. I, I know. I feel the same way. Like

I really got into this from the other way around because I'd built a business which then started bringing in this community. Whereas when I was looking around for blueprints, I was seeing gamers, they'd been doing this for so long, but I was like, how does that work in my space? So there's a lot of figuring that out.

But was that a really hard decision then when it came to thinking about, do I want to go down this creative path or do I want to stick to this finance career, which is so stable and, you know, a lot of predictability? I don't know during COVID, but how was that conversation and even with you and your wife? Yeah. So there's a quote that I absolutely love. Joseph Campbell said, if the path before you is clear, you're probably on someone else's.

And I remember coming across that and it really resonating at the time that, um,

I don't identify as someone that just follows someone else's path. And I never have. I've always wanted to march to the beat of my own drum. And I've always been a little quirky and weird whether or not I allowed it to show in the world was a different story. But I've always been that way. And so I started to get excited when I saw that there was this different path that I could carve, that I could create, that maybe no one would understand. That was exciting to me.

But it's very different for it to be exciting to you and then to have people around you understand it, like the other stakeholders in your life. And we didn't have kids yet, so there wasn't the enormous weight of responsibilities from that. But we had a house, we had a mortgage, we had bills. We didn't have a super expensive lifestyle, but I had grown accustomed to the fact that I was earning money in finance. And I have an Indian mother who...

you know, there's certain cultural weight to like, she still wanted me to be a doctor probably at that point in my life, you know, or a PhD or an engineer or whatever. And, you know, there are certain, there's certain weight to all of those things. So I never, I mean, I really mean never thought about, oh, I'm actually going to quit my job and make a career out of this. Really until May of 2021, when,

unfortunate set of circumstances around health in our family that brought me and my wife simultaneously to the realization that our parents were not going to be around forever. And if we didn't make a change, we were living in California, 3,000 miles away from them on the East Coast, we weren't going to see them many times in their lives. And

That sparked the reality of like, it's time to rip the bandaid off in life and just take the leap of faith and make an entirely new set of choices. Fortunately, at that point, I had already kind of started experimenting with different business stuff around the new thing I was doing while just as a side hustle alongside. And so I'm a big proponent of that because if you quit your job before you've started the new thing, you operate from a place of fear.

And when you operate from a place of fear, you make short-term decisions. You take every brand deal that comes your way. You take every small little opportunity because you're afraid of not being able to pay the bills, not being able to meet your responsibilities.

Play the opposite side of that. If you aren't operating from a place of fear because you still have your stable job and you're just doing this on the side, you make long-term decisions. You start thinking about what's the real way to build trust with this audience? What are the real durable businesses or communities that I can build around this? And you start doing the things that are the right thing for the 10-year window that maybe aren't going to make you the most money today, but for the next 10 years, next 20 years, they're really thoughtful and lucrative.

So I had done that. So when I actually came to taking the leap of faith, it didn't feel quite as momentous. It didn't feel quite as like leapy. And so when people ask me now today, like when I reflect on this, how can they kind of tactically think about that and that leap of faith that they want to take in life? I view it as it's sort of like an information and an evidence asymmetry. And what I mean by that is

You have a ton of information and evidence about your ability to exist where you currently are. You have all the information in the world on what you currently do, how you can meet your responsibilities, make money, do all those things. You have no information or evidence about the other side, about that life that you want, that thing that you want to do. Your whole job

is to close that gap. It's to gather information and to create evidence that proves to you that you can live on the other side of that. And then what happens is it no longer feels like a 100-foot leap to go and do that thing. It feels like a five-foot little jump or a little step.

because you've gathered information, because you've gone and created little bits of evidence, whether by getting a few clients or making a little bit of money in that new thing, whatever it is, now I don't feel quite as crazy for making that step. And the people around me won't view it as quite as crazy. Yeah.

Yeah, I really resonate with that. So speaking of that leap then going from what you did make that decision from working 70 to 100 hours per week in finance to having this family health situation, which really made you think about a different path and deciding to go in a different direction. How did you not take the self that was working 70 to 100 hour weeks and just put that same self into the business? And did you actually make lifestyle changes and mindset changes to do things differently or

Or was that something you really had to work on? I would say I applied the same mindset that that 70 to 100 hour person had, but to finding the actual life balance that I wanted on the other end. And so I still have that exact same wiring of discipline, consistency, energy, and effort, but it's applied rather than to like sitting at my desk doing Excel spreadsheets the whole time. It's applied to

the broader range of things and values that I want in my life. So it's that same level of discipline that I had around showing up and working really hard might be toward being present with my son or with my wife and making sure that I'm a really present husband and father. It's the same discipline that I try to apply to being a son to my parents and really being present in their lives and being around. And it's the same discipline now I apply to taking care of my body, to the routines that I need around my body or my mind.

And so I didn't lose that. It's still entirely there. And I also just, with full disclosure, I think that a big part of my success as a

And with some of the creative work I've done, it has been because I've applied a level of consistency, rigor and discipline to it that most creative people have a tough time bringing to the work. So I've brought like this finance crazy person mindset to some extent to creative work, which has really helped me because I've just.

I mean, I've written two newsletters a week every single week since 2021. I haven't missed a day. I haven't missed Christmas. There was no Thanksgiving. There was no holidays because that's what my life was like. That's all I know is that level of consistency and discipline. And when you do that and when you care about the quality and you get energy from the work, it's pretty hard to lose at whatever it is you're doing in life.

Was that easy to apply that discipline to the different realms of your life? Or is that something you constantly have to keep in check? Like I know for a lot of people and myself included, I constantly have to work on this. I have that discipline and I have that drive, but oftentimes I have to really consciously pull it away from the work site to say, okay, put this into the other areas of your life that actually matter, that you really care about. But I feel like if just left to my own unconscious desire,

desires, it would be work, work, work. Yeah. We're probably wired the same way. It's very hard. And it requires very, very deliberate thought about the ability to like flip switches in your life. There's this technique that I love that is like you take your phone and you pull out the alarms on your phone and you can actually create and then label alarms for different times of days. And

you can label the alarms for like the mindset that you want to get into at that specific time to give yourself a physical like a real cue that it's time to flip the switch. So for me, I want to make sure that when I'm working in the morning, I'm really working and I'm really locked in on the thing. But then when I come out to have breakfast with my son and my wife, I don't want my phone in front of me. I don't want to be on social media. I don't want to be thinking about that stuff. I want to be able to flip the switch and truly be there and present.

Getting into a habit and like finding those cues that allow you to flip that switch and allow you to create true separation is extremely difficult and extremely important because you don't at some point then you're like.

You're operating at half capacity in both areas if you're not able to flip the switch like that. And so you need, but it's a muscle. It's like a trained muscle and you only build it over long periods of time. I'm still probably not halfway as good as I should be and I'll continue to try to work at it and improve, but it's very, very difficult. Yeah, and I often think too when,

When you can't fully flip the switch and you have these competing desires when you're working and you want to be with your kids or when you're with your kids and you want to be working, I think that's what creates the guilt. Whereas if you can be fully present, and this is my work, if you can be fully present with where you are, I feel like the guilt goes away. I totally agree with that. I also fundamentally believe that one of the greatest gifts you can give your children is living to your fullest potential in whatever you are doing because they see that.

And ultimately, you cannot teach your child anything. They learn by seeing you embody the things in life. So if I want my son to believe in the power of delayed gratification, I need him to see me living by that value on a daily basis. If I want him to be able to embrace doing hard things, I need him to see me doing hard things on a daily basis. Same goes for how I want him to treat my wife. If I want him to treat my wife like a queen, then I better damn well treat my wife like a queen.

So that, I think, is a really important point that we all need to understand is our children are just absorbing. They're sponges to everything they see from us. And so living to your fullest potential in whatever area you determine that to be is a really powerful lesson that you're teaching your children. That's not something to feel guilty about. If you have to work late because you're working hard on something you care about, for your child to understand that and to be able to explain them and bring them into that why is

Then they're starting to learn from that, actually seeing you embody those traits. I love this so much and I believe it. And there's still definitely this part of me that believes it and wants to believe it. But I also feel like, and maybe it's a female thing, I'd be curious to get your perspective on it.

the generation I seen before me, I didn't see a lot of that. I didn't see what it was like to have a super ambitious mom who really crushed her career. I've seen her really crush motherhood.

And so it's a lot of learning and trusting that, oh, this is the right thing. Did you see that growing up or what's led you to believe this? Yeah, I definitely saw it growing up because my mom was both a very present mother and an entrepreneur who built a small business and continues to run that small business to this day.

I also see it in my wife every single day and the way that I feel she pursues motherhood in the way that she was a high-powered designer, rising through the ranks in the corporate world as a fashion designer. And she and I made this group decision that in this season of life, when Roman is young, before he starts school, she really wanted to focus on being a mom. And we live in a culture, and we live in New York, so it's even more of a culture, where

you're told or people say to you the little comments like, "Oh, you're just gonna, are you just gonna be a mom now?" And that hurts when you hear that. And the external perception of her making that decision was the hardest part of making the decision. She was entirely secure and excited and thrilled and felt so much purpose about being a mom and how much power there was going to be and how important that was as a role.

But feeling that stigma almost that was attached to it from other people was something she was concerned about. The idea that there are seasons of your life and that what you prioritize in a given season is up to you, only you can choose.

and that you can prioritize one thing in one season, and then the next season comes, and you can change what you're prioritizing. When Roman is in school and she has more time, she can go back and be a high-powered designer. She can start her own line. She can embrace the creative side. She gets to choose what she's prioritizing. That was an extremely powerful thing to feel and see and just empowering to recognize that

At the end of the day, perceptions aside, it doesn't matter what anyone else thinks about your decisions. You get to choose what you are prioritizing in any season of your life. Made me emotional listening to that because I often interview a lot of women and we are on the other side of it. And so to hear your perspective on that's really, really powerful. And I'm also very curious because I know how devoted you are to fatherhood, to your wife, as well as to yourself and your career.

Do you notice a difference in the way people speak to you and treat you being a father versus the mother? Do you get the comments of who's looking after the baby or do you notice that falls more on your wife? I definitely get the comments. Again, I think there are cultural things that...

depending on where you live and what culture and, you know, if you're affiliated with a religion where there's a standard or a status quo. And if you're deviating from whatever the status quo is in whatever tribe you're a part of, um, people ask you questions, people say things, they make comments and they're not necessarily trying to be rude or insensitive. It's just what they're ingrained in their DNA. And it hurts if, if you're not fully secure and

and really embracing what your decision is in that moment. And no one likes it. It's the exact same thing, by the way, as when I was leaving my job in finance, people would make comments to me like, "Oh, you're just gonna be a Twitter influencer?" Like, "What, you're gonna be an influencer?" And I hated that. I hated hearing that kind of thing.

But I stopped hating it once I was fully like embracing, yeah, I'm going to go impact a million people. Like that's just, it's just a different level. It's a different way of thinking about it. But it was tough. I mean, when, when my wife made the decision around that to, to take a leave from her job and to really focus on being a mother during this season, she,

That was hard. It was really hard for her. And it took a long time and a lot of conversations and a lot of thought to be able to

go to a dinner party and feel super confident in her own skin to say that because her biggest fear was you're sitting at that dinner party and someone says, oh, and what do you do? And she says, I'm a mom. And the person's kind of like, oh, that's nice. And then moves on. That was her biggest fear. And just like being fully transparent. And I totally understand that fear because she's a crazy talented. She's unbelievable at what she does.

And by the way, she's now deploying that insane talent into a whole lot of things as a mother, but also a whole lot of things in my creative ecosystem. She was hugely influential in designing the cover of my book that's going to come out. And so I am super grateful for the fact that she has this incredible talent that is now being deployed in all these different ways. And I also see her and just like the way that she is as a mother now.

I mean, I fall more and more in love with her every single day. And I thought she was an amazing designer. I was so proud of her for everything she was accomplishing. But I have never been more in love with my wife than I am now getting to see her as a mother to our son because nothing makes me happier than knowing that I could be gone and that he would be the best and just have the best life with her. Oh, yeah.

I'm so glad we're having this conversation. I recently heard Elena Cardone talking about this and she made the decision when her kids were young that she wanted to stay at home with her kids and she wanted to have such a loving, stable foundation so that her husband could go and do his thing because that was her desire.

And she said the same thing. She had to step into that place of embracing her decision so that when she was at the dinner parties and she would say, I'm a mother, she could say it really proudly. Yeah, I'm a mother. I'm raising a generation. I'm raising kids that are going to be part of a really fucking powerful generation.

And I just wanna take a minute for that 'cause I know there's a lot of women listening 'cause I know my community and they wrestle with that day in day out. And they listen to these podcasts 'cause their ambition doesn't go away even though they're choosing to stay home or they're choosing to fully embrace their season. And to just hear you talk so beautifully about how much you celebrate your wife's decision there, I think is incredible. So I love that we're having this conversation. - Yeah, I just think the thing of saying just a mom

is, I think, the most absurd and asinine comment that anyone can make. It's mind-blowing. It's mind-blowing. Because it's quite literally the most important job in the entire world. And it's the hardest job in the entire world, too, by the way. I mean, like, the biggest...

swindle was the idea that like, oh, men were going to go work while women just stayed at home. It's like way harder. If I spend a day with my son trying to take care of him, I will pass out at 6 p.m. and sleep until noon the next day because I'm so exhausted how tiring it is. I do not understand how my wife has the energy to be there, be present, be locked in with him, make sure he doesn't kill himself and all the various. I mean, it's unbelievable to me and be loving and do all the things that she does.

And so I just I love seeing more and more people reject that idea of just and embrace all of the power that they have around that and embrace this amazing role. And by the way, also embrace being able to go after your dreams and ambitions professionally and do both. And I just like I think we live in an amazing time where.

You don't have to choose one or the other. You can pursue your fullest potential, whatever you view that as being. And you don't have to feel guilty for any decision that you're making. You can go and create that. And the big thing that I just think is important, no matter which way you're going, is that your children are included in that journey. Because at the end of the day, your children are...

wanting to be loved and supported. And if your child grows up in a loving and supportive environment, that's basically all you can do to set them up for future. Fundamentally, you can do tons of different ways of doing that, sure. But if they grow up in a loving and supportive environment, they know that you have their back, that you're holding them up on your shoulders and that they have a chance to see the world.

That's what we all want. And that's what we're all striving for. There's a million different ways to go and do that, but they need to be included in that journey. They need to understand the journey that you are on and be a part of it, not just be a distant piece. That's sort of a piece of a broader puzzle. Totally. And I think it's all about understanding what's going to make you feel better.

most fulfilled in the season that you're in. And like you say, embracing that decision and going with that decision. And when you are taking care of yourself, i.e. when you are allowing yourself to live up to your fullest potential, that is how you show up for the people that you love.

You cannot take care of other people if you're not taking care of yourself. It's like being on an airplane and the oxygen masks come down and they tell you to put yours on before you help other people. You have to make sure you're taking care of yourself. And that includes your body. It includes mentally. But it also includes feeling like you have a purpose and an identity because that's how you then show up best in the world around you and for the people that you love, including your children. Right.

agree i think self-neglect is is something that unfortunately is celebrated in society and it never ends well never ends well it's fine for like a couple years in your 20s you can kind of pull it off but i um yeah it lasts about a couple days before i need to recharge no i mean resilience in your 30s it's just not quite the same no yeah a couple glasses of wine and i recognize that the next day

So going back to your creator journey and making this decision, what was your business model? Was it my newsletter is going to be the thing that I go in with? Or how? Yeah. Talk me through the business model you decided upon. Yeah. So my business model is pretty different. My entire mindset was...

I'm currently on a track in finance that is like for 30 or 40 years. And if I'm going to make a switch, I want to understand what I'm going to be doing for the next 30 or 40 years. And you cannot...

Sell ads or do brand deals for 30 to 40 years. I just I don't know one has ever done that. So there's not really a case to be made for it. But fundamentally, it's like it's hard to imagine being on that treadmill for that long. And so I knew, OK, that's not going to be the path that might be every now and then there's short term cash flow from that. But fundamentally, the strategy has to be deeper than that.

So I looked to business analogs and because I came from a finance background, I was kind of familiar with business stuff and how these businesses were operating. And the one that I kept coming back to was

Jeff Bezos did with Amazon Web Services. And so for anyone not familiar, Amazon was started as an online bookstore. And as that e-commerce business was growing larger and larger, they needed more and more basically server capacity and compute power to power the e-commerce business. So that had to sit in the background. So they built this enormous cost center that was all of this server capacity.

What they realized after a number of years was there were a lot of companies that would pay to basically rent out that server capacity and that compute power. And a lot of startups needed it. A lot of businesses needed it. But as the internet age was growing, there were tons of people that valued that. So they started renting it out. And what they did was they turned a cost center that was just an enormous amount of spend that they were having to spend into something that was generating cash for the business.

Today, that business, Amazon Web Services, is like an $100 billion business that just exists as part of Amazon. Basically, I tried to pursue that idea of turning cost centers into profit centers around my own business. So anywhere that I was seeing that I was consistently spending money,

I started zooming out and thinking about, is there actually just a business that we can build that I can partner with someone who is an extraordinary operator? And then I can leverage the trust that I'm building and the platform I'm building to drive leads to these businesses. And, and,

And fundamentally, that was an easy thing for me to consider because I had people constantly coming to me asking me, like, who's doing your websites? Who's doing the websites for these things? Or who's doing the back end stuff for your newsletter? Like, who's doing all the operations and the growth? So we should launch a business that helps other people do that.

And so now that has become, like that pursuit has become a holding company effectively. Holding company is just a fancy word. It's just a bunch of businesses that I am either a part or whole owner of that all have operators that are running them. So I'm not running the businesses day to day. I'm effectively in charge of driving business to these businesses.

Today, there's, I think, eight businesses in that portfolio. And they've scaled in different capacities and generate all of them are cash flowing. So they're not I don't consider them to be businesses you would ever sell. I don't think they have a ton of enterprise value. Maybe one of them does, but most of them don't.

but they generate cashflow, they're stable, they're growing, and they all have operators. So I'm not in the weeds having to manage a ton of employees across all of these different things. I love that model because it just allows you to really sit in the creative seat. And you know, if you're doing your job really, really well, these companies will always have leads and they'll always have business. How did you go about finding really good operators? That's probably the hardest part. So my...

I would say maybe one of my only skill sets in life has always been people. And I love people. And it's my creative work benefits from it too, because I just love meeting and talking to new people about human experience and what are they struggling with. But over the years, I have built a network of a lot of people

who I would qualify as extraordinary people that are doing different things that have built really unique skill sets. And my biggest parameter for partnering with anybody is a high bar on integrity because at the end of the day, my face is on anything that I do. And if I'm not going to be running the business day to day, I need to know that the person that is is going to have the same integrity and character bar as I would have if I were running it.

And so I've been pretty deliberate about partnering with people that I know they're willing to sacrifice profit, but not character or integrity. And that has been sort of how I've thought about who to collaborate with. And it,

Sometimes it doesn't work out and the business doesn't go great and we end up, you know, you try it for six months or a year and it's like, no, this isn't going to be big enough. It's probably not worth your time. It's probably not worth my time. And you part ways. But the things that have worked have worked really well and they're really fun and the person is doing a great job and we're helping a lot of people with the businesses. So it's been a cool and interesting model. And

it allows me to continue to focus on the things i'm good at which would be the creative work and avoid the things that i'm terrible at which would be managing a ton of people and you know dealing with operations of these businesses so there's sort of a layer of self-awareness that's embedded into the way that it's structured where i'm just able to spend time on my kind of superpowers and avoid the things that are my kryptonite

How do you structure your time so that you still can check in with the operators, make sure they're unblocked if they're blocked in any way, make sure things are running the way you want them to without getting sucked into the weeds?

I sort of think of like, I'm a big fan of just time blocking. So every day during the week, I think of like mornings as creative. So I work like five to 8am every day. I'm a super early riser. So five to 8am is like my creative block, super focused on whatever the creative project is. And then any afternoon work time is focused on the businesses. And so that's checking in with people that's, you know, helping on any strategic things that's investing all of

anything related to sort of business, miscellaneous things that are going on and creating that separation and time blocking it really helps me in that way. So if there's like a fire going on in one of these companies, do you have it set now that you don't need to jump in and handle a fire? Or if you did, would that be a, this probably isn't going to work out?

Probably that latter. If I'm having to jump in frequently on a business because there are fires, there's something fundamentally wrong with the business. Usually that would mean that the operator wasn't competent enough because they're having to ask me or the ownership structure needs to get changed. I mean, we had one business where I owned too much of the business. And so the operator did not feel empowered economically or mentally, emotionally, because

to run with those challenges. So every time a challenge came up, he would come to me and ask like, oh, how should I handle this? And we actually had to change the ownership structure and give him more so that he actually owned more than 50% of the business because I wanted him to know, you can just go figure, I trust you. I think you're fantastic. You're way more qualified than me to go answer these questions. You're in the weeds more. You understand the questions.

but we needed to flip the ownership structure to make sure that it sort of reflected that so that he felt empowered in that way. That makes sense. And then pivoting to the creative side of your business, and I'm very curious what your philosophy is with your content strategy, what metrics you think are really important and what you think about putting out on a daily, weekly, monthly basis that moves the needle for you. Yeah, I would say I'm less...

I'm less metrics focused than almost any other quote unquote professional creator. I don't look at the performance of posts until 24 hours after, which was a change that I made for my emotional state more than anything else. It really bothered me when I would spend time on something and be really proud of it.

and then it wouldn't perform well. And if I looked after 10 minutes and it wasn't doing well, it would bum me out. Like I would actually feel impacted by that. And that felt silly to me because then you're creating this cycle of not creating things you're proud of because you want, like you're only going to create things that perform well. And that takes the soul out of the work to me. And I think it's the wrong long-term decision.

I think the best decisions are made when you focus on things that are giving you energy that you feel are soul forward. And so I've really tried to make sure that I'm creating content always that I would want to consume and that I

a younger version of me would find valuable and learn from. And so that is kind of like my, I don't know, razor, if you will, for the types of things that I try to create. It's like if I'm speaking to a 25-year-old Sahil who was somewhat lost and not sure of what to do, would he find value in this thing that I'm putting out? And that applies to any platform where I'm putting things out. The way I typically think about content for me is like there's a

a halo thing which is sort of your main thing that you were spending the most time thinking about and putting in for me that's my newsletter it will it is the book but the book hasn't come out yet so it's it's the newsletter and from there I

I can kind of take ideas that I know are resonating with people and refine them and deploy them across different mediums. So the written content sits there. That can then, an idea that resonates can become a shorter form thing that goes out on Twitter. It can become a video that I do in several ways, either short form or long form. It can become something that ends up in the book.

But basically ideas that I know are connecting with people and impacting them positively, I can now deploy in a hundred different ways and impact more and more people and impact the same people more deeply than before. - That makes sense. So if we're talking like hub and spoke

your newsletter is really your hub and then you take off spokes of that to put on different platforms. Yeah, exactly. And what's working for you when it comes to growing the size of your newsletter right now? So newsletter, we have a pretty good flywheel going. I mean, I've always been good about just asking people to share it. So like it's the funniest and simplest growth hack in newsletters is asking people to share leads to 10x as many shares as if you just don't ask.

and it's the same exact newsletter that you're sending out, but I've A-B tested it. Like you send one with a button that says share this and one that doesn't have the button and it's just 10X, like immediately overnight, same exact newsletter going out. And that drives a lot of growth just organically because more people are seeing it. So that helps.

Now we run ad campaigns across Meta and maybe a few other places that you can pay, I don't know, it's probably like a dollar-ish a subscriber is what we're getting. And we know what those subscribers are worth long-term. And hopefully I'm able to convert those people to buy books eventually. And I don't do courses or anything. So there's no monetization in any other way other than we have sponsors on the newsletter. Yeah.

but that is a good growth loop and then there's like recommendation engines now that exist with newsletters that help um but effectively i think about

The newsletter sponsored, there's cash flow coming in from that. How can I reinvest that cash flow to continue to grow it? And we don't run the newsletter at break even, but we don't make a ton of money on it because we're just focused on driving the growth of it for the long term. And if my like North Star, if you will, is impact from a metric standpoint, I want to actually impact people and feel there's meaning in the things I'm putting out.

then the best thing to do is to reach more people with the ideas. Right. So right now you're growing the newsletter, you're kind of above break-even, and then is the hope is that those people will also then trickle into those other businesses that you're running for monetization? I don't really talk about those businesses in the newsletter. I would guess the vast majority of people don't know that I...

have these businesses. I think probably most people don't know how I make money, frankly, just because I don't talk about that stuff often. I do an occasional post on LinkedIn or Twitter, occasionally in my Instagram story, just mentioning them. But the nature of those businesses is they're

the ticket size is so high that you don't need many leads or customers. I mean, like the design business, it's a $15,000 to $25,000 a month thing. And so you can't, I mean, we don't, we would have to build a ton more designers in order to take on 100 more clients. We can't do that. And so you're kind of adding like one or two new customers a month. That's a great outcome, which means you don't have to be talking about it constantly, constantly. So the newsletter, I mean,

My newsletter is big now in the sense that it reaches, I think, like 800000 people twice a week. Sponsors pay anywhere from like nine to ten thousand dollars per cent. And so that gives you a pool of money that you can reinvest into growing it.

And, you know, deploy into ads or deploy into recommendation networks or whatever the things are that are going to grow the business. And so is your monetization strategy very long term? How are you thinking about that? Yeah, my monetization strategy is I want to have the most fun and create the most impact. And I trust that if I can build, if I can create impact,

a ton of ripples in the world, I will get paid on the basis of that in the longterm. And, um, I don't really worry much about short term monetization. You know, I like, I got to sign the book deal. I'll reinvest most of the advance from the book deal into the launch of the book. Um, I just love building for the longterm. So like reinvesting cash into things that I think are going to be really good bets for the future is where my mind goes to. Uh,

I have no use for them. Like, it's not like I don't like money, but I would much rather go and impact way more people and, you know, build for the next 10 years and see how much of an impact we can create in the world than like go pocket that. I don't know what I would do with it. So it seems like a much better use of the money to just kind of continue to try to reach people out there. Yeah, that makes total sense. And then on social, what platforms are you excited about and what's working for you there?

I am having the most fun with video stuff. So, um, I would say that's mainly Instagram and now very nascent YouTube, um, which we started a couple months ago. Uh,

I just love video. I find it to be such an engaging content format. The short form video, there's a really fun flywheel around like I get to have amazing conversations like this. There's 10 moments that come out of every single one of those conversations that get packaged up and then can reach people in different ways. So like most people aren't going to listen to an hour long podcast conversation. A lot of people might listen to a 30 second clip

that hits them really hard and causes them to ask a question to someone else or causes them to make a tiny change in their life. And so now you have a one hour conversation and it turns into 20 million people getting reached by different moments of it in different ways. And that is so fun to me to just nerd out on like, okay, what's the best way to have an idea that I think is really powerful, reach as many people as possible. And it sort of just becomes like

a problem to solve in that way. I love that. And so speaking of like appearing on podcasts and different things, what's your decision-making philosophy right now? Because I'm sure, well, I know when you are a creator and you have a big audience, inbound is intense. And there's always so many requests and

Things directed at you. How do you balance decision-making and what you say? Yes, no to the first layer of it is just people that I really want to chat with selfishly like you and I have known each other for a while We've somehow never met in person and I've been wanting to have a conversation with you I would hang out with you and have a dinner we can just record a conversation and put it out into the world So that's the first layer. I would say my second one today is I

the like demographic that it reaches being one that I really feel I have a message for that is important and, um, and different, uh, you know, not a message that I feel like maybe has been said over and over and over again. And so like I could go on every single, you know, bro motivation podcast and talk about working hard and stuff like that. That's kind of boring at some point. Um, that's kind of been done. There's like

a million guys that do that and go and talk about those things and like they're big and they're jacked and they talk about it and that's their thing and okay that's great but it's much more interesting for me to like talk about the emotional side of becoming a father and you know vulnerable challenges we faced and relationships and that to me is like it's more unique it's more interesting for me to talk about and then the third piece is again like the reproducibility of what you're creating so you

I only do in-person video podcasts. I won't do anything remote anymore because you can't. It's really hard to take a Zoom content and turn it into something great that goes out on Instagram or on any other platform versus an in-person podcast in a beautiful studio or a beautiful space where you can turn it into engaging, immersive content that can now reach way more people. So again, it's like,

It's really just a way of thinking about the leverage on your time. So one hour conversation in person with someone you really care about in a beautiful setting, the leverage on that is enormous because it can go out in so many different forms and formats.

Yeah, I love that you said about leveraging your time because I feel like of the creators slash entrepreneurs that I know, the people that do both successfully, they have to learn how to leverage their time. Otherwise, you get so burned out that you have nothing good to create. And I see that happen constantly, that cycle. So speaking of that, like, how do you how do you manage things like emails and the DMs and the inbound that's constantly coming to you? How do you protect yourself?

your space and time as a creator while also still have a handle on what's going on? - So I'm a huge believer in batch processing. So like Parkinson's law is this idea that time expands to, or sorry, work expands to fill the time allotted for its completion. So you,

Give yourself all day to email, you'll take all day. If you give yourself 30 minutes to do your email, you'll get through your entire email inbox in 30 minutes. So I create just little blocks of time for admin tasks like that. So I just have a window of time every day when I'm emailing. And I know that my email quality actually goes way up because I'm focused on emailing during that window rather than scanning my email inbox all times of the day. And

it blocks it into a short window. So I've done that with email/DM messaging. I've done that with phone calls. I'll only do phone calls during one block of time.

actually now on one day of the week which has really helped and that has been like that has been a great change in my life of just batch processing the things the quality of it goes up it also doesn't bleed out into all the other times of my day so do you do phone calls instead of meetings or how do you do meetings I do anything in person almost like if

if a random person reaches out to me and is like will you do a phone call it's almost always a no if they're like i'm gonna be in new york would you like to meet it's almost always a yes um and that's because i just get energy from in-person conversations and i learn from anyone in the world i don't care if you're successful rich or if you're just getting started you're 22 you're like trying to get my advice i learn from every single one of those conversations and by the way selfishly

those type of conversations lead to the best content because you learn from people what they're struggling with and then you can think about those things and create around it. So I will almost do anything in person. I hate phone calls. I hate Zoom meetings. And I can't, I mean like, it is where my energy goes to die. And so I have to like batch it into a short block and a short window because if I don't,

every day I feel drained from like the random call that pops up. There's this awesome meme that's like, it's like the knife meme. That's like, you know, a random unscheduled like 2.30 p.m. call on a day when you have nothing else. It ruins your whole day. You just like are thinking about it. Then you're like recovering from it. It's just terrible. So I've really tried to be deliberate about it.

I also understand that if you're in a normal job, you can't just do that unless you're maybe the CEO or something. I certainly couldn't have done that when I was in my old career. But you can try to like slowly work towards it and batch things in a way that can actually help you along the way.

Yeah. Oh my God. That meme, every time I see it, it's like, this is me. Yeah. Yeah. There's that, that, and then the one that's like, uh, the, as per my prior email meme, where it's like the guy doing the uppercut and the punches just absolutely kill me. So, so funny. So, uh,

I feel like I have such a good understanding of your business model now too, which by the way, I think is so freaking smart. It's so good. I'm curious. So it sounds like, you know, you have your, let's call it a personal brand and then you have the different companies. What does your team look like within your personal brand to keep things running the way that it does? So primary team today is a chief of staff who has been the best thing that's ever happened to me. He

he and i met originally through twitter as as one does in this day and age uh became close we had worked together on a bunch of things he was about to go back to his uh to his prior job he had tried to kind of make it as a creator and then he was trying to go back to his prior job and i was like why don't you just come work with me this will be way more fun and so he did and that was a few years ago and we've had an amazing run he sort of

he is like my, uh, he's like the complimentary skillset to me. So he's unbelievably operationally focused. He knows how to like manage notion and all of the things that would be like needing to keep the trains running on time. He's exceptional at, um, and he also just knows my energy really well. So he travels with me almost everywhere now. And, um,

I get really drained by like, you know, public appearance or being around a lot of people that drains me. And he sort of is like totally fine. He's more introverted. So he's totally fine just being quiet, like having dinner and we're just kind of quiet versus if he was super extroverted, that it would be tough. And so it's just been an amazing relationship and an amazing complimentary relationship to to build around and achieve. I mean, chief of staff is kind of a role that.

Is relatively new, but he effectively manages all of the different people along the media team and then also the relationships with anyone externally or anything going on. So any of the operators at the different companies, he's kind of like a firewall between me and them to make sure that like the right things are getting to me. Other things are just handled. But now underneath him, there's.

someone running book process. There's a bunch of editors doing video stuff. There's web stuff that's going on. There's the newsletter stuff that's going on. So he really is, he has like a team under him of kind of direct reports. And then basically he's the only one that reports into me. I love that. So your energy really is protected. Really protected now. And that's been amazing for just, especially with the book and like needing to have the time to really focus creatively, as you know. It

it's been enormously helpful for that. Yeah. Yeah. That's definitely something I'm thinking through now too with the book. Like, Oh, this is a whole different level of focus. And so thinking about how I can step away from my businesses in that way has been really empowering and also feels like another level. Like, Oh, I know something good's going to come of this. So it's always so interesting stepping into new phases like that. So my last question is as you're talking, what I'm really hearing from you, and it's a concept you talk a lot about on the podcast is,

is this concept of knowing when enough is enough and everything beyond that is beyond that. It's fun, it's joyful and if it stops being that, it's a hard no. And I feel like in our society, it's very easy to get swept into nothing's ever enough, always chasing more. It sounds like you have a really great balance there. How do you maintain that? And did having a baby change that for you or was that like something that came out of 2020? Yeah.

That was definitely having a baby that taught me that. I mean, I had spent... I'm highly ambitious, as you are, and as I'm sure many of your listeners are. And I had spent my whole life...

chasing some more, whatever it was, whether it was first, it was getting a scholarship to go play baseball. Then it was whatever was happening in school. Then it was getting a job that I thought was great. Then it was making whatever next title promotion bonus, fancy bottle of wine, whatever the thing was, I was always chasing the next thing. And I always told myself that my happiness and like that idyllic land of feeling like a success was on the other side of that more. And then inevitably I would get there and be like,

Is this it? What's... You know, I'm not happy. I'm not fulfilled. I don't feel the thing. I just need the next whatever it is. And it's... That's a phenomenon. It's called the arrival fallacy. You feel like you're all of a sudden gonna have arrived once you achieve some more, whatever that is. And after my son was born, I...

I had like one very specific morning shortly after he was born and I brought him into bed. My wife was still asleep and he was like lying there. This is, you know, he's two weeks old and he had this like little, you know, baby cute content smile on his face. His eyes were closed and the sunlight was like coming in through the windows. My wife was asleep. It was a Saturday morning. And I just had this sensation for the first time in my life that, uh,

I had arrived and I was like, I don't need, I actually don't need anything more. This is always going to be enough. And it makes me emotional even thinking about it today. But that was the first time in my life that I had felt that. And ever since then, whenever I start feeling that need to chase,

There's nothing wrong with that. It's reminding yourself that like ambition is great. There's nothing wrong with it. But I always need to have that center around recognizing my version of enough and remembering that if nothing else works.

This is always going to be enough. And like this family and my, you know, my wife's health, my son's health, my parents, like that is always going to be enough for me. So that is, I mean, for me, that was a very, very formative moment. It's beautiful because as you say that I can remember the exact same moment I had very viscerally of the exact same realization of looking around and realizing I have everything I ever wanted.

And I think having that as a reference point to always come back to helps you to say no to so many things and helps you to say yes to the things that actually is this going to bring me more joy? Does this feel creatively fulfilling? But I love having these conversations because when you're in those earlier stages and you're, you know, you're working to put a roof over your head, you're working to put food on the table.

having these kinds of thoughts stuff in the luxury because you're like, no, I need to put food on the table. But once you arrive to a certain level of safety, if you don't allow that to settle in your nervous system, I feel like you keep chasing that without realizing you already have it. And so I think it's beautiful that for people that look in and think, well, you've arrived, you've made it. I think it's really important to have these conversations of, well, when you arrive, you realize you had it all along. Totally agree.

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