Steve Schlafman - This VC/founder believes being fluid in life is the ultimate ambition!

I talked about this idea of, um, holistic ambition, which is this intentional desire to be, become, or create something new, better, or different that is aligned with who we are and what we value. And so in the piece, I talk about how this could be everything from designing a dream house to ensuring your sick parents have comfortable end of life. Training for a half marathon, or you know, frankly, and this might resonate with you, or just being more patient around your kids, right? And so I think that we need to kind of step back from this idea of you know ambition is only tied to work.

Hello, hello, beautiful people! Thank you again for tuning into the Undefeated Underdogs Podcast. I'm your host, Sharad. I am so, so, so stoked to. have this guest on my podcast today. Where do I start? I think it's been a long time since I had this, you know, the conversation with the guest. But without further ado, let's welcome Steve Schlofman. How are you feeling, Steve? Welcome to the show.

Good, good. I just had lunch, so I have a full stomach, and I'm eager to be here, and it's nice to see you again.

Absolutely. Yeah. I think quick fun fact, I think this goes back to like 3 years ago, if I'm not wrong, when I was actually exploring the no-code projects, you and I, we wanted to like hop on a call and we wanted to collaborate on a side project. It didn't work out well, but I got to know you better. So that's like the benefit out of it. And man, where do I start about Steve. Steve. So first of all, you want me to call you Steve or Schlaf? Because most of— most folks call you Schlaf.

Yeah, you can call me whatever you feel most comfortable with, Steve or Schlaf. You just can't call me Steven because my mom— my mom— that's reserved for my mother.

Oh, okay. That's good to know. Okay, let's call— let's, let's go with Schlaf because I think that's where you're well known. So Schlaf is a professional transition coach. I want to also, you know, kind of unpack about that. Later in the episode, but he's a writer, podcaster, teacher, and a girl dad. Amazing. He switched many hats from being a newspaper delivery boy to working at world-changing brands like Microsoft and a sports team, New England Patriots, to investing in startups and now being a coach and a writer for his newsletter, Where the Road Bends. I love that name. Currently, Steve is on a social media break, so I want to take a moment and express my gratitude and appreciation for coming on this podcast because it means a lot. You would have said, hey man, I'm out, I'm on a break, but I appreciate you.

I'm still doing some podcasts, so I'm not entirely off of the web. I'm just not spending my time and attention focus in the social media feeds.

Right. So right off the bat, I have this question. So I read the blog, the post about why you're going away from the feed, meaning I think you put it really well. Your presence is more important than your feed, right?

I

think that's the best way to say that I'm taking a social break. talk to me about the why. Why are you taking the break in the first place? And I also want to touch upon a couple of points, a couple of experiences you wrote in the post. But yeah, talk to me about what made you do this and how are you enjoying it?

Yeah, well, to answer the first question, and I wrote this in the post, but Geez, this was back in April. I was going down a rabbit hole on artificial intelligence like so many people have been doing. And I listened to an interview between Max Tegmark, the artificial intelligence and machine learning researcher at MIT, on Lex Fridman's show. And Max effectively said to his wife that He sort of believes that humanity has been given a cancer diagnosis and it could be life-threatening. There's also a chance we survive it. And so with that, I took out my journal in the days that followed and was like, okay, well, if we've all been given this metaphorical cancer diagnosis, how do I want to live with that? Mm-hmm. And the thing that really, I mean, a bunch of stuff came up as I share in the post, but what really came to the surface was I just want to be more present. I, you know, I want to be more intentional with how I use what I personally believe is really the most priceless, scarce resource that we have, which is our attention.

Right.

And really presence. And so that led me on a journey to look at all of the ways in which I lose presence and the things that take me out of presence, things that trigger me. And over the course of a few weeks, I just observed myself like I was, you know, a scientist studying lions on the Serengeti. And what I discovered was that the one thing that reliably took me out of presence and eroded my, the quality of my attention was social media, specifically Twitter. And I went back and forth for a long time and rationalized, well, you have 70,000+ followers. This is a lot of your business is driven off of Twitter. And I just, that rationalization took place over the course of several months. And finally, I had this experience on a medicine journey that I won't get into here, but coming out of it, it was like, okay, I'm ready to really put down my phone and And start to just cultivate the state of presence that I'm longing for. And to answer your second question with a shorter and more pointed answer, it's been amazing. It really— like, I haven't missed it one bit. You know, there are some aspects that actually— it's not true. There are some aspects of it that I do miss, but on the whole, it's been really nice. And I feel like Just things have slowed down. I'm able to more intentionally divert where I put my attention because you know the information that I'm getting is no longer algorithmically generated, and so I'm really able to kind of feel my way into what it is that I want to consume and why. Yeah, and it's I'm just seeing the ripple effects in my life, whether it's you know at work or. Or at home being with my girls.

Yeah. So a couple of follow-ups. For the first follow-up, I know, I think we live in a very digital age and our digital presence is, you know, again, you correct me if I'm wrong. You saw the other side. I didn't see the other side. So you tell me, like, you know, if the statement itself makes sense. Yeah, we live in a digital world where our online presence, our digital presence actually is tied to our livelihood, right? Like founders, they're not on social, like promoting their stuff, talking about their business or their ideas, their features, products, the milestones. It gets very hard to grow and forget about scaling. Just, yeah. So yeah, you, that's why, that's the, that's why I want to like unpack what is that you, how do you feel about that? Like you said, maybe. So expand that maybe. And do you think still folks can achieve what they achieved when they are online, especially on Twitter, like, you know, these platforms?

Well, there's something that you said that triggered something in me. To me, it's not like, Our digital presence is the word you used. And what I like to say is at a certain point, it becomes our identity. And the more that we invest in that identity,

right,

the more we identify with it. And the more we identify with it, the harder it is to detach from that. And so why do I bring this up in the context of your question? Well, I think there's a lot of people on social media, whether you want to call them influencers, thought leaders, founders that use it as a means to grow. That presence ultimately becomes a significant part of them. And with that, there are narratives and stories and we tell ourselves, Especially if we're in the echo chamber of Silicon Valley, that the only way to build a company or to be successful in your career or to do certain things is to have an active presence online. Now, stepping back, I benefited being online for over 15 years, right? Like, I would not have had many of the opportunities that I came across if I wasn't. Now that said, with a little bit of distance, what I've come to realize, Sharath, is that there are many different ways to play the game. And this is something that I still work with a few investor clients and everyone's like, oh, I have to be on social media. How are founders going to find me? And it's like, maybe like I can point to a handful of investors that have no presence on social media and that are highly successful. I bet you and I could come up with a list of 100 entrepreneurs that have been insanely successful that aren't on social media. So it really comes down to, you know, what are the stories you're telling yourself and what are the games you want to play? If it's something you enjoy and you're naturally gifted at it and it really drives your business, great. If it doesn't feel natural and you feel like you're going against the flow, then, you know, why, why continue to do it? In the context of coaching, because that's now the, I guess, the business that I'm in, you know, there are a number of coaches that have built insanely successful practices and frankly companies, not, you know, unicorn, but, you know, businesses that probably generate 7 figures in profit and do very, very well. They have zero presence online. So I think it's just my way of saying, like, I don't think it's— I think it can be a catalyst and can absolutely help, but I don't necessarily believe it's necessary.

It's a must. It's what you're saying is kind of like a good point to think about. It's not a must. It's something that you choose for. And if, like you said, if If the personality is tending towards it and not causing distress, not causing the identity crisis, or not causing this suffering of like, hey, why am I not getting the vanity metrics everybody chases about? I feel if we balance that out, I feel it's a great way. So you also remind me, so I'm reading Steve Jobs' biography for the second time. you know, this is— they want to do it. Yeah, second time, because now I'm in more startups. I read before I entered into startups, I was fascinated by, wow, this is all like amazing. Now I want to add my perspective and read his thinking and how he did things. One thing amazed me was he never had a social presence, like never, right? Like, so '70s. There is no social. So actually, that actually gave to your point. I was also, that was also in my back of my mind. How the hell did Apple do it when there is actually no social game itself, right? Like now everybody plays social game.

Well, they created a new category of product and discovered that people want this. Now, as I'm listening to you, what's interesting is you use Steve Jobs. Like, obviously, it's Steve, like, pioneer, you know, one of the greatest entrepreneurs in modern times. I think about Carl Rogers, the well-known American psychologist, right? And he, you know, he wrote in 1961 a book called On Becoming. So, he was raised in the 1920s and is really credited credited with, you know, a bunch of, um, key ideas that led to the coaching profession, such as like unconditional positive regard, which means like I show up for my clients and see them in a positive light.

Mm-hmm.

As someone like finding one, just one or two aspects of them that I see as, as positive and as, as, as, um, really nice qualities. Why do I bring this up in the context of your story about Steve Jobs? Well, if you knew anything about Carl Rogers, he spent almost the first decade of his career in Rochester, New York, making $2,500 a year. I'm going to say that again, $2,500 a year. Wow. All he did was counsel young troubled youth, boys specifically. Almost a decade of his life, no professional interaction. He, you know, he didn't say this, but effectively said this in his book. He was in Siberia, but it was that experience of putting his head down and just doing the work. Nobody was watching. And through that foundation of experience, some of the most influential approaches and philosophies around supporting human beings came to fruition. And so I think, listen, social media and being present online and building in public and all these things, it's a wonderful thing. But I also think there's no substitute for just putting your head down and doing the work.

I think that's, we should all spend a lot of time thinking about that. Like, probably we should— I don't know, I probably— I'm thinking that to start like a week off and week on to try it out, like, you know, how it feels when you put heads down working on something, not worrying about what other people think or anything that, that, that's kind of like distracts from us to actually focus on what we want to do, right? Man, this is—

Well, yeah. And listen, I appreciate you being willing to have this conversation with me because I know a big part of your identity is being the build-in-public guy. And as I sit here, listen, I've built in public. There's no judgment towards the way that you show up in the world. What I'm simply saying is like in the case of like a Carl Rogers or Steve Jobs, Like, I think it's very easy for us to look to the influencers of today that are sharing online and their experience. And by the way, a lot of those are completely valid and there's wisdom and real knowledge and it's helping a lot of people. And I think there's a whole host of people like Carl Rogers that Nobody, very few people on Twitter even know that that exists. And you could pick up his biography and read even 100 pages of it and be like, wow, this thing is just dripping with wisdom. So I want to be— what I'm coming to appreciate, especially as I've moved away from social 2 months ago, is revisiting these older books, is revisiting these older body of works and honoring them. Because it's not like, hey, I learned this thing because I just started doing this thing. It's like, no, I've— he was embedded in his practice for decades. And that this body of work that he's sharing with the world is the culmination of that. So it's just, you know, it's just a different lens. And what I would say is, can you, can you, is there a way to hold both as, as, as ways to learn? Can you honor the past and be in the now and learn from who's out in front and sharing all the great things that they're learning in real time?

That's true. I feel, yeah, you made me think about we all should have retreats. I think what you're doing right now is kind of going to a retreat.

That's exactly what it is. That's a great way to put it.

Cutting down everything. Sabbatical. Correct. Yeah, I think we should all have like a, like take a mini, maybe like a quarterly sabbatical because sabbatical, the word itself is stigmatized, right? Like if you are not doing anything, at least to me, right? Like where I come from in India, if you are taking sabbatical and not doing any work, you are lazy, period.

I mean, that's true for the United States as well. In my coaching practice, I work with some amazing clients that have— I mean, all of them have had a fair amount of success or tremendous amount of success. And the thing that I hear over and over, and these are people that in some cases never have to work a day again, have taken companies public, have served presidents of the United States. Right. And they feel like they, they need to, like, if someone asks them what are they doing, there's a, there's a, there's a feeling that they need to come up with an answer that will be socially acceptable. And if it's, hey, I don't know what I'm doing, then that, then that, like, that's not socially accepted. And like, people will be like, well, what do you mean? You're like, you're, you're searching for what's next or you're not. You're not doing anything. You're resting.

Right. I think I want to put it in an analogy. It's like a car refilling the gas once it's done its course, right? So I think sometimes I stretch. I can talk about myself. I stretch, stretch, stretch, stretch. And all of a sudden I feel like very stressed out, very depressed that none of the things I'm doing is actually working. Right? So these books, talking to people like you, that's why I'm doing this podcast. It actually resets my perspective now and then. Every episode, everybody brings a new angle. Today you are bringing me that, hey, it's okay to take a small break out of everything, like focus on people who majority of don't know. I don't know who Carl Rogers is too. I'll be honest, I have no clue till you said about it.

I wouldn't expect you to know who he is.

So I feel like, like you said, you know, tributing the past, tributing that wisdom, soaking yourself in is really important. And I'm taking away that lesson with me. I want to

do like a second follow-up. Can I quickly just add one point, Sharaf? The other thing that I would mention is that if you and I were having this conversation a month ago, I mean, 3 months ago, certainly 6 months ago, I would have had a very different perspective on this stuff. And so, it's my way of saying, as— and this is something that I spend time with my clients on— but as we move through time and space and we embed ourselves in environments and systems, it ultimately influences who we become.

Hmm.

And so, if we have a conversation, another comment, if we do round 2 in a year from now, My guess is I might have very different opinions and beliefs and perspectives on this very topic. So,

in

other words, I'm not holding these things very tightly because they're going to shift and evolve and emerge.

You're very fluid. That's what you're saying. It's fluid like water, in Bruce Lee's words, like be like water. Go as you go.

Which is why if you look at my Twitter bio and what I've been—

The second, my follow-up question to the second part, how are you building these habits? Are you building any habits when you feel like FOMO or when you feel like, oh my God, I want to go back to my feed? How are you diverting yourself positively, not forcefully, positively? that you want to share with us? Because I think that's truly important, having like a practice where you took a stand and you actually are disciplined towards it. So any habits or anything that you are doing by not getting back to social?

Yeah, so a few things. First is because it came from a place of choosing a way of being, right? It's not like I was coming at this from the standpoint of, oh, I got— I mean, there were, there were plenty of months and there have been plenty of times where it's like, I got to get off social. I can't, right? Um, and so to use my, my, my teacher's parlance language, I was below the line. I was triggered. I was activated. It was very hard for me to create sustainable, lasting behavior change when I am triggered and activated. So the fact that this time around I started from this position of, well, what's the quality that I want to embody? And that was presence. And because I've had a meditation practice for almost a decade, when I'm on the cushion, Mm-hmm. Or I, I, I know what the quality of presence feels like, and I know what it doesn't feel like. And so this is, this is, I'm, I'm saying this as a, as a, as an entry point into your question because when we're like, I knew the quality that I wanted, like I could feel it in my bones. And so when I'm not feeling that way, then I know I'm not being the way that I aspire to be or live the way that I want to live and so on and so forth. So from that point, the habits were able to flow pretty naturally because I could feel when I'm taken out of that state and so on. So here's the way, here's how I designed around it is I basically deleted social media off my phone. Right? All the apps gone.

Hearing itself makes me like, oh my God, how did you do that? Yeah,

just hit delete. Just, you know, hit hard tap the icon and started wiggling and press the X in the top right corner. But yeah, so I deleted it. The other thing you should know, which is I think I I'm a big New England Patriots fan, having worked for the organization and grew up watching the team. All of my news comes from Twitter and it's preseason. And so what I do is I log on once a day. I have a very specific curated list and I give myself 5 to 10 minutes to just read about the Patriots because I feel like Twitter is the best source for that information. And I log off. I don't touch the main feed. Occasionally I'll check my DMs because a lot of people still reach out to me. And that's it. And that's the habit. But it really started— I also have 2-factor authentication to make it really hard. So I log out every time I log in. So the habit is removed it off my phone, enabled 2-factor authentication. And then when I log in, I have to log in. And that forces me to be highly intentional about how I use it.

And I like that.

If I'm being honest, like that's the core habit and the behaviors around it, but it really starts from what is it? What's the state of being that I want to cultivate?

I want to ask you a question about, so now that you're experiencing present, a lot of times I can talk about myself. I barely experience present, meaning I'm either always chasing something. I don't know if it's good or bad. I'm being very vulnerable here. Like, I have this project, I have this idea I want to— I have this idea I want to tweet out, or I have this, you know, interesting experiment I want to make. Always chasing something or dwelling in the past. Meaning, oh my God, some pain will come to my mind and some relationship, something that comes bothers me. So in Naval's words, I try to inbox zero myself. The most present I am is with my son, my 2-year-old toddler. He's like absolutely present. He reminds me of This is it. No phone, no TV, only him, toys. That's it. His questions, his curiosity, experiencing that and all that. So given you are experiencing more than I'm experiencing, which is, you know, not being on social for whatever reason, like define present.

Yeah. So, so Presence is the way that I— I mean, there are many, many great definitions of presence, including a number of which I include in that last essay I published. But to me, it's when all of your senses are wide open and you're taking in the totality of your experience. So said another way, Your eyes are open, your ears are open, your nose, your taste, touch. Like you can, you can feel your body, you can feel your feet on the ground. The Buddhists would say there's a 6th sense, which is kind of mindfulness, the ability to be aware of your thoughts, metacognition, things like that. And so when we're able to be with our totality of experience, What we realize is there's a lot more information that is that is coming at us at all times, and the reality is is the like the volumes of the hundreds of thousands if not millions of bits that are flying at us from our environment at any given time. Only a small percentage are actually getting through to us. It would be too much for our brain to take in, but if we allow ourselves. To start to like give ourselves the capacity to be with more. It ultimately allows us to observe ourselves, to observe how we respond in the world. And with that, it creates choice. As opposed to just, you know, as a lot of the Buddhist teachers and spiritual teachers would say, instead of just sleepwalking through life and reacting and just, you know, go, go, go, go, go. Or, you know, looking back in the past.

So what's— what you said is absolutely interesting. I've so far, I've only known that being present is observing your mind, observing your thoughts. It's a meta presence. But what you're saying is absolutely interesting, which is you're saying that there is a physical aspect to it. You can feel your bodily senses. So much. Is that scary to you?

Well, I mean, I think it can be scary at times, depending on what sensations I'm experiencing in a given moment. You know, I've suffered from chronic chest pain, largely due to muscle tightness, anxiety, constriction. Now I can feel constriction in my body pretty easily. When it first, when I first started meditating and then being more conscious to this constriction and this like, this like tightness in my chest, I was freaked out. I thought, you know, I thought I was going to die. I'm not joking. Like legitimately frightened. Wow. And especially when I was feeling that in a 10-day meditation retreat that was silent. or I couldn't really talk to anyone. Frightening. And so, that's not to say that this choosing this path of presence isn't worth it. What I believe, especially whether it's business or creative pursuits, having this presence is actually a superpower because you're able to tap into the totality of your experience and ultimately— Mm-hmm. Choose, like, follow your energy, right? Be able to just naturally follow curiosity, to know what excites you, to be able to feel like, oh, this person said something and I feel like I'm feeling constricted. And like, I might not even be able to, like, might be subconscious, not unconscious, not conscious, but like, There's something that just doesn't feel right in my body. What? And so by having presence, it allows us to kind of be with it and start to know ourselves better.

I like that a lot. And so talk to me about how much of the influence your presence made on your business, the coaching, be it coaching, be it writing, be it everything that you're doing right now. Talk to me about, did you see like a difference between using your own brainpower before and after? If yes.

Yeah. I mean, this is probably the answer you don't want to hear, but I find that the more that I'm in presence, the more I want to be in presence, which means what are the things that bring me into presence? Most of the time being with my family like you. So, like, you know, being with kids is a great way to do that. Being in nature, moving my body, meditating. And so those things take time.

Hmm.

And so as a result of it, if I'm trying to cultivate these states, um, it means I'm not working as much and I'm leaving money and growth on the table because I'm choosing consciously to cultivate these states. Now that said, yeah, and now that said, like, how's business going? Business is going great. You know, it's— I have— I work with 16 amazing clients. I could work with many more, but I like keeping my practice small. Um, and I've been off social media and I still have people reaching out to me almost every day for coaching. So, you know, It's not like my concerns of my business drying up and dying. If anything, Sharath, you know what it's allowing me to do is be way more intentional about the practice that I want to create. And it's given me just enough space to start to think about a philosophy of change and transition and a philosophy of coaching that will hopefully you know, helped me evolve my practice such that, you know, in 5 to 10 years, there's a really strong foundation that was laid that couldn't have been achieved or would have taken much longer had I still been— and I'm holding up my phone for those in the audience, you know, stuck in the feeds. Right. Because my attention was too fragmented. Like, I'm unable— I was unable to make certain associations and connections because You know, my attention was constantly being hijacked. And by the way, like, I have self-compassion and because I know, I know that these products, you know, are very addictive, right? Mm-hmm. And I have a lot of clients that are addicted to them. So, you know, this is not, this is not easy, right? These, these companies have designed these products to be incredibly habit-forming. So just the reality of them. And again, like I've spent, I was on Twitter for 15 years. Like I can't even tell you how many hours I spent in the product.

Thousands probably. You keep on talking about success and you kind of like partially define, like for Carl Rogers, you define like a different success. You're defining a different success for yourself. for other folks, so on and so forth. Talk to me about it. What is success to you now that you're experiencing at this phase of your life? Yeah. What do you think about success and how are you defining for yourself?

Yeah. So back in the fall, so I guess we're recording in August of 2023. I published a piece called Rethinking Ambition, and in it I talked about how ambition is a dirty word. You know, it's very polarizing. You know, some people believe you have to have ambition to be successful and to get ahead and, you know, kind of evolve. And then there's some people, you know, on the other side of the debate that think ambition just kind of in growth at all costs leads to a whole host of externalities that are quite negative. And I don't necessarily believe that ambition needs to be so polarizing. In fact, I actually think that ambition is a really powerful motivating force for everybody, right? It gives people a sense of purpose. And so I was thinking that because these 2 definitions or like these 2 camps of ambition, like I just didn't see enough in the middle. And so I wrote in this piece, I talked about this idea of holistic ambition, which is this intentional desire to be, become, or create something new, better, or different. that is aligned with who we are and what we value. And so, in the piece, I talk about how this could be everything from designing a dream house to ensuring your sick parents have comfortable end of life, training for a half marathon, or frankly, and this might resonate with you, or just being more patient around your kids. And so, I think that we need to kind of step back from this idea of, you know, ambition is only tied to work. And then seeing that ambition actually has multiple, um, dimensions if we're willing to look at it through this holistic lens. And one dimension is creating ambition, right? Which is like focusing on what you want to create and bring into the world. Another flavor is becoming ambition. Simply, you know, which focuses on who and what you want to become. So like, for example, me being present and stepping into presence, that's a becoming ambition. There's a be— I would also say it's related to being ambition, which is focusing on like how you want to show up as a human being. And then there's a doing ambition, which is just like, what— how do you want to show up every day? And What's interesting is maybe 5 years ago, my ambition would have been to be, you know, actually not 5 years ago, I'd say more like 6 or 7 years ago, it would have been to be among the best venture capitalists in New York City. And now my ambition is quite different. It's like, yes, I aspire to develop expertise and mastery in my particular realm of coaching, and run a successful practice. But another ambition of mine is to be the father that I never had growing up, right? And so, I also have an ambition to take care of my body and my mind. And so, what I'm trying to get at for those in the audience is like, we can define success any way we want, but if we're looking at it just across one dimension, I believe we're shortchanging ourselves of what's really possible. And, you know, frankly, the benefits of having ambition.

I think there is a sense of contentment in your thoughts, right? Like, you basically— how do I put this? You want to do at your own terms. not in other people's terms. I think if we all can come to that sense, everything will be like super easy. There won't be like, you know, the misery or the suffering will go away. I mean, you won't fall into the trap of comparing yourself with others and so on and so forth, because that's one of the bad sides of Silicon Valley is Everybody is so flashy, like at least the successful founders, VCs, and not intentionally, they're not pushing, but it feels like if you do certain things, that means like, you know, you'll make a name or else you end up in the end of other spectrum.

To use Steve Jobs' terminology, you'll make a dent in the universe, right? Yes. And what I'm At this point in my life, what's interesting is I, through lots of healing and introspection and, you know, variety of other pursuits, what I came to realize and appreciate in myself is that for many, many years, I was living the life of other people. And You know, it only—it helps that I'm in my—I'm dating myself now, Sharath. I'm in my mid-forties, and I've lived long enough, and I've done like enough introspection and looked back to see how I didn't have as much agency and free will in crafting my path as I thought I had. That you know, I was absolutely influenced by by. things in my environment. And, you know, whether you want to call it mimesis, mimetic desire, what have you. And what I'm starting to really appreciate in my own life, and it took many years of like depatterning, you know, seeing all my tendencies and, and, and ultimately, you know, Carl Jung would call this individuation, but it's how do I really get to understand who I am? As a person, and then ultimately design a life around that, even if it means that I'm not going to ever start a billion-dollar company or run a billion-dollar venture capital fund. And at a certain point, I had to look in the mirror and say, okay, what's enough? What's enough? And it's a question that I ask pretty much all my clients, like, what's enough to you? And, and when you get it, is it going to be enough? Right, and and and it's it's here's something I'll just say to just close the point is I'm living in the woods. I have fifteen clients. I have two wonderful daughters, great wife, knock on wood, a healthy body, and um. You know, enough income to support the lifestyle that we want through my business. You know, will I ever make fuck you money? Will I ever drive a Lambo and have a yacht and, you know, vacation in Ibiza and all? No.

No.

But I'm okay with that. And I'm more ambitious now than I've ever been.

I think being in your own terms itself is ambitious. That's it. I feel

yeah, yeah.

You define your own thing.

It's like it's like it's like my buddy Jonathan Basker, who's a super talented coach and you know a very dear friend. When I was leaving the venture world, he said this to me, and I'll never forget it. He said, "You know, there's a there's a time where I thought I wasn't ambitious until I realized my ambition is to live a good life."

Oh man, that's.

And once he said that, it was like, oh, it's like, oh, wow, that's profound.

That's mic drop right there. That's a mic drop moment right there.

Wow.

That's awesome. I struggle with a set of things that you mentioned. Yeah. After I think my son is gone, the same thing you said, right? Like, you know, being in the race, everything I do should be in other people's terms, you know, by default. And immediate comparison, which will end up to jealousy. which will end up to

envy,

a lot of, yeah, a lot of anger towards myself, which will end up to not loving myself and hating myself, and which end up to like ungratefulness and so on and so forth. So I feel like, so I had, I went to meditation, you know, in Atlanta. This was, and during COVID as well. And the Buddhist teacher there, he taught us like, you know, Different, different practices, methods and all that. But he is, and at that time he was very happy and very content. And he used to run a restaurant. He still runs a restaurant, which is like, which is so far from the downtown. It's like away from everybody, like a small, simple business. And he removed so many of the things which I said. Like there's no point in being jealous with others. You live your own life. Would you trade what you have with the person you are comparing with? The answer is hell no, never.

Or maybe, but we often don't see the sacrifice and the cost that's required to go and achieve that life. Right, exactly. And you know, my my my good my good friend Holly Whitaker, she wrote this book called Quit Like a Woman and founded a company called Tempest. She you know she wrote an amazing piece on her Substack Recovering and her Substack's called Recovering. But she wrote this piece on like what's the cost of success, right? And we we only look at like GDP, you know to measure like economic output or income. But it's like, what's, what's the cost to maximize that? Right?

Like what's—

it doesn't— GDP doesn't take into account like what is actually required to produce that output. Like what are the externalities?

Right.

Just like we don't look at what's required to generate each dollar of income and what's the cost. And for some people it's not having a presence in their kid's life.

Right.

Or it's, you know, working themselves so much that they burn out and their nervous system's deregulated. And so it's just my way of saying, like, you know, to just piggyback off what you're saying is, yeah, there, you know, potentially there is a cost to this. And it's how do you want to— how do you ultimately want to be? It's all choices. Yeah. And if you do it from a place of being aware and conscious, that's great, right? There's nothing, nothing wrong whatsoever with wanting to be in the race, right? Like, I'm in the very early stages of a book project and, you know, whether I publish it, we'll, we'll, we'll see. But like, do I want the book to do well and be on the bestseller list? Like, my ego wants all of that. Of course. And like, I'm going to work my ass off, right? And so like, whether you want to call that like, it's okay to want success. I think there's a question just from what place is it coming from?

Exactly. And this is getting deep and I love it. I hope like listeners, you know, understand this and absorb this and implement this though. That's the most important piece. Let's switch gears a little bit. I want to talk about your early VC experience, early founder experience. What was that like? Do you ever miss— right now you're doing something else— that you want to build like a company again? Or what's your— some— I'm sure it comes to your mind at one point or the other. How do you navigate that? How do you handle that?

Yeah, you know, a few things come to mind. You know, first, do I miss it? I think there are some aspects of it that I miss. I miss the pursuit of the chase, you know, going to win a deal. Right. You know, getting conviction, you know, finding a founder that I absolutely love. I would say I miss working with founders and people in the business, but in a lot of ways through my coaching, I get a lot of that. The thing I don't miss is the constant pursuit, the taking pitch meetings every day, email flooded with pitches and having to call through all of them. Like, there were a lot of aspects of the business that caused a lot of anxiety and stress. First, unconsciously, because I was ignoring them. I was basically repressing and suppressing lots of thoughts and emotions. But then once I started to kind of wake up and clean up and grow up, as Ken Wilber would say, it became very clear that it just wasn't— this wasn't for me. And that I was really chasing someone else's dream. And now, I mean, there's definitely a number of relationships that I miss. But on the whole, I don't really miss it at all. I think my life today, even though my economic output is not close to what it used to be, is 1,000 times better. I work for myself. I get to pick the clients I work with. I get to help people. I work probably no more than 30 to 40 hours a week. I have freedom and autonomy. This afternoon, it's gorgeous out. There's not a cloud in the sky. I get to go for a bike ride. And so, I don't miss it. Now, that said, like, there is a part of me that wants to build something. And I don't think I want to go and build the Silicon Valley-style company, but I could imagine eventually building something in the coaching space, maybe a retreat center of sorts. I definitely have a lot of creative energy. Feel the desire to build something that's bigger than me. Now that said, I'm being very patient. I know exactly what like I'm very confident in the path that I'm on, and I'm trusting and have faith that something will emerge, and that when the time is ready, it will be ready. I don't I don't feel the need to try to force anything. It's like, can I flow with the river? And when the river When I stumble upon something and it feels right, then I'll go after it. Now, I do want to make one point kind of on the heels of whether I miss it. A few weeks ago, I went for a bike ride and I was like, you know, just for the sake of comparison, I was on 20 Minute VC with Harry Steffens. I mean, when he was very— I mean, within probably the first year or maybe second year of him getting started and I listened to it and it's so amazing. I'm like, this is like a different person that, that I was listening to. I'm like, I can't even believe this was my life, right? And so it just was such a great reminder that, you know, using a word that you said earlier, is like, life is fluid, man. Like, right, you know, it's like depending on, you know, kind of where the winds take us, we can It's why my Twitter bio now says, you know, I contain multitudes and potentials is because like I always hesitate getting too affixed to any sort of identity because I believe that, you know, if I really lean into this natural unfolding in my life, that it's going to change.

I love that. When did this shift happen? Me meaning the tactical side of Schlaf went to the philosophical side of Schlaf?

Well, if I look back at my high school journal, I think there was a philosophical, deeply introspective part of me from a very young age, which, yeah, which was kind of cool to see when I revisited a bunch of old journals. The fact that I was a jock, using kind of like American parlance and played football, yet I kept journals, probably should— tells you a lot. But yeah, so I think like this part has always been part of me. Now that said, it really started to take hold about a decade ago. I went away to— actually, it started well before that, if I'm being honest. Started practicing yoga in 2003. So I graduated from college in 2003. I moved to Seattle to work for Microsoft, and my ex-girlfriend from high school, who I'm still really close with, um, said that a friend of hers opened a yoga studio in Seattle, hot yoga studio, Power Vinyasa.

And,

you know, here I am like, yoga? Like, what, what, what the hell is yoga? Like, she's like, just try it.

Right.

Go to, go to my friend's class. She's an amazing teacher. You're gonna love her. And that was really kind of the first taste of it. Yoga's a moving meditation, right? Right.

It

wasn't until almost, um, you know, 12 years later, despite having a fairly regular yoga practice, where I read The Power of Now by Eckhart Tolle, literally on a whim, uh, while I was on vacation, uh, for my brother-in-law's wedding. And I read it, it knocked me on my ass immediately. I came home from the vacation and was introduced to a meditation teacher by a mutual friend, learned Transcendental Meditation, and, you know, my, my life has never been the same.

Awesome.

So it, you know, I, I would say it really started about a decade ago in terms of like the deep study and, you know, really wading in the waters.

It's awesome. I think I can't wait to see you write some of this stuff you mentioned in the book. So talk to me about, like, let's talk about your writing process. So you write Where the Road Bends, and most of your writings are stories. It's like you talking to me, you know, to another person. It doesn't feel like— no heavy words, very simple, more experiences, memories, and all that. So talk to me about like how you write and what are you excited about this book project?

Yeah, well, I would say that Where the Road Bends has really been a labor of love. I don't know who in the audience needs to hear this, but for many, many, many years, I mean, almost for more than, well, more than a decade, I had this deep desire to write. And when I was an investor, early days of an investor's call, like 2010, I spun up, I think, schlaf.me and would just occasionally write. And I always wanted to write, always. But then I was like, ah, it's kind of not that important. I have other things to do. Like if I spend all my time writing as an Investors, you know, like am I going to miss out on things? And I just kept on punting and punting and punting. And finally, when I decided to leave the investing world, I'm like, okay, I'm going to really make like I'm feeling called to really express myself using this medium. And I ended up hiring an editor, a woman by the name of Rachel Jeppson, who is a super close friend now. She's, you know, as I like to joke, she's like a coach. a therapist, an editor, um, and everything in between.

Right.

And I just fell in love with it. Yeah. And I just fell in love with the medium. And I, I write, I write morning pages pretty much every morning. Um, it's a big, big part of my practice and just the way that I start the day. Um, and what, where the road been, it's funny, actually, if I back up, when I started working with Rachel, she had me fill out like persona, like audience, like almost like audience development where I like fill out 3 different persona types and who I'm speaking to. And within like 4 months of me writing, it just was very clear that I wasn't really writing to founders or, you know, certainly they're in my audience. But for me, the thing that was really coming to the surface was more about how do we move through change and transition in a conscious and compassionate way. And it almost happened by accident, just by writing into my own experience and the things I was really interested in, and just sort of like, you know, my curiosity and energy went. And that's what, you know, I've just stepped into that process, and it's been— it's, it's been life-changing, right? It, it helps fuel my business, but I don't I don't view it as like I have to do this. It's very much like this is something I love doing. It's really challenging. Like writing is— I mean, most creative mediums, I believe, especially to do it at a very high level, is a real challenge. Um, but I, I just get so much satisfaction out of it. I love the topic of exploring conscious and compassionate, um, transition and personal evolution and Yeah, it's, it's been, it's been a real gift. And the best part is, is I literally feel like I'm still a freshman in high school and I'm learning every day. And, and it's, it's, it's been, it's been a wonderful process. And then in terms of the book project, something that I'm sort of sitting with is that it's very much an unfolding. I'm not like, I kicked really, I kicked the process off in May. I created, I got Reflect, which is kind of like Roam Research. So it's like a, what do you call it? Like a, a, a, a Zettelkasten or whatever. Yeah. Yeah. Yeah. So basically just a place to store thoughts and ideas. And I just started reading books like it, like, and, and posts online and revisiting, you know, things that I had read like an animal. And I walk around with this small little Moleskine and anytime I have a thought or I hear something. Um, I'll just write it down. I save articles and books in and all my highlights into this note-taking system. And for me, rather than being like, I have to do, like, it's going to be about this topic, it has to be this. It's more like, what am I collecting? Almost like I heard James Clear use this, but almost like I'm kind of like a hawk flying.

Yeah. Yeah.

And like, if I catch a glimpse of something, I'll just pick it up. And I don't know what that's going to evolve or morph into. And so really this process that I'm embracing is an unfolding. And so in June, at the beginning of June, I said, you know what? I don't have a book topic. I'm going to give myself until September. No pressure. And something that I said was like, okay, well, what's the question that I want to sit in? And the question I sit in was, what's the book that wants to come through me? What's the book that wants to come through me? What's the book that I want to express? And then rather than trying to answer it, I'm just following my curiosity and saving things. And sure, it's kind of all in this big theme of change and transition, but I've kept the aperture really wide open. And guess what? I'm now getting at a point where the topic is revealing itself. Nice. And by next week, I might even have a preliminary structure of the book. Because I'm trusting a process and I'm keeping in it. It's a creative flow as opposed to I got to do this. I have to force it. It's I'm going with the river versus against it.

I love that. I can't wait, to be honest. It's amazing. Good to hear the big update. I think throughout your life, you've moved Like I said in your intro, you've switched different hats. And I think currently you're also experiencing the transition going from being very active to being very active in prison, right? So I think that's the transition itself. And you coach on that topic. That itself is something that untapped, I would say. Nobody actually kind of showed us the path. So I would, I will be the first buyer for sure. You know, take it, take

it. If and when I publish, I should say when I publish the book, hopefully you'll have me back on the show and we can talk about it.

Absolutely. For sure. Yeah, I would love to. I think you'll definitely unveil a lot of these memories and love to talk about. Last question before we wrap up. I know we're over time. In your experience working with founders, I want to ask a tactical question. For the listeners,

like, you know, tactical question.

Yeah. So where do you think founders struggle? Early stage, people who want to grow, scale, like, doesn't matter. Like, predominantly, where do you think they can actually fix themselves?

Yeah, it's, listen, here's what I would say is it's It's so, it's really dependent on the person and the context of the situation. You know, I see founders struggle at all different points in their journey and based on all different things. Now, that said, if we're to step back and just say, what's the thing that I think is extremely challenging for most founders? And I think it is Finding product market fit cost effectively, and to me, product market that fit feels like the thing that is really really hard to nail, and it's almost like you you know it when you have it, and if you don't have it, you push and you fight and you claw and you scratch to to get it, and you throw lots of money at the problem and. You never quite know if you really have it. And so to me—

Any tips that you want to give about achieving product-market fit in your experience? And, you know, you've worked with thousands of founders.

Yeah, yeah. I would say like, you know, I would reserve that question for Lenny Rachitsky or, you know, other people that, you know, I think are world-class in this specific domain and topic. Now that said, I think there's really no substitute for living the problem or the product and either putting yourselves in the shoes of the customer in terms of defining what it is that you want or what you want to see in the world or frankly what it is that the customer wants. And I say those 3 things very distinctively Because if you look at coming back to Steve Jobs, he would say, people didn't know they needed a computer, right? Like Henry Ford said, if you ask people what they want, they'd say a faster horse. But it's what is it that you really have conviction over through your own lived experience and also talk to the customer. It's like, let me give you an example. I have product market fit with my coaching practice. I could definitely scale my practice. Like, I have no question because I think product market fit doesn't happen overnight. And on a time, like, the disservice of the funding cycle is you raise money and you have to go and raise money every 12 to 18 months, which means you basically need to come up with product market fit in 12 to 18 months.

Right.

Guess what? It's a complex context, meaning you could throw $10 million at the problem and not get product market fit. You could throw 2 engineers and some ramen at the problem and, you know, have something that has product market

fit.

So, so, so to me, it's about really being patient, really listening, and, you know, rigorous experimentation. And, you know, talking, talking, you know, getting out there. And, you know, for me, you know, I don't want to scale a unicorn. I just want to build a small little successful coaching practice.

So, you

know, I'm fortunate I found product market fit.

Right, right. It's also, I think, like you said, ties along with intention too, what you want to do, right?

Yeah, yeah. And then the other thing is just something I see ultra, I mean, you know, in terms of short, like I think product market fit is the most important milestone of any company, especially early on, and doing it cost-effectively. I think the other thing is there's a whole host of emotional challenges that I see founders struggle with. And again, it's really dependent on the person and the way they make sense and see the world. So everyone is so different. And yes, there's common themes, but, you know, there are definitely some flavors, imposter syndrome, not moving fast enough, interpersonal conflict, so on and so forth.

Schlaf, this is awesome. I know I've learned so much and you've dropped so many reminders that we all can really think about and implement in our lives. I feel being away from social, being very mindful and intentional meditation practices and being content, that's the important takeaway. I love that. And again, thank you so much for joining the podcast. I really appreciate it. Any closing thoughts before we wrap up?

Yeah, here's what I would say to those listening. You know, maybe, maybe you heard some new ideas today. And what I would encourage you to think about is, you know, by no means I'm dogmatic. What I would say is, you know, go and sort of live, live life and experience life and see what's true for you. My guess is it will change. And yeah, I just appreciate you being willing to hear me out. And yeah, I wish you all the best.

Awesome. I think on the high note, we can close it out. And thank you, all of you, for tuning in and listening to the podcast. This is where, you know, this is what I really enjoy, like bringing these intimate, like, you know, incredible conversations to you. That's my job. And I, you know, I do it selfishly because I love it. And stay tuned for more episodes, guys. We have some amazing guests like Schlaf joining the podcast. The next coming weeks. So stay tuned. That's all I could say. Cheers,

dude. This was awesome.