Why Founders Feel Lost After Success (Derek Haswell)

Holy shit, what do I do? It was so clear that I was like, this is not the game that I want to be playing, but I don't know what game I do want to be playing. I was running several, 5 different teams in the business, and I was not in a place to be running teams in the business. So I started calling in supports. I was working with a teacher, I was working with a therapist. Things in my life started really unraveling or falling apart. What does it mean to do this type of work from a place of enoughness. Financial success isn't going to do it, and attaching myself to some amazing mission also isn't going to do it. It was really about the need to have to prove myself as worthy or to be this thing. You know, it largely had gone away, and what was left was just the sense of, who am I without my company?

How did you answer that question?

Um, if the game is to be have a perfect relationship with something, you're playing the wrong game.

Hey, welcome to another episode of Money Stories. Today I am joined by my dear friend Derek Caswell, executive coach, founder of a company that I have massive respect for that's made a massive impact on the world, 10% Happier. Derek, welcome to the show.

Thanks for having me, Mike. Excited to have the conversation.

Yeah, definitely. I'm really excited for— to learn more about your journey. And everything that you can share as it, as it relates to finding true wealth. And that is well beyond money, right? Because I think that's, that's really what the show is all about. So I'd like to start by understanding how you grew up in relation to money and maybe how that drove you to become an entrepreneur.

Yeah, I love it. Confused is the short answer. My parents were amazing. And when I had— I was a family of 4 kids, 2 older brothers, a younger sister. My oldest brother was born when my parents were 21 and 19, and so they hit the ground running and were hustling. And so when I was growing up, I'll never forget the, the black Ford Escort that we drove around with the door that you had to elbow check in order to get out of it, and I remember thinking like, this is a totally normal thing. I love this. And I had my— a friend of mine was making fun of it one time, like, oh, that the black Ford Escort, like the beater that you guys have. And I just remember I was like, wait, what? And it was interesting because though my parents were hustling and really building from the ground up a lot on their own, the messages they sent us around money was don't think about it. We don't want you to think about it. We don't want you to pay attention to it. And so they generally created a life to their benefit, but just where we tried not to think about those kinds of things. And that extended all the way through what colleges that we were choosing. It was don't think about money was the core message. And so getting out into the world and And then realizing, wait, like, wait a minute, what? There's so much for me to then go out and learn. I just— my relationship with money was ignore it, which is also was my relationship with difficult emotions too. I was like, hey, let's bury these concerns and then just have a good time. And if we're not having a good time, let's redirect towards a better time somewhere. So, so yeah, it was, it was then filled with this confusion. How do I relate to this thing that society and culture is telling me is so important and that I've been taught to not think about? No, no. Yeah.

And there's a distinction that I'm hearing between money doesn't matter versus don't think about it. Can you kind of dive into what that might look like?

What was the unspoken message was, of course, that money mattered. You know, there were choices that we were making around, uh, when we'd go out to a restaurant, what we'd order, what was appropriate and what wasn't appropriate to order, um, around our clothes, how many clothes we bought when I was younger. And, um, and also as I grew older, as my siblings and I grew older, my parents did well. My mom, uh, went back to school with 4 kids to become an architect, and my dad continued his progression on a management track in business. And so more money started being possible as I was in high school and growing up. And with that more money, we started doing more things, more choices became flexible, and it seemed like more joy was able to be had. Again, that was the feeling of it.

Sure.

So they— he has this very mixed message of don't think about it, don't think about it, don't think about it. But then clearly It's driving, it's an undercurrent to all the things, the choices that we're making, whether we go on vacation, where we go on vacation, what we eat, how we eat. So yeah, that's a nice distinction there that I think descends a little bit further into the confusion around money that I experienced when I was young.

And this is so inherent in our society. We all receive mixed messages around money. Work hard and be successful, but not too successful because eat the rich and, you know, rich people are evil. So from a cultural lens all the way down to familiar, we're always in this kind of dichotomy of how much is enough and should we think about this thing or should we not?

For me, so much of the journey, and we'll talk about this more later, is it's a journey into the complexity of things, right? So we tend to want to flatten. We tend to, as kids, developmentally, we're not far enough along to be able to hold the complexity of, Money is important, but don't pay attention to it. And so we tend to flatten things. And as we— yeah, as we grow, it's like I really appreciate that note of like, just how do we, how do we welcome the complexity of money and wealth? And as we'll talk about two different flavors of wealth that show up in our life instead of one-dimensional, it's money that means financial wealth and that means life is good. Which is the core message that we're sent. Oh yeah. How do— what other kinds of wealth are possible? Anyway, we'll talk more about that more later.

But yeah, definitely, definitely funny to dive into there. But okay, so take me back to you get out of college. Now you're acutely aware that money is in fact important.

Yeah.

What do you— where do you go from there?

Yeah. So I get out of college, I join a big company on the track that was like, go do that, then get an MBA and then keep on building. And this is kind of what was expected of me. And A year into the job, I was just like, I remember being at a client and the client was like, you're too smart for this job. I was like, well, like, what, what are we talking about here? And anyway, it helped, helped me wake up. So a year in, I was like, this clearly isn't a good track for me.

Insane.

And my parents at the same time were like, keep going, this is it. And part of the training was also that work wasn't meant to be enjoyable. Work's meant to be a bit of a grind, work hard, do what's right, duty. That was kind of another core message that I got. And, but I was always interested in starting companies. I was interested in how things were built. I have sketches from back in my high school and college years of businesses that would go on to be created. And I'd be like, hey, look, years ago I was drawing this thing, do you remember? And so a year into that company, I started poking my head up. I went back to, graduate program to learn more about entrepreneurship because I felt like going to school for this was the right thing to do.

Of course, obviously.

Anyway, I ended up cold calling startups. One of them brought me in and then I took this massive— I took a three-quarters— sorry, a 50% pay cut 2 years out of college because I was like, this is so much more my speed. Yeah. And I remember the journey to get there when I told my parents in particular, like, hey guys, I'm going to go join this startup. It's super this. And, you know, here's the financial situation of it. They were like, don't go.

What are you doing? What are you doing?

Like, what are you doing with your life? And they've been— I don't mean to paint them as any sort of bad guy. They've been incredibly supportive. And this particular junction was super challenging for them in their own relationship with money too. And so, yeah, I mean, credit to younger Derek and also Tess, my, then girlfriend, now wife. And I had a lot of support of like, do what's right. Like, this doesn't have to be a dutiful slog through life. And so I made the leap to startup land and I just got hooked. I got hooked on the people, which has been, you'll see, is a recurring theme for me. I've always fallen in love with people and I've always noticed an attunement to the shape of different folks and I got into startup land and all of a sudden I was surrounded by hungry, interested, engaged, intellectually curious along so many different dimensions people. And that really then kickstarted the like— I continued to bury the money thing. I was like, I don't care that I took a 50% pay cut, equity, yada, yada, yada. And but really, like, the people are incredible. And again, I'm actually kind of grateful. I kept my head in the sand for a bit and I'm grateful that I did. I wasn't super fixated on what the outcome was. But yeah, I found my thing. I found a way that I could build, be happy. I don't know if I answered your question.

Yeah, nailed it. And okay, so now you're in startup land, you find your people, you go, okay, this is for me. And really it sounds like found the gift relatively early of saying, okay, I'm not gonna run the treadmill of, you know, 2.5 kids and 2 cars and white picket fence and grinding a job that I hate only to retire at 65 and be too sick and tired to do anything that I want to do with my life. Like, you got off that train.

Yeah.

And what's the journey like to starting 10% Happier?

Yeah. So the first was this startup became a $40 million crater in the ground. So I had to go and do that, raised a bunch of money. It was an early product that helped people improve their sleep. So it was a sleep tracker back in the Quantified Self and early data tracking movement, launched the same time as Fitbit and super fascinating product, but it was a headband that you wore while you slept, staged your sleep patterns. Needless to say that people don't really want to wear a headband while they sleep. Weird, but it had enough success that it, it made it look like things were going to go. Anyway, so we did the startup things we built and we built some strategic partnerships. Some of those fell apart, company collapsed, but I got a bug. I caught a bug which was around behavior change. So I'd always been interested and this was like very driven by self-improvement. Derek, some sense of like there's growth, I'm hungry. These are the kind of messages that I was carrying, but The most interesting thing about the sleep tracking company is that it became— people would wear it, they'd get their sleep staged, and the first question they'd ask is, what do I do with it? And so right away, you know, we used to have initial slogans where if you measure it, you manage it. So if you measure your sleep, you're going to manage it better. And it's true to an extent, but behavior is complicated, really complicated. And so, um, we ended up going deep into the behavior science, worked with some incredible behavioral scientists back then to try to figure out what to do with it. This is part of the $40 million that was the creator. Got us spending money on incredible people. So I'm super grateful for that journey. And, and I caught the bug of like, what is change? How do we change? What does transformation look like? And on the outside of that journey, things in my life were improving. They're improving financially, they're improving physically, they're improving along a number of dimensions as well. But it was driven by this core desire to be enough, which we'll come back to. And once that company cratered, the founder of that company and I had become friends and we were tight, and he was trying to figure out what he wanted to do next. And we connected in Steamboat Springs, Colorado. We spent a winter together, him, his dog, and then my wife and I. So he was a third wheel. And, and we set out to try to figure out what it was that we're going to create around this shared fascination We were always at the lunch table at the last company talking about not just sleep, but all the other places that we were hacking or quantifying different aspects of our life.

Yeah.

And so the vision for what became 10% Happier started actually as much more of a masterclass for behavior change. So it was— we wanted to partner with authors who had written the books, eating healthier, exercising more, being more productive. And what we noticed was change was so hard. How can we make that much more doable for people? And the idea was take the books, turn them into beautiful courses, video courses, and then accompany them with a coach along the way. So that was the company that we—

sounds like a great idea.

Thanks. Yes, we raised some money. We set out to go and build that thing. And along the way, author number 9 that we worked with was Dan Harris. He had recently published a book called 10% Happier, which is about his journey through the weird self-help world around meditation. And he has this very disarming approach to meditation. And to his credit, he was like, hey guys, I'd love to build a course with you on meditation. This is a super passion, passion of mine. And also, I'm not your meditation teacher. We actually need to bring in a real meditation teacher. And so he called in Joseph Goldstein, who at the time I didn't know his name. From anyone. I was like, oh cool, a guy that Dan trusts. Turns out Joseph is one of the most well-respected meditation teachers in the West. He went to India and the East in the '70s, spent a decade there practicing with different teachers, and then started up Insight Meditation Society in Massachusetts, which is now one of the places that you want to go to meditate if you're interested in learning a particular flavor of insight meditation. Anyway, so Joseph, 75 at the time, um, I'll never forget, Mike, we sat down for the pre-shoot conversation about what we're going to do, and it was my first time to meet Joseph, and it was at Dan's parents' house in Massachusetts. And as soon as I walked in and I met Joseph, I was transfixed. Whatever this guy has going on, I want some of that.

I want that. Yeah, yeah.

And what was immediately apparent was it wasn't just like tricks or it was— he worked for that, you know, and there was a humility that was just there. So that was a big turning point for me. And so we produced this 9th course on the platform that we were building, 10% Happier. We launch it and it just starts going. And pretty quickly, me and my other co-founder Ben, are talking to each other saying, well, what if we just did meditation? And we're like, you know, Ben was like, well, we got to get a lot of things right, including Dan joining us, teachers joining us. And so we had a conversation with Dan at the time and we're like, hey, we've been doing a thing, you've been doing a thing. What if this thing just becomes one thing and we go build it together? We were at that point 2.5 years into the startup. We'd raised some seed funding. We had built a team of 11 to really just explore, up to 11 to explore the early product market fit. Days. And, you know, the, the early courses that we built showed enough signs of promise and traction that we leaned into it. And then as 10% Happier, we probably had one more course in us before we would have to really reevaluate the model anyway. But we saw 10% Happier had promise, and this was in something like July, and we were having conversations to to figure out what if we went all in and we stopped all of our other plans. And so stopping all the other plans, we knew we had runway from July until early the next year. So we set out embarking on these conversations. You know, cash is getting smaller and smaller, but we're keeping the team because we're going to keep on doing this thing. And then Tess, my wife, was pregnant with our first kiddo.

Perfect.

He was due in October and I'll never forget, we, I, my co-founder and I, Ben, are walking in the city of Boston on a Friday and he was, he said like, hey, money's getting tight right now. We may need to make some changes sooner than later. I hope your baby doesn't arrive this weekend.

Roro.

And sure enough, baby chooses to arrive that weekend. And 5 days into parental leave, I get the call from Ben saying, hey, I just talked to some of our investors. We need to lay off half of our company right now. And so I went in, you know, 5 days after welcoming our first kiddo. I'll never forget walking into the office and people were surprised to see me. Whoa, Derek, how are you? So good to see you. How's parenting life? And these, of course, are my friends at this point and people I trust and love. And I had to go in to do layoffs.

Devastating.

Devastating. And, you know, this is a credit to Ben, my co-founder. He was this— he is this very resilient, determined guy. And we endeavoured to show up for all of our layoffs with love. Didn't always do them perfectly, but fundamentally it wasn't about you're not good enough. It was about this isn't a fit right now. Anyway, so we had to go do layoffs. Things got hairy. And I think by the time we made all the agreements, locked them in by the end of the year, and then along the way we had found investors that were interested. I think we had 2 weeks of runway left when the wires hit our bank account to then start 10% Happier. And what's funny was we then launched that January, the following January, as a monthly subscription product. And we had 28 days of content on our app. And so the name of the game was go. You know, we had a thing that was working. It's now a subscription product. Just run at it. And it was just a really fun journey. I don't know how much of that investment we ended up spending because we pretty much just like came right out of the gates. All of our old customers signed up for the subscription and we were producing a new course a month with new different meditation teachers. And, you know, the difference between not having product-market fit and having product-market fit, it's something that when you know it, you know it. And we were just getting pulled in all of the interesting directions, trying to keep up with the pace of things. And that was the start of a, you know, 7-year run of just like up and to the right, fun, go build, work with incredible ethical, beautiful people and bring something out into the world that was fundamentally about some of the things that you talk about on this podcast too, healing our relationships with life and different dimensions of it, you know, through this lens of demystifying meditation. So we weren't super precious. Dan's brand really carried the company.

Yeah, sort of democratized meditation.

Yeah, I was like, hey, this is a thing. And 10% Happier, the name, you know, people always ask, why only 10%? Like, why don't I be 100% happier? And it was just meant to be a disarming way. And it was like, hey, I'm not going to overpromise and underdeliver, but this thing can make you 10% happier and it compounds if you stick with it. So I always appreciated that subtle message. So that's what we set out to do, was to show people that. And that was that chapter.

So, okay, taking you back to 2 weeks of runway, laying off half your team, where are you from a personal financial situation? New baby, junior just came into the world. Like, I want to understand the stress at that point.

Oh yeah, yeah. You know, so there's two different dimensions. One is in the seed founding stage of the business building, my co-founder was coming from a place where he wasn't as concerned about money. But my wife and I had, she quit her job. We decided to travel the country together, explore, kind of do a last hurrah before it was time for us to have kids. And money was tight. Money was tight for us. And so when Ben wanted to start a company together, he was like, okay, great, let's both fund the, you know, the initial seed round of capital and— sorry, an initial just like, you know, $50K each type of thing.

Yep.

And just to be able to run the basic operations to get to a point where we can do a fundraise. And we did that. And for him, it was, you know, no big deal. And for me, that was like all the savings, you know, that Tess and I had accumulated up to that point. I was like, okay, you know, and we're going to raise funding and this is going to be okay. And then, you know, fast forward a couple of months, we ended up moving back to Boston. So Tess, my wife, and I gave up on the trip across the country to explore. It was like time to go start this company. And we moved back to Boston, expensive city. You know, we're living off of her salary. And things were really tight, so tight that it was hard for me in that stretch to not be thinking about money and making choices all about money. And to his credit, my co-founder saw that. He's like, hey, I see you being really concerned here. What can we pay you out of the money that we invested to make it so that things aren't as stressful for you?

Wow.

Yeah. And so I think we paid me a salary of like $2,000 a month to help cover the rent and other things that we were doing, which again, I appreciate. And for him was like, you know, it was a little bit of a, hey, like, what the hell? But to his credit, he's, he's been a great co-founder and friend. We've been friends for 16 years. Needless to say, that initial time period was super tight. And then we closed the seed round of funding. We started paying ourselves a minimal salary. Happy days. Fast forward 2.5 years, money's running out. Basically, money in the company is running out. We're coming up on, you know, a month left of runway, laid off half the team. Are we going to be able to pull this off or not? And savings are still dry. So we're underpaying ourselves. Of course. And, you know, hey, this is part of this for Tess in my relationship was, hey, we're going to go start this thing. It's going to be successful and it's going to help take care of us in this life. Right. And so you know, all of a sudden we're faced with an impending cliff. Is this going to work? And then what's going to happen if it doesn't work? Right. I'm going to have to turn around and get a job ASAP. So there's a lot of the freneticism around like, oh no, are we going to make it work? And held our breath and it worked. So we landed— we ended up underpaying ourselves the entire time at the company. So we're building this company. It's got 8 figures in revenue. And we're still underpaying ourselves because this is an investment in a long-term future. So it was interesting. It was again, that complicated stemmed from the like, I don't want to think about it. It was, you know, Ben, my co-founder, was always quite frugal as well, and I was happy to go along for the ride with that. I didn't want to think about it. Hey, this is a long-term investment in money. And so, so it continues.

You're building a company that's actually doing good for the world. Right? So it's clear you have belief in the mission. You're dedicated to the cause. And yet so often as founders, we forget to include ourselves in the greater good, right? We're always willing to sacrifice, to push delayed gratification. And there's something beautiful about that, right? There's a requirement of that sacrifice. But then at some point it becomes a limitation. When did you become aware of that?

Yeah, well, I guess to build, and then I'll answer your question, it wasn't helped by the fact that we were working with these meditation teachers who had given their life to fundamentally service.

Yes.

And if you want to talk about people that were actually being underpaid, you know, we as a company did well to support the teachers that we worked with. But generally speaking, teachers are not paid. They don't live well. They're not living cushy lives. And so there was also the stark contrast between my tech friends running businesses the shape of the ones that we were running and what they were paying themselves and how they were doing things. Versus this more mission-driven company that we're trying to build, helping to support teachers in doing beautiful work in the world. So anyways, it was complicated. It was a complicated stew. And I think it further buried the stuff inside of me. Don't think about it. Don't worry about it. Just keep on going. And for me, the place that things really cracked open was on retreat. I was 8 days into a 9-day silent meditation retreat, and I was sitting, you know, I had enough time that concentration had built up, and I'm sitting in a room with friends and a teacher that I love, and I'm noticing moment by moment how every single thing I'm doing is driven by this need to be worthy. It was like my belly was sucked in and I was having thoughts about how I was going to eat the next meal and how I could do something that would be funny. And, and, but it wasn't just like, you know, one, two, was experience was laced with how do I be worthy, how do I be funny, you know. And it was, that was stemming from this, this place of unworthiness.

Where did, and where did that come from, or, or Were you even aware of that before this profound experience, or where do you think that started?

Oh, I mean, where doesn't it start in our culture? I mean, this is something that we're indoctrinated into. The easy answer is you look at our schools, you look at our jobs, you look at the way money works, and all the messages are you don't have enough, go do or be more. Um, you know, but for me, there was some awareness that there was an undercurrent of unworthiness going on in, you know, just as I did more meditation work and as I saw these people who are truly beautiful. It was like the examples I was seeing were like, again, they've got something going on that I don't have going on. Um, and I think where did it come from, and what I ultimately ended up seeing along my journey was it came from generations and generations, right? The confusion around money that my parents had when I was younger, it came from their parents and it came from their parents. And so that, you know, where does it come from? It's the soup that we swim in culturally, familially. And I was so grateful to see it. I was like, Holy cow. And how old were you? I was, I would've been probably 35. And so about 6 years ago.

Yeah, so you have this awakening cracking open experience, right?

Yeah.

All of a sudden everything's laid bare. I have been doing all of this from a place of lack. Yeah. Right? Yeah. And the paradox is, service, right? I'm doing this for the world, and you are bringing something. And this is something I think that there's nuance in entrepreneurship, right? It's not black or white, right? Like, rarely is, is, you know, someone driving from just a pure place of greed or selfishness like that. That's usually not— there are examples of that, but it's usually not the case, right? You're doing something really good for the world, something that you believe in, and yet you find these places where it's actually driven by not enoughness. And, you know, I'm just curious, where do you go from there? So you crack open on retreat and now what?

Yeah, yeah. That was the exact thought that I was having in that moment on retreat. It was, I'm so grateful that I'm seeing this and holy shit, what do I do? And it was so clear that I was like, this is not the game that I want to be playing. But I don't know what game I do want to be playing. And, and so for me, it actually triggered a months-long run of deep anxiety and depression where things in my life started really unraveling or falling apart. And by my support from my wife, support from my, my co-founders. But I remember having conversations like after that retreat, I was like, hey, at that point, the— I was running, you know, several, 5 different teams in the business and I was not in a place to be running teams in the business. So I started calling in supports. I was working with a teacher, I was working with a therapist, I was working with a coach. I was kind of like doing everything I could to grapple with this because I had to. Because the business, the success of the business depended on me getting my shit back together. But then I was still grappling with this open question of what does it mean to do this type of work from a place of enoughness? And so that journey eventually cracked graciously. One of my therapists, helped me see that the depression and the anxiety that ensued that seeing of, of, uh, feeling like I wasn't enough and wanting to be enough, that that anxiety and depression was actually love at the door. It was— these were ways that my system was trying to tell me, hey, there's something here for you to pay attention to, to connect in with.

Pointing out instructions.

Pointing out instructions. You got it, you got it. And so what I put the pieces back together enough after 4 months of the anxiety and depression. And then I kind of kept on building, but it was, it wasn't as, it was hollow. I was doing the building and I was going through the motions and I was doing the things, but I was like, without the need to try to prove myself worthy, why am I doing things in the ways that I was doing things? Why did I hire this many people? Why are we trying to go as big as we're trying to go? And, and it took another year and a half for those lessons to really start to integrate. And, and then for me to see I can't play this game anymore. I'm out of right relationship with this beautiful business on a beautiful mission with incredible people. I don't know that I have the capacity to do this from a loving place, which is where I ultimately wanted to go. And so that led to a conversation with my co-founders where I said, hey guys, I don't know what this means, but my time is done and I don't know where I'm going. But, you know, I'm sorry, this is my sense of things. And to their credit, they were like, hey, you don't owe the company anything. This makes total sense. And how can we help?

Wow.

So incredible.

Incredible to be met with grace in that moment. What a gift.

Yeah, what a gift. And, you know, I think part of that, the quality of the relationship that was there is what enabled me to show up to them and just say, I don't know what this means, but I think it's time for me. And so I spent the next 6 months building out the organization, you know, getting ready for my departure and then stepping out into the abyss of Okay, what do I want to do? What can I do from a place of enoughness?

I think your journey that you're describing here is actually the path of almost every founder I know, is that we start our companies to do two things. One, to improve our lot, to improve our situation, right? Find freedom ultimately, because most of us are unemployable when it comes down to it. But then two, and a little bit more insidious, is to fill a hole, right? And again, it doesn't mean that the mission of the company or that what you're doing is not putting good in the world, but if you're building to fill a hole, at some point, most of us reach this point where we go, oh no, this thing I'm building, no matter how much I build, no matter how much I achieve, no matter how much accolades that I win, this isn't gonna do it. I reached the same point in my career. And when you get to that place, what strikes me is that like most of us as high performers know when to let go of something that's not working. We know when to let go of toxic relationships, or at least, you know, can see that pretty clearly. As entrepreneurs, we tend to have a really hard time letting go of something that is working.

Oh yeah. That's us. That's our identity.

Right. Yeah, totally. And one of the questions that I help a lot of post-exit founders grapple with is, who am I without my company?

That's right.

How did you answer that question?

I answered it in the doing. You know, there was a— so at that point of exit, this inner journey had really started to integrate, and Yeah, there was the need to have to prove myself as worthy or to be this thing. You know, it largely had gone away. And, you know, fascinating, really fascinating journey. And what was left was just the sense of a way of being was more important than what it was that I was doing. And so, big credit to my coach at the time who helped me navigate this terrain. That focus on the way of being and my underlying core values became— it took center stage. So when I was evaluating what it was I was going to do next, you know, do I want to start the next thing? Do I want to join a big thing? Do I want to become an investor? It felt like I had the paradox of choice. There was a lot of things that I could do. And thankfully, the the orientation wasn't, how do I now plug the next hole of enoughness? It was almost like one of the benefits of starting a meditation company was there was no promise or allure that if I did a thing that was more aligned for me, that then it would, it would totally work. It was like, well, that was empty too. So financial success isn't going to do it, and attaching myself to some amazing mission also isn't going to do it. It was really about, uh, who I was in the doing of the thing. And so I'll never forget this exercise that my exec coach at the time had me do was, um, grade all of the potential paths that I might go down against my values. And one of my values happened to be, uh, loving awareness, which is much more of a way of being than it was a value. And I rated all the potential things and coaching was the only one that was green, green, green, green. And, and so I grappled with that, of course, because I was like, coaching, how am I going to help people at scale one-on-one? Ah, and but the evidence was there looking at me and that evidence was born of also doing some coaching and seeing what it was like to actually do that practice.

Yeah.

Anyway, so the The resolution was, okay, I'm just going to do this thing. I'm going to give myself to this thing that allows me to inhabit a way of being that is more authentically aligned with love, a way of being that was just open and that I could be on people's team. And it helped that it happened to leverage the things I was best at in business. I always joked that I was a goodish operator. I was a goodish founder, and I can get some stuff done, and I can certainly make things look like they're put together. But my superpowers were always around people. It was always around finding incredible people and developing them, seeing around the edges and corners of what it was that drove them. And coaching felt like a unique fit for me where I got to do something that leveraged those unique strengths and only those unique strengths. And I got to let go of some of the aspects of being a founder that, yeah, I wasn't as good at or developed at the time.

Yeah, something I always say about coaching that I love is that I get to solve problems all day, but they're not my problems, right? So I get to scratch, I get to scratch, yeah, I get to scratch that itch, but I don't have to take them home with me, right? And so yeah, it's a really great way to be of service and live in that space. And then the other thing that I've found with coaching that is such an unexpected gift is that I refuse to be out of alignment with my clients. I'm not going to ask a client that I'm going to do that to do something that I'm not willing to do myself. And so it becomes a forcing function to get your own life in alignment. I wonder if you can talk a little bit about your path at becoming a coach and what that's looked like.

Yeah, yeah. My path to becoming a coach has again been one of practice. I'll never forget another of my mentors in the space. I was talking to him about my my consternation around becoming a coach and what kind of impact I could have and size of the team and all that kind of stuff. And, um, he said, Derek, let me tell you a story. I was at my, uh, in a meeting with my retirement advisor, my financial advisor, me and my wife. And the retirement advisor asked my wife, you know, hey, when do you want to retire? And she was like, I want to retire at 50. And the financial advisor is like, okay, here we go. All right, okay, let's do it. And then And she looked at my friend and said, "Hey, when would you like to retire?" And his wife started laughing. And the financial advisor's like, "Why are you laughing? He's never going to retire." And the advisor looked at my friend and said, "You never going to retire?" He said, "No, I love what I do so much that the idea of retirement is completely bonkers to me." And he's a coach. And that was just a real turning point for me where he said like, when I'm 80 years old, I'll have accumulated so many reps of being with people that my skills and abilities and really capacity to be of service will just kind of continue to climb. So I want it to be my choice. But when I'm 80 years old, I still want to have 4 or 5 clients that I'm helping out on their own path. And then the tumblers just clicked for me there. I was like, oh, this is a path. I still have something in me to start. And there's some other stuff that I'm starting right now that we might talk about, but I can just give myself to this work and it'll be a part of the rest of my life. And the simplicity and ease that came with that really opened up the space for me just to step in. And again, the courtesy of the exec coach that I mentioned earlier, the orientation was towards a way of being. And, and I remember another story. There's a mentor of mine who's a therapist and meditation teacher. Incredible human. And I was talking to her about, you know, who am I to give people advice on their inner work or their outer work? Like, honestly, there are some people that I work with that are far beyond the levels of success that I've ever achieved. And then also in people's inner work, I'm really supporting some, you know, tender and sensitive terrain. Yeah. And she said, Derek, you don't need to worry about that. Let your clients hold that. You know, you can trust that if they sense that you're not at least half a step ahead of them, they'll stop being your client, no problem. And, and so again, there was just like another moment of freedom where it was like, yeah, I'm not going to be perfect, I'm not always going to have the way of being or all the crispness that I really hope to have, but I just get to step into this work, be me, do me, and, and let it rip. And then if I'm working with someone and they sense that their time with me is done, they'll let me know. So there's something really virtuous about the coaching feedback loop in that way, especially when approached from an authentic, I'm just going to show up and focus on the way of being. That, yeah, people will come in and out of my life and my work in ways that work for them. And so I've found coaching to be exceptionally— the feedback loop is towards alignment. And yet when we live our lives and we're out of alignment, that stuff stings more.

Yeah.

What is it like to be in our own life having just had a spat with our spouse and then go into a coaching conversation and have them want to process a spat that they're having with their spouse? Like, ooh, there's some out of alignmentness here. What does that mean? What is that asking of me in my relationship to my work, to my wife, to So anyway, that positive feedback loop is something I've really enjoyed and settled into. So imperfectly so, but necessarily imperfectly.

Yeah, I mean, there's something that has to happen, I think, as a coach, which is embracing being messy as a human, right? Like, it would be really nice to live in a world we have our shit together and never show up out of alignment, right? But as long as we're here, and waking up every day, that's probably not going to be the case. And so there's a forcing function of radical acceptance of like, hey, I can be here in my mess and I can also support you in yours.

Yeah, yeah, that's right. And what a gift too. Then the messes start to have meaning. The stuff that's surfacing in our own life gives us a chance to deepen with those things. And then of course, those lessons end up coming back in the work too. To.

So I assume as you exited, you had some sort of financial windfall that opened up a new possibility for you.

We did? No. Yeah, no, I'm still— I still have my equity in the business as I stepped away, and each of my co-founders are still building different dimensions of the business. So it came with a step out, and the coaching work stepped in as my work with the company ramped down. So it was one of those things where the plane landed itself. Yeah. In terms of the financial transition. And we just stepped into, oh, okay, cool. That's still a thing. And we're just going to step into this next thing. So interestingly, yeah, no, there was no financial windfall.

Got it. So, okay, you grew up with this story of ignore money.

Ignore money.

Money, basically. Uh, you sort of managed to build and grow a company with that kind of lurking in the background. How do you think about money now, and what does wealth mean to you now?

I'd love to say that my relationship with money is completely healed and I'm super conscious about every aspect of it, and the reality is like there still is a mix of the don't think about money that lives inside of my psyche. So part of the transition, it feels like it just happened from in the, in the company to building my own coaching thing in a way that didn't force me to have to address and deal with all of those things. And it's okay. Yeah. Along with that also came a deepening into the complexity of what money means for me. And it's really actually deepening the complexity of life. Right.

That—

so the classic thing that a lot of folks come to me now with is, hey, for folks that are particularly self-aware, I know that I've been building from a— with a dirty source of fuel, the shame or the unworthiness or the— help me build with a healthy form of fuel. And my response is like, okay, do you want to be 100% healthy fuel? Yeah, yeah, yeah, yeah, yeah. Not possible. Possible, right? The, the— all of these different shades are always there in some mix. And if the game is to be the— have a perfect relationship with something, you're playing the wrong game. And, and so anyway, the money for me has— it's complexified. It isn't as one-dimensional as have it or don't have it, have enough in order to do a certain thing that I want to do or don't. It's one dimension of life in the mix of other things. It enables certain possibilities and doesn't enable others. And it is, yeah, an evolving relationship. So how do I hold the complexity of my relationship with money alongside the thing that I'm building? So one other thing that I wanted to say in addition to the complexity of money is that I'll just say that the clean and dirty fuel metaphor is like, Yeah, it's not about just clean fuel. It's about how much dirty and how much clean and how do we continue to adjust the balance over time. And with awareness and with practice, it balances. It starts to balance out.

Totally. Yeah. One of the things that people often ask me as they're considering stepping into the work is, yeah, I think I want to go to this new fuel, but what if I lose my edge? And my answer often is you might, but you'll get to rebuild a new edge from a source of joy, from a source of life, from a source of getting to rather than having to. But it can be a destabilizing experience to let go. Kind of back to the earlier point, to let go of something that's worked really well for you.

That's right.

Because building from lack is effective.

Yep.

At least it can be.

It's a very powerful fuel, right?

Until it's not. And the trick is, I think, to maybe shift those fuel sources before the spectacular burnout and resulting impact crater.

Yeah, or let the burnout be burnout, you know, let the crater happen. And those things have a tremendous way of waking us up to what's possible, you know. And it's so common that you hear people that like, The business that cratered of mine was the biggest gift. I think I heard you say this yesterday. Yeah. Because it calls into stark contrast the relationship that we have with these things. So yeah, sometimes that's just what needs to happen.

And so pain is a great teacher.

Pain is a great teacher. And yeah, so, so, so often people are like, yeah, I want to switch to the clean fuel. And sometimes the answer is like, well, cut off the old source of fuel and switch to the new. But also, hey, this is knowing that it's not always going to be a pure mix of the other. For me, it's much more about this practice, this balance of like, how do we lean into this more and more to be with the fuel source, whatever shape it takes? And going back to your question about, you know, what's wealth? Capital— there's a lot of different kinds of capital. Financial capital is just one kind. And I forget the teacher, but there's a particular teacher who talks about 8 different forms of capital, financial capital being one, but there is social capital and relational capital, and there's a number of different flavors of capital. And so, so often we're conditioned as a society to say, well, if I invest this much financial capital in, it needs to yield that much financial capital out. And the curiosity for me is, hey, what if we're looking at capital through the lens of it's not just financial, but it shows up in all of the different aspects of I'm using capital in ways that you probably use wealth. Not— it's a— all of a sudden when it's not just about financial capital, but it's about the capital, the wealth of our entire life. Well, now there are tradeoffs to make. Oh yeah, maybe I am going to make much less money in this next chapter, but I'm going to trade that for other flavors of wealth that are going to help me build into this love for part of this practice too.

Yeah. I mean, the way I tend to think about it is that money is actually just a battery. Money is fuel. And financial wealth in of itself is actually sort of useless unless you use it to fuel the other types of wealth, right? And so, yeah, relational wealth, time wealth, energetic wealth, like whatever that looks like for you. And they all interrelate and sort of can compound on each other, but only if we're using money in service of actually building those things.

That's right.

Because, you know, something I say often is that wealth can actually only be experienced in the present.

Yeah.

Right? You can't be wealthy in the past, you can't be wealthy in the future, you can only be wealthy in right now. And so what are we choosing to do in this present moment? And money can buy experiences, money can help us take care of the people we love. And this is, you know, when we get— here's where I would like to go to kind of land the plane here is something that I've been sort of learning and understanding and wrestling with as I dive into more ancient wisdom tradition and Eastern philosophy is that non-attachment is often associated with denouncement. Or, you know, and I think the, you know, obviously the Western model of more for more's sake is incomplete. But, you know, I think most of us don't actually want to go meditate in a cave for the rest of our life and live in poverty. And a lot these teachers that are— that help so many people kind of take this martyr's path and leave themselves out of the greater good. And so how do you reconcile those two things?

Oh yeah, yeah, this is— for me, it's— this informs a huge part of the way I approach the coaching work as well. Um, our— if you think about it as a— instead of one axis, I can either be, you know, super hungry and successful or I can be super passive in a cave, peaceful. I think it becomes a really difficult choice, but I'll just flip that into a grid, right? So there's a— if one axis is wisdom, I'll just use for lack of better term, but it is our capacity to build from a place that is enough. And then the other aspect is actually agency is the way I think about it. What's your capacity or ability to drive impact in the world? And I'm interested in moving people up into the top right quadrant. And people start in different places, right? So there are some folks I've worked with that are incredibly wise. And from an agency perspective, they struggle to make things happen and make change in the world. I've worked with plenty of folks as well that are very high agency, but doing so from a place of lack.

Right.

And the good news is you can have both. This isn't an either-or type of scenario. Non-attachment doesn't just mean, well, like, you know, forget about it. Whatever the— wherever the money lands is actually like, if you think of money as a fuel that you're talking about, there's actually a tremendous amount of power in what we're deploying capital for and what impact it's having on culture and society as well. So how do we build from a place that's enough with high agency, with an eye towards money, its realities, the capitalist system that we operate in. It's a both/and.

Yeah, I love that. And it makes so much sense, right? Is that it's really transcendent and clear. How do I include both of these points of view in a way that reconciles and feels good for me ultimately, right? Because Yes, money is not the end-all be-all. Money can't buy happiness, but a lack of money can buy a lot of misery, ultimately, right? Like money is optionality. And if I really am driven by impact and service, then having more money means I get to amplify that message.

Yeah, yeah. If you're driven, that's a big if, but yes, that's right. If you're driven from a place of enoughness and that there's a genuine connection to service, 'cause lots of money can also buy lots of unhappiness too. Too, as we both know really well. So yeah, it's how do we deepen into the relationship with this thing and dance with its nuances. So that's very much the path that feels like it's continuing to open up for me and for my work with clients. And what a gift too to work with folks that are, you know, when I set out and started coaching, I thought that I'd be doing work just at a certain stage or size based on my own experience. And I've ended up working with folks that have been way more successful than I have, and seeing these similar struggles has also been a gift for me. Oh, cool. Yeah, these are here too, no matter how high that first mountain goes, as you know. And how do we build from this focus on a way of being has become a central part of my practice and also the work that I do with folks. How is it that we can settle into instead of what it is that we're trying to do, the mission that we're trying to have. Instead, here and now, where are we operating from? What's driving it now? And not— don't flatten it. Oh, it's love, Mike. It's love here right now that's driving this. Oh yeah, there's love, but there's other stuff too.

Need for significance. I mean, right?

That's right.

It doesn't go away.

Yeah, it doesn't go away. It's— but it's here. So anyway, going back to your, your sense of abundance and wealth, it happens in the here and now. Our attention, our awareness is a big dimension of that too.

Yeah, I mean, and you're using a lot of language from the meditation practice. I wonder, you know, how you think about meditation now and as it relates to this work. And do you pull it into your work at all, or what does that look like?

Yeah, very much so. The training that I've received from these teachers is something that's just, it's hard to extricate. But I think about the path of waking up as a fundamentally different dimension from the path of healing our relationship with things like wealth or with money, or also with stuff that happened to us when we were younger. And again, again, so instead of like a one grid, I think of it as another two grid, right? This is the path of waking up shows us what is meditation. It can show us more about the nature of reality, our awareness, the way that we relate to individual moments in time. And also you can bypass a lot of shit if that's the only path that you're going down, which I did fundamentally. Like part of my awakening was doing a ton of waking up practice and seeing how uniquely broken I was, but then not having the skills or the tools to really interrogate that and welcome that back into the different aspects of my life. So anyway, the, the waking up is one dimension of the inner work, and another big dimension of the inner work is the cleaning up. It is the integrating, welcoming more and more parts of ourselves into loving awareness is a fundamental aspect of the work. And so that's the last thing I'll say is like, I still love the outer work. I still love having conversations about strategy and hiring and how do we go big and yeah, totally.

Let's go.

And, and if you're just looking to 10x your business, I'm probably not your guy. If you're— if you just want to do the inner work, the waking up and the cleaning up, there are amazing therapists and teachers who can help you on that path. It's really for me, the fascination is that the inner side connection of these two. How do we let it rip from a place of enough, from a place of here? And what is really fun is as we continue on that path of practice, and for me, I'll just say, like, things keep getting more and more fun and interesting. It's amazing. Like, what a gift.

Imagine there's a listener out there, as might be the case, that is like, oh shit, I've been building from a place of lack. I've been fueling with dirty fuel. Oh no. What would you tell that person?

Hmm. Seeing it as the first step, I'd say like, congratulations. And I mean that genuinely. Like, that falling apart that I had on the meditation retreat is one of the biggest gifts that I felt like I could have had. And then, you know, what I'd say is this is a developmental journey that we're on. You're not alone. You're not unique in your brokenness. This is something that many of us, I'd say most if not all founders grapple with at some point in their journey. And if you view it as a developmental journey, okay, cool. There's a suite of skills and mindsets and orientations that are available to take you from building from a dirty fuel to building from a place of enoughness. What a fun journey. I mean, it is an incredibly fun journey to go down. Doesn't mean it's always hunky-dory and peaceful and happy. Yeah, but it's—

we never promised you a rose garden.

No, no.

Yeah, yeah. And as you swear, it can be destabilizing, you know, as it was for you. But then the unfolding on the backside really is such a beautiful place of creation and enoughness and beauty that it's worth it.

Yeah, my— I had this really unique aspect of my journey where— so my wife and I had two kids pretty close to one another. They're two years apart. And this was early in the startup days, building from not enoughness. And it was go, go, go. And, you know, lay off people five days after your son is born. And then just two years ago, we had— we welcomed the third kiddo to our family, the baby of the family. And there's a seven-year gap between into. And in that 7 years, I've been completely turned inside out. And I get goosebumps now just talking about this. There's a— the capacity to— the capacity to— the difference in the experience of showing up for a little being between Derek of 10 years ago and Derek of now is Yeah, all of those moments of like, oh shit, they start to click in to feel like this is an incredible journey and path. And again, what a gift to be doing this, this type of thing or be able to do this type of thing. So I just say, going back to that, that founder who's like, oh shit, might be building from not enoughness, I'd say like, welcome to the ride. The views here are at times harrowing. And at times completely beautiful beyond ways you could ever imagine.

Oh, what a, what a great spot to land. And, uh, thank you so much for sharing your wisdom with us. This is, uh, this has been such a great conversation. Where can people find you? Where can they learn more about your work? And how they get— how can they get in touch?

Yeah, thanks. My, uh, my website's my name, derekhaswell.com. That's where I do my coaching work. I'm active on X or Twitter for those that are still hanging on. And I just say, reach out to me. You know, what I say to everybody is if the messages that I'm sending are ones that you find helpful, I might not be the right person to help you for any number of reasons, but I have a network of teachers and therapists and fellow coaches that might be a better fit for you on your journey. And I'm totally happy to be a resource to you.

Yeah, amazing. Well, thanks for being here.

Okay, thanks for having me.