Episode 28 | An Engineering Leader's Search for Meaning with Chad Fowler

Chad Fowler: One thing that people that aren't managers don't usually know is that the money doesn't actually change when you become a manager.

Eiso Kant: Yeah.

Chad Fowler: You don't get a raise when you, when you become a manager. But at a higher level, I, I realized, I, I did a bunch of thinking about, like, what I was striving toward. And that was that what I was really trying to accomplish wasn't getting money and it wasn't being promoted. It wasn't even really being in the room so much. It was being free. And that's how I think of money right now. You know, I'm in a privileged position to be able to say that, but I guess everyone who wants more money wants it because of some sort of freedom.

Speaker 3: Welcome to Developing Leadership - the Podcast for Engineering Leaders, where Eiso Kant and Jason Warner share their lessons on the ins and outs of managing software teams. Today, we went down a human behavior and leadership psychology rabbit hole with Twitter's favorite engineering leader, Chad Fowler. The guys spoke about authenticity and compassion, introverted leadership, buying freedom, and reflecting on mortality to help you lead a better life and be a better leader. As always, this episode comes with accompanying show notes, with a deep dive into the main topics, mental models and key moments from this episode. Find them at developingleadership.co and linked in the episode description.

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Eiso Kant: Hi, everyone. Welcome back to another episode of Developing Leadership. We have a special guest with us today, Chad Fowler. Chad is partner and CTO of BlueYard Capital, but most of us know him from his Twitter handle @chadfowler, where he has been, for quite a few years, already showing his wisdom related to engineering and engineering leadership to probably one of the largest audiences that exists out there. Before we dive into the podcast, Chad, how does it feel to have that responsibility in, in our space?

Chad Fowler: I didn't know I had it until now, so no, I'm afraid. [laughs] What do you mean, because I have a lot of Twitter followers?

Eiso Kant: Yeah. I mean, a lot of us know you, a lot of us have learned from the things you've shared.

Chad Fowler: Yeah, I ... It feels like I'm a politician. I felt like that for many years, actually. And I, I hate it. Because I noticed that I'm, I'm really careful about how I present myself, and I actively don't want to be careful about how I present myself. I want to be me. So, it sort of drives me crazy. I think I'm getting better at it. And, and one of my antidotes right now is, just be as ridiculous as possible. So, you know, if I don't know what to do, then it's nonsense. That's my superpower is nonsense. I got it from my grandfather.

Eiso Kant: So, that's actually a pretty good segment into, into a question I wanted to ask you, a topic I want to talk about today, which is how we show up as leaders and managers at work, and should everybody be a leader or manager?

Chad Fowler:  Oh, well, no, definitely not. And I think there are at least two reasons for that, or there's more. One is, if everyone becomes a manager, then no one does any work, you know, actually, the things we're trying to get done. But more importantly, not everyone's cut out to be a manager. And I mean that in terms of both skill set, and aptitude, which are not the same thing, and desire. And I think desire is the more important one. I hate being a manager, actually. I really hated it. I find it to be emotionally painful as an experience because I am someone who also strives to deeply empathize with people and, you know, I strive to be compassionate, in everything I do is like an intentional thing. And therefore, as a manager, I experienced the most emotional turmoil, out of any activity that I participate in in my life.

Not everyone wants to do that. I shouldn't actually, be a manager. I actually ... I got a management coach actually here. Here's the funny thing. I got this great management coach, his name is David Surrenda, wonderful guy. And he worked with me for a while. I don't know why I decided to get a management coach. I think I just knew something was wrong, you know. And so, what we ultimately figured out together is I should not ever be a manager again. That was my coaching. And it wasn't because I can't be good at it. Some people think I'm good at it. Not everyone. That wasn't like the Trump thing, where you're saying, you know, some people are saying I'm the best manager ever. Some people do actually think I'm good at it. Not everyone does. But it hurts. And people don't really recognize what the activity is.

So, like, I'm now some random programmer, really great programmer, loves the creativity, they got into the field because they love it. They don't think of management as, "hey, you're going to potentially hurt people's feelings full time from now on. And you're not gonna do programming anymore. You're going to hold people's egos and confidence in your hands, and you have the ability to set them back years by making the wrong move or saying the wrong thing. And you're gonna do a bunch of spreadsheets and you're gonna be at a bunch of meetings that you have to be in that you hate, but you can't, you can't decide you shouldn't do them because they're important. It's just like all the work that you don't want to do when you get into the field of software engineering is what you end up doing as a manager.

And then, you know, we don't really teach people, especially in the beginning, that, guess what, leading people is a discipline of its own. You know, software development, obviously, is. We all understand that. But most of us don't think when we start that, that there's a whole other skill set that we need to evolve, and improve on. And, like, for me, I think my first management job, I was absolutely unaware of that fact and I just thought, this is maybe even a truism or something that everyone would say, I just thought, "well, I'm being rewarded for being the best programmer on the team, or whatever, by being the one that gets to decide what we do now." But I was totally unprepared and I just, I sucked as a manager as a result. Really did. What was the question? Sorry. [laughs]

Eiso Kant: No, I'm, I'm ... Well, actually, the, the second part of the question, you already gave an example of, showing up as yourself to work into these discussions, right? you, you right now absolutely did. And I know it's a topic you have strong opinions about. And so, I'd love to hear a little bit about, you know, what do you observe in tech today and in engineering leadership? And what do you wish the, the world could look like?

Chad Fowler: Well, maybe this isn't even a tech-related thing, but it applies everywhere, and, and that is, you know ... So if you, if you go back to the original question, should everyone be a manager, and I was talking about how people feel like they're being rewarded for being a manager, but those of us who are managers of managers know that's not a reward, right? the question then becomes how do you explain to someone that you're not, not promoting them because you don't think they're good, but because you value what they're doing or, you know, that's not the only path for success. What I find is that my tendency, and I will say the tendency of most people, is to, like, hide some information unintentionally. Like, I've got this context in my head and I'm trying to figure out what do I say to this person so that they won't be offended and I can move on and, you know, not have to promote them?

And what I've tried to do over time is learn to convince myself to just externalize that context and let them see it. And it's probably a slippery slope because you don't want to externalize, you know, like every bit of risk in the business, for example, and send your team into a state of confusion and, and fear. But normally with situations like, like, you know, why I chose someone else to lead the team and not you, there's a really good, reason for it. Now, sometimes the reason is you are too valuable doing what you're doing, we love what you're doing, we want to find a way to reward you. And by the way, I know that you think that being a manager is some sort of sign of success, but it doesn't have to be let's talk about that, you know. You could just externalize all that stuff.

Sometimes, though, it is your personality puts people off and I think the team will leave if you become manager, you know. And, like, as I've aged, I have found that those conversations are the ones that I sort of look forward to the most, even though they feel icky. Because something good always comes out of those when you do it right, especially when you can truly share how you feel. And, you know, not like, like, it's, it's the point where you're trying to make excuses or you're trying not to say everything because you don't want to hurt someone's feelings, or you don't want to have the hard conversation, that's when you screw up and you do make them feel bad. So there is this, like, genuineness authenticity that if we could all interact with each other in a genuine, authentic way with compassion, then all of this stuff would be easier. And we wouldn't have, you know, these weird hierarchies that, that aren't necessary.

Jason Warner: I think you and I probably had very similar experiences in our own histories in this in that I did try to hide some of the negative feedback, and I say negative because that's how it's gonna be perceived by the person that I'd be giving it to, not how I was intending it, but that's a different . Conversation but, what I also found too was hard was when you're having the conversation about management is not a reward, it's a different job. But we use the word leadership. Leadership has connotations for people. There's also cultural differences too. If you go across the world, manager is a lot of times how people have associated advancement. In unions in America, that is true, although we're breaking from that a little bit now. We're compensating people otherwise.

It's very difficult for a set of people to maybe say "no, I'm not advancing because I'm not making manager or director or, VP in that way. Even if my salary continues to go up and I get a different title on the engineering side, I need to jump tracks to be perceived to be successful." That conversation is the harder one for me. Because it's, it's very difficult to actually get people to understand what the job is and how it's different. And in reality, how you might be advancing but failing, and eventually being removed from the . Business, if that we're going on that path. Whereas in this case here, you'd be advancing in a different way, salary continuing to increase, and you're likely having higher satisfaction in the job too. But there's a ... It's kind of a weird, a weird conversation to start having with folks.

Chad Fowler: Yeah. I, I like to talk about how bad management sucks with people, you know, people on my teams. And I don't try and do it like woe is me, but I try to share the stuff that's not fun. And that is part of the externalization of processing that, that I think can be helpful. Like, "okay, I've just gotten to this very nasty meeting, and I'm dealing with politics," you know. Like, paint the picture so people understand what the job is like and then, you know, the, the reason I think the, conversation is so hard, like you just said, though, is that even I who know management is not a reward, the reason that I keep becoming a manager, even later career like I am, is because it feels good to be recognized ...

Jason Warner: Yes.

Chad Fowler: ... like to be the one that saves the day, or the one that someone can trust. You know, there's this external signaling.

Jason Warner: Early in my career, what I saw, and I tried to break this when I was in, when I was in that responsible role, was there was this feeling of being in the room, that managers got or advanced leader, leaders got in a way. So they were, they were behind a curtain that others didn't get to see a lot, and there is this feeling that you got from that, an insight you got. 

And, you know, when I was running engineering teams, what I tried to do is I tried to bring engineers themselves into those conversations and into those rooms, because then the, one, the mystique got broken, you didn't have to advance through the, the management ranks to be inside those conversations, and realistically, the voices are needed in those rooms and they were just being excluded in the, in the other times. 

And that was one of those early moments for me when I started to feel that, like, why, why I sometimes wanted to be going on that path was to be recognized, to be in the room, to be in that club. And I realized, well, that's stupid, that's ... Because that's not what my job is actually about. You know, but that's kind of the carrot is it's weird.

Eiso Kant: Is this really about like, and I know we're, we're gonna kind of, we're putting each other on the couch here. Because this really doesn't have anything to do with the job, with the career. It has to do with, you know, what has for each of us being our, our internal motivation or driver that, that we've ended up with, right? If that's we want the external recognition versus someone else who, who absolutely doesn't want it but wants money or someone ... Like, I mean, probably the odds are that a lot of people who do end up in those management positions, we are looking, it's kind of self-selecting, we are looking for that, that external recognition. Because at the same time, I know a lot of people who are not at all looking for external recognition or who have realized kind of like you, Jason, and I like to think myself as well over the years, and probably you as well, Chad, is that once you've gotten it, you actually realize you never should have wanted it.

Chad Fowler: Yes.

Eiso Kant: It really doesn't matter, but we all have to first get it and then realize like "no, that's actually not what's important in life." And I'm curious, maybe for you, Chad, if you're willing to share, like, that journey for you. It's also because you've, you've got to be a public figure in tech, you've got to sit in rooms where you've had a lot of that recognition and now kind of at a later stage of your career. You know, what are some of the, the lessons and learnings that you wish you would have known when you were younger, that would have allowed you to skip some of those, let's call it self-development steps, not to get too psychological on the couch here. Yeah.

Chad Fowler: Well, every conversation with me will end up psychological on the couch, and at some point, we'll be talking about death too. That's part of my, my shtick. But, like my own mortality has to come up before the end of the podcast or the podcast didn't happen.

I, I don't know there was anything that I could tell myself that wouldn't be obvious. But I, I, I had to go through it, I guess, you know. I started my career, as a musician. So, you know, I jumped over into software development because I was interested in it. And I am a, like, painfully shy introvert. So the way I made it possible to function in the business world was to think of it like a role-playing game. And in a role-playing game, there are levels. You know, and this is probably sort of how most people end up thinking about their career, but I literally thought of it as a role-playing game. And even like skill trees and stuff that I could work out, you know.

And so, for a long time I was working toward an ultimate goal of, like, I'm gonna be CIO of a GE business or, you know, some like really corporate kind of goal, because that's the context I was in. And as I started rising through those ranks, I reset my sights on different things. And like, there's always something in the distance. And you're right, I am a public figure and, and that was actually an intentional choice, too, because I, I met some people. I went to the extreme programming immersion training that I convinced my company to, to pay to send a group of us. I think it was like, we were half the class at this, this thing. And, in the room were people like Kent Beck, Martin Fowler, like, you know, some of my, heroes at the time, people whose books I read. And after a week of being with them, I felt so much smarter than I did the week before, because I, I was exposed to them constantly and, you know, it's that sort of like the, the company you keep changes, your capabilities thing.

And so I decided, I've forgotten this, but a friend of mine who was with me reminded me at some point, I am going to be one of those people, because I think that's the only way I can spend all my time with them, and get to be at that level, you know, like mentally and intellectually. And so, that was now my, my sights. And, you know, at a certain point, I got to where I had written a couple of books, and one of them was quite successful for a software book, Rails Recipes, early on. And I was being invited to keynote at a bunch of conferences. And then, we sold a, a company to Microsoft and I got to do stuff like go to meetings with Bill Gates and Satya Nadella. You know, at that point, if you're a nerd who just got into programming, because it was something to do in between playing saxophone gigs, now I have won the game, there's nowhere else to go, right?

But there, you know, there it is. I could be a billionaire now or whatever. But, looking back, there has been no increase in happiness at any stage there. In fact, what I found is that the bigger the job and the bigger the, the team that I manage, or the, the higher stakes, the less happy I probably am in my free time, because I internalize all of the stress. And, and of course, as I said, if I'm managing large organizations, like every conflict between two people in the organization, I ended up carrying around and taking personally, hopefully not making people feel that but, you know, it, it tears me up. So, you know, there's this whole like hedonic treadmill concept that it, it doesn't really matter what happens externally and what your external success is, happiness is intrinsic. I've known that since before I started, but, but I just kept going nonetheless.

Eiso Kant: Jason, you've kind of, you've kind of followed a similar path and now both of you are investors. [laughs] how do you, to put you on the couch here, you recognize yourself?

Jason Warner: Chad and I ... The story is very similar, the details are different. But it's, it's literally the same. So, you know, most of my career was programmer, then I started as a manager, and I kind of got on the, I call it masks as opposed to you were talking about games. I was like, which mask am I putting on for which meeting, et cetera, et cetera. Painful introvert as well. And I've gotten good at that side of it weirdly over the years, but it's still no less draining to do it. 

And, you know, I was kind of going up the ranks and expecting myself to CTO at the, you know, I was at Heroku so I was expecting to work my way through and CTO at Salesforce at some point, or something like that, some other company that looked like that. And then, there was a, kind of like outside of the career, outside of the thought process there, existential thing, which was my son. And I've talked about this in the podcast before, bunch of kids with, I have three kids with special needs, and my son is autistic.

And there was a moment when we were, my wife and I were talking, we're trying to figure out will he, will he live on his own? And in that I took it upon myself thinking, "oh, if he's not gonna live on his own, we're not financially set in a way that would allow him to do this if we die." And there's a parenting moment inside there where we're just like, well, that has to be fixed. That, you know, I don't expect to die young, but at the same time, I got to fix this. And that was the first time I really became money, specifically money motivated. 

It wasn't about making, it wasn't about seeking out, like, ways of making money. It was like, no, I got to take a couple of swings that are going to be, it'll be about that. And that's where, you know, GitHub started down that path. And, you know, thankfully, my unique skill set allowed, et cetera, et cetera, we had that discussion before.

But then when that happened, and it would happen on the first real big swing on that one, then you start down another path of, well, that didn't ... I was happy with the outcome, I was happy to sit out and have the objective, but to Chad's point, like, I'm no more happy in this. I'm now CTO at GitHub, I've got the money in the bank because of the acquisition, there's a path at Microsoft to do a set of things. Chad and I have actually had this discussion a couple of times on that topic, too. But at the end of the day, that's not the life I really ever set out to live. You know, it was more of a, a path now that I had put myself on, because I thought I wanted those things. And, you know, you don't ... 

You find yourself at 40 years old saying, "what do I want to be when I grow up?" and you have to take stock. What am I good at? What do I like? Where do I get satisfaction from? What do people need on me from the industry? All that sort of stuff. And, you know, investor was a natural path for me from a lot of different reasons. One is it took me out of things I did not like to go do. I found myself as a good executive, but I also did not like to politic, which is a part of being a great executive, in my opinion, at a high corporate level. And also, when you're holding other people's emotions every day, it gets really tiring.

And that's what management managers do, specifically, as Chad mentioned a couple of times, and some executives are able to not carry other people's emotions around, I found that I wasn't. Maybe I could learn to just kind of dismiss that, but I'm not sure I could. But as an investor is an easy kind of adjunct to that work and still be involved in the industry. But even more than that, it was, well, "I'm not motivated by the money anymore, I'm not motivated by the career aspirations in terms of the title, one of those, but I'm still interested in helping people," which is the first step you get into management in the first place. 

That's why you typically, someone like Chad or myself, goes into management. So then I'm saying, "well, I want to, I want to do that aspect, I want to help people, but I no longer, I don't want to do it in that context." So you're looking for a different context. And investing is a really good context to do that because you can do it across, at the highest level, across a wide portfolio at the highest level so you can have a really wide-ranging impact. So, that's kind of my, my thought process for it.

Chad Fowler: Yeah, I feel like I get to be on every team we invest in, which I just, I love that. And now that I said that out loud, it sounds like some cheesy garbage that a VC would say. But, but I, I really feel like I'm on the team. And the thing that frustrates me the most is that I don't get to be on each team full time, because I get invested in the people and the problems they're trying to solve. I'm mentally invested, emotionally invested, you know. 

You were talking about money and, you know ... So, one thing that people that aren't managers don't usually know is that the money doesn't actually change when you become a manager.

Eiso Kant: Yeah.

Chad Fowler: You don't get a raise when you, when you become a manager. But at a higher level, I, I realized, I, I did a bunch of thinking about, like, what I was striving toward. Maybe, I think 13 years ago, I wrote, an article for PragProg about, about this. And that was that what I was really trying to accomplish wasn't, getting money, and it wasn't being promoted, it wasn't even really being in the room so much. It was being free. 

And, and that's how I think of money right now. You know, I'm in a privileged position to be able to say that, but I guess everyone who wants more money wants it because of some sort of freedom, ultimately, even those who ... Like I used to be quite poor. You weren't free to do much of anything, you know, if you don't have any money.

The same is true with management, though, I always felt like, you know, early on, if I could be in the room, then I would be free to do, take the path that I wanted to take. And the team, you know, the team and I could take that path. So, I think most of what I do, I try to center still around freedom. And, you know, being a VC now is a, is a good spot for that. Like Jason said, there's a lot of things that you do in a company that you don't have to do as a VC, a lot of icky things you don't have to do. Not there are no, there are no icky conversations to have, but it's not a daily part of the job, uh-

Jason Warner: And the different types of icky conversations too. And while they may still be emotional, it's different than being a manager who's, who's doing that.

Chad Fowler: Yeah, you're not like holding some while you are sort of holding a position of authority, but usually not during the icky conversations. It's usually that you're not yet holding that position you don't want to, you know.

Eiso Kant: It's, it's interesting because I spend time with a lot of engineering leaders and, and, and there is, there is this pattern that time and time again holds true, which is: the introvert who's decided to become an engineering leader. I see myself as well as, as like a deep introvert who, after being massively bullied in high school and things like this, decided to, like, go down a different path. 

And, and if we talk today about the qualities that people will say traditionally make a good leader versus traditionally make a good IC, we usually don't start from the fact of you were an introvert or are an introvert and are now putting yourself in a position. And it sounds like all of the things that, that we seek out, when we make the decision to put, put ourselves in the path of engineering leadership, turned out to be all the things that we learn and we all have to learn these lessons over and over again, are not the things we actually want. So, all of us are doing something that we realized years later that we have enjoyed, but didn't actually live up to the reasons why we ended up doing it.

Now we have the both of you who've gotten to a point of freedom, and I think freedom is, is the most important word and freedom to take care of your family, freedom to, to make decisions that you want. And you've left engineering leadership. And so, it's, it's interesting that, like ... And I know both of you are massively passionate about engineering and engineering leadership. How do you reconcile that?

Jason Warner: Chad, I can take this. I can start on this one.

Chad Fowler: Go ahead. I'm, I'm sure I have an answer too.

Jason Warner: Yeah. Our, our answers are probably going to differ too. I, I wouldn't have minded to do it again. But what I found in doing it was, Inside of an organization as it grows, the primary point of contention across the organization was the engineering team. And when things went well, they didn't recognize the engineering team. But when things are going poorly across the business, engineering became a focus. And we've talked about this before on the podcast, sales and engineering are actually very similar organizations in terms of the way they, their sizes, the scales, the scopes, what they do, all that sort of stuff. And it's weird because they are way opposite engines of spectrums.

But I found that being an engineering leader was one of the worst, one of the worst positions inside an organization. And it didn't seem that the industry really was going in a different direction. I'm not sure I really want to pull myself up for that anymore. Not that it was terrible. We're well compensated, et cetera, et cetera. I can go through all the different ways in which it's a good job. 

But when you can opt out of doing it, sometimes you do. And the final thought on this one is that ... Again, I found myself in a unique position given it was, it was GitHub and stuff. And Chad and I worked together after the acquisition a little bit on GitHub things too. My wife was adamant that she wanted me to take some time away from engineering leadership.

She said, the only job I'll allow you to take, allow me to take, but you get what I mean by this, is for the family, would be to go CEO because I know you want to go do that. But even so, we got to set parameters in place. I would prefer you not do that for a while if you want to go do that because of the family situation. We want you to stay closer to home, more time, et cetera, et cetera. I know how all-consuming work gets for you. But don't do it again for the CTO or even CPO job. You've done that. You don't have anything else to prove. You're trading time with family for things that just basically are gonna aggravate you at the end of the day. Don't do it. I'm asking you not to do that. In this one other context, I would understand and I'd be supportive. I would prefer it not be right now, but, but, but later.

Chad Fowler: Yeah. It's funny, you're talking about something else to prove, and there you go again. You don't need to prove anything, right? Whether it be CEO or president of a country or, you know, who cares? It's, it's ego. And if I get back into it, it's gonna be an ego-based mistake again, which I've made, you know, the last few times. 

The first time, it wasn't an ego-based mistake because I didn't know what I was doing. You know, I just said "okay, cool." Where's my raise? Oh, no raise. Okay. But you know, it was, it felt good. Now I recognize it because since I've decided never to be a manager again, I've done it like three or four times, and it's always because it feels good, there's some sort of external recognition. Maybe it looks good on my resume, but I don't care about my resume anymore, you know. So, like, it's a nice title on my Twitter bio. You know, you don't need it, Jason. You don't need to be CEO of anything. You don't even need your, your existing credentials, actually, right? So it's this weird thing of, of how we project ourselves into the world.

Jason Warner: Yeah.

Chad Fowler: The way that I, I reconcile getting out of all this stuff, to answer your question, Eiso, is I'm not getting out of engineering. You know, I'm partner and the CTO at BlueYard and the CTO part, I joke every time I mention it. It's a somewhat new thing. I don't know what that means to be CTO at a VC firm. But I know it means I'm the best programmer, and so I'm gonna do some of that, you know. 

What am I gonna program? Probably not actually work on products or anything, but I'm staying deep in technology, and I'm getting to do it in a way where ... You know, the, the position that we're in as VCs now, and technical people, we meet geniuses. And, you know, at companies, you might work with a genius or two, sometimes, but now we meet them quite frequently. and, you know, people who, they're either literally brilliant geniuses, you know, of, of amazing intelligence, or they're just people so deep in a field that I, I will never be deep in, that I get to, you know, ask questions.

Like, we have one investment in a company called Chemify that is creating a computer to generate molecules. I'm, I'm completely clueless about any of that. But, well, now I'm less clueless, you know. But before that, I never would have even considered that's possible. So, it's I'm, like, both expanding my, my exposure to technology and still getting to do, like, pair programming with people when I want to, because I'm free to do that.

Eiso Kant: So, we went way. I think this is probably the most deep we've gone on any of our episodes. And so, since we're down, since we're down this path, I'm just gonna keep trucking down it. It's a first for us. 

I had a, a very good friend of mine, very successful, technical founder, sold two companies, by all means and standards, massively recognizable, and, I, I won't say anything that identifies him. We speak about every three to four weeks. And he, he came with a lot of the, a lot of the same things that you were saying, Jason, the weight that it feels to take care of family and the, the notion of, you know, our, our credentials, do they matter? But he said something to me, which I really like. He said they do two things in their family. He says, " I write my own obituary every year, and we look at the actuarial tables."

The first one I could understand, the second one, it took ... I, I didn't understand at first. I said, "why do you look at the actuary tables?" He says "well when I look at the actuary tables, my other family member who's older than me, significantly older than me, has a much better chance of living all the way to 80-something than myself. Because I'm at 40-something and I still have a lot of years ahead of me, and according to the actuary tables, the chances of dying are a lot, a lot higher because my, my scary years are still ahead of me.

First of all, very interesting way to think about, about data related to death, I never had in, in that context. And he does this exercise where he writes his own obituary. And I'm curious, when, when you've built up, you know, these credentials, but at the same time, are, are saying it's not what matters to you, what is it ... And let me start with you, Chad, and, and I'm sorry for going so deep today. What is it that you, you wish they might write, and, and would say when it's not about the, the credentials of the VC and then Microsoft and wunderkind and things like this?

Chad Fowler: Yeah, well, thank you for going ahead and talking about my own death so I-

Eiso Kant: You opened, you opened the door. So when you opened the door, I was like ...

Chad Fowler: ... we're 

Eiso Kant: going down it. Yeah.

Chad Fowler: Okay, I'm going to answer your question, but, I also ... Before I answer it specifically, I want to say that I love this approach that your friend has. I don't have exactly the same approach, like I'm not thinking about data. But to me, the best grounding, piece of information you're gonna hold on to is the fact that you are mortal. And, you know, I like to say at this point, I'm 48 so I'm, I'm on the back half of my life. I jokingly like to say I'm now in the dying part. And it, it changes how I think about things. It even changes, you know, like, do I need to have more aspirations? I don't know, I'm dying. It doesn't matter, you know. Relative to the age of the Earth, I'm already dead. I've never existed, you know, relatively speaking. So, like impermanence and insignificance are, are good, like, grounding things to hold on to all the time for me.

what I hope that people would write about me or say about me or whatever is that, I was compassionate and helpful, in situations where it wasn't necessary for me to do so and didn't necessarily bring me any gain. And I can even remember, like, the first time I wrote a book, I had written a couple of chapters of books before, you know, when people asked me to contribute one chapter in this or that. And I was asked to write my first full book. And those chapters were so painful to write, because I'm a procrastinator, and I don't trust my work well enough, you know, so I just, I feel bad that I haven't delivered, blah, blah. So I knew writing a whole book would be an absolutely painful experience.

And I had a talk with myself and said okay. What I was writing was a book on career development for developers. And, I said, "if I can dramatically improve one person's life with the hours I put into writing this book, then it's worth it. If the goal is just to write a book, then I shouldn't do it because it's not gonna be worth it. But if one person reads this and it has an impact, then it's worth having done it, because you don't make a lot of money writing books, you know, for software developers, unless you're really, really lucky. So, that has been, how I've tried to, to prioritize my, my work and my interactions with people at work ever since then.

Jason Warner: My dad died when he was 58 going on 59, couple cancers and stuff. So, when I'm getting ... I'm 45 myself, so closer to that than I really feel comfortable being. And it's, it kind of, it hits me more and more, obviously, as I, as the years go by and stuff too. But we, we don't think about that enough, in my opinion. We don't, we don't think ... Not that you have to think about death, but just understand that your time is the limit. That's effectively of what you're doing is trading time, either with your family, yourself, or your freedoms for things and other, or money or, or other activities. So, that, that to me is really important, like, you know, with my wife conversation that we have on a regular basis.

So we don't do the obituary, but we do something similar, which is we do the 20-year arcs with the five-year periods and the accomplishments we want to have with our families and professionally and personally. I've talked about that on Twitter a couple of times. 

Myself, when I break this down, I always tell people that I have basically two goals in life, which are I want to be married to my wife for the rest of my life and I want my kids to be, to come home, want to come home and come over for . The holidays or visits or whatever when they have the freedoms to not do that. Which means it's a very intentional construction on that. And then everything past that has to be in support of those two objectives. So you will understand how that would influence that. And those parameters helped me quite a bit.

Because at the end of the day, if I was going to maybe take the exercise to write the obituary, and when you asked that question, the first thing I thought about was I actually don't care about anyone other than my wife and my kids, really, at the end of the day, because I want to know what they would write about me. And I would hope that they would write about me as a person and as a father, as a husband, but also, they would be the projections of what other people would write about and how generous I was or how helpful I was, and all that sort of stuff. And I would hope that, that they would have learned stuff from me in that way, or it influenced how they live their lives and wanted to achieve that. Again, those are the hopes.

But if I did extend it out to other folks, it would simply be the one thing I would hope that people would say is I was a genuine person, I acted and felt genuine to them too. I was just helpful, like maybe aspirationally how I think about my time as a VC, but in general as a person is I'm the, I'm the best use of someone's time. Because we just talked about time being the primary mechanism by which we have to, measure life. But if I can give them as much possible information in 30 minutes more so than anybody else that they've ever encountered, I have just unlocked for them more time with the shortest amount of time occupying them. And that's generally how I view myself as a professional human these days.

Chad Fowler: You know, what you just said about time is my biggest fear as a VC. Anytime I have a meeting with someone, I'm, I'm terrified that I'm wasting their time.

Jason Warner: Yep.

Chad Fowler: That's a really good one. And what you, you also said, trading time for stuff, for money, you, you don't want to also forget that sometimes you're trading time for like chasing some sort of drug-like, you know, recognition or, or whatever it is, where you're just being recognized and, and being seen as being the coolest or the best or the smartest, you know, some of our careers and, and therefore, moments of our lives are wasted on that too.

Jason Warner: There's that old saying, I think it's from ... It's a song or a movie, but it's, you know, work people don't like to buy things you don't need to whatever it is, you know. I feel like we're gonna have to use the word privilege in this case here because I grew up ... Chad and I talked about this. Chad and I have a lot of history together, a lot of mutual friends, we talked about this, but we both grew up very similar and very, very poor, all that sort of stuff. So, once you, you escape that, you have these, these moments of extreme privilege to say like, you don't have to do that anymore. 

But when you're in those moments, it feels inescapable because you, you have no agency, you have no freedoms, you have no whatever, and so it's ... But once you're able to do that, some of us don't take stock. I knew I didn't for a long time. I didn't take stock. I always thought like I was ... I've talked about this before, I was always afraid of going back to the farm. I was always afraid of it. And, you know, it's never going to be that way. And even still, to this day, it pops into my head. It's like, "oh, shit, you're going back to the farm."

Chad Fowler: Yeah. And, you know, the other way to look at that is, and probably anyone listening to this podcast can ask themselves this question. You have found this freedom that you have now, whatever level of it is, is this really what you're gonna waste it on? You know, I like to ask myself that quite frequently. And I think that is a, a, a great grounding question.

Eiso Kant: Chad, I think this is, I think this is the question to leave everyone with today because I, I feel that we, we definitely need you back on because there's hours more to, to discover here. But, I think that's a, a fantastic place to leave today. Thank you so much for being with us. This was fantastic.

Chad Fowler: Thank you. I sure enjoyed it.

Jason Warner: Thanks for coming, Chad. It's been fun.