The hard power of management and the soft power of senior ICs | Josh Wills

So the hard power of management is the hiring. It is the promotion process. It's literally money, more or less like money and status and title and stuff. That is the hard power that is bestowed upon you by the powers that be that you kind of get by virtue of organizational positioning. That's the hard power of management. The soft power of being an IC is generally, especially in engineering IC, is knowledge. Is you know where the bodies are buried?

You have the context on the system. You know why things are the way they are. You kind of know what needs to be done. I think the extent that I had like a superpower, I have the ability, you know, this is not just, you need to meet a lot of senior ICs do this. You can see around corners, kind of what's coming and what's going to happen as the result of things.

Welcome to the Software Misadventures podcast. We are your hosts, Ronak and Guang. As engineers, we are interested in not just the technologies but the people and the stories behind them. So on this show, we try to scratch our own edge by sitting down with engineers, founders and investors to chat about their path, lessons they have learned and of course the misadventures along the way.

Hi everyone, it's Guang here. We're super excited to chat with Josh Willis. He's been doing data science and engineering before it was cool and has amazing wireless on Twitter. In this conversation, we explore Josh's journey into management and back to IC, comparing the pros and cons of the hard power of management versus the soft power of senior IC. His time working in Climentech and how he got started with Android investing without a ton of cash.

Without further ado, let's get into the conversation. Thanks so much for coming on the show, Josh. Thanks so much for having me guys. Okay, so getting started, you have a lot of amazing quotes. One of my favorite is your commentary on management. You said engineering management is a pie eating contest where first price is more pie. So I slack, you made a transition from director of data engineering back to IC. Do you remember the exact moment when you were like, yo, this is

way too much pie for me? I think I was sitting in a sprint review, I think I was sitting in a like a sprint planning meeting, kind of organizing the next couple of weeks of work and stuff like that. And I was just like, I hate this with every fiber of my being. And I don't want to do this anymore. I think, you know, back in up a little bit slack had a pretty regular practice of people going into management and then going back out again. I think

there was something that was like totally okay. Lots of people did it. My like my manager was a guy in Richard Crowley who like read the ops team for a while and was managing me for like when I first not not when I first started, but like pretty soon after in the first kind of major reorg. And I remember being on a one-on-one with him and he told me he was leaving management to go do I see work again. I was like, wait, you can do that. That's an option. Oh, that's interesting.

And I think that kind of like open Pandora's box for me, I think, I was like, oh, I don't have to do this anymore. If I really like don't like it or would be happier doing other things. So that was clue one. Clujoo was we used to do, you know, engineer, I'm sure they still do, like quarterly engineering all hands.

And Cal Henderson who's the CTO had this really great habit of gathering up all kinds of random statistics of like things people did over the quarter and things we launched and other like funny stuff too, right? All kinds of really interesting stuff. And on one of them, he was showing who had sort of written the most code and who had done the most code reviews and GitHub over the past quarter or so. And I was number three on the largest number of code reviews done.

When you were still the director. When I was still the director. I was number three on this list. And it was kind of like I think you couldn't actually see like where the next director was. Like they were so that you know so much further down the list compared to you know, it's a time when like I had a few hundred engineers. And like I was number three and it was like, well, that's that's probably not great.

Like probably I'm not doing something correctly here. So yeah, it was I guess it was a lot of signs and a lot of opportunities. But really it was that it was that's brain review. I was like, I just can't I just can't do this anymore that kind of put the nail in the coffin for me. Yeah. Do you know are there people that have transitioned to IC and then was like, oh, actually, you know what? Like let me go back to management.

Like going from management to IC and then maybe after a year they realize, hey, actually maybe management is better. Oh, they want to go back. That's interesting. I'm trying to think of anyone I know who's done that. I don't know anyone personally who has done that. So that means everyone that decides to go back is like, you know what, actually management was maybe the side route that IC is where they should have.

Yeah, I mean, I think there's there's a bunch of different things with that. I mean, I think we, you know, when we talk about this kind of stuff, we have talked a lot about psychology and everyone is like the hero of their own story. You know what I mean? Everyone has a narrative they are trying to live up to from somewhere, right? And for a lot of people being VP of engineering or CTO or whatever is a big part of that narrative, it's kind of part of their own personal heroes arc.

I used to work for a guy named Jeff Hammerbacher and he was great about sort of talking about everyone has a hero's arc and kind of understanding their hero's arc and figuring out where does what you need them to do fit into their overall hero narrative. And if it's not a fit, then great, you need to find somebody else who where it is a fit, right? Every role, every job, every opportunity is the right next thing.

For someone and a lot of it is just finding who that person is and sort of aligning their story with what you need and all that kind of stuff, right? So I guess what I commonly see, I mean, I don't know, I see a few different patterns here. For a lot of people like going into management is like the thing. It is what they, it is the latter. They've been climbing ladders their whole lives from like grade school to honors programs to good college to graduate school, blah, blah, blah.

It's a ladder and they climb ladders. That's like what they do. When I say this hypothetical person, I'm basically talking about myself here, right, just to be honest with you, right? And then once they get up that ladder, they are determined to do whatever it takes to make it to the next wrong of that ladder. Just because it's a ladder and again, climbing ladders is what they do. And it can be very difficult, I think, to get out of that mentality and be like,

I don't like where this ladder is taking me. The quote about pie eating contest where first prize is more pie. That's actually a description for law school. That's why I first heard that quote, people go to law school and the first prize at law school is the pie that contest where there's more pie, right? And it really is. I think that's another sort of, it's another one of these ladders people climb of like, I'm going to be a lawyer.

I've wanted to be a lawyer since I was a little kid. I'm good at arguing. I'm going to be a lawyer no matter what. I'm going to do whatever it takes. And then they discover 10, 20 years later that they hate their lives and that like everything sucks and they have all these problems as a result of it, right? So for all of these reasons, being fortunate, I think to have the self-awareness, to have friends, to have family, to have mentors, to have people who can be honest with you and say,

why are you doing this thing that you hate? Is this really something that is so core to your identity as a person that you have to do it anyway? Is truly like a gift and it's something that, yeah, I was very fortunate to have. So like for you, I guess understanding or hearing that story from your manager being like, oh, hey, this is a possibility, right? Yeah.

And I was pretty big. But was there anything else that like what was going through your head when you were like deciding, hey, maybe part of my identity as being this like director? Is maybe not the best fit for me. Like, what was that like? I really, it felt like uncomfortable, you know, it felt it was a strange thing to feel. I think to kind of not really answer the question directly, but maybe give sort of more context on what about me made me easier, that made this easier for me.

I think, I think it was a few different things. I mean, one, I think I've always been, you know, like the quote I am most famous for is the data scientist thing, right? And who's better at statistics than any software engineer and blah, blah, blah, blah, all that stuff, right? And I have always kind of leaned into that in the sense of like, I don't really think of myself as a particularly good software engineer.

And I'm definitely not like a very good statistician. All I really was the guy in the room who was better at statistics than any of the software engineers and better at software engineering than any of the statisticians.

And so I've always had this very kind of like, I'm sort of okay being a mediocre software engineer, I guess, or like just being, I'm okay at this. I'm not like, I've worked with people who are world class at it, and I can kind of admire how good they are at it, but I'm not one of them, right?

And I think that kind of mentality or sort of sense of identity that was not rooted in what my title is or how many people work for me or any of these other kind of ladder centric external status validation things that make your parents happy or blah, blah, blah. And kind of again, put me in a position to not really sweat this stuff so much, just to be honest with you, not really have to worry about these things as much as someone else.

So much so that I really was in a position to just kind of focus very directly on waking up every day, am I happy doing this? Am I enjoying my life or do I am I super unhappy? Am I gaining weight? Am I drinking too much? Am I like kind of miserable all the time? I'm like, what could be going on here, right? And yeah, that's sort of part of why, you know. It's hard, man. It's hard. I think, you know, you see this letting go, this is not easy to do.

And the only really like sort of thing I can recommend is to say, which a bunch of other people said before, it's a cliche, and it's a cliche because it's true. It's like when you get the thing that you thought you wanted, it isn't going to make you happy. It really isn't like not even close. It doesn't work that way. Whatever the thing is, it's not Jim Carrey has that great quote. I hope everyone becomes rich and famous and gets all the things they want.

So they find out that it's not the thing. Becoming VP,ventionary isn't the thing. Becoming CEO isn't the thing. Becoming River wealthy isn't the thing. There's no thing doesn't, doesn't exist. Be happy with what you do every day. It's a very least. The extent which you can just be happy every day, I think that's a very worthwhile goal. Be happy and be free. Absolutely. That's the best thing I've come up with in my 45-ish years.

I think that's on point. Any person I know so far, I've seen various transitions from I see do management, like people who were never a manager before, but weren't becoming a manager, I want to be a manager. Some of them switched back to an IC role. I've not seen any of them go back to being a manager. I spoke with some of them about this too. You had this fancy title, why go back?

The response was similar to yours. In some cases, what I came away with some of the Sanchez was, someone has to be comfortable with making the decision, not just being self aware is important, knowing that they want happiness is important. But the other part is, they have to get that title once to know it's not the thing that they want.

You have to do that once. It's true. You have to self-expedance it, no matter what the other person is going to tell you, unless it's your own experience, you're not going to feel it. That's so true. With my son, who's eight, I confront this problem literally every day of the, how do I convince this person to not make this terrible decision that they're about to make without actually having the experience of eating too much candy or playing too many video games, like all these kinds of things.

How do I get this across? You're exactly right, man. There's no substitute for painful experience to learn these lessons. I want to talk a little bit. I don't want to hate on management the entire time. We're here. Managers are great. Managers are great. I would say, good engineering management done well is absolutely invaluable. It is something I have a tremendous appreciation for having done the work and know how hard it is.

Paul Gramrod and SA, many years ago, describing the impact of different places on your mentality and he was talking about how in New York, the hidden question behind everything is, why aren't you wealthier? Why don't you have more money? In Cambridge, Massachusetts, where Harvard is, it was like, why aren't you smarter? Why aren't you doing something more intellectually challenging?

He said that the question at the heart of San Francisco in Silicon Valley is actually power. Why aren't you more powerful? That's actually what we care about out here. We care about his power. Those clowns in DC also care about power, but they're just not as good at it as we are. Real power is the ability to reshape how things are done and change the way people live and the way people work and stuff like that. That's real power and that is the power of technology.

Engineering management comes with sort of a set of institutionally derived sources of power and the most important of those by far is hiring. Hiring is everything. Hiring is the most important job. Again, I'm going to quote Jeff Hammerbacher again, I could just do that sort of throughout the interview.

Jeff told me when I started managing people at Cladera, that management comes down to, if you hire the right people and you motivate them properly, like you align again, they're heroes narrative with what you need done, you can do everything else wrong and you will still be a successful manager. I like to think that I was sort of the living embodiment of that principle.

I did those two things right and literally everything else wrong. That would not yet, I was still kind of okay basically in managing. The impact you can have on the culture, on people's lives, whose careers, all this kind of stuff is just so, so huge because of hiring. Hiring is just everything. It's the most important thing by far. I loved hiring. Hiring was by far my favorite part of the job. I loved meeting people. I loved learning about their stories.

I loved figuring out how those stories intersected with where we were at and what we needed and stuff. I found that tremendously satisfying, just tremendous source of joy for me. I still feel a sense of responsibility. I literally was talking to a woman yesterday who worked for me at Slack. I was talking to her literally yesterday about some problems she's having and her new job and her new place is a much more senior engineer than she was when I first started working with her.

We're talking through, this is the situation, what do we need to do here, what are the questions that ask all that kind of stuff. I love that stuff. I love those relationships. Relationships are everything around this stuff too. It's really is. The workforce is a very tiny village running to the same people all the time. It's all this kind of stuff. The relationships are everything. It's a cliche thing to say.

It's a phenomenal opportunity to create and forge great relationships with people that you love and care for much longer than even the few years you work together. It's fantastic. I'm grateful for that experience. So engineering management definitely has this human aspect to it where you need to match your needs to their heroes arc, for example.

You mentioned some managers are really amazing. Apart from being good at hiring, what are some of the other qualities you think that make some managers great versus others? Emotional intelligence without a doubt. One of the reasons Stanford has been so successful at producing so many phenomenal entrepreneurs and technologists and leaders and stuff has been.

They have a course there that I think is, it's got a proper name but everyone just calls it Touchy Feely. It's sort of a course on emotional intelligence. It's like this slang term for it is Touchy Feely. There's a course for that that grad students go through or under grad students go through? It's a course for the, I believe it is graduate students go through. It's it it look it up actually it is an option. It is the secret sauce.

I think of a lot of different folks who have who you've seen being very successful who've come from Stanford graduate programs is yeah, it's Touchy Feely is like focusing on that emotional intelligence aspect. Just the ability to read people the ability to like think through how the things you say impact them emotionally and stuff like I'll be able to deliver bad news in a kind and caring way. All of these kinds of skills.

I joke that every sufficiently high paid position in any organization is a therapist basically like for kind of all like the CEO is a therapist, VP Vengeance. These are all fundamentally therapy jobs right and I think the VP Vengeance Slack when I was there was Michael Lopp who writes under the, we say pseudonym or nom de plume or whatever we would call it like Rans Rans Rans in reposes his blog and stuff.

And he is just by far one of the most emotionally intelligent human beings I've ever come across in my life. And I think one thing I guess another sort of thing I commonly see Rans came up through engineering management on through QA through managing quality assurance teams like that was his he was came up through QA.

And you say wow it's actually not surprising at all to me that the most successful engineering managers and leaders come up managing one of the hardest teams in a company to manage and sort of grow and understand there is a lot of work. Understand there is a relatively low status profession at least it was for a long time in a lot of fields right.

So being able to be successful and thrive in that context and like help humans flourish and stuff and grow in the way they want to in that context is like a forge that makes you into a great engineering leader that takes kind of the raw material of your emotional intelligence. And that's what I think is really a lot of the things that I think is really important to me is to have a lot of people who know this stuff and know it to look for.

So whenever I see people kind of in these career situations that have to choose between managing like a low status team or a high status team. I generally recommend if I think they have the capability to do it going for the low status team because it will challenge you and make you grow that much more. Every engineering team has its set of problems. If you talk to any engineering team at Slack they would tell you why their team had the hardest problems at Slack.

Either executive leadership isn't paying any attention to you or executive leadership is paying way too much attention. There's no happy place like there really isn't everyone has their own set of problems. Everyone thinks their problems are the worst. There's all of them wrong. Obviously data engineering is the hardest by far. We all know that. Buying a sample size here in a way that I appreciate. But nonetheless, yeah. That's just the name of the game.

So for EQ, that's something that I think for a lot of engineers kind of struggle a bit with. Other than the super wars, how do you do things something that you can give it over time and like how do you get better at it? I do think some people are naturally good at it. Perfectly honest with you. I think of my own therapist. I worked with her on the order of 13 years.

He was just literally just the most empathetic person I ever encountered in my life. He sort of oozed empathy. I don't really ask to describe it. Studies were basically asked people to look at a picture of someone's eyes, like just their eyes, and figure out how they're feeling. And there are people who score off the charts on this kind of stuff. They can just look at someone's eyes and tell you if they're happy or they're scared or upset or they're trying to hide something.

Like all this kind of stuff. These micro expressions. I think I tried that and I did not. I did not. I do think there is a certain innate ability or something or whatever, some aspect of your experience that kind of leashes away. I do think courses like Touchy Feeley are designed to bring out this capacity. Just the same way you can teach someone to be better at public speaking.

Some people are naturally free. I don't have a reason to be better at public speaking, but anyone can improve at these things. Especially in that middle curve. When you're hanging out in the middle, there's a lot of really low hanging fruit. A lot of easy slope. You can just go pretty quickly by making a conscious effort to get better. The stuff, even if you don't have the inborn knack for reading people and stuff like that.

And then going a little bit back on the hiring. I'm a bit surprised to hear that. It's your favorite. The managers that I've had, usually they kind of dread just looking at the calendars of all the screens that they have to do. So I love that you mentioned the relationships, right? Which is super true in that sort of you carry throughout your career, not just at that job. So maybe more specifically on the technical stuff, how do you actually go about doing interviews?

I remember for me, one of my favorite interview formats that we're experimenting with with this mock code review interview, where we instead of doing the standard lead code, we actually have them look at a piece of code that we sort of, while isolated, such that there's not a whole lot of import that you have to explain to them.

But then you have them go through, maybe you'll like implement this and like very simple like mistakes, right? And then just kind of be like, just go through it and then tell me like, right, like, do it as if you were just doing a normal poor request. Code review or something. Yeah, exactly. And then just like write comments and tell me, yeah. Yeah, I have done this sort of style of interviews and stuff before and I like them a lot. I find them like very effective.

I think I've talked about this at least, I feel like I've talked about this at least somewhere before. I haven't done it publicly. We did at Slack, we did coding exercises, like we did like a take home kind of thing, which was the style of the time. I think it's, I don't actually know how people interview anymore. I haven't like worked in a while.

So I've not done a proper job interview and like even longer than that. At the time, it was something that I felt like we could kind of get away with, I think, because we were Slack. You know, we could like say, oh, here you have to do this take home to come talk to us and stuff. And some people were so excited to work there.

I think that's, it's a harder sell for like, especially when you're trying to hire people who have kids and stuff like, like if you gave me a take home now and was like, hey, Josh, do this take home before you. Like not so much. No, thank you. But like, but in any case, yeah. So we gave it take home coding exercise. I think it's okay. I don't think they use it anymore. At least Scott, I hope that hope Slack doesn't use it anymore.

I developed it off of the the Enron email data set was the Enron email data set, which is a famous data set, like a big collection of emails and stuff, right? And so I had the person do a kind of bunch of different data claint, dany cleaning data prep data modeling data structure things written in whatever coding language they like do it all in SQL, do it all in Java Python, whatever.

I don't really care and answer a few different questions basically about it. And I generally cared about the quality that I looked for at least in data people and maybe I look for kind of into a fault, I think in all engineers is conscientiousness.

In the same way that you are mindful of the fact that even though this is a coding exercise that's a throw up for the interview, I am going to be reading this. And so like things are sort of thoughtfully laid out. There are like a style has been imposed is not just kind of chaos with like a bunch of stuff randomly commented and things and dense and all kinds of weird lines and stuff like that.

That was really the like behavioral attribute that I looked for and stuff like that in data people was this sort of sense of conscientiousness. I've been just like steeped fortunate so many folks I've worked with have gone on to do like great things. It's just anyway.

That attention I guess to detail and also sort of the empathy of having someone who's reading this like actually knows what's going on. Like did you like find that kind of translating well into like when they're actually working together they're like being a lot just like better teammates instead of just being really trying to focus on getting their stuff done without

getting their stuff done that's a great that's a great point and I think I feel like the answer would have been yes if I'd been a good enough manager or going to have leader to allow that to happen because I think what happens too often and on small teams like I think the core data team I manage for a while was like four people and it took us we had super hard time hiring for any number of reasons.

So I got to meet a lot of people the problem is that if you're doing data stuff the surface area that you have to cover is essentially the entire company and so like if your data team is is roughly the size of like more or less 1% of the company you just don't have anywhere near enough capacity to have people really working together and stuff.

What I would say is that like even as I spread all of these these my data engineers out kind of among the company people really liked working with them and they formed good relationships with the growth team the platform team the infrastructure teams and like all this kind of stuff so I think it did contribute in that way but again I just like as I regret as I look back on things I regret mistakes I made really just not focusing the entire team on like one sort of problem to me like just to say like look everybody listen I know we got platform problems.

I know we got customer success problems I know I got a research problems but look growth is the most important thing right now growth is the most important thing in the company we are all going to do growth everything we're going to do we're going to do for growth and I feel bad I have to say no to literally everyone else at the company right now who you need data for things but this is the most important thing this is what we're going to do to the exclusion of all else and I didn't do that I was too busy trying to make everybody happy and of course in doing so I made no one happy in the process again a very classic very happy.

Very normal very predictable you know early engineering managers mistake yeah in our email exchanges you mentioned something about the the hard power of management versus like the soft power of the like a senior I see up and I see yeah yeah can you tell us more about that yeah for sure so the hard power of management is the hiring it is the promotion process it's literally money more of us like money and status and title and stuff that is the hard power that is bestowed upon you by the power of the company.

That you kind of get by virtue of organizational positioning that's the hard power of management the soft power of being an I see is general especially in engineering I see is knowledge is you know where the bodies are buried you have the context on the system you know why things are the way they are you kind of know what needs to be done I think the extent that I had like a superpower or still perhaps have a superpower I'm not sure I have an exercise in a while I

because of where I worked in the things I've done I have the ability and this is not just unique to me a lot of senior I see is do this you can see around corners kind of what's coming and what's going to happen as the result of things and again great engineering managers can do this too and in different very different

class of problems right so I was really good at slack and at we've grid which is where I worked the climate tech company I worked at which I'm sure we'll talk about a little bit at proposing things relatively early on that seemed like relatively low stakes minor decisions that I could just kind of get a quick consensus on the end

and I ended up having kind of dramatic profound long term impact on the company and sort of how things were done like how work happened at slack and we've grid and stuff like that and that was that is sort of my secret joy when I talk about like everyone in Silicon Valley is obsessed with power and people make this engineering I see sort of trade off right as they go from kind of the implicit power of knowledge of seeing around corners and all that kind of stuff that I see have and that's sort of the power they provide

and they transition to the hard power of management and they find they aren't as good at wielding it I think as they thought they might be and that they kind of miss they miss the power they miss the feeling they miss the work of being an I see and that's what pushes them back and that's why you don't generally see them go back the other way is they sort of know they know what power is available to management and they know it's not really for them

John Carmack at a great quote about this other day like you talk a lot of the stuff around like AI's and LLM's and how does that shift the balance of power in these ways and stuff John Carmack was talking about how he is deeply uncomfortable with the power of management he doesn't like it it's not a kind of power he feels comfortable wielding he much prefers the power of being

John Carmack of being basically one of the best software engineers to have ever lived and that's the kind of thing he likes to wield and that's that's the sort of place that provides them the most satisfaction most agency most sense of mastery all the good things all the things that again contribute to happiness and thriving and all that good stuff yeah so it's like one example would be like say like implementing like RFC process right like that's

something that it's very especially like these early are on in like the growth of the company you can like oh everybody said oh yeah that's a good idea and then but then like that really has like a profound impact in terms of exactly and if you're good at it if you're good at these

sort of decisions are basically invisible no one the people taking for granted is just the way it's done right I like to the joke of being a senior or early IC early engineer in any successful company you get to make an enormous number of decisions and the vast majority of decisions are good

decisions because if they weren't good decisions the company probably like what have failed right so you make almost all decisions correctly their good decisions and they're invisible no one can see them and also because you're a person and you're human you're flawed you make a you know small

number of like really bad decisions kind of like a bunch of things were like I you just you just got it wrong and those decisions inflict pain and suffering on everyone forever and everyone hates you for them and all this kind of stuff and that's like congratulations

that's the prize also you get a lot of stock so hopefully that's that's fingers crossed yeah but yeah but that's the nature of it that's the nature of the job that's what you're signing up for right right I remember at the first company I worked at it was really small I started and it was it was my

first job so remember and there's still around so it's like after four or five years they're saying this sort of really stupid process that they had to go through it I was like oh yeah remember that I'm sorry guys yeah yeah definitely

absolutely absolutely absolutely does and again this the great stuff you see no one sees that it is like like of course it works that way how else would it work actually actually like no that was a really good decision I made like it's very important like anyway people

remember you for the wrong decisions that you made for sure they absolutely absolutely no no no no whenever comes and says hey this thing has been running just fine or the decision was pretty cool because we didn't have to go back and reverted yes utterly utterly invisible utterly invisible no one appreciates it again and you know again to your point same thing with engineering management good engineering management is invisible and what is it you people do here right and you can only be

appreciated by experiencing a lot of really bad engineering management and understanding like wow good engineering management is like you guys are doing a really good job of not fucking this thing up for everyone that's good congratulations good work everybody you know easier you know easier set them done easier set them done it's hard hard to do yeah okay so I hate to do these like two part questions but they're kind of related sometimes in the way yeah okay yeah please don't

hate on me around it's fun it's fun so why do you like do you recommend then like every engineer to at least try management and then the second thing is sort of like shit I forgot the second plate great yeah let's just go over the first part I think everybody I think it would be a good thing if everybody who wanted to do management or was curious about management had an opportunity to do it I very much do and I mean I think that's generally

true I think if you want to for instance manage an intern or something like that which is like in many ways like the lowest stakes form of engineering management that opportunity should be available to everybody like kind of with without a doubt right pretty much anywhere you go everywhere so much of the opportunity to do that I think you if you are curious about this stuff if you think it is something you might ever do for any reason if it's something

you'd like to understand better like all of these kinds of things I think it's worthwhile I also think in like I sort of have met people who were just very clearly engineering managers even when they were ICs they could not help themselves they were obviously engineering managers they had engineering manager written kind of all of them in everything they did and how they approach problems and how they did things it was just unambiguous

clear they were going to be an engineering manager and potentially a very good one someday yes did they know that at the time because I feel like right for engineers a lot of time the skill set is pretty different

in my life for example like EQ right you know it's not it's highly okay I'm getting so I mean you're right I think again I think if they if they do have the EQ level it's kind of a cliche to say they can generally clearly clearly indict tell that they have a higher EQ than the people around them

but let's just stipulate that something people who have high EQ are good at right just by nature of total logically like like being good at EQ and you can tell so I think there's certainly a I think they're aware of that fact I think I think the tricky thing and this can be like a very engineering culture specific kind of thing I think at Google I think it was hard to be a pure EQ manager because of how highly Google arguably to a fault kind of prioritize this technical excellence

and I've used the term like technical pyrotechnics which is kind of a redundant sort of phrase but you need some sort of level of like pretty serious technical credibility as an engineering I see to progress up the engineering ladder at Google just because of like all those senior I see as we

talked about who were like again are there because of their technical prowess need to respect your opinions need to like be willing to listen to you and stuff and so you need some like pretty serious technical credit under your belt in order to do that and I think that is often I think the hard

thing for those people to sort of keep in mind is to say look yes you were good at this like yes you have the knack for it yes you will very clearly you will very clearly be doing this this is destined for you right for better or worse because again it's not an easy job carrying other people's

emotional burdens and all these kind of things it's not like it's not an easy thing to do even for a high EQ person but you should be sure to build yourself up as technically as you can because that will provide a foundation for you that will pay off your entire career without a doubt anyway and

that's and that can be tricky because again their inclination is that way they start taking on more engineering management you work especially if say hypothetically speaking they're not working for a super high EQ engineering manager and that's not good that's your hand like you're

really can you caping yourself when you do that sort of thing you're holding yourself back yeah anyway everyone's got a different set of challenges right this is just the set of things I've seen in my in my life and times yeah I just don't add one thing to what Guam was asking or say like there's

a usual lap between what an engineering manager does and what a senior I see do does I think and there is there in my experience yes like stop that's not actually that's not actually necessarily true not in this country depends on the team depends on the company

depends on the company for sure at least in my experience I think there's a usual lap in terms of your involved in priority planning calibration performance reviews what you're not doing as a senior I see is giving people the bad news deciding how much they should get paid yeah

pretty much that I would say yeah I'd say it very much depends on the company I think like I you know but I love you but like you've been at LinkedIn for like six and a half years I think being LinkedIn for a long time has certainly colored your way to think the way LinkedIn does certain things

yeah no for sure yeah you know not true yeah I have one really one perspective to agree with yeah at some places yes that is very much the case at other places not so much not so much not so much I think at Slack engineering management was not generally involved in like technical

architecture decisions in any kind of meaningful way yeah it was not really was not there purview it really was the very much the senior I see in the council senior I see purview a lot of it and I would say the senior I see were less involved in like the promotion process

and like that kind of stuff and the planning process I see companies have different cultures a lot of you know Google very engineering driven like into a fault Slack was much more product driven like really it was product driven product kind of coordinating design engineering together

and in those and in those kinds of cultures I think engineering management is sort of more important because since product is really sort of thriving things forward right it's like that becomes a much more important relationship so I mean it really is yeah depends on the company yeah depends on the big part of it for you it's like what kind of engineering manager are you the more technical engineering manager or are you the more again high EQ politically astute all of this kind of stuff

again these are real things these are valuable skills and a lot of it is about finding the right company not just the right role but like the right company where your particular approach to these problems will be appreciated will be valued all all that kind of stuff yeah yeah that's true

I just got really excited because everybody's disagreeing I was like ooh that's good I mean that's the best that's really that's what you want I mean it's it's very if we're just saying about a green which others very boring podcast yeah thanks thanks thanks I do what I can

I mean I yeah I've had the experience of being the guy who's like well Google did it this way and therefore all companies should do it this way and like that's not you know deeply profoundly not true not even close yeah anyway no cool so after Slack in late 2020 you joined a climate tech start up

a call the weave tech which you've been sure we've great we've great yeah we will not cut that out you could say say raw things all the time okay part of the brand out apparently exactly so sorry so what they what they do is they build software to help the power grid

better adapt to changes in usage pattern as more people have EVs in their homes during this sort of search process yeah what was your search criteria like right I think you mentioned that this was like heavily impacted by like COVID and then you know like yeah

walk us through like how does sort of yeah late late 2020 kind of stuff right so yeah I mean I think I left Slack in at the very end of October 2019 and I was just deeply and profoundly fried and burned out I think I did I did the software engineering daily

podcasts like a month or so after I left I go back and listen to it about like just how like just how like super fucked up I was basically like I really I didn't touch a computer in anger at all in like four in four months I didn't do any coding and all that kind of stuff right and I was really sort of like out of loss I really like I was not thinking about like another job or any kind of role or doing anything with computers possibly ever again I wasn't really sure and then you

know COVID happened and COVID happened when COVID happened my friend DJ Battelle has done a bunch of cool stuff used to be the chief data scientist at LinkedIn used to be the deputy CTO of the United States is venture capital is now a great guy kind of gave me a call and he was like hey we're helping out the state of California with like pandemic response stuff we're working with these epidemiologists at Hopkins and the State Department of Public Health and they could use like some help

basically kind of running these like they've gone from running like little toy epidemiology models for fun you know or for like their students and like epidemiology 101 to running them for like the governor of California and like the president of the United States and they're under a little bit of stress and they could use them they could use some help so can you come help them and so I did so I did that for a few months and it was really it was the kind of thing where like my head

state was such that the only thing that could get me back programming and engineering essentially they're just gigantic data pipelines right to be honest with you right was a global pandemic emergency type situation and so fortunately unfortunately I was like I was sorry doing it again and it was

it was a profoundly great experience for me I loved love working on it and it was it was all the things it was like let's scale this stuff up let's identify the performance bottlenecks let's like fix them let's break them down let's run

stuff as fast as we can under under high pressure deadlines and y'all I loved it I loved it it was the best working experience of my life I think it was like one of the reasons I really like startups and I've primarily done startups for the last decade or so after Google is I just feel a tremendous

sense of joy when working with people who are all aligned towards the same goal in a very clear way like really before the big company inevitable politics and difference of opinions and visions and all this kind of stuff inevitably creeps up there's there are these moments early on when everyone

is rolling in the same direction and again you can find pockets of these things about any anywhere in any stage but it's just tremendously satisfying and that stuff for me that sort of March 2020 thing was amazing because it was cool to work government academia industry like everybody was very briefly because God love America very briefly rowing in the same direction we were all aligned on what needed to be done and that was that was really powerful and it was

a very special experience like we get together for like a little reunion like the sort of general crew of people who just like like about once a year or so and it's just it's just it's the happiest day of the year from the by-wide margin right so two things I mean the mission without a doubt obviously the mission the impact was profound and tremendous the other thing was like it was really nice to just be free of like Jira meetings really of any kind you know I was doing

this I was doing this as a volunteer like they wanted me to go to a meeting and I want to go I just wouldn't go what are they going to do fire me it's fine actually get shit done just get shit done just that was it that was the whole thing right and so anyway that experience very much influence what I was looking for next I think that and I think you know again 2020 like Jesus fucking Christ like fuck that year but um September 2020 I don't know if you

all remember you like in the Bay Area there was the day where the sun didn't rise and the sky was all scary scary scary ass day right that was terrible I remember like my son again who's like you know he would have been four at the time like wakes me up at seven and he's like he has a you know light in his room that goes off when it's when it's time to wake up or at least you know he did when he was a little kid and he said daddy it's it's seven but the the sun's not out yet

and I was like what and like you look at the sky and it's like basically like hell more like it's like the sun upon you right so all these kinds of things right I had been feeling for a while for a number of years I think a lot of people have felt that I should be doing something to help fight the good fight like against climate change as in whatever way I could and whatever way I could meanfully do that and that really kind of really drove it home for me was like

I want to you know this I suspect this will be a formative memory for my son when he is older and when he asked me when he's like 20 or something dad what were you doing you know when the sky turned orange I wanted to have a good answer for him so it was really those kind of things I was looking for something very small where I would have the same kind of freedom to execute and just crank that I had during the covid stuff because I'd never been at something truly

like that small before and I was looking for something in the climate space I was also I mean for better or worse I'm an investor like I am a VC in a hoodie like the I've been fortunate to work at cladera went public slack went public Google is still around and kicking and doing okay as far as

I can tell well my mind is the last two weeks but yes I love them so much they're just so hapless it just kills me anyway I've done okay basically I was like an investor like picking companies and so I got I do angel investing now and stuff and so invested in a lot of

data tech startups DBT most famously but mother duck materialized tabular bunch of different AI things like I've just I do a lot of angel investing and I I inspired myself trying to be cool and like looking me I'm in my hoodie and I'm an engineer and all that kind of stuff I am in many ways like an

investor and I look at these I look at opportunities as an investor and so I wanted to find something that was a real business so tiny team where I could execute hitting in the mission and was a real business that I felt like would actually do some good in sort of the climate

fight and we've great checked all those boxes for me it was only 10 people they had hired my friend Bo Cronin earlier in the year so I had like a good kind of connection there to an engineer I knew well and worked with and like just thought very highly of

and yeah it was it was the mission and it was it's an interesting mission I mean building and this is kind of a I guess I don't want to say way into this kind of stuff like how can tech help climate tech stuff people ask me this a lot because I've done this work and I obviously don't work there anymore I left last year and my honest answer that's kind of a bummer is that the if you want to have if you want to meaningfully impact climate change the best thing you can do is start

a company or go work at one of these very big high-paying tech jobs make a lot of money and pay your taxes it's such it's a bummer I know no one's going to write a folk song about you for doing this kind of thing but that is honestly the best way to help we have a lot of really smart people working on the climate problem I say having done the climate work for two years I am grateful I am so I am so much more optimistic I guess about climate change and our ability to handle

it than I was when I started doing this stuff back in 2020 because there are so many good smart decent mission oriented people like working on this kind of problem and so I'm not nearly as worried about I do worry about like we have a lot of infrastructure to pay for we have a lot of transformers to buy we have a lot of solar panels to build we have a lot of infrastructure we need to pay for and it's going to cost a lot of money and so that's being in a position to provide that

money is honestly again now I say it doesn't people don't find this very satisfying I can't totally relate to that because actually for me climate change got like personal it was like that exact moment and then so I spent like like a month trying to I was also sort of in-between jobs to try to figure out like okay if I can do something with like climate tech and then I mean what you said after like a month of like listening to a bunch of podcasts right

like doing research looking at like all the what the companies are doing and then the biggest conclusion I had was like I should have done like a materials engineering and then learn how to make that that's true you know it's funny you say that I work like one of the one of the folks that worked with the we've great actually is it was a physicist he's a PhD in physics from Berkeley and he did it to study a photovoltaics and build better solar panels and stuff

back in the hot and it was great when he got out and finished his PhD he discovered that it wasn't really a physics problem we actually solved with the physics problems what it really was was like a utility bureaucracy regulatory

nightmare like kind of problem of actually building this stuff and so that's what he does that's how he helps he's a PhD in physics he studied full so photovoltaics and like building solar panels and solar cells and stuff that's not the problem he works on the problem this is the problem right and

that's I don't know that that's like just super cool to me I mean that's that's absolutely tremendous I have you know like I really profoundly admire that stuff there aren't many like tech problems right honestly yeah there's nothing that like a better key value store or like an s3 backed post-gress engine these are all amazingly cool pieces technology they aren't like the core of the problem in climate change there's a few folks I think who are making a meaningful

difference there are some climate finance companies like kind of Fintech for climate financing is very interesting to me and I actually think is both a real business and material because again we really just need money to build all of this stuff that's really we know how to build it we know what we need to build we just need to build it that's the problem so the financing stuff I think is actually like quite interesting and it's an opportunity for leverage but again

it's not it's not the it's not AI it's not large language models it's not like we don't need rocket science you know super super hardcore tech stuff like that's that stuff is just kind of a side show it's really yeah we need money that's what's really what we need yeah so I wanted to give you a take maybe on two points so one is because right like I imagine maybe things would like or as the landscape changes in the future maybe things become different so like one is

like are there any tips like for other like engineers like maybe five years out that's doing the search of changing from like a traditional software engineering in the tech company to like is there anything like when you were doing the search that you like you were like oh this is very helpful and then the second thing maybe is actually yeah that just start with the first yeah it's good I mean the hardest problem my far is the network issue and again it's

kind of back to where talking about relationships and stuff like that right the most important thing for me joining we've grid was that I knew someone from the tech world who had joined we've grid and was there already that was a huge help right I think you see a lot of things especially like the recruiting industry and so they got even recruiting stuff for a long time in tech pivoting to doing recruiting recruiting for climate tech that is enormously helpful that is

tremendously helpful building these networks that allow us to cross over finding people you know who you like who you like to work with before who are doing this stuff now this is like most of the problem is like you come in you don't know anybody they don't know you how do you know if you're going to like working together right I mean they don't necessarily understand the technology stuff they're doing you don't understand the climate stuff they're doing this is a

problem like this is the big problem and again lots of people have made this leap and the more people who make it the better off we're going to be because the network will get richer and denser and all that kind of stuff and then ideally climate tech becomes the same sort of village right you see this kind of already there are already I would say like there's a company a few years ago called O power was eventually acquired by Oracle and went public and stuff like that

and it was the I think in many ways the first big successful climate tech traditional tech company right there was a bunch of hardware and solar and stuff like that right this was like a software company that made the leap and all those people are everywhere they're alumni are percolated all throughout the ecosystem much much in the way like some micro systems and like silicon graphics and all this kind of stuff this is how this happens and so you want

to join one of those kinds of companies and I think for what it's worth we've heard is one of those companies I think we've heard will be one of the companies that seeds the next generation builds the network and stuff like that

become the next like to your point the company's we don't know we need yet the ones we needed five years and stuff like that that's that's what I think I think at least for right now based on what you said earlier anyone who wants to get into climate tech I think mission driven being mission driven

would be the first filter like they can't go into it thinking what I'm going to do is start as technical problems yes that's not what we have them satisfaction if you go in hoping for that you're going to be I think sorely disappointed yeah again it's just it's just not it's not the issue

and it's a lot of people are trying to marry the two because it's sexy and it gets good press and it's just really deeply not the problem it's just it's not serious people doing that sorry hate to be a bummer here if you want to do LLM

stuff don't do LLM's for climate like for the love of God don't please it's a terrible idea just absolute nonsense yeah so one kind of a random question I had was yeah we're talking to Mitchell Hashimoto and then one of the things he said that really resonated with me was like the most

important attribute for engineers was like being practical and in your experience working in climate because there's so many people there because of the mission right not because of the money not because of like the technology do you ever like run to co-workers that are like a very

motivated driven but then they're also like less practical in terms of like compromising and like how do you and like how do you address like like how do you deal with that in those situations I mean not very well I guess it's like we're like thinking and reflecting on it yeah yeah

not very well I only really have patients these days for one junior engineer and that is my son my year old yeah there's a lot of this stuff it's a bummer I mean I first of all agree agree with Mitchell like it's he's right pragmatism there's the

quote I saw once for any given problem the question is like what is the simplest thing that could possibly work and why didn't you do that that's the sort of the two-bar question what is the simplest thing that could work and why didn't you do that and I try to be empathetic

because I was once that junior engineer who was again and really it was very important to me to like impress everyone with how smart I was and all this kind of stuff and like look at all this cool shit I can do like how awesome I am and stuff and getting over that has been

like the work of the last 20 years or so like more or less I wish I had higher EQ here guys I really do I wish I was better if this kind of stuff I do I just sit and I just sort of see but yeah I don't know yeah yourself aware I think that's that's pretty good EQ

it's good it's good to you but I need to get over the like the fury more like again people who are better this than I am can like get past the blind rage and like we're best at like we're best at judging the faults and others that we see ourselves right and so this is a fault I am all too

familiar with and and have a have a super hard time who has because it just reminds me of all of the terrible decisions I have made and the pain and suffering I've inflicted and stuff like that and that's it's a tough one for me man it's a tough one again why it's good to have that hiring power

you can screen for that it was like I think I have in my enraught email database I remember some I got a few submissions where like someone used like Neo for J like a graph database to solve it and I was like yeah no absolutely no like under no circumstances this is instant red flag me

the number one I was when I was interviewing insight data science people I would often see a lot of really nuts of technical architecture let me use every single thing that I possibly could to rebuild uber on top of Kafka or whatever and I was just like no no no no no no absolutely not thank you

next like that kind of stuff yeah sorry about that that's just we were so not really told us to use no I mean I anyway in many cases like why anyway you're you're mentioned of Kafka to mind me of some other discussion we were recently having it work and it's like just use my sequel until it doesn't

work just use my sequel one of my other like super favorite quotable instances was a tweet or a during the pandemic oh age this microservice could have been a sequel query oh yeah like you know like this meaning could have an email this microservice could have been a sequel

query yeah for sure like there's a lot of that stuff man a lot of stuff like that it just kills me so how do you filter for yeah practicality in engineers like doing the interview so other than okay so Neo4j for I think I think it's no no I mean the Neo4j thing isn't a particularly

egregious example I mean I do so I think every technical interview should include a software design component to it of like let's design a system let's build a system from scratch for doing something like it I don't know if I can tell you the one we used it we have

grad because we still use it or whatever but I want to see you design something I want to see how do you approach the problem design something I want to see the technology choices you make I want to see why you make this technology choices and that's yeah it's that's essentially how I

screen for this kind of stuff is this like what did you use and why that's what usually works pretty well not for nothing yeah so you mentioned investing I think this is kind of similar to investing in a way where okay well one how do you get into investing ah okay that was a hard

fear that I know that there's no the reason I'm asking that is one I wanted context on how you get into it because I'm interested I don't know a lot of money but I'm interested the second thing having a lot of money helps but yeah yeah I need a few more years and maybe a few

more startups which actually will public which we have and let's see jokes apart but like the reason I brought it up is in a way when you're hiring doing the interview you're looking for good engineering skills you you want to know the person knows what they're talking about being practical

as a aspect of it yes you're also seeing can you actually work with that person or not or do you lose your patience to quickly engine investing like once you invest for example and I I don't have any practical experience with it but from what I've heard from many other folks who have done it again

other part yes well in a way that's kind of a working relationship too like do you want to get a call with that person on a Saturday morning if they're running into problems and you would only do that if you actually like them

that's true kind of similar to hiding that that's why I asked the question that is somewhere I mean there's I think a lot of things that go into angel investing that are different than normal working relationship stuff I think I mean I guess obviously like much far fewer people do that kind of

thing right thinking of like qualities of an engineer that make them not great angel investors in general there are some like phenomenally good angel investors who are engineers but maybe not as many as you might think the hardest

one I think I guess the most common kind of failure pattern I've seen as engineering manager engineers wanted to become angel investors is they are too skeptical especially good ones are generally too pessimistic pessimism is a desirable trait in a very senior engineer you want people

who are thinking about what are all the things that can possibly go wrong absolutely these are good people to work with they are desirable co-workers they are not good angel investors because most startups are going to fail they are if you come in if you come in with the attitude of like well let's

like pick this thing apart and see all the ways it can fail yeah there's going to be like a million of them there isn't like a shortage of ways for the start up to fail it's probably going to happen you have to kind of reverse your mindset and your orientation to be what would have to happen for this thing to be massively successful for this to be like a billion dollar plus company this to be a very valuable very big deal transformative company what would have to happen

and is there can I foresee a remotely plausible path for that to happen so that's like that's a big shift it's a very different kind of way of thinking it's a yeah it's the positive goal of the very sort of negative characteristics

you have to like shift your mentality in that way that's a hard thing I got an angel messing because I did quote like due diligence that's what they so venture capital is call it due diligence is just like hey you engineer or whatever person talk to the founder of this company

hear about what they're building and tell me what you think about it is this something you would buy how much would you pay for it this is a real problem for you all these kinds of things right and generally you do this for free this is something this is not like a

when people run into problems getting an angel investing their first thing is like why should I do a bunch of free labor basically like why should I like do all this free labor to help these venture capital is make lots and lots of money this is a fair question they are going to make lots of money

you're not investing you're not going to make any money the only reason to do it really is if you kind of intrinsically find it interesting to think about technology and technology companies and like what sort of potential they can have is that something like you just you would just sort of enjoy that if you like did you read the book on like the rise and fall of uber or whatever like is it something you would do for fun and for me kind of tragically the answer is yes

I would literally do this for fun I enjoy it the reason I'm not a venture capitalist because I have an up close and personal perspective on like all of the shitty horrible aspects of that job but that aspect of it is super fun it is a fantastic hobby and I absolutely get how people get into venture

thinking that's all it is and it's like deeply not true but I get the appeal of that without a doubt right and so I did this for years for free just because I thought it was fun I sort of enjoyed thinking about it talking about that kind of stuff right that's how I got into it such that when you know at a point in the future when I did have money like when slack went public and stuff and I could become I could actually start investing I just asked those same venture capital

say I have some money now I'd like to be an angel of us or if I talk to a company you're investing in and I see and I like it I want to put some money in will you let me in the answer is of course they're absolutely happy to they're thrilled to have you it's like the very least they can do to pay back all of the years of free labor and stuff like that and the relationship that you've built with them over time and that's it that's kind of the whole game that's how I got into it

I don't recommend a different approach I guess broadly speaking so that's it that's kind of like thing one that's that's how to do it that's how to get started doing it that's a separate question from like how to be successful at it yes because again angel investing is a terrible idea and again this is one of those cliché and this is me giving you advice that's the opposite of me and blah blah blah how do you do it well yeah that's a harder one like it's a very difficult one

right the general consensus seems to be that almost all of the really really good investors you've ever come across or you've heard of or you know about or whatever had a deal early in their careers that hit in a major way and then it becomes kind of a becomes a sort of selection bias kind of thing

or like a hey we should let Josh into this deal because Josh was early at DBT and therefore Josh knows lots about data infrastructure and tooling and what's going to happen and stuff like that and you know I like to think I know a lot about data infrastructure and tooling and I can foresee where things go but like I'm also basically an idiot and I get lots and lots of things wrong right just because I happen to get one thing right doesn't mean I'm going to

like get anything right else right in the future like this is again is a significant luck element to this kind of stuff right like without a doubt possible for once it's not to be presented of the future perhaps the first is not much than a future returns and I think you know again

a lot of people if you get kind of higher near and supply and you think that like oh yes because I got this right I therefore know what's going to happen and that is like deeply not true whenever I run into investors who are like

that I just like give a very I roll yeah oh god I can't believe I have to talk to this idiot but for better or worse that is a thing and it's like having that early success and getting lucky I think just contributes massively to your deal flow and kind of everything that comes after that is

really ultimately I think like important to being a successful angel investor so this is kind of my this is my weird advice work for free for several years happen to have an exit to provide you enough money that you don't mind sending some of that on fire and then get really lucky early on

simple three-step process to become a successful angel investor easy for anyone to replicate right like it's just that's just insane lovely highlight you put that in yes no I think that's just like just terrible but again it's why this is basically a bad idea only do it again if it's important to

your identity like the reason I did it was because I wanted to be an angel it was really it I was willing to spend X thousands of dollars just like you call myself an angel investor I'm like because I'm into moron like I don't know I don't know I thought the other cool other cool engineers were doing it and I'm like okay I got to do it too because I got to be cool like them I mean I mean I think what's funny and great about Silicon Valley is the amount of

status that it crews I mean look at I mean look at Jason Calacanis for God's sake right like I mean has that dude done anything in his life besides being an early investor in Uber does he ever talk about anything else ever right it does seem to come up a lot right like you talked to me like DBT DBT like I mean again it's just at utter nonsense I actually like not for nothing all series is if you are serious about angel investing I highly recommend Jason Calacanis's book on angel

okay I for what is worth I very much wish I had read it before I had started because I just again as in my engineering mindset I look at him I think this is the useful person in the history of the world and yet somehow he has managed to do this and become like this very successful angel investor he must actually know something yeah that I don't know and it kind of turns out the answer is yes he does you can actually his advice is actually like really good and I like

I said wish I had read it ahead of time are they like two or three things that you remember from the book that they're super helpful one is he writes a lot about how do you make yourself useful to accompany early on right and that's that's how do you break into this kind of thing especially when you don't have any money like how did how was he useful to his first several angel investments when he didn't have that much money right how did he make himself useful what value

did he provide and this is an important thing for everyone to have who wants to get into you kind of have to have like a stick you have to have like a thing that is your thing that you are known for I think a lot of dev rel people which is effectively what I used to do a clad era would make great angel investors if they are generally much more optimistic than your average engineer they have the vision they have the network they have the knowledge they have reputation this

checks a lot of boxes like not for nothing I if there was I there are actually a few I think like firms that are basically all X dev rel people like doing best for your best thing and I'm like I'm largely bullish on these firms I think there's something to this I mean they know all the problems for sure because they're talking to the people who act because they're talking to the people who actually have the problems right and again but they yes I mean these are all

these are like good qualities I think right so you have to have a stick you have to have there's an angle there's a value you provide one of the ops like finance ops persons I worked with its lack started a venture fund for doing that for providing like early stage fractional CFO kind of style investing you can like anything you need to have like a thing that is your thing you are known for like a brand basically so new but like a cal canis is a marketing guy he's

really good at this stuff and his his perspective is useful so that's like thing one was very useful like how do you get into this what's your stick figure out what that is for you figure out how to get in second thing is like how do you limit the amount you're willing to wager like basically let's put our green visor accounting hat on here how much of your net worth should be invested in startups well it kind of depends on what you're trying to do like how much you

have to burn all the concept he has like a good discipline perspective on this as well that I was again super useful to me because like y'all 2021 was a hell of a drug like everyone was investing in everything is going crazy everyone was like telling every way everyone was successful so we're all

geniuses no matter what you invested in it was going up right and so be mindful about like okay how much money I actually wanted play here is I think a very very useful framing and something that's good for you to think about early

speaking obliquely vaguely from personal experience this is a good thing I wish I thought about it earlier so anyway for all these reasons I said I thought it was a good book I thought it was really useful yeah that's helpful I I recommended wholeheartedly yeah so in this case like you mentioned the

first advice you gave was well be useful and work for free where yeah do diligence how does one well I don't think an average engineer knows a bunch of we see is who would reach out to them for due diligence so how do you put yourself in a position where you could be helpful I got introduced to the first BC's I knew through cladera's venture capital relationships because I was a very I was a I was a not only Lisa cladera I was a senior director which again I had no

real report to me that I had a good title because DevRel didn't really exist this is a thing back then and I was doing a lot of customer facing stuff so I had a good title I don't know that I am very humble I think I'm a pretty amazing I think I'm a pretty I'm a pretty I make fun of myself I think I'm a pretty amazing engineer nothing like my wife makes fun of me for this she's like you only say you're an idiot but you also claim to be among the best in the world

at what you do and I'm like yes both of those things are simultaneously I agree I agree I am among the best in the world at what I do like with without a doubt I feel both of those things very deeply and so that introduced me to Jerry Chanek Graylock and then a ping and a bunch of folks at

Excel until I got and those are my first early kind of venture capital relationships few folks randomly just reached out to me it was sort of great a lot of early people who just started moving into venture will ping you and they still

they still ping me to this day early on they've just started as a as a principle or something like that at Adventure Capital firm and they're trying to build these relationships with people who have a presence of some kind through doing DevRel or whatever right so they'll reach out to you and ping

you I have to be honest I don't really accept those pings anymore I know I like say I know enough venture capitalists like I don't need to add any new ones I'm like I'm good like the ones I have I'm pretty happy but early on when I didn't know anybody I was more than happy to make those acquaintances and like half coffee with people and talk to them and stuff and that's that provided a foundation for stuff like I was high you know we actually got introduced

to like like Mike Dobber and a lot of folks at Amplify who I work with and a lot of investments and stuff like that was just through like hey we're all hanging out together at a Giants game one day do you want to come just chill with a bunch of data people and some venture capitalists and I was like hell yeah it sounds like great fun that was a that was my idea fun before I kids I could just do things like that right so yeah once you establish some kind of public persona

again find your stick find the value you provide they will come and find you they're they really well it's they especially again those early stage folks who aren't yet partner they're just building their own brands they're building

things like some of the folks early on have made they've turned into like phenomenal investors who are very successful and I'm just grateful that I've gotten to know them for like so many years especially it's like you know getting to know somebody before they're a big deal right is super huge

and super important and when someone takes a chance on you before you're anyone for anyone cares who you are it feels much the same way it's like yeah it's a great thing yeah quick question I'm being like sort of having your own stick like yeah say in your case right like part of that is like your engineering like experience with the data infrastructure and stuff like that do you feel compelled then like as you're like I think your LinkedIn title is what like a kingfully unemployed data person

do you feel like oh yeah I need to be spending like how many hours like a week like working on like engineering problems such that I like like don't lose touch with sort of you know what's going on with the yeah I mean that's a good question that's a good question

I mean I do so I work and have worked for the last couple of years on the DBT adapter for duck DB and so the extent that I have like a stick online these days that's baked in this the data science of stuff but it's a lot of ducty-b stuff so ducty-b very cool embedded olact database

I kind of another thing that I sort of like caught on to early or as like this is very cool this could be a big deal I think this is a very neat interesting piece technology that could be very useful for people and so I am now sort of known for doing that stuff and I do I guess like I

it's kind of like brings back around to what we were saying earlier about like working with like cultivating taste and a sort of sense of simplicity and stuff like that I do generally find that hard and interesting engineering problems find me kind of no matter what I do people want to do new and interesting things with DBT duck DB a lot of my portfolio companies ping me when they say Josh we've got this

we're thinking working on this problem and we're sort of starting to suspect that we're going to need to build like a custom database or something like that to solve it and I'm like great let's just talk you down from that cliff like we're just talking

a call like we'll work through that and we'll figure out like why post-cress is actually the right answer for you right they they find me I don't feel the need to go seek them out I guess for what it's worth and not really doing anything they still seem to find me okay I'm very

fortunate I guess is that fortunate I'm disposing this is a good thing right this is okay yeah doesn't really bother me yeah okay so on the engine investing topic last question there yeah what do you look for when you decide to invest in a company

like I'm sure you're saying no to a lot of them too but what are some of the signals you're looking for when you say yes oh I mean so there's a few basic things I need one of two things to be true it was kind of a prerequisite to have the conversation one is that this is a person I know

very well and I've worked with before and I would back them if they were doing like a cupcake shop like I don't really care like anything they want to do even if I don't understand it even if I don't agree with it it kind of doesn't matter I know them they're really smart they'll figure it out either either either even if I think the idea is bad what happens if like you you find a really good team or a team you know well

and you think they're awesome and they're working on something where you're like this is a terrible idea and no one should do this either you're wrong and they're right and that's that's a very good thing or they're super smart and they'll figure it out pretty quickly and pivot to work on something useful and so I have run into this problem a few different times where like really like the team but didn't invest in the idea

because I thought it was a bad idea and inevitably inevitably they think inevitably either I am wrong or they figure it out and they go on to be massively successful and so that's kind of thing one I think too is if it's got to be kind of pretty specific to data tooling or something

LME AIE where I feel like I know something or I have like some information advantage the bummer of like like on my LinkedIn profile I don't advertise myself as an angel investor because I don't want I still get spam for people who like oh I saw you're an angel investor

or I listened to this podcast and stuff like that right and that's another reason not to do things like this right and inevitably again yes yeah it's I should have my head examined no inevitably inevitably I get paying by suffer people like I literally know background in what you're building

whatsoever like you're doing some consumer thing or you're doing something for like security teams or dev and I just like I don't know anything here I have no special information advantage that makes me any different and if I don't feel like I know something but if I cannot dilute myself into thinking that I understand a market well I just don't invest in it I just put it all in total market index funds and bonds the way every other saying rational person does right make that's much much simpler

so yeah either person I like have a strong relationship with doing something that doesn't matter or it's something where I feel like my expertise gives me some insight or perspective on the market how the buyer thinks and then at that point it's fairly easy it's basically like would I buy this

if I was running a data team at company X right what I purchased this would I pay money for this and if the answer is yes then you invest and if the answer is no you don't and that's fine and then I mean again I think if I could just put a call out there if I could just if I had a nickel

for every time some engineers have pinged me with an idea for some kind of cost saving thing for data teams I just please don't do that like it's just those ideas are just so bad and I know you say to yourself well if we could just save the team's 10% of their time

think of all the money we would make think of all the value we create I'm like just no no no no no no no no and cares about that doesn't matter don't do that do things that make people money yeah do things that this don't yeah don't start it just again it can work sometimes

but just nine times out of 10 99 times out of 100 making companies money is the way to go don't try to save companies make them money that's what they want they want to make money it's like the personal financing right like don't worry about spending

yes just increase your total income just increase your revenue right it's the like it's like I'm building a budgeting app for data teams or something I'm just like no terrible idea it's never work I know I know it feels like a good idea I understand how you feel

I get it I've been there it's really bad ideas it's just not going to work and so then I spend a lot of time on the call just trying to talk them out of it and then trying to talk them into building something that I want which rarely ever works but I'm just going to kind of

keep at it because it's way easier than starting and how many is like tricking someone else into working like that so that's really much much much you know great financial returns and a lot less emotional damage so yeah smart choice smart choice thank you I

appreciate that thank you I I spent like I did like a little startup like incubator program and then so I did not spending seven eight months like building out this platform to say cost sorry you're a vice I wish I would have listened to what you said just

now because yeah that's very real I mean like like so many things like so many things these things have to be experienced personally I've never I've never successfully convinced anyone with this pitch by the way so it's like again like so many things in this be it engineering management or becoming a senior IC or all these kind of things there's no substitute tragic tragic that may be for having the paint experience learning you'll experience learning is just tough to be a no amount of wisdom or

podcasts or anything will ever change was ever thus human condition yeah you want condition yes or the it's the it's the what's the the I love the rest of development joke where it's like it's what Tobias and Lindsay and like saying you know they'll did it work for those people no it never works for them but it might work for us these people to leave themselves and yeah yeah this is so fantastic of a court anyway sure that's true well whatever optimism yeah well Josh this has been

an incredible conversation plus went to what Guang said both of us have learned a lot was fine like I said it's I like I like getting to talk about the engineering management stuff because I've just I've always wanted to talk about it in depth and I haven't had

it before so yeah thanks for the opportunity yeah thanks so much thanks so much thanks so much bye bye pleasure hey thank you so much for listening to the show you can subscribe wherever you get your podcasts and learn more about us at software miss adventures dot com you can also write to us at hello at software miss adventures dot com we would love to hear from you until next time take care