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

Episode Date: March 19, 2024

As a self-described “gainfully unemployed data person”, Josh Wills is an angel investor and has worked on and led data teams at Slack, Cloudera, WeaveGrid and Google. We discuss: How to get started with angel investing without a ton of $$ Attributes that define great engineering managers What’s it like transitioning from management back to IC Challenges in Climate Tech from a software perspective And more   Segments: [0:01:35] Transitioning from management to individual contributor (IC). [0:10:19] Emotional intelligence and its role in engineering management. [0:25:21] Contrasting the hard power of management with the soft power of senior individual contributors. [0:37:18] Addressing challenges in climate technology. [0:51:34] The importance of practicality and how to assess it in interviews. [0:56:01] Josh's journey into angel investing. [1:12:59] Criteria used by Josh to evaluate whether to invest in a startup.   Show Notes: Josh on Twitter: https://twitter.com/josh_wills The “Touchy Feely” course at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics Jason Calacanis’s book on angel investing: https://www.amazon.com/Angel-Invest-Technology-Startups-Timeless-Investor/dp/0062560700   Stay in touch: 👋 Make Ronak’s day by leaving us a review and let us know who we should talk to next! [e-mail]

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 an engineering IC, is knowledge. 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 to the extent that I have a superpower, I have the ability, and this is not just unique to me. A lot of senior ICs do this. You can see around corners kind of what's coming and what's going to happen as a result of things. Welcome to the Software Misadventures podcast. We are your hosts, Ronak and Gwan.

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've learned, and of course, the misadventures along the way. Hi everyone, it's Guang here. We're super excited to chat with Josh Wills. He's been doing data science and engineering before it was cool and has amazing one-liners 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 a senior IC. His time working in climate tech and how he got started with angel 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 prize is more pie. So at Slack, you made the 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 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, backing 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 named Richard Crowley who like read the ops team

for a while. And was he was managing me for like when I first, 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 IC work again. And I was like, wait, you can do that? That's an option. Oh, that's interesting. And I think that kind of like opened Pandora's box for me. I think it 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. Clue two was we used to do, you know, engineering, 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 in GitHub over the past quarter or so. And I was number three on the largest number of code reviews done. This was when you were still the director. When I was 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, you know, so much further down the list compared to, you know, it was a time when like Slack 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 we say there was a lot of signs and a lot of opportunities, but really it was that, it was that sprint review where I was like, I just can't do this anymore.

That kind of put the nail in the coffin for me. Interesting. Do you know, are there people that have transitioned to IC and then was like, oh, actually, you know what? Let me go back to management. Going from management to IC and then maybe after a year, they realize, hey, actually, maybe management is better. And then they decide to go back. That 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 I see is where they should have. Yeah. I mean, I think 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 to talk a lot about psychology. And everyone is like the hero of their own story. You know what I mean? Everyone 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. So I guess what I commonly see, I mean, I don't know, I guess 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 ladder. 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. And when I say this, 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 rung 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 contests where first prize is more pie, that's actually a description for law school. That's where I first heard that quote. People go to law school and the first prize at law school is a pie in the contest where there's more pie. And it really is. And 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, like, 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 i imagine that 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 director is maybe not the best fit for me? What was that like? I really, it felt uncomfortable. 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 this easier for me, I think it was a few different things. I mean, one, I think

I've always been, you know, like the quote I'm most famous for is the data scientist thing, right? Someone who's better at statistics than any software engineer and 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, make your parents happy or blah, blah, blah. 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? Gee, what could this be? Like what could be going on here? Right. And yeah, that's sort of part of why, you know, um, it's, it's hard, man. It's hard. I think, you know, you see this letting go of this is not easy to do. Like, and the only like, really like sort of thing I can recommend is to say, which a bunch of other people have 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 of engineering isn't the thing. Becoming CEO isn't the thing. Becoming uber wealthy isn't the thing. There's no thing doesn't there doesn't exist. Be happy with what you 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. Yeah. I think that's on point. Any person I know so far, I've seen various transitions from IC to management.

Like people who were never a manager before but wanted to become a manager is like, 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. And I spoke with some of them about this too. Hey, you had this fancy title, why go back? And the response was similar to yours.

And in some cases, at least what I came away with some of the answers was someone has to be comfortable with making this decision not just that 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 like you have to do that once and it's true yeah it's like you have to self-experience it no matter what the other person's going to tell you. It's like, unless it's your own experience, you're not going to feel it. I mean, that's, that's so true. And again, with my son, who's eight, I confront this problem literally every day of the, like, how do I convince this person to not make this terrible decision that they're about to make without actually having the

experience of, you know, eating too much candy or, you know, like playing too many video games, like all these kinds of things. How do I like get this across? And yeah, you're exactly right, man. There's no substitute for painful experience to learn these lessons. There just isn't. And I think since we're, I want to talk a little bit, I don't want to like just hate on management the entire time, you know, we're here and that's not my goal. Managers are great. And just, I would say good engineering management done well is absolutely invaluable. And it is something I have a tremendous appreciation for, having done the work and know kind of how hard it is. I think about, you know, it's funny.

I think Paul Graham read an essay, you know, many years ago describing, like, the impact of different places on your mentality. And he was talking about how in New York, the kind of the sort of hidden question behind everything is why aren't you wealthier? Why don't you have more money? Right. And in Cambridge, Massachusetts, where Harvard is, it was like, why aren't you smarter? Why aren't you doing something more intellectually challenging? And he said that the question at the heart of San Francisco and Silicon Valley is, is actually power. Why aren't you more powerful? That's actually what we care about out here. What we care about is power. And those clowns in DC also care about power, but they're just like kind of not as good at it as we are.

Real power is the ability to reshape how things are done and like 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 Cloudera that management comes down to if you hire the right people and you motivate them properly, like you align again, their heroes

narrative with what you need done, you can do everything else wrong and you will still be a successful manager. And I, 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. And that when I, and yet I was still kind of okay, basically in managing, right. The impact you can have on the culture, on people's lives, people's careers, like 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. And that's, and I loved, I loved hiring. I did like hiring was by far the, 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 like where we were at and what we needed and stuff i found that tremendously satisfying just a tremendous source of joy for me and i still feel a you know sense of responsibility and care i like literally was talking to like a woman yesterday who worked for me at Slack. I was talking to her like literally yesterday about some problems she's having at her new job and her new place as a much, much more senior engineer than she was when I first started working with her. And we're like talking through, okay, this is the situation. Like, what do we need to do here? What are the questions to ask? All that kind of stuff. And I love that stuff. I love those relationships. Relationships are everything around this stuff too. It's really is like the workforce is a very

tiny village running to the same people all the time. And like all it's all this kind of stuff, right? The relationships are everything. It's again, a cliche thing to say, but it there's a, it's a phenomenal opportunity to create and forge great relationships with people that you love and care for, for much, much longer than even the even the few years you work together. Yeah, that 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, do you think,

that make some managers great versus others? I mean, emotional intelligence, without a doubt. One of the reasons I think 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 i don't it's

like the slang term for it is touchy feely okay there's a course for that that grad students go through or undergrad students it's a course for the i believe it is graduate students go through graduate students go through yeah we're looking 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 it's 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 of engineering. These are all fundamentally therapy jobs, right? And I think the VP of engineering at Slack when I was there was Michael Lopp, who writes under the, what is it, would we say pseudonym or nom de plume or whatever we would call it, like RANS. RANS and Repose is 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 through QA, through managing quality assurance teams. Like that was his, he came up through engineering management through QA, through managing quality assurance teams. He 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 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, all these kinds of things, and really like lets you demonstrate like what you are truly capable of

in a way that I think other people who know this stuff and know what to look for. So whenever I see people kind of in these career situations, we 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 than it. 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 to you. Way too much attention to you, right? There's no happy place. Like there really isn't. Everyone has their own set of problems. Everyone thinks their problems are the worst. Of course, all of them are wrong.

Obviously, data engineering is the hardest by far. We all know that. Amen. Biased sample size here, but in a way that I appreciate. But nonetheless, nonetheless yeah that's just the name of the game yeah so for eq right that's something that i think for a lot of us engineers kind of struggle a bit with so other than the course how do you do you think it's something that you can get better over time and like how how do you get better at it? Oh, I do think some people are naturally good at it. Perfectly honest with you. Like I think of my own therapist, like a guy I worked with for like on the order of 13

years, uh, he was just literally just the most empathetic person I like ever encountered in my life. And he, he sort of oozed empathy. I don't really know how else to describe it. Um, they do studies, like, I don't know if they to describe it. They do studies where basically they ask people to look at a picture of just someone's eyes, like just their eyes, and figure out how they're feeling. And there are people who score kind of 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 they're upset

or they're trying to hide something, like all this kind of stuff, like these micro-expressions. Yeah, I think I tried that and it did not, I did not. It didn't. Okay. Got it. Exactly. So I do think there is a certain like innate ability or something or whatever, some aspect of your experience that kind of leads you this way. I do think courses like touchy feely are designed to bring out this capacity just in the same way you can teach someone to be better at public speaking. Some people are, again, just naturally for any number of reasons, better at public speaking, but anyone can improve at these things. And especially like kind of in that middle curve, right? When you're like hanging out in the middle, there's a lot of like really low hanging

fruit, a lot of easy slope. You can just go pretty quickly by like making a conscious effort to get better at this stuff, even if you don't have the inborn knack for reading people and stuff like that. Yeah. And then going a little bit back on the hiring. So I'm a bit surprised to hear that it's your favorite because like the managers I've had, right, 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, so the relationships, right, which is super true. And that's sort of you carry throughout your career, just at that job so maybe more specifically on the technical stuff like how do you actually go about doing interviews um i remember for me one of my favorite interview formats that we're like experimenting with with this like mock code review interview where we

instead of right like just doing the standard code, we actually have them sort of 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 implement some very simple mistakes, and then just kind of be like, just go through it and then tell me,

do it as if you were just doing a normal pull request. A code review or something. Yeah, exactly. And then just write your comments and tell them. Yeah. I have done this sort of style of interviews and stuff before, and I like them a lot. I find them very effective. I think, I've talked about this

at least, I feel like I've talked about this at least somewhere before, although I haven't done it publicly. We did, at Slack, we did coding exercises, like we did a take-home kind of thing, which was the style at 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, and 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, I'd be like, not so much. No, thank you. But like, but in any case, yeah. So we, we gave a 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 dataset. It was the Enron email dataset, which is 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 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, Python, whatever. I don't really care. And it answered 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 it kind of to a fault, I think in all engineers is conscientiousness. Conscientiousness. In the same, in the way that you are mindful of the fact that even though this is a coding exercise, it's a throw up for the interview, I am going to be reading this. And so like things are sort of thoughtfully laid out. Like a style has been imposed. It's not just kind of chaos with like a bunch of stuff randomly commented and things indented or 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 stupid fortunate. So many folks I've worked with have gone on to do like great things. It's just anyway. Like 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 like kind of translating well into like when they're actually working together, they're like a lot better teammates instead of just being really trying to focus on getting their stuff done without really doing it? Getting their stuff done. That's a great point. And I feel like the answer would have been yes if I had been a good enough manager or a good enough leader to allow that to happen. Because I think what happens too often, and on teams, like I think the core data team I managed for a while was like four people and it took us, we had a super hard time hiring for any

number of reasons. So I got to meet a lot of people. The problem was 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 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 and 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 we got infrastructure 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 that I have to say no to literally everyone else at the company right now who needs 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 normal, very predictable early engineering manager's mistake. In our email exchanges, you mentioned something about the hard power of management versus the soft power of a senior IC. Of an IC, yeah, 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 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 to the extent that I had like a superpower

or still perhaps have a superpower. I'm not sure, I haven't exercised it in a while. Because of where I've worked and the things I've done, I have the ability, and this is not just unique to me, a lot of senior ICs do this, you can see around corners kind of what's coming and what's going to happen as a result of things. And again, great engineering managers can do this too for a different class of problems, right? So I was really good at Slack and at WeaveGrid, which is where I worked, the climate tech company I worked at, which I'm sure we'll talk about in 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 that 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 WeaveGrid and stuff like that. And 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 IC 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 ICs 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 then they kind of miss, they miss the power, they miss the feeling, they miss the work of being an IC. 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 had a great quote about this the other day. Like we can talk about a lot of the stuff around like AIs and LLMs 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 the sort of place that provides him 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 if it's earlier on in the growth of the company, you can like, oh, everybody's like, oh, yeah, that's a good idea. And then 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 it these sort of decisions are basically invisible no one the people take them for granted it's 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 is 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 would have failed, right? So you make almost all decisions correctly. They're 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 where like, ah, 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 it works out. 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 when I started. And it wasn't my first job. So I remember, and they're 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, I remember that. That was me.

I'm sorry, guys. Yeah. Yeah, definitely cuts both ways. It absolutely does. And again, the great stuff you see, no one sees that. It's like, of course it works that way. How else would it work? Actually, no, that was a really good decision I made.

It's very important. People remember you for the wrong decisions that you made, for sure. They absolutely, absolutely remember that. No one ever 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 revert it. 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 it's what do you people do here, right? And it 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 it. Congratulations.

Good work, everybody. Easier, you know, easier said than done. Easier said than done. It's hard to do. Okay. So I hate to do these like two part questions, but they're kind of related. Sometimes inevitably.

Yeah. Okay. I'll do my best. Please don't hate on me ironic um it's fine it's fine so why don't you sort of like do you recommend then like every engineer to at least try management and then the second thing is sort of like ah shit i forgot the second part great yeah let's just go with the first part i i think everybody i 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 without a doubt, right? Pretty much anywhere you go, everywhere. Someone should have the opportunity to do that. I think 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, and like, look,

I straight up 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 over them in everything they did and how they approached problems and how they did things. It was just unambiguously clear

they were going to be an engineering manager and potentially a very good one someday. Yes. Do they know that at the time? Because I feel like, right, for engineers, a lot of times the skill set is pretty different, right? Like for example, like EQ, right? Like, you know, it's not as highly, okay, I'm getting so, no, I mean, you're, I mean, you're right. I think again, I think if they, if they do have the EQ level, it's, it's kind of a cliche to say they can

generally clear generally clearly tell that they have a higher EQ than the people around them. Let's just stipulate that's something that people who have high EQ are good at, right? Just by nature of tautologically, like being good at EQ means you can tell, right? So I think they're certainly, 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 prioritizes 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 IC to progress up the engineering ladder at Google, just because of like all those senior ICs 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 can be tricky, because again, their inclination is that way they start taking on more engineering management 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 you're really handicapping 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 life and times. I just want to add one thing to what Guang was asking. I would say there's a huge overlap between what an engineering manager does and what a senior IC does.

I think there are... Is there? In my experience, yes. That's not actually necessarily true. Not necessarily. Depends on the team, I would say. Depends on the team, depends on the company, I think. the company i think depends yeah it depends on the company for sure at least in my experience i think there is a huge overlap in terms of you're involved in priority planning calibration

performance reviews what you're not doing as a senior ic is giving people the bad news deciding how much they should get paid yeah pretty much that say. Yeah, that's a good question. I'm with Josh on this one. Sorry, go ahead. I'd say it very much depends on the company. I think, like, you know, but I love you, but, like, you've been at LinkedIn for, like, six and a half years. I think being at LinkedIn for a long time has certainly colored your way to think that the way LinkedIn does certain things is the way. No, for sure.

Yeah. You know, not true. Yeah, I have only one perspective, which I agree with, yeah. At some places, yes, that is very much the case. At other places, nah. Not so much. Not so much. I think at Slack, engineering management was not generally involved in technical architecture decisions in any kind of meaningful way.

It was not their purview. It really was very much the senior ICs and the council of senior ICs purview in a lot of ways. And I would say the senior ICs 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 again, to 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 is sort of more important because since product

is really sort of driving things forward right it's like that becomes a much more important relationship so i mean it really is yeah it depends on the company that's yeah it depends on a big part of it for you is like what kind of engineering manager are you the more technical engineering manager or are you the more again high eq politically astute 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 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 true yeah i just got really excited because everybody's disagreeing i was like oh that's good i mean that's the best that's that's really that's what you want i mean it's a very if we're sitting around agreeing with each other it's a very boring podcast exactly yeah thanks thanks thanks i do what i can i mean i 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 deep deeply profoundly not true like not even close yeah anyway yeah cool so after slack in late 2020 you joined a climate tech startup called weave tech which you mentioned earlier we've great we've great yep i will not cut that out because i say wrong things all the time and it's part of the brand now apparently exactly so sorry so what they what they do is they build software to help the power grid to better adapt to changes in usage pattern as more people have evs in their homes during this sort of search process uh yeah what was your search criteria like right i think you mentioned that this was like heavily impacted by 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 that's sort of yeah late late 2020 kind of stuff right so yeah i mean i think i left slack uh 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 podcast 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. And like for you in four months, I didn't do any coding and all that kind of stuff. Right. And I was really sort of like at a 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 Patel has done a bunch of cool stuff. He used to be the chief data scientist at LinkedIn. He used to be the deputy CTO of the United States. He's a venture capitalist now, great guy. Kind of gave me a call and he's 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, 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 some, 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, these are just gigantic data pipelines, right? To be honest with you, right? It was a global pandemic emergency type situation. And so fortunately, unfortunately, I was like, I started doing it again. And it was,

it was a profoundly great experience for me. I loved, loved 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 are these moments early on when everyone is rowing in the same direction. And again, you can find pockets of these things anywhere at 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 rowan 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 do stuff like like about once a year or so and it's it's just, it's the happiest day of the year for me by a 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, I i was doing this i was doing this as a volunteer

it's like if they wanted me to go to a meeting and i didn't 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 influenced 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 y'all remember like in the bay area there was the day where the sun didn't rise the sky was orange scary scary ass day right that was terrible i remember like my son again he was 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 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, this, the sun's not out yet. And I was like, what? And then like, you look at the sky and it's like, basically like hell more or less, like it's descended 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 meaningfully do that. And that really kind of really drove it home for me. It 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 kinds 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. So 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 I've been fortunate to work at Cloudera when public, Slack when public. Google is still around and kicking and doing okay

as far as I can tell. Well, I don't know about that. Mine is the last two weeks, but yes. Yeah, that's it. I love them so much. They're just so hapless. It just kills me. Anyway, I've done okay, basically, as an investor, picking companies and stuff like that.

I do angel investing now and stuff. And so I invested in a lot of data tech startups, DBT most famously, but Motherduck, Materialize, Tabular, a bunch of different AI things. I do a lot of angel investing. And in spite of myself trying to be cool and look at 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 on the mission and was a real business that I felt like would actually do some good in sort of the climate fight. And Weave Grid 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 the mission. And it's an interesting mission. I mean, building, and this is kind of a, I guess, we're going to segue 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 obviously, I don't work there anymore. I left last year. is that 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 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 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 most people don't find this very satisfying as an answer but but like i i can totally relate to that because um 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 stuff and then the biggest conclusion i had was like oh i should have done like materials engineering and then learn how

to make batteries that That's super true. You know, it's funny you say that. Like one of the folks that worked at the Weave Grid actually is a physicist. He's a PhD in physics from Berkeley. And he did it to study photovoltaics and build better solar panels and stuff back in the aughts. 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 all 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 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'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, honestly. There's nothing that like a better key value store or like an S3 backed Postgres engine. These are all amazingly cool pieces of 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 materially, 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 is 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 sideshow it's really yeah we need money that's what's really what we need yeah so i wanted to get your 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 this 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 let's just start with the first yeah it's good i mean the hardest problem by far is the network issue and again it's kind of back to what

we're talking about relationships and stuff like that, right? The most important thing for me joining WeaveGrid was that I knew someone from the tech world who had joined WeaveGrid and was there already. That was a huge help, right? I think you see a lot of folks, especially in like the recruiting industry and stuff like that, who've done recruiting stuff for a long time in tech, pivoting to doing 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 would like to have worked with before, who are doing this stuff now.

This is like most of the problem. It's 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 you'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 was a company a few years ago called Opower. It was eventually acquired by Oracle and went public and stuff like that. And it was, I think in many ways, the first big successful climate tech, traditional tech company, right? There was a bunch of hardware and solars and stuff like that, right? But this was like a software company that made the leap. And those people are everywhere. Their alumni are percolated all throughout the ecosystem, much in the way that like Sun Microsystems 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, WeaveGrid is one of those companies. I think WeaveGrid will be one of on what you said earlier, anyone who wants to get into climate tech, I think being mission driven would be the first filter. They can't go into it thinking, well, I'm going to work on the hardest technical problems yes that's not what would give 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 the 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 llms for climate like for the love of god don't please don't do that it's a terrible

idea it's just absolute nonsense yeah so one kind of a random question i had was um yeah we were talking to mitchell hashimoto and then one of the things he said that really resonated with me was the most important attribute for engineers was 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 the technology. Do you ever run into coworkers that are very 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 or like how do you deal with that in those situations i mean not very well i guess it's like like thinking and reflecting on it yeah yeah not very well i only really have patience these days

for one junior engineer and that is my son, my eight-year-old. Yeah. Yeah. There's a lot of this stuff. It's a bummer. I mean, I, I, first of all, agree, I agree with Mitchell. Like it's, he's right. Pragmatism is 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 part question. What is the simplest thing that could possibly work? And why didn't you do that? And I try to be empathetic because I was once that junior engineer who was again,

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 and look how awesome I am and stuff. And getting over that has been like the work of, 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 at this kind of stuff. I do. I just sit and I just sort of seethe.

But yeah, I don't know. Yeah, you're self-aware. I think that's pretty good EQ. It's good EQ, but I need to get over the fury more or less. Again, people who are better at this than I am can get past the blind rage. And we're best at judging the faults in others that we see in ourselves. And so this is a fault I am all too familiar with and have a, have a super hard time through us. Cause 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 in my Enron emailron email database i remember some people i got a few submissions where like someone used like neo4j like a graph database to solve it and i was like yeah nope absolutely not next like under no circumstances like this is instant red flag for me not for anything when i was when i was interviewing inside data science people i would often see a lot of really nutso 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 the story. We were set on how weird they told us to use the technology. No, I mean, I know what...

In many cases, like why... Anyway, your mention of Kafka reminded me of some other discussion we were recently having at work. And it's like, just use MySQL until it doesn't work. Just use MySQL. One of my other like super favorite quotable instances was a tweet I wrote during the pandemic. Oh, this microservice could have been a SQL query. Oh, yeah. This meeting could have been email. This microservice

could have been a SQL query. Yeah, for sure. There's a lot of that stuff, man. There's a lot of stuff like that. It just kills me. So how do you filter for practicality in engineers during the interview? So other than okay so neo4j for i mean i think i think it's no no i mean the neo4j thing is 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 at WeaveGrid because we still used 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 those technology choices. And that's, yeah, it's, that's essentially how I screen for this kind of stuff is to see like,

what did you use and why that's 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 did he get into investing? Ah, okay. That was a hard fit. I know. No, 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 have 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 go public, which may happen. Let's see.

Jokes apart, but the reason I brought it up is, in a way, when you're hiring during the interview, you're looking for good engineering skills. You want to know the person knows what they're talking about. Being practical is another aspect of it. Yes. You're also seeing, can you actually work with that person or not? Or do you lose your patience too quickly? Angel investing, like once you invest, for example, and 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 podcasts, well, in a way that's kind of a working relationship too. Like, do you want to get on 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 hiring. So that's why I asked the question. That is similar. 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, you know, I mean, I guess, obviously like much far fewer people do that kind of thing. Right. I'm 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, or I guess the most common kind of failure pattern I've seen as engineering manager or engineers wanting 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 coworkers. They are not good angel investors because most

startups are going to fail. They are. If you come in with the attitude of like, well, let's 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 startup 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 can I foresee a remotely plausible path for that to happen? So that's a big shift. It's a very different kind of way of thinking.

Yeah, it's just the positive dual of the very sort of negative characteristics. You have to shift your mentality in that way. That's a hard thing. I got into angel investing because I did, quote, like due diligence. That's what venture capitalists 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. 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 capitalists 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 could have. And is that something like where you just, you would just sort of enjoy that? If do you like, did you read the book on like the rise and fall of Uber or whatever? Like, is this 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 is 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 and 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 it, 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 capitalists, Hey, I have some money now. I'd like to be an angel investor. 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? And 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 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. Because again, angel investing is a terrible idea. And again, this is one of those cliche, and this is me giving you advice that's the opposite of me and blah, blah, blah. How do you do it? 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, it 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, there's a significant luck element to this kind of stuff, right? Like without a doubt, past performance is not representative of the future. Past performance is not representative of future returns. And I think, you know, again, a lot of people, if you get kind of high on your own supply and you think that like, oh yes, cause I got this right.

I therefore know what's going to happen with those. It's like deeply not true. And whenever I run into investors who are like that, I just like give a very, you know, eye 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 setting some of it on fire and then get really lucky early on. A 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. We'll 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 investor. It was really it.

I was willing to spend X thousands of dollars just so I could call myself an angel investor. Why? Because I'm an moron. I don't know, an idiot. I thought the other cool engineers were doing it. And I'm like, okay, I got to do it too. Cause I gotta be cool like them. I mean, I mean, I think what's funny and great about Silicon Valley is the amount of status that accrues. 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, and you talk to me like, DBT, DBT. I mean, again, it's just utter nonsense. I actually, not for nothing, in all seriousness, if you are serious about angel investing, I highly recommend Jason Calacanis' book on angel investing. For what it's worth, I very much wish I had read it before I had started. Because I just, again, in my engineering mindset,

I look at him and I think, this is the least 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 that I don't know. And it kind of turns out the answer is yes, he does. He kind of actually, his advice is actually like really good. And I, like I said, wish I had read it ahead of time.

Are there like two or three things that you remember from the book that are super helpful? One is he writes a lot about how do you make yourself useful to a company 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 this.

You kind of have to have like a shtick. You have to have like a thing that is your thing that you are known for. I think a lot of DevRel people, which is effectively what I used to do at Cloudera, 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 have the knowledge they have the reputation this checks a lot of boxes like not for nothing if there was there are actually a few i think like firms that are basically all ex-dev rel people like doing venture investing and i'm like i'm largely bullish on these firms i think there's i think there's something to this um i mean they know all the problems for sure because they're talking to the people who actually because they're talking to the people who actually have the problems right and again but they yeah so I mean these are all these are like good qualities I think right so you have to have a shtick you have to there's an angle

there's a value you provide one of the ops like finance ops persons I worked with at Slack 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 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 anyway, but like, again, 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 that kind of stuff but he has like a good disciplined perspective on this stuff 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 it was, again, super useful to me because, like, y'all, 2021 was a hell of a drug. Like, everyone was investing in everything. It was going crazy. Everyone was accessible. Everyone was accessible.

We were all geniuses. It didn't matter what you invested in. It was going up, right? And so being mindful about, like, okay, how much money do I actually want to 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. Something I wish I had thought about earlier. So anyway, for all these reasons, like I said, I thought it was a good book. I thought it was really useful.

That's helpful. I recommend it wholeheartedly. So in this case, like you mentioned, the first advice you gave was, well, be useful and work for free, where this is due diligence. How does one, well, I don't think an average engineer knows a bunch of VCs 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 VCs I knew through Cloudera's venture capital relationships, because I was a very, I mean, I was a, not only at least at Cloudera, I was a senior director, which again, I had no real reports or anything

like that. I had a good title because DevRel didn't really exist as a thing back then, and I was doing a lot of customer-facing stuff, so I had a good title. You're very humble, by the way. Just saying. I don't know that I am very humble. I think I'm a pretty amazing – for all that I make fun of myself, I think I'm a pretty amazing engineer, not for nothing. My wife makes fun of me for this. She's like, you constantly 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 true. Yeah, I agree.

I am among the best in the world at what I do, like without a doubt. I feel both of those things very deeply. And so that introduced me to Jerry Chen at Greylock and then a ping and a bunch of folks at Excel. And so they got, and then a ping and a bunch of folks at Excel. And so they got, and those were 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 principal or something like that at a venture 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 to say, I know enough venture capitalists. 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 have coffee with people and talk to them and stuff. And that's, that provided a foundation for stuff. Like that was

how I originally got introduced to like, um, like Mike Dauber and a lot of folks at Amplify who I work with on 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 metric capitalists? And I was like, hell yeah, it sounds like great fun. That was a, that was my idea of fun before I had 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 really will. It's especially again, those early stage folks who aren't yet

partner, they're just building their own brands, they're building other things. Some of those folks early on have turned into phenomenal investors who are very successful. And I'm just grateful that I've gotten to know them for so many years. Especially, it's like getting to know somebody before they're a big deal is super huge and super important. And when someone takes a chance on you before you're anyone before anyone cares who you are it feels much the same way it's like yeah it's a great thing yeah quick question on being like uh sort of having your own shtick 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, as you're like,

I think your LinkedIn title is what, like a gainfully unemployed data person? Do you feel like, oh yeah, I need to be spending how many hours a week working on engineering problems such that I don't lose touch with sort of 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 DuckDB. And so to the extent that I have like a shtick online these days, it's baked in, this is the data scientist stuff, but it's a lot of DuckDB stuff. So DuckDB, very cool embedded OLAP database. I kind of, there's another thing that I sort of like caught on to earlier

where I was like, this is very cool. This could be a big deal. I think this is a very neat, interesting piece of 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, it's kind of like bringing this back around to what we were saying earlier about like working with junior engineers and 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.db. A lot of my portfolio companies ping me when they say, Josh, we've got this, we're thinking, we're 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 let's just hop on a call. Like we'll work through that and we'll figure out like why Postgres 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. Despite me again, not really doing anything. They still seem to find me. Okay. I'm very fortunate, I guess.

Is that fortunate? I'm supposing this is a good thing, right? This is okay. Yeah, it doesn't really bother me. Okay, so on the angel investing topic, last question there. Yeah. What do you look for

when you decide to invest in a company? 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 as kind of a prerequisite to have the conversation. One is that this is a person I know very well and have 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, 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 thing too, is if it's got to be kind of pretty specific to data tooling or something, something LLME, 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 from 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, that's another reason not to do things like this. Right. Thank you for saying this again. Yes. Yeah. It's like, I just should have my head examined. No. Inevitably, inevitably I get pinged by stuff where people, I literally no 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 was, 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 delude 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 sane, rational person does, right? Like 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? Would I purchase 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 i know you say to yourself well if we could just save the teams 10 of their time think of all the money we would make think of all the value we'd create i'm like just no no no no no no one cares about that it 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 ten 99 times out of 100 making companies money is the way to go don't try to save companies make the money that's what they want they want to make money anyway it's like the personal financing right like don't worry about spending 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 and i'm just like god no a terrible idea it's never worked i know i know it feels like a good idea i understand how you feel i get it i've been there it's a really bad idea 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 a company it's like tricking someone else into working so that's 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 uh program and then um so i ended up spending seven eight months like building out this sort of yeah like platform to save oh that's right cost cost of aws bill Bill and your advice. I think 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 kinds of things, there's no substitute. Tragic, tragic though it may be for having the painful experiential learning yep experiential learning is just tough to beat and no amount of wisdom or podcasts or any of these things will ever change was ever thus the human condition yeah the one condition yes or the it's the it's the what's the uh the i love the arrested development joke where it's the, it's the, what's the, the, I love the Arrested Development joke where it's like, it's with Tobias and Lindsay and like saying, you know, well, did it work for those people? No, it never works for them, but it might work for us. Whatever. These people delude themselves. Yeah.

This is so fantastic of a quote anyway. That's true. That's true. Well, whatever optimism. Yeah. Well, Josh, this has been an incredible conversation plus went to what guang said uh both of us have learned a lot it was fun like i said it's i liked 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 the chance to before so yeah thanks for the opportunity yeah of course thank you so much thanks so much my pleasure my pleasure hey thank you so much

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