Software Misadventures - Kelsey Hightower - On retiring as Distinguished Engineer from Google at 42 (Part 2)

Episode Date: August 3, 2023

Kelsey Hightower was a Distinguished Engineer at Google, where he worked on Google Cloud Platform. In this second part of the conversation, we focus on Kelsey’s retirement - the financial planning that enabled him to retire at 42, how he got started advising startups and his perspectives on compensation, turning down a substantial offer from Microsoft and meeting Satya Nadella in person. And, of course, plans for the future.

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 peeps, welcome back to this part two of our conversation with Kelsey, where we'll continue our chat about his retirement, the financial planning that enabled him to retire at 42, how he got started advising startups, and his perspectives on compensation, turning down a substantial offer from Microsoft and meeting Satya Nadella in person, and of course, plans for the future. Enjoy. So I think this is a really good place to ask that question that I'm sure many people have been wanting to talk about or learn about. You have been an ambitious person as your journey kind of walks us through that,

that at every point in time, you look at, okay, what's next and I can do better. What the pace of your life that you want to set, you can learn more skills, get a better job. At what point did you realize that you wanted to retire? You can remember I spent the three, four, five years maybe as the boss, the entrepreneur, where you decide what you care about and you execute. No OKRs, no growth, no stock market price, no corporate politics, just execute, make customer happy. If you want to focus on something,

you pivot, you focus on that, make customer happy, easy. And so during the hard times of your career, were you sitting here like, why are we talking about this nonsense? This is literally nonsense we're talking about. Is this really an OKR? Or did you just make this up because OKRs were due by Friday? This is nonsense. We all know this is nonsense. Why are we in this stand-up right now? We know what needs to be done. There's a bug. We don't know how to fix it. And when I get back to my desk, I'm going to try to figure out how to fix it. And when it's done, we're going to ship it. That's what's going to happen. So this ceremony we're doing is wasting my time.

Just to be honest, it's wasting my time for this particular use situation. What would be better is just leave me alone. Leave me alone for four days. When is it going to be done? Like if I knew that, this whole thing would be much easier. If I could honestly tell you when this will be done, I would have told you when this will be done, like I would have told you that in the beginning, right? Tech is one of those things where if you know exactly

when it's going to be done, then the problem is so trivial that it's not going to require all of this like ceremony and guesstimation. And so that part, I've never liked that part. Even when I was the VP of engineering, I remember going into one of the scrum agile sessions where people were doing sticky notes, trying to figure out what to talk about. I'm sitting there like, you have spent a bunch of time guessing and planning, not necessarily sharpening your individual skill sets so you can move faster down the road, changing the way you play, investigating new tools, taking one step backwards so you can take two steps forward. There's none of that being discussed. What's being discussed is this process,

and are we doing the process correctly? So much so, you're gravitating so much to the process that you're using it as an excuse for not being better at your job. Just to be honest, I'm not saying everybody, but I've seen enough of it to say, God, you're not being serious. You've got to be serious. And so I figured, listen, the way society is set up, you have to work, right? You got this shared infrastructure of the earth. There's rivers, lakes, water, food. This is like an ecosystem that knows how to sustain itself and life on itself.

But we live in a world where there's a gate between you and those resources. That's someone's idea. That's where it works. So if you want to get water, you can't just go with a pail and go pick up water. You've got to pay the water bill. It's illegal to be homeless.

So you've got to pay something. And so since we've got to pay something, then we go to the job and we do what's necessary to get paid so we can participate and do the things to survive. But then you also think about it is that there's some company somewhere that values your time and they put a price on it. They may give you $100,000, they may give you $500,000. Either way, they said that your time is worth this much and they're willing to pay for it. And so then there's a question you ask at some point is, would you buy it back? They will buy it. They see value.

Would you buy it back? So let's say you get enough money that you can go buy it back and say it's no longer for sale. It's mine now. And the reason why I'm saying you got to buy it back is because there's an opportunity cost, like you're not getting the revenue. So that means you're basically paying for that. And so when you get your time back, what are you going to do with it? The company knows what to do with it, right? OKRs, planning, there's something to do. And so I remember at some point in my career, I was like, people say, I love my job. You might love your job. You might. But have you really thought deeply about it? Like seriously, like our thoughts come from the world we are surrounded by. You don't just have thoughts by yourself. You just have so much input. It shapes

your consciousness. That's how it works, right? So when you say, I love my job, is it true? You got to be honest. is it really, really true? Or is this like the best job you've ever had? So when compared to something else, you hate that, but you love this. So it's a spectrum. And I said, man, and they said, I will never leave my job. I love it too much. I said, okay, maybe it's fair.

But if you had your own time back, could you not be creative enough to figure out what to do with your time? Shouldn't we work hard to be able to figure out what would you do with your time? And since I didn't have a good answer back then, I kind of felt like I should come up with a good answer. Maybe we should put some mental energy towards what would you do if you had it back? And so when I got to a financial position when i got to the level of mental confidence necessary to walk away you buy it back and people say how can you he's like how can you not how did you figure out uh what you would spend your time on if if your employer for example you if you're an employer, for example,

if you're not paying it to your employer, for example. So doing that mental exercise, what did that look like? So there's two exercises here. There's the fear of not having money to survive, you and your family. That is a very real thing. And some people have $100 million and they still worry about this. So there's no magic number for people. It's a psychology thing.

And there's world events that can disrupt your level of comfort, right? You thought it was okay, but now things cost more than it did before. Now you're like, hey, I need to make more. So there's that real number. And so for me, I remember, you know, I've been a minimalist for a long time. And part of becoming a minimalist in my early 20s was I need to understand what I like versus me trying to do what society told me to like. And that's hard. It's very hard. So when I was like 23, 24, I remember I had this huge suburban truck. I mean, just me by myself with this like big, big car. I don't know what my car note was. Call it 700 bucks a month or something. Had this unnecessary car. And I was like, I don't want it anymore. My friend's like, what are you going to do? I said, I'm just going to go take it back. He's like, you can't take it back.

I was like, you can. It's called voluntary repossession. It's going to kill your credit. And you're going to have to pay the balance. And at that time, I had saved enough. And I went to the dealership. I gave the keys. And they said, you know, we're going to do like voluntary reposition. It's going to kill your credit. And you owe us like $10,000.

Like, yep, great. I will give you the 10,000. I am now broker than I was before, but I owe no one anything. And that's the way it's going to be going forward. And so now at that time, I'm sitting here saying, what do I actually like? I need to find out. I don't care about expensive shoes. I just don't care. I'll just buy comfortable shoes that I like, and they may or may not be name brand. But I need to like it first, so I'm going to just challenge myself. And maybe I challenge myself out of convenience. Why would I pay $500 for something that I can get the one I

like for $100? And so that became the task. Now there's things that I did like, like a Mac computer. Not the cheapest computer, but I got a lot of value out of it. So that became my kind of foundation, my thesis. But it turns out when you're that conscious about things, you start making really good financial decisions. And you can save a lot more money. So when I was saving money, I also discovered like the FIRE movement, people who decided that they can live off 4%. So I had that number for so long, like, okay, if you have a million dollars, that means you can live off $40,000 a year. And if you have $5 million, then you're at $200,000. That's a lot of cash because they were pointing my career where I never made $200,000.

But not that I didn't make $200,000. I never spent $200,000. That's more important. So then I started thinking about the math and said, okay, there's the stock market. It goes up and down. These days, it feels more like a casino than it does investment. Some of these companies don't even pay dividends. Some people get hyped up and their price goes up and down. These days, it feels more like a casino than it does investment. Some of these companies don't even pay dividends. Some people get hyped up, their price goes up. And I didn't want to depend on that system, even though I've benefited from that system. Being very clear,

I have benefited from the mania where people go crazy about some stock where I work and I'm like, wow, you are making my total comp go up because you are very excited about this thing. Thank you for the coins. I appreciate it. But in reality, I wanted something a little bit more stable. So we have the stock market. You have gold. You have real estate.

You have all these things. But then I was like, why do these other countries buy U.S. treasuries? Why would you do that when all of these other things are supposed to make all this money? Because they don't need to try to make money out of stock market. They just need to preserve capital. I said, you know what? I'm going to learn how to preserve capital. So I'm going to learn about U.S. treasuries. Now, there's going to be no wow swings and that kind of thing. But what if treasuries one day paid 4%? You don't have to play around with stock market. You don't have to play around with gold and Bitcoin. None of that.

And so I decided, let's do the math. What do we spend on average for the last four years? Get that number. And I was lucky that I had enough money where I could multiply that number by like four or five. And then just get enough money that you put in the U.S. Treasury and the interest equals that number.

So if you did nothing else but sleep all day, you would make five times your cost of living on interest. And so I'm like, yeah. And so when I got to that number, I'm like, I am done. It's like, you ever play a video game where you get to like level 99 and you kill something, there's like no more experience points.

There's no more level up. You've hit the level cap. So if you want to play now, you're just having fun, but you will never go to level 100 because you've hit the level cap. So I set a level cap for myself. I say, look, at this point, you're making more you can ever spend in a lifetime. You probably will never even spin down the principle before you die. The only gotcha would be some weird hyperinflation thing. So I bought houses paid off. So I got some tangible things that I can touch and live on, paid those off and ignored all this stuff about crazy debt, do this weird. No, no, no. I need to have stability. So when I got the mental stability around the money side, I went to the other side and said, okay, how much time do you

actually have? You don't know. You think you know, but you don't know. Because if you reflect back on your life, some people feel like, man, I wasted a bunch of time. How many times did you really go to that place you love in your whole life? 12 times. You didn't go there 25 years, 40 years of time. You went 12. You went to Magic Mountain or Disneyland four times. So at best, you may go four more times. That's it, if you don't die first. So then you start to calculate time very differently. So then you start realizing that every day is luck. You wake up. Not everyone wakes up every day.

So then you start to see time difference. So when you're asking yourself, what am I buying back? You're saying, if I get lucky tomorrow and I wake up, I get that whole 24 hours to me. And I can invest it in people. So when people on Twitter say, hey, Kelsey, I'm in my career journey. Can you take a call? And I say, yes, I'll take a call because I get to decide what to do with that chunk of time. Or we were just doing, my wife had a nice graduation

party. She's an educator. She worked at the school district at the district office, but she's worked in the classroom. She had all of her colleagues. And I had so much fun because we played kickball. And I don't know, let's call it 50 people were there. And if y'all don't remember kickball, I'm from the US. So when we played kickball in elementary or middle school, we started picking teams before recess. You're looking like, hey, I got John.

Hey, I got Sarah. And you don't want to be the last person picked, right? Because you stand in the line, you got the two team captains like, John. And then when it gets to the last three, you're like, man, I just don't want to be last, bro. Like, come on, don't make me last. And I remember like, I want to win. Kickball is serious business. We got to win today. We didn't come to play around. We're not just having fun. It's exercise. But we came to win. And so that day, June 30th, we had a kickball game. And I can see who was serious. I was walking around. We are adults now. And a lot of the people there were her colleagues and adults. And there were some kids and there were some teenagers. Now, the

teenagers were serious business. They came with their tennis shoes on shorts they wasn't trying to look pretty they came to play kickball so i cast out i was just scouting people so i was meeting people hey i used to work with your wife was like yeah that's cool interesting what was your batting average in middle school though can you catch the ball like i need to know these things. So I'm just walking around, getting to know people and judging their kickball. So we line up, and we're picking people, you know, picking teams. And there's this one guy here, I don't know if he's from Air Jordans. I said, hey, man, I want to pick you, but you're not serious with them Jordans. You're not going to mess up your Jordans.

He was like, I got to change your shoes. I said, oh, okay, you ready? And so we play this game of kickball. We're down like, I don't know, eight to like six. And my team ain't really catching the ball like they supposed to. So I don't know if you remember middle school. Those are the kids that run and intercept the ball because they know you're not going to catch it. Like, hey, I got it. I was like, no, you don't. You didn't drop the last three. So I got to catch it for you. And our team gets serious.

I'm starting to coach the team. I'm saying like, hey, guys, listen, kick to the left. Kick to the right. Don't stop running because ain't nobody really catching the ball and throwing it back in. So we just finna win the game. So we win 10 to 8. And I thought about it. This is what you get to do with your time, too.

This counts. All those experiences we had You had adults that haven't had that much fun In a decade Like you think going to the beach And like paying for expensive drinks Is fun Sometimes it's just stressful

But getting to be a kid again For an hour playing kickball The game was free The ball cost $12 from Walmart. And everyone was out there having fun, running around like a kid again. And to me, I'm like, man, that's what you get to do with your time. That's the thing you get to do with your time. And so now the value I have on my time is really, really high.

Not to go figure out how to make more money. I'll do that too. Still do advising to startups. Still speak at conferences that are paid. But boy, if I can just hang out with my friends and just create the memories that when you see each other three years from now, you say, remember the kickball game when y'all came back? That's what I want to be able to do as well with my time. I'll say it takes courage to get to that decision of course financial financial safety but also courage uh like you said it's when you say no to a lot of opportunity cost there you're walking away from a huge chunk of capital that you're not gonna see if you were there so it takes courage

it's really cool because one of the questions i had or we had was that um you know retirement is not an easy transition for like very ambitious people just because like you know you're really good at what you did right like now we have all this free time all this like you know there's no responsibility right and then you have to figure out like okay what do i spend my time to make myself still feel like right like i was on top of my game like i was before but through your like stories now i'm realizing like yeah you've changed the game right so the game is no longer trying to you know just get money and then have the safety right and then now it's a very different and then you have control

over sort of like what's the game that you that you want to play and you can change it right as um as you go i'll be honest look i have an ego like everybody else and i do think there's a bit of this stuff that is ego driven if we're all just being real honest like being really good being the boss going in the office and having people look up to you and respect to you, that can be very addictive. You may want more of it and you can never see a life for yourself without it. Luckily for me, my ego has been satisfied thousands of times over. Book, Wikipedia article, awards, keynotes that people like and they mention. I announced my retirement and people tell all these wonderful stories that make me feel like I've achieved a lot. And so my cup is full in that regard. It's like, my ego can't ask for

anything more. It's like, dude, like, what more do I want? I mean, I remember like getting some accolades and I take the reward and just put it in the trash. Like, I don't need to look at it all day. I have enough. I don't need anymore. And so I think that does make it easier when your ego is satisfied. But I've also been trying to challenge my ego all these years to say, look, you don't need anyone to think that you're the best this or that. You don't need it. That is superficial. If they give it to you, they can also take it away from you, and then how are you going to feel? So you got to get to a point, if you can, that you say, I appreciate those things, but I can't need them because it's not going to work out for you a long time.

You don't want to fall into depression when the promotion doesn't come. I want to have something a little bit more sustainable. So I've always tried to be really cool at challenging my ego, checking it when I see it getting out of hand, and just try to keep yourself grounded. And if you do that, though, I think you have an easier time giving it away because I'm saying, I don't need it. I've appreciated it. And I'd rather have something that says, hey, Kelsey, you really helped me, even with the small thing. I take pride in that. So you're right, as a person who is very ambitious, you've got to figure out how to challenge that ambition to something else.

And I remember we bought this new house and it had a fireplace in the center of the room. And I remember, I'm like, I don't want to mount my TV over the fireplace and be looking up at the TV.

First world problems. Yeah. First world problems. Yeah, first world problems. And I'm sitting here like, I can't go out like this. And then my buddy sent me this Reddit thread. It's called TV Too High. And they show all these things where people mouth the TV too high. And I'm like, man, now I feel even worse. I can't do it.

And so I was like, it's a nice fireplace. It's a nice little, my wife was like, I like the fireplace. I was like, but, so I put the TV up there just a little bit and we're watching. She's like, yeah, it's kind of too high. I was like, yes, what I heard was I have permission to change this thing. But I decided that I'm not in a rush. You could just call someone, pay them, do it all. But I was like, I'm going to learn.

So I said, what's behind there? And it's a gas fireplace. We called someone because you got to have a licensed person do it. They took the fireplace out and I'm just sitting there. There's no fireplace. They had to kind of mess up the wall a little bit to take it out. I was like, I'm just start pulling stuff off. And so now the drywall is off.

The wood paneling, the shiplap is off. My wife is just sitting there like, oh my God. So now we've got this mess and I clean up the mess. And now there's just this frame of wood studs that were framed out for the fireplace. I was like, I bet I can reframe it for the TV and where I want to mount it and all the cables and all these things. And so I was like, I just watching YouTube videos, how to build an inner wall. for the TV and where I want to mount it and all the cables and all these things. And so I was like, I'm just watching YouTube videos,

how to build an inner wall. And I bought some tools and I took the wood out and I'm cutting the wood and I got it framed up. It took me a while. And then I had to reroute the electrical to go through the studs into the places I wanted sockets for where the TV would go. So I learned all the electrical codes, found out if I needed a permit or not, watched more YouTube videos.

And I was trying to make it perfect to code to everything. And then put the drywall up. And then put the shiplap the way we like it. Got to paint it. And then we mounted the TV. And it looks perfect. But my tool bag is full i have all these new tools i have all these new skills and so i just channeled it into things like that right

and now we can enjoy this like little thing and i don't know for me in my life now i'm like hey whether it's cutting the grass or doing something like that i'm gonna learn how to be happy with those results too i was thinking about as you you were talking about how you're thinking about time now. And a couple months back, I was reading this book, Man's Search for Meaning. And the author talks about that when you have a meaning or a purpose in life, that people succeed by whatever definition of that success means to them. And when we are at work, in many cases, like the meaning or purpose here is to get this project and get that next promotion or buy a house or whatever it may be. At this point, what let's just say society calls traditional success or traditional meaning or purpose, you've been through that. And

in fact, not just from a financial standpoint standpoint even i would say from pure skill and engineering standpoint like before this announcement to retire you were promoted as a distinguished engineer at google now that is very few people are at that level let's just say in the entire tech industry and that too being at a place like google that means a lot um and so it's not just that you had financial success. It came as a byproduct of you succeeding as an engineer. So at this point, now that you have all this time in the world and you're looking at many things within your life and seeing what to do with it, how do you think about meaning and purpose? I mean, that gets really deep because number one is I need to unlearn that you need meaning and purpose. To me, that's like the first step.

Because if you need meaning and purpose, then you're going to find one. And if you look around, what you're going to find is go get a job, make a lot of money, buy things that people think are impressive. That's what you're going to find because when we say meaning and purpose, we're talking about based on what's available in the society we currently know. We're not really talking about true meaning and purpose because it's hard to even discover that. You have to unlearn so much and go into a whole another realm that is not even observable by normal people. And so if you try to find a meaning and purpose in our current understanding of how things work, I think you're just going to land on very predictable things. And so for me, it's like, hey, who cares about that thing? I am here. That's step one. I'm just here.

Okay. So if you're here, what do you want to do with it? What can you do? So if you want to be able to build a house, you've got to learn those skills. So then you can just build the house. If you want to educate people, then you have to learn how to write. Okay. It's very straightforward to me.

So in that scenario, it's like, go get the skills so you can inflict the change you want to see. That's it. That's like kind of the thing. So if I don't want to do anything, then don't do anything. If I want to be able to educate people about some philosophy I have, then there's so many ways of doing that. I can communicate it, so go learn how to tell better stories. If I want to do it in a book, be patient. I don't need to rush now. The book doesn't need to be done by November. I can just take as much time as I want. I can pay the copy editor to make sure it's great. I can read it multiple times. I can add images. I can do whatever the best technology is for printing a book now. I can do

very slowly and no rush. So just take your time. And so hopefully when you produce the book, people look at it as like, wow, something's different about this one. You can tell the person wasn't rushing. And I think honestly, that's when we actually do the best work is when there's no rush. You're still accountable. You're still working towards it, but the deadlines go away. It's not the best we could do by November. This is the best that I could do, period. And I'm ready to let it go to you. And when you see it, you'll say, this is great. And I think a lot of times the people who have the ability to do that, they have this unfair advantage. If you look at when Apple released their Vision Pro headset, whether it works or not in the marketplace, that's whatever.

But when you saw it, you can tell that this is different. When they released the first iPhone, you can tell that someone said, oh, we can just ship a phone with a stylus like everyone else is doing. They said, no, we're not doing that. This thing ain't ready until you don't need a stylist. What? Not everyone has the luxury of waiting until they say it's done. And so I think having that for your own life, there's a lot in that. And then some people will look at that and say, oh, your purpose is to be the best author. It's like, well, if that's your takeaway from it, that's cool. But I just have the time and space to be better at whatever I want to do. And so I don't know about the purpose part from like society's definition of purpose, because I think it's a little too narrow. But what I'm finding freeing is just unlearning

a whole bunch of stuff, realizing that I've been influenced by tons of things. So now I'm learning how to cut the certain things off. Like when you look at all the superheroes and villains, Magneto is very special, right? He's like the only one that knows you need to put on the helmet because you have no idea who's influencing the way you think about things. And so he just wants to be careful. And before he does anything, say, hey, put on my helmet because I don't know what y'all are doing to my mind. We know people out here can do that in that world. And so now I'm just being conscious about that. So I don't know. I've had a purpose throughout my career and it was definitely fit the definition of society's idea of purpose. But I do think there's this core of like taking pride in what you do,

respecting yourself, because people I think that tend to respect themselves, they tend to respect other people, because they know what it feels like. And so I want to make sure that those core things are there, right? Empathy, kindness, I want all of those things. So I can reflect them back in the world, and just give my space to do the best possible. do you balance this with you know a lot of what makes us great is the urgency right and like that hustle that you talked about at the beginning how do you balance sort of overcoming the fear of losing that as part of sort of your identity or like that's what made you achieve all these things and to a point maybe part of it is

you know it's not about achieving things right as it has been before like the game's different now but how do you but how do you think about that like the yeah the lack of urgency right like now you have all the time and the resources right to do these things um i think that's a good one you know when you think about you know this concept urgency, you know, you want to make sure you're being accountable. The reason why we give people deadlines is so that we don't like just waste time and we're like working towards something. And I think that stuff is truly helpful, actually. And so when you don't have the deadline, it takes a lot of integrity, self-accountability to make sure you're still making progress. And so things like as a minimalist, I don't like having clutter. I don't like having mail that has

been attended to. I don't like an email box that's too full. So instead of me saying I got to read this email by a certain time, I just want my inbox to stay at zero. And the only way it can stay at zero is I got to process all the email as it comes and either say no to what's being asked or say yes and just do the thing as soon as possible. And so a lot of times it's like, oh, I got to donate stuff. I'm just leaving right now to go donate. I got to go donate the clothes and just get it done. I don't want to sit there for a week. I don't want the clothes there. So just do it now. So I try to figure out how to prioritize things that I can just get it done and just get it done or just say no. And I think in tech, time has always been this illusion.

Like, look at our backlogs. The backlog kind of represents the imbalance that we thought we had. Oh, just ship it now. We'll fix it later. And then you look at the backlog, there's like a century worth of work in there. You would never finish that backlog in 100 years. And so we were never being honest about time. We keep saying that we can just fix it later.

We can add that later. We can just change it. The truth is you can't, not all the time. And so we just throw it in this backlog. You're never doing it. So if you're just being honest with the time, you're just saying, no, I cannot do that. We're not doing that. Or we're going to ship it as it is. And if somehow we really, really want to change it, then make time for it. Or we're just going to put on this

backlog and then we're going to lie. So to me, the backlog is like you're kind of lying to yourself. You're never going to do it, but you're just giving people this sense of hope that somehow you're going to find the time. You didn't have the time now. That's why you made the decision to put on the backlog. So what I do now is say, hey, listen, time is this illusion. You may not get tomorrow. Tomorrow ain't guaranteed. So now I say, okay, what can I do today? Today, I mean, just before I got on this call, I went through all of my little papers, loose papers. And I'm like, okay, flipping through the paper. Do I really need this piece of paper? Maybe I'll take a picture of it and put it on Google Drive. The paper has to go. Or this paper is for like an appliance I don't even have anymore.

The paper needs to go. And so I'm constantly trying to prune and clean and just be honest. Are you going to do anything with it and clean and just be honest. Are you going to do anything with it? No, you're not. If you are, just go download the manual from the website later on. You don't need to keep it. So I think that's how I try to balance things. I kind of prune, keep as few things as possible. When I say yes, just do it. Honestly, I looked at the clock. I was like, damn, I forgot about this podcast. I should reschedule it. But the problem is if I reschedule it, I'm promising something to my future time. That's not right. Do it now.

Do the podcast now. Yeah, do it now. Go see it. Why I have the time. So that's the way I think about it. It's more of, I remember there was this saying, it's like, you know, have nothing to do but nothing left to be done. So if you know it needs to be done, just do it, and then you will never have anything to do, right? But that doesn't mean do nothing. So look around, hey,

do I, I don't even read all these books. Maybe I should donate them. Drive there and donate them, get it done, and stay away from the backlog. So that's how I do it. I try to stay away from the backlog. So when I say there's something that needs to be done, it needs to get done relatively soon. And you're right, there are some projects that take years to do, like you're going to write a book or you're going to write some code. But I think then you've got to have little smaller milestones, like just making progress towards it. Did you write any words today? No, you didn't. Okay. Are you really working on the book or you're not working on the book? Right? So I think you do got to hold

yourself accountable when no one else will. By the way, is there a book that's being written? There's no book right now that's being written, but I'm learning through my keynotes how to tell the stories. And when I get enough of those stories, maybe you do make a book of it. But I'm learning how to be very patient now. So when a conference says, hey, Kelsey, would you like to give a keynote of the conference? I was like, you have to trust me. I know you like the live demos. I know you like when I talk about just purely the technology. And don't worry, we can go deep on the technology. But you got to let me try it in the new format. And I have to be able to tell stories and put context around it. We can go deep, but you got to let me try it in the new format. And I have to be able to

tell stories and put context around it. We can go deep, but then I can touch the machine and the person. And now conferences are allowing me to do that. And it feels really great because now I get to learn all these new things, but I'm telling deeper stories. And I think that part, those are the chapters writing themselves. So sometimes I'll go listen back and be like, oh, that's a great way to phrase that. So if I ever do a book again, it will definitely be self-published. I would definitely take so much time that when you get the book, you'll feel like I'm learning all of these technical concepts through life. And I just want it to feel different. So if I ever write one again, it's going to be like that well i do hope you write one and we all get to read it yeah in many ways i mean every tweet is like one of the

paragraphs that could be in the book so you're kind of doing the rough draft so to me like when you write a book life is the rough draft right you got to live these things so to me i'm just living there are song There are artists who say, hey, where's your next album? It's like, yo, I got to live a little bit because what I'm going to write songs about. So it makes sense. I can't do an album every year. I haven't lived enough. And so I do think life is a rough draft to like me writing the book. So right now, the rough draft is accumulating and I'm finding like a good style of like, man, I remember reading this one book and it starts with, he's just looking at his desk and there's

a pencil, a piece of paper, and the desk is like this iron piece of desk. And he just goes through the history of how man gets to paper, how we get wood and we learn how to work with wood. So then he has to go to the origin of like the universe and how it comes together and then how you get trees and then the manufacturing process of cutting a tree and then shaping it to these things but the level of patient you have to have to start from a single desk and then talk about humanity's evolution to get to the pencil that's the kind of patience that i want to be able to deliver to some of these things. So at this point, I think someone tweeted that, hey, Kelsey, are you taking a break from tech, or is it just something else? And you mentioned it's a break from the regular nine to five, but you're still going to be part of the technical community. It's bigger than just a job.

And you mentioned that if everything goes as per plan, then this would be your last job that you had at Google. So is there a plan or are you taking it as you go? Yeah, if I can afford it. No more, I don't want to sell. And it's not like the work is bad. I just don't want the artificial deadlines. I don't want the artificial need to keep growing at 20% every year or the investors get mad. I don't want the artificial deadlines. I don't want the artificial need to keep growing at 20% every year

or the investors get mad. I don't want that. I don't want to be on that timeline. It doesn't even lead to the best work all the time. It just becomes the work. So I'd never want that. That, if I can afford to, I would avoid it forever. I don't need it now.

There's a time I needed it. I appreciate it. I learned how to do it well. But if I can afford it,. I don't need it now. There's a time I needed it. I appreciate it. I learned how to do it well. But if I can afford it, it's time to stop. And then when it comes to tech, the way I think about tech is so crazy. And people say, hey, tech is this like very unique thing. Is it? Or is it just a tool? And the way I used to try to like the analogy I like to use for developers is you say, hey, get your laptop, build me the thing. And they always ask the same question. Build what? I say, exactly. The what is the whole thing that's important. And that proves to me that the computer and the software, the

compiler, the programming language is just the tool. That's how it works. And so if you think of it this way, spoken language is a very powerful programming tool right it tells people to go left it goes right it tells you what to think our stories influence people it tells people it describes things that they then turn into their own north stars and then people move in that direction their whole life so if you think about if language is like a tool that's very powerful, then all this other stuff is just tools. So it's like, you can never get rid of tech. Like tech is just a tool to me. So if I'm like, man, I need to automate my calendar or how I think about reviewing and accepting speaking engagements,

why would I not reach for a tool that I've learned how to use so well? It's going to always be in my tool belt now. It's not necessarily like my job, but boy, is it in my toolbox and it's going to stay there. And by the way, so when you decided that you wanted to retire, you would have had a conversation with your manager at Google. And I'm sure they must not have been happy seeing you go. What was that

conversation like? Well, so you got to remember there's multiple, so usually when you're retiring, you're not asking nobody for permission. Of course. Of course. It's like a notification. Yeah, it's a notification. Yes. It's not a notification. Yeah, it's a notification. Yes, it's not a notification. Yeah, there's no action to be tucking on the other side. It's more like, this is happening. So you got to remember, that's how those conversations start. So when someone tells you that they're retiring,

you know that they feel like they've accomplished all they can. They understand what they're walking away from. They're not saying, I'm quitting and going to another job. And if you give me more money, I will stay. If you change my work conditions, I will stay. I'm saying is there is nothing that a nine to five can do. Now, maybe there's a magical number. If someone said, I will give you a billion dollars a year. In some ways, I would still feel obligated to take the billion and go fix things in society where money still is the main tool to drive that. There are people who don't have running water. I would give them running water. You know what I'm saying? There is a number where it just becomes

irresponsible not to take it because of what you can do with money. But that number is not necessarily 3x for me, right? And so you look at that, and yeah, there were some proposals. There was like, hey, what if you just go to part-time, like so part-time where you're literally doing something like once a quarter. And you still can make a large percentage of what you're making. And it's really appealing. But then you have to ask the question, what strings are attached? Well, you still have to honor the kind of conflict of interest.

You know, you still can't invent nothing and then it'd be assigned to us. And then you're like, why am I, why would I, that's not why I'm retiring. I'm not trying to pay attention to the rules you have in the employee manual. So the conversation is like, hey, it's honored that we can try to figure out a situation that gives me the majority of my time back. And wow, a lot of the compensation, that's really great.

But then we look at the strings attached, you say, hmm, that's not my idea of the freedom that I was looking for. And so then you just have to be very honest. And honestly, I was very proud of myself to walk away from that. I was like, yo, you're serious. You put more value on your time than what they were offering. And honestly, when you think about retiring,

this is something that to me was years in the making. You got to get the financial piece right. You got to get the mentality right. right you gotta get the ego right if you're not a distinguished engineer at google then what are you right that that's hard like when you go and fill out an application even for like insurance employed or unemployed yeah there's no in between. I got to click the unemployed. And then some people would be like, dude, you're unemployed, bro. How are you going to pay for this? So you have to answer a lot of questions because society isn't built for people who can work but choose not to.

It's not really designed that way unless you're kind of like at a point where, yeah, it's really not. Like if you have the ability to typically work, society is not really set up that way. you're kind of like at a point where yeah it's really not like if you have the ability to typically work society is not really set up that way people be confused like yo you're not working yeah what's wrong with you yeah what's wrong and so oh man so i think that uh i don't know i think that's kind of the the hardest part that you have to kind of get to that conclusion so i kind of felt like i finally got to that conclusion that I was really ready. And then you wake up the next day. So remember, when you turn in the laptop, you turn in the badge, and it's funny, the first thing you appreciate is not having two email boxes, right? Because like when you, when you're doing like stuff on the side, whether it's's advisory work or speaking engagements,

you've got two email boxes that are important to you. You've got your personal email you've got to pay attention to, and then you've got to look at the work email to see if someone's asking you to do something. Is there a reorg? Something's happening. And so even though they say 9 to 5, that's not how it works. It's like 6 a.m. to midnight. Because in knowledge work, it's your how it works. It's like 6 a.m. to midnight. Because in knowledge work,

it's your mind that they're paying for. And so your mind is always going to be attached to that email box because something is happening. Maybe someone's going to try to put a meeting on your calendar, and you got to prepare mentally for that meeting. And so when I lost access, that means the calendar is not even on your phone. And you realize that you can't eat. It's not even possible for someone to ask you to do anything on that calendar. And that's when it really feels real different. So it's not until the access is off do you realize.

And then your brain is having to defrag. Remember, if you're like me, you kind of knew what was on your calendar for the next two or three months, right? Sometimes you even have to book travel for it. And so when it's gone, your brain is like, oh, I can purge this? Are you sure it's like the cash? I'm going to leave it in the cash because you might need it. I'm like, yo, you don't need it. You can't need it. You're going to purge the cashge the cash like yeah you can purge the cash and now my brain is like purging the cash right now i don't know how long it's gonna take to get it all out but um i'm in that cash and validation phase yeah how does it feel when you wake up the next day like before it used to be you know exactly what's on your calendar you

know what you need to do but at this point it's different so what does that feel like when you well here's the thing there's a lot that you learn about having a professional job. I tell a lot of people who are struggling, like, you know, there's a lot of people in society. Their plan isn't more than five minutes into the future. Seriously. There are people who wake up and they only think about the next five minutes. I got to get on this bus to get to the job. And I'm thinking in five minute increments of this job, I look at the clock and I can't wait till it's five.

I'm going to catch this bus back home and I'm going to watch TV and unwind and wake up and do it again. That's it. They're not thinking about what is the Fed interest rate and how they're going to invest in this thing and then invest in that thing. That's future planning. They're not really thinking about, you know, should they buy this house? Is the market right or not? Nope. I just hope they don't raise the rent.

I got to make payment. And so when you can't think that far in the future, it changes the way you behave. You don't really have a lot of excitement for the future because you don't even like the present. It's very different. So in a professional job, you are strategically learning about different things that need to happen. And again, that becomes a tool in my tool belt. I kind of like that part. So now in my personal calendar, how's my health? What are the metrics? We know the metrics for the computer. We know the metrics for the low balancer, but what's the metrics for me? Is my heart healthy?

Is my blood healthy? I need to find out. Man, I need to do some observability. So now I'm not downloading Prometheus, but maybe the Apple Watch is a little bit more appealing because I need to know these metrics. And so now I got work to do. I need to go find out all of my metrics inside and I want better observability for me, for my body. So now I'm

like, okay, I got stuff to do now. So now I have a plan. And then it's like, okay, I got insurances. They're tax deductible when you're sole proprietor. How much taxes are we talking about? And so now I'm like going through and finding out out, oh, I can have a lot of strategy. It turns out everyone goes on vacation roughly around the same time because of work. But boy, it turns out there's a lot of off seasons, and travel is a fraction of the cost. So when everybody else is going to school, you can go to the beach because they ain't there. And so now I'm learning like what the off seasons are about. I'm inviting friends over and now I'm planning what the experience will be and not like, oh, hopefully I get off on time

to put something together. So I do use a calendar, but what's posted on that calendar, and again, again, I still do advisory, I still do some podcasts and things like that, but now I'm starting to be very intentional about my own life and making sure that I'm planning and scheduling. When is your passport going to expire? Just go ahead and put a date there so you can be ahead of the curve on those things. And so now when I wake up, you realize in your normal life, you're not as diligent as you are with your work. When we say work-life balance, think about it at work. We know our deadlines. We kind of do our things. But at home, you try to do auto pay for

your bills so that doesn't lapse. But then there's stupid things like, oh, you have 10 more days until you have to change the ID or it won't be good now you're scrambling trying to get an exception because we kind of procrastinate a little bit like do you really change your filter in the hvac system no it's just like when it stops working the guy shows up like dude you never changed the filter he was like man, I was so busy with life. So now I'm like, let me go check the filter. Who makes the filter? When were filters invented? That's it. So it's just same kind of skills apply to your real life. And you mentioned startup advising. What does that look like? So for me, it's been, it has contributed to one of the reasons why I can retire early because, you know, once you get involved in cat tables and you're fully vested, employees have one timeline of when they can sell.

But when you don't work there and you have preferred shares, that means you can do private equity sales. And so the startups that I'm involved with, you, for me, it's like I play a part-time PM. So I think about the product development, what the command line should feel like, what logging in should feel like end-to-end. I just can't unlearn that. I don't want to unlearn that. So I give them that. The pricing. The pricing isn't correct. I wouldn't pay for this, not at this price. You have to have something more approachable to the customers. And so you may get into the business side, like the pricing and the revenue growth.

And sometimes the founder needs someone to talk to. When you're a founder, you can't tell all the employees the problems because they'll lose confidence. So now I can ask the founders pointed questions like, how much runway do you have? If you run out of money on this day, what happens? To avoid running out of money, what do investors need to see?

And then you're also teaching the founders sometimes like how to speak. A lot of founders believe you have a good idea, you build good technology, you raise money, and then you have a successful business. It's like, nah, the way we are now, the founder needs to be able to tell the story really well. I said, oh, I just hired someone in Devra.

I said, you didn't listen to me. The founder must understand how to tell the story well because your employees want to hear the story from you. Your customers want to hear the story from you. Your investors want to hear the story from you. And if they don't trust that you can paint a vision, they may not understand why they should be investing. If you're an employee, you don't understand why you're working there. I need to have someone with a strong vision because I am

banking on that vision to lead us where we need to be so these stocks can be working anything. So what I'm noticing after doing this for years is that you become sometimes a mentor to some of the founders. They've never done this before. They're nervous about their ability to talk in public because now people are asking them to talk in public and they notice that they're not being able to inspire. So you're kind of coaching them up. You're doing the product development. You're helping people go to market.

Sometimes I'll do a Twitter space for some of the startups I advise. I say, listen, you have to be authentic and you have to learn to talk to your customer. So we do the Twitter space and then the authenticity comes out. They find their voice. The team finds their voice. They also get to examine the market, talk to real people. And after the Twitter space, they're so relieved, like, wow, okay. I was like, yeah, that's part of the feedback loop. So it's been this thing, it feels like I'm a tactical product manager,

I'm a tactical mentor, I'm a tactical engineer, and then it's stateless. So after the session is done, it kind of disappears, there's notes. And then the next session, I kind of put on the founders that they had to repopulate the cash. And then we do creative again, then we turn it back off. And that's just the best way for me just to make sure I don't get caught up in the day to day. Because I don't want to agree with them all the time. I want to be able to give them this outsider's perspective. So I stay the outsider. How did it start, by the way? And how does one usually get involved with startup advising while still having a full time job? It's tricky, because you have ethical boundaries you don't want to cross.

You know, you got to make sure that, hey, we're not advising the company that does exactly the same thing your employer does. So you got to be careful with that. And so the first time I did this is you had some people that may have overlap, but they were invested by Google Ventures. And Google Ventures kind of made sure we got the all clear that Kelsey can be involved. Or sometimes you're dealing with companies that are doing stuff that has nothing to do with what your employer does.

And so sometimes the offer will be like, hey, we would like to be an advisor. I don't just do random advising unless I can help. And so for me, monthly retainer and I need equity. And so now it's on the founder to make use of your time, or they're just wasting money. And I remember the first time we did this is, there's one company, I won't mention them, but we started working together. And people are like, we're going to pay you and equity?

Hmm, I don't know, man. It doesn't make any sense. I was like, well, you can cancel at any time. Oh, okay, well, why not? We'll try it. And I remember the first set of sessions, the feedback for them that they found valuable, they just changed the website. The website kind of mimicked the conversation. And customers and users, it resonated more. And they were showing me like, hey, the VC was like, hey, we need these people to come out of stealth soon. It's time to get into the next phase of this investment.

It's been a couple of years. It's time. And I met with the team. I was like, this is not ready. And I told the VC, we're going to have to move six months. And the VC's like, are you serious? I'm like, 100%. You need to pivot the core message.

The product needs to change a little bit. The onboarding needs to get cleaned up. And they've got to change the way they talk about it. So we have these three conferences we want to hit. Go4Com was one of them. We need to actually tell the new story with developers and see what does it resonate and the product should match. And then at the end of the six months, we can do like a user conference. I mean, they're small, but we just did this user conference thing. And so I kicked off the keynote by showing the product, you know, the vision I had, like, hey, here's how you should think about it.

Here's how it works and show it to them. Fireside chat with the founders. And it's funny, the next day they got acquired. Wow. And, you know, they got these offers in. My guess is, you know know maybe they knew about them already but I think the video helped the thing we did helped

they liked the narrative they got bought and I remember getting the check like my shares got accelerated and you just wake up and the lawyer's like hey we need your banking information I'm like for what I don't owe y'all nothing and they sent me this check and the check was well, I don't owe y'all nothing. And they sent me this check.

And the check was pretty big. And I was looking at this check like, what the hell is this? Like, whoa, okay. And I've gotten bigger checks since then, but I was like, wow, this is what equity means when it pays off. And so I was like, you know what, going forward, I will only work with startups when I can make that kind of impact. I need to be able to impact the vision. I need to be, and it's not like it's just all my ideas, but I just want to be a person that when we are brainstorming together, they want to change the website. They want to pivot

the product. And then they're happy to give me the equity. They're happy to pay what they pay on the monthly retainer. And so now that's just been my formula. So now, and here's the thing, whenever a founder and VC is willing to give you credit for the work you've done, that makes its way in the startup community. Other founders are like, hey, I know what you did over there. This is not smoke and mirrors. We want a taste of that. And you give them a taste of it, and they're like, okay, your reputation matches the output and the performance.

We would love you to be on our cap table. So now you find yourself having to say no. So I don't like to do overlapping companies that do the same thing. That's not fair. But I knew that this was going to be a big part of my transition. So as I pivot out of Google, you better believe that was going to be a big part of my transition. So as I pivot out of Google, you better believe that's going to be a bigger part of the portfolio. Not too much, because you don't want to give away too much of your time, but just enough that all this experience

and all these tools that I built up, they can be put to use for the next generation. How do you decide, so when you started, how do you decide what should that engagement look like like in terms of retainer or equity because when you first started i'm assuming you you hadn't done this before while you were still working but at some point you got the opportunity with some company you saw that you could help them um how did you go about thinking like this is what a retainer should look like or this is what uh the equity should look like yeah how did you go about thinking, like, this is what a retainer should look like, or this is what the equity should look like? Yeah, how did you go about that process? Man, I'm giving away too much detail.

I'll give it away. So I looked at my monthly expenses and said the retainer must be that. And if you get 10 of them, then you're getting 10 months of expenses per month. And then you can look at that as a future investment. You can put it in other investments. And so I was like, because if I only ever did one of them, and you say, why are you doing this? Number one, you definitely want to help the company. But what retainer makes sense? Well, the retainer that makes sense to me is like, you know what?

Let's figure out what the living expenses are and do that. Remember, you already have the interest times X already. But you say, what's the magic number? And I said, what does life cost? And right now, life costs this much. So then you just make the retainer that. And then the equity is like, you just need to make sure it feels right. That if this company were to have a great exit, do you feel like it was fair to you as well?

And so you ask for things like accelerators, you ask for things like two-year vesting cycles, 10-year exercise window. Because the thing is, if you are impactful in a way that the founders want to continue for the whole two-year term, and they use some of the things that you brought to the table, then you should have a 10-year window to exercise and not lose it all

when you need to move on to something else. I think that is only fair. And so you put together that. And so here's the thing. The best way to say no is sometimes to say yes at the right price. Right? So someone says, hey, we would like you to advise and you say no problem it's this much oh we can't pay that it's like okay you're saying no i didn't say no i said yes at this price so when you first started did you let people know this is something you were open to or does this kind of happen organically no i think the first time someone asked me to do this, I said, listen, I cannot work for free. It's just not fair to me, to be honest. You're a for-profit company.

You have ventures giving you these checks so that you can make an outsized return. And the thing that they're investing in is your ability to execute your knowledge and your expertise. So the upsides founders have is immaculate. Not all of them are going to make it. But the ones that do, the upside is phenomenal. And so I've worked at some startups where the equity went to zero. So you put in all that work,

you take a discount on pay because of the upside. The upside is worth nothing. That don't feel good. Or you leave, but you don't have a 10-year exercise window, and the founders do. And then there's an exit, you get zero. I said, I'm never working for free, so why would I advise for lottery tickets? It doesn't make sense. And so I said, listen, I can't be working for free. So you got to pay the retainer. And if you don't want to pay the, are you getting paid a salary, founder? You are? Okay. Do you pay your light bill? Do you pay the internet bill? Do you pay your cloud bill? So you're paying everything that is a value. Either I'm of value and this is is a no-brainer, or I'm not of value, and it doesn't make sense.

And so the first time I said, I just cannot work for free under any circumstance. Worst case, the equity is worth nothing, but I feel like the retainer fees, I know what investments I bought with them. I know exactly what part of my life they paid for. So it's fair, right? So I do take a balance of retainer plus equity because it wouldn't work without both. So I just promised myself no more working for free. And then you run across someone who says, that's a fair deal. And then what happens is when they like the model,

they tell the VC, because they got to remember the VC has to approve a lot of this stuff, right? Because you've got to get allocated shares, and they're seeing that there's this other component. And a lot of times your board or whoever you've got to get approval from looks at that and be like, what the hell? What is he doing for that? And I remember after having maybe 10 of these, a startup was like, we need you to write a thing to justify this, which is no problem. But I said, hey, listen, I am not trying to get 100 of these. So if you don't believe the ability to counsel at any time, if you don't believe my check record is correct, if you don't believe my references, and you still want me to do this, how about this? No. It's like, what do you mean no? I was like, no, right? Because in order to do this,

I got to trust you. You got to trust me. I've given you the references. You've seen the other work in action and you're still asking me to do this. And maybe my ego was involved, but I was like, hey, no, this isn't the right fit. Because in order to get the best out of me, you got to pull some of it out. And there has to be an element of trust in both directions. And right now, we're starting off in a position that you may be too antsy for this to work out well. How do you figure out the equity component in this case? Like how much should you ask?

Oh, I mean, honestly, you think about, like if it's really early stage and maybe they can't give you the retainer yet and you're really helping them really figure out what they need to do, you can go from half a percent to 1%. 1% is a lot. I don't think, because once you go through, you know, dilution and all to 1%. 1% is a lot.

I don't think, because once you go through, you know, dilution and all these things, 1% is plenty. If you're an employee and you're like number 20, you're probably not getting more than a quarter point to half a point anyway. If you're an angel investor, depending on the valuation and how much you put in, you may not get more than half a point anyway. So between a quarter point to 1%, there's a lot there.

Especially if someone's in the C round, you might only get 0.15. And so I look at that and say, listen, if I was working there, I'll get half a point, quarter point. So I need that. And some of you are like, all right, we'll give you a quarter point there, I'll get half a point, quarter point. So I need that. And some of you are like, all right, we'll give you a quarter point. We'll give you half a point. We'll give you one point. So just based on where they are in terms of how much money they've raised in their valuation, you've asked for that percentage. And a lot of times what I found is that quarter point to half a point, most people are okay with, especially if you have a good reputation and you bring something to the table, half a point is okay. You know, people get a little squirmy. Two-year vesting cliff cycle. One percent is like, okay, we're really early.

You're taking a big risk working with us. And sometimes, some founders will just be very honest. Putting your name as an advisor is helping us raise. And you'll talk to the investors, hey, Kelsey, we really want to talk to you. And I try to be very honest. It's like, hey, here's where they're weak, here's where they're strong, and here's where the potential is. And sometimes that does help them raise money. And so for them, 1% is like super fair at that stage where they haven't even raised the seed round and they feel good about allocating it. In this case, there's this guy named Derek Severs. He's in a similar place in life,

meaning financially independent and he had this, I think he had a blog post or something about this where he says, when it comes to startup advising or building something or working on, like partnering with anyone or even speaking in a podcast, the only way I say yes is when I feel hell yes or no, that that's the funder that he uses. Curious how you think about that when new opportunities come up and especially like something like this podcast, we are not paying you

to be here. You're very kind with your time and sharing all this with us what process do you go through to say okay yes i'll do that well if it's like business if i don't like it i i just can't i seriously can't um i remember like i got to meet satya, the CEO of Microsoft. I remember they made an amazing offer to me that Google matched, and it just changed my whole financial landscape. The numbers they put on paper, I didn't believe anyone would ever offer me. It was insane. I thought I was making really good money at Google.

To be honest, I was making really good money at Google, but the Microsoft team was like like but not like this not like this when when was this by the way if you don't mind sharing uh this is like 2016 2017 yeah you joined google right around that time right yeah so it's probably about 2017 2018 and i And I remember I was doing good. I got a couple of promotions by then. I had just speaking at GCP Next, a keynote. And maybe it was 2019. But I did this keynote. And I remember Microsoft team reaches out.

I was like, nah, I'm doing so well at Google. I mean, like, come on. Like, I don't need to do anything at this point. I'm on the right path. And I went down to Redmond, and I met a lot of the leadership team. And nobody asked for no resume. And it was just like, hey, we know what you are. We know what you do.

We know how we think you can help our business. We know what type of impact you can make. And it was really dope. And they gave me this offer. It was so crazy. And I got it back and I was like, these numbers, I don't, this is not even real. I think they're trying to trick me or something. This is not legit. I'm feeling skeptical. And so I remember I was like, I'm going to counter it and ask for more. Just, I don't know why. I thought it was dumb because if they say no, I feel really stupid. And so I countered it.

And the funny thing is, they counter higher. So we're not playing around. I was like, wow, okay. And I went to my manager and I said, listen, I love everything about Google, to be honest. And even in the interview with Microsoft I told them I don't like Azure I like GitHub I like VS Code I don't know about C Sharp

but there are things in the Microsoft portfolio I genuinely like and I can authentically be who I am about Azure is probably not one of them I wish the GitHub team could just redesign Azure to be more like GitHub or something. But there was enough there,

and the numbers were just phenomenal. So I told my manager, I was like, hey, listen, I love Google. I was feeling like, hey, everything seems fair, but look at these numbers. I have to go. It would be irresponsible not to go. And my manager was really nice. He was like, hey, listen, share the offer with me. And I know you're not asking Google

to counter, but I just want to know. I just want to see what they think. And it didn't take long. They countered it with a lot of equity and the equity went up multiple times. So it was the best situation that I did stay there. So I didn't accept the offer. I told the Microsoft team. So in the same day, and people don't realize it, the same day I tweeted this phrase, different company, same team. Because they got me the biggest raise in my life, a different employer. And so I will never forget that, that that's where the biggest bump ever came from. And so I told him I can't come because Google countered it.

And I like Google, and it just felt better. And maybe a year or so later, I got this email from Satya's admin. Like, hey, Satya wants to meet. I was like, you want to meet me? Because with the offer, he wrote this really nice email about the offer and how

he would make sure that I had access to the very top of Microsoft to grow and extend and everything. And they even had the title. It was going to be, I think it was Distinguished Engineer, No More Promotions. And I was not yet even, I was just a principal engineer who had gotten to the step before just a principal engineer sorry sorry sorry no i mean the delta yeah and so i was like man i can

go there no more promotions the money is amazing you got someone like satya sending me an email saying how they're gonna make sure that I have access to all the right folks. And so a year later, I got this email from his admin. And then the admin was like, look, there was a meeting that they had. They talk about executives that they wanted to land, but they didn't. And they just wanted to do some follow up. And so I was like, hey, no problem. And we had just got Thomas Carrion from Oracle.

So I think a lot of people were like, oh, the Oracle guy's coming. Maybe people want to reevaluate their work situation. I had no problem with Thomas because I actually seen him before. I'll tell that story another time. But I knew that he was pretty strong as a technical leader, period. And so I'm going to meet Satya in a couple of days in San Jose. And so the first thing I did was just go buy his book Hit refresh I was like you can't spend time with this guy That's like a whole hour without reading the book So I buy the book

And I just read the whole book in like a day and a half Just go through the whole thing It was a really good book actually Hit refresh Satya from Microsoft And so it's funny I'm in the lobby meeting to the admin I was like hey what's going on with this meeting

Whatever And he told me the whole thing about you know the executive that got away so I'm really excited so I go up to the hotel room and there's like these doors that face like the mountain ranges in San Jose it's really beautiful view and I walk in I remember I was like I gotta I gotta break the ice so it's not awkward I said Sate you knew I was coming all day why are you posing looking to the thing like this is like Vanity Fair photo shoot? Like you knew I was coming. He just started laughing so much.

Because it kind of set up. He was sitting on the balcony. The doors were open. And he's just kind of sitting to the outside looking. I was like, Satya, what are you doing? And so we sit down. I told him I had read the book. And we had a nice conversation about things I could do,

brainstorming ideas. And a dope thing that he said to me was, you know, when we made the first offer, it was kind of like from the mindset of he might be running away from something. So let's give him a strong offer because this might be the right time. But what we should have done is we should have given you an offer

that was more around what to run towards. And there is a difference. And he was like, we didn't necessarily, we don't think we did that. We didn't give you something to run towards. We gave you assuming you were running away from something. And so I thought about it and I still didn't go deep on that one. But I had this integrity thing.

I never want to work on something that I don't believe in because I remember meeting people throughout my tech career, especially when I was doing conferences. There was this one guy. He explained to me, he's like, Kelsey, you know the thing that's interesting about you. When you're on stage, when we're watching, we believe that you believe what you're showing us deeply. We don't think you're trying to trick us. We don't think you're lying. We don't think you just learned it just for this talk. When you present, you present it like with all of your belief and passion that it's hard for us not to also believe and be passionate. And that part, and I was like, damn, now that I think about it, the reason why this all works

is because I have all the other emotional things that allows me to do the right job. And so now when I look at an opportunity, if it makes that connection, I say yes. But also what I've noticed is that I could be walking around San Francisco, and it's happened multiple times in different parts of the world. This kid will come out of the building or restaurant and say, hey, you know, wave me down. I'm walking with people. People are worried, like, hey, I'm just going to get robbed. I'm going to get robbed. And I was like, and I paused, and this person said, hey, you may not remember me, but on Twitter, I asked for some advice and you said you were too busy and I had

to call you on your phone because you were driving. And I call you and you give me all this advice about how to get into tech. I just want to let you know that I'm in tech, I'm working now, and I use all of that advice and I just want to let you know, thank you. So when a podcast reaches out and I have the time, these are real people now, right? These are real people. You don't know what their goals are. You don't know if the podcast is going to do something beneficial to them or not. You don't know if there's something that you're going to say that helps them or one of their listeners. And so it's kind of a privilege to have an outlet where people say, we want you to come talk on our podcast. We're going to do all the hard work. We're going

to edit. We're going to publish. We're going to share to our audience. To me, there's a lot that goes into that. When someone asks you for career advice, they're literally asking you to help them be successful in life. And if it works, like that person I was in the very beginning of my career, hoping that I would run into people who would help me along the way, knowing how important it was to kind of make a little bit more money so you can take care of your family. When I look at some of these requests,

that's all I see. I see this person trying to figure it out and you get the privilege of being able to either help or hurt. That's what you get to do. So when I say yes to things like that, I'm thinking like, hey, how does this snowball down the road? And so it makes it real easy to say yes to people.

Now, when it's business, you got to put a lot more into it. But when it's people, I don't care what your title is. I don't care how popular you are. I don't know. It's just an honor that you would give me an opportunity to do that. So I would try to return the favor. Oh, you're very kind. I was mentioning this before we started recording that you were also the first person to say yes to be a guest on our podcast. And this is back in, I think, October 2020. We didn't even have a name, by the way. We didn't even have a

website. We just reached out with an email saying, heysey would love to chat about this thing and you respond i think in like two days less than two days i was in boston at the time and i was going from the airport to my airbnb and i i got your email and my wife was sitting next to me i just showed her the email i was like holy shit this is real uh we don't have a name like we got six weeks to figure this out and literally that's that's where it all started you don't know what it is it's such a privilege to be a part of people's like origin stories Like we got six weeks to figure this out. And literally that's where it all started. You don't know what it is. It's such a privilege to be a part of people's like origin stories. You got to remember that story you just told will never happen again because it can't. And in someone's timeline, you get to say that you've kind of nudged the trajectory just a little.

It doesn't have to be a lot. But just to be in the position where you can literally be a part of someone else's storyline come on how's that not one of the most exciting things you can ever do uh it definitely nudged our storyline quite a bit because a lot of people we reached out to next also came on because they say they saw your name on our website they're like oh you spoke Kelsey? Well, he's really cool. Well, we'll speak on your podcast. Yes, can't thank you enough for helping us get that start.

And I'm sure we aren't the only ones who you have helped with. There are many others too. And a lot of us look up to you, Kelsey, not just as an engineer, as a technologist, but also as a human being. And you bring your authentic self even to this conversation. Like a lot of things that we have learned about you today. I don't think I ever knew about any of these things before. And I think it takes courage to be this honest.

It takes courage to be this authentic and share what you know of in life. And yeah, thank you for being the person that you are. honest it takes courage to be this authentic and share what you know of in life and um yeah thank you for for being the person that you are uh i don't know what else to say stop making me cry a lot of people look up to you um and you've inspired a lot of people's lives are there people around you or either today or in, in your previous experiences, um, who inspired you or people that you look up to?

Yeah. I mean, you know, just starting with like your parents, you know, when my mom got divorced and she had to be a single mom from like, I would say at least 14 or probably 13. And you realize like what goes into that.

It's a lot to take care of the whole house. And you got two sons and you got school clothes to buy and they want fancy clothes and you just don't really make the kind of money to buy all the fancy clothes. You got to make it work. And they never tell you how hard it is. They just make it work. They figure it out and they make it work. And they never tell you how hard it is. They just make it work. They figure it out and they make it work.

And when I got my first job, I was so happy to be able to buy my own school clothes because I understood the burden that was going to lift for my mom. So through that action, you kind of understand like, if I can just be as strong as this person, if I can be just as responsible as this person, a lot goes into it. And then, you know, as a kid, I kind of watched her work ethic of like

learning new skills, getting jobs that she wanted to get. I was like, yeah, okay, this is like the blueprint, you know, that's the phase. So you kind of got to honor that, you got to respect that. And so, and honestly, you probably never even give it enough credit. Like, it's so easy to say, I look up to this person that I've never met, that doesn't know me. You know, that's easy because you don't really know the details of this person's life. You just see the good parts. So I think we do as general, we do kind of take for granted like the people that are immediately impacting our lives all the time. And so I think there was a point in time where I started to understand the value that she was bringing to that equation. You kind of start with the parents, and then you kind of move on to your friends that keep you honest.

I have some friends that I call. They think everything's a bad idea. They're like, I don't know. And so you have to work hard to convince them that this is the right thing to do. I know what you're talking about. Yeah. But you like those folks because what they. I know what you're talking about. Yeah. But you like those folks because what they do is they keep you honest.

Yes. They're not going to blow your head up. They're going to try to keep you as grounded as possible. And you really have to explain in detail why you're trying to do what you're trying to do. And they give you that perspective. And I just look up to people who can be honest. It's so easy just to try and make people hear what they want to hear. And so you need that collection of people because you don't succeed by yourself. All these inputs are like required. And then when it comes to like the technology piece,

I remember when I did my, one of my code reviews to Golang and it was, I was just adding basic off support to the standard library. And so to make that easy, you just want a function that says like dot basic off that will retrieve the username password because dealing with that, extracting it from the headers yourself, it's just tedious. So let me just add it really quickly. So I added it. I made all the tests. I was ready. I like Golang. Their code reviews are pretty strenuous, especially coming from a lot of the Googlers there. I wasn't working at the Google at the time. So I was like, let me make sure that my commit message is nice, my unit test, everything is perfect. And then Rob Pike does my review.

I was like, oh my God, Rob Pike, this dude is legendary. And it's this long review. He was like, hey, you can't allocate bytes on the stack in the path of an HTTP request because you're going to slow everything down. So do not use, you know, some of these methods you're calling. You need to be working at the byte level so you don't allocate. It needs to be fast. I'm sitting here like, I don't really know what that means. Like, I don't, I don't, I just thought I was using the things the right way. And he was very patient.

He went in so much detail about what all this stuff means and everything. And so I go do my research and I fix it. And his code review, as you can tell, he teaches people in his code reviews. He's not there just to nitpick and make sure it doesn't get in. He's trying to educate and train. And so when I started to look at that class of engineer,

the Rob Pikes, the Brad Fitzpatricks, there's so many of these type of engineers that are really, really good at what they do, but they have a way of making other people better. And so when I zoom out, I've always had engineers like this. When I was in that financial institution, there was a guy named Dan Marchant. He was that guy for me, right? And so throughout my career, there's always someone who takes the time to extend their knowledge. And that's why I started doing that myself. I got to teach everybody everything I know.

So I started to mimic those folks, learn more, and then teach it to others. But I actually get inspired by regular, regular people. I'm one of those people that like that feeling where you watch a movie and it makes you feel a certain way. Like, you know it's a movie. You know they wrote it into the script. You know they did it on purpose. But I allow my emotion to come out anyway. Right?

Where someone does something counter to their character that's inspiring. Maybe they sacrifice themselves for the bigger cause. I like that. And when you think about, like when people say you're retired, and the only reason why you can do that in modern society is because you have money. And the people who are still willing to accept money, like to pick up your trash, purify your water, keep everything going, that means that they're the only reason you can retire. It's because this money thing that you've accumulated still has value. And so for me, it is, I do get, I look up to those people because they do these jobs

that some people don't want to do. You look at people that are really good, like you call someone to do a job and like, man, I've never seen someone fix something that fast. Like they're an expert at their craft. They have all the right tools. They come in and do a good job. It's like, you know what? I need to make sure I can do a good job when I'm doing any job as this person. So I try to find inspiration in the smallest corners of the world. And I just remind myself. So sometimes I just go to YouTube to get the reminder, right? Sometimes you just need that reminder where you see someone on the street and they say, hey, you're homeless. How do you feel? And then that person says, but I'm alive

though. You say, oh, wow. Okay. You're alive. Some people are not alive. There's billionaires that's not alive. So the homeless person's like, yo, I know I ain't got very much, but I'm alive. And now that's a little reminder. Or I see kids dancing in some of these countries where, you know, they ain't got no infrastructure. It looks pretty bad conditions that most people would not even dare to dream to live of. But then what they're doing, though, is they're so happy in the moment they're making this video for YouTube.

And, you know, they're bringing like, you never seen a person happier. Like what type of person can find the ability to be happy in those conditions? So there's a lot to learn from that. So I try to make sure that when my flight gets delayed, I don't become an asshole and start being mean to the people at the counter and blaming people. You just say, you know what? The fact that I can fly instead of drive to that destination, the fact that this flight is probably going to land safely, let me just chill out. Maybe I just play some Magic the Gathering online for three or four hours.

Life is not terrible. Just sit here and chill out. And so that's what I try to do to make sure I stay grounded. Well, you're definitely a very humble person. By the way, whenever I've seen you talk at a conference or like even in this conversation, you come across as a very confident person. Have you ever been nervous? Like, for example, this meeting with Satya Nadella, for example, were you ever nervous going into that meeting? Well, I wasn't nervous going into that meeting because there was a point in my career was like, listen, it don't matter anymore. So, there's two extremes that happen. There's two things I watched that really helped me kind

of get to this kind of conclusion. And so I'm not a very religious person, but I grew up in the South and that's a lot of Christianity there. So it took a lot for me to read a book from like the Dalai Lama about, you know, their side of the world and how they see kind of these things. I remember just reading to it and you started learning about like Buddhism and all these things and you go deeper into this thought of, you know, the things that people need to feel like they're alive is different as you kind of progress. Some people really need things that they can touch and worship. And then some people move beyond that. And some people you can tell them nothing matters. Like the universe is this big place. I remember watching like whatever that documentary with Neil deGrasse Tyson when he was like, this is the earth.

And he zoomed out and showed all the galaxies. It's like our galaxy is this little tiny, like not even like a grain of salt. And then he showed it like in this big thing. And I was like, wow, you can see that and fall into deep depression. Like, wow, we are so insignificant in the grand scheme. But when I thought about that level of insignificance, it's like it took pressure off. Being number one on earth means what in the universe? What is it?

You're number one on earth. Does that mean you're number one in the universe? Does it even matter? Like, do you think the stars care if you're number one in Python? It doesn't matter. Like, literally insignificant. I'm not saying you can't find any joy in that. I'm just saying is that it's not the end of the world if you're not. So for me, it took a weight off of my shoulders. I don't have to do or be anything to anybody. That's it. So great. Instead of worrying about what Satya thinks about me going into that meeting, I already know that I found myself. I know that I'm able to do certain things throughout my career. And so he's done a lot with his life,

which is great. And he's also a pretty humble guy too, when you talk to him. And so I just said, you know, there's this phrase that some kids get taught when they're growing up, you're not better than anyone and no one is better than you. And I like that idea because you don't have to treat people below you a certain way. Oh, you're just this guy. Let me just treat you differently. But then you might also get to the conclusion that you're not going to treat me different either. And I'm also not going to treat myself different in light of that. So that's the way I kind of thought about and approached that whole thing around that. So the confidence is from I don't have to be the best.

So I'm confident being at whatever level you rank. Some people say, Kelsey doesn't give great talks. Okay. I mean, what does that even mean? Should I just stop talking now? Like, hey, good feedback. I might even be curious and say, why do you say that? And then I might listen and

say, maybe there's a piece in there that helps me. But was that, it's like, did the universe form and I was born to make this one person like my talks? No, that's not how that works. So I find confidence in the feedback loop. So when someone says, hey, that talk really helped me in my career, I remember that, I remember that. I put that there. And I know it's at least working for some people, maybe not all the people, but that isn't the goal. So now I can walk around. I guess confidence is the right word, but I try to be careful to make sure it never turns into arrogance.

Well, if anyone told you that they didn't like your talk i think they should go update their taste uh personal opinion personal opinion uh kelsey this is this is this is awesome uh we we are really enjoying talking to you uh just want to ask is there anything else you would like to share with our listeners no i, I think it sums it up. And I think the key is if you can ever find comfort in just being, and it's hard to say be who you are, because I think there's also work that goes into who you are. Who you are may just be the product of your environment. It may be shaped by all these inputs. But if you can find the time examine what those inputs are

right is this really your favorite sports team can you not just enjoy sports by just watching people try to overcome human limitations do you really need to get that promotion from that one job or is the world a really big place and You can decide where you take your talents and just grow over there if this is cut off to you. And so I just hope people realize that you don't necessarily have to compare yourself to other people, but if you do, hopefully you understand how valuable you are as you are.

There's a lot of value into this one situation you've been given, no matter what you believe. And ideally you try to make the best of it, but. And ideally, you try to make the best of it, but it doesn't mean you have to be the best at everything. So hopefully, that's the takeaway from this, you know, time we kind of spent together thinking about discussing these things. And so hopefully, people find a little bit of motivation in that. Hopefully, it lifts a little weight off their shoulders and gives them a little bit more freedom to do the best that they're capable of doing.

That's beautifully said. Kelsey, thank you so much again for taking this time. As always, you're very humble and very kind and very empathetic, teaching us all a lot of things beyond just technology. And we all thank you for that. Awesome. All right. Later. Thanks so much, Kaufi. We would love to hear from you. Until next time, take care.