Changelog Interviews – Episode #595

Retired, not tired.

with Kelsey Hightower

All Episodes

Kelsey Hightower is back to share more of his wisdom. This time it’s one year after his retirement from Google. But guess what? He might be “retired,” but he’s not tired. In this episode Kelsey shares what drives him, what he fears, and how he thinks through his life choices and parenting. This is a good one.



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Notes & Links

📝 Edit Notes


1 00:00 This is The Changelog 01:30
2 01:30 Sponsor: Sentry 03:39
3 05:10 Start the show! 02:08
4 07:18 A morning in Kelsey's shoes? 04:14
5 11:32 Bidets, totally worth it. 03:38
6 15:10 How does consulting work for you? 02:56
7 18:05 Fractional CTOs 01:26
8 19:31 Give me the story 03:25
9 22:57 Simplifiying complex ideas 06:43
10 29:39 Sponsor: 1Password 04:52
11 34:31 What's Kelsey into? 04:59
12 39:31 What do you fear? 07:54
13 47:25 American Psycho flying commerical 04:50
14 52:15 Podcasting is powerful 07:15
15 59:30 Entertaining conspiracy theories? 09:15
16 1:08:44 Sponsor: Cronitor 01:26
17 1:10:11 Are you raising chickens? 05:10
18 1:15:21 Do you give bad advice? 04:52
19 1:20:13 Becoming wise 07:59
20 1:28:12 Wrapping with a mic drop 01:44
21 1:29:56 There's a bonus! 00:37
22 1:30:33 Ok, this show is done. 02:51


📝 Edit Transcript


Play the audio to listen along while you enjoy the transcript. 🎧

We’re back with - I would say you’re a good friend. Would you say you’re a good friend now, Kelsey?

Yeah, I’m a friend of the pod at this point.

I think so.

What about a friend of me, of us specifically? Are we friends?

Yeah, we cool, too. I talk to y’all when I see y’all in person.

That’s right.

Alright. Well, almost exactly to the day… Almost. Like a few weeks shy, we did a show with you that was called “Even the best rides come to an end.” And that sounded kind of negative, to some degree. Your retirement was unexpected, people were thinking maybe you won’t be out there… But you’re out there, and you’re doing stuff. I even saw a tweet the other day saying “I thought you retired”, and you’re like “Nah. I didn’t retire.”

No, you said “I’m retired, I’m not tired.”

“I’m retired. Not tired.” Exactly. Thank you, Jerod.

Yeah, I think this is idea that the only way to do stuff is to have an employer, and they list out the things they need you to do, and you go in there from nine to five, and you do those things. And the idea that you could be self-directed, the idea that you could come up with your own list is foreign to a lot of people, and I understand why… But I think in this tech game there is a lot of value in those that can just explore the things that they want to explore, and kind of detached from that, if possible. So I’ve found it to be possible, and yeah, it’s been almost a whole year. I still do the paid keynotes, I still advise the tech companies that I’m most interested in; companies come and go, and as those new companies come around, they still tap in and say “Hey, we’re trying to bring this thing to market. You have a lot of experience, especially with our audience, what we’re trying to do. Can you help?” So what you find out is that you’re still relevant in those circles, right? It doesn’t all go away just because you left your employer. And so what is work? And I think that’s the real question… What is work, and what type of work do you want to do?

Do you have just numerous opportunities on your table? Is it lots of no’s, a few yes’es? What’s it like to be a morning in your shoes, so to speak?

Yeah, a lot of no’s.

But you said yes to us.

A friend of the pod, man…

Yeah, but y’all like fam. These podcasts are important, because when I know people out of the blue, they’ll say “Hey, I was in the gym, and I was listening to a podcast. And you said something that really stuck with me, and I just wanted to reach out and say thank you for saying that, because I really needed that.” So these podcasts are important, because although I love to speak with you all, we’re always speaking through the camera, we’re always speaking through the speakers. There’s always someone on the other side. And when I was starting in tech, I was like “Man, if people would just share a little bit more, just a little bit more, it could probably shave a bunch of years off my timeline.” So I still do those. So saying yes to things that I know have good outcomes… You all are so good at this as well. It’s not like I have to edit the podcast; you’re highly professional, you ask really good questions…

So those are easy yes’es. The no’s are “Come speak for free, halfway around the world. Go buy a flight, purchase a hotel and do it for the community.” It’s like “Hey, guys…” I don’t need to be paying to speak at a conference. I don’t have anything to sell anybody, there is no really reason for me to go and do a bunch of work for free. So those are the easy no’s.

So you settled in now, it’s been a year, you’ve probably found what’s working, what you like, what’s not working… The freedom is free, but it also can be constrained, because now you’ve got to decide how you’re gonna spend your time, and on what. Just curious, have you settled in? Do you feel comfortable? Do you like this lifestyle more? Are you thinking “Well, maybe I’ll try to start a new thing and become a businessman again”? I know you’re a business man, Jay-Z style, but you know, like a traditional businessman? What are you thinking? How are you feeling about that now?

That pressure comes with societal pressure, when you have to tell people what do you do, and you have to have a good answer, that they want to hear. That pressure comes from maybe you need that private jet and you don’t have one, so now you’ve got to figure out how to get a private jet. So een if you’re like $50 short of the private jet, you can’t sleep at night, because you can’t afford the private jet. So I don’t have any of those. So I don’t need anything to pop, I don’t need the next startup to go IPO… I don’t need any of that. So when that goes away, then you just do things you think are worth doing. For example, I bought some bidets from TOTO. My wife’s like “I want a bidet.” I said “Let’s get a bidet.” It turns out the bidet needs 1400 watts of power. You can’t plug that into your normal outlets for you, because you’ve gotta make a choice. Do you blow-dry your hair, or use the bidet? If you do both at the same time, the breaker will trip. So I learned how to run a wire, and got my permit, and ran a wire from the electrical box, through one floor, through the attic, stapled it across the attic, all electrical codes, ran 20 amp circuit, got the breaker, all the protections… And that was a whole project. And it doesn’t need to be put on GitHub, it doesn’t have to become content… It’s just a thing where I learned a whole bunch of things that tradespeople go to school for, and I learned how to do this new thing, and that feels good. I have this new skill. I got a bunch of new tools in the tool bag… It feels like when I was learning tech for the first time. I’d never logged into a server before. I might break something. So how do you do this properly? How do you do it safely? Should I really leave port 22 open? So it’s like getting to relive that, and again, this is not like “How are you gonna make money running electrical wires?” It’s like, I don’t need to be an electrician to learn this particular skill. That’s what it feels like.

I can say yes to stuff. Hey, my friend’s having a birthday party. It’s gonna be lots of dancing. Before, I could have been like “Hey, I’m little too busy. I’ve gotta take a flight somewhere. I won’t be able to make it.” Now I can just say yes. I don’t even like dancing that much. But now I can just say yes, and just go and enjoy the moment. I’m not thinking about unanswered emails… I can be present. So that’s where it’s like “Hey, I have a little bit more room to do stuff that for a lot of people doesn’t matter.” That’s great. I love that part.

Now, I don’t want to linger here too long, but bidets - totally worth it, or not worth the effort? What’s your review?

Totally worth it. I mean, if you think about it, the sales pitch for bidets is that everything else we clean with water. You wash your car with water; you take a shower with water; you brush your teeth with water. But the only thing we do in some societies - because apparently, a large portion of the world uses bidets as cultural things from a long time ago. But this idea that you’re going to wipe with this two-ply; some of y’all out here on that one-ply, getting your fingers dirty.


[00:12:04.18] You’re going to wipe a few times, and throw it all in a toilet and then flush it. And then you know you ain’t clean. People will think back to the teenage years - hopefully this is not the case for you beyond your teenage years… You look at those underwear after you take them off, you’re like “Hey man, I haven’t been wiping thoroughly.” So that bidet, that whole experience of using water to also wash down there changes like what it means to be clean. So for some people, you go to some countries and you say you don’t have a bidet, they’re like “What are you doing? How are you cleaning that?” So I think it’s worth it, it’s been worth it… I don’t know if it was worth it to get the addition that I bought, that uses all this power…

I was gonna say, it was a big project.

Yeah, but it’s definitely something I think people should look into from a medical device/cleaning device in the house.

I don’t want to bust your bubble and I’m glad that you had the opportunity to say yes, and to learn electrical, but there are alternative options for bidets, that are like 100 bucks.

Yeah. And they don’t have hot water, they’re cold… [unintelligible 00:13:04.25] And I tried one. Like, you go get one of the ones for 100 bucks, they totally work. They’ll spray water on you… And you better hope the temperature is good, or you getting a rude awakening. So there’s levels to this. So the ones that have –

He did his research, Adam…

Yeah, yeah, yeah. You can go get the $100 one and call me in the winter. [laughter]

Maybe not.

Wise words.

So I know this because I have a friend who’s like swearing by a bidet, just like you are, and he’s like “Listen, you don’t have to go and do the whole - what you did. You can just get this one thing. This is what we used. We love it.” And they’re a neighbor. So I was like “Okay, great.” I didn’t consider the temperature of the water, although we do live in Texas and room temperature is usually in the 70s… But 70-degree water is different than 120-degree water. Or maybe 110. 105.

I think most people are fine with the manual thing… But here’s the thing. You’ve got this manual hose, and if you get your technique right over time, you’ll probably make less of a mess, for sure.

Right. Technique.

But when you start to see – look, we’re engineers. When you walk in and the toilet seat opens, the nightlight comes on, [unintelligible 00:14:13.18] This thing aims perfectly… You hit the little dryer button…

You’ve got a Kelsey switch on there, and then you have a wife switch, maybe a kid switch… Do you have settings?

Yeah, it has four programmable modes.

No way. So it’ll angle it?

It angles, etc. Everything you need. And so it’s one of those things where it’s like – some people say you’ll save some tissue, some people… It’s just a thing that that’s where the tech is.

So the tech is at that point where you’ve got levels to this. You can write code using Pico, or you can use VS Code. It’s up to you. They both will get the job done… But there’s some advantages to having a few more functions and some automation.

Right. I almost want to go one more TMI layer deeper, Jerod. What do you think? Should I go to TMI deeper?

We don’t gotta go deeper.

I don’t think so, man. This is deep, man. We already did the tech analogy, and everything. It’s all good.

Okay. Alright, we’ll leave it there then. So I’ve gotta imagine then as part of – do you want to linger here more in the bidet area, Jerod?

No. No, I do not.

Okay. I know you said you want to linger for a second, and just in case… I didn’t want to deviate. Okay, so you’re consulting for companies, implementations… Give me an example of how that plays out.

So I’m very careful… I am that anyone’s consultant. I’m not writing no code, I’m not producing no content, I am not doing anything that your team could be doing. Advisory is totally different. From a legal perspective, advisory is different. And the advisory work is literally to advise. So for example, if you’re Red Panda, and you say “Hey, Kelsey (the founder over there, Alex), we want to expand beyond Kafka.” I’m like “Look, Alex, Kafka is great. You can go out and compete and do drop-in replacements for the Confluent crowd all day.” But then there’s another wave, another generation of people who don’t do streaming at all, because it’s too hard. And if you go tell them they’ve got to go down with a Kafka client to do anything, that’s too much.

[00:16:11.22] So what do we need? We need an HTTP interface, we need something that can integrate with Next.js… We’ve gotta lower that bar way down without giving up the potential power. And here’s how you roll it out. Here’s how you do it over time. This is what the price point’s gotta be. You’ve gotta make sure that it can run on prem, maybe you start with a managed service… And maybe you’ve gotta tone down the enterprise angle to get some of the Heroku type onramp, where it’s like “Oh, this is just the easiest thing to do to pass messages around.” You go look at the ecosystem… What parts are you missing? That coupling looks like they have what you need; what does an acquisition look like? Maybe you don’t acquire that particular company.

And then the accountability on the advisory side is that when they make these moves, if you’re going to be an advisor more than a year, then you’ve gotta have results. It’s got to be like “Hey, we did that thing. You had the trust of the engineering team, you had the trust of the sales team, you had the trust of all these teams.” So that’s what the advisory is. Hey, we’re having trouble selling the product. How is it priced? Let me see the email conversations. You can’t talk to people like that… You have to give them guidance on like “How long is this going to take? How much is it going to cost?” I know you want to sell product [unintelligible 00:17:15.25] Either you’re going to do it, or a third party is going to do it.

But these are like the advisory things where not all companies can go hire a cool executive team that has decades of experience, that knows how to do these things. So if you’re a founder, having a second pair of eyes, or a third pair of eyes who can kind of give you a somewhat non-biased feedback loop, it’s important.

So that’s the type of work that I tend to do when it comes to the advisory stuff. So that’s the stuff that I still like doing. Writing code is not what I want to do for money, at all. There’s enough people in the world that are doing that. I’m just trying to make sure that the experience that I’ve built up over two decades has somewhere to go. I just don’t want it to go away, and the best outlet has been helping the next generation of companies do their thing.

This reminds me of a term I’ve heard recently, which I don’t know much about, so maybe you can school me… But it sounds a lot like what they’re calling fractional CTOs. Are you familiar with this concept?

I am. I mean, I think that’s also cool. Some people have fractional assistants… You just need help sometimes making decisions. If you think about a founder, if you’re a solo founder, maybe there’s two people, and let’s say you start to get 10 people. There are CTO-like responsibilities you’re just not going to have time to do. So some founders would rather focus on like sales, and growing the business, and hiring… But ho makes the CTO-like decisions? The struggle part about this though is that these are big, long-term decisions. So if someone is only coming in for a fraction of their time… Y’all know how this works. It’s easy to drop in, give advice, and then dip. That’s really “Hey, you guys are doing it wrong” maybe do it better, and be out.

We may or may not do that on a weekly basis, Adam… I don’t know.

[laughs] So on the shows, we give advice, and then we go the next show.

I think we’re very fractional. I agree.

If you’re a fractional CTO, you might come in and say “Hey, here’s how you lay out your two-year plan for spending money in the cloud. Here’s how you negotiate discounts.” You wouldn’t believe most people don’t know how to negotiate a cloud contract. So you can hire someone that can save you 30%. That’s a good deal. Maybe you’re not ready for a full-time CTO, so you bring in someone that has that function… Some people just need an outbound CTO that could talk to customers. “Hey, this is what we’re doing. Here’s the vision. Here’s the story.” Maybe you don’t have anyone on your team that can do that.

My advisor is more like “Kelsey, we’ve seen your work. We know what you do. Your credentials are valid for us. We can’t afford to hire you though. But we would love some input on what we’re doing. We’ve got developers, they do a good job, we have some serial founders, they do a good job… But we’re missing something.” And sometimes it’s as simple as “Give me the story.” And I’m like “That’s not the story.” And I play back the story for them, and they’re like “We never positioned what we were building in that way”, and they go test it with customers. They go test it at the conferences, and they come back like “Kelsey, people get it now. We’re going to rename the product. We’re going to make a little pivot on how we approach this.” How much is that worth, if you have only two years of runway? If you’re out here telling the wrong story for a year and a half, you’ve only got six more months before it’s over. So getting the story right within three months means a lot.

[00:20:19.02] I’d rather people understand what we’re doing, and they just don’t want to buy, versus they don’t even understand what we’re doing, so we can’t even get to a conversation about what to buy. And that is surprisingly big for a large set of companies that are out here, that no one knows what the hell they do, and they run out of money before they can help them understand.

Yeah, we face that a lot, because we tend to work with earlier stage folks who want to come to us for really awareness. “We have something, we need to test it…” Sometimes they come to us premature even. And they know that. And I’m like “What are you getting from this engagement with us? We’re a podcast, we obviously have ears around the world, and we want to share your story in compelling ways… But you don’t even have product-market fit. You’re not even sure where you’re at… So what do you really gain from–” And I ask them these hard questions, because I’m not just trying to sell an ad. I’m trying to sell someone who is a long-term partner and we can truly help. And obviously, the conduit is some version of sponsorship, some version of ad. But I’m like “I don’t know if we can help you.” And then they’re like “No, you can, because we just need to have people come talk to us about where we’re currently at, and that’s all we want.” I’m like “Okay, great, I guess we can do that. So… Cool.” As long as you know what we’re doing here, and you’re not bummed out when you don’t get conversions, that you just get eyeballs or interest, that maybe 99% goes away, then okay, I’m cool with that, because I want to sell you value.

It’s unfortunate that that is what they believe the game to be… Because this worked for so long. Like, the old game was “Just get popular enough, give away the product. Maybe you can’t even sell the product, but give it away, and maybe someone will buy you who believes they can sell it.” So for some founders it’s literally just “Get the word out, get the logo poppin’, get 1,000 free signups and unload this thing before anyone finds out you can’t sell.” And there’s been a lot of exes that have worked that way. But the truth is these days [unintelligible 00:22:10.14] is a little slower. People aren’t getting that round A, that round B. And so now they’ve figure out “I have to actually sell the product.”

So I tell a lot of people, “You’re not ready to make no noise. The product is not usable. I’ve tried it. You can’t actually do anything with it.” And maybe if you’re listening to this and you’re a founder, you don’t get to make noise two or three times. First time you make some noise and I pay attention and it’s nothing. The next time you make noise, I’m like – I might look again. After that, it’s like “Dude, I don’t think you understand what’s happening here. You’re wasting your shots.” So use them wisely. If you’re going to spend all this money on outbound, when people show up, have something that they can do.

I think what you do well is you take complex scenarios, frameworks, stories even, and simplify them. And you’re a very story-driven and packaging-focused kind of person, from my understanding. You take very complex things and distill it down into ways, which has been a hallmark of your career, is being able to do that consistently. Not everybody can do that, right? I mean, that’s a skill, or maybe a birth talent. You got it at birth. And you’ve just learned you had it, and you’re charismatic, and you can share a story, and people listen to you… And you’ve got aflow, right? You’ve got a flow to your voice. And so people find that interesting, or… I don’t know, soothing. Pick a word, right? Mellifluous. I’ll share it with you.


Right, compelling. You have a way of taking what seems to be very complex or disjointed, simplifying it, connecting it and sharing it away and packaging it in particular in a way that people get and understand, and can get excited about.

[00:23:59.13] I’m going to take a moment and appreciate the compliment.

Take it. Take it.

But I think the thing is people are born – that’s a human thing. It’s a societal thing for hundreds if not thousands and thousands of years. Humans do this by default. This is what you do by default. When you’re nine years old and you go outside and you get bit by a little rodent, and you come in… Notice how kids tell that story. “I was outside, playing, and we were just climbing trees, I promise. And I climbed a tree, I slipped down, and… I mean this thing was big as a giraffe, and it just bit me. And I can’t believe I survived.” And they start crying amidst of this, because now they’re flush with emotion, because they’re reliving the experience. But in a professional setting we’re told not to do that. We’re told “You’re not a person. You are a Linux system administrator level three. You do TerraForm, Linux, maybe F5 from time to time. That’s it. Those are the three bullet points. And when you come into work, we want all interaction with other humans to be via JIRA tickets. You get a ticket assigned to you, you respond to the ticket within this timeframe… That’s it. And then every once in a while, every quarter, we’ll tell you how good you are. That’s it.”

And so you rehearse that. You become that. So when it’s time to talk to actual people, you don’t know how to do it. Your manager relationship is “My boss. My boss told me to do it. I don’t look back. I do what they tell me, because I need this job.” So you have no practice at actually being a human being. It goes away at some point.

So what I ended up doing, luckily for me, when I found the courage to let the slides go, when I found the courage to let the speaker notes go, and I’m just talking to you, just like you talk to your family, right now and every day… Some people are like “Well, what is he doing? He’s not doing the stuff that we’ve been taught to do. He’s speaking his mind?!” It’s not about just facts, there’s something about experience plus facts equals opinion. So my opinion of this thing - “I don’t like it for this reason. I like it for this reason.” You can disagree, but at least I’m giving you something to agree or disagree with. That’s not the norm. The norm is “I’m going to do this talk just like a website. I’m just gonna put everything on the slide, and read it back to you. And as long as I don’t mess up too much, or as long as I don’t fall down, you’re gonna say “Good talk.” What?! Who gave the talk? I don’t remember the name, but I think they were talking about Agile. What is that? That’s not natural.

And so I think the storytelling part is – and I’ve seen a lot of people get very far in the career by being the magician. “I can do something no one else can do, so they need me.” And so you build your career around this mystery. “I’m the only one that can write code. I’m the only one that knows how to deal with the Solaris box.” So you go real far not writing docs, not explaining, not training… You’re just the go-to person. And most companies don’t even care about that. They’re like “Dude, I call the plumber. You can be the go-to person for the plumber, because I have no interest in touching the toilet.” So yes, I don’t care about your trade, do what you want to do… And yeah, there’s a bit of job security in that… But that part where you actually can explain it to someone, meaning - for me, I need to understand it in simple terms. Like, when people start thinking about AI stuff, “Oh, AI is going to take over the world”, and most people are like “I think it will. Maybe I’ll just wait until then and see what happens to me.” And that’s how they navigate that space. And if you’re selling AI right now to that group of people, all you have to do is just keep the show going. “Hey, look at this thing. It’s smarter. It can do all these things”, and they’re like “Oh, man, this magician is amazing. I love it. I trust it.” So hey, if they don’t understand, they’re not asking questions, we’ll keep this party going.

Then someone shows up and says “Hey, guys, let me show you exactly how it works. Here’s where it breaks, here’s how you fix it, here’s what it’s actually doing underneath the covers.” Now, once I do that, I can’t sell you the same thing at the same price. Like, “Kelsey, now I know how to do it. Why would I pay you a premium for that thing?”

[00:28:00.17] So I’ve gotta add some more value than mystery. But the thing I do like about it though is it makes people feel more comfortable. So when they do hear the story, and they still need it, it just makes sense. It’s like “You know what, now that I understand it, maybe I could even do it myself. But I don’t want to. This makes sense to me.” And I think a lot of our customers, if you’re out here and you’re in business, I’d rather have a customer that understands the value that I’m giving them, than to be afraid of what happens if they didn’t buy it. Because once someone comes in and finds out, the gig is over. Once people pull back that curtain and find out that there’s not much there…

I remember some people thought you could only use Oracle in business. Then someone pulls back that veil and says “You know what - Postgres can do what you need.” Now what? And so that’s been my thing, and I just love being able to explain it. And the reason why – and it’s the last thing I’ll say here, is when I’m learning anything complex, you know that wow moment you get when you understand it yourself… I just replay that back. I like the way that feels. So I go back and I do the same thing. I pace myself in a way like – I’m not just gonna give you the answer, because that would just be too boring, and that’s what websites do. What I like to do is like “Hey, you know, this thing you’re trying to do, here’s what it looks like. And you know how when it breaks like this, and then we’re all stuck? Let me show y’all something.” And then I show it to them, and then I reverse-engineer so they can see how it works too, and then everyone feels good, just like I did when I learned how to do it for the first time.

That’s a good formula. I like that one.

Break: [00:29:28.05]

So you have complete freedom now, to learn, to explore and you only have to do things you want to do. That’s amazing. Tell us about things that aren’t electricity, or bidets, or plumbing, or house projects, that have you excited, have your interest, have you trying to peel back the covers and see how they work. What are you into right now? …because it’s got to be pure, right? You don’t have any reason not to be into it.

Well, here’s the thing… So one thing people don’t talk about when you retire with all these things is what are you afraid of? What are you afraid of? I’m not afraid of the job, I’m not afraid of a project failing… So what are you afraid of? What’s left to be afraid of? And now when you have a little bit more time to pay attention to what’s going on, all this stuff that you had, that like lets you retire… So what does it take to retire? Usually, for most people, it takes money to retire. So that means money still needs to be working. Money still needs to work in order for this to work. If we get hyperinflation, let’s just say, now the minimum wage is $200 million, I don’t care what your status is, you’re now back at a reset. McDonald’s starts saying $200 million an hour. [laughs] I don’t care how much money you have right now, it doesn’t matter, because the whole thing has gotten reset. So I have a fear of not just like societal collapse, but a reset that you can’t deal with. And as you get older, you may not be able to bounce back into that reset. So that always has me on edge of like “I need to pay attention.” I still have to keep my eye on the prize… And also, I actually care about how people are actually doing.

So stock market is way up. If you own stocks, your world is fine. Like “Hey, everything is great.” But then what are you going to buy with that money if the people you’re buying it from are in good shape? Like, if your doctor is not in a happy place, that’s not good for you. If your neighbor is not in a happy place, that may not be good for you, because that neighbor may be your teacher, it may be the firefighter, it may be the person that works at the utility plant, keeping your water clean… Those people need to be in a good spot as well, for everything else to work.

So I think for me, I still respect the dependency I have on people that I’ve never met. And if those people are in a good spot, then I still have things to think about. Like, how do you solve that puzzle? So we just ignore it and hopefully it fixes itself? Or should we try to use the same type of brainpower we did to build apps, and cloud, to think about people and society?

You must think about inflation a lot then.

Not to the point where I’m paralyzed by it, just at a point where I’ve just got to look at the meter. Just like when you’re in ops, you’ve got the dashboard up, and you know you’ve got disk space, you can probably buy more, and there’s things you can do to clean up the disk space, but you’ve gotta at least have the graph up, so you can know where the red line is. So I have the graph up, I’m trying to pay attention to the red line, and I’m trying to understand what it actually means.

So what’s the hedge? The hedge is having equity in lots of new companies. The hedge is having a paid off house. For me the hedge is learn some new skills. A lot of people think these tech skills are going to be around forever. This idea that in tech we get paid a lot of money. But it doesn’t mean that’s going to always be that way. There’s nothing stopping tech, at least right now. In many parts of the world tech is not the highest paid profession you can do.

[00:38:08.25] So I think a lot of people in certain societies don’t realize that what we’re getting paid is an anomaly. So hedging is like learning these additional skills, and being at the ready that I may need to pivot into these things if the time ever came. So those are the things that I think about, just because I’m a self-reflective person, and I like to pay attention to what’s going on.

I guess what I meant paying attention to it closely is not like “Man, let me check my watch. Let me check my dashboard this very moment”, but more like just paying attention to it. I think there’s a lot of people who almost live in bliss. Ignorance is bliss. They realize things cost more, they realize things are not the way they were two years ago, they realize money is less free, meaning not only is it worth less, but it also costs more to get it. Interests, right? And these are the levers that the Fed is using, specifically here to the US, and I think it’s probably similar in other markets across the world in how it works… Is that money is less free, you can’t get it as easily, you can’t borrow money as easily, and things cost more. I think that there’s a lot of people out there who are not paying attention to that directly. They’re paying attention to it indirectly by saying “I’ve got less amount in my wallet, I’m not making or I’m making more, or the same, or whatever, but somehow I have less.” They’re paying attention to it in the symptom, not the actual problem. I think a lot of people are like that. And so you mentioned fear, like what do you fear. Specifically, what do you fear then? Go into it more.

I fear that I don’t understand it. For example, everything you just talked about is true with computing. The machines are getting faster. I mean, big time. But the software is getting slower. You still have spinning wheel, even when you’ve got 32, 64 gigs of RAM in your computer. How’s this possible? How is any of this stuff slow at this point, given how much advancements we’ve gotten on the side? But most people don’t care; they just say things like “I’ve got too many tabs open. I don’t know why the software bloat is increasing. I don’t know why everything I use wants to send my data to some random location.” People don’t think about these things and why they’re the way they are. Like, when we say it’s free, what is the cost of it being free? Most people don’t understand privacy, and encryption, until something bad happens.

So for me, while I was in tech - like, I can’t just stand there. I’ve gotta understand how these things work. So luckily for us, we could dive into the source code, we can read the white papers, we can sniff the network traffic to see what’s going on. But when it comes to like society and inflation, and all of these things, I don’t know what in top is for that. I don’t know what the source code is for that. It feels like proprietary software. So then you go into conspiracy theories. When you don’t have facts, you start making up facts. And so for me, I’m asking myself, “Why does it work this way?” So either A, no one’s in control, and we’re just dealing with this stuff like bad production architecture. Things just go off, alarm bells ring, and people try to put out the outage, and we just keep fighting this fire forever. Or there’s a design. If there is a design, what is the system designed to do? And the only thing I can think of when I get to like that conspiracy level, like “What is it designed to do?”, I always ask myself “How will you keep people working? How would you do it?” Think about it… Back in the day, we probably had like kings and queens manifest destiny. “I don’t work. All you work, and you make sure that I don’t work, and all this stuff is mine.” And eventually, you look at that system and you’re like “Yeah, I don’t know about that one. Why are you not working, and you own all the things? It just doesn’t make sense.” And you look around, “Like, we outnumber you… So what does the throne even mean?”

[00:41:58.06] So how would you devise a better system? “I need all of y’all to work. But I don’t want to work.” How would you do it in the most non-violent way possible? So to me, the most non-violent way possible would be “Hey, we’ve got this money printer over here… Now, here’s the deal. Everybody needs to work for money. Yup, you’ve gotta wake up, and you’ve gotta go, and here’s what the salary ranges are. And if you work for 65 years, you can stop.” Alright, fair. I like that deal. So we’re all going to work. That’s exactly right. And there’s ways where you can get more by investing, there’s lotteries, there’s gambling, there’s many ways to take some shortcuts, and it almost feels like Hunger Games. So everyone’s motivated. I’m gonna go to work, do a good job, invest, and then I can get out early. So we’re all on the hamster wheel, and you’re looking to make sure that everyone is on their hamster wheel.

That’s right. And as long as you’re running, I’m not complaining. But if I look across the room, and there’s a person over there handing out the hamster wheels, but that’s it… Like, “Hey, man, why are you not on the hamster wheel?” He’s like “I am the banker. I am the stockbroker. I trade off of your middleman activity.” So you’re making money off of the fact that I’m working? He’s like “Yeah. And it’s totally fair, because I am working.” And so when I think about it, what happens – I asked the question one time to someone, “What happens if everyone was debt-free?” And that person told me society would collapse. I was like “Why would it collapse?” Like, wouldn’t it be good if people were debt-free and had more disposable income to buy the things that they need? He’s like “Kelsey…” And that’s when I started having this opinion that things are not priced at what people can afford. Things are priced at what people can borrow. I’d rather sell you a car for $100,000, than sell you a car that you can pay cash for 50k. I’d rather just make another 50,000 and you’ve just got to go get a loan to buy it, so we just keep the prices high. And if you have trouble getting a loan, then you can buy here, pay here. And I’ll just charge you 17%.

So if you do this long enough, you have the perfect recipe to make sure that everyone works for ever. Like, why would you stop? You can’t stop working. And if you stop working - “Man, something about inflation, man… We don’t know what happened, but all the houses are now up 40% than last year. So yeah, you’re about to retire, bro, but you can’t afford it anymore. So back to work you go.”

So to me, I keep thinking about “Why would you want a system like that?” But I don’t think we’ve figured out a better way of having people do a bunch of work, and a subset of people not doing any work. People still like that model, and I think what we’ve done is said “Hey, what have you had a chance to not work, and everyone else had to work?” And that’s what we call retirement. This is why I’m very respectful of – the only reason why I get to not work is because everyone else has to work, and so my dollars still have meaning. So I am conflicted. In many ways I’m a hypocrite, that I’m benefiting from the exact same system that I’m trying to wonder why it exists in its current form?

Well, what’s the alternative? For you to move to the mountains and not have any sort of interaction with the system, go off the grid, stop paying taxes? I mean, opting out of the system is to everybody but the most extreme just –


…infeasible. Impractical. It’s not something that you’re willing to do. There are people who are willing to completely do that, and they go out into the mountains, and they live, usually in communes, or maybe sometimes on their own… And they just opt out of everything. Otherwise, you are in the game. You didn’t design the game, I didn’t design it… Adam, you didn’t design it, right? Here we are, born into the game, we learn the rules of the game… And then what option do we have? I mean, you’ve got to kind of play the game, because everybody else is playing it… So it’s a – I don’t know if it’s a catch 22, but it’s an unsolvable problem? I don’t know.

[00:46:01.04] I think you’re exactly right. So what I do is – and when I understood the game, I said “You know what - I don’t care about buying some of this stuff at all.” The diamonds, the Mercedes… I don’t care. But man, look at the other stuff. It’s gotten cheaper, too. In totality, a lot of the stuff – like, if you have the premium version, you can go first class seat, or you can go coach. And the coach seat is actually pretty nice these days. You still get to go to the same place, you just don’t get to sit up front. But I get to still go from Pacific Northwest, to Japan, nonstop. Maybe not first class, but I can still go nonstop. So there is progress.

So the idea of being a minimalist, I don’t necessarily buy the cheapest thing. I try to buy the most valuable thing. And I have to help myself redefine what value is. So now I’m just debt-free. And being debt-free in a world where everyone else is paying 7% interest rates is very powerful. And so there is ways to benefit within this system, so I’m not saying throw the whole thing away… You do have to understand it, and there are ways to navigate it in a way that has a net positive for the people who really understand.

So yes, I don’t get tricked into paying high interest rates for things. I don’t get tricked into buying cheap things, where I’m gonna have to buy 50 of them. And so I do think that, so – but I’m also at a point, like, how do you educate other people that want to navigate this system in that way that can maybe cause a little less stress? I mean, there are literally people who are depressed, again, because they can’t buy a private jet. They’re literally depressed. It’s like “Oh, man… What are people gonna think of me flying–” What do they say, flying commercial?

Right. “When’s the last time you flew commercial?” “Ah, it’s been so long.” [laughs]

That reminds me of American Psycho. Have you guys seen American Psycho?

This is a movie starring… Who’s the guy that played Batman most recently?

Christian Bale.

Yeah, Christian Bale. And he’s a psychopath, but he’s on Wall Street, and he’s obsessed with the most material of things… And he’s very successful. He’s made it. But deep down inside his heart, he hasn’t made it. And there’s one scene in particular where some colleague of his presents his new business card. And Christian Bale’s character is just envious [unintelligible 00:48:11.29] of the beauty and the particular font, the typesetting, and the material… And they’re all admiring this guy’s new business card. And he had just gotten his own new business cards, and they were amazing as well, but not as good as that guy’s. It’s like being depressed because you have to fly commercial. I mean, he’s there with guys comparing their business cards, and he cannot find any sort of solace in his life. He ends up going out and murdering a bunch of people… So there’s your storyline. I mean, he’s American Psycho. He’s privately – he does murders and executions. And he actually confesses it at some point. But the person across the desk from him thinks he says “mergers and acquisitions.” So like “What are you into?” He’s like “Murders and executions.” And she hears “Mergers and –” I can’t say it…

Mergers and acquisitions. I gotcha. [laughs]

Anyways, he’s trying to confess; he can’t. It’s an interesting movie.

Oh, yeah.

But there is that thing in us where we want more and more, and a lot of the people who want to make more money off you, they want to sell you that $100,000 car, versus the one you can actually afford, they go about setting up things so that you can go ahead and make that bad decision. And you can go ahead and –

But you know what - the tech game is so similar though, because when we think about like bloat, and “Oh, we should be using this programming language, because it’s better, it’s faster”, and sometimes that stuff isn’t necessary. So being like a responsible engineer, it’s really understand “What do we actually need? Let’s do the most valuable thing. Let’s understand how things work, and not get into these traps of complexity.” These things all have maintenance costs that are super-high.

And so this is what I mean just by paying attention. So for me, the things that I applied in the software world, I would like to apply in just like normal society, because it would be nice that people look at the things that they already have, and try to find a way to be happy with those things. I’m not saying complacent. But if you have a washing machine, maybe you don’t remember what it’s like to go to the laundromat, or maybe you’ve never been to a laundromat and had to wait and haul your clothes a couple of miles away from your house. But if you get a washing machine after going through that, you’re extremely happy about a washing machine…

…if you don’t have to do that anymore. So man, how do you maybe get people to see that again, so they can be just a tiny bit happier with their current situation as they strive for a bit more?

Yeah. Well, it’s tough, because we talked about opting out… A lot of our cultural institutions are all about glorifying the excess. So the private jet, the expensive car, the diamond rings… The Kubernetes… No, I don’t know how we pulled that back across the tech. Maybe it is Kubernetes. Where it’s like maybe you don’t need that. “Well, I’ve gotta have it, because it’s serious engineers, they deploy on Kubernetes.” And it’s like “Do they?” Well, that’s what the culture is telling me right now, and I’ve gotta keep up with the Joneses. So that does require - I think you said it - education. How do you get more people to understand the game, and the rules of the game, and then also the things that are attracting them away from sound decision-making, because there’s so many shiny things that we just chase after, and then find ourselves in debt in many different ways.

Well, I think this is why community plays such a big role in the tech game in general, is because the stories we tell, the talks we give, the research we put out, when we share the numbers, when we write the blog posts, when we do the podcasts… This is the stuff we’re supposed to be talking about, why we use these things, why they exist, when to use them, when not to use them… I think that’s the part of the tech game that we talk a lot about the software, the code, the IDEs, the editors, the copilots… But honestly, it’s that secondary layer, this human layer, where we talk about these things, and they become tools of the trade, and the guidance just comes from the community behind them. So I think that’s one thing we probably all take for granted. This is why I think people do, like Adam said earlier, why are the stories so powerful? Why do they work so well? Because that’s the missing manual. Most of this stuff doesn’t get shipped with the manual anymore. But these conversations we’re having - that’s the missing manual. And this is why people tune in, so they can get all this stuff that isn’t written down.

Yeah… As long as I’ve been podcasting, it’s kind of crazy, because I recently had this - not so much epiphany, but it became more clear to me just how powerful this particular medium is… Because these are real, for the most part, in this case here definitely not censored, but uncensorable conversations, authentic conversations. At length, it’s not – I suppose when we clip it it’s different, but in its long form, there is no agenda. Like, even before the show, Jerod is like “Hey, what are we talking to Kelsey about?”, I’m like “I don’t know, it’s Kelsey. We’ll figure out something, I’m sure. It’ll probably land somewhere.” And we haven’t even talked about what I told him we’d talk to you about. So that’s okay.

But the point, I suppose, is that we sort of come to these conversations, and we have this authentic platform that we speak to literally a global audience of developers, on a weekly basis, for nearly 15 years. We’ve had some ebbs and flows in terms of our frequency and consistency, but for the most part, this show, the Changelog, has been here almost institutionally for at least a decade strong, or more, even though we’re 15 years old; we’ve been strong for so long. And I think people come to this for the authentic conversations from a particular lens, a developer’s lens. And developers aren’t just simply software developers; we think about systems, like you’re talking about. You are one of the lucky ones that were able to have an amazing career, you did well for yourself, you’re amazing at storytelling, you leverage all those skill sets to be able to eject out and say “You know what? I’m done. I’m retiring. I’ve got a different motive now.” And now you’re examining not just software - and you’re not even writing code on your own; you’re deciding not to - now you’re examining the system we’re all playing a role in. And that to me - you’re in a lucky position, but not everybody gets to do that. But people listen to these shows because we have authentic, deep, real, unscripted conversations that for the most part can’t really be censored. No one’s behind the scenes here censoring this podcast… Aside from the obvious curse word; we try to remove those four –

[00:54:13.21] We self-censor. We bleep.

Right. There’s some censoring, but not in the fact that I want to change what Kelsey said to use it against him. That’s not what we’re doing here. And I think for the large part, 99% of podcasts are not having that motive.

So I want to talk on this one really quickly, because I think people forget - nuance takes time. If you only have a three-minute conversation with someone, you’re probably gonna get their best answer, their curated thing that they were ready for. But if you talk about that subject long enough, then I think you get the full depth of what they’ve ever thought about a particular subject, and then you get the nuance. And nuance ain’t pretty. The nuanced ain’t polished, the nuance ain’t perfect, and the nuance usually isn’t complete… But the censoring component - when I worked in big tech, it was a very weird thing that… I don’t think people understand, the amount of media training, the amount of people that are paying attention to every word you say on social media, every podcast, and then have something to say about it is insane. I don’t think people understand it.

And when I got to go – I did media training, but for some reason, they let Kelsey be Kelsey. A lot of stuff, people were just reading second hands, like “Oh, it would have been nice if you’d have told me that you were going to be on the Changelog. It would have been nice if you’d told me you were going to tweet that.” I’m like “I am not here to only say the things you want me to say. And also, the things you want me to say ain’t even that great, to be honest.” People aren’t buying it. Enterprise adoption, something digital transformation, something DevOps. Nobody wants to hear that no more…


Like, at all. These are real people, doing real work, they already have the way that they think about it, and what they want to do is have a real person also think about it, too. Not regurgitate. So you’re right about this censoring thing; like when people come on these shows, and you’ve got your “Can I see the questions first?” And then they get media to go through and approve all the answers… And it’s very robotic. If you’re listening to this and you’ve done that, nobody likes that. Nobody wants to hear that.

We don’t let them do it, honestly… They ask us to give those questions, and we’re like –

We dodge it.

“It’s a conversation.” We might give them topically, but we’re definitely not giving them questions. Like, that’s just not how things work.

If you’re listening to this, you don’t want the questions. You want to be honest. Look, I get it, when there’s data that you want to give out factual information, just say “I don’t know the exact numbers, but here’s where we’re going with this. Here’s my observation.” Nobody wants you to be repeating this stuff they have five people on a Google doc approve before you got on the show. That’s not necessarily what people want to hear all the time.

Well, we had that – I’ve never been inside an organization that does that media training stuff… So I’m pretty ignorant of it all. We obviously can detect it as people who talk to people for a living, like when they’re on message, when they’re on brand, and when they’re just being themselves… And we were at Microsoft Build a couple of weeks ago, and did a lot of conversations with C level guys… And all were interesting, all were good, from my perspective. And obviously, our listeners can judge individually what they think. But there was one of the – I won’t name names, because maybe that’d be a fun game for the listeners, “Which one am I talking about here…?” There was one of them that was like just clearly just being himself. And it was like – I don’t know if he’s just done the Kelsey thing, like “I’m just gonna be myself and let the chips fall where they may…” And the other ones were more like I could tell that was a canned line, I know he was ready for this particular thing… Like that kind of deal, where they were trained. They still were charismatic and interesting people, but they were just on brand. And you can just hear – I just actually listened back to it, because we just released it this week… And I was out mowing, and I’m like “I’m gonna listen back”, and you can just hear which of those conversations was just three guys talking, and which one was a guy who was clearly media trained, and then two people trying to talk to him. And… A big difference.

I’m gonna tell you guys, an executive at a company like that… It is one of the hardest things to unlearn that you’ve drunk too much KoolAid. Because some people don’t even know, because their identities merge. If you’ve been at a place for 15 years, sometimes the identities merge.

Oh, yeah.

You are your job, and you don’t know the difference anymore. You’re the same. So when someone asks you a question - I don’t speak two languages, but some people who speak two languages says this happens to them, where you want to answer and you’re trying to find “Oh, are we English or Spanish right now?” And you’ve got to choose. And sometimes you may say it in English, but you’re using the Spanish way of thinking about the phrasing. Some people put together words in different ways based on the language and how it constructs its vocabulary, its nouns, its norms… And when it comes to tech, some people do that as well. It’s like, “What are your thoughts on Cloud?” “Well, it’s allowing people to transform.” You’re like “What the hell is that? Who says that? No one says that in the real world.” In the real world you’re like “Hey, you know what? Computing is hard. There’s no way every company in the world’s going to invest billions of dollars in underwater sea cables, regions all over the world. It’s just not going to happen. So someone does that, and we sell it to people. That’s what we do. Here’s the things you can do with it. Here’s where it sucks, and here’s where it’s great.” That’s too nuanced though, because you said “There’s parts that suck.” “Oh, no, no, no. Cloud is just great.”


So I’ve gotta imagine, as you begin to examine the system, you begin to come up with theories. And some of those theories, because you’re examining the system and you’re questioning, because you’ve now got free time, you’ve now got reduced fear, so you’ve got a superpower that not a lot of us have, which is financial freedom to an extent - there’s probably some things that’s gonna happen to ruin some ideas and plans you have. So you’re not a billionaire, I’m assuming. Maybe a millionaire, right? Okay, he’s shaking his head no to billionaire. It doesn’t matter how much you’ve got, but the point is that you’ve got this superpower that not many people have, which is lack of fear on financials, for now. There’s still some fear there, but you’ve got enough of a safety net where you’re like “Phew, I can breathe. So now let me look at the system. Okay, I’m gonna look at my inflation dashboard, I’m gonna look at the way software works, I’m gonna compare that to other things that I know of.” And then you begin to develop theories. Some of those theories might cross into the conspiracy level. How are you doing on that? Because sometimes when you get into the position you’re in, you can become cynical, you start to, to some degree, overanalyze - rightfully so - and begin to kind of get into that conspiracy realm.

So one thing I have to realize is that I think a lot of times when people get money, they believe that they’re smarter than other people that don’t have money. So they think that their ideas should rise at the top. They’re obviously right about something, because their bank account reflects just how right they are. That’s the mistake. To me, I know that I’m lucky, and a lot of things could have went in multiple directions, and it doesn’t end up with this particular number. And so one thing I’ve challenged myself for the last maybe 20 years, “Who am I, and why do I believe what I believe?” That’s it. Sometimes I believe things because I didn’t have time to research them, so I had to just take them at face value, they were taught to me, I didn’t have time to challenge them, so I took them.

So these days, when I look at it, I try to humble myself, and be like “Kelsey, do not fall into the lifestyle inflation. Do not over-index on showing people what you have. It is okay if people don’t think you’re in the top X percentage of anything.” Remind myself that “Yes, you could buy it, but you don’t need to. What’s caused you to want to do that kind of thing?” And that helps me avoid the conspiracy. For example, if you say “I need more money”, you will be really mad that you pay taxes, because people are taking away the very thing you want. I don’t mind paying for the bridges, the highways, the medical stuff…

[01:02:05.01] Do I like the waste? Absolutely not. I’ve seen waste in enterprise, so I’m not surprised that there’s waste in government. So I don’t over-index in that, because I also know that people are hard to be very good 24 hours a day forever. It’s not happening, folks. So I’m a pragmatist when it comes to that stuff.

But the conspiracy theories - whenever one pops into my mind, I say “Kelsey, it’s time to do some research here. Before you start running your mouth, before you go on Twitter just saying random stuff…” For example, when I wanted to understand inflation, I had to go read The Monster on Jekyll Island, how the Federal Reserve was formed… Buy some, Treasuries actually buy Treasuries from Treasury Direct, look at the interest rates, look at the curve… Why do people start feeling a certain way when it goes up, start feeling a certain way when it goes down? Who buys them, who doesn’t? How big is the Treasury market versus the stock market? Treasury market’s dramatically bigger. Why is that?

So these are the types of things that I go into to just try to resolve the conspiracy components with actual facts. And then I just talk to people. “Hey, explain to me how this works, please, because I don’t know.” And then people give me insight, give me something I don’t know, they close the knowledge gap. And then I’ll test. So if I’m really afraid of something, I’ll test it. When the whole crypto movement was going, I was so afraid, because I saw [unintelligible 01:03:25.25] It doesn’t matter if things are logically correct or not. It don’t matter. If the world decides that we should all jump off our roofs, with no helmets, then just people start doing it. It’s like “Oh, what are we doing?”

So when I saw the crypto craze, it felt like people were really serious about adopting dog coins in replace of normal currency, with at least some transparency, with some levers, some minor checks and balances in place. I was really nervous about that, so you saw me ask a lot of questions in public…

I did see that. I was paying attention.

…like “Yo, what the hell are we doing? Am I missing something? Is this the future, or y’all just trying to get rich?” So that fear had me accelerate the understanding I needed. And then people came for me. “You don’t know. You’ve got to do this. You’ve got to do that.” But the dope thing about it - I didn’t change my mind on what it was. I understood what it was, and I was no longer afraid. Y’all want to get rich. And I understand the mania, because for some of y’all it worked. It’s just like when people line up to buy lotto tickets. Okay, that’s just normal human nature. I can live with that. I’m no longer afraid. And then I move on. So that’s just my method of dealing with the conspiracies. Because if you get into the conspiracies, then Tupac’s still alive.

Which we all wish was the case, you know…? Confirmation bias. You want it to be true.

He might still be alive. We just don’t know. [laughter] Lots of new music. He just dropped an album last week. I mean, what are you talking about?

He’s a ghost writer for Drake.

There you go.

Well then, I guess to be point blank, have you conjured or thought of or come up with any conspiracy theories or believed in any as part of this investigation? And if not, you kind of gave it away a little bit there, but how do you maintain a sane mind? Because it’s hard to not be tainted by masses thinking one way, and it’s not.

What I realized is that I don’t need the conspiracy theories. I don’t need answers for everything. I’m just not that important in the grand scheme of the universe. I don’t need them. I noticed a lot of people use conspiracy theories as crutches to make themselves feel comfortable by having any answer. And I’m actually okay without having answers to some things. The thing that I just wanted to make sure of is that I constantly ask the question “Who am I?” and work towards that. And a lot of this stuff that we’ve made up as humans, the concept of video games, the concept of wealth, the concept of money - you can pick any of the -isms. Those are things that people made up probably to feel comfortable or try to understand the world, in place of having an actual answer. So for me, I don’t need the conspiracy theories. And when I don’t need them, I don’t entertain them very long. I just don’t know.

[01:06:06.21] So then I ask myself, “What things do I actually want to know the answer to?” And then I just put my energy into those. So that’s my thing, I don’t need them. Because when you need them, you will pursue them. And what you will do then is since you need an answer so bad, the conspiracy theories become a temporary placeholder. You’re just like “Alright, that’s my answer for that.” And then you go around and you Alex-Jones all of a sudden.

Now we’re censored. Now we’re censored. Thank you. You said Alex Jones, now we’re censored. Gosh…

If you say it three times, he shows up.

We’re not gonna censor you, they’re not gonna censor us. They’re gonna kick us off.

Yeah, so I don’t know. I’m okay with that. I don’t need the conspiracy theories. I just want to make sure that I know how to think, I know how to slow down… Honestly, I just wish more people would slow down. We see the same thing in tech hype. People get behind this stuff because they don’t have time to form an intelligent answer, and so we just ride with the last conference talk, or we ride with the last set of viral tweets.

So I’m just about taking time, man. If you can find the patience… I was watching one of these – I told you I’m getting into this tradesman stuff, and I’ve found that there are like these electrical installer competitions. They literally give people these scenarios, with these half walls, and they’ve got to do this thing in an hour, and they compete against each other. And the dude that’s winning - he’s moving slow. He measures stuff on the wall, he writes stuff down… He don’t touch stuff more than once. Everybody else is picking it up, moving the ladder, picking it up, moving the ladder… Not him. He’s like “Alright, this is how it’s supposed to go.” He looks at the blueprints, makes his marks, does his cuts, puts stuff in place, looks at the blueprints one more time, hits the clock. And he’s done 30% faster than everybody else. He’s methodical. Everybody else is moving quick and going nowhere. That is the thing that I’m trying to hold on to. Be methodical, and there’s a team of people doing their own thing in their own lane. I don’t need to swim in all the lanes.

Slow down to go faster. I’ve been saying it for years, over and over again. Slow down to go faster.

But you’ve gotta be good. So that’s the thing.

Of course.

It only works because he’s actually good. He actually has skill. He’s probably put in the work. He’s probably done all the right things, so he can go methodically. The people that don’t quite have the skills dialed in, they have to compensate for the lack of skill by doing stuff seven times, because they don’t really know how to do it once.

Yeah, because you’ve got to fix what you just did wrong. You do it wrong, you do it again, or better, right?

Do it right, do it light. Do it wrong, do it long.

I like that.

Break: [01:08:36.15]

I was gonna ask you, have you begun to consider raising chickens yet?

“Nah…” [laughs]

First of all, I’m vegetarian. So that’s kind of the reason why.

But I do know that I depend on society. So I think, Jerod, you talked about people that want to go off the grid, and… Like, they’re fooling themselves. We’re on the same spinning rock; you rely on lots of things to happen by people you don’t know. You can go on your little island, and then someone shoots a missile at your place. Now what? You’re still connected. You can’t dodge it. And so I’m not interested in necessarily dodging, I’m interested in contributing in a way that’s helpful. So the people that do raise chickens, are they in a good mood? Because if they’re in a good mood, maybe they don’t start injecting the chickens with poison to make them grow fast so they can get more money. We don’t want that. So I think people that are more comfortable, that are feeling good, tend to do the right thing.

That’s all I’m trying to do. That’s how I want to participate in this thing.

Well, my line of thinking was to get to an understanding of who you were. And I think you asked this question to yourself even, like “Who am I? Why do I think and believe what I believe?” And the reason I was asking about chickens is there’s this theory that once you begin to raise chickens, there’s a certain sort of sphere you live in that then begins to unravel different things you question life around you. Because you raise chickens, you start to think about it differently, like not injecting with antibiotics, or growth hormones.

[unintelligible 01:11:55.02] My daughter is 17. She’s graduating high school. Finished two years of college. She did the early programs, going to UDub in the fall… And when you have a kid, you realize the game ain’t just about you. It’s not about just you being safe. It’s not just about you having everything taken care of. Now you’re making decisions because there’s a person that didn’t ask to be here. You brought this person into this world, and you are responsible for them until they can be responsible for themselves. And yeah, it does change the capitalist completely. You start looking about “What world will they have to live in? I brought them in here, and what world would they have to live in? And then how do I contribute to that?”

So the reason why you save a little extra is not so you can buy something, it’s so that you may need to be able to invest in them, so they can do something. My career has stopped. My professional W-2 career has ended. Hers is about to start. I’m excited about that, being able to be that coach, be that person to do the code review as she started taking some of her CS courses or informatics courses when she gets to college. I’m thinking about what that internship will be. I’m thinking about “Man… Hopefully there’s enough nice people that when she’s a rookie, and she joins the team, that they don’t make her feel like she wants to quit tech. Hopefully, the whole industry has evolved to the point where she can land on a team that knows how to mentor and get her to go from a junior engineer to a senior engineer.” That’s the calculus that I’m currently doing, and then the generation that comes after that.

So that’s been my thing for a little while, Adam. This is why when people DM me on Twitter, I’m like “Just call me, man.” I don’t know who you are. You don’t have to pull rank. You don’t have to tell me what your background is. I don’t need a link to your LinkedIn. You seem like a person that believes that I can help you. Do you know what a privilege that is, that someone believes that one of the most important things in their life, that I can be of help? Come on, man… Look at that responsibility. Because a lot of times you give people advice, and I’ve seen it boomerang back, where you meet someone - I’m walking around San Francisco and a kid runs out and is like “Hey, Mr. Hightower.” I’m like “Damn, I’m not that old. I’m only 43.” He’s like “Mr. Hightower, you answered the phone for me years ago. And you told me to do boom, boom, boom. And I did boom, boom, and now I’m in San Francisco, I’m in tech, I got a job, and I was just eating. I saw you walk by and I had to run out and say thank you.”

Like, that to me is worth doing this stuff, because I can afford to. I can afford for it not to be about me. I can afford for it to be – you know, the hardest thing to do I think is a person striving to get what they want to get is being happy for someone else. Everyone thinks it’s easy. They’re lying. It’s not easy. If you work at a job next to your fellow colleague and you’ve both got the same title, Linux System Administrator level two, they’re going to get their performance view, you go in, they walk out, Linux System Administrator three, but you’re not. How hard is that for you to do the math and be like “Why did they get it and I didn’t?” It’s hard. But when you have a child, something in the parental programming, when your child wins, you just smile for them.

Oh my gosh, yes.

We winning. When they lose, you’re sad for their loss. You find a way to be happy or empathetic about someone else’s achievements. And man, I wish more people can do that with their peers, as well.

Speak to the other side of advising… Because I’ve done some advising, and I’ve given some good advice, then I’ve given some advice where I was like Hmm… Maybe the outcome wasn’t what we hoped.” Or I was wrong. And you are advising in big life decisions of businesses. These are the big decisions. And you have the great story of the boom, boom, boom, and then success… But surely there’s been times where you’ve been wrong, or off, or didn’t have enough information… That’s a big responsibility, too. How do you look at that?

I don’t know if people tell me enough when I’m wrong…

They blame themselves?

Well, I think they might just say “We’re not going to listen to that one” and then go in a different direction.

Right. No return customer on that one, I guess.

Yeah, maybe you don’t get a return. But also, when you’re an advisor, you know that you’re one of many opinions. You’re not THE opinion, you’re one of many.

And I think that what people want from you is number one, they want the spectrum to be expanded. I know what my people are telling me, I know what my customers are telling me. “Let’s check in on Kelsey, to see if he can add something to this for us to consider.”

So let’s say it’s bad advice. So then you’re on the other end of the spectrum, of things we shouldn’t do. It’s bad advice. And as long as they’ve got something on the other end, now they’ve got something to compare and contrast to, and they can go Why. So for example, I won’t mention the company name, but they’re going to do an acquisition. I did the review and said “I wouldn’t buy this.” But they bought them anyway. So was it bad advice? We’ll find out in a couple of years, whether that thing adds to the revenue pool or not, or the people are still there or not after a couple of years… But I think it was one of these things like “If that’s the worst that Kelsey can come up with, we’re comfortable with that. We just needed to hear, so we can understand the full complete picture of the risk profile.”

So I think as an advisor, your goal isn’t to necessarily be right or wrong, because that’s tricky. Because it also depends on their ability to execute. So everyone kind of knows that my job is to say “Here’s what I believe, and here’s why.” And the math is clear. And if it’s wrong, then “Look, great. Don’t do that.” But at least we have the spectrum. That’s what people are paying for. They’re paying to expand the risk spectrum, so they can make a good decision.

Right. Now apply that to your daughter. High risk. N of 1… Some fear in there…

Um… No. No, no, no. For her, the safety net is big. I don’t have that kind of safety net, at all. So her safety net is humongous. And the biggest fear I have for her is that I learned a lot by walking the tightrope with no safety net. When if you don’t save, you ain’t paying the phone bill. You know if you get fired, there’s going to be problems. She won’t have that per se, but I still want her to develop character in some other way. There has to be a way to stay diligent, to take that safety net, that foundation and go even further with it.

[01:18:08.19] I don’t want her to have that reset, because I’m already afraid of the reset for myself. I’m not going to have her start over. What’s the point of me doing all this work, getting to this point only for her to start over. So I do want her to be able to continue and do something for it… But she said something dope, that resolved a lot of my fears. I said “Hey, we’re saving all this money, we’re doing all these things. I want to make sure I leave something to you.” She said “Dad, I hope you live for a long time.” She said “Let’s just do the math. Let’s just say you die at like 90 or 100. That means I’m like 75-80. Like, hopefully I’ve done some stuff on my own too to have a good life, and I’m not going to be sitting around waiting for you to leave me something, and then it goes.” I’m like “Yeah, you’re right about that.” That’s not the game plan, for her to sit idle until I’m out. The game plan is for her to do her own thing, and maybe she doesn’t need it.

So then you just hit the gym, right? Try to make that 90-100 happen.

Hit the gym, the mental, relax… Appreciate the time you have… I think – you know, yeah, I want to live as long as possible… But boy, do I want to live good every day that you get? Like, literally, I’m waking up, and I’m like “Man, the sun up? I’m still breathing? There’s a lot of former billionaires that ain’t here.” You ain’t trying to trade places with them right now. And so for me, that’s just kind of where I’m at.

I’m on the way to this KubeCon thing, the 10-year celebration. It’s tomorrow in Mountain View, and they asked me to MC it, help put together the schedule and the story arc… And it’s crazy, because it’s the 10-year mark, and it’s this moment of reflection. This thing has been around for 10 years. Everyone thought it was gonna be like another Open Stack. People thought it was gonna die due to complexity… But this thing is still here [unintelligible 01:19:54.18] a lot of the people that are working on it, and I’m witnessing the new generation come in and replace all the original folks, and then keeping this thing moving. So that’s kind of dope to see this thing kind of come full circle, and then keep moving, whether we’re deeply involved or not.

Yeah, it’s wild, man. It’s good that you’re wise enough to ask yourself, rather than pull down from all the mental threats, I suppose, that are out there in the world, the societal threats, ways of thinking so to speak, that you’ve asked yourself “Who am I, and why do I believe what I believe?” Now, I’ve gotta imagine - and maybe this isn’t true, but my question really is how did you become so wise to ask yourself that question? Because I think that’s identity. Most of us act irrationally, make bad choices because we don’t know who we are. And because we don’t know who we are, we don’t know what we should do. And then you ask yourself one more question on top of that, which is “Why do I believe what do I believe?” which is “How does what I truly believe is true true, and why do I believe it’s true? What is my evidence for that truth?” So how did you become so wise, and who’s helped you to become that way of thinking, that kind of brain framework, thinking framework, mindset?

Honestly, the credit probably goes to everyone in your life. Your mom, your parents, your friends, your colleagues, all that stuff. I was 22, 23 when I finally realized - and it was from observing just where things were going at that time; so I’m 23 in 2000, 2003 maybe… And so I’m looking at the game, and I remember I bought this Suburban. Car nut, right? No kids, no family, nothing. Just me, 5’9”, and I have a seven-seater car. I ain’t taking no kids to soccer or practice… I don’t even own a home, so we ain’t going to Home Depot. “Why do you have this car?” And I had the car so you could see it, and be like “Damn, he drives a Suburban.” That was why I had the car, literally. Just being honest with myself.

[01:22:02.08] And then you look around and you’re buying all these clothes… Again, I don’t really even care about these clothes, but boy, do other people do. And I said “You know what? I made a decision. I’m living by myself. I’m managing the comedian.” I had this consultancy business, entrepreneur… I’m like “We’re doing this stuff, we’re ripping and running all the time.” But when you’re managing comedians, you see the high and the low. You’re seeing very famous comedians spend $40,000 at a club on alcohol and making money fly in the air. And then you watch MTV, or some behind the music thing, and they’ve got no money later. How do you make all that money, and then be broke? And not just broke. You owe the IRS a couple of million, so you negative. How does this happen? So you watch it in real time. And I’m like “Oh, this is how this happens.” And I was like “You know what? I’m getting rid of the truck.” And one of my buddies was like “What are you doing? What are you going to do?” I was like “I’ll just rent a car when I need one.” He’s like “Kelsey, how does this even work?” I was like “I think I got it figured out. First step is –” And I don’t know all the things. So there was one step of “I’m living in the South.” And you eat steak, potatoes, macaroni and cheese, all the sides, you eat the same diet all the time. There’s no big deviation when you grow up where you grow up. You eat what everyone else eats. So I was like “Ah, I’m going vegetarian.” “So what are you gonna eat?” “I don’t know, man. I’ve never eaten Indian food. Let me try some of that. I’ve never messed with Thai food like that. Let me try that. Afghani food. Let me try that. Ethiopian food. Let me try that.” So I was forced to expand, because I couldn’t go to the normal spots anymore, because they ain’t have nothing that fit that.

So now you’ve got this forcing function… Who am I, and why am I that way? So now I’m vegetarian, because I chose to be. And now I’m eating all this other stuff. And now I’m paying attention to what they sell. “Hey, do you have something that isn’t these things?” “We don’t.” So now I’ve gotta go somewhere new.

Now look, for me, that was the number one way to expand my horizon, for someone that’s in their early 20s. Then I looked at the debt and said “Why do I owe all these people money? It makes no sense. I’m out.” And I went to the dealership, and I was like “Hey, I’m going to turn in my cars.” Like, “You can’t do that.” I’m like “Yes, you can. Voluntary repossession. You have to take these keys back. Worst case you will sell the car and I will owe the difference. And I’m ready to pay that difference when it comes. So here’s the keys. Do what you’re going to do to the credit score. I am off the debt treadmill forever. I’m out.” And my friend’s like – and like “Hey, I need a ride home, because I ain’t got no car now.” [laughter]

And so I get a ride home, and I didn’t live too far from an enterprise car rental. And that’s when they used to come pick you up. So I went there, and I still have my consultancy, my computer shop thing… And so I would get the car, and do service calls with it. Right? How hard is this? And I was like “You know what? I need to be charging trip charges when I go out and do these IT installs.” So you build it all into the model. And then guess what, if you’re savvy, you rent the car on Friday. They closed on Sunday. They have these discounts over the weekend. So when you’re try to go out and do dates and all this stuff, you get the car on Friday, you turn it back on Monday, and you don’t lie. This is a rental car. I am debt-free. This is part of the whole debt-free thing. Anyone that can’t get down with that, I can’t afford to be with them anyway… The good lifestyle is not what I’m trying to be about. So then people see who you are.

So now I’m debt-free. So that’s like “Hey, everything gotta be debt-free. We’re making decisions different over here.” But then when you do get money, what do you do? Do you change up? No, you stay the same. Nah, no, no, no, we stay the same.

I used to date my wife in high school, but we reconnected years later. And I remember two things. Blood test, credit report. I was like “Oh, you’ve got debt. No, no, no, no… We can’t get married with no debt. Here’s how it’s gonna work. I make calls, pay things off, but you’ve got to pay me back. Because I’m not the boss of you. You’ve got to know how I feel, and you’ve got to earn it back with a little help. Now you’re debt-free.”

[01:26:07.17] Right before we got married – we set the date for marriage right when the debt was going to be paid back. Now she’s her own person. She has what I have - independence. She knows what it’s like to be debt-free, and she knows what it’s like to be in control. And I proposed with a cubic zirconia. “Why am I paying ten grand for a diamond? It makes no sense. I can pay $1 for cubic ciconia. We pocket the rest.” We got married in Bahamas. Not because it’s fancy, because AirTran - I don’t know if y’all remember AirTran, the airline…

$79 from Atlanta to the Bahamas, each way. We got married in linen. If you stay five nights at the hotel, you get married on the beach for free. One of the cheapest weddings ever. But the people who came was like “Wow, you guys are doing a destination wedding? How rich are you?” “Not that rich. I’m like $1,300 into this thing.”

So to me it’s one of these things that when I saw how much power came with that, and how I felt with that, I felt like I was in control. So then everything became an examination. “What am I buying? Do I really need all this stuff?” So then I discovered words like minimalism. And it’s like “Yeah, that’s what I’m doing.” So it gives me a word to communicate to the outside world what I’m doing. I don’t need all of that stuff, because I don’t want to wash it all, I don’t want to clean it all, I don’t want to move it all every time I move… I’d rather stay this way.

Zoom forward 20 years, my life has been like that. “Why do I work here? What’s my job role? How does this work? Do I even need that?” And then it just becomes a formula for how you live. It’s your principles. I read Ray Dalio’s Principles book… And most people just don’t have any principles. That’s the problem. I don’t care if you’re a Pittsburgh Steelers fan, or you’re a Las Vegas Raiders fan. That doesn’t matter to me. Why are you a fan? Do you really like football, or you just like this team? The people that like football can watch any game and enjoy it. The people that only like their team, if their team don’t win, they can’t watch it anymore. They just turn the game off. “We’re down by too many points. Turn the game off. I don’t watch it anymore. My team’s not in playoffs, I don’t watch football anymore until my team is winning.” Like, that’s the difference.

That is enough for me, man. That’s a good mic drop right there. I like that. That’s a lot of good thinking right there that I think that I’ll go back and listen, and probably listen to – we chapter our podcast, as you may know, Kelsey… So we’ll put this as a chapter and we’ll just let people put it on repeat… Because that was a lot of good advice there, especially at a young age. I mean, you’re a contrarian, probably, to some degree. You don’t have “Go with the sheep” thinking. If everybody’s doing this, you’re sort of like “Why is everyone doing it like that?” Like the car thing, like “Why do I have this Suburban with seven seats when I’m one person? Why do I have this car now when I’m this?” You are a contrarian style thinker.

I will say I’m not that insightful. I wasn’t that insightful when I made those decisions. It’s that I slept in my car before. And so when you’re sleeping in your car, and you stop to think “Why am I sleeping in my car?” And look, I didn’t do anything. I wasn’t on drugs, I wasn’t a bad person. I didn’t get in trouble with the law. I just made a decision to try to do small business versus having an apartment, and the trade-off was you’ve gotta sleep in your car sometimes.

And so you’re sleeping in a car, and it’s like “What do I have to do not to sleep in this car?” That that was like the thought process. It wasn’t – I don’t know if I blamed anybody else. I didn’t blame society, I didn’t blame even my own decision that kind of put me there… Because that was a choice to do that. I was like “What do you have to do not to do that? But you’ve got to think about it.” That’s it, that’s the only calculus here, is like just “Who am I, and why am I that way? Why do I believe what I believe?” And if you constantly ask that question, you start challenging stuff like “Hey, I only believed that because I read it. Maybe I should read a second source, or ask someone “Am I thinking about this correctly?” Humble. It’s really more about being humble, and giving yourself room to change, and not feeling bad about that.

Kelsey, it’s always a pleasure talking to you. We didn’t even talk about the topic I shared with Jerod at all, and I’m cool with that. 100% cool with that.

I want to hear the topic you shared with Jerod.

No. Gosh, no.


It’s left field.

It’s embarrassing compared to what we just talked about.

Let’s let’s do it for Plus Plus, how about that? We’ll close the show, we’ll do it for Plus Plus.

We’ll do it for Plus Plus. Hey, if you’re not a Plus Plus subscriber, what’s wrong with you? It is better. It’s better! Support us, hear more of Kelsey, all that good stuff… And Kelsey, thank you so much, man. I really appreciate you.

Awesome. I’ll catch y’all.


Our transcripts are open source on GitHub. Improvements are welcome. 💚

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