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Chapter 1: What is Kelsey Hightower's unconventional path into tech?
Kelsey Hightower is known as one of the most influential voices in the Kubernetes community. But you wouldn't guess from how his career started. At 19, he dropped out of college to be a DSL modem installer, became a self-taught developer, and still went on to become a distinguished engineer at Google. At age 43, he then retired at the very top of the industry.
Today, we cover Kelsey's unconventional path into tech and how he kept creating new opportunities for himself, often unknowingly. The inside story of the container wars, Puppet, Docker, Terraform, CoreOS, and how Kubernetes eventually won. Going from a Google IC to executive level and how he rejected a Microsoft offer from Satya Nadella himself and still doubled his compensation.
His grounded and pragmatic advice for software engineers, worried about being commoditized by AI, and so much more. If you're an engineer and thinking about your long-term career trajectory, whether that's getting into a staff plus level, going independent, or even quietly planning to leave the industry, this episode is for you.
This episode is longer than a normal episode, frankly, because I was so glued to my chair, mostly listening to Kelsey's stories and thinking. This episode was presented by Antisysis. verify your system's correctness without human review or traditional integration tests, and avoid bugs or outages.
Before we start, I'd like to mention our presenting sponsor, Antisysys, and maybe offer a little history lesson. Over the last two decades, software development has gone through a mindset shift from an imperative approach to a declarative one. Infrastructure is a perfect example. Think about how tools like Puppet and Ansible allow declaring how individual servers should be configured.
Then came Terraform, the ability to declare the desired end state of your whole infrastructure, servers, networks, databases, and their relationships. And then with Kubernetes, we stopped scripting container life cycles. Instead, we write manifest to say things like, I want three replicas of this application exposed behind the surface with this much CPU and memory.
Once we didn't have to specify every little detail of our infrastructure anymore, deploying software became much faster. But then the bottleneck became how quickly we could test and verify the code to be deployed. Testing remained imperative. We had to write tests for every little detail. And now with LLMs, we're on the verge of a declarative shift in the way code is written as well.
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Chapter 2: What were the key moments in Kelsey's early career?
Just tell the model what you want and let it figure out the details. And it's going to make the verification bottleneck a million times worse. Antithesis is a declarative testing tool that can keep up with your AI coding agents. You state the properties you want your software to have and Antithesis figures out how to check them for you.
Verify your code as fast as agents can write it and ship with ground and confidence. Head to antithesis.com slash pragmatic. Kelsey, welcome to the podcast. It's so nice to see you in person.
Yeah, I'm actually happy to be here, mainly because I kind of look at your stuff over the years. So it's an honor to be here in Amsterdam as well.
How did you make your first dollar at a job?
Oh, my first dollar at a job, McDonald's, right? That counts. So in high school, you get the job that's closest to you. So it was in walking distance of my house. As soon as I turned legal age, 14, get a work permit.
And I went there and it was one of those jobs where, you know, you go, you fill out the application the same day, you typically get your information or you're going to get hired the same day. When can you start? I'm like, right now. They go get a shirt for you on the back. And what size do you wear? Men's large.
And the one thing I liked about that job is you're dealing with real people better in a hurry. I guess one bad part about the job, you know, a lot of people don't respect people who have that job. So they kind of look at you as just like this intermediary thing between them and what they want.
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Chapter 3: How did Kelsey build a reputation through open source?
But there's so many things that go into a restaurant like that. It's very efficient. You know, people have expectations. And I learned how to run the whole store. So by the time I turned 15, I was a assistant manager. So... nights and weekends, you know, other managers would leave, they would give this 15 year old the keys.
And I knew how to do everything there, including close out the store, right? So you have to count all the money, you have to fax this huge spreadsheet to corporate every night, and then my mom would pick me up. And so it was really good learning how to really be responsible even for adults at that age. So that's how I got my first dollar. How did you get into tech?
How did you get into programming? In high school, since I moved from California to Atlantis, you're going from one side of the country to another side of the country. And I missed maybe three to six months of school. And in order to graduate on time, I had to take some extra classes.
And so as someone who played sports, ran track, played football, played basketball, and it's like, you know, there's this computer programming, you know, computer club, technology student association. There was a class component and then there was after school component.
Chapter 4: What insights does Kelsey share about the rise of Kubernetes?
And I was like, I don't know, man, this computer stuff, that's for the, you know, I'm trying to be a cool kid. But the one thing I did, I really enjoyed it, right? So I had a liking to AutoCAD. I even competed at the state level in AutoCAD. So we drove down and you compete, they give you a task and you sit in front of the computer.
It was my first year doing it, but I really liked the idea of like taking a specification, designing it. And I probably would have gotten first place if I would have got the product to work because you also have to print it out. so that the judges can review your work. So I got second place, even though I didn't put it out.
This is a 3D modeling.
Yeah, AutoCAD, you know, just AutoCAD. Yeah, so part of the curriculum was, you know, you build bridges. We did this thing with chapter team where, you know, you have a coat of arms and you're kind of doing like a debate. So you kind of learn all of these things related to business. But CAD was one of the things I liked most. Also in that class, one of the classmates taught me TI BASIC.
Is that a version of BASIC? Well, so TI basis, so you know the graphing calculator. It's like a TI-86. Oh, yeah. You can program it.
Oh.
Right? So in class, they're like, hey, you know, it's not just a graphing calculator. You can actually program it. And I was like, what's that? And it's like, look, we can, you know, everyone at that time, you would create the snake game, right? So it's basically get a magazine, copy and paste the code, and then you run it. And now you're playing snake based on the code you wrote.
And so you would toy around with this concept. So that was probably the first introduction to programming was literally programming my TI-86 calculator. And after high school, did you go to college or you considered college, right? I considered college because in Georgia at the time, and still today, there's a thing we call the HOPE program.
So if you have a B average or above, you can go to any public school for free. And public schools in Georgia include Georgia Tech, Georgia State. These are pretty good universities. Yeah, they're really good. And so I decided to go to one that was near me. The first two weeks, I was like, this is too slow. This is not the pace that I want to move at.
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Chapter 5: What insights does Kelsey share about his experience at NASA?
And so I felt at the time that I had come full circle and I was starting to think about the exit. Part of that journey, I remember spending time with Jet Propulsion Labs, JPL, part of NASA. And I remember being there and I was so excited because the movie The Martian had just wrapped up filming there.
And they gave me a tour of the facility, like the Mars rover, the new one before they launched it to Mars. They were QA and it was just going in a circle around the track. And I'm like, I had a little laser on there so I can split rocks.
Chapter 6: How did Kelsey define his role in DevRel at Google?
And they were showing me how they improved the wheels over time. I went to another lab and there were a bunch of scientists working in there. And it looked like a fish tank. And I described it that way.
It's like, yeah, we determined that if you want to replicate parts of Mars' surface, and I might be getting this wrong, that the rocks that you find in a fish tank, we can replicate some of this stuff. And maybe it's slightly different than that.
Chapter 7: What are Kelsey's thoughts on slowing down in his career?
So I'm watching these people work, and they show me how spacecraft has evolved over the last 20 or 30 years. I'm like, wow, you all seem to have an actual purpose. For the first time, I've seen people using technology not to just make more apps, not to add numbers in a database, but to actually have humanity do something. And so they were not all about Kubernetes and Docker and Python and Go.
They were like, we're just trying to get a person to Mars and back again. I remember part of the interview process, their interview questions are, if you had to deflect a meteor, how would you do it? But it has to hit one state. So now you're in the leadership position, what would you do?
Chapter 8: How does Kelsey view the impact of AI on software engineering?
And you're just explaining the answer. You're like, you know, I would kind of bring a bunch of experts and then, you know, you got to think about the ability to evacuate people and you have to explain yourself. And the core part of my answer was, you would have to explain yourself almost 24 hour live stream.
Here's the trajectory, giving everyone the countdown, explain every decision you're making. I chose transparency. I chose truth. I chose like, look, we have to deflect it. There's no way to make it zero. So we've chosen this state and this is the evacuation plan. And we estimate that this number of people won't make it. We're just being honest with you. No need for conspiracy theories. It's live.
And I was like, wow, what an interview. A 20 year career at that point, never had an interview that made me feel that way. And so I actually was going to go to NASA after CoreOS. I even signed the employment agreement. I was going to move to Pasadena, California and work at NASA on the Mars mission and lead up the infrastructure and the infrastructure teams.
And of course, Google called and was like, hey, come to Google. And at that point, I was like, for what? You have hundreds of thousands of employees. I admire Google. I've been there before, but not in that capacity. I was going to go to the headquarters. Yeah, not to the data center. Not to the data center, but to the headquarters.
And I've always admired people like Brian Grant, Eric Toon, Don Chin, all of these wonderful people that I got to work with through the Kubernetes community. In many ways, I felt like I was already working on the team because by that time, I had commit access to Kubernetes. So I kind of felt like all the things I wanted to achieve in that regard was there.
And so I was like, why would I come work there? I was just going to be a cog in the wheel. I'm going to go there. I'm just going to disappear. They're going to just make me work on Google stuff all day long. What's the value in that? I've seen the peak of this. And they were like, we won't do that. I was given the opportunity to do DevRel, and it's the first time I ever did it.
But DevRel represented freedom. No tickets, no right code measured against SWE benchmarks. I was like, I don't want that. I want to be able to make impact. And so the team was smart. They were like, look, we've got this area called DevRel, and we'll let you define what you do.
So you got to write your job description pretty much.
Yeah, but as an entrepreneur, I know how this goes. How does it go? If you come in and you really do DevRel stuff, in my mind, you're going to get fired. Because if you limit yourself to the external perception of DevRel, you go to conferences and you become more of an evangelist, you do tutorials and guides. For me, those are activities. I'm a person of impact.
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