Jason Warner - CTO at GitHub

(Joel Beasley at 00:00:00) Hello, my friends. Today we are talking to Jason, the CTO at GitHub, and we discuss his transition from VP of Technology to CTO, how to coach your team to deal with failure, and why he almost quit working in technology two different times. All of this right here, right now on the Modern CTO Podcast. Here we go. This is the Modern CTO Podcast.

(Joel Beasley at 00:00:34) There he is. Joel, how's it going? Dude, man of the hour. How are you?

(Jason Warner at 00:00:39) Pretty good, you know, 2020 good.

(Joel Beasley at 00:00:42) 2020 good? Yeah. You're in a new room now?

(Jason Warner at 00:00:44) Yeah. It looks like you've got a new background as well.

(Joel Beasley at 00:00:47) I do. We built a little studio out, and now we look professional, you know?

(Jason Warner at 00:00:53) Well, professional, and then you grew this massive beard.

(Joel Beasley at 00:00:56) I know, right? A COVID beard. You've got some shadow going on, though. Are you going to grow it out?

(Jason Warner at 00:01:03) I have a rule, which is I shave every Sunday. So it's Wednesday, or I guess Tuesday today. So this is my Tuesday shadow from Sunday.

(Joel Beasley at 00:01:11) So is it that you just like doing difficult things, or...

(Jason Warner at 00:01:15) I'm lazy when it comes to shaving during this time. Like, what's the point, right? I'm married, got three kids. I know what my life's about at this point. And I've got to actually go cut my hair. That's the other thing I've got to do. But I do that every sixth week now or so. I've learned to cut my own hair, so, you know, I'm due for that this week.

(Joel Beasley at 00:01:35) You're cutting your own hair? Like, you watched a YouTube video? How did you do that?

(Jason Warner at 00:01:38) I have been actually cutting my own hair for a little while, but not to the degree in-depth that I need to do here. You know, you do the tune-up haircut. Now I've got to actually cut it. So I've got the wireless clipper. I do the various guards up and down, and then I have to have the wife come back and clean up the back of the neck here. And in my situation, my head doesn't actually stop anywhere on my body, so I actually just have to have her create some sort of forest line cut on the back of my neck between the back there.

(Joel Beasley at 00:02:12) Yeah, there you go. That's what you do. Just punch a good line in, and then you can work around that line.

(Jason Warner at 00:02:17) That's right.

(Joel Beasley at 00:02:19) Dude, I love this. It's always great talking with you, man. Last time we were hanging out, you were the SVP of Technology, but now you're a CTO. Was that because you came on the podcast?

(Jason Warner at 00:02:31) It was. It was a correlation is causation type of situation. So anyone who's thinking about coming on the podcast, get on the podcast.

(Joel Beasley at 00:02:40) Well, how has the role changed for you, though?

(Jason Warner at 00:02:45) In my situation, in this context, massively. Typically, I would say that the role I was in before was GitHub CTO, but what it was before and what it is now is very different. So let me explain. Before, when we talked, I was the SVP of Technology, which in GitHub's history also meant CTO. But in that case, I ran product engineering, security, support. I had data and infra as well. And I ran all those functions, and product design rolled up to me via product at the time. Since, we've hired people for all those functions. And this is all post-acquisition. Pre-acquisition, I actually had BD and corp dev for a short period of time as well. But post-acquisition, we've hired a head of product, we've hired a new engineering person, new head of data, new head of infra. And I have since gone on to CTO. In this context here, it means that I run a small office, the Office of the CTO. It's very in line with what Microsoft does in those functions. Kevin Scott is the Microsoft CTO. He has an Office of the CTO. Mark Russinovich is the Azure CTO. He has a small Office of the CTO as well. So it's a little bit different than what people consider to be a traditional CTO role, but I quite like it. And it kind of gives me room to play. What I do is I focus on Horizon 3 stuff, so all exploratory, all, you know, you won't see it manifesting in GitHub for probably years at this point, but it's all fun stuff.

(Joel Beasley at 00:04:18) Oh, that's cool. Because I was going to ask you about the new—I just got the emails and all the notifications that the new GitHub CLI is coming out.

(Jason Warner at 00:04:27) Yeah.

(Joel Beasley at 00:04:28) And I was curious, not necessarily about the details of the functionality of it or whatnot, but when something like that happens, how much of that is on your radar? How involved are you in that?

(Jason Warner at 00:04:40) Well, so interestingly, all of those things are still manifesting from old roadmap that we put together while I was in my other role. So I know about a lot of that stuff intimately, though there is a point in time when I start to diverge in my knowledge about what's happening on the roadmap from a detail perspective. So because of the overlap in time, I still know a lot of those things and have been pretty close to them. CLI is a good example of something, though, that we had on roadmap, but the details of it are different than when I was there in that other role, so it has started to diverge a little bit as well.

(Joel Beasley at 00:05:17) So then, now, today, you're just focused on Horizon 3 stuff?

(Jason Warner at 00:05:22) Horizon 3 things. So the way we classify these is Horizon 1 is near-term roadmap. Horizon 2 is a little bit more speculative, but you should probably be getting 80% of those things right with a little bit of customer development. But Horizon 3 is probably three-plus years out—things that we think should exist, but we need to go figure out how to make happen.

(Joel Beasley at 00:05:46) That's awesome. So when people ask you what you work on, is it hush-hush, like DARPA-type stuff? Or do you get to talk about it?

(Jason Warner at 00:05:54) I like to talk about it, but I always caveat it with we're going to fail more than we're going to succeed because that's the nature of taking on very experimental things. And so don't expect the things I talk about are actually going to show up. But when they do, they're going to really change GitHub. So a good example of this from recent history that I would consider to be this type of stuff is the original GitHub Actions. That was a very speculative, long-term strategic thing that we incubated inside GitHub for some period of time. We're looking at things like that—things that are tangential or kind of adjacent to what GitHub does today but in new and interesting ways, and we will find ways to bring that into the current product.

(Joel Beasley at 00:06:37) Nice. Yeah. I was—I'm always looking out for new tools and new features, things that are pretty cool. I'm at this company called Rookout, and they actually sent me a little sticker, right?

(Jason Warner at 00:06:48) Rookout Labs, right? They do the...

(Joel Beasley at 00:06:50) Oh, so you know them? Yeah. Oh, so then, no, all right, I've got to find a different company now.

(Jason Warner at 00:06:57) Well, I think I'm pretty close to most of the things that are happening in the software space, particularly when it comes to dev tools.

(Joel Beasley at 00:07:04) Yeah, because there's some that just come out and I was like, they had a really smart team, and then I met them and I met their CTO and I got to talk to Liron—and I think I'm pronouncing that right. But he was just a really smart guy. And whenever I find small teams that are doing something really interesting and really smart, I always like to help push them forward and get them out there into the world. But then I saw—my producer right now just pushed a note that said your CEO is actually an investor in that company.

(Jason Warner at 00:07:37) Yeah. So Nat—between Nat and I, I think we know pretty much everything that's happening in the software space these days, and we're likely one—either one of us is likely an investor in one of them, too.

(Joel Beasley at 00:07:48) Yeah. So when you saw Rookout, you were like, this is an interesting product?

(Jason Warner at 00:07:52) Yes. So the way I categorize what's happening in software is it's in the ideation space, the code space, the build-test-hack space, or the production space. And unfettered territory is in production at the moment, is the way I categorize it. So I'm on the lookout for anything that's interesting in that space—people are doing things new, different, a little bit out there, because that's where I think a lot of the innovation is going to happen in the next five years.

(Joel Beasley at 00:08:21) Nice. Have you—did you get to see the—it just came out on Netflix—The Social Dilemma?

(Jason Warner at 00:08:26) I have heard about it. And obviously, if you're on Twitter, you're hearing about it a lot, but I've not seen it.

(Joel Beasley at 00:08:31) Yeah. So I actually watched it, and one of the questions that I have coming out of it, just that I'm asking around for, is this concept of algorithms and echo chambers, right? We're all kind of familiar with that as a topic of conversation. I was just curious, have you had any deep thinking sessions on this? Are there any interesting solutions out there? Do you—I mean, I don't have anything.

(Jason Warner at 00:08:58) So, I mean, I think, like most, I have opinions on what is happening in the social space, social media, and then algorithms in general. And, you know, you can take a couple of different views on it. I wouldn't say that I have any depth of thought specific to social media, nor expertise. But what I do have is I have a little bit of fear around it because you see what's happening in 2020 with social media, and you worry about it. But at the same time, I'm a—I think the term is you're a long-term optimist but short-term pessimist, and that's how I view things. And software in general has changed the world entirely in a very short period of time. But at the same time, you have that short-term pessimist view about what will happen with it. Long-term, obviously, I think software and technology in general is going to continue to change people's lives for the good. But it's hard to reconcile or square that circle with what you feel short-term on those things.

(Joel Beasley at 00:09:53) Yeah. For me, I was—I'm just trying—I'm getting my feet wet into these conversations because I'm learning a little bit, trying to discuss a little bit, trying to wrap my mind around it because, you know, you and I have both been alive since before these things really existed. And now, you know, I've got—we both, you have kids. We talked about that last time, right?

(Jason Warner at 00:10:15) Yeah.

(Joel Beasley at 00:10:15) So you've got your kids. I've got—I think they're older than mine. Mine are only three. But, you know, they're going to be—these are going to be real things happening and decisions we're going to have to make about when they enter into these types of technologies.

(Jason Warner at 00:10:29) Well, the thing I think about quite a bit is more at the societal level on these things. And we all know that people's opinions and information have been shaped for generations and decades and centuries based on who they hang around. So, you know, there's that concept that the five closest people to you, or information sources, are going to drastically shape your view of the world. And this is borne out in history. And I think about the power that the social media—the media landscape in general has had for decades, but social media in particular today. There's a reason why the Murdochs wanted to go buy a newspaper and a media outlet. It's because they understand that you can shape opinion based on how you present arguments. Well, social media is doing that these days. You know, I just recently tried to get off Twitter, and you quickly find yourself in a situation where, where do I get my news these days? How do you do that? RSS is still around, but no one's using it the same way. You know, and most people get their news from Facebook or Twitter or some form of social media.

(Joel Beasley at 00:11:36) I actually went and, out of frustration—because I'd go on Twitter, I'd go on these things, and then you see the things you care about, but then you also see rabbit holes they try to pull you down. And so out of frustration for longer-form content or just more intellectual views of stuff rather than just the screen view, I started researching, and I actually found a couple of newsletters that I subscribe to. And so now my key sources are these two newsletters I get every morning which just kind of summarize tech and business in this very direct way.

(Jason Warner at 00:12:15) I definitely think there's going to be what we might call cottage industry things popping up around the ability to get information from others in a filtered way, which also is a dangerous approach, too, because then you have somebody else filtering the information for you as well. But at the same time, people aren't going to want to sift through that stuff anymore.

(Joel Beasley at 00:12:33) So how are you staying fit during the lockdowns?

(Jason Warner at 00:12:37) Oh, my goodness, that is tough. I have worked—I work more now, and I've been remote—if you recall, I've been remote for 10 years. I've never lived in San Francisco, and I've been doing the remote thing for quite some time. So if anyone should be familiar with being used to this, it's me. And yet, I have worked more during the pandemic and COVID than I ever have, and I'm in worse shape. And it is tough. It's tough because there's this—I feel like there's this cognitive overhead. I'm a little bit more tired than I typically feel. You know, what's that about? I have been trying to do a lot more simple things—walking, eating less, a little bit more things that I can do on a consistent, everyday basis instead of—obviously, going to a gym has been difficult for quite some time. And if you live in a state where that might be slightly more open, how do you feel about going? Well, I don't feel that comfortable going, so I'm not. So things I do at home. So I do walk more, take more calls on the headset. Been doing a lot of kettlebell stuff, trying to do things I can do in 10, 15 minutes because schedules have gotten pretty bad.

(Joel Beasley at 00:13:52) Yeah. It's the wild west down here in Florida. Gyms are fully open and packed. But they do the temperature checks, though. Like, so here's the deal. At my gym, you have to walk in with a mask on, but then once you check in, you have to do a temperature check. So you walk in, you do a temperature check, and then if you're all good, you get to go in, and then you don't have to wear a mask while you're working out.

(Jason Warner at 00:14:16) That's interesting. I'm not sure I would feel comfortable being inside in a place that does not have the mask mandate at the moment. To each their own, I guess, in that one.

(Joel Beasley at 00:14:28) Yeah, I'm on the side of freedom. And, I mean, I was actually hearing this interesting argument the other day, and it had nothing to do with masks. It was just talking about the purpose of America. Like, we came here. It was an experiment in self-governing people, right? Individual ownership and these concepts and these disciplines and these things that I personally am a fan of. And so when everyone seems to be so split up—and I definitely don't go political stuff on this podcast—but when things seem to be split right up, I just try to find some really good principles that everybody can enjoy and then just hit those hard, because when things are split, what you need is unity, right? And so it's like, all right, well, rather than figure out how we're all so different, let's find some things that we all agree on, because we could use some of that right now.

(Jason Warner at 00:15:18) We could use some unity in 2020. That is for sure.

(Joel Beasley at 00:15:21) Yeah. And maybe we all direct our anger at the algorithms. No, I'm just kidding.

(Joel Beasley at 00:15:29) No. We'll stick with freedom and things that we like as people. So what are you watching anything interesting these days? Any good media?

(Jason Warner at 00:15:40) You know, I can't actually say that I've started to watch more things in lockdown. Obviously, just like early in the early days of this, I think Mandalorian had just come out or something like that. I think my son and I watched Mandalorian for the first time. Of course, I started hearing about Tiger King. Is that what it was called, right?

(Joel Beasley at 00:15:59) It was Tiger something. Yeah.

(Jason Warner at 00:16:01) Yeah. In the earliest. So I did watch an episode or two of that, and I was like, I don't know how I feel about humanity continuing to watch this one. So there was, I think Bill and Ted's 3 just came out?

(Jason Warner at 00:16:14) Yeah. And so I'm waiting to see. I do want to see, what is it, Tenet? But I'm not going to do a theater at the moment. So I want to see if they can stream it. I will watch anything that they stream from a theater perspective at home.

(Jason Warner at 00:16:27) There was a TV show that just came out on Amazon Prime, I want to say. The Boys? Yeah, the superhero one. So I did watch a couple episodes of that as they're coming out.

(Jason Warner at 00:16:42) And they had a season one already, so I watched season one, and then I'm watching the episodes as they come out just now. But not too much that I'm really watching these days.

(Joel Beasley at 00:16:52) There's a pretty—

(Jason Warner at 00:16:53) Oh, and then basketball came back. So I've been watching basketball.

(Joel Beasley at 00:16:56) Are there crowds? How do they deal with that?

(Jason Warner at 00:16:59) Basketball? Also, they're doing a bubble for basketball. And they're down in Orlando, actually.

(Joel Beasley at 00:17:05) Okay.

(Jason Warner at 00:17:06) And what they do is that they chose a set of teams that were close to making the playoffs to start. And they said basically, you're essentially self-quarantined inside of this bubble and can't leave. If you leave, you've got to quarantine inside your room when you come back for X amount of days depending on if you got tested every day or not. And until the playoffs are over, you don't get to leave if you're still competing for the championship.

(Jason Warner at 00:17:29) And right now, they're in the finals, the conference finals. So the West is playing, and the East are playing, and there's four teams left. And they're continuing to go.

(Joel Beasley at 00:17:38) Nice, nice. But they don't have an audience. It's just they're playing games.

(Jason Warner at 00:17:43) No, it's all streamed. Yeah, they do have a, I'm not sure technically how they do it. I'm assuming it's a massive amount of TVs that are all kind of linked together. But they're doing a thing where audience members can broadcast themselves into the arena, the place where they're playing, and they're digitally broadcast on there.

(Joel Beasley at 00:18:02) That's actually that's a way better solution than cutouts. You know, everybody else they were talking about.

(Jason Warner at 00:18:07) It's a lot more fun. You do have a lot more interesting things that happen with that. And the cutouts, they're kind of creepy. They're kind of creepy. Let's just admit that.

(Joel Beasley at 00:18:17) Yes. But I saw I think I saw the first person was Tony Robbins, because I follow him online, and he does these massive events in person, like, four times a year or something. And he did this, he built the stage and this giant wall of Zoom videos, and I was just blown away by it. And then since then, I've seen a number of other people build these studios with these walls of video of all the people on them. Does that make sense at the NBA? Was it the NBA?

(Jason Warner at 00:18:48) The NBA did it. Yeah. And, you know, football, I think they're doing the cutouts, what they're doing. No. Is it baseball that's doing the cutouts? Somebody's doing some cutouts somewhere. And I remember seeing pictures of them. It's like, that's sure, I get it, but also a little creepy.

(Joel Beasley at 00:19:02) Yeah. Jake just said that baseball is doing cutouts.

(Jason Warner at 00:19:05) Baseball is doing cutouts. Okay. I think football is doing nobody in the stands or anything like that, but football is pumping in crowd noise, interestingly. And so, like, you know, if you're the home team, they're pumping in the cheers and the claps, if you've done something positive in the boos, if you're doing something negative, I guess, or whatever. And I saw something. I went down a little bit of a rabbit hole about it because I do like sports. But one of the Philadelphia Eagle home games, apparently, one of their players did something kind of boneheaded, and they pumped in a whole bunch of boos to kind of get that Philadelphia crowd vibe going. And I thought, that is brutal. Nobody's in the stands, and somebody's making a choice here to pump in boos because of some boneheaded play that you did. It's like, all right.

(Joel Beasley at 00:19:51) See, what we need though is on the video connections, we need clap icons, you know, and boo icons. And then you should generate the noise based off of what the people are actually doing.

(Jason Warner at 00:20:03) It is kind of strange actually being remote in this environment when you're doing things like your podcasts are one thing, but I've done a bunch of conference remote conferences now, and you don't have any feedback whatsoever in terms of how you're doing. And then whenever you're on stage, while there's lights and there's things that are happening, you always place people in the audience. And you're looking for head nods, you're looking for the thumbs up, you're kind of looking for signal. So you've got your own plants inside the audience, but you're also looking at others too, and you're just trying to see how that's resonating with folks. There is zero feedback anymore when you're in an environment like this. And it is kind of strange when you're giving a presentation.

(Joel Beasley at 00:20:45) It is very. And when I first got into public speaking, somebody gave me that advice. They said, when you're up on stage and you're doing your beginning, start scanning the people you can see, because you can really only see the first row or two. Scan the people you can see and find the person who's tracking with you. There'll be a person or two that are tracking with you and then look at them and talk to them and watch how they're going. And when I did that, I was like, whoa. This concept of interacting with the crowd is its own part of life. It's its own unique experience that I personally enjoy.

(Jason Warner at 00:21:19) It's very different though in 2020 to do that. So you've got to find your own rhythm. That's the way I kind of describe it. Because you can feed off energy. Like, Tony Robbins always talked about this, actually, way back when. When you're in the arena, the energy that the audience or the fans, they give you. There is no energy. You've got to create your energy. You've got to bring it. So you've got to bring that with you and you've got to keep it going.

(Joel Beasley at 00:21:43) Yeah. One of my kids, they play with this guy named Luke, and Luke's one of Tony's main guys, and he's also a speaker. So Tony travels with a bunch of speakers that he works with. And I was over at their house, and they have the trampolines that they use, old Tony and all the speakers use. They jump on the trampoline backstage before they go on. So I got to jump up and down on the trampoline. I was like, okay, I'm not bringing one of these with me to my tech talks, but I see the value of getting you pumped up. So I just put in music and read through some notes and get myself, you get Eye of the Tiger going, get pumped up. You know?

(Jason Warner at 00:22:25) It's the, I mean, I don't think this ever goes away for folks, but there is those butterflies that you get before you go on stage, particularly for a larger audience. And I always talk about the perfect dose of caffeine. When you go on stage, if you have too much, you're going to talk too fast. If you don't have enough, you're going to have the jitters. Which one, that perfect dose. You know? You want to have just the right coffee hit at the right amount of time ahead of going on stage. I can see the same thing with getting amped up.

(Joel Beasley at 00:22:52) Yeah. Right? You can't do too many songs in a row. You get too pumped up. If you do Eye of the Tiger three times, you're going to be through the roof. Eye of the Tiger one time, maybe one and a half.

(Jason Warner at 00:23:05) The entire Rocky IV soundtrack would be fine.

(Joel Beasley at 00:23:08) There we go. There we go. Okay. So I'm curious. We were doing research and we found some fitness books written by Jason. Is that you, buddy?

(Jason Warner at 00:23:20) So that is me. That is me.

(Joel Beasley at 00:23:21) I love them. I love them. It seems like it's something from the past that you're just like, but I loved it. Like, when I was reading through them, we were so excited. Our producer was like, I'm going to do a push-up for every minute of the episode. I was like, we're going to make this thing go through the evening. Hope you brought your sleeping bag.

(Jason Warner at 00:23:39) Yeah. So my face got a little redder on this, just so you know, if you're watching instead of listening. But yeah. No. Yeah. So a friend of mine did those probably about ten years ago we started doing them at this point. Yeah. It's been about ten years. I think I'm co-author on, what, five of them? About five. And he did somewhere between eight and thirteen or something like that. He went through a real spell of doing them. But he and I just kind of got into a phase where we're really getting into fitness. And he connected with a publisher, Ulysses, and we just had a series of books that they wanted us to produce for various niche markets. And some of them were what we call challenge books.

(Jason Warner at 00:24:25) So they started with Steve Speirs who did the, I think it was Seven Weeks to 300 Push-Ups is where it really started. And then, you know, pull-ups and sit-ups and things of that nature and adding muscle or losing weight or things like that. Those are called challenge books. And the other ones were just general fitness books for various niche markets that they were trying to go after. And we'd never written books before, so we wanted to see what it was like and got into doing it.

(Joel Beasley at 00:24:48) Dude, that's exciting. I mean, look, I've got some embarrassing stuff from the past. I'll throw out there just so you're not alone. I've intentionally never talked about it on the podcast, but I think this is probably a good time. So I did these motivational audio tracks that—

(Joel Beasley at 00:25:08) Nice. Yeah. So it was called Beast Mode Audio, and I just wrote these motivational speeches. Right? Because I had heard somebody do this on YouTube, and I was like, oh, that's actually that's pretty interesting. And my brother-in-law is a music producer and so he pointed me in the right direction, helped me out with all of it. But I released an album and had it on Spotify and stuff and I'd done this, I don't know, I think ten years ago. Right? And I was just kind of like, okay, that was a fun project just to see what that would be like. And it was out there. And it wasn't on the first, it was on page 20 of Google if you search for me. Right?

(Jason Warner at 00:25:43) You got to deep Google to find those. Right?

(Joel Beasley at 00:25:45) Yeah. You've got to go ex-girlfriend stalker status to find them. Right? So then one day I walk in, I'm working on this project for this government agency thing, and I walk in and they pull up on the conference line and the hold music, they had found one of these tracks and made the hold music one of my tracks. And I was like, oh my god. And they all just cracked up and were laughing. They had planned it ahead of time and I was just like, are you kidding me? Dude, I looked like a tomato. I was so red.

(Jason Warner at 00:26:20) That is, I love that, but that is deadpan type of just make it. Oh, that is amazing.

(Joel Beasley at 00:26:28) That's like walking in a lunchroom at GitHub, and everybody's reading that book.

(Jason Warner at 00:26:32) So GitHub, they found out about it. But by the time we did the books and then my time in GitHub, enough years have passed where, you know, the Google searches are on page 14 or something like that. And there's enough Jason Warners in the world too, where you kind of can get disassociated with time. Even on Google, their algorithms don't match it up. But when I was at Heroku, Heroku had a gym in the basement of the building on Seventh and Townsend in San Francisco. And given that I was remote, I didn't see this very often. So one day, I go down to the gym. Next thing you know, there's books everywhere in the gym. And I just realized, oh, no. They found these things.

(Jason Warner at 00:27:13) And there was one guy, there was this one guy who I became good friends with who said, yeah. We just happened to think that we didn't have enough educational material down here. So it's like, you son of a bitch.

(Joel Beasley at 00:27:27) But think about it though. At least it's not you in eighties attire, skin tight stuff doing some workout jazzercise video.

(Jason Warner at 00:27:38) That is fair.

(Joel Beasley at 00:27:39) Hair going on, you know.

(Jason Warner at 00:27:40) There is a, there is a Jason Warner who we've gotten merged at one point. I think we've been disassociated with each other, now. But there's another Jason Warner who wrote a couple of books, but this Jason Warner is a musician, but happens to be a gay Christian rock musician who wrote a book on same-sex Christian surrogacy with his partner. And, yes, there's a lot of things you've got to jump over to get to that one, but that person and mine came up in the same search settings. But the funny part is I became very good friends with the head of sales at GitHub, who he himself is married to a guy, and they have a surrogate son. And they went down that path, so I happened to send him one of those books. And he's like, wait a second. I was like, no. No. It just so happens that it's my name on the book, but it's not me. And I just thought you'd find it super hilarious. And he's like, I got super confused really quickly, but thanks for clarifying that.

(Joel Beasley at 00:28:42) Oh, I love it. That's a good one. We all have things in our past. I mean, I don't even, I guess, I don't even know why I get that embarrassed about it. Maybe because I tend to see myself as someone who follows through on things and does things for long periods of time. And I just kind of did that as a fun project to experiment with what it would be like. And at one point, I even checked because, like, I put it out there, you know, let it a couple years go by. But I was getting between ten and fifteen thousand plays a month on it on Spotify. So I was like, hey. It didn't, maybe it helped somebody.

(Jason Warner at 00:29:20) There's something strange about having it out there, you know, particularly if you just become more well known for a certain thing, like you've gotten the podcast. And, obviously, my time at Heroku and GitHub, it kind of put me into a sphere of influence that's weird. And then have that out there is like, oh, hang on a sec. How did I thought this through? I might have used a codename or a surname or something like that on those books. But at the same time, you just start to laugh about it at this point.

(Joel Beasley at 00:29:45) Well, it's pretty obscurified. Like, when we were doing our research, we weren't sure. We weren't sure because you can't really tell in your author picture if that's you or not. It's a jacked guy, but you're not looking at the camera. You're doing a push-up or 300 of them.

(Joel Beasley at 00:30:04) But what gave it away? Here's like three simple little words gave it away, and it was "lives with his wife" and so-and-so, something British Columbia. And that same sentence was both in your profile, for your author profile and your profile in your biography. It was written the exact same way. I was like, "That's him."

(Joel Beasley at 00:30:23) There it is.

(Jason Warner at 00:30:24) Yeah, that is definitely me. And then yes, that would've given it away.

(Joel Beasley at 00:30:30) Dude, that's cool. I think you should write—we should write a technology fitness book.

(Jason Warner at 00:30:38) Yeah. Well, maybe at some point we should do the "how to stay in shape while traveling a ton for work," like a travel fitness thing. Because there's a lot of people who could probably benefit from not screwing up your back while traveling, which is something I've experienced in the last couple of years, or, you know, hotel workouts or something like that.

(Joel Beasley at 00:30:58) That is actually—you know what I heard from somebody and then I implemented it was, when I land, I go to the grocery store and I stay in the hotels—because you would, I was so surprised to find this out—there's an entire class of hotels that have kitchens in them, right? But they're pretty much everywhere. You just have to look for them. Like, none of them, when you use your app, you're not gonna get one by default. You have to go specify and filter out and find the right ones. But I just go to the grocery store and get one of those types of hotel rooms and then just keep making my food, you know, as much as I can. It's hard. It's not easy. It takes a lot of discipline.

(Jason Warner at 00:31:42) No, in fact, one of the things that I did—because I do travel a ton, or I used to travel a ton—I actually implemented very strict rules when I traveled. And in many ways, I actually got in better shape with more extensive travel because my rules were so rigid and strict. What I said was, when I travel, I will always work out every day. You know, it's the first thing you do. And for me, when I woke up in the morning, I tried to find a hotel that had a pool, because one of the best ways to stay fit when you're traveling is swimming. And swimming in general is a great, great workout. I would always eat the same thing every day. No deviation. And I wouldn't eat out. If I went out to a restaurant, I would always pick the same—I would always know the menu I'm gonna eat, and I would eat the same thing, set of things. And if I went to a hotel, I tried to put a standing order in. If I stayed at the same hotel, put a standing order in. So if I'm coming there, I'd call down and say, "Hey, it's Jason. I'm in this room. I'd like the usual." And I would never waver from that. So you can always kind of guarantee—you at least, as much as you can possibly control in a situation like that—that you're gonna get, you know, you understand how many calories you're eating, how many grams of protein, carbs, and fat, and all that sort of stuff that you're gonna eat. And you try to stick with it. And then no drinking whatsoever when you're traveling. And that, you know, is odd for some people, but that is the easiest way to let things go awry. I don't drink in general anymore, but when I first implemented it, it was no casual drinking whatsoever.

(Joel Beasley at 00:33:18) Yeah, I haven't been drinking since my twenties, really. Basically, it's when it started to affect me. Like, I would wake up and be like, "Oh, I feel like garbage." And I just don't like to feel like garbage. I like to feel good. But I'm like 200—and I got a notification the other day. I'm like 270 or 280 days into I've tracked every calorie and macro that I've eaten, weighed myself every day, and I've been working out like five times a week. So I put on about—right now I'm about like 11 pounds of muscle for the year since January.

(Jason Warner at 00:33:55) Well, I like the fact that you're—gaining muscle is one of those things that does take an incredible amount of time. And, you know, there's things that you can't do in short periods of time. Gaining muscle is one of those that you can't do in a short period of time, and also gaining strength. You just can't gain a massive amount of strength in a short period of time. You have to be consistent. And it's actually one of those things that makes you appreciate athletes of a certain caliber because you understand that for them to achieve a certain set of things, you have to put in the time. You gotta put in the time consistently over a long stretch of time with a certain intensity. And it's kind of fascinating once you know that you can appreciate some people's achievements more.

(Joel Beasley at 00:34:34) 100%. I started making friends with people at the gym just because I'm there so much. And I was looking at the different size people and asking them how long they've been, you know, consistently working out. And wouldn't you know, the big jacked people have been doing it for like a decade. Like, they've been working out forever.

(Jason Warner at 00:34:51) There's obviously, if you get into like performance-enhancing drug territory, there are certain shortcuts you can take for this. Still does not mean you don't put in the work. Those are just both called flavor enhancers. There are certain thresholds you can get to now that are achievable that would not be physiologically achievable by a normal human being, but you can get to those things. But I think it was someone like The Rock, I believe, said, "Hey, how do you get to look like you?" And he's like, "Simple. You just work out every day for an hour for the next 20 years. That's what you do."

(Joel Beasley at 00:35:22) Yeah. Dude, I love The Rock. I follow his Instagram. He got his gate broke the other day, so he couldn't get to the movie shoot. So he just ripped it off with his hands. And he took like a few—

(Jason Warner at 00:35:36) I like—so I have two of my man crushes, and The Rock is one. The other one's Ryan Reynolds, and I've been incessantly teased about them for like 15 years. But luckily, both of them have entered the general consciousness for people to just appreciate. But I've liked Ryan Reynolds since he was on—there was a "Two Guys and a Girl" and a pizza shop TV show or something like that. But The Rock and him are two of the people that I think I only have Instagram these days to follow those two people.

(Joel Beasley at 00:36:05) Let's talk a little bit about leadership stuff before we wrap up. Is that cool?

(Jason Warner at 00:36:09) Awesome. Love to.

(Joel Beasley at 00:36:10) Boom. Alright. So right out of the gate, I was reading this AMA and—well, this is actually not leadership at all, but I was reading this AMA of you and it said that you almost tried to quit tech twice. Can you elaborate on that?

(Jason Warner at 00:36:25) Sure. So I did. I almost quit tech twice. In both times, I would think that either I'm not cut out for it, either from a personality perspective, or it's just too brutalistic from a leadership perspective. Like, you just end up working for jerks on a regular basis. And to be really frank, it's hard to quit tech because the money is so good. Like, even as a programmer, the lifestyle, the money is phenomenal. And you get to solve interesting problems, but you sometimes do it for jerks. And so I remember, I'm in my late twenties is when I really started to take over engineering teams, and I realized that I could give them something I never had, which was a good leader, a good team, an approachable system, and a way—you know, a job they can get satisfaction out of and they can achieve things, but they don't have to be completely ground down. And I realized that, like, you know, while I was trying to quit twice and I couldn't for financial reasons, I really wanted to make it my life's work that I would show that there was a completely different way to achieve significant outcome and do it in a different way. That's something that maybe others have been able to do, but you don't see the examples in the industry as broadly as you see kind of brutalistic examples.

(Joel Beasley at 00:37:53) And so, like, you stayed in order to be a better leader to these people, give them—

(Jason Warner at 00:37:59) I stayed originally—I stayed first because the money was too good. Second, I—like, so I'm not—I'm just being really transparent. Like, it's either that or go first.

(Joel Beasley at 00:38:08) Best thing you can do, man. Yeah.

(Jason Warner at 00:38:10) And then you start to stay because you realize you can give others something you never achieved. And then you start to realize when you have some success doing it that way, I want to become that example for the broader industry. And, you know, fast forward 15 years, and here I am, the single most important person in GitHub's history, doing it my way in a way that you want to show is possible to do, turning GitHub around and then giving GitHub its massive success. And then you think, "Well, how far could I take this to show that you could do it at a Microsoft scale or a large company scale like that?" And then we can just completely jettison Larry Ellison's examples of the world at some point and say, "Yeah, that's a tactic that you can do, and it's easier to go to Larry Ellison's path. But look at Jason's way of doing it. Yes, it's harder to do, and it's a higher skill move, and you're threading more needles, but it is possible. That's what we want the industry to strive for."

(Joel Beasley at 00:39:05) Yes, yes, and yes. 100%. When I, a few years ago, I bought three books from billionaires because that's one of my goals—I wanna bring a billion dollars worth of value to the world. And I read Elon Musk, Jeff Bezos, and Richard Branson. And what I learned from listening to their stories and watching their leadership styles and everything from that was that I wanted to pick the best parts of each of those individuals. Because, like, Bezos yelled a lot and Musk had some issues too with temperament. Branson was really nice and sweet and just led with like a different culture, but then he wasn't as technical. So I was like, "Alright, I want the technic—" I just picked the best parts and I was like, "Alright, let's try to make that human." But, yeah.

(Jason Warner at 00:39:58) I've started to call this—one of the things that I struggle with in the industry in general is that the tech industry overrewards confidence as opposed to competence. And in the long term, in the time scale approaching infinity, competence will tend to win. But in the short term, you could overreward or over-signal on confidence alone. And so I have tried to show that you can be competent with confidence. And that was the thing I struggled with early on in my career—I was overly competent and lacked confidence. And now obviously I'm at a different point and stage in my career and I have both, and I've gained the confidence. But if I was younger and I had the overconfidence of some people in the industry for what they've achieved early on, I would have had a head start. Now, obviously, I'm in my forties and I'm doing it. But I think what you said is right. Like, don't study anyone and try to adopt anyone. Steve Jobs is amazing for what he is, but he was a terrible example of a leader, but he was a great product thinker and a good company builder. But he himself was not the shining example of what you should strive for uniformly. There are aspects of what he did that are amazing, but if he could have been around that with some of the other aspects of others, he would have even achieved more.

(Joel Beasley at 00:41:18) What's some of the best leadership advice that you've gotten, like, people have given to you, you've implemented, you worked it out, and you liked it?

(Jason Warner at 00:41:26) I think that the singular best advice I got was—there's two things. One is, like, it's a leadership neg. Like, I was told that I wouldn't achieve what I would want to achieve with my style. And at that point, and it was by a terrible person, an absolute drag on society type of person who I didn't just dislike. And that was, to me, the counter, the anti-advice, which is like, "Now I will show you" type of deal. However, he was right about one thing. You do have to make people money. And he said, "If you can make people money in your style, then you can have success." He didn't actually say that to me. That was my takeaway. His was, "If you make people money, that's success." What I realized in his statement, though, was you cannot have success that does not involve making people money or company money or an industry money. And your point about bringing a billion dollars worth of value is spot on. If you can bring the value with your methods and your approach, then you can have success. But if you have your methods and approach and don't have the success, you can't claim it. So that was something that I had to orient around. It's effectively in sports—you could be the nicest manager or coach or whatever, but if you don't win the championship, they're going to knock you. But if you win the championship, your methods start to get looked at more. So you gotta win. You always have to win. And once you win, do it your way. That's success.

(Joel Beasley at 00:42:58) Yeah. And you can't do it like that without being a worker, like working on your craft. Like, you gotta build the personal side and the craft side. Yeah.

(Jason Warner at 00:43:10) So the thing I've said is that there's two failure modes. And too often, we fall into one of the other camps. And one is you're only going to chase money or output or whatever, and you're gonna burn people out along the way. And this is where I—this is the camp I put Elon Musk, to give it what it's worth. And Elon Musk obviously is massively financially successful, and he's going to achieve that same output. But he does burn people out. And that is one variant on something. Then there's the other side of it, which is like, "I will become the best people manager. I will become the best culture person. I will do all of those sort of things." But if you don't achieve the success, this is a failure mode. Now, however, the industry is oriented towards people like Elon. Like, if you achieve massive financial success and you burn everybody out along the way, we as an industry do give him a pass or those people a pass. We do not give these other folks a pass. You cannot have the best culture and no output. There's no pass on that. So this is what my goal was, basically, to say, "I will show that you could have an approach that has massive success, and you can do it in a way that people want to be around you." And it's not because of financial reasons. It's because they have a greater mission and vision. They understand how you're doing it. They understand that you can achieve those sorts of things together.

(Joel Beasley at 00:44:28) I think you're outlining the book right now. Jason's Tech Leader book.

(Jason Warner at 00:44:34) I love it. I will admit, I think it's—I do think it's much harder, for what it's worth, because you have to account for a lot more things. It would be much easier just to go in and dictatorially command fiat type of methods and say, "Go do this or you're out of here and fired" and all that sort of stuff. And like, that is easier to do. And maybe my approach shouldn't be done because it's harder to do, but I also don't think I would wanna be that person.

(Joel Beasley at 00:45:00) It needs to—you have to be okay with who you are as a person while getting the job done, right? Like, I don't want to be that person. I don't want to leave that impression, you know. Let's just be decent humans and treat other people like we wanna be treated. Right?

(Jason Warner at 00:45:16) And but I think that there's the other side of it too. I think that then you end up in a territory where it doesn't matter as long as you have the financial—so this is something else I've said too. Actually, making money is not a hard problem. You could get into any of the seven deadly sins and make quite a bit of money. And in fact, there's investment pieces around investing in sin companies, or you can do nefarious things, or you can sell arms to Saudi Arabia and blah, blah, blah. There's a lot of ways to make money.

(Jason Warner at 00:45:42) But at the end of the day, what are you doing? What do you do? And so, you know, I do fall into a camp where I go back and forth even on myself. I said, like, maybe I should just go and work at Facebook and go do—but at the end of the day, I don't think I could actually rationalize that in my head when I'm 70.

(Joel Beasley at 00:46:01) Yeah. How do you deal with—alright. So you're doing these, what did you call them? Level three things or stage three things?

(Jason Warner at 00:46:09) Yeah. Horizon three. Yep.

(Joel Beasley at 00:46:10) Horizon three thing. So you're doing these horizon three things. So you have a team that's kind of working on experiments. How do you coach them around failure? Or does it not come up because of the culture?

(Jason Warner at 00:46:23) The thing is, with what I'm doing with the Office of the CTO, is you've gotta find a little bit more senior folks who are pretty resilient in and of themselves because the way I've described this is if you're doing horizon one, horizon two, or horizon three, you're basically gonna have different failure rates. And horizon one, it should be near zero failure rate, a 100% success rate, because you understand what you're building and who you're building it for. But if you don't have that, you've not done the correct product work at that point to get to that. So let's say that's anywhere from one year to 18 months out, and you should understand what you're building. Horizon two is anywhere from one year to two years, one year to two and a half, depending on the size of the company, all that sort of stuff.

(Jason Warner at 00:47:06) But your success rate there is probably gonna be closer to 80%. You should—you mostly know what you're building. You've got the customer feedback. You've done some, like, the co-dev with them or others in the industry to understand that. You're gonna have some failure, but 20% failure there should be understood.

(Jason Warner at 00:47:23) Well, with what we're doing, most of the things we're going to be doing will fail. We'll answer—and this is yet another way to not make a light bulb type of situation. And I expect that we should probably fail 80% of the time. Horizon two and horizon three should be inverted. And our successes should be massive.

(Jason Warner at 00:47:43) If we're doing something, it should be—we shouldn't be experimenting on something that is an incremental gain. It should be a monumental gain for the company or the industry. So how I coach them to think about these things, and this is why you typically need people who have experienced their own project failures in software already, is that success is answering a way to not do something. The project does not fail, quote unquote, because we said this is not worth our time. That is a success because we've told people that this is not worth our time to go do.

(Jason Warner at 00:48:17) So you almost have to reorient what failure and success is.

(Joel Beasley at 00:48:21) I love it. Boom. Jason, you're the man. We've got four minutes left. Anything else that we didn't get out there? I wanna be respectful of your stop.

(Joel Beasley at 00:48:28) So—

(Jason Warner at 00:48:34) No. I love coming on with you all. I think this is—yeah. I just have a good time talking. This is fun. I love your new digs. That looks great. Congrats on that.

(Joel Beasley at 00:48:39) Thanks, man.

(Joel Beasley at 00:48:42) Yeah. Well, you have a fantastic day, Jason. We'll talk soon.

(Jason Warner at 00:48:46) Alright. See you. See you.

(Joel Beasley at 00:48:50) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you'd like to hear discussed on the podcast, either add me on LinkedIn or send me an email [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.