Jason Warner - CTO at GitHub

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(Joel Beasley at 00:00:37) So if you're tired of long, boring leadership training from the 1940s, try something new and modern. Become more valuable as a leader at leaderbits.io. Now get excited because today we are talking to Jason Warner, the SVP of Technology at GitHub, and we discuss the different flavors of mergers and acquisitions, stepping out of your comfort zone in order to grow, and why it's so important to take ownership over the things you can control. All of this right here, right now on the Modern CTO Podcast. Here we go.

(Joel Beasley at 00:01:14) This is the Modern CTO Podcast. You feeling good, though, Jason?

(Jason Warner at 00:01:27) Yeah, it's a nice day up here, so, you know.

(Joel Beasley at 00:01:30) How are you? Where were you calling from, by the way? I know where Jacqueline is, but I don't know where you are.

(Jason Warner at 00:01:31) Where are you calling from, by the way? I know where Jacqueline is, but I don't know where you guys are.

(Joel Beasley at 00:01:35) We're in Florida.

(Jason Warner at 00:01:37) Oh, all right.

(Joel Beasley at 00:01:38) Tampa area, a little bit south of Tampa in a town called Sarasota.

(Jason Warner at 00:01:44) Okay. I know where Sarasota is. So is it getting springtime over there? I'm assuming so.

(Joel Beasley at 00:01:49) Oh, yeah. It's spring break crazy. It just ended, so the beaches were flooded with people. It was just chaos.

(Jason Warner at 00:01:55) Very nice.

(Joel Beasley at 00:01:56) But in a good way. And then where are you calling in from?

(Jason Warner at 00:01:59) I'm in Bellevue.

(Joel Beasley at 00:02:00) Bellevue? Nice.

(Jason Warner at 00:02:01) Bellevue, Washington.

(Joel Beasley at 00:02:03) How is it out there? Raining?

(Jason Warner at 00:02:05) It's not raining right now. You can see the back window behind me. It's full-on spring. As a matter of fact, my weather app told me that this week was gonna be—it's gonna start to rain towards the end of the week, but it's gonna be in the seventies, I think, at one point this week.

(Joel Beasley at 00:02:17) And so are you leaving Bellevue? Are you, like, "I'm done with the rain," or are you just moving places?

(Jason Warner at 00:02:22) No, I moved to Bellevue. I was in Victoria, British Columbia for five years.

(Joel Beasley at 00:02:26) Oh, okay.

(Jason Warner at 00:02:27) I moved to Bellevue from there after the acquisition was announced.

(Joel Beasley at 00:02:31) Nice. So I was checking out your Medium, and the first question I had was, where did you get all that artwork?

(Jason Warner at 00:02:40) So I randomly—I like urban sketching. That's one of my things. To relax, I do a couple of different things. One of them's write, one of them is lift weights, the other one is to draw. And I got into sketching and watercolors a while back, and urban sketching kind of took to it because, frankly, it looked like there was an easy way to get into it. You didn't need a lot of talent. You throw some lines together, slap some color down on it, and it looks pretty good. But you start to do it, you realize these folks are really ridiculously talented. And I started following some folks on Instagram or various mediums, and this one person—I don't know who this person is, but they're out of China. They just go all over China. They do this one style, and I just love it. So I just follow this person. I grab some of their free domain artwork when it pops up, and I just use it for blog posts.

(Joel Beasley at 00:03:28) It's beautiful.

(Jason Warner at 00:03:29) It's amazing, isn't it? You look at that and you're like, okay, yeah, that's how you know life's not fair sometimes. Someone's got that much talent, and also, their dedication to it is otherworldly.

(Joel Beasley at 00:03:40) Yeah. I saw the first one, and then I saw the second one. I'm like, "Is he drawing these? Who is doing this?"

(Jason Warner at 00:03:47) Oh, no, no, no, no.

(Joel Beasley at 00:03:48) I used to play around with this app called Paper, like Paper 53. You know what I'm talking about?

(Jason Warner at 00:03:53) Yep.

(Joel Beasley at 00:03:54) Yeah. You could do some pretty cool watercolor-type stuff in that app.

(Jason Warner at 00:03:57) There's this person on Instagram who I used to follow too until I completely deleted all social media at one point. This person's name was like Master Vie or Master Six. I'm not sure how you pronounce it, but they use micro pens, kind of like the Micron 0.05-millimeter-type things, and they would just constantly draw architecture. And what this person did was they just posted every single one that they did over a five-year period, and you could see the progression going back on their Instagram from when they just started to what they had become. And if you just found them now, you think this person is just godly talented, but you see where they start from. You can see the progression. It's kind of fascinating.

(Joel Beasley at 00:04:40) That draws parallels to me with leadership because I was reading your leadership stuff, and I happen to really like your style. But you can watch the leaders grow, and it's amazing where they go.

(Jason Warner at 00:04:52) Well, if you do it every day too, as you're managing people or leading, I made this comment a while back at a recurring event that I had gone to for many years, which said that, you know, today I'm no different than I was five years ago. And then someone came up to me afterwards and said, "No, no, no. You're very different than you were five years ago in a positive way. We could definitely see the progression." If someone's only seen you in snapshots over the course of once a year or twice a year or something like that. But you don't feel it every day. It's kind of interesting how that works.

(Joel Beasley at 00:05:20) Yeah. It's leveraging the compounding nature of time. It's like a superpower to people who understand it.

(Jason Warner at 00:05:29) Which is also why just start sucking money away when you're young too. I can't believe I'm in the forties already. I look back, I'm like, yeah, 1999 was just the other day. I'm like, oh my gosh, some people were born in '99.

(Joel Beasley at 00:05:43) I know. I can remember where I was in '99 because everybody was at the New Year's Eve party. I was wondering if the world was going to end.

(Jason Warner at 00:05:52) Yep, yep.

(Joel Beasley at 00:05:56) And there's a few towns that, like, their electricity companies went out and stuff. Those people must have been freaked out, like, the three or four small towns.

(Jason Warner at 00:06:06) If there was an April Fools' Day joke to be played, it would have been right around that time.

(Joel Beasley at 00:06:11) Right? So are you usually at home working from home, or is this just because of the move?

(Jason Warner at 00:06:18) I'm, let's call it 50/50 here at HQ in San Francisco. I've been a distributed remote exec now going on ten years at least. GitHub is probably 60-plus, 65%-plus distributed. Heroku was distributed. Canonical, the place before Heroku, was also distributed. So I've been doing this for quite some time.

(Joel Beasley at 00:06:39) Wait, so Canonical was what Heroku was before it was Heroku?

(Jason Warner at 00:06:45) Canonical are the people who make Ubuntu Linux. I was at Canonical for four and a half or five years, Heroku for three and a half or so years, and then GitHub. And all three of the places are distributed. Canonical is 100% remote. Heroku was probably about 65% remote, 70 or so in engineering. And then GitHub, same percentages as Heroku, 65% for the company, 70-plus in engineering.

(Joel Beasley at 00:07:12) And they just got—how long ago did they get acquired by Salesforce?

(Jason Warner at 00:07:16) Heroku?

(Joel Beasley at 00:07:17) Yeah.

(Jason Warner at 00:07:17) 2012. So it's been a little while, actually. I think it was 2012 that they got acquired. I joined them in 2014.

(Joel Beasley at 00:07:25) You know what's funny is I didn't even—I've been on Heroku for a long time, but I didn't even realize they got acquired for quite a while. Like, it was several years before I noticed. I don't know if that was intentional or unintentional.

(Jason Warner at 00:07:40) Intentional. A lot of the branding stayed the same for quite some time.

(Joel Beasley at 00:07:43) Yeah. And then they didn't change it too much. It just has this little Salesforce logo at the bottom.

(Jason Warner at 00:07:47) Yeah.

(Joel Beasley at 00:07:47) Yeah. But I spoke to Parker last week. He's one of the co-founders of Salesforce.

(Jason Warner at 00:07:54) Nice. Yeah, Parker Harris. I only interacted with him maybe a couple of times at Salesforce, but one of the more genuine people in the industry, I would say. I feel like the guy's otherworldly wealthy at this point, and you still don't feel it when you talk to him day in, day out. So I kind of appreciate that when you're around people who let things get to their head in the industry.

(Joel Beasley at 00:08:20) Right. It was cool. We were talking about his meeting that he had like 20 minutes before our call with his lead architects and stuff. I'm like, dude, you're still killing it. You're—it's amazing. That makes me happy.

(Jason Warner at 00:08:32) There is one story about Parker that I'll tell that I like, which is—I don't think he would ever remember this, but we're all flying to a leadership off-site for Salesforce somewhere. I think it was Palm Springs from San Francisco. Everyone was kind of coming into Palm Springs. And I saw him. He was on my flight. He was in, I think, row seven or something like that. So not first class, not flying private, not charter. He was in economy. And I remember getting on the plane, looking at him, going, "That's Parker Harris. He's in economy with everybody else." And then there were some other people at Salesforce at the time who were in first class, some people who chartered private to get to Palm Springs from San Francisco, which is, you know, what is it? An hour and a half, an hour or something like that. And I just remember thinking to myself, like, no matter what happens in life, be Parker. Don't be those other folks.

(Joel Beasley at 00:09:25) Oh, I love it, dude. I love it. Because you want to be that genuine, authentic person. You don't want to change too much, you know?

(Jason Warner at 00:09:33) Yep.

(Joel Beasley at 00:09:34) I love that painting behind you. Is that painting a print, the artwork of the little GitHub characters, different colors?

(Jason Warner at 00:09:41) It is. This is a sticker we have at the office, and I got this as a closing gift for the acquisition. So several of us on the exec staff and some of the VCs got this one. One of the investors, this guy named Jim Goetz at Sequoia, just commented randomly because we had a very large print of this in the office. I'm gonna walk him through. He said, "I love that one. It's my favorite one," and I just made the same comment. "I love it too." And next thing you know, my admin had sent one to all of us. She just got a bunch of prints done and she sent it out. And I got it three or four weeks later. And I just randomly asked her, like, "Hey, sis, did you—I got this." She's like, "Oh, I took care of that. I heard you and Jim talking, and I thought that'd be a really nice little gift for you all." And it's literally one of my favorite things to get out of the acquisition.

(Joel Beasley at 00:10:30) Yeah. Because it's beautiful.

(Jason Warner at 00:10:31) It's amazing, isn't it?

(Joel Beasley at 00:10:33) Yeah. Have things changed much for you since then?

(Jason Warner at 00:10:39) To a degree. Day-to-day work feels a little similar, feels similar to what it was before. Microsoft has taken a pretty hands-off approach to GitHub. We're an independent entity, much like you probably wouldn't have known that Heroku was acquired by Salesforce, as you mentioned. You probably shouldn't be able to tell that GitHub was acquired by Microsoft day in, day out. Our roadmap is largely the same as it was before. The biggest difference day-to-day for me is Nat Friedman, who's come in. He's my boss now. He's the CEO. And he's an engaged CEO, which is different than GitHub's previous regime. And he is really amplifying a lot of what GitHub had been and will be. So that's the biggest change day-to-day there. My personal life has changed because once you do something of this magnitude and your name starts to get out there, people approach you for many, many different things. So again, kind of like Parker, I've got to keep remembering that all this stuff—all this fame or flattery you get—is all ephemeral no matter what. You have to kind of remember where you grew up or who you are and what you wanted to be, and kind of let the noise wash away.

(Joel Beasley at 00:11:49) Yeah. Like, people inviting you on their podcast and stuff. Crazy people out there.

(Jason Warner at 00:11:53) This is the fun stuff. There's some—I mean, you get random out-of-left-field-type things every day now. And the fun part is you get flattering job offers, like amazingly big opportunities, and a lot of folks trying to get you to replicate the success in one way or fashion or form. But then you've got people trying to hit you up for money or "invest this way" or all the things. And then you just have random requests popping out of the woodwork from either old acquaintances, old friends, or even some old family stuff. And it's just interesting.

(Joel Beasley at 00:12:21) Won the lottery.

(Jason Warner at 00:12:23) It really feels that way. I'm like, I don't think y'all understand how acquisitions really work, so...

(Joel Beasley at 00:12:28) It's like, "Jason, buddy, pal, friend—" one of my favorite ones. "I want you to come work for our company. It's gonna be great. You'll do pure equity, right? And you're gonna make millions of dollars. We're gonna do awesome things."

(Jason Warner at 00:12:45) Basically working or drawing for publicity. You're like, "Cool. No thanks."

(Joel Beasley at 00:12:50) So you go to GitHub, and that's 2017, right, when you get there?

(Jason Warner at 00:12:55) Yeah. 05/31/2017 is when I joined.

(Joel Beasley at 00:12:58) So when you join, they were already—that's right before the acquisition started. If an acquisition closed recently, then they usually don't happen fast. So did you come right into it?

(Jason Warner at 00:13:10) There's only so much I can talk about.

(Joel Beasley at 00:13:13) We don't have to talk about this, by the way. We don't have to.

(Jason Warner at 00:13:16) Well, I can say this: Everyone in the industry probably knew what GitHub should be, what it could be. Very few people were able to come into GitHub and try to move it to what it could do, though. My job is pretty simple. I joined when it was about a $2 billion valuation. Mine was to get it ready to be acquired or IPO. Either one of those options had to be on the table, and organize it, drive it, give it a mission and vision that sounded palatable to suitors or the market. And once you show that you can be acquired and you have a palatable vision out there and there's a degree of FOMO that you've created, things happen fast. So we announced the acquisition on my one-year anniversary to the public. We announced it on my one-year anniversary. And I would say that end-to-end from interest to announce was less than six months, and then total of nine months to close the deal. So it did happen fast.

(Joel Beasley at 00:14:19)
Yeah, that is actually really fast. That's cool, though. So I guess where my root of my question was is, like, when you got in, you were instantly working in that because if you're senior executive at a company being acquired, so you don't have an opportunity to not be a part of that, right? I just was curious if you—

(Joel Beasley at 00:14:34)
Yeah.

(Jason Warner at 00:14:37)
I would say that the time I joined in May, May 31st, I was able to get Microsoft, Google, and others on the line probably closer to October, November. That's when all the conversations probably happened, earlier as early as they probably did.

(Joel Beasley at 00:14:51)
Oh, that's very cool. So just out of, for you and me, right, and the audience, people often will ask us questions like, can you give us some advice on M&A, or can you talk to people who've done that? And it doesn't have to be—we're not gonna do specific stuff with GitHub or anything like that. Just in general, you know, things to look for. What would make—I'll give you a hypothetical. If I have a company and I was looking to get acquired, what would make me valuable? What would you look for?

(Jason Warner at 00:15:24)
Oh, I mean, it's a very general question, and it's obviously gonna lead to a whole bunch of "it depends" answers. However, I think that people can get acquired for a couple of different reasons. Let me give you a broad view sense that I have for what product really is in the world. And I think I stole this—I know I stole this from someone, and I think it was Geoffrey Moore who I stole this from, which was product comes in three different flavors. You can say you're neutralizing competition, you're optimizing what you have in the market, or you're kind of innovating. And, you know, where you are on your growth curve kind of depends on how much investment you're making in any one of those areas for your business. But M&A actually comes in the same flavors. You're trying to buy your way out of competitive situations and gaps, or you're trying to buy innovation because you lagged, or you're trying to buy some optimization. And you typically don't buy optimization. That's not what you spend money on.

(Jason Warner at 00:16:19)
So it usually comes into the other two buckets: neutralization or innovation. And understand which one of those scenarios you're in if you're talking to potential acquirers or you're looking at M&A. Why are we doing this M&A? Or what are they trying to get out of this? Are they thinking they're getting a market leap to leapfrog competition, or are they trying to get a catch-up play? And, you know, it depends on who's acquiring you on which one of those modes it's in. And if you look around, many people think they're buying innovation, but what they're really doing is they're buying gap. They're trying to shore up holes in their business that's a competitive gap. And that's pretty much—you know, neutralization is a pretty common M&A strategy.

(Joel Beasley at 00:17:01)
I like that. I like that a lot because we have a startup here alongside the podcast, and I actually didn't know what I was doing when I got into the business. It just kind of happened. Yeah. I was like, whatever. I was like, I had people knocking on the door asking for lemonade, so I was like, let's open up a lemonade stand, right? And then I realized, oh my God, this is an $18 billion market. There's this whole thing. And then I started—you know, it grew, it did whatever, and then I decided to raise capital to grow it even farther because I was like, it's growing. Look at that. That's pretty great. And then people were asking me questions like, how—what's your exit strategy, right? And how—so I had to do some market research. And then I started learning that you've got all these older companies. And what will happen is some new technology will come out, and then a competitor to that new technology will come out, and they're playing in the $15 to $30 million range. And then a third one comes out, and they're like, oh my gosh, they're gonna steal our market share. So then big guy number one buys this one, big guy—and then what happens is you get this tension in the market where there's a supply and demand issue. There's only so many new, innovative, competitive companies, and the big people are buying them up fast. And so when I was researching my industry, I saw that that was actually happening. I was like, this is perfect timing because in two years, there's eight or nine of these guys that need to stay relevant. The two biggest leaders have already made acquisitions for the company that I am, like that style of business, and there's no one else. So I'm gonna—it's gonna be like me with eight bidders. And I was like, that's at least right now. And so I was like, that's actually pretty cool, and that's my first entry into M&A.

(Jason Warner at 00:18:38)
Well, I think that you kind of nailed it on the head. You see this happen. What happens—I mean, the entire—all of us are humans. We're all kind of driven by the same type of dynamics at play. And I think if you just understand the human dynamic at play is wins and losses, fear of missing out, competitive situations, and all those other things really do come into play. And, you know, one company buys another company. Next thing you know, three competitors are saying, what just happened? And they're trying to react, and they're reacting quicker. And, obviously, the faster you make decisions with less information, the worse that decision might be too. And all of a sudden, this froth happens in the market. It's just a weird frenzy that can actually happen when a competitive situation emerges.

(Joel Beasley at 00:19:19)
Yeah. And it ends up awesome sometimes for parties involved. So let's change the topic a little bit. I'm curious because you are remote some of the time, I'm curious how you grow and develop your next generation of leaders, like technology leaders. I saw you write a lot, and you're very smart about culture and leadership. But how do you sort of—how do you do that on a tactical level?

(Jason Warner at 00:19:49)
So the one skill I find that you need to be remote more than anything is the willingness to pick up the phone, as I say, which is you've gotta be able to jump on a Hangout or a Zoom or a phone call—way back when—to be able to do it. And video has changed the game entirely for remote. When you were just doing audio conferences, it was much, much, much harder, and I don't think it was nearly as successful. And no matter what anyone says, IRC and Slack and all the other ones are not an acceptable alternative for video. And I find that if you're not willing to do that—you wanna stay async entirely and just use text-based communication—it's very, very difficult to do that. You have to have mixed modes. So you've gotta be able to write. You've gotta be able to async, write and consume, and you gotta be able to jump on video to hash things out. If you're able to do that, I find that all of them kind of wrap together, allow you to have a pretty good experience. Every once in a while, I think you should get together in person, but I don't think it's necessary to be doing that every week or even every month. And, you know, your mileage may vary, but your willingness to get on a video call like this is key to doing it.

(Joel Beasley at 00:21:01)
So you mainly coach your leaders through one-on-ones when you're on video and communicating like that?

(Jason Warner at 00:21:07)
We do Slacks back and forth just to do check-ins and the, you know, the first time you ever sense any sort of miscommunication on even a back-and-forth of a text-based communication, you're like, good, gotta jump on the phone. Let's go right now. Let's jump on the video Hangout because the most important thing is to clear up small issues before they become big ones and then also talk through scenarios. If you're gonna do this scenario stuff, talk through them live because nuance is very difficult in text. Talk through them when you can see the other person.

(Joel Beasley at 00:21:37)
Ask my wife, right? Nuance is very difficult in text. So you don't get to where you are without being able to understand this concept of stepping outside of your comfort zone, right? And so if we've got some—you know, a lot of our audience, first-time team leaders, all the way up to leaders of leaders, and then some CTOs, but a whole lot of first-time tech leaders. What sort of advice would you give or share or story you would share about stepping outside of your comfort zone?

(Jason Warner at 00:22:11)
Oh, wow. This—I could go on for days in a kind of meandering, probably no real point at the end of it type of thing on this one, and I do like to talk about this stuff.

(Joel Beasley at 00:22:23)
One good story. One good stepping-outside-your-comfort-zone story that yields a positive result.

(Jason Warner at 00:22:29)
Oh, well, I would say for me, the acquisitions one—it's not very often that you try to talk about stuff like that—stepping out of my comfort zone, but, obviously, the payout was huge. I would say the first time I really jumped into management is kind of one of the first ones. I'm what you might call a reluctant leader. If I look back on my career, I jumped into management really, really young. I went back to IC, jumped again, went back, jumped, went back, kept doing it over and over again. And finally, there was a point in time when I was kind of burning the boats on engineering leadership and just went all in on it. And I remember the time I did it was because I was so incredibly frustrated with what was going on around me. And it was one of those moments where I love the company. I love what we were doing, but everything was a mess. And, generally speaking, most things are on fire, or, you know, there's some degree of emberness that is happening, smoldering, if you will, that is happening at all times. But this one felt particularly on fire. And, you know, I stepped up and I said I wanted to go help. How can I help? And I went and I had a very uncomfortable conversation. This is the stepping out of the comfort zone part. I was young, and I had a very uncomfortable conversation with the CTO at the time. And you could see that this person almost had this sense of relief because this person was like, God, I know everything's on fire, and I have no idea what to do. What can we do? And you can see that there was this guard-let-down moment where I was like, I don't know. You don't know either, so let's just talk about some of the things and prioritize top five that we should go after. And that was my first real jump into management professionally without just kind of dabbling at it, which led to executive management, you know, six, eight months later, and then the rest is history.

(Joel Beasley at 00:24:17)
I like that because what you're describing is you saw an issue and you looked around and you're like, hey, nothing's happening. And then you stepped up outside of your comfort zone and you made some changes and figured out how to solve the problem.

(Jason Warner at 00:24:31)
Well, in that one in particular, the uncomfortable conversation with a superior was the really step-outside-your-comfort-zone one. But there's a way in which you can do those. I like to say that every conversation is a chance for net improvement or decline in a relationship. And there's a way to have a conversation—a difficult conversation with someone where you become closer and stronger, form bonds outside of it, even if it's you're not gonna work at this company anymore. Or you can have that same conversation, and next thing you know, you've got a villain for life that's coming after you. And the skill is finding out how to have those conversations, and most people don't know how to have those conversations. And I think it's an actual skill to develop—difficult conversations.

(Joel Beasley at 00:25:14)
Is there a book for that or—

(Jason Warner at 00:25:16)
Well, there's a book called Crucial Conversations, which is a good one to read up on. There's also, you know, candidly, my son is autistic. I have three children, and my oldest is autistic, and my second has many learning disabilities. And I've read a lot about a concept called social thinking, but also how to express yourself for kids on the spectrum and how they communicate. And for some reason, for me, when I was reading a lot about communication and patterns in autistic children as well as social thinking theory, I was able to figure out that there are modes of communication that most of us don't employ, and we take short-circuit shortcuts through most of our conversations. And if we don't take some of the harder portions of the conversations and develop those skills, we're actually doing all of ourselves a disservice. And we're trying to train on social norms, if you will. And that only applies usually to very specific geolocals or maybe a nation or two. But I've lived all over the world, and there's many people in this country who don't—or you work with who are not born in your state or your county or your country, and the social norms are not the same. So sometimes you actually have to have a deeper ability and sophistication in communication than you normally would, and one normally would. So, yeah, I think you have to develop that.

(Joel Beasley at 00:26:39)
So you've lived in about three different countries?

(Jason Warner at 00:26:41)
Yeah. United States, Australia, and Canada, and then back to the US. And then I've worked with people from all over the world, obviously.

(Joel Beasley at 00:26:51)
Oh, nice. Did you just do that because you were remote and you could, or were there offices there and you—

(Jason Warner at 00:26:56)
My—so life happens sometimes. All the time. And, you know, we were young. My wife and I, we had one kid at the time. Something happened in our life, and we said, hey, she—we wanna make a change. Let's move to Australia.

(Joel Beasley at 00:27:12)
Yeah.

(Jason Warner at 00:27:12)
So she looked for a job. She figured out what she could do there. I ended up at Canonical. It was either gonna be a remote company or nothing for me. I was running engineering for a startup, but you're kind of blowing up the situation. And if I could find something remote and able to do it, I would. If I couldn't, then we were still gonna do that. And so that's how we ended up over in Australia, stayed there for a couple of years, almost three. Then we found out about our son being autistic, and we're like, hey, we gotta get back to North America, but let's look up and down the West Coast for the best possible situation for us. Found Victoria, fell in love, went to go do that for five years, and then, you know, again, life happens, and here we are in United States after the acquisition was done.

(Joel Beasley at 00:27:53)
I love it. And you guys are happy where you're at?

(Jason Warner at 00:27:55)
Yeah, we're pretty happy. The kids love it. My wife likes being back in the States. One thing that I think that particularly Americans either don't learn because we grew up here or maybe forget if we traveled abroad is how easy things are in the US and relatively how cheap things are. So there are obviously some things that are harder. I personally prefer the Australian medical system to the US medical system. It's got a mix of public and private. So there's amazing social safety nets, but also the ability to jump outside of it and do private if you need to or want to.

(Jason Warner at 00:28:30) It's actually quite a good system, in my opinion. But, you know, everything else is a little bit harder there, and same thing in Canada. But, like, gas is cheaper, groceries are cheaper. As ridiculously expensive as real estate is here in some cities, it tends to be cheaper here, or at least relative to income levels. Amazon.com is a thing in the United States, and it's not a thing in the country. Amazon.ca is, but assume that there's one-hundredth of the inventory at Amazon.ca as opposed to Amazon.com. And, you know, it's just these little tiny knock-on effects. So it's nice to be back.

(Joel Beasley at 00:29:07) What age range are your kids?

(Jason Warner at 00:29:10) Eleven, eight, and five.

(Joel Beasley at 00:29:12) Eleven, eight, and five. Nice. I've got eighteen months and one that's four weeks.

(Jason Warner at 00:29:21) Oh my goodness. Yep. You're a unit.

(Joel Beasley at 00:29:25) Yep. So you know what my life's like right now.

(Jason Warner at 00:29:29) And I'm laughing because is that coffee you're drinking at, what is it, 7:00 at night or 6:00 at night on your end? Because you need it, actually, I would imagine.

(Joel Beasley at 00:29:39) Yep. Yep. I found—I used to think when I was young, I was like, how could the parent fall asleep on the couch? Like, how could you just fall asleep? It's like the middle of the day. How could you do that?

(Joel Beasley at 00:29:49) And then I thought I had a sleeping problem because I couldn't fall asleep on demand. I have two kids. You could fall asleep anywhere you want.

(Jason Warner at 00:29:59) Having kids is a remarkable perspective for the entire world. And yes.

(Joel Beasley at 00:30:05) So let's talk about this. We had this little inside conversation at the office. I mean, it was a small debate, but I'm curious to get your perspective on it. We're discussing personal development, like professional development, like improving yourself, and whether that's the responsibility of the individual or the company to improve the individual.

(Jason Warner at 00:30:27) So I find that this is actually quite an interesting conversation because I think it goes to mindsets all around the individual as well as the corporate body. So here's what I say: assume that no one is going to be responsible for you the way that you can be responsible for you, and assume that you have to take your responsibility into your hand. However, look for places that care for you the way that you would want to be cared for. And if I look at it that way, my job as an executive leader is to try to provide opportunities or things, growth opportunities or forums in which people can do those things.

(Jason Warner at 00:31:04) But I'm also looking for people who are going to own it themselves because, one, that shows a drive on their own and a more assertive attitude or approach to their own care and cultivation. If that's how they're going to care for themselves, it likely transfers to other aspects of the job as well. And there's a statement I live by. The longer I've been getting into my career, I like to look for people this way. I forget who said this, but it said, "You try to find people you need to rein in, not people you need to motivate."

(Jason Warner at 00:31:33) And, you know, I think my job is actually to motivate and inspire. That's my job. But if I'm looking for a trait in a person, I should be looking for a person who I don't need to do that for as much as

(Joel Beasley at 00:31:46) you might think you need to.

(Jason Warner at 00:31:48) And if you combine those two things, magic can happen, because you found, you know, leadership that might care, but you also have people who are really self-driven. There's a lot of stuff that you can conquer in that approach. So to answer that question more directly, I think it's both parties. If I were to lean, it's going to be—probably, I'd say the individual should absolutely do it because there's very few people who will care about them the way they care about themselves.

(Joel Beasley at 00:32:09) Yeah. That's—first of all, that was my side of it, because individual ownership's like everything. And the logic behind that for me is that if it's your fault, then you have the capacity to do something about it. But if it's outside of your control, you put yourself in a lost situation. Like, you can't do anything about it because it's outside of your control.

(Jason Warner at 00:32:32) Well, there's very few things in life that you can control anyway, right? So, like, most of life is like a random number generator, it feels like. However, you can take control over at least your education, your—not your experiences even, because you might not get opportunities provided to you even if you apply for them.

(Jason Warner at 00:32:50) But you can learn, you can read, and you can research. You can at least take control of information that flows into you and how you reflect on it.

(Joel Beasley at 00:32:58) Yes. Yeah. And you can—that's the beautiful thing about humans. Like, a horse is a horse. Like, it can do horse things. We can study. We can learn art. We can learn to draw those great drawings that you were talking about earlier. We can do anything that we want, you know, with our brains if we put the time into it and execute the discipline to do so.

(Jason Warner at 00:33:18) Another way to say—some people are asking all the time about maybe a mentor or things like that in my life, getting to this point. And I have had only one person at one point in my career who I think even cared for me as a species called human, let alone as an individual person. And I had a very short period of time with that person. It was less than two years, and I enjoyed every minute with it, particularly as time has gone on. But in a, you know, twenty-plus year career, I've never had it except for that one opportunity.

(Jason Warner at 00:33:52) So if people are asking me how to find a mentor or any of those things, I say it's quite hard, actually, because it's very difficult in our industry that people assume that someone else is going to provide them with opportunities. And I did that early on. I assumed the good work that I did was going to showcase, or everyone else is going to just look at all the work and just throw opportunity my way. It doesn't work that way, typically. And it's unfortunate it doesn't work that way, but it doesn't.

(Jason Warner at 00:34:18) And the reality of a situation is, whether you use the word "should" or "shouldn't," like, "I shouldn't have to do that" or "it should work that way"—"should" is a useless word. You have to actually figure out what the reality of the situation is and how to navigate and get through it. Now, if you're in a position to change the entire narrative of the industry or the situation or whatever, that's different. Most people are not that, including myself. I don't control my own career at Microsoft.

(Jason Warner at 00:34:41) Things have to fall my own way. People have to take a liking to me. There has to be the right political environment for me to achieve success past my current gig. I don't control that. I'll control the small few things I can, and everything else is going to be luck.

(Joel Beasley at 00:34:57) But that's the beauty of it, because there are things you can control.

(Jason Warner at 00:35:01) So I'm going to take ownership over those, and I'm going to control them.

(Joel Beasley at 00:35:04) Yeah. I like it. It's almost amorphous. Like, you can sort of control certain objects in the environment, but you can't guarantee the exact outcome. But you can put everything in the right area and do what you can do, and then have a healthy environment.

(Joel Beasley at 00:35:21) And you're confident that if you have that healthy environment, a positive result will yield.

(Jason Warner at 00:35:26) Well, there's this comic I love about climate change, which is—there's these two folks at a conference room full of, it looks like, other scientists. And they're speaking to each other, and they're talking about all these different initiatives that we could do to combat climate change. And one says, "Hey, what if we do all this stuff and we make the world a better place for nothing?"

(Jason Warner at 00:35:45) And I think of that when I think about some of these things. Because if you and I are working at the same place and the inputs are generally the same, we're taking control of our careers the same way in our learnings, and we're progressing—we might, the outcomes are not guaranteed to be the same. You and I might have different outcomes. You might end up as CTO of the place, and I may end up on a project that never had success for whatever reason. But that doesn't mean that it was worthless effort on either of our parts, because you have to play it out over the time horizon of careers as well.

(Jason Warner at 00:36:13) And even if the outcome was not the same, it's not fair—life generally isn't fair—but there's also going to be a moment in time where we are better than we were before, and that to me is the broader goal.

(Joel Beasley at 00:36:25) Yeah. And when you're saying that, it's reminding me—you know that whole money one, if you'd rather have a penny and double it or you'd rather have just, like—well, if you look at the math of that, and this was an interesting one for me because I did it the other day. You don't actually get the payoff greater until, like, the last two days. Like, it's always a better option to take the money upfront until this, like, very last moments.

(Joel Beasley at 00:36:48) And so, like, that's—for me, that's motivating. Like, I'm going to keep improving and keep doing that step even, like what you said. Some might end up as a CTO, some might end up as a failed project. I'll say there's some gold in that failure of that project, and now let me go at it again. And eventually, over my career, it'll compound, and I'll just get better at identifying opportunity, better at adjusting the environment and improving myself.

(Joel Beasley at 00:37:10) And I've yet to meet a person or read a book of someone that's tried really, really hard for a really long time and not have had a lot of success.

(Jason Warner at 00:37:20) Well, it's this classic—I think we all see them, which is when do people have success in their life. And, obviously, some people have immense success really early on, their one hit wonder, and never have another success after that. But they can have huge monetary wins, and they never have to worry about that again. And then you have others who achieve what you might think of as their life's work in their forties, fifties, sixties, and seventies. And, you know, it's staggering for people in their twenties to think—you know, you look around Silicon Valley and San Francisco, and, you know, Lyft IPO'd yesterday and a bunch of other things that'll be happening, and, you know, you have some mid- to late-twenties people thinking, "Oh my God, I'm failing at my career because I'm not X, Y, or Z because of whoever else is around there." And it's a skewed perspective. Sometimes the situation dictates the outcome. You just have to prepare, find the opportunities, be prepared for when you're in that situation, take advantage of that one.

(Joel Beasley at 00:38:14) Yeah. That's a good point because I had this transition in my life about, I don't know, five or seven years ago when—yeah, I had some early success with building applications. I made some really good money really early on. And then I didn't have that much success, and then I had a little bit, and then I did, like, alright. And then, like—but I didn't want to just do alright.

(Joel Beasley at 00:38:32) Like, I had early success, so I didn't want to just do alright. And then I started thinking a lot and reading and, you know, finding experts and things like that that have gone really far in their lives. And inevitably, they're always writing about it when they're, like, in their sixties. Right? But I decided to make a mental change from investing in the exception-based investment, which is "I'm going to build the next multi-, you know, hundred-million-dollar app, right?

(Joel Beasley at 00:38:58) And I'm going to kill myself and I'm going to compromise my health and I'm going to do everything and write as much code as I possibly can. And I know if I do it, like, I've got a shot at huge, huge money and being a household name." And then I realized, "Look, all these people say it took forever and you have to play this incredibly long game." So now instead of, you know, binging all night on coding and ignoring my health, I'm going to eat right, work out, invest in myself, figure out this professional development, learn how to communicate better, understand the business world better, and I'm going to play a twenty-year game because that's what all the successful people do. And if you're doing the 80/20 thing, I'm—if I'm investing, this is our life here, man.

(Joel Beasley at 00:39:39) Jason, this is our entire lives. You get, like, one shot at a lifelong thing. And so I'm like, "If I'm going to make this one investment, I'm not going to do exception-based thinking. That's playing the lottery. Instead, what I'm going to do is I'm going to play the rule.

(Joel Beasley at 00:39:52) And I'm going to invest and do the hard work over extremely long periods of time and know that if I fail on the rule, I will be proud of myself."

(Jason Warner at 00:40:01) I can appreciate that approach. I think that Silicon Valley teaches us to try to swing for the fences, and obviously there's incentives at play. So if you're on your side of the fence and you're an investor on the other side of the fence, their incentive is actually to get you to play the exception-based game because that's how their game is played. But if you're on your side of the fence, play the rule-based game. That's your side of the fence. That is the higher chance of a successful outcome.

(Joel Beasley at 00:40:27) Yeah. It's working. It took about five years before I first started seeing the signs of it working, but it was okay because I was healthier and, like, more fit and I felt better about myself. And it was just—I adjusted my expectations rather than being stressed about not hitting it all the time. I'm like, "I'm only a few years into, like, a twenty-year plan. I'm good."

(Jason Warner at 00:40:52) I think a longer-term plan is a healthier one—mentally, physically, emotionally, family-wise. You have to also balance it, in my opinion, for what you want to do out of life. Some people actually want to play the exception-based game, and I think more power to them. And when I was younger, I thought I wanted to as well. And I decided that I was going to do it one more time with GitHub.

(Jason Warner at 00:41:12) But, you know, after that, I don't know.

(Joel Beasley at 00:41:15) What are you most excited about today? Like, what's the thing that you're—probably the move being over?

(Jason Warner at 00:41:21) Yeah. It'll be nice when the move's over. You know, the things that get me out of bed in the morning are still—I like what I do. I like what GitHub is building. People who see what GitHub has slowly released over the last couple of, let's say, year and a half or so since I joined can probably put together what we're slowly going to do over the next five years as well.

(Jason Warner at 00:41:40) And that to me is very interesting. I like developing the future, which is a little bit opaque to most people. I quite like that. And I'm pretty excited about being able to do that and continue to be able to do that. So I consider it a privilege.

(Joel Beasley at 00:41:54) Yeah. I'm a big fan of GitHub, by the way. I've been on there since 2009.

(Jason Warner at 00:42:00) Very early. Yeah. Nice.

(Joel Beasley at 00:42:02) Yeah. Yeah. And, uh, it's been great. And, I mean, pretty much since the moment I—since I, I don't know, since I started writing big boy technology and not just small fun projects—working with teams, like, I didn't—it took me so long to figure out that there was this thing, like, another technology that did that, because for me, Git was, like, the only thing, but there was other versions of it and stuff like that. But I was like, "Oh, man."

(Joel Beasley at 00:42:29) If I—as I matured as an engineer. Like, I wish I would have known about—you should have seen my face the day I figured out what tests were. I was like, "This would have been so useful."

(Jason Warner at 00:42:41) I'm old enough to remember the days when we were having, like, SourceSafe or Perforce or ClearCase discussions, and then I was at a startup company that was on CVS trying to make the case to move to Subversion. I was like, "Oh my goodness. These are tedious conversations," branching and tagging conversations. And I remember when GitHub first came out, I looked at it and I was like, "Oh my God. This is going to change everything."

(Joel Beasley at 00:43:06) Yes. Are you doing any public speaking in the near future?

(Jason Warner at 00:43:10) I do a lot of internal stuff at GitHub and Microsoft. I will be doing—I don't think I have any public things coming up. I just got done with South by Southwest, and I have a CTO summit in New York, I think, in June.

(Joel Beasley at 00:43:23) That's Peter Bell, right?

(Jason Warner at 00:43:27) I'm not sure if it's that one or if it's a different one.

(Joel Beasley at 00:43:28) There's two of them that are going out of San Francisco.

(Jason Warner at 00:43:29) Really?

(Joel Beasley at 00:43:31) Yeah. Oh, nice. Let me know about, like, who organized it. Do you know who organized the other one?

(Jason Warner at 00:43:37) I think it's Benchmark Capital, actually, was doing it.

(Joel Beasley at 00:43:39) Benchmark Capital?

(Jason Warner at 00:43:40) Yeah, I think that's who was doing it. Well, I'll find out later and send it to you.

(Joel Beasley at 00:43:44) Yeah, I'll kind of geek you out about that type of stuff.

(Jason Warner at 00:43:46) Yeah, yeah. I always give the same type of talk. So if you ever look up to one of the old CTO summits in San Francisco from Peter Bell, I give the same type of talk, which is about building organizations that can scale and thrive over time. So it's all the same type of talk. Most people—I find that when they're building companies, they try to do things that worked for them in the past, not realizing that that's going to break at a scale that they're probably not anticipating at the moment. So I talk about how to do things and how to plan for future growth that way.

(Joel Beasley at 00:44:19) Oh, that's pretty cool. And that obviously—I mean, it's like, if you gave that, you know, back in the day, right, or a few years ago, now when you're giving it, it's like a whole different—you got all that added experience on top of it.

(Jason Warner at 00:44:32) Yeah. And my wife looks at it this way. She's always wanted me to continue writing. That's what she likes that I do. And she just—she wants me to keep writing about that experience, like, all the—if anything, GitHub is like a pressure test of a lot of those theories or theses that you put into practice at smaller places or in different situations, because GitHub was kind of like the pinnacle of those things. It was, you know, largely VC funded. It was in an interesting spot in its history, a lot of positives and negatives, and to get it out this way is a validation of a lot of the principles.

(Joel Beasley at 00:45:08) When's the book coming?

(Jason Warner at 00:45:10) I don't have—it'll have to come after I don't need to work or want to work anymore, I'll say.

(Joel Beasley at 00:45:17) That's good. Well, here's—I'll—we got this book coming out, working on it, and it's the habits and patterns of the greatest technology leaders on the planet. And essentially, it's just like, you know, Salesforce CTO, you, Kevin Scott over at Microsoft CTO, like, all these different technology leaders, VPs of engineering, SVPs, CTOs. And I took, like, the best clips from all the, you know, 500 conversations I've had with them, and I'm putting it into a book, and I'm organizing it by, like, here's the best bits on culture, and here's the best things on hiring. And so if you'd like, I'd include some of your content in that, and then now you need a book.

(Jason Warner at 00:45:55) You've got the blog post. You can freely adapt any one of those, or we can talk about something else offline if you want.

(Joel Beasley at 00:46:01) Yeah. No, I just think it'd be—I like—in first of all, the coolest thing about all of this is, quick backstory about me. Started programming at eight, been writing code for about seventeen years, knew nobody, like four or five people until two years ago. And now I know, like, hundreds of people. And it blows my mind because people are always like, why are you so excited? Why do you talk so much? Like, because I didn't say anything for seventeen years.

(Jason Warner at 00:46:29) Nice.

(Joel Beasley at 00:46:30) Yeah. So now that I get to, you know, hang out and talk with people like you about leadership and technology and all the cool things that they're doing, it's just super exciting. So I just like to include people in projects that we're doing and I get to travel around the world and speak. And, like, I go to Colorado tomorrow morning. I was in San Francisco last week. But, yeah, it's a lot of fun. So if I'm ever out in the Bellevue area, I will—

(Jason Warner at 00:46:57) I go basically fifty-fifty at this point. So—

(Joel Beasley at 00:46:59) Oh, between SF and Bellevue?

(Jason Warner at 00:47:01) Yeah.

(Joel Beasley at 00:47:02) Oh, yeah. I ran the bridge.

(Jason Warner at 00:47:05) Oh, yeah. Nice.

(Joel Beasley at 00:47:06) It was scary, dude. Have you been on the bridge?

(Jason Warner at 00:47:10) I've been on the bridge with cars. I don't know if I would go on foot.

(Joel Beasley at 00:47:13) You want to talk about, like—I had the best Tony Robbins thing in my head. I was like, you do not look over that edge. Where you look is where you will go. I was like, I was writing a leadership talk in my head because it is scary. The rail is, like, you know, waist high, and there's people on their bikes coming, and there's cars over here, and then you hear the water, and then all you get—

(Jason Warner at 00:47:36) The wind can whip up a little bit too.

(Joel Beasley at 00:47:37) Oh, damn.

(Jason Warner at 00:47:38) I remember I was standing—I don't remember where this was—but I was standing way up in a building, and it had one of those plexiglass or glass-based floors where you can look down below you, and there's just a street. And I'm just thinking, nope. That's not for me. So you all have fun with that. I'm just gonna be over here hanging out by myself.

(Joel Beasley at 00:47:58) I'm glad there's a personal growth wall there, because that wall is gonna keep me alive.

(Jason Warner at 00:48:03) Yeah, no need. That's not for me. You're all good. I know what I'm about.

(Joel Beasley at 00:48:07) Awesome. Jason, this has been fantastic, man. I'm so glad that we got a chance to hang out and talk.

(Jason Warner at 00:48:12) Well, thanks, Joel. This has been fun.

(Joel Beasley at 00:48:14) Yeah. Alright. Talk soon, Jason.

(Jason Warner at 00:48:16) Alright. See you all.

(Joel Beasley at 00:48:17) See you. Thank you so much for listening. If you'd like to help, please take a moment right now to open up the iTunes app and leave a review of the podcast. If you take a screenshot of the review and text it or email it to a friend who needs to listen to the podcast and then CC me, [email protected]—if you CC me on the email, I'll send you a copy of the Modern CTO book or give you a shout out on the podcast, whichever you prefer. We're trying to get listed on the top 100 for iTunes, and I need your help in order to do this.