From Chef to System Initiative

Well, Adam Jacob is back. I’m solo, because I think every time you’ve been on this podcast we’ve talked about things happening, or things going on, and not so much about what you’ve done.

That’s true.

I mean, you’ve sprinkled some stuff in there, of course… But never Founder’s Talk meets the Changelog meets Changelog & Friends. And that’s what this is. This is Changelog &Friends. So friends listening to this, this is a different flavor of Friends, so buckle up.

Yeah.

I kind of want to go into your journey a bit. I mean, you’ve been on the show I think four times directly, a fifth time indirectly, because you were too busy to record, things happened… And that’s when Elastic versus AWS happened, and we had to borrow previously recorded stuff that was pertinent… And it worked out well.

Yeah. I was even great when I wasn’t there.

There you go.

Do I get a jacket? Is it Saturday Night Live?

We’re actually getting some Pied Piper inspired jackets made, the Rat Pack jackets…

Love it…!

Not sure if you’re familiar with those, by any chance…

I am.

But I’m looking forward to those very colorful jackets on my back. But Changelog flavor, not Pied Piper.

Yeah, obviously.

Silicon Valley reference, just so you know… So Adam, where did things begin? I heard – tell me if this is true. I heard that you became a system administrator at the age of eight.

Well, I mean, that’s a bit of a leap.

Okay… So that’s not true.

I mean, it depends on how we define it. So my mom was a real estate agent, and I’m 46, so I don’t know. I’m terrible at arithmetic, so I’m not sure what year it is, in the ’80s, the early-ish ’80s, you know?

Your what age again?

I’m 46. So it was probably… I don’t know. ’86, in that general zone.

I’m one year younger than you, so we’re in the same ballpark.

Yeah. So anyway, mom was a real estate agent, and PCs were a thing, that you could buy. And so she bought one that had a modem, because she wanted to be able to dial into the MLS… That’s the multiple listing service, for people who didn’t grow up the children of real estate agents. And it was where all the houses are. When they list houses, it’s the database you could go look at. And so you could dial into this bulletin board, and the bulletin board was the MLS. And then I thought it was awesome, and so you couldn’t keep me off the thing, from both playing video games, because obviously, but also, that modem meant you could just call bulletin boards. And so I have an older brother, and my older brother had a friend who he’d been on bulletin boards… And so he immediately showed me that bulletin boards existed, and how to call them, and I was just “Wait, wait, wait, wait, wait… You can just call other people’s computers, and then do stuff, talk to them?” You know, you could page the sysop, and it would ding their computer, and they would hit Spacebar, and then you could chat with the person who ran the bulletin board. And I just thought that was the coolest thing that had ever happened.

And then I discovered FidoNet. So FidoNet was an early version of email. So there was like [unintelligible 00:07:22.04] So you could build – and what was cool about FidoNet was it was basically like a regional network. So what happened is every bulletin board would call a central bulletin board… Or sorry, the opposite way. So the central bulletin board, with a central hub, would call all the bulletin boards in an area code, and then collect all their mail, and then make one single long distance call. And so everybody would sort of pitch in to cover the long distance fees for transferring your mail… And you could send mail all over the world. And the thing that blew my mind - because this was like peak Cold War - was you could send email to Russia. So you could talk with Russians over FidoNet. And so eight-year-old me – and no one knew how old you were. And so I was like a precocious eight-year-old or whatever, and I thought that was super-cool. You could play role-playing games, like play by email role-playing games, which I was all the way into… So yeah, I immediately loved bulletin boards. And then was like “I’ve got to run my own bulletin board.” So I was annoying my parents, because I immediately signed up for FidoNet, and was using my allowance to pay the long distance fees…

[00:08:30.03] That’s hilarious.

So the bulletin board would call mine at like two in the morning, the phone, and I had it so the computer would pick up only in that small window… And so every night at two in the morning, the phone would ring once, and wake my father up, and then he’d go back to sleep or whatever. And eventually, they were like “What the f**k is happening with this phone call happening at two in the morning all the time?” and confronted me about it. And I was like “Oh, yeah. Well, oops…”

So yeah, I loved bulletin boards. I ran bulletin boards forever, until bulletin boards weren’t a thing. I ran a bulletin board in high school that I gave all my friends, because internet access was still rare in the early ‘90s… That’s how I sort started running Linux, was I’d run – I was running OS/2 Warp, because I wanted multiple phone lines, because you could multithread… And then I discovered Linux. And probably in ’89 or ’90 - it could have been ‘90. I don’t know, early slackware, pre Red Hat… Anyway, so I wound up – had a bulletin board where you could dial into it, and then if you knew the secret code, it would reboot the computer and boot into Linux. And then my friends could dial into the other line, and then log into my system, and then dial out to the internet using my ISP. And so I just gave all my friends internet access by letting them reboot my bulletin board.

Wow.

I loved that stuff. So fun. I still love it. It’s the funnest thing.

That’s interesting. A lot of detail in there, really.

Sorry. [laughs]

No, what I mean by a lot of detail in there is by no means what you shared is that is that that’s where the curiosity begins. And I think that’s why it’s kind of interesting to kind of just dig back into that kind of cliché question, which I really hate leading with, which is “How’d you get started?”

I mean, that’s how I got started.

I know.

I mean, I was all-in. I was taking it apart… I had a job where I worked in a comic book in a role-playing game store. It sounds idyllic, because it kind of was, now that I talk about it this way…

The times, man. Those were the times.

They were great. So I would save some of the money that I wasn’t spending on comic books and I would spend it on gear, you know? And yeah, it was great. I still – when I think about my life and I think about my career, I still kind of think of it as one unbroken arc from discovering that it was awesome to talk to people on computers, and my whole life has just been somehow facilitating people talking to each other on computers, because I just think it’s so cool. I like doing it, but I like making it happen even more, you know? I just love – I just really the details of it, and I like how computers work, and I like how you put them together, and I think operating systems are cool… That’s been the vibe the whole time.

At what point did it go from hobby to “Wow, I can actually do this as a career”?

Yeah. So one of my old friends, still one of my best friends - we see him all the time; comes to family dinner every couple of weeks - got a job at 16. I already had a job, because I was working in a [unintelligible 00:11:32.06] store, but he got a job working for this ISP. So to sort of set the scene for people who aren’t as old as Adam and I - the way the internet happened, in the United States anyway, was very grassrootsy. So it started out with lots of tiny mom and pop ISPs. In this case it was a very mom and pop ISP in Vancouver, Washington, that was in the back of a dentist’s office. So you walked through the dentist’s office, people were getting their teeth worked on and stuff, passed oral surgery, and then you would go into the back office and they took one of the back office rooms and turned it into a data center. A data center… They had a couple of half racks. And we put modems in them…

Switches, and…

[00:12:13.24] Yeah. And then they were running – there was a FreeBSD server and a Windows NT server, and that was the ISP. And so he had gotten a job doing tech support for them. And they wanted – they were looking to hire another person, and so he wound up… He was like “Hey, my friend Adam can totally do this.” And then I immediately was like “I want to be the systems administrator.” And there was this very cool kid that was the systems administrator. He was this older kid that was in the community college or whatever, and was into Skinny Puppy, and had safety pins in his face, and like…

I have no idea what Skinny Puppy is.

Skinny Puppy is an industrial band.

Okay. Yeah, that’s–

It should set a vibe.

Okay.

If you think of that early ’90s cyberpunk, that vision of what the future would be - he kind of looked that.

Sure. Okay.

When that was still a thing you could be, and you were being actually edgy, instead of like Hot Topic. It hadn’t quite reached Hot Topic yet.

Right. I Googled some images and I’m seeing what I’m seeing, and it’s very large hair, very mascara…

Skinny Puppy?

Yeah.

Yeah, sure, because that era was – it also overlapped with hair metal, you know?

Sure, yeah. You had to have massive hair.

Yeah, yeah. He didn’t really have massive hair in my memory, but I didn’t know him for that long. He had a hot girlfriend, I remember that. I thought that was cool.

All black leather…

Yeah, definitely.

Strong cheekbones…

Yeah, lots of German cheekbones.

Sure.

Anyway, I thought that was incredible… But he was also kind of a slacker, because this was the least interesting part of his day. And it was the most interesting part of mine. So I would just do work for him, you know? Because he was, whatever, too busy, by which I mean not there, you know? And it was great. And yeah, so I was 16, 17. Probably 16, 17, something in there. Because the memory gets hazy, you know? And then I went to Arizona, ostensibly to go to college. I was a terrible student. I had a 166 GPA. Strong D average. I graduated high school because I would cut class, obviously, because nobody who doesn’t cut class gets a D average. And like a total loser, I would hang out in the library, and I had befriended one of the librarians, and so she would let me cut class and hang out in the library. And so I was cutting class and hanging out in the library, and we were talking about how I wasn’t going to graduate.

The library had still books of all the Washington state law, you know? They would still publish them in volumes; it was like the Encyclopedia Britannica, or whatever… And she found this loophole in state law where you could be concurrently enrolled in college, and high school at the same time. And if you dropped out of high school with six months left, then they just froze your grades as they were when you dropped out, and graduated you anyway… And so I basically concurrently enrolled myself in college and then dropped out, and then graduated through the college as an adult, which means you don’t need all of the extra credits for the vocational stuff. You can just graduate with 40 fewer credits than you normally could. I told all the kids in my high school how to do it, so 20 of us dropped out all at once. It was great.

So you dropped out.

So we dropped out, went to Arizona, got a job at another ISP, and… Yeah, it was that or running a children’s theater, and the ISP paid better.

Okay. So you traded ISPs, essentially. You went from one in Vancouver to one in Arizona via a loophole in the law that let you drop out.

[00:15:45.08] Yeah. And I had another teacher who was very upset that I wasn’t going to go to college. So he was like “If I find you a college, you have to go.” And I was like “Sure.” And so he did. He found DeVry, before DeVry was really that big of a deal. There were only two DeVrys. And yeah, so I wound up going to this – I wound up going to DeVry in Phoenix, and was there for what a trimester. So I was there for one trimester. Because I’d got this job working in this ISP, and it paid as well as the average degree graduate from DeVry. And so my mom was like “Hey, do you–” you know, I called my mom, and was like “I think I should drop out, because I’m getting paid.” And she was like “Oh, you should probably talk to the guidance counselor.” And so I went to the guidance counselor at DeVry and told them what was up, and they were like “Yeah, you need to quit. The thing everybody’s here for is to get a job that pays what you – so just… You should not be here.” And so I called my mom back and was like “Guidance counselor said I should drop out.” Bam. So yeah.

And then those ISPs, in that era - it was a big growth time for getting everybody on the internet. So the big thing everybody was doing in technology was just getting people on the internet. So that first ISP I worked for was in someone’s garage…. All sorts of fun stories that I can’t really tell about that ISP.

Really?

No, I really can’t.

What makes you not be able to?

It’s complicated. The people in this era, sometimes the people who ran ISPs were – I’m going to say sketchy. So if you talk to people who worked in that era in ISPs, they almost all have stories where they’re somehow connected to mobsters, and drugs…

Really?

Because it was a growth mom and pop industry, where you could make a lot of money very quickly, and it took some capital investment. And so you can see how it’s comes together in a certain shape. And so everybody I know who worked in that era, if you ask them, they have a story like that. And I have one too, but I can’t really tell it, because the people who were involved in that story - they’re good people who I really like, and I don’t need to talk about them on a podcast.

So it’s easy to trace you back to the company, and probably easy to find their name.

Yeah, exactly. And I don’t need any of that. But rest assured they’re funny stories. I shouldn’t have even mentioned it, but…

Well, now you got me curious and upset.

Yeah. Okay. I know. Let’s just say that there was a moment where law enforcement showed up to work.

Oh, gosh.

I was at work, then there was a knock on the door, and then law enforcement arrived… And then all was revealed unto me because the folks in law enforcement knew my boss, and it was like a normal harassment kind of thing. They weren’t harassing him, they were harassing his father… And so it was like you were in a movie and they were making those – when there’s the one good son, and then the cops come to harass the good son, and he’s like “Bobby, what are you doing?” It was like that.

Okay.

It was crazy. I have other friends who you should definitely interview who would probably tell their stories about like - they were setting up early satellite internet connections, and having to explain the speed of light to drug cartels… It’s a whole thing. It was weird.

Really?

Yeah. Anyway, so…

It’s so wild how there’s a lot of – at least there was in a popular TV show I mentioned earlier in the show called Silicon Valley, where porn was very influential in the innovation of various tech on the web.

All of it.

Right?

Yeah.

And then you have this scenario here which I was never aware of… I’m aware of mom and pop ISPs. I grew up in the same era. I’m very aware of this whole push to say “Everybody needs to get on the internet. This is the–” It wasn’t about what was on there necessarily. It kind of was a little bit… AOL definitely [unintelligible 00:19:29.25]

There wasn’t a lot there.

Yeah. There wasn’t a lot. But it was about getting access to this worldwide web, this – what did they call it? The information highway.

The information super-highway. You could still go buy the book that gave you all the best URLs.

Yes. I mean - -yeah, you could buy a book with URLs. That’s a whole different era of the internet. We would never imagine that being the case now. You might buy a book and it’s got like one or two URLs in there.

[00:19:56.14] Yeah, no, but it was just a book of screenshots, you know? Of Netscape Navigator, and you know, Yahoo.com.

Yeah. That’s wild.

It was wild.

Just to see that crossover of nefarious folks, let’s just say in the space of innovation.

Yeah. Well, it always happens, right? If there’s a growth industry that happens really fast, it’s obviously a thing where you can fraud, and all kinds of stuff. Now that I’m talking about it, it happens a lot.

What’s a modern day version of it?

I mean, you see this in startups all the time, where the requirements to be a founder are pretty minimal, if we’re being honest… And so founder bad behavior. It’s not hard to go look at founder bad – like, they’re making Hulu movies or whatever about people’s bad behavior, and the fraud that they commit. And it’s kind of the same, where there’s access to money, compelling ideas… It can be tempting to sort of blur the lines. Because if you’re running or you’re founding a startup, you’re always hyping a little what you’re doing. You’re always a little telling a future story about what could be, or why it’ll be exciting… And then there’s the reality, and there’s a fine line between elegantly talking about what you think is true and what can happen, and lying.

And I think in the middle there was all the consolidation of ISPs that happened, and that was another interesting era… So I worked for an ISP that was run by the Arizona Public Service company, which is basically the power company in Arizona, and we brought phone lines to a bunch of rural parts of the Southwest, that had no phone lines in the ’90s, because the power company had a pop in there, so they could deliver power. They had power, but no phones. And so we brought them phones so that they could get on the internet.

And that consolidation – the guy I worked for was a nuclear scientist, who had been running the nuclear power plant not that long before. He was fantastic to us, but he let me be the – I was in the first crop of Red Hat certified engineers. It was me and four people from IBM. And that was because my boss at the time sent me off to get trained or whatever. But yeah, you wound up with this – it was a very interesting arc. And then as the consolidation happened, so everybody sort of pooled together all the ISPs into super-ISPs, then what you started to do is the focus shifted toward what you were going to do on the internet, right? Because now everybody was here, so now you had that sort of first generation of internet companies. And that era - rife with fraud. Crazy amounts of fraud.

So I worked for a company, Infospace… This is a story I can tell, because f*** that guy. So… Maybe I shouldn’t. Now that I’m saying it, I’m like “Oomph.” But anyway, he was a bad dude. Naveen Jain, who ran that company, was some degree of awful kind of all the time. And they didn’t really have a business model, but there was a moment in time where Infospace had a market cap that was bigger than Microsoft.

Really?

Yeah. Because Naveen was just an incredible salesman. He would hype you up about whatever it was, and you were just like “Okay. Yeah, he seems great.” And in reality, he was kind of a monster. But that company was huge. There were thousands of people working there… We were running corporate infrastructure for them, and production infrastructure… It was crazy what was happening. And yeah, I think there’s quite a bit of crossover fraud. Not to turn it into the fraud show or whatever. It makes it sound like my entire career was full of crime. But…

Adam… You’re a bad guy. You’ve worked with bad guys.

I’m not. I was the guy who when they tried to fire him, for example – so they tried to kick him off the board, because he was a bad guy. And so the people that I had actually worked for - I wound up working there through acquisition. This is actually an interesting story. So I wound up working there through acquisition. I was working for this company called GoToNet, and they got bought by Infospace.

[00:23:59.08] Then what happened was the GoToNet guys basically staged a coup. Tried to. And I was the lead systems administrator for all the corporate stuff, so I had set up all the automation for your accounts and stuff, your email. And so they had told me in advance that they were going to have this board meeting, and that they were going to fire the CEO, and that they were going to call me. And in that moment, as soon as I got that call, I needed to turn it off stat, because I didn’t want him to leave the boardroom and write an email and be mean. So I had to turn everything off immediately.

So they called me, and I turned everything off, and then time goes by, and I get another phone call, and they’re like “You’ve got to turn everything back on.” And I’m like “We don’t really have a back on… You know?” I have the off automation, but there wasn’t really a back on, so it’s going to take a minute… So yeah, it turns out that what had happened was he had staged this coup, and he threatened basically to take all of the revenue, all the contracts, many of which were in his name, across the street to a new company that he was going to start, and bankrupt them. And so the board then decided to fire the guys that I had worked for, who had tried to kick him out, and then it took years for him to finally be replaced. His investors just relentlessly pushing him out of that company… Which eventually died the death it deserved. It was a company that had no real revenue, had no real products, but thousands of us worked there, doing stuff. It was crazy. Yeah. That was what it was like in Web 1.0 for a lot of people.

It was like a web beta, or something like that. Not [unintelligible 00:25:34.14] because like –

It was like what could be, not quite what is.

Yeah, because nobody knew… Everybody was just trying to figure out what stick. And you had no idea. And everybody who was on the internet was stoked, because they were like “I’m on the internet. New stuff’s happening!” And it was awesome, but it was insane, and often strange.

So then I went to work for another company, it doesn’t really matter… But then I wound up working for that same set of executives, the initial set again, at another company. And I loved the team, and there were a lot of the same people that I’d been working with for a long time at this point, at a company called Marchex. And they had a business model that it was at least clear, if weird, which was basically they would pick a vertical, they’d pick like targeted ads, and then they would consolidate the fourth, fifth and sixth biggest players in the game. So they would buy them and then smoosh them together and it would sort of spike the revenue. And our job was to compress the spend. So basically, we built a machine that could just slurp up people’s companies. So if you ran a targeted ad company, we could buy you, and then we would show up and look at how you ran the software, and then port it to the automation that put it on our gear. And then that would drop the cost to serve, which would then spike profit. And you can see how that sort of turns you into a profitable company over time. And yeah, so I worked for them for a while, and we did that a lot. Tons of interesting stories kind of live in there. Yeah.

You’ve had some adventures.

Yeah.

I’ve enjoyed this seemingly tangent we’ve been on, but I’m really curious about – it doesn’t sound like you went to school to learn what you learned… So you kind of learned by doing, right?

Yeah, yeah.

Learned by passion, maybe, and obviously by doing… And you mentioned FreeBSD, and you mentioned Linux, and this is ’89 era…

Yeah, it wasn’t even FreeBSD, it was BSDI.

Okay.

Yeah, and it was mostly Linux. So Linux changed my life. As soon as Linux showed up and suddenly I could see all the source code, that was a revelation.

Did you actually look at the Linux source code though?

Yeah, yeah.

Because I’ve never looked at the Linux source code personally, ever.

Yeah. I mean, when you could get it on floppy disks, and then you suddenly had this – like, I loved operating systems. But you couldn’t see the source code to DOS, or OS2, or Windows… But Linux, I was like “Whoa. I can read man pages for everything, and I can look at the source code, and I can figure out what to do.” And I learned what a compiler was, and all of that stuff happened because Linux happened.

[00:28:10.20] And then there was this huge community of people who were so giving with their time, and so giving with their focus that they really were… It was very supportive as a place to learn. And when I was working for that ISP in Arizona, I patched the Red Hat installer. So there was a bug in kickstart that made it so we basically couldn’t automate the installation of this ISP that we were building. And so I patched it and sent them the patch, and they accepted it, you know? And suddenly that was – it showed up in an errata, you know?

Wow.

And then when they IPO’ed, they sent me a little thing and were like “Hey, thanks for the patch. Here’s your friends and family thing”, you know? It was great. The early era of that – that era was very… It was really rich and interesting.

And it was also where I saw the first people – I became a free software person, so the idea that that was important… That’s how that happened for me. So why I care so much about open source and why I care so much about licensing and all that stuff is because if it wasn’t for that moment, I can’t imagine how my life could have possibly evolved in the way that it did. Because I didn’t go to school. Nobody did teach me. What I had was this incredibly supportive community and this rich access to information… And those two things sort of allowed me to catapult myself into a different place.

It’s interesting how pivotal Linux is to so many people’s lives. And just the idea of open source. I mean, I have a similar story - not the same, obviously. I haven’t been to 17,000 different ISPs with various nefarious folks involved or not involved, like you have, and have the journey that you had, but…

Yeah, it makes it sound I worked for crime families. So I didn’t.

I mean, you may have, Adam. I mean, it sounds like you may have, honestly.

[laughs] Maybe just the one, but not –

Just the one…?

Not like a lot.

Yeah, sure. I mean, you worked for a company that was staging a coup. I mean…

I mean, boardroom coup…

You were in Succession, basically. You’ve lived a movie.

I wasn’t in the room. I was just the nerdy kid they called –

You were the kid in the back that was told to push the off button, and then suddenly push it back on, and there was no on button.

Yeah. And then I had to push the off button for thousands of people, and that was a bummer.

Did you watch the TV show Succession?

I watched a lot of it. I didn’t watch all of it.

Man, I couldn’t put it down. I was into it. It was really well acted.

It was incredible. Yeah, I just – it’s so dark.

It is dark.

At some point the bleakness overwhelms me, and then I have to –

Yeah, I can agree with that. There’s so much backstabbing, constantly. I couldn’t imagine. I was thinking – is that how billionaires with way too much money act in family?

It makes you not want to be one, right?

Well, yeah. I mean, it was really disgusting. But I couldn’t stop watching the train wreck.

I get it.

It was just – all the way to the very end. I’m curious, though, about an ISP stack… Is it boring? Is it fun? In those early days what was the stack to run an ISP?

Oh, yeah. I mean what you had were sort of –

And from hardware to software. Give me a rough breakdown.

Yeah, yeah. So in the in the very beginning you had – in the dentist office it was racks of regular PC modems you could buy off the shelf, plugged into PCs that were just loaded up with serial ports. And then eventually there was specialized hardware that you would buy, that just had racks and racks of modems. And then it evolved over time. In that early era there wasn’t a whole lot, and mostly you were running it on Solaris. If you had money, it was Solaris. I don’t know why they chose BSDI in the early days, but they did. But if you had capital, then you were running all that stuff on Sun gear. And so for a lot of people it was Solaris for all the stuff that matters, and then racks of modems that got ever denser, sort of as time went by.

[00:32:07.01] I think peak, for me - we were running Red Hat 4.2 in production at the ISP in Arizona… Which - that was us. Me and my friends were the ones who decided to do that, and saved a bunch of money, because we weren’t buying Sun gear… So we were just putting rack-mounted systems together, either by hand, or eventually buying them, and then sticking them in the closet, basically. And then - yeah, that was that was pretty much of the stack. And then you were running Apache, and for us we were running [unintelligible 00:32:42.18] QML for email… And yeah, that was about it. You know, you’ve got your home directory, and you could put up your little website on it, or whatever… And yeah, other than that – oh, DNS, of course.

For sure.

I was a big DJB person, so there was a lot of – we were running qmail, and we were running his DNS server, and we were running all that stuff… And yeah, that was pretty much the stack. And then eventually the stack grew, so… Again, money shows up, consolidation starts to happen… So the coolest consolidation story I have was this set of old McCaw Cellular guys, who had made a bunch of money when McCaw Cellular got sold to AT&T; we made a deal with the tribe in Phoenix. So there’s a reservation sort of in the middle of Phoenix, kind of, that now has a casino. That casino, the bootstrapping money for that casino came from these McCaw Cellular guys. And what they did was made a deal with the tribe that they could build a huge data center on tribal land, and they filled it with modems, and they put in their own class – I think it was a class three switch. This is a long time ago, so somebody is going to be like “It couldn’t have been class three. It was class two”, or whatever. But they put in a phone switch that could do long distance phone switching. And then they got the tribe to put in a tariff. So any long distance call that wound up getting terminated at their giant switch, they got 10 cents. And then they split it between this telecom company and the tribe. And so then they went around to all the ISPs, and went “Stop running your own POPs. We’ve got all the modems, and we’ll just route the traffic directly to you. So just buy colo space next to our huge bank of modems, and then you don’t have to manage all the modems anymore, and you can just run your gear right next to it, and then we’ll take a nut every time.” And the guy who set that up was humongous. He was – I don’t know, in my mind he was 6’8”. He wasn’t that tall. He couldn’t have been. But in my head he was like an ogre. He was huge. And as soon as you went in there, the first thing he would do is take you to his office and show you his bathroom… Because he had a custom-built urinal that was made for him. it was a huge floor to ceiling urinal, basically, and he was incredibly proud of it. And then he would leave you with cigars. One of the racks in the data center he had turned into a humidor. And so every time you went in, he would hand you a handful of Arturo Fuente Short Stories and kick you out the door. It was great.

Mm. Interesting. That’s like a weird version of cloud in a way. It’s like modem cloud, right? “Come colo next to me.” It’s very similar to the cloud story, right?

Well, because that’s the story. It just happens over and over and over. We’re seeing it now. It’s going to repatriate back to the edge again. We’re going to wind up seeing more and more people not running in the cloud, both for the cost savings, but also because it turns out it’s a superpower to understand how the stack works. And so one of the things the cloud has done is sort of abstracted people from the details. But in that era, there were only details. So everybody knew all the details, and it was still a superpower to know them, but you couldn’t do the work if you didn’t know all the details.

[00:35:57.06] Now you can do a lot of work without knowing anything about how any of this stuff actually works. If you need a load balancer, you can just make an API call and get one. You have no idea sort of how that’s working or what the stack looks like. I remember when load balancers – when we first built them, when there weren’t load balancers, because nobody had enough load.

So this is the era that you learned Linux… Well, learned about Linux. Linux affected your thought process around open source. At what point did you really come to understand the true importance of open source? Not just yourself, to your personal story, but then everybody else, to then eventually found a company that would be open source.

Yeah. There’s a couple of things. So Miguel de Icaza and Nat Friedman - Nat Friedman would go on to be the CEO of GitHub, and a bunch of other things… They started a company in the early days called Ximian. I don’t think that was the original name, but basically they were the GNOME company, and they raised venture capital. And I remember when the news broke that they had raised venture capital, and that everything that they were doing was open source… And at this point, I had already decided that the game here was figuring out how to start a business and make a bunch of money. And so working in Arizona, we were all contractors, because you couldn’t get a job working for the power company, because it was all unions, and they didn’t want the ISP arm to be unionized in that way… And so we were all contractors…

So we started our own contracting company, and hired everyone, and gave them all a 20% raise, and just took a smaller net, you know? So we were already kind of in that zone of like “How do we figure out – let’s figure out how to make a bunch of money”, basically. “Obviously, there’s a bunch of money to be had. We should get some.”

So when they started Ximian, I remember being like “Oh, man. It’s all open source.” They described how they were going to make money… I was like “That could work.” You could have all of the goodness of the openness and the sharing, and that could then make you into a bigger business. And that was the first time that that entered my mind, that what you could figure out how to do was build open source and then use the success of that open source to sort of catapult you up in business.

And then there was a series of others that sort of moved in that early era. There was VA ,Linux and the people that now run one of the Red Hat clones, Rocky Linux. Those guys had a company called Linux Care, that’s sort of infamous for its terrible booth babes. When you look back on it now, it’s “Oooh… Bad…” You know?

Wow…

So there was a couple of those things happening. And then Red Hat, of course, happened. And I loved Red Hat, and they treated everyone so well in that era, really… And when Red Hat IPO’ed, they made a ton of people wealthy, and I was just like “Yeah, that’s the way. We should figure that out.” And it was obvious to me that it was important on a philosophical level, because it had made such an impact on my life. I had this career, I was making more money than any of my friends were… We were doing well, and that was all because of Linux, and it was all because of open source… That ISP that I was running Red Hat on - they loved me, because I had saved them tons of money.

And I think what evolved over time was that there was a – I love that strain of human goodness that lives inside of open source. I love that ethic of sharing, and that more is more. The pie can get bigger and then everyone can eat. That’s such an ingrained thing in me now. But yeah, it was very motivating and very, very real, and it felt achievable… But then you have to figure out how to do it, and so it was like – we tried to start a half a dozen businesses, and failed… But eventually, basically, those same guys that I worked for for a long time at Marchex… Marchex went public, and I had a pile of stock, and I hadn’t made any money (not meaningful money) from any of those companies I had worked for… And so they had IPO-ed, and my stock basically vested, and for the first time it was also above water. So I would have made - yuo know, not life-changing money, but meaningful money. It would have been life-changing at the time, because I didn’t have a savings account, because whatever, I was a kid and spending every dollar…

[00:40:32.24] But in order to sell my shares, I needed to get a signature from the chief legal officer. And there was this coterie of executives who had been doing this together this whole time, and they had all become fabulously wealthy… And so I went into their office and I was like “Hey, can you sign this piece of paper for me so I can finally sell these shares for my decade of dutiful service?” or whatever. And he was like “No.” And I was like “Well, but I don’t have any proprietary information about it. I don’t know any special secrets or whatever. Please, can you do this?” And he was like “No, because it would inconvenience me.” This is what he said. “It would inconvenience me, and our CEO, and all my friends.

So no.” And I was like “Just no?” He was like “Yeah, just no.” And so I picked up my piece of paper and I left their office and I walked out of the building and I called my best friend who had built that ASP with me in Arizona, and I was like “Hey man, you hate working for IBM. These people obviously don’t give a **** about me, you know? So we should start a consulting company. I’m done. I’ll go find us clients and pay your bills, so you don’t have to quit your job until I find us people who will pay us. But we’ll go build automation and we’ll build fully automated infrastructure for startups.”

And so I walked, and started a consulting company. And we started building fully automated infrastructure for startups.

And that became HJK Solutions. So me and [unintelligible 00:42:05.26] And then we added some more people, Barry Steinglass and a few others. And eventually, that became Chef.

But it was the same people dreaming about how do we figure out how to start a business, how do we figure out how to build a company that IPOs? How do we figure out how to do all of this? We wanted it, but we didn’t know how to get it, and so we just kept taking shots, you know?

Break: [00:42:34.25]

Is it H-J-K? Is that right?

Yeah.

So you created a consulting company… Did you essentially do it by yourself, and then bring in clients, and then enable your friends to join you? Is that kind of how it panned out?

Yeah, so I found the first contract where – basically, what we sold was you’d pay us a fixed fee and we would automate everything. So application deployment, monitoring, trending, operating system installation, identity management, backups, database management, all that stuff. So a big, long list. And we would fully automate all of it for a fixed fee. So you’d pay us 20 grand and we would deliver all this automation. And then you paid us a retainer to maintain it. And the fastest we ever turned around was 24 hours. So we had someone sign the contract and pay us 20 grand, and then 24 hours later we’d fully automated everything they did. It was great. We were murderers.

I’m not sure you should say that given the history you’ve shared.

[laughs] But this is how I met Jesse Robbins, who is sort of integral to the Chef story. So Jesse was the master of disaster at Amazon. And if you ever meet him, he’s a larger-than-life human. He’s an incredibly motivating person. He has a deep and foundational belief in both himself and other people. He’s a lovely person.

And it was Jesse who was like - -we tried to recruit him to our little consulting company and he was like “No, I’m not leaving my job as the master of disaster at Amazon to come join your fucking consulting company. But if you build a product, call me.”

And so we had grown, we had a couple of people working for us, mostly our friends… We had maybe a dozen clients…

And we were using Puppet at the time. We built all that automation on top of Puppet. And there was this horrific moment where Puppet had this – it had two things wrong with it. So one was we were automating more than most people were with Puppet, and so the way Puppet was designed meant that it wasn’t very repeatable. So you’d build this big graph, and then you would do a topological sort of the graph… And topological sorts are random, basically. And so sometimes the graph would sort in a way that worked, and sometimes it wouldn’t. And the answer was just run the automation again, and hope it sorts itself out. Or figure out the bug in your graph and fix the bug. Either way, what it meant was we would sell all this automation to these people, and it would work 100% of the time, 80% of the time. And then 20% of the time it just wouldn’t work at all. Or it would take five times as long. And people didn’t love that. And so that was frustrating. And then there was this bug where suddenly files at random would start getting overwritten by checksums. So you’d have your resolve comp file or whatever would just go away.

What…?

And it would be replaced with just a checksum.

No way.

Yeah, totally.

That’s the worst ever.

It was so bad. So this happens to our biggest client, right? And I hop on IRC, and I’m like “Yo dogs, have you seen this horrific thing happen?” And the channel is like “Oh yeah, we know about that one”, and links me to the bug. And I’m like “What?! You know? What memo did I miss?”

“And this isn’t fixed?”

How did this not pop to the top of the community stack? I was paying attention. I was pretty involved. And I didn’t know. So anyway, this bug comes in, and in the bug report - it’s filed by this kid in New Zealand. And he files the bug, and Luke responds, and he’s like “I tried to reproduce this, and I couldn’t make it happen in the lab, and I’ve spent as much time as I’m willing to spend on it… So unless you’re willing to pay me for a support contract, I’m done.” And I was like “For real?” You know? It just overwrites files with checksums, and you’re just like “I’m out?” And he was like “Yeah. I’ve gotta eat.” And I’m like “Yeah, man. I have to eat, too. We should fix this bug.” And he was like “Well, you should pay me, and I’ll fix it.” And I was like “Um, what if we just worked together? How about I put my labor toward figuring out what the bug is, and we solve this problem?” He’s like “No. If you do that, you’re taking food out of my children’s mouths. And you should–”

…go somewhere.

“Don’t do that.” And I was like “Dude, I’m not paying you. I’m not going to pay you money to fix this bug. I’m willing to fix it, but I’m not willing to pay you to do it. I’m willing to put my own time against it, because I’ve got a consulting company to run”, we weren’t making that much money… It’s not like I had the cash laying around. And so I went to the person who filed the bug, and I was like “Hey, can you get this to happen reliably?” And he’s like “Yeah, absolutely.” And it wasn’t reliable for us. And so I was like “Great, can you get me access to the system that does this reliably?” And he did.

[00:50:15.05] And so he gave me access to the system in New Zealand, and I spent a week figuring out this bug, and we fixed it. And he accepted the PR, but was very angry at me, because I had undercut his model, and taken food from his children’s mouths.

And so I was like “This probably can’t stand. We can’t continue to be – I don’t want to be the consulting company that is the best in the world at this technology, but the guy who writes the technology hates us.” That’s not a very tenable business position. And they were completely uninterested in talking about the other problems I had with the system, which was like “Hey, at scale you’ve got to figure out how this big graph works. It’s a mess.” And they were like “You’re an idiot. If you weren’t such a big dum-dum, this wouldn’t be a problem.”

And so I started writing Chef on the side. So my partners took over all of the work, and then I essentially took a couple of months and wrote Chef, intending to use it for our consulting company. But then it was so cool that I showed it to Jesse Robbins, and Jesse Robbins was like “We should raise venture capital for that. Let’s f****g go.”

And so Jesse joined us as the CEO, and we raised venture capital, and I showed it to Ezra Zygmuntowicz at Engine Yard, who - rest in peace, Ezra - would have written Chef if I hadn’t written it. He was already thinking about doing it. But I had written Chef, and he was like “This is what I want.” And so before we even publicly launched it, we used it to automate Engine Yard, and then to make it available to Engine Yard’s customers. So we had a pretty great launch, and Ezra supported us, and the rest is history.

Wow. I can remember some DMs with Ezra… And I was sad, because obviously, he passed away… And I had met Ezra around at the Engine Yard offices in San Francisco.

Yeah. [unintelligible 00:52:05.05]

I didn’t live there, so it was a big deal for me to be there and to meet him, and even hang out with him.

They were so generous.

They were. They were so cool. He’s like “Come on in.” We went upstairs, and sat down on the couch… The two-story [unintelligible 00:52:16.04]

Yeah, that’s where we perfected Chef.

There you go. That’s awesome. And I was like “Dude, you’re so cool.”

He was so cool.

“You run this company… I mean, you’re just so cool.”

He was so cool.

And I think it was – I forget what year he passed away. It was several years later. But I wanted to get him – obviously, I’m a podcaster. I wanted to get him on a podcast, eventually. And I was going through my brain of people that I’ve met over the years that were influential to me, and I was thinking “Gosh, man… Ezra. It’d be cool to get him on the show and just share where we’re at now.” This is post, way post Engine Yard. But that was the foundation for so much.

So much.

And like the early Ruby hosting days, for sure, but then also a lot of the cloud development that’s happened, and stuff that. It was just pivotal.

Oh, yeah. Way ahead of his time.

It was, yeah.

But when you think about that early internet, and the culture and the people and open source, Ezra is a perfect example. Ezra had no ego about – Ezra a hundred percent could have written Chef, and it would have been a bigger deal than me. I didn’t matter. He didn’t have to do that for me. Like, he had all the resources in the world. He had the best Ruby programmers, he had everything he needed. But because I showed up and I had the thing that was basically what he wanted, and I was willing to hang out and do the work with him to make it work the way he needed it to… Not only did he help me, he incredibly raised our profile. Because he was the most high-profile person in that space at the time, in infrastructure. He’d literally written the book on Rails deployment and production. And he was just so thrilled to help us, and to move that forward. And if he hadn’t done it, we wouldn’t have been as successful as we were. And he didn’t have to… He did it because that’s who he was, and because he believed in open source, and he believed in all of those things as deeply as we did. And yeah, I miss Ezra. He was great.

Rest in peace, Ezra.

Definitely.

Going back to Luke - Puppet is open source. He wants you to pay him.

He did. Yeah. Which was fine. I wasn’t upset that he wanted to get paid. I was upset at – there’s this severity one awful thing –

[00:54:20.10] The severity, yeah.

…and his answer was basically “You must pay me or I won’t fix it”, and I was just “I can’t even with that. Why wouldn’t you see that this is a thing you must fix? It’s obviously terrible for your product.”

That’s the part I want to dig into, the whole “You must fix.” Because I’m sure you know open source works, Adam. I’m talking to the person I go to for answers when I’ve got deep philosophical questions about open source, and the way it merges with our freedoms in it…

Yeah.

He’s free to not fix it, right?

He’s 100% free to not fix it.

But you’re like “Dude, come on. It’s so bad you should”, right?

Yes.

You used the word “must”, is what I’m trying to dig into.

Because product-wise, you must. What Luke wanted most – and we’d spent time together. I knew. Luke wanted the ring. Luke wanted it all. That was what he wanted. And so this was a terrible business decision. And so the argument I was having with him wasn’t demanding his time for free. I was like “Homie, do you not see that this is phenomenally bad for you? When you think about just people adopting the software, using it, trusting it…” Puppet was on the rise… And here’s this lurking time-bomb –

It was the thing to use. Right?

It was absolutely the thing to use. And it was great. And here’s this time bomb, sitting in the middle of your product, and like, that’s not the thing? And I just didn’t understand it. And for me, it’s not that I demanded he fix it, because I was willing to fix it myself… I wasn’t upset that he told me to fix it myself.

Okay. That’s what I wanted clarity on, because I was like “Man…”

Fixing it myself was a fine answer. Him being like “Look, I’m too busy. I’ve got stuff happening, I’ve got to feed my kids…” I’m like “Great. Feed your kids. I’m willing to do it.” But he was mad I fixed it. That’s how it felt to me. I’m sure if we get him on the podcast, he’ll be like “No, I wasn’t. You big jerk.” But it sure felt that way to me, and to a bunch of other people that were there at the time. And to be fair to Luke, I’m sure there’s a different side of this story that if he told it, it would be very different… But –

For sure, because there’s perspectives.

Yeah, there’s perspectives. Luke’s not a bad guy. Whatever. We’re not besties, but I don’t hate Luke. I’m not carrying around a weird grudge or whatever. But yeah, it was more those pieces that I couldn’t understand. And then for me, building my business – and I was out stumping. I was going to conferences, giving Puppet talks… I was telling people this was the way and teaching them how to do it, because it was raising my own profile at the same time, and his. And I was like “I can’t do it if what I’m leading all those people into is a trap, in this way.”

The inevitable resolve conf file getting overwritten with a checksum. That’s just –

Right? That’s bad news. It was tough.

That you couldn’t even personally reproduce…

No. It happens at random… Yeah, it was bad. So it wasn’t that I demanded that he do the work. “Must” was “Clearly, you must fix it for your survival, for your own best interest. And for mine, because I’m trying to build a business on top of your software, and I can’t do it.” And he was kind of annoyed I was doing that too, because again, if I wasn’t doing it, maybe they would have called Luke, you know?

And then we raised venture capital, I think before Luke did, which I think annoyed him, too… And certainly the existence of Chef annoyed him, because it felt like we had stolen from him… We didn’t. But you know, that’s how it felt at the time.

Did you begin from first principles? I know you didn’t steal any code, obviously, but did you did you borrow any – I mean, because open source is… It’s art. And art imitates other art. There’s borrowing that happened. There’s influences that happened, obviously.

[00:57:50.29] A hundred percent. Look, it was a hundred percent influenced by Puppet. There’s a bunch of things that Luke invented. The declarative resource abstraction, that idea that you would just say “This is the file, and here’s the shape that I want it in”, and then here’s a package, and I want that in this condition… There’d be no Kubernetes [unintelligible 00:58:07.19] was the person that created that abstraction that says “Here’s how I want to declare this resource”, and then that resource maps to something real in the world, and then there’s a reconciliation loop that solves those things, and you laid them out in the way you did… That was all Luke. And Mark Burgess had invented much of the structure that drove those systems. So a lot of the fundamental underpinnings, that was Mark. But Luke was the one who put that user experience on top of it, that gave you that abstraction. And you’ve got to praise the man for it. If he hadn’t done that, we would we be on a fundamentally different trajectory. And [unintelligible 00:58:43.27] is a genius. He’s brilliant. And if it hadn’t been for Luke, Chef wouldn’t have looked that at all. Because I wouldn’t have come to that conclusion. But I had his prior art, and then I fixed the things that I thought were wrong with it. The way the graph worked, I wanted it to be a real programming language, not a DSL… On and on and on. And it was a fundamentally different product because of it. But it doesn’t mean that I wasn’t standing on his shoulders. If there wasn’t for Chef, there’d be no Pulumi. Right? There’d be no CDK. Those ideas of “You should do the automation in a real programming language…” Chef was the first of those, really, that wasn’t just writing scripts, you know? But it all stands on each other.

For sure. Yeah, it’s interesting just how that plays out, that you can be a part of that… And I think one thing you said was that you were using Puppet in ways it was not – I’m trying to paraphrase, to some degree. You said in ways beyond it was planned to be used… You were hitting the edge cases…

I mean, not planned. We were using it more than most people. So most people were using a little Puppet in their stable compute lab. And we were using Puppet to be like “No, I’m writing reusable content that I deploy really quickly across… And it’s thousands of resources. I’m fully managing every aspect of the system with Puppet.” Most people weren’t. They were like – they were replacing CFEngine 2, which was setting up a config file, and making sure that the patch ran… There was a half dozen resources they were managing. If you were managing a hundred resources on a single box, that was a big deal. Our standard config on a single host was 300+, 400. So when you think about that in aggregate, it was just – and the sizes were so much bigger. Because at the time - this was the beginning of Web 2. So this was Facebook apps, so people couldn’t get enough stuff, couldn’t get enough gear… We had a customer I liked, who was one of the first music sharing things. It was a Facebook app, and so they had a billion users immediately. That was unheard of. That was not a thing you could do on the internet before that moment. And it brought social media into the world. And so they literally were calling all of our friends, being like “Do you have any gear? We just want to buy whatever you’ve got. We don’t care what it is. We’ll take it. We’ll put it in racks.” They couldn’t scale fast enough. And so they were using our kit to scale. That automation is what allowed them to do it, which was awesome. And their own intelligence. I’m not saying we did it. [unintelligible 01:01:12.29]

For sure. It was all Chef.

It wasn’t Chef. That was Puppet. That was all Puppet. We were using Puppet to do that. And big deal, right? It was a pretty fun, interesting era.

So if my notes are correct, this beginning of OpsCode - not Chef - was in 2008, roughly.

Yeah, that’s probably right. Ish.

So let’s say maybe 2007, but it happened in kind of 2008.

Yeah. HJK had been going for a couple of years. So you can backdate that to…

Right. Did you literally – I mean, this is probably boring minutiae to some degree, but did you literally convert the company, HJK, to a different company called OpsCode? Or did you just end the consultancy and founded a new company?

[01:01:56.13] We started a new company, and then that company acquired our –

Assets.

Our assets. Yeah.

And you didn’t have to do any due diligence because you knew what was tehre, right?

Yeah, we knew what the diligence was. Yeah, this introduced me to a bunch of new, interesting ideas. So one was that you could – and Jesse knew these things. Jesse had been studying the business of venture capital in a way that I hadn’t. I had been, but I was uncertain still, and Jesse was not uncertain. And so I learned that you should never pay a startup lawyer. That they take their money when you get funded, but they’ll do all the work for you for free, for example. I was like “That’s amazing.” And then he had lots of – he had helped start what would become Velocity, with Tim O’Reilly… And so he was sort of connected to that whole scene, which eventually became sort of the epicenter of how Web 2.0 evolved, and how that entire generation of cloud and all that stuff sort of happened. Those people were connected for the first time sort of through O’Reilly. And so those connections and the technology and the shape of the market at the time allowed us to sort of successfully raise capital. But we had a hard time raising. I think we pitched – Jesse would know the exact number, but like 15, 20 times, and got no’s… And we were all beaten down, and sort of convinced it wasn’t going to work. And we met Bill Bryant at a coffee shop in Seattle, which was near his house. He held court at this coffee shop. And we gave him our sad, dejected pitch… Because everybody told us to raise less money, basically. And so we had started out asking for two and a half, and we had gotten all the way down to “Please give us half a million dollars. We promise it’ll work out.” And he was like “Guys, this is a sad pitch. Is there a business you believe in hiding in here? Is there a way that we all get a billion dollars? Because if so, I want to hear that pitch.” And we were like “Well, f*** yeah.” And so then we gave him the billion-dollar version, and he was like “That’s a good pitch. That’s what we’re going to do.” And he’s like “And you’re going to ask for three. Ask me for three.” And we were like “Okay, three.” And he was like “Great!”

“No!” “Yes!”

Yeah, exactly. He was like “No, but I’ll give you two and a half in [unintelligible 01:04:06.22] you know? And that worked. You just did it until it worked.

Wow. So two and a half mil. That was your initial funding. Is that right?

I think so. Probably. Or three.

Okay. Did you have a product?

Yeah. But we hadn’t launched it yet. So we announced the fundraising, and we launched Chef at the same time.

Did you launch Chef as open source then, from the beginning?

Yup. And we published the fundraising announcement, a blog post on what Chef was, a blog post about why we chose the Apache license… We had Ezra write a blog post on his blog about it…

On Engine Yard, or personal?

His personal. But we referenced Engine Yard, because they were already using Chef.

And so you’d already done all that automation for Engine Yard prior to even this pitch and fundraise?

Yeah, yeah, yeah.

Okay. So you knew, you had faith in what the software was able to do in its infancy.

Yeah. And it wasn’t a great launch, you know? Our color scheme was gray and blue, and it was a website built by systems administrators, lots of squares…

Sure.

But what did happen was there was very quickly a community of people who we knew from Puppet and we knew from the Rails community, who really attached quickly to Chef. And then we knew that we were building a community, and it was all open source, and so we just embraced everyone who would listen. And at that time open source still happened on IRC primarily… And you can see it now happening again, and kind of in Discord, where I would argue open source now happens mostly, in Discord, if there’s an analog… And so we just wound up hanging out with everybody who cared about what we did. And because we came up as consultants, we frequently knew how to automate whatever they were trying to automate better than they did… And so we would help people not only use the software, but solve their root problem in a deeper way.

[01:06:06.28] So one of the things I used to do at the end of my conference talks every now and again was I would just – I would ask people how many people use Chef, and how people use Puppet, and how many people use CFEngine, and I would offer to fix their problems, not by converting them to Chef, but just like, I knew CFEngine really well, and I knew Puppet really well, and so you could come to me with your Puppet problem and I would fix your Puppet problem, you know?

And so we just really intentionally tried to build a community. Because at the time - you know, this was Tim O’Reilly’s “Create more value than you capture.” All of that was sort of both in our minds and in our culture, and was starting to really crystallize around Velocity, and around the Web 2.0 Summit, and around a couple of those conferences. And so that idea really captured us, and it really was embedded in that business plan. And I think we did a good job.

Yeah, very interesting. Those initial days… You know, you’re obviously deeply in community, out there giving talks, willing to fix non-Chef things, as you just said…

Yeah, just doing whatever.

What was the thing that people were buying? What was the paid for version of Chef?

Yeah, so initially it was going to be a hosted SaaS. So this was also the moment – the rise of SaaS. So Salesforce had launched a few years earlier, AWS had just begun, so like S3 was just happening… EC2 had just happened… And so like SaaS was just beginning. And so our idea was that we were going to run a hosted service, and then if you wanted to run it on-prem - which you’d be a dummy to do - you would be open source. And we were just way too early for hosted configuration management. Like, way too early, you know?

And so yeah, we launched this hosted SaaS product, big multi-tenant SaaS service, that did okay, but didn’t do great. And all of the large customers, banks and insurance companies and stuff would just run the open source, because they weren’t willing to run a hosted product. A decade later, they would all come to me and be like “Can I just buy a SaaS?” And I was like “F**k you guys.”

Like “You’re ten years too late.”

“I did this for you, and now I have let it flounder because you didn’t care.” But yeah, so that was the original business model, was SaaS.

Wow.

And then over time it turned more and more toward on-prem software, feature discrimination… All of that stuff sort of crept in, because we were trying to figure out how to monetize what was a growing enterprise user base, and just trying to figure it out… And we really struggled to do it, as I’ve talked about sort of at length, I think.

I’ve never heard the story.

Yeah, I mean, we’ve gone through – we went through every possible open source business model. We started out SaaS plus open source that you could run on-prem… We had the open source version, and then we took the SaaS version, and we sold that as an enterprise version. It was like “Hey, if you want these other features–” We wrote the backend in Erlang, which was one of the greatest technological things I’ve ever seen in my life. The team rewrote the Chef server in Erlang because we had Facebook as a customer, and their goal was to bootstrap a data center… And I remember what the time goal was, but it was like five minutes, 10 minutes, from scratch…

What?

Yeah, it was nuts, right? And it was really condensed. And the Ruby-based Chef server just couldn’t do it, and I remember going to Facebook with the Erlang Chef server on a USB key that had a little – whatever, it was like a little bear’s head on the end of it. And I brought it to Facebook, and we installed it and ran it, and we thought that it didn’t work at all, because the load was flat, and there was no utilization, and then everything finished and it was fine. So the Erlang just literally ate all the load and just didn’t care [unintelligible 01:09:43.18] It was incredible. The first time that we’d used it outside the lab, it was truly incredible.

So we were like “Hey, if you want the good one, pay us for the good one.” And then it becomes hard to maintain both, so then you’re like “Well, maybe we should just open-source the good one too, but then we’ll hold back some features. Maybe it’ll be security features.” Then maybe it’ll be – well, and then what we actually should do is… Like, you can’t hold back basic security. That makes you kind of a jerk. So maybe we’ll build like a dashboard, a better web UI, we’ll monetize that… Maybe it’s security and compliance, we’ll do that, we made some acquisitions, brought in the [unintelligible 01:10:19.12] folks… That was great. They were awesome. Their code was incredible. They helped. We tried every variation of open core possible, and then in the end switched to a model that looked like Red Hat’s, which was the most efficient by a dramatic margin.

[01:10:37.04] Would you say those 10 years before acquisition was a struggle to find the business model then? Like, given this, in hindsight?

I mean, yes and no…

Because the thing was good. It was hard to make money off of it, right?

We should have made more money than we did.

Right.

So if we had made the amount of money for the value we created, that company would still exist. It’d be a public company and you’d be talking about it now. We didn’t, and so it wasn’t. But it wasn’t because we didn’t have an impact. The impact we had on the enterprise, the client list we had… We were still growing at a reasonable clip, but… Yeah, I would say – a lot of people tell successful startup stories and they always draw like a smooth line, sort of up and to the right… That was not my experience. My experience was that it was a series of stair steps, where all the flat spots in the stairs were just terrifying and existential… And you didn’t have enough life experience or business experience to tell the difference.

So there’s a lot of things that in hindsight weren’t existential, that we thought were, and freaked out about… And then there’s a lot of things that really were existential, that we freaked out about justifiably, and then fixed, and then the business model worked out. But I wouldn’t say it was easy, and a lot of it wasn’t so much – it was never the technology, it’s always people, you know? It’s hard to find the right people, it’s hard to work with people, it’s hard to figure out how to build a culture, it’s hard to keep that culture… Yeah, it was hard. At the same time, we were quite successful and it was really fun, and I have no regrets. I would do it roughly – I wouldn’t do it the same way; I’d have changed the business model if I had hindsight. But I think what that did for me was professionalize me.

So there was a moment in Chef’s life where - you know, Docker had happened, and Docker was so disruptive to us and to everyone in that space… And there was a minute where they were just – you couldn’t have a conversation that wasn’t just Docker, Docker, Docker, Docker, Docker, Docker, Docker. And with our own investors, our customers, they were like “You guys are dead, right?” It was awful.

What year was that?

I don’t remember, because I’m bad at time. But early on in Docker’s life. So a year into Docker’s existence, probably.

2015, 2016, maybe?

Yeah, maybe. And I had to give a speech to – because the company was really down. And so Barry Christ asked me to give them a pep talk, you know? And so I went and watched – Al Pacino did a football movie, whose name escapes me… It’s Any Given Sunday.

Oh, yes. Yes. Any Given Sunday.

At the end of Any Given Sunday, he gives the greatest inspirational speech ever put to film. He’s basically got this bunch of football players, and he’s like “Life is a game of inches, and you’ve got to crawl for it, and you’ve got to look at the people next to you…!” And he gives this incredible speech about basically how the team needs to pull together, and that the struggle is living. That pushing through it is the source of what it means to be alive. And so I studied him delivering this speech, because that’s how I wanted to deliver it… And I wrote my speech, and I did my best to deliver it like I was coaching a football team, like I was Al Pacino. And it worked. I think it did actually rally the team; it rallied the company. But as soon as I was done giving this speech - I’m so grateful that I was alone. So we had this office in San Francisco, that wasn’t full of very many people… And it had a beanbag, because whatever, startups… And I just collapsed and wept for like half an hour. Full body, just weeping. Because the stress of trying to hold it all together, and not knowing – you know, I just told all these people what to do… But what if they didn’t? What if we lost? What would that say about me? What would it say about them? What would happen to their lives? What would happen to mine, my family?

[01:14:29.22] And all of that pressure and all of that was so intense, and I just couldn’t hold it in anymore. And I realized that the problem was that this had become my life, and not my job. And that it was – there’s a part of it being your life that’s helpful, when you’re trying to do something new… You hear musicians talk about this all the time, where they didn’t have a plan B… That’s good, and can be helpful. But eventually, it turns out that it’s your job, and that I don’t control the outcomes. I don’t control what people do. I don’t control whether it’s gonna work. What I do control is how I act.

I control what we do next, I control how we respond… And to do that well, I needed to put down the burden that said that it was my responsibility. And instead, my responsibility was to just be the best I could possibly be at the work that I had to do. Then it had to become about the work I was doing, not about whether or not it was gonna happen for all of these people. And that really transformed who I am into a person like now, what I am as a professional CEO, I’m a professional entrepreneur… I do that, it’s my job, but it’s not who I am. And that’s the moment that it stopped being who I am.

It’s interesting that your identity is wrapped up in that. Because when you say “That’s who I was, it’s what I was”, that’s what you mean, right? Your identity was deeply ingrained, tied to, tethered to…

And your self-worth.

Yeah. Who you are as Adam Jacob. Your worth is “Oh, is Chef successful? No? Okay. Well, you suck.”

Then you do suck, you know? I had people tap me on a shoulder in a coffee shop and be like “You’re Adam Jacob, you wrote Chef?” And I’m like “Yeah.” And he’s like “Oh, I f*****g hate Chef”, you know?

Dang, man…

Just a random stranger, felt entitled enough… And I was like “I’m sorry, I wasn’t thinking about you when I wrote it. I didn’t mean to hurt you.” But I have way more people tell me that it changed their lives, and how it impacted their careers, and their families… And I have a million lovely stories of that. But yeah, it does sort of – at some point you have to decide what fuel you’re gonna burn… Because you’re on this long journey, it takes 15 years… And if the fuel you decide to burn is your own self-worth, your own belief in yourself, you’ll run out eventually. There’ll be enough things that tell you that it’s not real, that that’ll be it for you. And so I just needed to switch fuel, you know? That’s not because I don’t have some of my identity wrapped up in those things, I do. It’s been – I’m 46, and as we’ve just talked about, I’ve been doing it since I was a kid. That is a huge part of who I am. But it’s not all of who I am. And my success or failure doesn’t define who I am, you know? I’m gonna be good at it, whether I win or lose. I’m great at it, because I’m putting in the work to be good at it. And that puts me in a position, hopefully, to succeed… But you know, just like those football players at the end of Any Given Sunday, the other team’s feeling the same way, you know? Everybody else also in that game is trying to do the same thing. They’re trying to win, too. And you win or lose, and sometimes it’s your time, and sometimes it’s not your time. And you can’t control it. But if you’re burning self-worth, if you lose, and what you burned down is your identity, your self-worth, your belief in yourself, it’s tough to get back up again, you know? It’s hard to decide to keep going. But if it’s professional acumen, if it’s skill, then it’s just “Now I’m a pro. Now it’s the game I play, and I’m doing my best to play it well.”

[01:18:08.14] In the military - I was in the army for a bit in my life, and when we did things that didn’t seem like it made sense, or it seemed like rework, or it didn’t have meaning, or it had meaning, it was just too big, the response was never negative.

It was always “Good training. That was good training.” Because you do some things sometimes in life and you’re like “That sucked. What purpose did it have?” It was good training.

It was good training.

It wasn’t “Burn Adam down”, whether I’m talking to you or me, because we’re both named Adam… It was simply, “Wow, I went through that to learn something, and it was good training.”

Yeah, it just – it was good training.

Don’t let it be self-worth burning.

No. Because it can’t be.

Yeah. Or team burning. Like “That sucked for us.” Like, we suck as a team because we just went through this thing.

Right. Does that make us a bad team? I’m so grateful for those moments, and I’m so grateful for the opportunity to have had them… And yeah, but I wouldn’t still be doing it if I hadn’t had that revelation, that this is just about the work, and that the answer is always just more work. So it doesn’t matter what the problem is, I’m a professional. My job is to do the work. And I’m going to do the work at the highest level I can do it, because that’s what I have pride in. Because I can control that. I can control how I put in the work, I can control the level that I’m playing at… And that doesn’t mean I’m always playing at the best I can play. Sometimes I have bad days. Everybody does. But that’s a thing that I can do. And in the sense of good training, even if I fail, it’s good training. I’ll be better. I’m going to learn from it all. My game will get better. I’ll be able to figure out how to motivate it. Yeah.

Not to go too deep into this scenario for you, but when you gave this speech, and you said you were “trying to hold it together”, you must have been terrified in that moment, to give that speech. Were you trying to – I mean, without giving away what the details specifically were, were you trying to hype and sell this potential future? What were you trying to accomplish?

No… I was trying to remind them who they were. Like, we had built this incredible company, we’d built this incredible community… We were having an incredible impact on those enterprises. And I would – look, for as much impact as Docker has had, and it has had an incredible impact, I know what Chef did at some of those companies. I know what they were like before, and I know what they were like after. And the impact Chef had on those people’s careers, on their lives, on how they structure their company, on what they do - we did that. And this was the people who did it. And I was trying to remind them who they were. And I was trying to remind them that it didn’t matter what the outside world said. It didn’t matter what new technology people were hyped up about. It didn’t matter what any of those things were. What mattered was what we could do for those customers. What we could do for those people. That we were the people who could do that, and we were better. And we would stay better, because we were great at it. But if we didn’t lose faith in each other, and we remembered who we were, that we were going to get through it. And we did. When we sold Chef – we had tried to sell it years before… There was a moment where nobody would buy it for a dollar. And this is a company with tens of millions of dollars in revenue, recurring, growing 20% year over year… Like, it’s great. Not one f***ing dollar, because the market had just turned away from you, and was convinced you were going to die. And it didn’t. We didn’t. We figured out how to land that plane. And I’m so proud of it. But that was because those people didn’t lose faith in each other. You know? And that’s what I was trying to do. I was just trying to remind them of who they were, and what they had done, and what they could still do.

I guess in a way you’re probably giving this speech to yourself too, which is why you went away and did what you did, because it landed on your own – like, sometimes you come up with the idea, and then you say it out loud, and then it becomes… Like, it was real beforehand, and it was still true beforehand. But you said it –

[01:22:14.17] Yeah, yeah. And thinking about it now, and talking to you about it - like, I’m welling up now just thinking about it. I don’t think I’m going to cry, but I might. If I do, great podcast material. But yeah, of course I was giving it to myself.

Of course I was. And look, in the years since, I’ve been in therapy, and learned a lot, and I’m improving… But it’s not easy for me to talk about, like most people… There’s some people for whom they can talk about how they’re feeling, and it’s like very difficult for me to talk about how I feel. If you ask me what’s happening, I’m gregarious enough, I’ll tell you how my day was, I’ll tell you like a list of facts about my day… But I’m not going to lead with how I feel at the end of the day. I’m not going to be like “Oh, I feel anxious. I feel stressed. I feel sad. I feel whatever.” And so it’s not like I was expressing to other people, anyone else, even including my wife, what the burden I was holding was. That was all just inside, and I was just white-knuckling it sort of through all of those moments. And yeah, so there was a lot of internal pressure that had sort of built up there that needed release. I think part of why the speech was good was because that same energy came out in the speech. I used that as fuel. And because I had allowed that to happen when I gave the speech, suddenly all these emotions I had not been processing and hadn’t been holding onto I couldn’t keep in anymore. And even though I couldn’t verbalize them, I could certainly experience them physically by just weeping, sobbing, you know?

Yeah. Well, thank you for sharing that. I know that’s vulnerable to put that kind of stuff out there, and to share that… But I think that’s – it’s a beautiful thing, because we live in this world where it’s a one or a zero. It’s on or it’s off. And especially in the developer world, things are very binary in the fact that it’s true or not true. It’s an error or it’s not, it runs or it doesn’t, whatever. And then you kind of get into this other zone where it’s like, well, there’s people involved, and there’s emotions involved, and there’s identities involved and there’s promises made, and there’s self-worth that’s established in something erroneously or not… And there’s a lot of detail in there that I think is very telling of your character.

Well, thank you.

And just telling of your willingness to share the journey.

Yeah. I mean, because of that experience in open source and all the people who have helped me – you know, if I hadn’t met Jesse Robbins and he hadn’t believed in Chef, and hadn’t believed in me, and hadn’t believed in those things, there wouldn’t have been an Ops Code. And if there hadn’t been an Ops Code, there wouldn’t be a System Initiative, and there wouldn’t have been a Chef. There’s so many things that would have not happened, or would have happened differently.

And I think you have a responsibility at some point, when you reach a certain level of professionalism, to help other people climb that same pyramid. If it wasn’t for Ezra, where would I be, you know? And Ezra was higher on that pyramid than I was. And in that moment, he didn’t have to help me, but he chose to help me. And in that moment that he helped me, he lifted me up, and put me on his shoulders, and helped me become the person that I am. And I think we have a responsibility to do that. And I think people who don’t feel that responsibility, or who don’t do it, or who actively close that door… To be honest, I think they play the game less good. I think in the end, it comes back around. And I think a lot about – I don’t think a lot about it. Well, that’s not true… I have this tattoo, so I do think a lot about it.

[01:25:52.24] What’s the tattoo say?

It’s just three lines that reminds me that I have things that matter in my life, and that they’re not all equal. There’s some things I care about more than others, and I should focus on the things that matter the most. So like my family.

And it’s like in the shape of – it’s kind of a rounded off, sort of like… So three parallel lines that are like ruled paper. Literally, it’s college ruled paper with a Denny’s coffee mug, and we drew a circle around it, and we filled in the lines, and then we tattooed it on my arm. But it’s there to remind me that I have things I value, and that I need to keep those things in my mind while I live my life. And I think that when you think about your life, and you think about the work that you do, or you think about all the things that you’ve done, there’s things that I’ll do that will matter when I’m gone. I hope somebody, on some podcast, someday, is like “Man, Adam Jacob really did blah, blah, blah, blah, and helped me in this way.” And they can be like “Rest in peace, Adam. Pouring out for our homie.” And I hope that that day is far away, and…

Dang, man…

I don’t want that to be now, thank you… But I care more about that than I do about winning. I care about how I win, because I really believe that you can win better by doing it that way. You can win by being good, and by being a person who cares, and being a person who helps other people.

There’s a company that I talked to not that long ago, just getting started, absolutely gonna wind up competitive to System Initiative; started by a bunch of very credible people, who I helped them get funded because I introduced another person who should fund them. I was like “Here’s the person that should fund you.” And that’s the person who’s going to fund them, and he’s a great venture capitalist… And I hope they have all the success in the world. Because it’s not a zero-sum game. If we wind up competing, and we play against each other, I’m gonna beat them. Because I’m better than they are. And I’m gonna fight like hell to do it. But if they beat me, so be it. Some days you win, some days you lose. But let’s f*****g go.

Yeah, for sure. As I’m hearing your story, obviously a lot of tech founders run parallel to some degree to the storyline of Silicon Valley, the TV show. Did you watch that?

Yeah, I watched most of it.

End to end?

I don’t think I watched it all the way to the end. Same thing, a little too close to home. I can’t watch the… I really struggled to watch all the dramatizations of crazy founders who do fraud. I can’t watch the Elizabeth Holmes documentaries.

Well, there’s no fraud in this one. Well, there’s a little bit of blurred lines, but no fraud.

I know. But I have this deep part of me… I was playing Mass Effect last night, the first one, and I decided I was gonna try and be a mean person. And I literally couldn’t make mean person choices.

I feel ya. That’s how I am.

I just couldn’t do it.

I can’t make mean person choices either. I really can’t.

So when I watch those things, and I think about myself and the part of my job that requires me to go out and sell, I’m like “Ooh, am I a fraud? Did I lie?” And it keeps me up at night. And I didn’t, and I’m not. And also, it gives me anxiety. So I stopped watching Silicon Valley, because it was too much. I was like “Nope, that’s too much of my life”, and whatever. It had a Chef cameo. There’s an episode where they talk about Chef. The Chef guy comes in, you know? And I was like “I can’t with this show. It’s too much.” Anyway, keep going. Silicon Valley.

Well, the reason why I ask is because there was a scene where Richard Hendricks - which was the main character you’re familiar with, because you watched season one at least - was juxtaposed against Gavin Bellson, pretty much the entire thing. Gavin Bellson was the villain… He was the one that was doing the fraud, and he was the one that was blurring the lines, and treating people like disposable objects… Whereas Richard Hendricks was trying to do his best, and in a lot of cases be what you just said, which was “How can we win and be good? We can’t all be Hooli.” And there was a point in the show where they were side by side, and Richard was telling Gavin no, and Gavin was like “I shall look forward to the fight.”

[01:30:07.12]

“Welcome home, and congratulations on getting your business back.”

“Thank you. And I should congratulate you on your remarkable tech breakthrough. I hear you’re swimming in funding offers.”

“A few. I think we’re going to go with Supreme Hall. They seem to get us.”

“You haven’t seen all the offers yet. Richard, we were partners once. I’d like to do it again. This is an acquisition offer, and it will make you a very wealthy man. Let’s do this together.”

“That’s very kind of you. But…”

“Richard, at least look it over. I can help you get exactly where you want to go.”

“I’m pretty sure I know where I want to go, and how to get there.”

“If you reject me now, Richard, I will come after you. I’ll devour you. Think very carefully about what you’re doing here.”

“Here’s what I think, Gavin. I think my decentralized internet threatens Hooli’s box business model. I think basically you are just a server company now, and we intend to make servers obsolete. So I think perhaps in the end I will be the one devouring you.”

“I gave you that patent.”

“Thanks.”

“Fair enough, Richard. I shall look forward to the fight.”

And it’s almost like what you said there. While it’s not the same scenario, I like the idea that in business you can lift others up, and invite in some ways competition, hopefully not at your demise, but that you can hold this stance of “I shall look forward to the fight.”

Yeah. If you’re winning, you’re gonna have better competition. A sign of winning is competition. Puppet was winning, therefore Chef existed. Yeah?

Yeah.

And one way to look at it was I was taking away from the potential of Puppet. Another way to look at it was I validated Puppet. I validated that market. We grew together. We did that together. And yeah, all the competitive juices - I really think that’s how you need to look at it, if you’re a professional about it. If it’s about your identity, different thing. If you’re like “Oh, will I make a bunch of money? Will I be able to feed my family?” If it’s those things you’re worried about, different problem. It’s different when you’re worried about whether your kids are gonna go to college, and the competitor – it hits harder. But I’m not in that position and haven’t been in that position for a while. And so now I’m at a point in my life where – yeah, when I think about that competition, I’m like “Yeah, come validate this market. Come be competition. And I’ll like you. I’ll help you up the ladder. And I’m still gonna beat you. I’m still gonna look you in the eye across the metaphorical court, and I’m gonna be the best player I can be. And I’ve been training hard, you know?” [laughs]

Yeah. Literally training hard.

Yeah. So let’s figure it out. Let’s go. I want that. I want there to be competition, I want it to be difficult in that way. I wanna win, but not because – I don’t wanna win because I murdered everyone I see.

That’s no fun.

I mean, there’s certainly no one left to hang out with at the end… And certainly they’re the people who are most likely to be able to talk to you about how it is. Like, they’re the ones you can most talk to about “Oh, that’s awful. I’m so sorry that happened to you. I know what that feels like.” They’re also your peers. They’re the only other people who know what it’s like. So when you think about destroying that pool of people… Like, of course I wanna help people up in that way, because I need those people. Someday I’m gonna need them. I’m gonna need to call them up and be like “I had to do this hard thing…” And they’ll be like “Oh, yeah, I understand.” They’ll be there for you in a way that they won’t, obviously, if what you did was punch them.

[01:34:04.21] Yeah. Don’t punch people.

Not if you can help it.

Yeah. Unless you’re in a mosh pit.

Sometimes you’ve gotta.

Fair game.

Yeah, I mean, probably not, right? You’re kind of a jerk then too, but…

Yeah, I suppose… Well, it’s at least accepted if you get it.

I explained to my daughter that every now and again, sometimes you have to punch someone.

Okay.

And you want it to be rare, you know? Like, you want it to not be a thing you do regularly or easily. But if you’re gonna have to punch someone, you’d prefer to be the one who punches first, than second.

Break: [01:34:32.02]

What is it that matters to you, Adam? I know what you’re doing now. Let’s fast-forward a little tiny bit, and I’ll do the job for you. Eventually, you sell Chef. I’d love to get into the details of that. I know you kind of stepped away in a way, I don’t know the full story; I’d love it from the horse’s mouth, obviously. You’ve obviously taken a – I’m not sure if you’d call it a break between Chef and System Initiative. I’m not really sure of the timeline between there… But you’re on a journey still yet to revolutionize and potentially change the future of DevOps. And so you haven’t stopped this journey, but given that fast-forward of a lens in a way - and I’m happy to dig into the details - in life, what really matters to you? What matters to you?

The people that I love, and the life that we can create together. I care about my family, and I care about how my family goes forward in the world, and what their lives are like. That’s the thing that matters to me. I know that’s cliché, but it’s true. And then I care about how I spend my time. You have a limited amount of it, and so I need work that is compelling, I need to care, I need to believe that the art of it is worth doing, because I want to play that game because it’s the funnest game I’ve ever played. It’s the game I’ve been playing since I was eight, and it’s still the game I love the most, you know? So I kind of feel like it’s one unbroken line of training, from running a bulletin board to now. And it’s just one unbroken experience of like training to do this kind of thing.

And so yeah, we sold Chef, I had stepped away very slowly… I basically left – I knew I was leaving, and had told Barry Crist, who’s fantastic, the CEO of Chef, that I was going to leave. And then I basically took a year to do it, by just sort of–

You were CTO? Is that what your title was?

Yeah, I was CTO. And we searched for my replacement, and then I slowly backed away from all of the work I was doing… But I didn’t tell anyone I was backing away. I just kind of stopped showing up, and let other people take care of it. And they all just figured I was really busy. Because I was usually really busy. But in this case, I wasn’t actually really busy, they just all thought I was busy with someone else… And so by the time I actually left, it had been six months since anybody had needed me to make a single decision, because I had just sort of made myself disappear slowly. And then we hired my replacement, and he was fantastic, and we had a great relationship, and I helped him move in. I’m really proud of how I left Chef. I stayed on the board, so I was involved in the transaction… I can’t go into too many details about that. But then - yeah, I took some time off, and then… You know, with System Initiative, back to what motivates me as a person - this is how I’m looping you back into that answer. Like, in my work, outside of my personal life and the people I love - those are my atomic family, but also my chosen family. I have a lot of people that feel like chosen family to me, where I’m in it for life with them, and I don’t care what they do, I don’t care what happens, those are my people, and they’re going to be my people no matter what. And that doesn’t mean I won’t tell them if I think they do something wrong… But I’m telling them because I love them, not because I’m not going to stop loving you. Love is unconditional. And I have a lot of those people in my life, and I care deeply about them.

In my work, now that I know that I’m a professional and that I’m quite good at it, I want to build the best possible thing I can imagine. Because I really think that we can not only build technology that is foundationally earth-shattering, but we can do it in a way that the people who built it are having the best experience they can have. I really think about the foundational work of building System Initiative like building a sports team. I’m finding great talent, I’m nurturing that talent, I’m challenging them, I’m training them, I’m putting them together… And that is inspiring to me, to put it against a problem that’s really complicated and hard.

And so what we decided to do with System Initiative was rethink the foundational abstractions of how we think about automation. So throw away as much of the prior art as we needed to, to see what would happen if we went a different way. And it’s been roughly five years of engineering and R&D. We’re going to launch a public SaaS here, let’s call it fall… And if you want to try it now, you can. So slide into my DMs and I’ll like hook you up. And it is a transformatively different point of view on how to build that automation. And it’s a transformatively different user experience. And it’s been incredibly difficult to build, but it’s so rewarding. Because then when it works, you’re like “Oh, that feels like magic.

That is new in a fundamental way.”

[01:43:55.24] And so I love the newness of it, I love the art of it… And it’s starting to turn over like a business, and I love that too, because you get – there’s nothing more validating in some ways than winning through revenue. When somebody is willing to pay you for it, that’s that’s good juice. So that is also motivating to me. Yeah.

Okay. So let’s laser into the thing at play currently. We’ve talked about the past, we’ve cliff-noted the exit… I don’t think there’s necessarily anything to dig into there. I think it’s good to be proud of how you exit something, because - you know, don’t burn bridges. Be a great person. Be the person you want to be, obviously…

Yeah, it’s a hard thing to decide… If your exit isn’t perfect, isn’t magical, then you’re making decisions about how it impacts everyone’s lives in a really meaningful way. So do those early employees get enough money to send a kid to college, but the newer employees will make less? And so maybe there’s an option not to sell it, where there’s an odds that those new employees would make more, but they’d kind of do it at the expense of the old ones? So you have to think about how do you balance all of that out, you know? So it’s like a complicated story, it’s a complicated thing to have to go through, but you can do it with honor, you know? You can look everybody in the eye and talk about the trade-offs you made.

Did you, in fact, get to step away and take some version of what they would call a “break”? Did you get to rest a little bit?

Yeah, I took like six months off, basically.

Did you think about anything at all? Did you just listen to metal all the time and go for walks?

I sat in my office, quote-unquote, which was actually just a bathroom that we had never gotten around to renovating, in this apartment… Not apartment, house in San Francisco. And I played Dark Souls, because I really wanted to learn how to do that… And so I played Dark Souls, I wrote a D&D campaign, ran it for my friends… I walked my daughter to school every day… She was going to elementary school in the Castro, so there was this lovely sunny walk from the Mission through to the Castro. And so I’d walk her to school and pick her up… That was fantastic.

I built a laptop and noodled around with my environment… I played with operating systems, because I love playing with operating systems. So I played with my operating system. And yeah, and thought a little about what I wanted to do next, but mostly I put it all down.

Was that hard to put it down?

No.

It was actually easy.

I was tired. That was a lot. And I had already seen that what we were doing wasn’t going to work long term, so I knew that the returns we were getting from the work we had done for those large enterprises - which was transformative - that the teams we transformed were incredible, but that the drop-off between those teams and the rest of the company was really steep. And that that wasn’t kind of the way we hoped it would go kind of as an industry. And so I had already gotten a little tired of playing myself on TV, where I knew what I needed to do, which is go to those companies and tell them that they should do it anyway, and tell them that it was going to work out, even though I knew in my heart it wasn’t. And I didn’t love that. I didn’t love – as soon as that realization hit me, I couldn’t do it anymore in the same authentic way that I had been doing it, and so I was ready to stop. And I was ready to think about what was next because I felt like the story was undone. It’s not like I was finished with the things that I cared about or helping the people that I cared about; I still loved systems administrators, I loved DevOps, I loved all those things. I wasn’t finished.

But I didn’t believe that if I kept pushing the direction we were going in that way, that it was going to work. And that made sense, you know? So it just made sense to put it down, and I knew that what I would pick up next would be something that would try to move the needle on how those experiences happen for those people.

So you were able to take a break, which is great… You had a good reason to take the break. You’ve got family, you’ve got this beautiful walk with your daughter… I’m sure that’s a memory that in your mental picture you can recall in this very moment, and it’s very pure and very enjoyable. I think there’s something –

You know what I learned about myself the other day?

What did you learn?

[01:47:59.16] So when people talk about the mental picture, they actually see pictures in their head.

You can’t see a picture?

I see nothing.

Oh, dude, I’m sorry about that.

I’m not. I mean –

Oh, you’re missing out.

I believe I probably am. It’s like facts, it’s like lists of… But I know, I remember it, and I do feel fondly about it. It’s not like – I do feel nostalgic for it. But anyway, anyway. I don’t see the picture. Anyway, yes, keep going.

Well, I’m sad for you on that front, because I can various moments in my life – now, my son, he has got… And this is because of my wife. He’s got the literal ability to look at something and see it forever.

Oh.

He’s got that, whatever it’s called, picture memory or whatever.

Photographic memory.

Photographic memory. Thank you. He and my wife both have that. It’s a blessing and a curse, because like sometimes you can’t see the bad things, because you can’t unsee the bad things. But at the same time, if I’m looking – here’s my superpower with my son. Give me a side tangent here, okay?

Yeah, yeah.

We’re at the grocery store, and I’m on the app and I see the product I’m trying to find. And I’ve not bought it before. I’m trying to make marshmallows. I’m looking for, I don’t know, something, an ingredient. We were making homemade marshmallows this past weekend. And so that’s why this is ringing true. And I’m like “Eli, look at this. Here’s the product. Help me find it on the shelf.” Because finding products on shelves in grocery stores that you’ve never bought before - you don’t know if it’s big, or small, or whatever… And thankfully they have apps these days, so H-E-B - I live in Texas - it has a fantastic application that lets you see all the stuff, and place your order, and pick up, and all that good stuff. And I’m like “Here’s the thing. We’re in the right aisle. Where is it at?” He’s like “Oh, right there.”

Amazing.

So anyways.

Sick.

But the point is is that I can see clearly various moments in my life. Like, more recently me and my son’s fishing. I have two sons. And I have a daughter as well, but in this moment it was just the two sons. And so we were fishing. I can clearly remember sitting back, just thinking “Adam, don’t lose this moment. Adam, take a picture of this moment.”

Like, hold this in your mind forever…

Just pause all the stresses that you might have of them falling in the water or getting hooked by the fish… All the dad concerns. Just put them over there, and just take a breath and just calm down. Because I should be calm anyways. Why should I be stressed? We’re fishing. We’re gone fishing.

It’s literally what it’s for.

And I take this mental picture and I can see it in my mind right now. I can see the sun glistening off the water, I can see the stream, where it’s at, and I can see my two sons just like being silly. The most joyful moment ever. I can just see it so clearly.

Yeah. I can’t see any of that, but what I can do - but I know exactly how I felt. So when I hear that, what I translate that to is how it felt in that moment. And I know exactly how it felt to hold my daughter’s hand while I walked her to school every day. I know exactly how it felt when she was born, and I held her for the first – I can’t see the picture, I have the facts of the picture, but I can’t see it in my head, but I can feel it like it was happening right now. So yeah. Anyway, keep going.

Uh, I don’t know where I was going with that, but I’m sad that you don’t have that, because…

I mean, I have the feeling, which I think to me is enough.

It is enough. It is enough. Let me be sad though, that you don’t have what I have, which I think a lot of people do have, is this mental picture.

Yeah, I think it’s normal that people have that, yeah.

There’s a lot of people who don’t have it, and I don’t know what the phenomenon is of people who do and don’t have it, but there definitely is –

I don’t know, my daughter was taking a random test on the internet and she was like “Dad, can you see pictures in your head?” And I’m like “No, that’s metaphor.” She was like “What?!” And I’m like “Every time people say that, it’s just metaphor. They’re just… It’s metaphor.” She’s like “Dad, that’s not metaphor.” [laughter] And I’m like “Oh. Okay…”

“Okay…”

[laughs] Yeah. Anyway.

I would love to go into System Initiative, but not so deeply. I think the major questions I have, and I think we may have asked you loosely in past conversations, but the conversation was less focused on that, was why be in stealth for five years kind of thing? Like, how did you finance the early parts of the business? Some of that startup process.

[01:52:11.05] Yeah. With System Initiative - so we had three founders: me, Mahir Lupinacci and Alex Ethier. And I think one of the reasons we were in stealth for a long time was just that we actually didn’t know what the solution to the problem was. I had some ideas about what it would be, and Alex had some ideas about it, but we didn’t know for sure, and we were trying to discover sort of what the solution was. And we had enough expertise that we raised venture capital kind of immediately, and had enough space to go do that… I think that process of building something, showing it to people, learning what it was… And we did that a lot. So we showed it to people, but we showed it to them privately, and sort of in more testing kind of frames.

Was it valuable to be stealthy? Like, over five years, probably, in that if you tell people how great something is, and then five years later it shows up, they’re like – you kind of missed your shot at like capturing their attention.

Yeah. You built it up a lot, yeah.

System Initiative - we launched it as open source, and you’ve been able to download it and try it and do stuff with it for a while, and people have been… But now it’s kind of in the shape where the fullness of the experience is compressing in a way that you’ll be able to use it, and it feels good, and it’s stable for you, and it can like solve your real problems in a way that it hasn’t been able to do, just because the technology was so complicated.

In terms of funding the business, the only real struggle there is that five years is a freakin’ eternity in startup land. And we felt like we were close for a really long time, because we’ve sort of known what the answer is… But because we had to build all this foundational technology, you just didn’t really know when you were gonna get it wrong, because no one had ever built it that way before, so you’re like “Ah, that won’t work. Ah, that won’t work.” And you just don’t know until you’re right at the end, and then you’re like “Ah, here’s another soul-crushing problem we have to solve.” And so it’s just been like a series of really difficult obstacles.

Luckily, System Initiative is incredibly compelling, and so our ability to keep it funded and to keep our investors sort of happy is pretty great, because what we’re building is transformative and very cool, and so they’re in. That said, it’s gotta get into the world, and people need to use it, and we’ll see if people love it. But I can’t imagine building something cooler… It’s super-cool, and how it works is super-different, and so those things together I think is enough to carry it into the market in the way that it needs to.

And again, as a professional, that’s my job. What I do is I take venture capital money and I try to build the best businesses I can build from it. And one of the ways you build the best business in technology is you have to have foundationally great technology. If you do, you have a better shot at it being transformative and meaningful over a long period of time. So you’ve gotta deliver on that. And so I think we’re delivering on it.

Timing is key, right? Timing is key in any launch.

Yeah, it makes a difference.

Wouldn’t you say?

Timing is key.

I mean, you have a history of the timing with Chef…

Chef had particularly good timing, I think. The market was really ready for it. I think the market’s really ready for stuff like System Initiative 2. I think when you look at market timing and you think about – the question there usually is more about like… It’s difficult to time the market, but it’s easy to time the zeitgeist of the customer. So if you think about like what is the experience everyone’s having, and can you say to them what that experience is in their own words, so that when they hear from you what it is you’re doing, does it resonate with them in their lived experience? That’s a thing you can learn how to do, and you can learn to discover, and you can follow that truth. It can’t tell you what to build. It doesn’t tell you how to solve that problem or solve that experience, but it tells you that it’s real. It tells you that that experience is universal, that that problem is real, that that moment of displeasure or dislike is real, and that’s a place where you can go build a business and exploit it.

[01:56:26.12] So some of it is external market timing. For Chef, that was like the rise of SaaS and hyperscale, which sort of sets the stage for needing ubiquitous automation, because without it you can’t scale quickly enough. But with System Initiative it is those failed DevOps experiences. It is that when you ask people who do that work, if they enjoy it, the answer is “I love the technology, kind of, but it hurts me all the time.” They’re like playing Dark Souls. And it could be better. And they are willing to have it be better, because that lived experience feels that way. And I think that is a market timing that you can create, that in retrospect people will look at and be like “Oh, what great timing.” But in truth, it’s actually just “How close are you to those people?” The further away you are from the people who are going to use your product, the harder it is to build something that they’re going to love.

I guess what I was potentially trying to get is to ruffle your feathers a little bit. Not so much your feathers particularly, but mostly just to consider - with Chef, you battled the rise of Docker and a change in the ecosystem. And we talked about your five years of stealth, and it’s a wonderful thing to be able to have the investors and the folks to be there, to do all the R&D…

We were in stealth for like three of the five.

Three of the five, sure. Thank you for correcting me. But nonetheless, even now you’re in open beta, and it is open source, and you can see a lot of it. It’s still in motion to become –

Pretty high barrier to entry though.

What do you mean by that?

Well, you have to like download the source code and compile it and run it on your laptop.

Yes, that’s kind of what I’m getting at. It’s still – it’s not easily accessible by everybody. I can’t go and free-tier it today.

But you will be able to soon. Yeah.

Okay. Do you see any looming Dockers out there to System Initiative?

[laughs] I mean, no. If I could see them, they’re not a Docker. The thing about Docker is that nobody saw Docker. And then Docker happened, and everybody was like “F**k! Docker!” You know? That was an avalanche of like a real sea change in the experience of what was possible.

Major change. For the better, right? Would you agree it’s for the better?

Yes. I would agree Docker was for the better.

Okay. I mean, my spicy hot take is I don’t think Kubernetes was for the better. I think we’re actually net worse on most vectors. But I’m alone pretty much in my feelings on that. But that could be because I’m a grognard. You know what I mean? It could just be that I’m, whatever. Old. So yeah, if I could see – if I knew what it was, then I’d be reacting to it already.

Okay.

But I don’t know what it is. I think the biggest challenges for System Initiative aren’t there’s some other disruptive technology that sort of eats my market share. I’m far enough ahead in terms of what the technology is and does that you’d be insane to try to do what I’m doing, because it would also take you five years. Even having prior art – you don’t really have prior art. The source code is not enough to understand how it works or why. That’s knowledge that the people who’ve worked on System Initiative have. But the market doesn’t have that knowledge, and wouldn’t even from the source code. So copying it doesn’t make any sense. I think it will later, but it doesn’t now.

I think our challenge is more that it is fundamentally a different approach to solving these problems, and that means that the experience of solving them is also fundamentally different. And so our big challenge isn’t going to be “Is there some competitive technology that beats us?” It’s just going to be, “Do the people who do this work love it or not?” Like, I love it. That’s the way I want to do this work now. Like, that’s the way the people who’ve used it so far want to do their work now. But will everybody else love it? I don’t know. And I can’t know, until I put it in their hands and make it easy. And in a minute, it’ll be three clicks and you’ll be in a workspace, and you can start automating some infrastructure, and it’s sick. And when that moment comes, will they love it? If they love it, everything’s cool. And if they don’t love it? Well, it was still my best game.

[02:00:22.06] For sure.

It was still the best thing I could build. It was still the best thing I could imagine. It was still the best way I could have possibly thought about using that capital to try to build something that I think has the potential to be truly transformative. And I want to build things that are transformative. I want to build things that push it forward. I want to, I want to move the art. So the challenge for System Initiative is that. It’s not there some other technology that will conquer me. That’ll happen later, because I am that technology… And so it’ll take a minute for people to catch up.

How does this work? …I suppose your outlook on the rise of platform engineering. You’ve grown up and you were there when DevOps was born, as you said in past conversations with us… I think it was [unintelligible 02:01:05.29] is that right?

Yeah, sure.

And now you have this rise of platform engineering. Does System Initiative dovetail and play well with this change of sea? Because you still have DevOps, but maybe DevOps serves platform engineering, and not so much developers, because platform engineering serves the ecosystem of developing teams on the larger team… I mean, I don’t know, how do you settle this?

I kind of settle it by thinking about what people are going to do with their time. So what System Initiative is good at is it’s so much quicker and safer and faster to use System Initiative to model infrastructure, and to look at how the system could work or should work… And it’s dramatic. And it’s much easier to extend to do interesting, complicated things. So as a foundational technology that people can use to build what they need to build, to solve their problems, it’s great.

Platform engineering is a marketing response and a technology response to the same fundamental problems that System Initiative looks at. You look at that same problem that says “Ah, DevOps teams - they’re not working as well as you hoped they were.” They’ve been struggling to like deliver the results over a long period of time, and as the system got bigger…” So then they have this reaction to it that says “What if in fact we were just wrong about it, and what we needed was an API all the time?”

We’ve had this conversation a bunch of times as an industry, where it’s like “We need portals. You need a developer portal, you know? And so you build a developer portal, and they could click a button and they get their little development environment. And then they don’t have to think about all the details, and it’s going to be awesome. And we do this all the time. We’ve always been doing it. And we’ve been doing it since I started working in the industry. But now, they’re like “Hey, what if that was the answer?” So what if the answer to this fundamental experience problem that we’re all having is a portal, that if we build a portal better and we make the APIs better and make the portal more flexible, and we make the lines between who builds the stuff that the portal runs and who uses it better, that the outcomes will be better. That’s their bet. I think it’s a dumb bet, because it’s being built on top of the same foundational technologies that delivered the terrible user experience you didn’t love. So how exactly is papering over that going to be better? It won’t. It won’t. Because you’ve already fixed the experience at the bottom. You were like “No–” The shape of the bottom infects the shape of the top. And so the actual lived experience, the actual outcomes of those platform engineering companies… Meh. It’s cool to have a portal. And you can make a lot of money having portals. Cloud Foundry made a lot of money selling portals. Here’s the fun part… It didn’t take over the world, and not everybody’s using portals. Weird, right? Not because they weren’t building you great portals. They really were. It was a great toolkit for building great dev experiences. And they made billions of dollars, and now nobody talks about Cloud Foundry. So you know, we’ll see what happens.

Good name, though. I like the name.

Incredible name. Great technology. Great people.

Cloud Foundry is an awesome name.

[02:04:04.18] But bad bet. I mean, not a bad bet. They made so much more money than Chef did. Just so we’re clear, it’s super-worked out for them, so why are we listening to me…? But as a technology, I think the problems with what’s happening now in that space, in operations, in the lived experience of those people is fundamentally tied to the way we’ve stitched all the different technologies together. It’s not that one technology sucks. It’s that when you put them all together, in order to get to the outcome you’re looking for, it doesn’t hold up as well. And those platform engineering stories are essentially stories about how we surface the stitching. Right? And I don’t believe that that’s going to change the outcome at all. I think it’s like changing – like when cars moved from having a key that you put in the stem, in the ignition, you turn the ignition, to having a button that said Start. It didn’t like change my life. I still started the car the same way, which is I push a button, and then the car starts; or I turn the key, and the car starts.

Your wrist is probably feeling it, though. I mean, for the positive, versus negative…

I guess… If you ask me if I want a key I turn or a Start button, I choose the start button.

Right.

But I think platform engineering is roughly akin to putting a Start button on top of what is essentially the identical car.

Dang.

And I believe that because I helped build the fundamentals of the car. And so when you dig into how it all holds together, you’re like “Well, of course it uses source control the same way. Of course it uses Terraform under the hood.

Of course it uses Pulumi. Of course, it stitches together this. Of course it talks to this under–” You know, all that stuff, it all has a way that it works, it has a way that you manage it, and you can’t really escape it. And it defines the outcomes in a very real way, both culturally and technically. So that’s my answer. And I don’t think it’s hubris. I mean, it’s probably some hubris, but it’s but it’s mostly just like – you kind of know it in your heart anyway. If you just sit quietly and ask yourself, “Okay, if I had a better portal over the exact same technology, with the exact same way that I was working before, would it be better?” And you’re like “Well, yeah. For people who need that thing, it’d be better.” For the person who just wants one. It’s probably faster to get one. And once I have one, what’s it do? Oh, the same shit before I had a button. Eh… Like, better to have a button than not a button. That’s for real. But did it change the game of what happened? No. Outcome’s identical. Button - better. You know?

Okay. So long on DevOps, obviously.

I mean, I’m long on platform engineering, because platform engineering is going to turn into whatever it needs to, be because all those people are playing the game. They’re all competitors… If what I do changes the face of platform engineering, they’re going to call it platform engineering… I will, too. Like, hold this space for next year when it turns out that my marketing message about second wave of DevOps or whatever is bad, and I pivot hard to platform engineering, because platform engineering won and I lost. I’m not above it. I will come back in here and I will completely be like “Nope, it was platform engineering all along. Can’t believe I said –” And the problem with everybody else’s platform engineering is the way they fundamentally build that technology. What a bunch of goobers. And that’s because I’m playing to win. I’m not tied to it. I’ll get behind the platform engineering train if that’s the train that pushes me forward into victory. And also, as of today, it’s not the train I want to be on. [laughs] But I will. I’m in. I’m down for whatever. I just want to win.

The last question and I’ll let you go, to your extensive, important, fun day that you have ahead, beyond this podcast of multiple hours at this point…

[02:07:52.26] This is super-fun. Yeah, you’re going to have to edit it. [laughs]

Lightly. We’ll lightly edit it. Honestly, I think it’s all good stuff, and I’m very happy with the conversation. So you’ve alluded to fall… You’re in private beta now. You said slide in your DMs for System Initiative.

Yeah. Find me on Twitter, send me an email… I’ll hook you up right now.

I can see - and maybe you can see the horizon probably better than I can, because you’re in it. What is just over the horizon? You mentioned fall. What can you mention here for the first time ever, or at least tease for the first time ever right here?

Yeah. So one of the things that you do in System Initiative is you customize the way this big – it’s got this big hypergraph of functions that is the thing that actually writes the configuration and sort of runs a simulation of what it is you kind of want to do. That whole thing is programmable. And so the loop of how you create new assets and add new behavior is getting very tight. So for example, you push a button and then you can create – let’s say you needed to automate your CDN, and we don’t support that yet. Or your own application has like a deployment mechanism that’s custom. You could just click the customize button in System Initiative, you write some JavaScript that defines the properties of the asset you want, and then you write functions, just little, short functions. The longest ones are maybe 100 and 200 lines long. And usually that’s because there’s data in them, not because they’re that complicated to write… That are what actions you would take.

So you want to deploy actions, so you would write a little function that describes what it should do on deployment. Or you have a qualification that you want to run when somebody puts some data in to tell them in real time whether or not the configuration is good or bad, or whether it worked or not. So for example when you use like IAM rules in AWS for doing security stuff, AWS has a way to validate those rules. That’s a qualification that we wrote for the IAM rule. So when you’re like using an IAM policy, every time you change the policy, it runs the command that validates your policy and tells you if it’s good or bad and shows you in real time. It’s sick. All of that is stuff you can do yourself, and you don’t have to ask me anything.

And then there’s a little button, and that little button says Contribute. And if you click it, it tells you that you’re agreeing to the terms of the Apache license, that we’re going to review your code. And then you can push the button, and it’ll come to us, and we’ll review your code, and then we will ship it. And we’ll do that loop over time.

And so I think what’s on the horizon is I think this new way of building automation gets connected to the creativity that is latent in that community, where because the tooling has been the tooling now for a while, it hasn’t been the most creative work to do DevOps stuff… Because mostly what you’re doing is “Oh, I’m writing more Terraform.” “How long have you been writing Terraform?” “Well, five years. Doing GitOps, you know.” And suddenly there’s this thing that’s very different, works in a very different way, and is fun. And so I think people are going to have a lot of fun writing stuff in System Initiative, and making it do things, and then sharing it with each other. And I think that’s what’s going to propel it into the world. It’s not because System Initiative alone is going to build all those abstractions. It’s because you can build whatever you want with this fun machine I made you. And so we made you this really fun machine for building automation, that has this really interactive loop of programming it, that like it’s fun to program. And you’re going to go and program it.

And so people are going to look at it at first and they’re going to be like “Oh, this is – whatever; it’s visual design for architecture stuff”, and that’s what they’ll see first. And it is that. But under the hood, it’s actually just this really fun programmable machine. And I think that what’s on the horizon is that that community of people, once they catch on to the fact that what we’ve given them is this incredible way to program their own machines. I think they’re going to go nuts programming the machine.

[02:11:57.28] Would you think that these shareable, contributable, programmable things that you’d mentioned too written in JavaScript would be comparable to the way Docker Compose, YAML files have helped people who don’t really understand Docker stand up a new Docker image? Is that a good comparison?

Yeah, kind of…

I mean, because that’s shareable. So I can go grab a Docker Compose file… As long as I have Docker on a machine, I can run that, I can [unintelligible 02:12:20.00] and off to the races.

Yeah. This is more like – I’m going to go again with the Wayback Machine, but it’s more like Lisp, where there’s old Lisp machines… Like, if you wanted to change the way the application worked, or like the window functioned, you could click a button in the window and it would just pull up the source code, and then you could just change it. And then the operating system would now be different. And you were like “And now it did new things.” It’s more like that.

So because what System Initiative is under the hood is this modeling system for this graph, the way you program it is different… Because what you’re doing is writing functions that inform how the graph should behave at different points in time. It’s just a really different way of thinking about it.

So they’re shareable in the same way that maybe like a Compose file is. But to the user, when you bring that asset in, it’s like suddenly there’s an asset and it shows up on a canvas, and it’s got input and output sockets, and it’s got properties, and it does cool things.

So that’s pretty – it is similar in that you can share them and it’s repeatable… It’s different in that the way you interact with it is like much more visceral. You’re just like “Oh, I need one of those.” And then there is one. And then if you don’t like how it works, you can just open the source code and tweak it. And then you could contribute that back in a single, seamless loop. Not by forking a repository; literally by just examining the code for the thing you already have.

And over time, we’re going to make it so you can hold that patch, and when new updates come to that thing, it’ll just tell you “Hey, you also added this extra property. Do you want to keep it?” You know?

Yeah.

So it becomes this really interesting programming system.

I like that.

And I think that more than anything is the thing that’s going to really propel it, because I think they’ll come for the ease of use that is like - that’s so much easier to model infrastructure, and to see what you’ve done when you’re finished, than looking at like a Terraform repository. If you’ve ever looked at Terraform and tried to understand what it does, it’s actually really hard to do from reading the code, because there’s all these layers of abstraction, and variables and stuff that sort of do it… System Initiative you kind of see an architecture diagram that looks roughly the way you think it should.

And so that’s what’s going to bring people to the yard first. But they’re going to stay because they’re going to realize that that machine is programmable, and they can make it do whatever they want. And that’s where it becomes the power tool that actually has enough potential to change how we do the work broadly. Because if it couldn’t do that, then my ambitions are too low. You know what I mean? I want to change the game, I don’t want to just improve it a little. I want it to be fundamentally different. I want there to be a day before and a day after, you know? And I don’t know if I’ll win - back to being a professional - but oh, I’m giving it.

Everything you’ve got.

I’m bringing the heat. And we’ll see. Sometimes you bring the heat and you lose. [laughs] But I don’t think I’m going to.

Truth. Truth.

I think I’m going to win. But we’ll see. I don’t know. I’m on the edge of my seat, you know?

In the words of Gavin Belson, he said “I look forward to the fight.”

Yeah, I look forward to the fight.

Yeah, I like that a lot.

Yeah.

Alright. Well, SystemInit.com is where you’re planted your roots now. Maybe not your identity. I don’t think so based on what you said. But definitely where you’re planting your professionalism and all your effort in the space of DevOps.

Totally. And yeah, you can send me an email, I’m Adam [at] SystemInit.com. It’s pretty easy to guess. So if you want to try it out on the SaaS platform, and you got to the end of this incredible podcast, you deserve it. Feel free.

This is your prize. Adam’s giving away access to the DMs, and the private beta.

Yeah. Or @adamhjk on Twitter or X, if that’s still a thing you use… But you know, you can totally just come and I will hook you up. Just tell me about the Changelog.

Very cool. Alright, Adam. Thank you so much, man. It’s been fun.

Thank you, Adam. So fun!