From Chef to System Initiative (remastered) (Interview)

40:27but 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 um i'd already decided that like that the the game here was figuring out how to how to like start a business and make a bunch of money and so like you know working in arizona we were all contractors because you couldn't get a job working for the power company, right? 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.

41:03And, uh, so we built, we started our own contracting company and hired everyone and gave them all a 20 % raise and just like took a smaller nut, you know? Um, so we were already kind of in that zone of like, how do we figure out, like, let's figure out how to make a bunch of money, basically. Like, obviously there's a bunch of money to be had. we should get some and so we so when they started zimian i remember being like oh man like it's all open source they described how they were going to make money and i was like that could that could work like you could have all of the goodness of like the openness and the sharing and like that could then make you into a bigger business and that was the first time that that entered my mind that like what you could figure out how to do was like build open source and then use the success of that open source to sort of catapult you up in business.

41:55And then there was a series of others that sort of moved in that early era. There was like, you know, like VA Linux and the people that now run, that now run one of the Red Hat clones, Rocky Linux. Like 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, I was like, bad, you know? Wow. And like, so there was a couple of those things happening. And then Red Hat, of course, happened. And I loved Red Hat. And so, and they treated everyone so well in that era, really. And when Red Hat IPO'd, they made a ton of people wealthy.

42:36And I was just like, yeah, that's the way. Like, we should figure that out. And it was obvious to me that it was important on a philosophical level. so like because it had made such an impact on my life like i had this career i was making more money than on than any of my friends were like i was we were doing well and like that's um that was all because of linux and it was all because of open source right that isp that i was running red hat on like they loved me because i had saved them tons of money right um and what evolved over time was that there was like a, I love that strain of like human goodness that lives inside of open source.

43:14I love that, like that ethic of sharing and that like more is more, you know? Like we can, the pie can get bigger and then everyone can eat. And like, and that, it was just so, it's such an ingrained thing in me now. But yeah, it was very motivating and very, very real. and felt achievable, but then you have to figure out how to do it. And so it was like, you know, we tried to start a half dozen businesses, you know, and, and failed. Um, but eventually, um, we basically those, those same guys that I worked for for a long time at March X, um, March X went public and I had a pile of stock and I hadn't made any money from any of really meaningful money from any of those companies I had worked for.

44:07And so they had IPO'd and my stock basically vested. And for the first time, it was also above water. So I would have made, you know, not life-changing money, but like 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. But in order to sell my shares, I needed to get their signature from the chief legal officer. And there was this like coterie of executives who had been doing this together this whole time and it 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 like decade of dutiful service or whatever and he was like no and i was like well but i don't have any like proprietary information about it i don't know any special secrets or whatever like please can you do this and he was like no because it would inconvenience me and this is what he said it would inconvenience me and and our ceo and like all my friends so no and i was like just no he He was like, yeah, just no.

45:20And 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. I these people obviously give about me, you know, and so we should start a consulting company. I'm done. And like, 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 built full.

45:59We started building fully automated infrastructure for startups. And that became HJK Solutions. So me and Nathan Hating Smith and our friend Sox Siri. And then we added some more people, Barry Steinglass and a few others. And eventually that became Chef. Yeah. Wow. But it was the same people, you know, dreaming about how do we figure out how to start a business? How do we figure out how to like build a company that IPOs? How do we figure out how to like do all of this? You know, like we wanted it and, but we didn't know how to get it. And so we just, we just kept, kept taking shots, you know? Is it a HJK?

46:40Is 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 like yeah so i found the first contract um where i basically what the what we what we sold was you'd pay us a fixed fee and we would automate everything so application deployment monitoring trending uh operating system installation um identity management backups uh database management all that stuff so big long list and we would fully automate all of it for a fixed fee so you know you'd pay us 20 grand and we would deliver all this automation and then you paid us a retainer to maintain it um and the 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 um yeah it was great we were we were murderers um uh like she We should say that given the history you've shared.

47:45But like, this is how I met Jesse Robbins, who is sort of integral to the chef story. So Jesse was the master of disaster at, uh, at, at Amazon. So Jesse, um, and, and if you ever meet him, he's like a larger than life human, like is 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, you know, 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 consulting company. But if you build a product, call me.

48:21And so we had done, we had grown. We had a couple of people working for us, mostly our friends. We had, you know, maybe a dozen clients. And we were using Puppet at the time. We built a lot of automation on top of Puppet. and there was this horrific moment where Puppet 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.

49:01And 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 like, you know, your resolve comp file or whatever would just go away and it would be replaced with just a checksum yeah totally that's the worst ever it was so bad so this happens to this happens to like our biggest client right um and i hop on irc and i'm like yo dogs you know have you seen this horrific thing happen and the channel is like oh yeah we know about that one and like links me to the bug and i'm like what we you know like how what memo did i miss and this isn't fixed like how did this not just how did it not pop to the top of the community's stack you know you just you know like i should i like i was paying attention i was pretty involved and like i didn't know so anyway this bug comes in and in the bug report there's you know 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.

50:29And 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, like it just overwrites files with checksums and you're just like, I'm out. And he was like, yeah, I got to 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 what if we just worked together how about i put my labor um 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 like you know you should go somewhere don't do that and i was like dude i'm not paying you you know like i like i'm 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 got a consulting company to run.

51:25We 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. 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, you know, he accepted the PR, but was very angry at me because I had like undercut his model and taken food from his children's mouths. And so I was like, this probably can't stand.

52:07Like we can't continue to be, I don't want to be the consulting company that is like the best in the world at this technology, but that also can't, but the guy who writes the technology hates us that's like 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 got to figure out like how this big graph works it's a mess like and they were just they were like you're an idiot if you didn't if you didn't do it if you weren't such a big dumb dumb this wouldn't be a problem um and so i started writing chef on the side.

52:43So my partners took over all the work and then I essentially took a couple of months and wrote chef and 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. Like, let's 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, who 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.

53:28So when we had a pretty great launch and Ezra supported us and the rest is history. Wow. I can remember some DMs with Ezra. um and i was sad because obviously he passed away and i had met ezra around at the engine yard offices in san francisco 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 said we went upstairs and sat down on the couch yeah the two-story yeah you know that's that's where we perfected chef there you go that's awesome and i was like dude you're so cool he's like you run this company i mean you're just so cool i think it was i forget what year he passed away it was like several years later but i wanted to get him obviously i'm a podcaster right i wanted to get him on a podcast eventually and i was like going through my brain of like people that i've met over the years that were influential to me and i was thinking gosh man ezra be cool to get him on the show and get us on the share like where we're at now this is like post way post engine yard yeah but that was like the foundation for so much so much in like the early ruby hosting days for sure but then also a lot of the cloud development that's happened and oh yeah it's just way ahead of his time it was and and he and but when you think about you know that early internet and the culture and the people and open source as was a perfect example like yeah ezra had no ego about Ezra 100 % could have written Chef and it would have been a bigger deal than me.

55:01I didn't matter, you know? 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, like not only did he help me, he like incredibly raised our profile, you know? Because he was the most high profile person in that space at the time in the 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.

55:38And 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 uh 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 the, there's this severity one awful thing. And his answer was basically like, you must pay me or I won't fix it. And I was like, I just, I can't even with that.

56:20Like, why wouldn't you see that this is a thing you must fix? You know? Like, it's obviously terrible for your product. I want to dig into the whole you must fix because I'm sure you know how open source works, Adam. I'm talking to the person I go to for answers. Well, now I got deep philosophical questions about open source and the way it merges with our freedoms in it. 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, because product-wise, you must. If you're trying – like what Luke wanted most, and we'd spent time together.

56:55I knew like Luke wanted the ring, like Luke wanted it all. That's that was what he wanted. And so like 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 like this is phenomenally bad for you? Like when you think about just people adopting the software, using it, trusting it, you know, Puppet was on the rise. And like, here's this lurking time bomb. it was the thing to use it was absolutely the thing to use and like and it was great and like and here's this time bomb you know sitting in the middle of your product and like and that's not your most that's not the thing and like i just didn't understand it right and and 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 like that's what i want to clarity on like fixing it myself was a fine answer him being like look i'm too busy i got stuff happening i gotta feed my kids i'm like great feed your kids i'll i'm willing to do it but he was mad i fixed it because if 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 like it sure felt that way to me and to a bunch of other people that were there at the time and like you know i think 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 like for sure because there's perspectives yeah there's perspectives luke's not a bad guy like he's like whatever we're not besties but like i don't hate Luke, I'm not like carrying around a weird grudge or whatever.

58:25But yeah, it was, it was more of those pieces I couldn't understand. And then for me building my business and I was out stumping, you know, I was going to conferences, giving puppet talks. I was like, I was telling people this was the way and teaching them how to do it. Cause 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 the trap of, you know, in this, in this way. And so inevitable resolve conf file getting over written with a checksum right that's bad news it was it was that you couldn't even personally reproduce you know it happens at random yeah yeah it was bad and like reliably and so yeah it was it wasn't that i demanded that he do the work it must was like it's clearly you must fix it for your survival for your own best interest um 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 they maybe they would have called Luke you know yeah 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 um because you know it felt like a it felt like you know 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 did you I know you didn't steal any code obviously but did you did you borrow any I I mean, because open source is like, it's art.

59:45And art imitates other art, right? There's borrowing that happened. There's influences that happened. It was 100 % influenced by Puppet. If Puppet, like there's a bunch of things that Luke invented. Like the resource, the declarative resource abstraction, that idea that you like, that you would just say, like, this is the file and here's the shape that I want it in. And then here's like a package and I want that in this condition. Like there'd be no Kubernetes without Luke Kinese, right? Because Luke Kinese was the person that created that abstraction that says, here's how I want to declare this resource.

1:00:15And then that resource maps to something real in the world. And then there's a loop, a reconciliation loop that solves those things and that you lay them out in the way you did. That was all Luke. And like 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 like, you got to praise the man for it. You know, like if he hadn't done that, where would we be on a fundamentally different trajectory, you know, and like Luke Kinnis is a genius, right?

1:00:47He's brilliant. And if it hadn't been for Luke, like chef wouldn't have looked like that at all. Cause I didn't, I wouldn't have come to that conclusion. Right. But I had his prior art. Right. 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. So like, you know, but, and it was a fundamentally different product because of it, but, um, but it doesn't mean that I wasn't standing on his shoulders. You know, if there wasn't for Chef, there'd be no Pulumi, right? There'd be no CDK, right?

1:01:20Like those ideas of like, we should, you should do the automation in a real programming language. Like Chef was the first of those really, um, that wasn't just like writing scripts, you know? Um, and you know, so it all, but it all stands on each other. Right. For sure. Yeah, it's interesting how, just how that plays out, like that, that you can be a part of that. And I think one thing you said was that you were using Puppet in ways I don't think it was not, I'm trying to paraphrase this in a degree, you said like, in ways beyond it was planned to be used. Not planned. We were using it more than most people.

1:01:56So like most people were using like 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, you know, they were replacing CF Engine 2, which was like setting up a config file and like making sure that the patch ran. You know, there was like a half dozen resources they were managing. If you're managing 100 resources on a single box, that was a big deal. We were running, you know, our standard config on a single host was 300 plus, you know, 400.

1:02:31So like 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 like Facebook apps, you know, so people were like, couldn't get enough stuff, couldn't get enough gear. We had a customer I like who was one of the first music sharing things. And it was a Facebook app. And so they had a billion users immediately. That was unheard of, right? That was not a thing you could do on the internet before that moment. And it brought social media into the world. And so like, they literally were calling all of our friends being like, do you have any gear?

1:03:03Like, just can we, can we just, we just want to buy whatever you got. We don't care what it is. We'll take it. We'll put it in racks. Like we can't, they couldn't scale fast enough. And so they were using our kit to scale, you know, like that automation is what allowed them to do it, which was awesome. But like you, you know, and their own intelligence. I'm not saying we did it like for sure. Travis Cole. It was all chef. Big ups. It was all chef. It wasn't chef. That was puppet. That was all puppet. We were using puppet to do that. And like big deal. Right. And like, yeah. And like, you know, it was just, it was, it was a, it was a pretty fun, interesting era.

1:03:39Yeah. So if my notes are correct, this beginning of ops code, not chef. Yeah. Was in 2008. Yeah. Roughly. Probably right. Yes. so let's say maybe 2007 but it happened in kind of yeah hjk had been going for a couple of years so like right you know you can backdate that to did you literally i mean this is probably a boring minutiae to some degree but like did you literally convert the company hjk to a different company called ops code or did you like just end the consultancy and found a new um 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 it was yeah because we knew what was there we knew what the diligence was Yeah, I mean, this introduced me to a bunch of new interesting ideas.

1:04:22So one was that you could like, and Jesse knew these things like Jesse, Jesse had been studying the business of venture capital in a way that I hadn't I was I had I had been but I was uncertain still and Jesse was like not uncertain. And so he, you know, you know, we, I learned that you like, shouldn't 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, you know, he had a lots of, he was, 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.

1:05:09Those 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, you know, there were allowed us to sort of successfully raise capital. But we had a hard time raising like we, you know, I think we pitched. Jesse would know the exact number, but like 15, 20 times and got no's. And, and the, 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 like near his house. He like held court at this coffee shop and we gave him our like sad dejected pitch.

1:05:48Cause everybody told us to like raise less money basically. And so we had started out asking for two and a half and, um, and we had gotten all the way down to like, please give us half a million dollars. We promise it'll work out. And he was like, guys, this is a sad pitch. Like, is there like, is there like a business you believe in hiding in here? Is there like a, is there a way that we all get like a billion dollars? Cause if so, I want to hear that pitch. And we were like, well, yeah. And so then we like gave him the billion dollar version. He was like, that's a good pitch. That's what you, that's what we're going to do.

1:06:21And he's like, and you're going to ask for three, ask me for three we were like okay three and he was like great no yeah exactly he was like no but i'll give you two and a half and we're his terms you know but like and that worked and you just you know you just did it until it worked um and yeah so two and a half mil that was your initial funding i think so probably or three but like did you have a i should remember yeah at what point were you okay because we hadn't launched it we hadn't launched it yet so um we launched it we announced the fundraising and we launched Chef at the same time. Did you launch Chef as open source then from the beginning?

1:06:59Yep. Yeah. 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 um and so you'd already done all that automation for engine yard prior to this even this pitch yeah yeah yeah yeah fundraise okay yeah and so so you knew you had faith in what the software was able to do in its infancy yeah and like you know it was like it wasn't a great launch you know it was like a you know our color scheme was like gray and blue and you know like it was like a website built by systems administrators you know lots of squares but like Like, um, but yeah, it, um, but what, but what did happen was like, there was very quickly a community of people who we knew from Puppet and we knew from the Rails community who like really attached quickly to Chef.

1:08:02And then, you know, we knew that we were building a community and it was all open source. And so we just embraced everyone who would listen. So like anybody, and you know, at that time, like open source still happened on IRC primarily. so you know 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 you know 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 like use the software but solve their like root problem in a deeper way so So like one of the things I used to do at the end of my conference talks every now and again was I would just like I would ask people how many people use Chef and how many people use Puppet and how many people use CF Engine.

1:08:52And like I would offer to fix their problems. Not by converting them to Chef, but just like I knew CF Engine really well and I knew Puppet really well. And so like you could come to me with your Puppet problem and I would like fix your Puppet problem, you know. And so we just we we we really intentionally tried to build a community because at the time. You know, this was Tim O 'Reilly's like create more value than you capture. Like 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 Web2O Summit and around like a couple of those conferences.

1:09:27And so that idea really captured us and we really was like embedded in that business plan. And I think we did a good job. So, 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. 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.

1:10:12And 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 sass product big multi-tenant sass service um that did okay but didn't do great and all of the large customers banks and insurance companies and stuff like would just run the open source because they uh they they weren't willing to run a hosted product a decade later they would all come to me and be like can we just buy a managed can I just buy a SaaS?

1:10:54And I was like, you guys, like, I did this for you. I did this for you. And now I have led it founder because you didn't care. But yeah, that was it. So that was the original business model was SaaS. And then it turned, you know, 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. But - I've never heard the story. Yeah, I mean, we've gone through, like we went through every possible open source business model.

1:11:34We went through like, you know, we started out SaaS plus open source that you could run on-prem. Then it was, we had the open source version and then we took the SaaS version and we sold that as an enterprise version that 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 don't remember what the time goal was but it was like five minutes, 10 minutes from scratch.

1:12:06And 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 like 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 and so it's just like the erlang just literally ate all the load and just didn't care without breathing it was incredible the first time that we'd used it outside the lab um it was truly incredible so So we were like, hey, if you want the good one, you know, pay us for the good one.

1:12:53And then that 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, then what we actually should do is, like, you can't hold back basic security. That makes you kind of a jerk. So then, you know, maybe we'll build like a dashboard, like a better web UI. We'll monetize that. You know, maybe it's security and compliance. We'll do that. We made some acquisitions, brought in the InSpec folks. You know, that was great. They were awesome. Their code was incredible.

1:13:22It helped. You know, we tried every variation of OpenCore possible. And then in the end, switched to a model that looked like RedHats, which was the most efficient by a dramatic margin.

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1:16:24Would 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 yes and no. You know, like 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 like 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, like the impact we had on the enterprise, the client list we had, you know, um, we were still growing at a reasonable clip, but, um, yeah, I would say, you know, a lot of people tell successful startup stories and they, they always draw like a smooth line, you know, sort of up into the right.

1:17:09Um, that's, 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, and you didn't have enough life experience or business experience to tell the difference. So like, you know, 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, you know, the business model worked out. So like, but I wouldn't say it was easy you know and and a lot of it was wasn't so much it was never the technology or it's always people you know like 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 and I think the yeah it was it was it was it was hard um you know at the same time we were quite successful and it was really fun and like and I you know I had no regrets I would do I would do it roughly.

1:18:08I wouldn't do it the same way. I'd have changed the business model if I had hindsight, but I think, but yeah, I think the, yeah, it's hard. Um, what that did for me was professionalize me. So, you know, 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 you know with our own with our investors our customers they were like are you you guys are dead right like it was just it was awful and you know 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 um so like because the company was real that was really down and so the barry chris asked me to like give him a pep talk you know and so i went and watched um al pacino did a football movie uh whose name escapes me um uh which one was it any given sunday it's any given sunday yes any given sunday and the end of any given sunday he gives the greatest inspirational speech ever put to film you know he's basically got this this bunch of football players and he's like life is a game of inches and you gotta crawl for it.

1:19:28You 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 you know it rallied the company um but as soon as i was done giving this speech i'm so grateful that i was alone um so we had this office in san francisco that wasn't full of very many people and uh it had a beanbag because whatever startups and i just collapsed and wept for like half an hour like like 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, you know, what if it, what if we lost, what would that mean?

1:20:34What'd that say about me? What would it say about them? Like what would happen to their lives? What happened to mine, my family and all of that pressure and all of that, all of that was so intense and I just couldn't hold it anymore. And I realized that the problem was that this had become my life and not my job. And that it was, you know, there's a part of it being your life that's helpful when you're trying to do something new. When you're, you know, you hear musicians talk about this all the time where they didn't have like a, you know, they didn't have a plan B. Like, that's good and can be helpful.

1:21:16But like, 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 going to 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. And it had to become about the work I was doing, not about whether or not it was going to happen for all of these people. And, um, that really transformed who I am into a person like now, what I am as a professional CEO, I'm a professional entrepreneur.

1:21:59Like I do that. It's my job. Um, but it's not, it's not who I am. Um, and that's the moment that it, it, I stopped. It stopped being who I am. It's interesting to be 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 like your identity was deeply ingrained tied to tethered to and your self-worth yeah you know you are as adam jacob like your worth is like oh is chef successful no or okay well you're you're 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 hate chef you know and like he just hang random stranger felt entitled enough and i was like i'm sorry i wasn't thinking about you when i wrote it you know like i didn't mean to hurt you but like i had way more people tell me that it changed their lives and how it impacted their careers and their families and like i have a million lovely stories of that and like i but but yeah it does sort of at some point you have to decide like what fuel you're going to burn because you're on this long journey you know it takes 15 years.

1:23:13And, you know, if the fuel you decide to burn is your own self-worth, your own, your own belief in yourself, like you'll run out eventually there'll be enough things that tell you that it's not real, that you'll, that'll be it for you. And so like, 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 like, it's been, I'm 46. I've been doing it. We just talked about I've been doing it since I was a kid. Like that is a huge part of who I am, but it's not all of who I am and it's not the, and my success or failure doesn't define who I am.

1:23:46You know, I'm going to be good at it, whether I win or lose. Um, I'm great at it, um, because I'm putting in the work to be good at it. Um, 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 teams feel in the same way, you know, like 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 like you can't control it um but if you're burning self-worth you know if you lose and what you burn down is your identity your self-worth your belief in yourself like it's tough to get back up again you know it's hard to it's hard to decide to keep going and um but if you're but what if but if it's professional acumen if it's skill then it's just now i'm a pro now it's a now it's the game I play and I'm doing my best to play it well you know 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 yeah right yeah yeah because like you do some things sometimes in life and you're like that sucked what purpose did it did it have right it was good training that's good it wasn't burn adam down whether i'm talking to you or me yeah 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 and don't let it be self worth burning no it can't because it can't be because or team burning like that sucked for us like we suck as a team because we just went through this thing does that make us a bad team yeah does that you know and i i yeah and i'm i'm so grateful for those moments and i'm so grateful for the opportunity to have had them and like and and yeah but i wouldn't still be doing it if i hadn't if i hadn't had that revelation that like 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 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 my how i put in the work i can control how i like the 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 like that's a thing that i can do and uh and and in the sense of good training if even if i fail it's good training i'll be better like i'm gonna learn from it all my game will get better i'll i'll be able to figure out how to how to how to motivate it um yeah not to go too deep into this scenario for you but when you gave this speech and you said you were in quotes trying to hold it together you must have been terrified like 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?

1:26:53What were you trying to accomplish? 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're 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.

1:27:31And 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. And that 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 in this moment, there was a moment where, you know, nobody would buy it for a dollar.

1:28:14And this is a company with, you know, tens of millions of dollars in revenue, recurring, growing 20 % year over year. Like it's great. Not one fucking 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, right? Like we figured out how to land that plane and like, I'm so proud of it, But that was because those people didn't lose faith in each other. 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.

1:28:56Sometimes 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. Yeah, yeah. Yeah. And thinking about it now and talking to you about it, like I've been like welling up now just thinking about it. Like, I don't think I'm going to cry, but I might if I do great podcast material. But like, sure. Um, I like, yeah, I, yeah, of course I was giving it to myself. Of course I was. And look in, in the years since, like I've been in therapy and like learned a lot and I'm improving, but like, it's not easy for me to talk about like most people, but like there's some people for whom they can talk about how they're feeling.

1:29:38And it's like very difficult for me to talk about how I feel. You know, if you ask me what's happening, I'm gregarious enough. I'll tell you like 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 like, like I wasn't sound like I was expressing to other people, anyone else, even including my wife, like 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.

1:30:09and like um and yeah so there was a lot of there was a lot of internal pressure that had sort of built up there that needed that needed needed release i think part of why the speech was good was because that same energy came out in the speech you know like i used that as fuel and because i had allowed that to happen when i gave the speech like suddenly all these emotions I had not been processing and hadn't been holding on to, like, like 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? Well, thank you for sharing that.

1:30:51I 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, right? Or 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, right? It's an error or it's not. It runs or it doesn't. Whatever, right? 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.

1:31:36Totally. 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, I, I, I, 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, like there wouldn't be a system initiative, and there wouldn't have been a chef and there, you know, like, there, like, there's so many things that would have not happened or would have happened differently.

1:32:07and I think you have a responsibility at some point when you when you reach a certain level of professionalism to help other people climb that same pyramid you know like like if it wasn't for Ezra like where would I be you know and that 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 like 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 um and I think people who don't feel that responsibility um or who don't do it or who actively close that door like to be honest I think they play the game less good like like I think in the end it comes back around you know um and I think a lot about like you know I don't think a lot about it well that's not true I have this like tattoo so I do think a lot about it but like um it's just like it's the it's just three lines that reminds me that i have things that i that matter in my life um and that they're that they're that they're not all equal you know there's some things i care about more than others and i should focus on the things that i that matter the most so like my family um and uh and it's like in the shape of it's kind of rounded off sort of like the like so big 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 in the lines and then we tattooed it on my arm but um but it's there to remind me that like that i have things i value and i have like and that i i need to keep those things in my mind while i live my life and i think that there's a you know 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 like like there's things that i'll do that will matter when i'm gone and you know i hope somebody on some podcast someday is like, man, you know, Adam Jacob really did blah, blah, blah, blah, blah, and helped me in this way.

1:34:04And they can be like, rest in peace, Adam, you know, pouring out for our homie. And like, I hope that day is far away. And, you know, like, I don't want that to be now. Thank you. But like, but, but I, but I care more about that than I do about winning. You know, I care about how I win, because I really believe that you can win better by, by doing it that way. Like you can win by being good and by being a person who cares and being a person who helps other people. And like, you know, I think like there's a company that I talked to not that long ago, just getting started. Absolutely going to wind up competitive to system initiative with, you know, started by a bunch of very credible people who, you know, I helped them get funded because I introduced another person who should fund them.

1:34:52I 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 like you know i hope they have all the success in the world because it's not a zero-sum game you know like if they 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 and i'm gonna i'm gonna fight like hell to do it um but you know if they beat me so be it you know like some days you win some days you lose yeah but let's go you know yeah for sure are you um 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 yeah i watched that was most of it and i don't think i watched it all the way to the end same thing a little too close to home you know it's like like i can't watch the um i can't like i really struggle to watch all the dramatizations of like crazy founders who do fraud like i can't watch like the elizabeth holmes documentaries well there's no fraud in this one well there's a little bit of blurred lines but i know but like i have this like i have this deep part of me like i i was playing mass effect last night the first one and i decided i was going to try and be a mean person and i literally couldn't make mean person choices i feel you that's how i am i just couldn't do it and so like i can't make me mean person choices either so so when i watch those things and i think about myself and the part of my job that requires me to go out and like and sell.

1:36:24I'm like, ooh, am I a fraud? You know, did I lie? And it like keeps me up at night. And I didn't. And I'm not. And also like it gives me anxiety. So I stopped watching Silicon Valley because it was too much. You know, I was like, oh, nope, that's too much of my life. And whatever. It had a chef cameo. There's an episode where they talk about chef, like the chef guy comes in, you know? And I was like, I can't with the show. It's too much. Anyway, keep going. Silicon Valley. Well, the reason why I ask is because there's... There was a scene where Richard Hendricks, which was the main character you're familiar with because you watch season one at least, you know, was juxtaposed against Gavin Belson, pretty much the entire thing.

1:37:04Gavin Belson was the villain. Right. He was the one that was doing the fraud and he was the one that was blurring the lines and treating people like disposable, you know, 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? Yeah, we can't all be Hooli. And there was a point in this 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 because you will not sell to me. You will not be absorbed by my behemoth and I shall look forward to the fight.

1:37:47And it's almost like what you said there was, 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 going to have better competition. A sign of winning is competition. Yeah. Like Puppet was winning, therefore Chef existed. Yeah? Yeah. And like 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. You know, I validated that market.

1:38:23I like, like we grew together. We did that together. And like, you know, yeah, all the competitive juices, like I really think that's how you need to look at it if you're a professional about it. you know 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 like if it's those things you're worried about different problem you know it's different when somebody is like when you're worried about whether your kids are going to go to college and the competitor like that it hits harder you know 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 like yeah when i think about that competition i'm like yeah come validate this market come come come come be competition not because i don't and i like you like let's let's you know like i'll i'll help you up the ladder and like i'm still gonna beat you you know like i'm still gonna look you in the eye across the metaphorical court and like you know i'm gonna be the best player i can be and like i'm gonna i've been training hard you know yeah so like literally training hard yeah and and like so like let's figure it out let's go you know and i i want that like i want i want there to be competition i want it to be difficult in that way i want to win but not because uh you know i don't want to win because i i murdered everyone i see you know like that's no fun yeah 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, you know, like they're the ones you can most talk to about like, oh, that's awful.

1:39:57I'm so sorry that happened to you. I know what that feels like. They're also your peers. Like they're the only other people who know what it's like. So when you think about like, like destroying that pool of people, like, of course, I want to help people up in that way because like, I need those people, you know, I'm going to someday I'm going to need them. I'm going to need to call them up and be like, oh, I had to do this hard thing. And they'll be like, oh yeah, I understand. And like, you know, they'll like be there for you. In a way that they won't, obviously, if what you did was punch them.

1:40:27Don't punch people. Not if you can help it. Yeah, unless you're in a mosh pit. Sometimes you got it. Fair game. Yeah, I mean, probably not. You're kind of a jerk then too. Yeah, I suppose. Well, at least 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. 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 going to have to punch someone you'd prefer to be the one who punches first than second what is it that matters to you adam like i know what you're doing now let's let's fast forward a little tiny bit and i'll do the job for you eventually you sell chef i don't i'd love to get into the details of that like i know you kind of stepped away in a way i don't know the full story i 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.

1:41:20I'm not really sure of those, 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? Um, the, the people that I love and the life that we can create together. Um, I care about my family. Um, and I care about how, how that my family goes forward in the world and like what their lives are like. Um, that's the thing that matters to me. I know that's cliche, but it's true.

1:42:09and then I care about how I spend my time you know like the you have a limited amount of it and so you know I need work that is compelling I need I need to care I need to believe that the art of it is worth doing right um because because the I want to play that game because it's the funnest game I've ever played you know it's the game I've been playing since I was eight so like it's still the game I love the most you know so like like I kind of feel like it's one unbroken line of training from, you know, running a bulletin board to now. And it's just one unbroken experience of like training to do this kind of thing.

1:42:47And so, yeah, I, we sold chef. Um, um, I had stepped away, um, very slowly. I basically left when 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, I basically took a year to do it by just sort of. You were CTO? Yeah. That was, okay. Yeah, I was CTO. And I just sort of, we like 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.

1:43:25Because 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 into it. 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, but then, yeah, I took some time off and then, you know, with system initiative back to like what motivates me as a person, this is how I'm looping you back into that answer.

1:44:11Like in my work outside of my personal life and the people I love and, you know, those are my atomic family, but also my chosen family. I have a lot of people that feel like chosen family to me where like, you know, I'm in it for life with them and I don't care what they do, you know, that I don't care what happens. like those are my people and they're going to be my people no matter what. And, you know, 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. Right. That love is unconditional.

1:44:41And I, I, 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. and 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, are having the best experience they can have. You know, like 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.

1:45:21I'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. Um, and like, 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, on how to build that automation.

1:46:05And it's a transformatively different user experience. And it's, 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. Like that's, that is new in a fundamental way. And so I love the newness of it. I love, I love the art of it. And it's starting to turn over like a business. And I love that too, because like you get, there's nothing more validating in some ways than winning through revenue. Like when somebody is willing to pay you for it, that's like, that's good juice. So like that is also motivating to me. Yeah. Okay, so let's laser into the thing at play currently.

1:46:44We'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. You know, be a great person. Be the person you want to be, obviously. 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 it's like, do those early employees, they'd 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.

1:47:26So 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 know but you can but you can do it with honor you know you can look everybody in the eye and talk about the trade-offs you made yeah did you in fact get to step away and take some version of what they would call a quote break yeah i took the rest a little bit yeah i took like six months off basically um and think about anything at all did you just listen to metal all the time and go for walks i uh i i sat in my office quote unquote which was actually just a bathroom that we had never gotten around to renovating in this like uh in this apartment not apartment house in san francisco and um i played dark souls um because i really wanted to learn how to do that and so i played dark souls um i wrote a dnd campaign ran it for my friends um 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 um that was fantastic i built a laptop and like noodled around with my like environment you know like i played with operating systems because i love playing with operating systems so i like 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 weird you know like that was a lot and um and and i had and i had seen um 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 arch enterprises which was transformative that like the 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.

1:49:25And 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 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.

1:50:02I 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. 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 got family. You 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.

1:50:45And it's very pure and very enjoyable. you know what i learned about myself the other day uh so when people talk about the mental picture they actually see pictures in their head like you can see you can't see pictures i see nothing oh dude i'm sorry about that i'm not i mean you're missing out i believe i probably am i see i i like i i i it's like facts it's like lists of but like like i know but i remember it and i do feel fondly about it it's not like i don't feel 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 i can see various moments in my life now my son he has got and this is because my wife he's got the literal ability to look at something and see it forever oh he's got that you know whatever it's called yeah picture memory whatever photographic memory photographic memory thank Thank you.

1:51:41He 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, well, if I if I'm looking, here's my superpower, my son. Give me a side tangent here. OK, yeah. We're at the grocery store and I'm on the app and I see the product I'm trying to find. 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 like finding products on shelves in grocery stores that you've never bought before you don't know if it's big or if it's 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 all this stuff I'm like here's the thing we're in the right aisle where's it at he's like oh right there amazing so anyways but the point is is that uh i can see clearly various moments in my life like more recently me and my son's fishing i have two sons yeah and i have a daughter as well but in this moment it was just the two sons and so we were fishing i can i can clearly remember sitting back just thinking like adam don't lose this moment yeah adam adam take a picture of this moment like hold this in your mind forever all the stresses that you might have of them falling in the water or getting hooked by the fish or whatever.

1:53:07Just be there. All the dad concerns. Like just put them over there, right? And just take a breath and just calm down. Yeah. Because it should be calm anyways. Why should I be stressed? And we're fishing. We're fishing. We're going 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 up the water. I can see the stream where it sat and I can see my two sons just like being silly. Yeah, I can't. 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.

1:53:38So like, like when I, when I hear that, what I translate that to is how it felt in that moment. And like, I know exactly how it felt to hold my daughter's hand while I walked her to work every day. I know exactly how to school every day. I know exactly how it felt when like she was born and like I held her for the first, like, you know, like I don't, I can't see the picture. I can, I have the facts of the picture, but I can't see, i can't see it in my head but i can feel it um like it was happening right now so yeah yeah anyway weird 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 um i mean i have the feeling which i think is you know to me it's enough it is enough it is enough um 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 i think it's normal that people have that yeah there's a lot of people who don't have it i don't know what the phenomenon is that of people who do and don't have it 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 you know i'm like oh okay okay yeah anyway well i 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 parts of the business yes i mean some of that startup process yeah i was system initiative it was uh so we're with three founders um me uh mihir lupinacci and alex etier and um 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.

1:55:33Like 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 like 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? You know, like over five years, probably. In that, like, if, you know, if you tell people how great something is, and then five years later, it shows up, they're like, you know, you kind of missed your shot at like capturing their attention.

1:56:22a lot yeah you know system initiative we launched it as open source and had like you've been able to download it and try it and do stuff with it for a while and people have been um i think the but now it's kind of in the in the shape where like the fullness of the experience is compressing in a way that like you'll be able to use it and it feels good and it's like 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 so complicated you know in terms of funding the business like this the only real struggle there is that five years is a freaking eternity in startup land um and so you know you you have to and 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 um you just didn't really know when you were going to get it wrong because no one had ever built it that way before so you're like, that won't work.

1:57:21That won't work. And you just don't know until you're right at the end. And then you're like, here's another like 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, you know, like they're in um that said it's got to 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 you know like it's super cool and how it works is super different and so those things together i think is enough um to to carry it into the market in the way that it needs to and again you know as a professional that's my job like my job is to what i do is i take venture capital money and i try to build the best businesses I can build from it.

1:58:18And one of the ways you build the best business and 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. You know, you got to deliver on that. And so I think we're, we're delivering on it. Timing is key, right? Timing is key in, in any launch. Yeah, it makes a difference. Timing is key. You have a history of the timing with Chef. Chef had particularly good timing, I think. You know, like the market was really ready for it. I think the market's really ready for stuff like System Initiative 2.

1:58:52I think, you know, when you look at market timing and you think about like, it's 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. You know, it can't tell you what to build, right?

1:59:35It doesn't tell you how to solve that problem or solve that experience, but it tells you that it's real. You know, it tells you that that experience is universal, that that problem is real, that that that moment of displeasure or or dislike is real. And that's a place where you can go build a business and exploit it. And so some of its external market timing, you know, 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 like with system initiative it's it is that failed 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 you know they're like playing dark souls and like 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.

2:00:34But in truth, it's actually just how close are you to those people, right? Like if 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, Jeff, you battled the rise of Docker and a change in the ecosystem. Yeah. 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 &B.

2:01:11We 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 be coming. Pretty high barrier to entry though. Yeah. How do you mean by that? You had to like download the source code and compile it and run it on your laptop. Yes. Yes, that's kind of what I'm getting at. It's like it's still, it's not easily accessible by everybody. I can't go and, you know, free tier it today. But you will be able to soon. Yeah. Okay. Do you, do you see any looming dockers out there to system initiative?

2:01:50I mean, no, if I could see them, they're not a Docker. Like the thing about Docker is that nobody saw Docker and then Docker happened and everybody was like, Docker, you know, like it was a, that was a, that was an avalanche of, of like a real sea change in the experience of what was possible. For the better, right? Would you agree with for the better? Yes. I would agree Docker was for the better. 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 you know, I'm alone pretty much in my feelings on that. But that could be because I'm a grognard.

2:02:27You know what I mean? Like 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 like you'd be insane to try to do what I'm doing because it would also take you five years even having prior art like you don't really have prior art like the source code is not enough to understand how it works or why like you have to like that's knowledge that like the people who've worked on system initiative have but the market doesn't have that knowledge and 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 like it is fundamentally a different approach to solving these problems and and that means that the experience of solving them is also fundamentally different and so our big challenge isn't going to be um 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.

2:03:41Like it's the way the people who've used it so far want to do their work now. Like, and, but will everybody else love it? I don't know. Um, and I can't know until I put it in their hands and make it easy. And in a minute, you know, 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 I don't, 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, you know, for sure. It was still the best thing I could build. It was still the best thing I could imagine.

2:04:12It 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 like, you know, 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. And so, you know, the challenge for system initiative is that it's not, um, it's not, is there some other technology that will conquer me? Like 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.

2:04:57I think it was John Osball, is that right? Yeah, sure. I think it was his last name or not. That's his last name, yeah. Okay, I thought so. I'm just trying to, did I get the name right? Yeah. and now you have this rise of platform engineering is that does system initiative dovetail and play well with this change of C 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 or 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 like what system initiative is good at is like, 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.

2:05:45And like, it's dramatic and it's much easier to extend to do interesting, complicated things. So that's gonna, as a foundational technology, people can use to build what they need to build to solve their problems. It's great. You know, platform engineering is a marketing response and a technology response to the same fundamental problems the system initiative looks at. You know, you look at that same problem that says DevOps teams, they're not working as well as you hope 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?

2:06:20And 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're going to need a developer portal. 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. And so, but now they're like, hey, what if that was the answer? And 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.

2:07:06That'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 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 uh it's cool to have a portal and like you can make a lot of money having portals you know like uh 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 um and they made billions of dollars and now nobody talks about cloud foundry so you know we'll see what happens my bet good name though i like the name incredible name great technology great people awesome name but bad bet and like i think uh i mean not a bad bet they made so much more money than chef did so just so we're clear it's super worked out for them so why are we listening to me but like as a technology i just i think uh 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 to the way we've stitched all the different technologies together it's not that one technology sucks.

2:08:36It'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 like those platform engineering stories are essentially stories about how we surface the stitching. Right. And I just don't, I don't believe that that's going to change the outcome at all. I think it's like changing from car, like, you know, like when cars moved from having a key that you put in the stem and the ignition, you turn the ignition to having a button that said start that didn't like change my life you know like 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 like your wrist is uh probably feeling it though i mean and for the positive versus negative i guess you know like 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 okay and you know i just i 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 palumi of course it stitches together this of course it talks to this under you know all that stuff it all it all has a way that it works it has a way that you manage it and you can't really escape it.

2:09:55And it defines the outcomes in a very real way, both culturally and technically. And so, you know, I think that's, that's my, that's my answer. And it's not, 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. You know, like if you just, if you just sit quietly and ask yourself like, okay, if I had a better portal over the exact same technology, 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. You know, for the person who just wants one, it's probably faster to get one.

2:10:33And once I have one, what's it do? Oh, the same before I had a button. Eh, like better to have a button than not a button. That's for real. But like, did it change the game of what happened? No. Outcomes 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 they're like 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 i lose my when when it turns out that my marketing message about second wave of devops or whatever is bad.

2:11:19And 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, what have been? And the problem with everybody else's platform engineering is the way they fundamentally build that technology. What a bunch of goobers. And like, that's because I'm playing to win. Yeah. Like 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 like it's not the train i want to be on but i will you know i'm in i'm down for whatever um i just want to win last question i'll let you go to your extensive important fun day that you have ahead beyond this podcast of multiple hours at this point yeah you're gonna have to edit it uh lightly we'll lightly edit it yeah honestly i think it's all good stuff and i'm very happy with the conversation um so you've alluded to fall right you're in you're in private beta now you said slide in your dms yeah 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 right what is what is just over the horizon you mentioned fall yeah what can you mention here for the first time ever or at at least tease for the first time ever.

2:12:45So 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 configures, like 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 like, for example, there's a, you push a button And then you can create, you know, if you had, let's say you needed to automate your CDN and we don't support that yet, or you have your own application has like a deployment mechanism that's custom.

2:13:24You 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, you know, are what actions you would take. So you want to deploy action. 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 would work or not.

2:14:02So like, 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 that's a qualification that we wrote for the IAM rule. So when you're 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 um it tells you you know 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 um 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 like because the tooling has been the tooling now for a while it hasn't been the most creative work to like do devops stuff because mostly what you're doing is like oh i'm writing more terraform how long i'm writing terraformal five years you know doing what i do get ops doing get ups you know and suddenly there's this thing that's very different works in a very different way and it's fun and so i think people are going to have a lot of fun like writing stuff in system initiative and making it do things and then sharing it with each other.

2:15:31And I think that that's, what's going to propel it into the, into the world. It's not because like system initiative alone, it's going to build all those abstractions. It's because you can build whatever you want with this fun machine I made you. And so like, we made you this really fun machine for building automation that has this like really interactive loop of programming it that like, it's fun to program and like, you're going to come program it. And so people are going to look at it at first and they're going to be like, oh, this is, you know, whatever. It's visual design for architecture stuff.

2:16:01And 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 like incredible way to program their own machines. I think they're going to go nuts programming the machine. Would you think that these shareable, contributable, programmable things that you'd mentioned to 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?

2:16:35Is that a good comparison? Yeah, kind of. Because that's shareable. So I can go grab a Docker Compose file. Yeah. As long as I have Docker on my machine, I can run that. I can Docker Compose off dash D and off to the races. Yeah, this is more like, I'm going to go again with the Wayback Machine, but like, it's more like Lisp, where there's like 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.

2:17:10And you were like, and now it did new things. It's more like that. so like the the what the unit of sharing because what 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 and like it's just a really different it's just a really different way of thinking about it so like they're shareable in the same way that maybe like a compose file is but to the user like 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 like input and output sockets and it's got properties and it like does cool things so like that's pretty it's pretty it's it is it is similar and 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 know 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.

2:18:10And then you could contribute that back in a single seamless loop, like 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? And like, you can, so like, it becomes this really interesting programming system. And like, 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, it's so much easier to model infrastructure and to like, and to see what you've done when you're finished, like then looking at like a Terraform repository.

2:18:50If you've ever like 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, uh, and that's where it becomes the power tool that actually has enough potential to change how we do the work broadly.

2:19:20Because if it couldn't do that, then, then my ambitions are too low. You know what I mean? Um, like I want to change the game. I don't want to just like, 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, I don't know if I'll win. back to being a professional but behold i'm giving it you know everything you got but i'm bringing the heat you know and like bringing the heat we'll see you know sometimes you bring the heat and you lose but i don't think i'm gonna i think i'm gonna i think i'm gonna win but we'll see i don't know we're all 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 all right Right.

2:20:03Well, systeminit.com is where you're planting 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, if you want to, if you, you can send me an email. I'm adam at systeminit.com. It's pretty easy to guess. So like, if you want to try it out on the SaaS platform, like, and you got to the end of this incredible podcast, like you deserve it. Like, feel free. This is your prize. Yes. Adam's giving away. Slide all in. access to the to the dms yeah and the private beta yeah or adam hk on twitter or x if that's still a thing you use but like you know you can you can you can totally just come and i will i will hook you up just tell me about the changelog very cool all right adam thank you so much man it's been fun thank you adam so fun what an epic show now full-length video on youtube enjoy it youtube.com slash changelog y 'all know adam is one of my most favorite people out there we love his opinions.

2:21:02Well, we kind of love his opinions. We accept his opinions. Let's just say, but seriously, we love Adam. We think he's the best. And it's almost time to check back in on System Initiative. But until then, enjoy this epic full-length show deep into Adam's history, deep into Chef World, and deep into all the things System Initiative. Big thanks to our friends at Fly for supporting us, being our partners, being an amazing host. Check them out at fly.io. And to Breakmaster cylinder those beats are banging all of our awesome music is by the mysterious break master cylinder and we're so thankful okay that's it the show's done we'll see you on friday

2:22:09Thank you.