The Stack Overflow Podcast

Moving from CEO back to IC: A chat with Mitchell Hashimoto on his love for code

Episode Summary

Today's episode is a fascinating discussion with Mitchell Hashimoto, co-founder of HashiCorp, who recently returned to the role of independent contributor after stints as both CEO and CTO. We talk about his journey learning to write software, how he came up with the idea for Terraform, and why he prefers slinging code to executive roles.

Episode Notes

Neopets: A little-known gateway into a software career. (Nineties kids will remember.)

Among the products Mitchell helped build at Hashicorp: Terraform, Vagrant, and Vault.

Not many C-level execs return to IC roles, but you might be surprised how many managers move back to being individual contributors.

Follow Mitchell on Twitter here.

Episode Transcription

Mitchell Hashimoto One thing I always think about is, and a good way to identify your passion or something you really care about is, I always made time for programming, like even when it probably wasn’t healthiest to do so. Like, I always made that time. I could have worked like a ten hour day without programming once and then I would program for two hours. Like, I didn’t have to, I probably shouldn’t have, but I wanted to. Because that made me happy. And I think seeing that over a long time just made me realize that that was the direction I wanted to head back towards eventually.

[intro music plays]

Ben Popper Hello everybody. Welcome back to the stack overflow podcast, a place to talk all things software and technology. I am your host, Ben Popper, Director of Content here at Stack Overflow, and I am joined today, as I often am, by my co-host Ceora Ford from Apollo GraphQL, and my new colleague Matt K, who is going to be a tech evangelist and a regular voice on the podcast. So, welcome Ceora and Matt.

Ceora Ford Hi!

Matt K Hello. Thank you so much.

BP Matt for folks who don’t know, do you want to just tell them real quick who you are?

MK Yeah, absolutely. So, I’m a software developer based out of New Zealand. I’ve been developing software for the last four years, creating blog posts and YouTube content around, kind of like soft skills, around being a software developer, and recently joined Stack Overflow to help out with the podcast and do some video stuff which is going to be really exciting, so if anyone’s listening, keep an eye on this space, there’s going to be some cool stuff happening.

BP Okay, great. So our guest today is Mitchell Hashimoto, and we were inspired to invite him on after seeing an announcement that he wrote about moving back into an IC role as an engineer. For folks who don’t know, he helped found and then run HashiCorp, which has built a lot of software products you’ve probably heard of, and we wanted to know about that whole journey, from how he learned to write software in the beginning, creating a company and helping to run it, to stepping back into a role where he’s just one of many independent contributors. So Mitchell, welcome to the Stack Overflow podcast.

Mitchell Hashimoto Thank you so much, and I love this topic, so I’m happy to talk about it.

BP So usually we kick things off, we ask folks to date themselves a little. Tell us about what got you into the world of software and writing code. I believe I saw an article, it had something to do with Neopets, which I think is going to make Ceora very happy.

CF [laughter] Wow

MH Yeah, it’s true. Neopets and young love is how I got into it I think. I had a middle school crush who played Neopets and I really wanted to impress her.

BP Yeah

MH And so I wanted to become like super rich in Neopets and I decided to learn programming because I wanted to learn how to make like bots and stuff to play Neopets for me, one, while I was at school, and two, because I had limited computer time from my parents, and that’s sort of how I started the journey I would say getting into programming.

BP See people think NFTs are new, but people have been forcing computers to do work so they can own digital artifacts since way back when.

All [laughter]

CF That’s so funny. I find that a lot of people have gotten started coding through Neopets or through Myspace. There are so many people that if you ask them their story, it’s one of those two things. 

MH A lot of designers through Myspace I find.

CF Yeah!

MH A lot more of the visual stuff because you can make your page beautiful and kind of like motivated people. That’s what I find at least.

BP Yeah. It was just open enough.

CF Yeah. You naturally fall into, like, the JavaScript and everything else and then one day you wake up and you’re a software engineer.

MH Yeah

MK It starts off with how can I put a unicorn on this and then all of the sudden, ten years later, it’s like, “Yeah, founded a company, did a whole design system thing.”

CF and MH [laughter]

BP So Mitchell I heard you mention that you had limited computer time at home. You had to convince your folks growing up that programming was going to be a good use of your time?

MH Yeah. I mean it was a little bit of that and I think, just, my parents were always big on sort of a balance and everything, and so I could go on the computer but I also played sports, and I had to read and do all of this other stuff, and hang out with friends. So they limited my computer time to force me to do the other stuff. And they didn’t know I was programming. They didn’t know what I was doing on the computer, so, it probably wasn’t until I went to college that I told them I was going to major in computer science and, they weren’t not supportive, they just didn’t super know what that was going to be. So I would say they were supportive, they were interested, they were just less sure how good of a path that is.

BP It’s like when my son tells me he’s going to be a professional video gamer. I’m like, “Don’t be ridiculous,” but on the other hand…

MH It’s becoming a real thing. 

BP People make a lot more money than I do so, just let him follow his dream.

CF Yeah. What happened in the in-between time between you doing the coding with the Neopets and you majoring in computer science in college?

MH Yeah a lot of stuff and I think that’s a somewhat important question because it’s sort of formative to what ended up happening with HashiCorp and everything. I ended up being successful at making these bots or games and I expanded to other games. The game to me became making the bots and less the game, so I found all these different games that I could make bots and other stuff for and I actually ended up starting an online business, like 25 dollars a month to get access to all my stuff, whatever I build, but they’re gonna be bots. And I did okay, I had a handful of customers that actually would pay that and I think that was my first foray into entrepreneurship and as a, by then, early high school person making a couple hundred dollars a month from this thing, that felt like unlimited money to me in high school. I was like, blown away. I was like, “This is awesome.” I like that people were using my stuff. I like that I could sort of make money doing this, and I liked the actual programming. So, that sort of led me down to just spinning up all sorts of, failed really, but all sorts of different ideas. I did like, hosted forum software for a while, I did course registration software, which was pretty successful actually. And just a bunch of random stuff, and so it was always this hybrid between my love of programming and starting businesses around it and being impactful with it, I guess.

BP For the bot business, was that in the cloud? Did you run them for people or did they download something?

MH No. This is well before I got into server-side stuff. This was like, straight-up downloaded Windows .exe’s. (6:22)

BP Yeah

CF Whoa

MK I’m really curious because now we have SquareSpace and Shopify and all these online platforms where you can just upload a digital asset and sell it infinitely scalable. I’m assuming you didn’t use a platform like that when you were selling these bots. So did you have to build out your own custom solution to be able to sell this stuff. How did that work?

MH Yeah. It’s funny you hit on that because that’s exactly how I got into the forum reselling stuff, because it felt to me like sort of this underground movement, but there was a sort of movement community that I was a part of that was taking off-the-shelf open-source forum software. At the time it was like vBulletin and phpBB and some other stuff like that, and turning that into a full-blown content management system. So, it’s all open source, sort of forking it or modding it and making it be able to do anything. So I sort of took open-source forum software, which already had a user registration system, and a moderation system, and stuff like that, and I modded it to add PayPal purchasing, so I used PayPal for everything, and subscriptions and stuff like that. So PayPal was the key to having an API for processing transactions, but I tied it together with this forum software which worked also because, if you paid, I hooked it in so you got access to member-only forums and that’s where you would find the downloads and you can talk to me or you can talk to anyone in that group and so on. And eventually, people were like “I want my own forum!”, and so that led to phase two, which is like, “I wonder if I can make a forum as a service system.”

BP Yeah. I’m not sure that I would say I ever went here but some friends of mine went on this Cracked forum (7:57) to download the AAA PC games that were coming out, and that was the kind of place where you could find people who would sell you all sorts of great software if you were willing to meet them and hang out with them a little bit.

MH Yep

MK For anyone who’s tuning in listening, Ben winked as he said “friends.”

All [laughter]

BP If you remember the Cracked forums, good on you. So yeah, let’s jump forward just a little bit in time. Talk a little bit about the founding of HashiCorp and what was it that led you to founding that particular company, and what was it like to be in an executive role really?

MH So I guess to make the precursor a little shorter as we’ve already seen how I got from Neopets to the forum software and so on, like, I think everything followed this natural path of solving my own problems and then building businesses around solutions I’ve built for my own problems. We have a little “...” there and skipped some time, but eventually one of my own problems was building repeatable dev environments, and other sort of cloud automation tooling for lack of better description right now. And, I open sourced that and I’m super honest when I say that, with that specifically, with that open source work, because this forum software I talked about, the Neopets stuff I talked about, that was never open source. But for this open source work that I did Vagrant, and Packer, and Terraform, and all the stuff that we ended up building, I had zero intention of ever starting a business or ever making any money from it. Like absolutely zero. I was in college and I thought that, at best, what this would help give me is a resume booster to help me get a job. That was where my mindset was. And what ended up happening was, I did get a job, and I did get a job thanks to some of my open source work, but as I was doing that, the open source kept getting more and more popular, and I loved working on it, I loved the open source community. I loved the whole aspect of it. But it got popular to a point where I felt that working on it, in parallel to having this career that I was building, was sort of unhealthy to my life, because I was working a typical 9-5 job with a commute going into an office, and then I would eat dinner, try to go to the gym, and then I would work on open source software from like 8pm until like 2 in the morning and then repeat, right? Go to sleep, wake up, go to work, I was basically programming for two-thirds of the day, context switching, all sorts of stuff, and I wasn’t socializing as much, I wasn’t dating, things like that. And I felt okay, but I could just recognize on my own that this isn’t sustainable or healthy. And so I sort of made this decision, it felt like a forced decision I say now, because there was no way especially then– I think there’s a lot more options now– but there was no way then to have sustainable open source, for me to work on this full time, other than to start something around it and try to figure out how to make money. And so I quit my job, started HashiCorp, and the goal was really to be able to sustainably work on these projects.

CF I actually worked at a company like that before. Where that was how things got started off. It started off as a side project that they did out of almost pure necessity for themselves and they open sourced it and it got popular and it got to a point where it was like, “I kind of need to choose between this or my actual job.” So that’s interesting.

MH Yeah, that’s definitely how it started and that manifested itself in many ways early on in the company just as we tried to figure out, “How are we going to be a business?” Because most businesses start with a business plan, and we started with a successful project, but no business plan whatsoever.

CF Yeah.

BP Right. 

MK I’m really curious, Mitchell. When you made the decision to go full-time was there anything going through your mind of, “I’m taking a huge financial risk quitting this career path and moving to something that doesn’t even have a business plan yet,” and I’m assuming wasn’t making any revenue because it was open source. So what was going through your head at that kind of inflection point, where you were like, “Uh-oh, we need to start making money and getting things going.”

MH Totally. Yes to all of that. So, prior to even quitting I was really torn what I wanted to do, so I asked friends and family. And all my friends were pretty much unanimous that I should do this, but they’re bigger risk takers. I think the really important person I went to was my dad, in particular, because he was always someone who is really really careful and always had an opinion on what I should do. So I went to him and told him the whole situation, and I was just blown away, because he told me, like no hesitation, he was like, “Quit your job and start that as soon as you can.” And it was so uncharacteristic of him that it gave me a lot of confidence, being like, “If he has that kind of confidence then this must be something I should try to do.” And I think his point of view was just like, at the stage I was in my life, it was fairly low risk. You know, startups in general are high risk but hopefully I could just find another job. Engineering in some ways is really privileged in that way, so that was the hope. And that’s when I got started, and after we got started, the second part of your question there is making money. When Armon and I started HashiCorp we weren’t sure yet if this was going to be a venture-backed high-growth business. We weren’t sure if that was the path we wanted to take. So the initial path we did end up taking was a lot of contract work to help pay the bills, and we weren’t paying ourselves much, but just to cover rent and cover food, like really basic stuff. Otherwise it was coming out of savings. But we did get a lot of contract work, and the first thing I ever started working on was a commercial plug-in for Vagrant which we ended up selling, which did end up ultimately sustaining the first few employees of the company for years.

CF Oh, wow.

BP So you were sort of like a consultancy built around the open-source products that you had helped create?

MH Yeah. Initially the idea was, we’ll do that and use that to fund future products and I think what we ultimately realized was the ideas we had for the products we’d build, and the number of engineers that it would require doing this in a sustainable way forever would take decades. And so we looked to venture capital as a way to change the mission to be a much bigger mission, and then also to highly accelerate what we were trying to do.

CF I’m wondering what was going through your head as the company grows and you start to get further and further away from the typical software engineer workflow of coding and fixing problems and all that kind of stuff.

MH I think that’s perfect because I was naive, or so young mentally in doing this, I had never done a startup before, never been a founder of a venture-backed startup before. So I didn’t really know what to expect. My original thought was I was so passionate about building these tools, I would start this company, and I would be able to spend all my time building these tools, and that couldn’t have been farther from the truth in the reality of that. One thing I quickly realized was, and I tell new founders this all the time, when you start a company around your passion, it’s not enabling you to work on that passion, it’s enabling you to enable others to work on that passion, and just realize that dream or that vision. So you don’t really get to be hands-on. I would say I was hands-on as much as I could, I fought it for a long time, for the first year to three years, depending on how activity ebbed and flowed. But I was splitting my time so much with the managerial duties and executive duties as much as you could call someone an executive at that stage, but it was like financial management, fundraising plans, ensuring growth, thinking big picture how we’re going to commercialize, thinking about the next X hires that we have to hire, things like that. I was spending a lot of my time doing all that. So, it settled in really quickly. I think within the first 18 months I was programming as much as I could, but probably working very long hours to do other stuff too.

MK So this is something that is near and dear to my heart, where I’ve stepped away from a very technical role into something that is less technical. What was going through your head as you realized you’ve become further and further from a contributor? Did you find that you were worried about your technical skills stalling a little bit, and what were you trying to do to manage that over the time before you eventually went to a CTO role?

MH One thing I don’t want people to think is that I hated not programming, or I hated the jobs associated that weren’t programming. I didn’t dislike those jobs and I found being a manager really rewarding in a lot of ways, and I loved helping people grow and being a good manager, most times hopefully, a good manager of sorts. But, what I realized was that my passion really was programming, like, the thing that drove me was really programming. So while I found the management stuff interesting and fulfilling in certain ways, it was taking away from this thing that gave me the most happiness of everything that I did. So, I wasn’t really worried about losing skills or anything because one thing I always think about is, and a good way to identify your passion or something you really care about, is I always made time for programming. Like, even when it wasn’t healthiest to do so, I always made that time. I could have worked a ten hour day without programming once and then I would program for two hours. I didn’t have to, I probably shouldn’t have, but I wanted to because that made me happy. And I think seeing that over a long time just made me realize that that was the direction I wanted to head back towards eventually.

BP So yeah, how did you devise first a strategy of going back to CTO, talk a little about what that was like, and then you took a real leap, my coworkers made me promise to ask, what’s it like to be an IC when you were formerly the boss? Do people really treat you like an IC? So let’s start at CTO and then we’ll take it from there.

MH So yeah, the CTO thing happened probably three or four years into the company. I don’t fully remember the exact timing, but it was three or four years into the company and, that was really a realization of me actually actively disliking the CEO role. The executive team building the financial planning, fundraising all that sort of stuff. I joke that I started to realize being a CEO is a real job.

All [laughter]

MH I think prior to that I thought it was just someone that sat behind a desk and like, reaped the rewards or something, and I started to realize how bad of a job being a CEO is. I’m so shocked whenever I meet someone who likes being a CEO. I’m like, “How is this possible?” But, I started to figure that out, and I thought my point of view is one, I didn’t like that, and two, I had an investor, someone on our board, who, they never pressured us, me and Armon, to hire a CEO or anything, it was totally our decision. But one thing he told us was startups have a 90 plus percent failure rate and so, for an investor to invest in a startup, it’s because they think they’ve identified some sort of trait that could help beat those odds. And for us, that trait was always our engineering vision, and our engineering ability. So, me spending time being a CEO was putting us into the odds of the 90 percent. It wasn’t giving us the advantage we had to beat that 90 percent. And so, he just made me think, if this isn’t something you really want to be passionate about, do what makes you happy and do what will give the company the best chance for success, and me and Armon both thought that was being engineering leaders, not necessarily handling keyboards, but engineering leaders, rather than the CEO. So that’s what really motivated us to pursue the CEO. Another way we put it is, I think we’re capable of learning to be a CEO, but we would make mistakes. We wanted to hire someone who had already made the mistakes and knew what to do, while we wouldn’t make the mistakes and knew what to do on the engineering side, so best chance for success. 

CF I’m sure now you’re really appreciative of the investor who pulled you to the side and told you that. I have moments now where I think back to moments where people said things like that to me, and I was like, “Wow, I’m so glad I listened and that they were honest,” you know, because it helped me to make better decisions career-wise and all that kind of good stuff.

MH Yeah, I think similar to how my dad encouraged me to really start it, I think it was this investor who really showed me it was okay if I didn’t want to be CEO. I think in these highly uncertain times, having that affirmation that something you want to do is okay, and something that’s atypical is okay, because founders stepping down, me and Armon both stepping down, to bring in an outside CEO as early as we did was not typical, and could be construed really badly, and things like that. There was a lot of risk associated with it as well. So, it was scary, and having someone saying, “It’s okay, we’ll always back you,” and things like that was really helpful. 

MK I have two real quick questions. First of all, who was the first person, the first brave soul, to decline one of your poll requests (20:20) and do they have a little plaque in the office somewhere?

All [laughter]

MH I don’t know who that is. I think, and this will get towards what you said earlier about being an IC, about being an ex-founder, I think that from the beginning we had a fairly respectful culture around PR as an intellectual honesty. So, I don’t know when that was, but I don’t think it was a big deal.

CF That’s good.

BP You did CTO for a while, was it just a desire as you said, you realized actually hands-on programming is where your passion really lies, it’s something that you’re drawn to even when it's unhealthy. I can relate to that, I’ve been doing Jiu-Jitsu and I’m pushing 40 and I keep getting injured, but I keep going back, and it’s like, “Why am I doing this?”, and it’s like “Well, I guess I must really like it.” But yeah, CTO to IC what made you decide to make that jump, and getting back in and actually writing code every day, what’s that experience been like? Especially having left it for so many years and then coming back to a different toolset maybe?

MH Yeah, I mean it was not as easy or obvious as the CEO to CTO role, because I liked being a CTO. Whereas I actively disliked the CEO job description, I liked the CTO job description. I got it and I thought I was not bad at it, and yeah, it was fun, but it was a relative thing again, where programming was way more fun and fulfilling for me. So for the CTO to IC switch I didn’t even think about it for a number of years, very happy being the co-CTO, and me and Armon found a really nice split because we were co-CTOs, so we found a really nice split in responsibilities naturally that I think made us both really happy in what we did. I spent a little bit more time within the company and Armon spent a little bit more time external to the company as a CTO in terms of meeting with customers and stuff like that. We overlapped a lot so that’s not super fair to say but I would say a little bit on each side. I was having a good time and I was embedding on teams and actually working on either new products or risky features or something. I was still handling keyboard a bit so, I got that as well, but I think eventually as the company kept growing, the job description changes a little bit, and as we started to hire more VPs and introduce senior directors and directors, my depth away from the actual engineers was growing, and it became much more of a headcount planning, financial planning, visioning, like long-term visioning type of role, and I wanted to get a little closer back to the actual solving a specific problem, and at the same time, we had grown to so many more people, and so many more products, and so I realized the stuff I was doing as the CTO had to be done, but it would take all my time. Like, I couldn’t program anymore, I had to get rid of that part of it because it was really important to do. So I had this fork in the road, like, do I keep doing this thing, which I don’t dislike, or is there a way to get back to programming that I know I absolutely love? And I decided to talk to Armond and Dave, who is our CEO. We probably started talking about it three or four years ago but just started talking about what kind of path that would take and if that’s even possible. 

CF I actually really enjoy your story because I’m just getting started out in developer advocacy and I think a lot about the career trajectory of someone in an engineering role or someone in a role like mine, and I always think that the typical way that it goes is like, say you’re a developer and then you become a manager, director, eventually VP, whatever. And I’m always like, “I wouldn’t mind trying out something managerial within the next few years or so.” But I’m always thinking to myself, “What if I find out that I actually enjoy being an IC better?” Do people even make the reverse transition going back to that? So it’s kind of cool to know that someone jumped from CTO to IC, because if someone can do that then I definitely can go back to being an IC from whatever I become in the future.

MH Yeah and I want to add, and it heavily depends on the company culture, I’m sure. Some people when I made this transition said, “Only a founder could have done this, because they have the political power to force this to happen.” But, I think it really depends on the company. But I want to be clear that at HashiCorp, we’ve had many managers become ICs and vice-versa. I wasn’t the first to do it by any means, and more have done it since I’ve done it, and the reverse is true. So it’s very possible, I’m sure it’s very difficult in some companies, but it’s very possible. 

BP It was interesting to hear how you describe how as it grows the CTO role just becomes CEO of the tech department and you’re back to that, sort of, high-level logistical planning and not really getting hands-on.

MH Very true.

BP So I guess yeah, before we go, I wanted to ask just a few questions about some of the products. So Terraform was one of the products you had started to create before forming HashiCorp but then became one of the products internally. Is that right?

MH Kind of. So Terraform, I had written down the idea. I wrote down the idea for Terraform in college, I actually blogged about it on Tumblr, like, gave the idea away on Tumblr.

CF Whoa.

MH Yes, in 2011 or something, I have the blog post still. I didn’t put it on GitHub (25:37). It was like, the day after cloud formation came out, or something, I wrote this blog which like, “Cloud formation is great, but I want to see this instead.” And it was just the blueprint for Terraform and no one really built it and then it became a real problem for me and so I started prototyping it, at previous jobs and stuff and then ultimately I threw those away and then rebuilt it at HashiCorp in 2013 or 2014, after the company was founded. 

BP I guess what is so fascinating about that to me, and again, I’m not a programmer myself, but I have a lot of these conversations, is just how often now the idea of infrastructure as code comes up in these conversations, and, how much of the work has moved into the world of clouds and containers and microservices. From your perspective, having had that idea in 2013, and now looking at the world now, what do you think about the way infrastructure as code turned out, and looking forward five years from now, what would you want to build so that developers can make the most of this new approach to crafting whole organizations essentially, crafting code bases?

MH In some ways I’m really pleased and in other ways I’m not surprised, whether if it was me or if it was someone else, I just thought back to 2012, I just thought it was so obvious that codifying things was vastly superior in every way to doing things clicking around or imperatively or word of mouth or whatever it was. So the fact that infrastructure as code generally, with Terraform, but also with stuff like Kubernetes and non-HashiCorp products, that the fact that that took off is relieving and not a surprise to me. The right choice won in my view, in terms of paradigm not tool. Not saying Terraform was the right tool, but the actual paradigm was right. So I’m really happy. I think that going forward, the way I personally view things is, humans and engineers go towards less friction. How do you make things easier? They like complexity, so it might be easier or complex, but how do you make things easier? I think there’s a variety of things right now that just still feel too difficult, and I’m like, “This has to be simplified in some way, and automated in some way.” So, I don’t know any specific thing, I’m not going to try to predict some specific thing, but I think big picture it’s just going to move towards more automation, more layer interoperability and things like that. That’s what I would do anyways, and that’s how I approach every problem. I’m like, “Why does this suck, and how do I make it suck less?” It’s literally the question I ask with things.

CF Yeah. I think I’ve seen that happening with a couple companies that we’ve talked to on the podcast too, where they’re creating products that the whole purpose is to make the process with infrastructure or other things less friction-y. I’m just going to make up that word. So, make it more frictionless I think is the better way to say it.

MH Definitely.

MK The web is already quite a complex beast as it is, so if there are any ways that we can kind of simplify and automate and make sure that people aren’t getting pinged at 3 o’clock in the morning to go on a call to deal with a problem, the better.

All [laughter]

CF Absolutely.

BP Spoken from experience, Matt?

MK [laughter] Yeah.

BP I guess the question on every developer’s mind who’s listening is, what is the tension like, having had the founder title and the CEO and that executive role and power, but then going back to IC. If your manager tells you he needs something on deadline and you don’t think it can be done, or needs you to work over the weekend, how do you respond to that as an IC now?

MH I think an important part of that is setting the culture from the beginning, and I think from the beginning we set the culture that I’ve been pretty respectful of processes and things like that. It was different when I was the boss, I would say “No” at certain times. But being an IC now I make it really clear going into a team, most people probably don’t need to do this, but I make it really clear going into a team, “You’re the manager. You tell me the process. We’re going to use this tool for this, we’re going to use that tool for this, and I’m going to do it, because I’m just a member of the team.” So, at first it’s a little bit scary, I would say. It would be interesting to ask my manager what he thinks, but they eventually understand that I mean it, and I act by my words and live them. And then it becomes really good, like I got a message yesterday that was like, “Hey, I need this thing done by tomorrow.” Like, a surprise. “Can you get this done by tomorrow?” And I was like, “Sure.” And I did. So, stuff like that. And same with my team members is understanding they can reject my PRs, understanding they could bring alternate ideas up to the table. I think it’s all really good. I’m still obviously pinged for advisory stuff for senior level things, but one thing I always tell people is, it’s very much like a pool thing (30:14) like, senior level leadership will ask me questions or input about a specific thing, and I’ll give it to them, but I don’t know things anymore. I’m in the same channels as you, I’m not in the executive channel anymore, I’m not on the executive mailing list, I don’t talk to HR, I don’t know what comp rates are anymore. I’m not part of those discussions. So someone can tell me something and there’s nothing I could act on specifically. I suppose, some people say I could pull some power card and call Armon up and be like, “This person was terrible!”, or something. I guess, but I would hope that people who work at HashiCorp realize that’s so antithetical to our culture, that I would never do something like that, and that’s the best I could do. 

BP I would have a hard time writing a performance review, maybe, of my former CEO, but also, you chose to go back to IC so clearly you don’t want a promotion, if you’re happy as a clam there you can stay there as long as you like.

CF [laughter]

MH I’m not, yeah. I’m happy fixed where I am.

BP Taking servant leadership to a new level. I appreciate it. 

MH [laughter]

MK You’ve done the grind where you’ve started a company from scratch, you’ve led it to great success and now you’re kind of at an IC level again. Do you ever get that itch to start over and take something completely new, start that whole journey again, do it now with the experiences that you’ve had with HashiCorp, and try and, maybe not do it better, but try and relive that whole journey?

MH Yeah, I mean being an IC again has made me realize that I still have a ton of ideas and I’m still very, in my mind, creative and with things that aren’t HashiCorp related at all, and so I think, if I wasn’t at HashiCorp I think I would probably do something again. But, I don’t think I would ever do a high-growth venture-backed company ever again. It’s just like, I know the steps you have to go through and I wouldn’t want to go through those again. But when I think about it, smaller software studios or indie stuff, I would do that. But I don’t think I would do like a 2000-person company again, or try to. 

MK You’ve mentioned that you built the product, you did the CEO and founder thing. For other founders who might be listening who are technical but don’t want to go through the rigamarole and stress and strife of being a CEO, do you think that’s still a valid path for them to be a founder, but not take on that responsibility?

MH I think you have to take it on for a period of time. I think you have to build the machine, is the way I put it, and a mistake a lot of founders make, is they make themselves a critical part of the machine, and I think my advice would be, and this is what I always ask myself explicitly on like a quarterly basis, I would be like, “How do I build this company where they don’t need me?” And I think that that’s the question you have to ask. You know, “Don’t give a person a fish, teach a person to fish,” that sort of thing, you’ve got to get those skills out so that when you hire the CEO or hire your replacement, you know they’ll hopefully make similar thought processes as you in terms of decision making, because that’s ultimately what a company is, is like a unified mission and a unified way of thinking around a problem, and so you have to define that way of thinking. I think it’s unavoidable that you have to be a senior leader for a period of time, but I think if you start from the beginning explicitly about building this autonomous, in a way, autonomous in terms of a lot of people, machine that you could also step down. 

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BP Alright everybody it is that time of the show. We are going to shout out the winner of a lifeboat badge (33:47), someone who came on Stack Overflow and helped save a question from the dustbin of eternity. Today, we will shout out Alexander Shatkin (33:59), “How to recycle an application pool using a PowerShell script.” So, if you’re curious, we have an answer for you. I am Ben Popper, the Director of Content here at Stack Overflow, you can always find me on Twitter at @BenPopper, email us, or leave us a rating and a review. It really helps. Matt, let the folks know who you are and where they can find you online.

MK Hey everyone, thanks for listening. My name is Matt. On Twitter @mattkander. Love to see you around and talk about tech. Thanks!

CF I’m Ceora Ford, I’m a developer advocate at ApolloGraphQL. You can find me on Twitter. My username there is @Ceeoreo_.

BP Mitchell, we know who you are, but tell the folks again who you are and where they can find you on the internet if you want to be found.

MH Sure! I’m the cofounder of HashiCorp, and I go by MitchellH everywhere on the internet, and I’m pretty active in responding, so feel free to ask any questions, and thanks for having me here.

BP Awesome, thanks for coming on. Alright everybody. Thanks for listening, we’ll talk to you soon. 

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