Founders Talk – Episode #57

From dropout to CEO of Sentry and taking on New Relic

with David Cramer


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David Cramer dropped out of high school AND college, but that didn’t stop him. He ended up teaching himself programming and eventually landed his first job as the webmaster of a World of Warcraft community website. What a beginning… We talked through “the rough slog” period of Sentry and how David powered through to traction and enough profit for him and his partner to go full time, raise three rounds of funding, and take on New Relic.



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David, let’s start with dropping out of high school, and then later on dropping out of college, as well… Were you bored? Why did this make sense to you? What was going through your head when you did? Maybe let’s start with high school first, because that was the first event… But why? What was your frame of mind then?

I’m from the Midwest, and I think schools vary; I don’t know if ours was good or bad, but it certainly wasn’t a school of excellence. I think some kids have this rebellious nature, and I was never good about doing homework, and things… I generally got good grades, but it would be like if I did tests, I scored really well, or in class work I did really well, or if I actually sat down and did the homework, it would be fine. Half the time I’d do it in the morning, before class, or something, but a lot of times I’d get weak grades just because I didn’t turn in homework.

Where I grew up, school was like one through five is elementary, and then six through nine is middle school, and then high school. In the eighth grade, so the year before going to high school, I took an algebra class, and I remember that – basically, you got an A in this class if you turned in homework; that’s what you had to do.

And I think I got like a C maybe, just to give you an idea… The class was extremely easy for me, and I was always really good at simple math, which probably explains how I got into software. Super, super-easy class, but then I went into the freshmen year of high school and they suggested I take algebra again, because I did poorly… And algebra was an elective class in eighth grade; it was one of the few above the standard electives you could take. Anyway, so I took algebra again and it was awful at this point. I was already bored doing it the first time, and now the second time I’m just like “This is the easiest thing I could possibly be doing.”

[04:10] Then on the counter side I took biology, which was also an elective over Life Science, or something. Biology was actually a little bit difficult for me. Anyway, I wasn’t super-engaged, and there’s always these things where I felt like the system wasn’t good, so I would try to do things my own way, and that obviously doesn’t work in a good curriculum.

Another example was we had this – I forget what it was called, but it was like this computer technology elective class in high school, and the way it worked is you would get a number of credits for completing a unit of work. A unit of work might be like Introduction to Excel, or something super-easy… So I knew general computer stuff fairly well at that point. I was writing some scripts on the internet, like PHP and stuff, so I went through and I did all of the units of work I needed for all these easy things; it was like Excel, Word… I don’t even remember what else… FrontPage, if you remember that…

All these little courses… And then there was an introduction to C++. I did that one, and I was already done with however many credits you needed for this class. I did the C++, and I just did that for the rest of the semester, I guess, which was probably like at least a quarter, and I went through half of the book or more, and you were only supposed to do the first chapter.

I got a very bad grade. I didn’t fail the class, but I got a D or something in that course for not participating… And that’s sort of like my takeaway from high school - I didn’t participate, so I got bad grades. And I convinced my parents too – you know, I as a parent would never be like this, but I convinced my parents to homeschool me the sophomore year. My parents weren’t much better than I was about being on top of my homework, and also homeschooling material – for somebody who’s not religious, the homeschooling material is not very good. It’s all generally built for Christian private schools and stuff like this; I won’t go into details there, but generally it’s more stuff that upset me about the way you learn useful skills.

So I went through that, and I probably only did half of the work, and my parents weren’t really on top of it, so I ended up at the end of that year just not continuing high school.

So it was the sophomore year then… Wow.

Yeah, the sophomore year of high school at effectively dropped out. At the end of it.

Okay, so you went through the majority, if not all of your sophomore year, and then you decided to homeschool, which would have been your junior year, right?

No, no, sorry… I went through my full freshman year.

And then I was homeschooled my sophomore year.

Okay, gotcha.

And then towards the end of that sophomore year, at that point I was like “Okay, I give up. This is awful. I’m old enough…” – I forget what the age was; it’s like 15, or something… As long as you have parent approval, you can drop out. Anyways, somehow that happened. I don’t even think there was a conversation, but it did.

Were you from a well-off family? Were your parents working? Give me an establishment of some of the home environment that makes that sort of an okay decision for parents even.

I don’t think it was an okay decision. I don’t wanna give my parents any grief, but I come from like – how would I describe it…? It’s not hill people but it’s lower working class, I would say. My mom and dad separated when I was really young, and my mom probably makes at that time $20,000 a year. We lived in a small town; the town I grew up in was only 12,000 people, to give you an idea, and we then moved to a smaller town, which was like 1,500 people. So even though it’s only $20,000 a year, that’s still like ends meet, you know… But it’s not like a wealthy family, or anything like that.

I ask you that because when I was reading some of your story, I was thinking like – aside from the dropout, very similar, and based on what you’ve just said there very similar too, because I came from a not well-off family; my dad passed away when I was really young. I was two-and-a-half when my dad passed, so I basically grew up with mom-only, and then family, of course, raised by a village kind of thing.

[08:12] But in all intents and purposes, I basically dropped out of high school, but I didn’t. I continued, I just didn’t participate. I just went through the whole thing, didn’t have the homeschooling option there, but… I didn’t do very well, and I’m still where I’m at today, in spite of that. So that’s kind of what I was trying to unravel, rather than shaming your parents. I was trying to figure out like where did you come from, kind of thing.

Yeah, yeah. It was very much they were working all the time, and they had their own – not goals so much, but their own requirements of life, so I sort of get it on one had… But yeah, it was very much like a working class family, most of the time just raised by my mom, actually. But yeah, it was certainly an interesting path to get here.

Sophomore year, you’re homeschooled, that didn’t really work out… What happened to junior and senior?

I don’t actually remember what the transition was like. I think I’m just like “I don’t wanna do this anymore” and it was sort of a mutual agreement or something, that like “Okay, we’re not gonna be able to convince you to do it. You’re very strongly opinionated, so we’ll just stop.” I literally don’t remember anything other than that, like if there was a process I had to go through, or something… Whatever it is, my parents or my mom handled it.

Did you feel weird around friends, not participating in dances, and all these typical common things that people do with high school engagements, like sports, and stuff…?

Yeah, I think for probably a year or two I did. Year two - I actually had like not plan in life at this point. So year two I’m sort of like “Okay, this is a little bit weird… Every so often I’d see some of my classmates that I’m not friends with–” I still had a couple friends that I was close with from school, but I would see others, and it would always be like this awkward thing, like “Oh, we thought maybe you moved away, or something…” It’s like, “Oh… No… You know…” But otherwise I didn’t really think that much of it.

I’d spend a lot of time on the internet at this point, just building little things, interacting a lot… I got into IRC, so I met a lot of interesting folks, whether it was technology or other hobbies online… So that sort of consumed me at that age as well.

As you were saying that, I was just thinking like – “Raised by the internet” came to mind… Do you think that might be somewhat accurate?

Yeah, I don’t know, maybe… I would say I learned so much by having access to the internet, and it’s actually one of the reasons I care so deeply about technologies, because I was able to just do so much. The internet was very open at that time. Not that it’s not open today, but it’s a very different kind of internet these days.

It was greenfield. Everything was new, everyone was still discovering, so there were no really established ways of doing things.

Yeah, exactly.

There were no conglomerates like Facebook running and ruling… Not that they – sorry, they do; they definitely do. They run and rule. But it was like that quite then. Everyone was still trying to get theirs.

Yeah, I think a lot about this, because you know, we recently went through GDPR, and one of the reasons – I was doing an interview with (I think it was) a local newspaper here in San Francisco… This was like a PR influence newspaper, so we did some prep to talk about what I’m even gonna engage with, and one of the things that came to mind for me was like, I love the internet and I love that I was able to build Sentry; I love that I was able to build my early websites and stuff, and get them off the ground… And then GDPR is just an example of something that’s come along that actually makes it a lot harder for individuals to build something. And these big conglomerates actually make it a lot harder for anybody to build something, and our technology makes it a lot harder for anybody to build something.

We just create these new barriers to entry for something that was originally very easy to get up and running on. So to me, that’s kind of like – I love what the internet used to be, I still love the internet, but it’s a very different place these days.

[11:53] Definitely. Definitely. Well, how much does dropping out of college play into your story? We went deep into the high school portion of it, and I feel like – I don’t know, what happened there? Did you go from drop out of high school, kind of with no real plan in life, to somehow like “Okay, let’s try again. Let’s go to college”?

I was working at a Burger King for (I wanna say) 1-2 years (I forget exactly how long), and at some point I got a job (I don’t remember how this happened, but I got a job) working on a website where I was supposed to produce content. It was a gaming portal. At the time, World of Warcraft was just coming out, so it wasn’t hugely popular yet, but the gaming community was already really into it. So I got a job building content for this World of Warcraft website, and originally I was supposed to be writing guides, and things like that… Instead, because I had some degree of scripting and engineering skills, I started actually trying to extract data from the game by just mining the files.

Anyways, suffice to say I grew that pretty well over the course of a year. I sort of had transitioned from doing this Burger King thing into – I don’t wanna say a prestigious job, but something that was actually more tangible and giving me more direction. Then from that, I actually joined a company called Curse, which was my first sort of real job that anybody would know what it is, doing sort of the same thing… They were this big portal for World of Warcraft mods, like add-ons, like little scripts and stuff. Eventually, we had a bunch of other properties, that were like a database for World of Warcraft where you could look up items, and things like that.

Anyway, so I joined there the lead developer, with like three other guys who were also 19 years old… So it was literally like a family of three French people, myself, and then another French guy… Which was very interesting, because they didn’t speak English well, so they made for an awkward couple years.

That was what got me out of where I grew up, and then over the course of – it was probably like 5-6 years between the time I dropped out of high school, to where I’m like “Oh, I wanna go to college now”, for no good reason, honestly, at this point. To go to college I guess I have to go graduate high school, so I went and got my GED in the summer, and I started school that fall.

I lasted like five months, and I’m like “Why am I doing this? I’m not learning anything.” On one hand it’s stressful, because I was still working full-time, I was doing remote contract consulting work at the time, so it was stressful because of that. If there was anything interesting to learn and anything that was sort of applicable, like technology, it was very easy and it didn’t feel like it was a good spend of time or money. Anyways, I ended up quitting that pretty quickly, and then backed out here to San Francisco.

So you said Midwest… Where is Midwest, for growing up, just so we can understand…? You’re now in San Francisco, but where did you start out at?

Right around Lincoln, Nebraska.

So like, United States of America, right in the center.

Yeah. So tech was easy for you… I mean, it was the easy, least path of resistance for you, essentially, and everybody learns differently, right? Everybody has this different path. Because I’m similar. I didn’t do well in high school, I went into the military the year after I graduated, I intended to go to college, didn’t feel confident enough to go, didn’t feel like it was a place for me… I just didn’t understand why you would go; I didn’t have a purpose. And then in a similar way, I found tech to be easy at some point, several years later, and I never got a degree in anything I do, or had any formal training in anything I do. Everything was like you, self-taught.

That seems to be a norm to people…? Not all the time, but it’s sort of like a normal anomaly, let’s say.

Yeah… I always tell people, especially when you’re interviewing engineering candidates - you could have somebody that comes from a great school and they could be amazing; you can have somebody that doesn’t come from a school at all, and they can be amazing. I think if you put people that have the drive to succeed and learn something, generally they have interest in it, AND you put them in a great school, you’re gonna actually create a really great success… But not everybody has the same opportunities, right? Or at least they don’t understand what those opportunities mean.

[15:56] Maybe I could have chosen to go to a CS program at some point, but I had no idea I wanted to do that. I didn’t even know what a CS program was when I was 15, let alone early 20’s. I was fascinated by building websites, and stuff. So you find a way, I think, if you’re motivated.

You said at one point in this conversation the system wasn’t good, and just given your success and the things you’ve done over the years, clearly the educational system didn’t play a huge role in your success, simply because you said the system wasn’t good… What do you think about the system today? Do you think about that at all, or do you sort of just not worry about the educational system and how there may be solutions to it, you don’t have any ideas basically?

I wanna say I have ideas. I think one day I would like to give back and see if there’s something I could do to help. Sentry, for example - we give Sentry for free to any education group. If you’re at Harvard and you wanna use it for your own programs, you should pay us money, but we’ll happily give it to all your teachers and students.

Sentry - I don’t think it’s quite as interesting for a lot of people, just because you sort of need like a production application, but it’s the easiest way I have to give back right now.

I would like to do more over time. I don’t know what the state of it is, and I know it’s drastically different in different areas. For all I know, schools around the Bay Area are great, and probably also really expensive, but Nebraska is night and day… And I would like to think that one day - I think this is a national problem - we’ll get better about education; at least we’ll start educating people for the future, not for the past, and that is like more technology education, building those trade schools earlier in school. I don’t follow a lot of the work there, but I think was really interesting, and then the work they’ve done historically around trying to get programming into curriculums, and stuff. I think that’s super-important. Some of that is biased, though; I don’t know if that fixes the core of the problem of education… I don’t know. I think it’s a very complex problem, that I generally don’t have much insight into these days.

I’m just curious because you’re a problem-solver, you obviously have had your own personal angst with the system, even trying to do homeschooling, thought college might be better for you again later on, gave it another try and that didn’t work out again… So you sort of had two tries, and not so much fails, but just disappointments in the system.

I wanna make one note on there - college actually I didn’t mind. I liked college because it treated you like an adult, and it’s like “You don’t have to show up to class. Literally, you can just do the homework and turn it in”, and things like that, which was actually quite refreshing.

For example, to give you a little bit of a deeper dive, I was going to a community college, and then I was gonna transfer to the university, so I did two quarters, because you basically book them in quarters, right? In the first quarter I did calculus, sociology and German, so nothing related to technology, other than you could say math is maybe, but… Calculus was really interesting. It was actually really hard for me, because I didn’t take college algebra, or any of the sort of the prereqs. The only reason I was able to sort of jump into calculus was because at the GED I tested – I basically tested out of math, so that calculus was the only requirement I had, which you had to take at the college level… And that actually was really taxing. Thankfully, WolframAlpha exists and was able to help me through understanding some more of the things.

So that first quarter was actually really tough, but it was interesting. I actually did very well, in grades and all there. And then the second quarter I switched to – in retrospect, this was an awful idea… I switched to computer science courses at a community college. I don’t even know why at this point. I think I just needed to pass some time.

Technically, I did learn some stuff here. I never really knew how CPUs worked before, for example… Not that I wanted to know, but I was forced to learn a few of these things. But I didn’t have to go to class, and at one point I think I did like two months’ worth of homework in like a weekend, or something… And it’s like out of one quarter, so it’s like two thirds of the homework. And I thought that was actually kind of interesting. I don’t know if that’s a good or a bad thing, but at least it allowed me to function better. So I at least think that was set up more reasonably than my earlier educational experiences.

[20:22] Let’s fast-forward a little bit and tease essentially what I feel may be the beginning of your CEO journey, although you really began back at your sophomore year, with electing to take charge of your life and do something differently… It seems like Sentry began sort of on accident, let’s say… It’s open source. You mentioned that in some of the back-channels, in conversations between you and I that Sentry was started just by scratching an itch from some sort of response to the community, in the Python community, how to log things; you open sourced it, no big deal. Does that somewhat summarize that moment?

I think that very well summarizes that moment, the no big deal part.

The “no big deal” part of it?

Yeah, it was very much no big deal. I actually did a lot of this stuff back then. Like I said, the internet was sort of – as you call it, family, to some degree. I was very, very active on the early days of social networks, which was IRC.

So I was just always answering question and talking to other people about what they’re doing. So it was like “Oh, you have a question? I’ll help you understand it in code”, or something. So for me, this was like an everyday occurrence. This was probably a little bit more in-depth than most days, but I did actually write tons and tons of little snippets like this back in the day, or what started as a snippet, at least.

So at the time when you wrote this though, I believe you were at Dropbox. Was there any concern with being related to your employer’s stuff? Did you ever have any concerns around that? I think about everybody pretty much these days who starts a startup, they tend to have a main thing, and then their side-hustle, or their accidental-project-turned-success, that kind of thing. Did you ever have any of those concerns or worries inside of Dropbox?

Actually, let me correct that a little bit. Actually, I started it right before our company. I might have been employed, I was doing contract work or something, but very disconnected from our company.

And then when I really built it, I was at a company called Disqus, which are still around, but they’re not as known these days. And I built it really for Disqus, or rather I expanded what I did drastically, or rebuilt it for Disqus. It was always open source and freely licensed, so it was safe. Then I spent a lot of time building on it in my free time, and I was very ethical about this. If Disqus needs something, I’ll do it during work hours, but if Disqus doesn’t, I’ll do it at home or on the weekend, and that’s a very common story.

Honestly, I get a lot of people that talk to me and they’re like “Hey, we admire what you’ve done with Sentry… This is how I do it.” I’m like, “That’s literally how I did it - nights and weekends.” And then when I was leaving Disqus, going to Dropbox, that’s when I had started the SaaS service, which is the business.

Going into Dropbox or a company, you do have to be careful about this. You have to make sure you’re crystal clear that “Hey, I own this thing” or like “This exists”, and stuff, just to make sure you’re all on the same page. Companies are usually fine about it, but it was still very much at that point nights and weekends, like “How do you make this run?” To some degree, you might say, you know, work/life balance, like you shouldn’t have to do that, but nothing’s free, and I sort of look at myself and I took all these sacrifices of my own personal life and my free time to achieve what I have today, and I have no regrets there. I think to some degree maybe you have to do that.

Now, you can go the traditional route and just raise a ton of money or do something else, or maybe your family can support you, but I think if you can do it in your spare time, it gives you ample opportunity to validate that it actually matters. And not everybody has the luxury to just sit down and be like “Yeah, I’ll just quit my job and I’ll work on this for six months to a year.”

So the tool is open source, it’s out there freely available, you’re doing nights and weekends, on your own, you’re building it, you’re working at Dropbox this time, and someday something happens and you’re like “Hey, this could be a business.” There’s an open source component, but then there’s also this for-profit business venture. What made you think it could be or should be, and what gave you the courage to do it?

Yeah, so I think historically I’ve always been risk-adverse, so that was actually a pretty big decision. It was a couple things, two major factors. One, we actually had a number of peers in the Django community that were like “Hey, why don’t you host this? I’d pay for it.” I’m like, “That’s cool, it’s fine. You don’t need to. It’s free, you can run it.” And then I had a couple other peers, or actually closer friends, who were like “Why don’t you actually do this/run this?” One of them actually worked at Heroku at the time, and they were like “Hey, it’s really easy to get a Heroku add-on going. You could just start it there.” I’m like, “Okay.”

That was actually around like a holiday break, and I don’t know how this works for you, but in a lot of software companies the couple weeks around Christmas nobody really gets anything done; half the people take vacation. So I actually used that time to build the SaaS service to get it off the ground. And when I did that, I convinced one of my colleagues from Disqus, who’s a designer, to really come on, sort of for the business component… You know, just because it’s better to have two people than one. And he had been helping with the open source project already anyway, with design.

Yeah, so we kicked it off there. It was really driven by demand. To me, this is actually pretty cool, because Heroku actually sponsored credits for us from the beginning, so we didn’t have to pay for hosting, day one. Actually, the person works here; our first customer works for Sentry, but day one we had a customer, and it was this person. And I think by the end of the first week we had like ten, or something… So it was really great for us. It proved that there was something there. We weren’t talking about, but…

A good feedback loop.

Yeah, yeah, for sure. The downside is like we charged them all like $7 or something, which seems like “Oh, that’s fine”, but the lesson learned is charge a lot of money if you’re gonna do this as a side project, because depending on the kind of business, at least the mental cost is gonna be extreme. So if you have lots and lots of paying customers, you have lots of customer support, potentially maybe you have to deal with server concerns, and if you have a lot more revenue coming in, you can just buy more expensive servers… Things like that. And I didn’t really think through those early on. I’m just like, how do I make this cheap to run? How do I not lose money on this, to where six months from now I’m spending a bunch of money out of pocket and I just say “You know what, this is awful; I’m gonna give up.”

So I spent a lot of time trying to keep it lean early on, and I’ve actually never put a dollar into the company, which I’m pretty proud of. The first three, three-and-a-half years of its business, it’s fully bootstrapped and profitable.

[28:14] That’s interesting… I mean, zero dollars. I guess that means you grew based on revenue. Your growth was based on your customer growth, and/or proven market value, which was what people were willing to pay you, and the profit there from that.

Yeah. The caveat is myself and my co-founder were gainfully employed by other companies, so we didn’t have to take a salary, of course… But we were able to slowly transition into taking a real salary. Early on, maybe after a couple years of doing it in our spare time, we were like “Okay, let’s pay ourselves a little bit”, so we took like $1,000/month salary per se from Sentry, which is very little in San Francisco, especially after taxes… But over time, the margins got better and better as we got more customers, to where when we did finally quit and do it full-time, we could match our salaries from our previous employers, which was a really nice, liberating, also low-risk moment, but it was a slog to get there… Lots and lots of painful nights and painful weekends, painful vacations kind of thing.

Describe that. What’s the slog with that? What’s the hard part? Is it the growth of the company? Is it establishing the product? Is it proving it fits? Because clearly, from day one you had a customer, and by the end of the week you had ten, so it wasn’t so much as a product-market fit… What was the slog?

Yeah, so I actually didn’t tell people… The first third of Sentry was like – it’s sort of like that passion, you have an open source thing, you’re just building it, it’s fun; it’s pure joy, if you like building things. You get customer feedback, you’re building new features, no cost.

Now, probably after the first year of running the SaaS business, maybe a year and a half or something, we’re suddenly getting into a point where scale became a concern… At some point we had to move off of Heroku, because the service couldn’t perform well enough on Heroku… So we had to move to other servers, had to configure all that stuff. There are (I think) three different occassions where I was traveling internationally where we had like an outage; that was pretty serious, and hard to deal with.

I specifically remember I was in the Vatican Museum in the Vatican, around Italy, and I’m sitting here on my phone with like an SSH client logging into production, clearing the celery queue because something was going wrong, and it couldn’t keep up… And this is still pretty early in the life - sorry, early customers; some of you still pay us - but I’m literally just deleting their data to some degree, because everything was on fire. And there were a lot of moments like that, where it was very stressful.

If I’m at Dropbox and there’s a serious customer support issue, or if god forbid there’s an outage, what am I supposed to do? …like, step out and be like “Hey, I have to go do my own stuff right now. Sorry, Dropbox.” So that was actually very stressful.

I had joined Dropbox because I thought it was gonna be a little bit lower stress. It was not. And I thought Sentry wouldn’t be that painful, and I ended up with two extremely demanding jobs at the same time, and that actually was sort of like a turning point for me. One of the reasons we went full-time on the project was we had to let something go. It was either let the Sentry opportunity pass, or leave our jobs.

So how did you know that Sentry was the right move? Did you and Chris sit down? What were the qualitative things that you looked at? Or you said that you were risk-adverse, so being on your own was probably the riskiest thing you could have done, right? Or I guess it depends… Or just get a different job.

Yeah, so I don’t think it’s as risky as I thought it was, because getting a different job would be easy, right? Chris had decided to leave – he was at GitHub at the time, and he had left GitHub probably six months prior to me leaving Dropbox. He was like, “Okay, maybe I’ll just work on Sentry full-time.” I’m like “Oh, that sounds great!”

[32:00] Now, caveat, it’s a little bit less great when – so my co-founder Chris, he’s a great designer, and he’s technical, so he can write JavaScript and CSS and HTML, but he doesn’t do the other stuff. So even though he’s full-time, there’s still a limitation on my time. So he went full-time and we were able to pay him a good enough salary, and then I was able to go full-time at the end of the year, when I had sort of coordinated my departure from Dropbox, and pay a well enough salary.

Another point we sort of were like, well, we could pay our bills, so it’s not a big risk. We don’t really know what we’re gonna do with it yet. When we quit our jobs, it’s wasn’t like “Yeah, three years from now we’re gonna have 10,000 customers”, or something like that. It’s like, “Yeah, this is cool… We’ve built a little business. Maybe it’s a lifestyle business, we don’t know…” It was very open-ended at that point.

Well, since you said lifestyle business, I’m curious what your thoughts are on that. Clearly, Sentry is not a lifestyle business, or now maybe it is (you can tell me, for sure, but it seems like it’s not). Was it a lifestyle business what you were trying to go for? Did you intend to get where you’re at?

I don’t think we ever intended to get anywhere along the way. At no stage was anything intentional, other than like “Yeah, I guess we’ll start this thing” and “Okay, yeah, let’s go full-time, because we sort of need to, to be sane.” Sentry is definitely not a lifestyle business these days. The turning point for me was – when we went full-time on the project, specifically when I went full-time on the project, we’d already talked to one of my friends, and now an employee of Sentry, Armin Ronacher, about like “Let’s build something… It would be great to just do things the way we want to, like open source and whatnot…”, and we didn’t know what that meant at the time.

We thought maybe we’ll build a bunch of products, or something. We didn’t realize it would just be us building Sentry into this big, giant idea. But when we did that, we also said, okay, there’s two paths we go. There’s one where we try to build this as like a normal business, that’s bootstrapped, and we compete with the market, which is very hard in technology… And even worse, we had a bunch of competitors that had sort of sprung up while we were not working on it full-time; they weren’t nearly as big as us, but they were there, they had employees, they had venture capital, so we sort of were like “Okay, if we just keep this bootstrapped, there’s a very good chance these corporate entities come in and put us out of business”, and I’m a very competitive person and I wasn’t happy about that idea…

So the alternative was we go and raise money, with the stipulation that if we raise money, we build this into the biggest thing it can possibly become, and that’s what we did. But that was a big decision point, where we all had to get on board with this idea of raising capital, and it was actually a lot harder than I thought it was gonna be. It seemed like it would be easy, because there was so much interest early on, and we made a bunch of money.

I think when we went full-time, when I left Dropbox, we had 2,000 customers, all paying, and we had about $600,000 in revenue; so we were doing fairly well, but we weren’t super wealthy. Engineers in San Francisco, say they get paid 150k a year, or something in that ballpark; we could maybe afford three salaries, maybe… And then we were growing fast enough that maybe every couple months we could afford another, but that’s still not…

It’s not growth, yeah.

Yeah… And you’re running close to the line at that point, which is always scary. You don’t have a ton of capital in the bank or anything, so the risks are – even though we could afford to pay ourselves, what happens if we lost 10% of customers one month, or something? So it’s still a little bit scary.

Let’s examine this, because that’s something I’ve thought of, too… It’s like, you start a business, it’s fun, it’s a side thing, it’s lifestyle - however you wanna describe it. It’s not so much that it’s not serious, it’s just that you didn’t have to make the choice you and Chris eventually had to make, which was the venture capital route and the reasons you said, so let’s tie that in there… But I feel like the market, if you’re gonna be in a business and you have to compete and other competitors come in, at some point the market essentially says “Are you serious or not?” and there’s a response.

[35:49] And I feel like sometimes – like you had said, you could have kept growing in the bootstrap method; your business was growing, but not at a rate at which you could on a long-term compete… So it seems like you were forced to make a choice of either remain one way, which was the bootstrap lifestyle, sort of blasé kind of way, even though it was legit and great to, say, a large injection of capital to grow and scale… That usually means – well, that is venture capital.

Yeah. I would agree, it’s a choice, like “How serious are you about this opportunity?” and that’s what we saw it as, to be clear. We were like “You know what, we built something here that clearly has traction. We have more paying customers than most businesses will ever have in this space… So why don’t we see what we can do with that?”

It was kind of one of those things where – you know, we didn’t set out to build a true business; we never did. We just like building things, but given the opportunity, why would we let it go? And I think you hit it on the head; there’s a lot of companies, small businesses in our space that do, say, JavaScript error tracking, but that’s the only thing they do, right? And they’ve got a nice little lifestyle business. But we weren’t content with that. We have a mission here, which is very much driven from me - the utmost pillar of our business objective, and that’s what we say every developer, every single developer at every single company, every single hobbyist, but every developer… And you can’t really have that as a lifestyle business. It’s just too aggressive, and it’s a very real objective.

So having been through venture capital and this market push, whether you like it or not, we’ll find that out, into this next phase of Sentry, the business Sentry; you had to take venture capital. What’s your relationship with venture capital? Is it a love/hate relationship? You seem like you had a journey to share, which everyone does, around finding capital and raising funds, and stuff like that. What is your story around whether you like it or not, the love/hate relationship?

I don’t think I really have feelings about it. I understand it a lot more now than I used to. I used to always make maybe not so nice jokes about companies who take a lot of money, and why do they even need that much capital, and all these other things. We probably all do that. I actually understand that much more deeply now, and I would probably distance myself from those kinds of things.

When we first took capital, we took a small seed round, led by a colleague who used to work at Dropbox. I think we were somewhat fortunate to have him as an investor, because he sort of understood who I was, that I’m just a builder, I don’t know anything about running a business; even though we had already built the business, it wasn’t intentional. It was very organic, grassroots. And he actually helped a lot, and still does… So that’s been very valuable. But honestly, for the first two years of raising capital, to some degree we just sort of like tricked them that we knew what we were doing, because it was growing to a reasonable degree… And they would tell you they were not tricked, that they absolutely understood who I was, and that’s fine… But we didn’t spend a lot of time on the business.

[40:05] The first two years we went from myself and my co-founder to another 20 engineers, and then I think we hired somebody in finance, and a customer support person, and that’s roughly it. It was basically like, okay, somebody needs to own these problems; I don’t wanna own them, so let’s outsource those. But we didn’t really do anything that a traditional business should be doing. We didn’t have sales, we didn’t have marketing, we didn’t really have half of the functions we now have as a company today. So at that time it looked a little bit like a traditional VC-backed company, except we were just doing really well.

When we raised our series A, which was nine million dollars - which is not a small amount - we were actually profitable when we went into that conversation… Which I think is probably not very common. Profitability can be good and bad; it doesn’t really matter on this side, but to us that was an achievement. It proved that we actually have a business here, and we don’t know what it looks like yet, but there’s something here, and it keeps growing… And that’s always been interesting for us.

I think venture capital has been nice, because it’s given us a lot of breathing room, but it certainly has a cost. I actually treat venture capital almost like a loan. If you raise money, the bar has been drastically raised. You need to understand it. You don’t just raise money and it’s free. There are serious obligations every time you bring in a new round of funding, and those obligations are about – it’s like, how much money do you make? You build that revenue line. I think a lot of early-stage companies make that mistake, and that’s why you hear these stories of like “Well, I thought we’d be able to raise another round, and we couldn’t.” To be quite honest, that’s the fault of the founders. I know the expectations of us if we are to go out a future round. I know what our company has to look like, the milestones we have to achieve.

Before or after?

Before. Before going into that. I know them today for a round, even if we’re gonna raise it in like two years, or something. I know what we have to work towards. And I think it is something that’s interesting, because early on I would have said this feels like a distraction, it feels like it’s the stuff I don’t wanna focus on, but it’s actually the stuff I need to focus on, as like the CEO. And the venture capital has been a forcing function for that.

Over the last year, I’ve actually probably become what looks like a real CEO. My commit graph on GitHub certainly shows this… But that’s been a very – I don’t know what my emotions are about it, but it’s been a transition, for sure… Whereas like before this, I really just focused on engineering and product, and now technically, I run every department at Sentry: marketing, sales, customer operations… I have people that I trust that run them much better than I do, but they still report to me and I still drive a lot of decisions throughout at this point. It’s just very different from building a product. Now I’m actually building a company, and it’s a lot of new skills, to be quite honest.

That’s an interesting transition for a CEO - stuff I don’t wanna focus on, but I have to, and need to, and then dealing with that change. As an engineer, transitioning to these things - I don’t know… Is it tough to make that transition? You shared some things there, but go a little deeper into what you have to do. You said you’re mission-minded, you’re very competitive, so maybe these things are easier for you, but… And I’m thinking of the listeners here in your story, and thinking like “You know, I just wanted to do my thing. This was a lifestyle business, this was a fun thing, and now I had to.” Did you just come to grips with it, and you’re slowly becoming okay, or do you really enjoy being a CEO?

You know, it goes back to what I was saying before. If you want something, you have to be willing to earn it. I want this company to be extremely successful, and whether I wanted to be a CEO in the proper sense or not doesn’t really matter, because my goal ultimately is to make this company successful, and how is it gonna be successful if I don’t do that job well? That’s the way I think about it.

[44:07] Ultimately, a lot of this comes down to I have to be willing to change my mind on things. Two years ago if you asked me about sales, I would tell you that Sentry does not need sales. We get plenty of sign-ups, they pay for Sentry, it’s great. Now I love our sales team, and that’s because our sales team is not the type of sales I don’t like. And that’s actually a nice function of my job - we get to build things the way we want to. Our sales team is very inbound-focused. You’re not gonna see them cold-emailing thousands of people, or anything. What they’re actually doing is just providing a really good customer experience to the people that expect to talk to a salesperson. Two years ago, I was just very naive about it; frankly, I was ignorant. Now I fixed a lot of those behaviors, but I had to come to grips with a lot of my preconceived gut reactions to things aren’t gonna be correct. I might have reasonable opinions and instincts about things, but I have to be willing to understand things I don’t understand. That was a big change for me, because I actually think instinctually I’m very good with software, but it’s also because I’ve been doing it for I guess like 15-20 years at this point… And I don’t have any of that with building a business, other than I can get it off the ground and I can probably figure out how to charge money.

So that was like an interesting come-to-grips moment, where I have to just suck it up and do all these other jobs. Now, frankly, I still struggle with it sometimes. I still write code almost every day, for better or worse, but it’s no longer code that matters. People are not relying on my code to succeed here at Sentry, but other people are relying on me to make sure that we’re setting direction in a company, to make sure people aren’t accidentally building walls in our organization, like silos of information, to make sure that we have a mission, or that we’re building the right things…. So that’s been very interesting.

Honestly, I joke with people – for quite a while I’ve joked about this… I’m more of like a mediator and an administrator than I am somebody that does something tangible, like a builder, like a hands-on person anymore… Even though I do miss that a lot. There’s certainly gratification in just diving into something and getting in the weeds and solving the problem. A CEO, to some degree it’s bad if you do that a lot. You don’t wanna be in the weeds; you wanna let other people solve their problems.

Yeah, because everytime you’re in the weeds, if you think about the true metaphor, “in the weeds” means that your visibility is reduced; you’re probably in the thick of it, your purview is sort of taken away from you, but in the role of CEO, typically elevated, not so much in terms of like better or worse, but just in the fact that you can see more… As you’d mentioned, you’re in charge of all the departments, while you have people in those roles to trust, and report back to you, and there’s a communication flow there. If you’re int he weeds, you’re probably neglecting things.

Yeah, absolutely. That’s my coming-to-grips moment; I still struggle a little bit, but… One of our investors had to constantly badge me, like “What are three most important things for you right now?” and for a long time I’m like “There’s too many things; I can’t just do three.” And now I explicitly don’t do other things. Maybe I’ll do top five or something, but if it’s not in those, I just say “I’m not gonna do it.” It doesn’t matter if I can or not, I’m just not going to… Because it’s usually not important, or somebody else could do it, and potentially somebody else can do it better than I can. So that’s actually been like a really interesting exercise, and genuinely, if you took all of my learnings as being CEO now, and I went back to being an engineer, I bet I could use a lot of these to do my job better. Because if you think about it, as an engineer, a lot of your challenges are like “Well, what should I be working on? How do I prioritize? Oh, but I need to do this thing. The customer says this is broken.” And if you go down to it and you just say “What are the most important things?”, that’s ultimately what you look for in like a very senior level engineer to be able to project-manage well… And ultimately, the skills I’ve gotten better with are those kinds of skills.

A little fun thing here - what are your three most important things for you right now?

[48:08] Oh, that’s a good question… I have to come up with them. Last week it was hire a CFO, hire a Head of Product; I closed both of those, thankfully. And then we’re implementing OKRs here, and the OKRs – those are sort of like the tasks, but the ultimate three important things are like, okay, we need product execution to really ramp up, so we can build this big new product thing; we need to fix strategic finance and business insights and all this stuff inside of the company, so that’s hiring a CFO, and we need alignment and visibility into what everybody’s doing across the board and to make sure we’re on shared missions, and that’s OKRs. So that’s sort of how I drilled into those.

Now it’s sort of like, okay, that’s done; I’m gonna finish this OKRs thing, and then what’s next? Part of it is we’re doing a bunch of new kinds of marketing and making some changes there, so that’s gonna be top of my list. I think the others are gonna be onboarding these new executive hires, making sure they’re very successful and sort of get off the ground running.

You mentioned before that you know where you need to be to raise more funds, and you’ve been through two rounds, is that right?

Three rounds.

Three rounds, so that means series A, series B, series C.

Series C would be the next round, if we’re gonna raise it.

So you did two B’s and one A?

Seed, A and B.

Seed, A and B, gotcha. I’m not very familiar with all the terminology around raising funds; I just know that it is funds, and I’m somewhat familiar, somewhat…

Yeah, just keep increasing the letter.

That’s what I figured, that’s why I said C. [laughter] So given that you know where you need to be, is the vehicle for growth for Sentry - does it always tie back to venture capital? Or is there a point, now that you’ve gotten enough capital to grow, and rewinding back to your original velocity and the bootstrap method when you were there - you could keep growing, but you couldn’t compete in the long-term, because of competition in the market; so you had to make a choice, and you did, and that’s where you’re at now. You’ve been through a couple rounds of funding, and you realized the growth vehicle. Is that the next step for you, where you keep raising funds, or will you eventually be self-sufficient financially?

One day we will be self-sufficient. Right now our ambitions are much bigger than our bank account. I can be very direct about this…

Be direct.

I want to replace New Relic in the industry, and we’re not gonna do that with where we are today… Certainly not quickly. And that’s a much bigger ambition. And maybe that’s not actually replace New Relic, but I wanna tackle a lot of the problem that New Relic has owned for a very long time, in a very specific market, very differently… And the challenges of that - it’s potentially a lot of stuff to build, it’s a lot of stuff to support; it’s much bigger than this error tracking component that Sentry has today.

What venture capital is honestly for - it’s purely to allow you to spend a lot of money to make big bets, and those big bets are entirely “Maybe grow faster”, right? A very common reason to raise money is because you’re an enterprise product or something, and you have a sales force, and it takes about a year or maybe two years to get the revenue back from that sale, but you can sort of predictably do that. So you’re gonna go raise a ton of money, hire a ton of salespeople, you’re gonna lose a lot of money for the next 1-2 years, but then after that, you’re gonna see a drastic increase in cashflow. That’s not us, to be clear, but we would like to drastically expand our engineering presence and our product line. Doing that is either going to take us until I’m old and grey, or it’s gonna take a lot more people.

If we raise money again, it will certainly be to go for a much bigger target, is how I would talk about it. Not that it’s a bigger target than what we already have internally, but publicly it’s a bigger target than what it looks like we might have today.

[52:10] When you’re thinking about these kinds of things, I’m trying to think of it like – we started with this conversation around what’s important to you right now; so you’re in the now, and maybe the now is the next year, year-and-a-half maybe… How do you think about what’s important to you over the next five years, and maybe the lifespan of the business? Do you concern yourself with the longevity and the sustainability on the long-term, or do you simply focus on - at least now - what you need to do now to get to the next milestones? Are milestone-based, or do you have this bigger vision outside of it, that’s many years, maybe decades in length, in terms of a plan? …or at least an idea of where to go.

Yeah, so I’m traditionally a very tactical, iterative person, which means milestones are my strength. We have maybe a two-year outline of what we’d like to do. We have business targets, and that’s actually important. It’s like “We need to hit this much revenue. How fast can we get there?” These are very, very big targets. These are like “Maybe we can hit it in three years if we’re amazing; otherwise maybe it’s like 4-5 years. So that’s the farthest out we look, but that’s only from like an abstract revenue goal.

Everything else we do is like, okay, we know we wanna build this kind of stuff, and we know that’s our solution to expansion, so let’s build this stuff, let’s figure out how we charge money for it, make it reasonable, and let’s set milestones around short-term growth. We probably don’t look farther ahead than one year in terms of goal-setting, and most of what we do is on a quarterly basis. So we are doing stuff that is like six months out at this point, but it’s very vague. We intentionally do that. We have quarterly goals, and they sort of map up to some annual goals, but “be willing to throw away everything the next quarter” kind of thing. I think that’s actually totally fine.

I can respect big, established companies like Amazon, where they can project out exactly what their bottom line is gonna be in two years, and things like that, but I have no idea how they accomplish that kind of stuff, and to me it seems a little bit less interesting; it’s not creative. Whereas being able to react still ensures you keep moving towards something new… Because Sentry has been around a very long time, and we still constantly change the product, and now we’re building bigger, giant products on top of it… And that’s somewhat uncommon, I think, for products that have as large of a reach as ours.

I don’t know, it’s an interesting challenge, and I think I’ve always struggled to become a more strategic thinker… Other than I can give you some pie in the sky product vision or something, but it doesn’t mean we’d actually work towards it.

Yeah. You just seem very visionary and vision-focused, and I was just curious how far you stretch your vision and remain relevant, and not in the weeds, because sometimes your vision can be your weeds; you know, not just in the fun tinkering you might do because you’re an engineer at heart, but also just in illogical thinking about long-term future goals that just don’t make sense to focus on now, because hey, there’s things on fire today - you need a CFO, or you need a head of sales, or a head of product, or whatever it might be, to get to the next bigger milestone. That’s where you’re focus should be, so I just wondered how you balance those perspectives, but keep them both in check, because you need to have a long enough term vision to course-correct along the way, but enough of a dream to reach, like you said.

I’m curious - it sounds like you’ve had some pretty significant challenges as a CEO, you’ve been tested, and given where this conversation began, with dropping out of high school, all that stuff, you’ve learned a lot about being a CEO, at least what you’ve demonstrated here in this call today… I’m curious, where did you get this knowledge? Did you get it literally by bloody knuckles, being in the trenches? Did you read somebody’s blog? Do you have advisors? Obviously, you’ve taken funding, so you’ve got people that come in and give you advice… How did you learn what you know?

[56:20] So I’d say I’ve at least been around the block a few times, so I’ve seen a lot of things happen in companies that I can respect, and on the counter side, I’ve seen a lot of failures that I don’t wanna repeat… So I have a lot of prior knowledge, even if it’s not actually running a company or a business function; that’s helped me immensely.

I think I have a tendency to just deal with problems. I sort of naively assume everything’s easy to solve, which for better or worse it does give me an advantage that I’m willing to try to just like do something differently, or just assume something’s gonna work, even if it completely fails. That’s helped me a lot.

I think there’s a huge benefit to being a startup CEO, in that if you’re the founder specifically, you’re actually given a lot of freedom to mess things up and to learn along the way. If we hire an executive, they’re not given that same kind of luxury. The CFO has to actually fully know how to do their job, whereas I’ve been able to learn how to do my job better and better, and I’ll be better at it tomorrow, and next year, and the likes.

Then on top of that, I’ve actually found our board of directors genuinely very helpful over the years. They’ve provided good feedback, they sort of keep my wrong opinions in check, they push my right opinions… That’s been immensely helpful.

How do you deal with that? Let’s camp out on the wrong ones - how do you deal with being wrong, in those cases? Do you take it personally, do you have thick skin?

I actually tell every new hire – because I try to break down this CEO barrier, because a lot of people think “Oh, the CEO - be careful around them.” It’s this weird, mythical thing, and I try to break that. I don’t succeed at it, for what it’s worth, but… One thing I tell them is like “Feel free to DM me on Slack if there’s any questions, contact switching is no problem for me, I’m happy to answer them.”

I also tell them “If I give an opinion, it’s because you asked for it, it’s not because I care about it”, which is very true. I always say I have strong opinions weakly held, and I don’t take offense if somebody disagrees with me. Now, some opinions I’m very strong about, and generally, if you come with a well-articulated reason – and it doesn’t even have to be that thought out or that data-backed or something, and it’s not just off the cuff, where you haven’t thought it through, then I have no problem at all just completely changing my mind.

We used to always say in board meetings – so we have two investor board member. We used to always say if both of them agree on something, I should just accept that it’s almost certainly true, because they are of drastically different backgrounds, in my opinion… And that actually has worked out pretty well. I think that kind of balance has always been healthy. That doesn’t mean we don’t get into debates all the time, about like “Oh, should we do this thing, or this thing?”

Early on it felt like, “Oh, hey, trust me. I know what I’m doing… Me, the founder. Oh, I know how to build this; I know my audience”, and stuff. And it would be them being like “Really, you should probably be hiring a CFO right now.” It used to take me a long time to come to grips with this stuff they were saying and to sort of agree with them, but I think now, after going through those experiences, I’ve gotten much better about agreeing on the things that I think – you know, ultimately it is what I think, but agreeing on the things that are certainly important to me… But that doesn’t mean I agree on everything yet. I don’t think my investors are always right, but I always think they have a valuable opinion to add.

I think that’s an important mindset you have to have, not just as a CEO, but I think it’s anybody that’s gonna be any kind of leader, whether it’s like an executive in a company, a manager of a team, or even just this inspirational superstar engineer on a team. You wanna be that leader, and being willing to hear other people out. That’s actually one of our core values here at Sentry that’s super-important.

[01:00:10.00] I have two major questions I wanna ask you before we close up the call. One of them is what in your role as a CEO do you loathe? You have to do it, it’s something that you know is part of your role, but you’re like “Man, I just don’t like doing this”, and you probably as CEO can’t ever really off-load it, but you’ve gotta do it. What is that for you?

I generally don’t like managing people, period. I’ve never wanted to be a people manager, and that is 100% my job at this point. Slightly different than a normal people manager. I’m not just here to coach you and to be like “Well, what do you think we should be doing best?” I am here to somewhat delegate, like “We need to get this done, and I need to hold you accountable”, but I don’t really enjoy the people management aspect.

I really like when I can hire somebody and they can be mostly autonomous. Maybe it’s the engineer in me, the efficiency of it, but I’ve seen over time that that is often a mistake. You need that personnel management in growth, and stuff… I actually have 10 or 11 direct reports now, which if you read any book, I think they suggest 7 is the maximum… Whether that’s true or not - you know, the internet is full of a lot of advice, it’s all use case-specific…


Yeah, yeah. And I’ve found that a struggle. I’m sure some of my reports don’t get as much time as they need to help them grow, but I think they still do a really good job. But in general, whenever I have to go through performance reviews, or god-forbid, an employee needs to be doing better - those are the worst situations for me. I don’t like that conflict. I’ve gotten better about dealing with it, I think, and honestly, I think I’m fairly good at it these days, but I still don’t enjoy it.

I feel you, and I empathize. The next bigger question for you is what do you fear most, as CEO? Obviously, you’re in the role you are, you know what you’ve done in terms of venture capital raising, you know the milestones, you know the next milestones you have to get to to raise more money if you decide to, or eventually become self-sufficient, as we’ve talked about… I don’t even know where to plant this question, but you may know, because you’ll just probably instinctively have a place to plant it, but… What is your biggest fear as a CEO? Today, tomorrow, a year from now, where do you place this?

Yeah… All I think about every day is sort of not losing. I say you have a reason to show up to work, and mine is always to be the best at whatever we decide to do. So my fear would just be like, you know, we’re building products and we just can’t win against the competition… Because then our business isn’t gonna succeed at that point. I think about that in every little thing we do, like “How do we make sure this is the best version of it?” We literally measure ourselves by how we stack up against all of our competitors… And that’s people in our direct space, which is error tracking, which we perform exceedingly well against; we generally don’t lose against a competitor anymore in that space, so we consider ourselves doing great there. That’s how we measure it.

And then we sort of measure our future against the wider application monitoring space, which is like New Relic and whatnot. We actually lose quite often if we’re going up against New Relic, and they’re already paying New Relic, right? They’d be like “Well, New Relic sort of does what you do too, why should we pay for you?”, even though it’s a completely different product. And that to me is like “We have to get over that hurdle.”

What I think most about – and it’s not like a serious fear, but it’s the thing that I think most about, and the biggest risk, I think… It’s like, we have to be able to get past that hurdle. But again, going back to being very naive - I’m very confident, to a degree of arrogance, that like, these hurdles are not that hard to pass. It doesn’t mean I know the easiest way to get there, but I certainly believe we can do it. But that is where a lot of my thought process goes into.

[01:04:04.01] I can empathize with that arrogance, or maybe even somebody thinking it’s arrogance, because when I do any of these things, like enneagram, or strength finders, or skills, like one of my top skills, visionary and self-assurance is always in the top two; they either flip flop, or they’re always in the top two. So for me, I maybe place that on you as well, it seems, because you seem very visionary, you seem very self-assured. That’s not really arrogance, that’s just confidence, you know? And I think you need to have that as a CEO.

I think earlier in my career it was arrogance, and much more these days it’s confidence.

I’m sure we can go a little deeper on some of these subjects… Let’s close the show like this - do you have anything super-secret, that’s not out there, no one knows about it that it’s coming up? Maybe you can tease it, drop a landing page… I don’t know what you’ve got, but is there anything happening in the near future, since you’re so goal-focused, that we can tee up today here for the listeners? Either as the CEO, as the business, or a new product?

Yeah, I’ll focus on product, because ultimately that’s what I care about… Interestingly, nothing’s really a secret, because you can just load up our repository on GitHub and it’s all in there, but we’re sort of building – you know, I’ve mentioned this New Relic thing… We’re trying to enter the application monitoring market, but a different spin on it. I wanna say nobody has seen this yet - we gave a pretty hefty, big feature to some select customers a week ago, which is advanced search; it’s not that interesting on its own, but what we’re sort of building now is this idea where – you know, I think of myself as a developer whenever we build product, which I think is the advantage I have, and all I care about as a developer is I shipped new code, and I screwed something up. That’s all I really wanna know. It doesn’t matter to me “Oh, there’s this bug from a year ago and it’s happening a bunch, or it’s happening a lot more now than it used to…”, like, yeah, that’s a thing, but ultimately it’s not that important.

So we think about that idea, and we decided to basically – not pivot, but hedge the entire company and product against this idea of “What if I could tell you, when you ship new code, this commit that you have in here, it’s causing this error? But not just this error. What if I could also tell you that it just made the sign-up page 500 slower? This specific commit.” What if I could tell you “Now you’re getting no sign-ups, and we’re pretty sure it’s this commit”, or something.

I think that’s a very fascinating spin on what we’ve traditionally looked at monitoring for, and more importantly for me, it gets at this continuous iteration cycle, so it becomes a part of your [01:06:45.11] control. So we’re actually building a lot of that stuff right now, and we’ve been building it for the better part of this year, honestly. It turns out it’s a pretty big technical investment when you overhaul everything, but I’m super-excited about that, and I think we’re gonna have stuff coming out to early adopters on Sentry maybe by the end of the year… But it’s gonna be in pieces.

What the ultimate end product looks like, I have no idea… But we’re trying to aggressively go after this APM space; we’re calling it APM for developers. The developers part is really we think about the reason errors and everything else matters is because you changed code, and ultimately that’s the causation, the root cause, right?

And that’s our spin on it. So I don’t quite know what it’s all gonna look like, but I was talking a lot about we wanna invest a lot more, and that’s what it is. We wanna build something bigger at this point, something wider-reaching, and honestly, something that changes the game again, just like error tracking once changed the logging or monitoring game.

We’ll see, but that’s sort of like the big thing that I think a lot about lately, and that’s where a lot of… You know, we talked about like a couple-year vision - it’s all in that area.

[01:07:51.12] So as a CEO on a podcast that has a decent reach - I mean, we’re not talking to every single person out there… I mean, you’ve just shared the future, where you’re trying to go. Does that ever worry you, that you’re putting “secret” out there? Because you said it’s on GitHub, in the repository; you don’t seem like you’re trying to hide it. Does that concern you?

Not at all. I’m very confident in our ability to execute. I just don’t think anybody else can surpass us. We’ve got like on the order of 35 in engineering at this point. Any of our direct competitors are much smaller than us. Our bigger competitors - when have you ever seen a giant company pivot? So I don’t think there’s a lot of risk in sharing it, and it’s part of our core value.

We believe in open source. It’s not a business maneuver for us. I really care about open source, and I don’t think it’s a harmful idea. I don’t think there’s harm in transparency; if anything else, it helps our customers be reassured that we’re thinking about the future, and not just this one thing that we’re giving them. I think it certainly has its risks, but I don’t think they’re that significant.

When we’ve talked about fundraising earlier, you mentioned when you go to whomever is in the series A or series B, and you’ve gotta share with them where you’re trying to go, I’m sure that the money they give you, the valuation, it’s all based on this bet, as you’d said - getting lots of money to place a bet, essentially. Back in May, earlier this year, you raised your series B, 16 million dollars… Was this part of that conversation?

So actually we raised – this is a little bit of a trick. We raised the money last August, we just didn’t do any press about it until May, for whatever reason… But it was not part of the conversation.

Was that strategic, not sharing the details?

It was strategic, but we didn’t really mean to wait until May to share it. We were gonna do it early in the year, and we just didn’t get around to it, honestly.

Too busy.

Gotcha. So was that part of the conversation there? Like, the best, mostly. Because to go back to placing these large bets, like you’d mentioned, a large overhaul, it’s a significant shift in your business, much wider reach… Was that part of the bet?

No, so in that case literally the capital was just to grow our core business, and the revenue generation there and everything. That’s really what we have been focused on for quite a while now… Still building on it, but growing our core business.

You know, because we actually were a pretty healthy business, so we actually still have a lot of the capital we’d raised in the bank… So we are doing that with that capital, but it wasn’t part of the original conversation.

Gotcha. David, thank you so much for sharing your story. I’m sure we can go much deeper… I’d love to do what I’m calling a founder update kind of thing; along the way, given that we have a good portion of your story now, I’m sure the listeners will eventually be curious later on, as you meet these milestones, some updates along the way… So I’d love to dive into maybe more of these conversations with you in the future, and hopefully you’ll agree.

For sure. I’m sure we’ll have a lot more to share.

Any closing advice for those listening who may be going down a similar path, to encourage them or keep them going, or a small lessons learned that we can share on the departure of the call ?

All I’ll say is it’s never easy, but I think the rewarding things in life are never gonna be easy. You do have to work very hard for them.

Well said. Thank you, David. I appreciate it.

Thank you.


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