Introduction to the Alphalist Podcast -- Tobias Schlottke: We're straight in here. Tobias Schlottke: Welcome to the Alphalist Podcast. I'm your host, Tobi, and today with me, I have David Kramer. And David is the founder of Sentry. David, hey. David Cramer: Hey, great to be here.
Tobias Schlottke: I hope you're good. And, um, I think there's not, there's not, So much needed as an introduction for you, actually, uh, because I guess everyone here knows Sentry, right? Um, but, but maybe a few words, like, I think I, I Googled like you, you secured over 200 million in funding, et cetera, and you are at over 100 million in AR. Tobias Schlottke: Is that correct?
David Cramer: Yeah, what's the easiest way? Um, Sentry is a late stage startup, I would say at this point. Yeah, I don't know how much funding, but it's a lot. Uh, we make a bunch of money. We publicly announced that we have over 100, 000 customers, um, on our cloud service. Customers being like, sort of companies that use it, and 100 million in revenue. Um, or at least, I think we said ARR, I forget. Uh, And David Cramer: Yeah.
David Cramer: I don't know, we're sort of a big company, but not too big. We're like 350, 400 people. And so, David Cramer: we're turning error monitoring into a big deal, I guess. Early Days and Bootstrapping -- Tobias Schlottke: um, like looking back, um, before you, you started, um, like what was your idea on error monitoring? And, and, and I mean, did you, did you imagine it could grow so, so, so much?
David Cramer: Ooh, yeah, I don't know. So, I think, I remember this conversation. When we raised the money, we had a couple thousand customers, under a million in revenue. So we were bootstrapped. I remember this conversation with our investor, right after he joined. Maybe right before we invested, I'm not sure, somewhere around there, where we plotted out how to get to a hundred million in revenue. And I remember just rolling my eyes when we had that conversation, as in, I'm like, uh huh, this is, yeah, very unlikely or something. I'm like, I, it doesn't make any sense to me. And so I would say, no, we didn't imagine it, but what venture teaches you, like when you raise venture capital, is you have to think big, you have to build a really big business, otherwise you shouldn't raise capital, you know? And so. You know, probably a few years later that ambition changed. There was like a little bit more evidence that we could grow it. But even when you're like at ten to twenty million, you're still very, very far from something like a hundred million. And it's just, it's such a different thing. And I often wonder, the things that I thought were sort of easy to manage back then, or easy approaches to problems, I often wonder if those still work.
David Cramer: I, I keep trying to apply them, to be clear. Um, And at the same time, I often wonder if it's as complex as people make it out to be. Like, I, I think, you know, we've, we've had a lot of success with product market fit, and so growth has been fairly natural, which is a, is a great problem to have, but it's still a problem. Um, because once you're trying to, you know, grow at the scale we are, things are a little bit more difficult, I would say. Yeah.
Tobias Schlottke: Maybe starting a bit earlier than, um, with Sentry, um, I always ask my listeners, uh, sorry, I always ask my guests, not my listeners, uh, about their, their nerd path, uh, and their, their, their journey into, uh, how, how they got where they are. Uh, like, how, how did you get where you are? Like, why did you actually start with engineering, et cetera? Tobias Schlottke: What is, what is your, your background story?
David Cramer: Yeah. So honestly, I just like building things and I don't know, it's always hard to say, like, why this specific thing, you know, because as an example, like, I like building things. There's a lot of different ways you can build stuff. Software isn't the only one. Um, I think, there's like, it's right time, right place. Opportunities in the Wild West Days of the Internet --
David Cramer: And so I think, like, when I was a teenager, the internet was in, like, the glory days. When it was still the wild west, not everything was figured out. There was a lot of opportunity. It was very rough, um, I mean this was the era of like GeoCities and IRC and all this stuff that was, it was very, say, unmoderated, and capitalism David Cramer: had not yet taken full effect of it, and also, it was, Tobias Schlottke: of the marquee and the center tag, right?
David Cramer: yes, yes, the blink tag as well. David Cramer: Um, Tobias Schlottke: tag, yeah.
David Cramer: what I, yeah, I think what the big deal though was it was like super accessible. There were, there was no like gatekeeping of any shape or form. And I mean that not in the sense of like people intentionally gatekeep it, like to build a, a technology or a technology company even. It was actually not that difficult. Like technology was far worse, but the internet was small. The complexity was small. Security wasn't really a thing people worried about. It was all these like different shapes of things. And so I feel like I got, I was fortunate that I was um, I kind of had gotten hold of a computer and I was able to build these little applications on a LAMP stack, which was like PHP and MySQL back in the day.
Building and Learning from Projects -- David Cramer: And you know, one thing led to another, and it was, it was almost like this way where I don't consider myself a creative person in like the traditional light of like, you know, R or music or anything like that, but like, there's also like creativity in software. And so it was kind of a way for me to express that.
David Cramer: I would build like little hobby websites for video games where my, um, my first job, like paid job. Was I reverse engineered world of Warcraft's data files and built a database out of it and published it on the internet. Um, and that was super fun. You know, I was a ga like a teenager. I was a like big gamer and stuff.
David Cramer: I never really played World of Warcraft, but, um, but it was just cool. It was like really interesting. It was, it was problem solving. It didn't require academics, like in the sense of, you know, I'm, I'm a high school dropout, eventually college dropout. Um, but I'm not, I'm fully self-taught, you know, and you can kind of figure it out.
David Cramer: It's harder these days. Mind you, um. But you can still kind of like teach yourself all this, you can be good at it, like, I would like to think I'm a pretty strong engineer, even though I have no formal training whatsoever, you know? And that, to me, is a really, really big deal. There's few fields in the industry that you can say those kinds of things about, let alone ones where you can actually make significant amounts of money in your career, you know?
Tobias Schlottke: So, I think you just hit the right spot then, right? David Cramer: Yeah, I think it was a little bit I'm glad this is the industry I'm part of. And, uh, and I guess, actually, to kind of further your question, like, on Sentry, know, I'm glad Sentry's been successful, but I actually think there's tons of opportunity in tech in general for the folks that are ambitious, of capable of doing it, you know.
David Cramer: And Sentry is just one of the many things I've built, you know. I could have just as easily worked at, you know, a bunch of other startups, which I have. Um, granted, most of them were not as successful as Sentry. Uh, But there's always a lot of opportunity in the industry for people that are driven and have the capabilities.
David Cramer: And a lot of the capabilities honestly just come from drive. Like obviously you've got to be able to figure it out. And I don't know if that's a, the right kind of brain or personality or whatever it is, but it's mostly just like, it's like a lot of hard work, right? And so like Sentry is just one of many things I built over the years, one of the many open source things. And it just happened to have a path to monetization that worked. And it just happened to be a thing that had a really wide, addressable market, you know? And so, there was a lot of opportunity in that, but I don't see it so much as like a luck or anything like that, just more that when you're given the opportunity, you either take it or you don't take it. Um, and there's a, there's a lot of chances, I guess, for opportunity. So, but yeah, it just, you know, one of many things and, you know, started small, started without ambition, I guess, per se, with, without financial ambition, I would say. Um, and then just, you know, when you see something that, like, really sticks, and And I guess also when you get older in life and you actually, you know, want to have money to pay for things, you start thinking more critically about how you earn more money and stuff, so. Um, but no, they're all good problems, but again, I think it's just, you know, the internet's a really open, open place and still, you know, ignoring there's always hype waves around random stuff.
Branding, Design and how to make an "unsexy" product cool -- David Cramer: You know, Sentry is, is and was not ever like a sexy company, right? Like error monitoring, nobody finds that interesting. David Cramer: Not even Tobias Schlottke: Well, I Tobias Schlottke: would consider you like the, it's the sexiest of the error monitoring solutions out there from my perspective. And, uh, like we talk about that later as well, right? I
David Cramer: I think we made it that way, to be fair, but, but like, even the things we care about have nothing to do with enterprise software. Like, we're big on brand and like, visual marketing and all this stuff. There's so many, like, look at Salesforce. You know, they, they have brand now, but like, it is not a, it's not a nice piece of software to look at, let alone use most days. Wildly successful company, right? And so I think you make things interesting and you find reasons to do things, but solving error monitoring is like a sort of, actually I guess what now will effectively probably be the equivalent of my life's work, um, is not anything that I think is that interesting, you know?
Tobias Schlottke: think like for Salesforce, um, it can be considered a sign of success if people build systems on top of your systems that make your system visually more appealing. David Cramer: Uh, sign Tobias Schlottke: but you solve that yourself, right? Um, so you early on, um, discovered that the design or more appealing side of things is, is, is part of your success or can be part of your success. What, what, what, what was the moment, uh, the key moment when you discovered that?
David Cramer: So I value design. Like, in all things. I'm not capable of it in almost anything. I will say the things like DALI and the LLMs of the world, I appreciate because they allow me to be slightly less incompetent. Um, but I very much value it. Not everybody does, to be fair. But I think it's such, it's like, um, think about interior design and stuff.
David Cramer: Like, we like having like, Sort of a better surrounding or even like exterior, like landscaping, all these things in life. We like just surrounding ourselves with sort of more visually pleasing or more organized or whatever you want to think of it as. And I always valued that in software and products and everything too, right?
David Cramer: And so, you know, when, when I was, whenever I build anything, in fact, I'm always trying to harass a designer to help me on it. And that was no different than with Sentry. Um, And, I think it's actually gotten easier over the years, from a design point of view, for engineers, who are not, uh, creative in that regard, to be able to do a better job with things like frameworks, like Booster App, or Tailwind Components, or any of these other forms, you know, which is awesome. Um, but it's just like something I valued, and, and we put it front and center, and I, I actually think the best organizations in the world these days do put design front and center at their companies, if nothing else, because it's a differentiator. But, but it's not even just design, like I'm a big believer in brand marketing. Um, and it's sort of just, it's how you represent yourself as a whole. Like, what are the values you stand for without, like, teaching them to somebody, right? Well, clearly, Sentry puts a bunch of effort into design, so we must value design. And if you value design, you probably are like, Oh yeah, I like that Sentry values design, you know? And so, in a lot of it, it was just like, showing our values to the world. And it's the same reason, like, our marketing copy is like, super cheeky. Where we kind of just like, belittle ourselves or make fun of whatever we do or something. And it's because We think it's kind of a joke. It's a fun joke. Um, but it's just us being like authentic in what we think is like how, how we should be instead of like being fake, I guess. And so it's the same kind of thing all wrapped up in this is it's just like how we think about our brand is our values and what we care about and how we want to represent ourselves, you know?
Tobias Schlottke: Okay. And. Monetizing an Open Source Product -- Tobias Schlottke: You, you, you, you reached a certain, certain size and you raised a bunch of money for that, um, to, to, to actually get there. Um, and, and you managed that, uh, mentioned that at the beginning you, you were basically bootstrapping, um, and, uh, playing with open source, et cetera. Um, if you could start from scratch, if you would be like, uh, let's say like zero to 10, Dollars in monthly recurring revenue.
Tobias Schlottke: Um, what would you do differently? Or would you, would you just do it the same thing, same, same, same style again?
David Cramer: Yeah, that one is tough. Uh, you know, it's interesting because we, we struggle with this internally. Like building one product is one thing. Building a second product is an entirely another thing. And you know, I talked about opportunity. We had built something that had product market fit, whether I knew that at the time, almost irrelevant, but there was clearly a demand there and I just kept building it, you know, manufacturing that is very different, but I think there's a couple of things.
David Cramer: So I can't give real advice. Um, and I don't like to bullshit, and so, what I, what I can say is it's hard. I think you've got to have determination to like actually vet out if something's going to work or not. Um, and one thing Sentry did from the beginning was we, we kind of knew there was demand. It was already open source back in the day, so like people could use it. Uh, and they were using it, which was helpful because we knew there was something there. But when we spun up the, the business and the cloud services, those cost us money, right? And we were bootstrapped. And I think partially because we were bootstrapped, we said, hey, it's only in a paid service. There is no free tier.
David Cramer: There is now, but that's different. Um, and I actually think that was a really good move because it allowed us to effectively bootstrap, build the business in a time otherwise where it actually might have been hard for us to raise venture capital because of the kind of business we were, like open source, developer tools, all this stuff. Um, but it also instilled this rigor in like, hey, it's, it's a product. You, you pay for it. Like if it has value, you'll pay for it. And that's a really good reinforcing function. And so. I think one thing I often see, so I invest in a lot of startups and I actually bias towards developer tools and open source.
David Cramer: And those are two of the harder industries to get into. Um, but I think one of the biggest challenges I see from people is they'll have something that's popular, like an open source thing, and there's probably a path to monetize it, but it's a little tricky, but they won't, or they'll think it's kind of like straightforward to just like, Maybe there's a way they'll get them over the line at some point.
David Cramer: And I think the big mistake is just like, you got to charge right away. You got to find that value, value extraction mechanism to fund the business. And I think we were fortunate. That Sentry is pretty straightforward. It's infrastructure. We can cloud host it. We sell us hosting it to you. You know, it's kind of a straightforward exchange. Um, but it's really hard to get it to the point where you've got something that will generate real revenue. Even going back to like. Did we ever think AERS would be this big? We actually fully believed that AERS would be small and we had to build many other products. We still believe we have to build many other products, and we do, but we were fully committed to the idea that it's got to be a suite of offerings because AERS will never make a hundred million dollars on its own, you know, kind of thing.
Pessisi -- David Cramer: That was our belief at the time, and you know, that's no longer my belief, but the premise of it was kind of, you can't, like, You almost actually have to be a pessimist about the business. You have to believe it's, it's not going to succeed and you've got to keep working at it, or offer many other things and stuff.
David Cramer: Because our thesis was, you have to generate 100 million in revenue. That number might be bigger these days for what it's worth. Um, but you have to generate that if you're raising venture capital. And if you cannot find a path to build a business that is that big, you are fooling yourselves into, like, kind of what you're doing, right? And so we're like, well how would we possibly do that? And that was just the exercise. Microsoft And the advantage we have is there's an established market in our space, the APM industry. You know, things like New Relic or AppDynamics or Datadog or something. They all kind of sell in this rough space. So there's, there's clearly money to be made there.
David Cramer: It's a little bit different than like a greenfield space. Um, but I think that's also true for most markets if you like look at them like carefully. And so, I don't know, it's really tough to get your product market fit. But I think you got to charge right away. And, and I will say like every day, I We were looking at the new customers numbers, like who's paying us today?
David Cramer: Is there another person today? Are there three more people today? Are there five more people today? And we tracked it to the point of view where we tracked MRR, not ARR, because it was like, it would move at like a weekly level in small increments. And MRR is like, just kind of an interesting way to constantly see it moving in a scale where you, you see little numbers fluctuate a lot more. And we were super hands on with customers, which you gotta be, obviously, like, they always say like early stage, you're just like, you're, you are the salesperson, which is true. I'm not a salesperson by any means, but I, um, I was selling the product even if I didn't realize it. Even if I was just going out, hanging out with my peers, talking about what I was building, you know, it was still sales. And so I think you just got to be hyper focused on that stuff.
Tobias Schlottke: But, but still, what would you do differently? Nothing or? Never Change a Thing -- David Cramer: I would never change anything because I believe in the challenge of paradoxes. Like if I change one thing, what happens? Um, I do think if I did another company, which I thought about a lot one day, if like, if I were ever just, I don't really want to do another company because it takes a lot of effort.
David Cramer: Like, um, This is year None of it, no. I've been, like, full time on Sentry for 10 years now, right, and the project's Self-Serve Business Model and Sales Teams -- David Cramer: older than that, so I don't want to spend another, like, 15, 20 years of my life just to experiment, but I would love to try different things before, because some of the interesting things about Sentry So, Sentry is a largely self serve, bottoms up business, you know. I think we say we have
David Cramer: 60, 000 paid accounts, something like that, paid customers. And about, and I'm not sure if this is public, but it's fine, uh, about 70 percent of our revenue, and there's a margin of error in there, comes from self serve, from people just swiping their credit card. And that is rare in the IT enterprise space, right? And to me, that is like an awesome accomplishment. I'm like, what if it was 100%? How much more efficient, because I'm a big believer in efficiency, it's why I like tech, how much more efficient could you run a business if it was 100%?
David Cramer: Like, if you take a lot of traditional business, sales is a really big cost. And it has ROI, but the ROI is paid. You kind of like generate faster revenue, but you pay a lot of money to generate that revenue. And then you also have that little bit of this challenge where, you know, sometimes you don't, and it's a really big expenditure, and sometimes it takes many years, so you need a lot of capital up front.
David Cramer: And I'm like, well, what if everything was self serve? Like, one, could you do it? Could you build a hundred million or a billion dollar revenue business purely from self serve, particularly in a space that is not traditionally that? And, could you do it? And still capture the same market segment. \
David Cramer: And what I mean by that is often like,. Uh, big enterprise customers will, they, they often, they have these annoying needs, but the needs are kind of manufactured. But what they need is kind of a human, right? They need that human point of contact And there's some
David Cramer: reasons for why it's valuable, of course, but I don't know if you could capture that segment of the market without a sales team or that like kind of something that was more of a like a, we call it touch, like touch sales approach.
David Cramer: Um, but either way, I would love to see how big you could build a fully self serve business. That would be an interesting thing. Again, I wouldn't change, but I would love to like, you know, alternate reality, see what would happen. I think the other thing that would be interesting is. Smaller, more Efficent Teams -- David Cramer: And this is more of a recent lesson, it's like trying to take more focus and doing less and keeping the team smaller.
David Cramer: Because one of the biggest challenges I've seen from building a company is literally just people. It's, it's, the more people you have, the more complexity, the more logistics you have to deal with, communication gaps, all these other problems, right? Career tracks, all, all, like, infinite variations of things that happen the more people you add. And I'm like, well how far could you get with a tiny team? And a lot of businesses have shown us you can get very, very far. And private equity shows us you can get very, very far as well, right? Now a lot of times private equity is taking something that's already built, mind you, so the R& D cost is paid. But, I do think there's a lot of, again going back to inefficiency, I think like, in general, Silicon Valley operates companies very inefficiently. And we do it because, frankly, we're just lazy. We do what has worked before because we're not trying. Like, our goal is not, like, build a new innovation model for building a business.
David Cramer: Our goal is to build a business, right? But I do think it would be interesting to, like, challenge a lot of the status quo. And we've done some of that at Sentry, mind you, with, like, big self serve business, the open source thing, even though technically we're not open source for the majority anymore. Um, But there are, like, a lot of these interesting ideas that, if you just reason through them from first principles, there's no reason they shouldn't work. And so, I don't know, it's, again, I wouldn't change anything, but I think there's a lot of different ways I would love to see people approach businesses, versus just the run of the mill, you know, copycat enterprise company
Work with friends not solopreneaur -- Tobias Schlottke: . Tobias Schlottke: Sounds as if you, you're a bit tired of venture capital as well. And you would, if I, if you would have had the chance also build a bootstrap business alone in your, in your basement, uh, and, and scale it up to let's say 2 million in ARR and only have your server costs and yourself as, as, uh, as like base costs, is that, is that true?
David Cramer: Uh, maybe not that far, but like, what I've talked about, because I always hypothesize, like, what will I do one day post sentry? And I'm like, you know what would be really fun? Get you and your ten best friends that are really, really skilled at sort of their domain, and And just build sort of a private equity company.
David Cramer: And the reason I say that is because there's sort of this size of business you can manage, right? And I'm like, well, how big of a business could you manage with 10 people that are very skilled at their craft, right? And I'm like, could you build a 100 million business off that? Okay, maybe not. There's a lot of moving parts at that point.
David Cramer: But could you build, you know, a 10 million or a 20 million business? 100%. Absolutely, you know. Most people that get to 20 million in revenue, they've got a hundred employees or something along those lines. And you definitely do not need that level of scale. And so, that's how I would, I would prefer it. One, because I don't have every skill under the sun. Two, it's a lot of hard work. Three, it's lonely. Like, you actually want, like, you need a peer group to collaborate with on stuff. Um, and I, I very much think a lot about, like, your, at least for folks like me, Your work is kind of your life, in the sense of like, all of my friends are people I've worked with or I know through work, you know, half of them have, you know, half of my friends at this point have either worked at Sentry or still work at Sentry, um, and whether people like it or not, you, I mean, your social bonds are the people you spend the most time with, you know, and so, I would want to keep those kinds of things, and I just think it would be really interesting to do it at a smaller scale, but with big ambitions still.
Evolving Role: CEO --> CTO --> CPO -- Tobias Schlottke: And you yourself. You, you, you pivoted, um, role wise from like calling yourself a founder to a CTO, now a CPO. So, you, you, you seem to be like all over the place, I guess, as a, as a founder always is. Like, what, what did lead you to that, to that change in roles?
David Cramer: Yeah, so one of the great advantages about being a founder, if you don't have ego, um, or rather if you have a moderate amount of ego, not too much ego, is you can just change your job and still have a huge amount of impact, a huge amount of influence over the company, right? Like, if you ask anybody internally at Sentry, like I hired a CEO, be almost five years ago or even five years ago now, um, I don't feel like I lost any influence in the company whatsoever from stepping down from the CEO role.
David Cramer: And technically the CEO is my boss, to be clear. Um, I feel like in a lot of ways in day to day interactions, even though, like, CEO makes the final call, we are more peers, if anything. And it just, it brought in somebody else that was a partner to work with, you know, that could do more. Um, and I didn't like doing a bunch of the job.
David Cramer: And so that was the other big thing. So for me, when I actually transitioned I'm like, I want to find somebody who's better at it than me. That wants to do the things I don't like doing, which is like hiring executives, raising money, even though raising money has not been that hard in the last few years. Um, it's just these things I didn't like spending my time on, right? And this recent transition from CTO to CPO has kind of been the same. Like, there was already people running most of the company under me. And I was mostly focused on like strategic conversations and product vision and things like that. But I'm like, you know, it'd be great if I could find somebody that wanted to do that job. And again, be another peer in the company that can help us do even more. And, and I would say also did it this time, like our new CTO is phenomenal. Um, and it was another way where I could be like, okay, now I can focus on this other thing.
Burnout, Career Highs and Lows -- David Cramer: And the way I've always thought about this over the years, because people talk a lot about burnout and stuff and ignoring exactly what that means. Um, the way I think about my career path at Sentry is you go through like highs and lows, right? And Oftentimes, the highs I'm like, I'm like super on, I'm cranking through stuff.
David Cramer: It feels like, like the return on my time is amazing, right? It also feels like I never have enough time when that happens. And the lows, I feel like I'm not doing anything. And I'm actually probably not doing that much work or something like that when, when that happens, you know. And often what I've, I've recognized is when those lows happen, I just change what I'm doing. Like that's how I will like sort of re energize or re engage. I'll like switch projects or I'll choose to spend my time on something else at the company. And I think some of that is manifested in also me, like, hiring folks to do jobs that I used to do, right? And so, you know, I was burnt out from hiring marketing executives, effectively. And so I'm like, I'm gonna hire a CEO and it can be their problem now. Um, among other things, right? And the CTO, I'm like, you know, I really don't want to manage, you know, a 150 200 person EPD org and sort of, like, manage the organization of that. In the sense of, like, managing how we communicate and structure goals and all this other stuff, you know? What I do want to do is run some experiments and still be involved in things like that. So it was another one of those things that just allowed me to shift my focus. Um, and so now I have, like, other than I have a few PMs that report to me, my, my role is arguably not a CPO. It's just, it's a C suite title that I could take on, um, that allows me to still optically have that influence, you know, which, unfortunately, at, like, scale, you need the optics.
David Cramer: Um But it also, you know, removed a lot of my reporting structure. And so, there's a handful of folks that report to me and most of them work on like random, uh, uh, let's call it experimental projects. And so it's not like I'm actually running the product org necessarily or anything like that. And so, and you'll also find this is fairly true with a lot of founders.
David Cramer: It's like, especially when they're CTO founder, CTO is almost a meaningless role. And it's like, it's kind of all over the map what those, what those jobs translate to. Like, our new CTO, so much more, like, technical from an academic's point of view than I ever have been. And, to me, it's phenomenal Strength in Leadership --
David Cramer: . It, like, adds so much more of a strength in that role than I had. Um, but I also think they're, they're a better leader than me, which is, you know, it's, it's a double win in that case. And so, so I always look at it like opportunities that hypothetically get out of some work. But also level up the company. Usually it mostly just levels up the company, and I sell just as much work for some reason What he is up to this days at Sentry -- Tobias Schlottke: .
Tobias Schlottke: So that means that you kind of run your experimental lab and, um, you, you, you think you can, you can innovate a lot still? Or are you able to innovate a lot and influence the features that are actually being produced or delivered? Um, or how is that now?
David Cramer: I think so. You know, when I look at what we're doing, so the, the, There are three organizations that report to me right now, to give you an idea for what I mean by this. I have a podcast, which is basically a marketing investment, uh, called Syntax. Uh, so that rolls up to me. Um, I have the open source organization, which is mostly us just doing thought leadership and spending money on open source products, like giving them money. And then I have, um, this Hack Week project I built called Spotlight, which is like a, it's like as if you took the concept of Sentry and brought it into, like, the development environment so you could just view traces and all this stuff locally. To me, it's super useful and interesting. And I'm like, you know, I could just fund this project.
David Cramer: Like, I could just Ask for headcount, get the headcount, and then hire people to work on it. And so that's what I did. And so I hired one person that used to work at the company, they came back, and they've started working on it full time now. Uh, and there's gonna be some more stuff like that in the future. Why he doesn't code at Sentry so much anymore --
David Cramer: So it's, it's not actually gotten to the point where I'm building stuff, but I do, I do spend a lot of time writing code in my spare time on a side project. And the company does use Sentry, for better or worse. Um, and so I, I wouldn't say, like, I, I don't get a hack on stuff, I just, like, rarely do it at the company. And I think it's usually because within working hours, somehow I find a way to fill my time with stuff that seems to be stuff that I need to solve versus somebody else could solve, I guess, if that makes sense. So like, lots of people can write
David Cramer: code, you know, it's probably more valuable for me to spend time helping on direction and overall strategy than it is to do the implementation, even if I find the implementation very, very fulfilling.
Tobias Schlottke: Yeah. So I, I guess you still like live and breathe tracking and you do it more than anyone else in the company. Uh, and you know the company best. Uh, and you can, you can, every once in a while just innovate, right? You can just run something, which first sounds crazy, and experiment with it, and play with it and get, actually, get budget for it, which is different from someone who starts at, at zero.
Tobias Schlottke: Um, and, and that, that sounds like a, like a nice job still, right? David Cramer: It's, it's good Centring Budget Conversations Around Idea Validation --
David Cramer: . I'm recognizing is I actually think the budget conversation, just as an analogy, is actually a really useful one. To where the point is, I can still give people freedom to do basically anything in product, but I asked one of the teams I believe in this, like, the budget thing is almost a good way to think about validation. So, like, we'll allocate a small budget, which is, like, one engineer, two engineers, to, like, an experiment. But it should stop there. We should be able to validate from there and then go ask for real budget to, like, fund it in an ongoing way, right? And so, as an example, this spotlight thing I built during Hack Week. You know, I sort of Pressured people into helping me continue the effort to get it out the door. Um, which is like one or two people kind of with some spare hours for a quarter or something. And then we're like, look, there's promise here. We believe in the strategic ROI. Let's add a headcount. Okay, maybe let's add two headcount in the future or something like that.
David Cramer: And, and we're trying to do the same in a lot of our, our newer projects. But I, I do think the budget conversation is, it's just a really useful forcing function. In the same way, like, bootstrapping your company is useful that, you know, It's like, will people pay for it? Or can I get traction on something before I just, like, spend a year building something and, you know, put 15 people on the project or something akin to that?
Tobias Schlottke: Cool Developer Marketing Strategies -- Tobias Schlottke: . And how do you think, um, like your approach, um, also, I mean, I guess you learned a lot about developer marketing. Um, what, how would you describe your approach and, and, and why did it actually work? Like, did you, did you experiment a lot or did you just say, Hey, we're building a nicer error tracking tool with a bit more design and just a bit nicer.
Tobias Schlottke: And then that worked out or like, what did you do in developer marketing?
David Cramer: So, I don't think I knew a lot of this early days, and so my general approach to a product is never be, almost like never be satisfied. I am a huge, huge believer in negative feedback loops. Like, tell me everything you hate about what I'm building, because that's what I, that's the energy I need, because that won't tell me exactly what to do, but it'll tell me all the things that are frustrating you, or the friction points, or the objections, and then I can take that and synthesize it into whatever I think I need to do, right? And so, that was me early days, was just like that kind of feedback collection over and over, and kind of, you know, I would say back then versus now is very different in how we did marketing. Back then I think all of our marketing, our growth has always been like word of mouth, for one. So that's still true.
1. Build Personal Brand as Techie --
David Cramer: But back then it was like I would go to conferences, I would speak about stuff, not Sentry. Um, sometimes like sort of implicitly Sentry, I would talk about like how I bootstrapped an open source project into a company kind of thing, or I'd talk about scaling Python applications, or just random technology, right? But that was, that was building my brand. My brand was attached to the company. So that meant people knew I did Sentry at the same time. They knew what Sentry was. And, and the first step in anybody buying your product is then being aware of your product, right
2. Continue with Brand Awareness -- David Cramer: ? Like it's, marketing is almost all awareness.
David Cramer: You know, you can't often force a sale, but if you're present and they know what you are, when they have the problem, they will reach for your product. And so that's how I like sort of look back and analyze what happened is like, they just knew what Sentry was, people had a use, they used it, right? We still try to do that same thing today, but obviously our marketing is wildly different.
David Cramer: We have a lot of spend on search engines and other advertising. We, we have billboards and stuff. We, uh, we do influencers, which is a super useful, at least in some spaces. Like, in, like, developer tools now it's becoming very, very, uh, valuable, right? Um, so. It's all the same though. We're still trying for like, broad brand awareness.
David Cramer: Like, know what Sentry is, know what it does, and so when you have a problem, you will reach for Sentry. And so, same fundamental thing, it's just like, I guess the, the budget and the channels have like, slightly changed. But I would also say, the channels haven't exclusively changed because of the budget. I think, in general, the market's changed over the years.
David Cramer: You know, I think you could still go to conferences and speak. Big brand reputation, super, super valuable. Ten years ago, there was no, you know, influencer marketing or YouTubers in the developer tools space. It was an irrelevant market, you know, let alone something like TikTok or anything like that, you know. David Cramer: And so, I think you always got to kind of be adapting. 3. Be inspired by BEST brands (even non-domain) NOT boring competitors --
David Cramer: And again, I go back to my fundamental view on marketing is look at people that I stole this to be clear. There's a guy named Omar Johnson who was the former CMO of Beats by Dre, the headphone company. And I saw him speak one time, early Sentry career. And His whole analogy was, they were competing with Bose headphones, his whole analogy was, who cares what Bose does, they're not that exciting, what would Porsche do? Or what would a real brand do that you respect and admire the brand of, you know? Like, how would they think about this problem? And I, I, I took that to heart for like, my entire career at this point, you know? And so when I look at like, how Sentry does things, I'm like, well, what would a really exciting company do? Not, what would a boring competitor do in this space, you know
David Cramer: ? Like, I, I think a lot about like, especially enterprise companies. The marketing is not very good. Standing Out, Getting Attention: Sentry's First Billboard -- David Cramer: And so I'm more like, okay, what's like the really, really creative or what's going to be that thing that makes you stand out?
David Cramer: Because half the battle of awareness is just, you know, attention. Like, can you get their attention? And so how are you going to get their attention? You could be a genuine thought leader, like provide expertise. Okay, that's one. You can do something, um, cheeky or controversial even. You know, that's one, right?
David Cramer: Uh, but it's got to be something like that. And so as a, as an example of this, our first billboard campaign. The premise of it was like, a visual of something ludicrous that makes no sense, and it just says Sentry can't fix this. And the first one we did, it was a Minotaur playing Beat Saber, and it just says Sentry can't fix this.
David Cramer: And you're like, I don't get it. What does Sentry do? What is, like, what's going on? Is that a Minotaur? Are they playing, is that VR? Is there something broken with that? And it just makes you ask questions, right? It captures the attention. And I remember when we did that, like, half the company and a bunch of peers were like, How does this make any sense?
David Cramer: How is this, how is this helping Sentry? You don't even say what Sentry does. And I'm like, that's entirely the point. Because you, everybody's trying to sell you on some shit. We're just like, hey, Sentry is the same. If you're curious, go look it up, you know, go figure it out, you know. And I don't know, I, I just like, again, there's lots of ways you can do things. But that is a way that suggests, like, you have confidence that, like, you can capture people's attention and it's enough. And like, an analogy I have is like, I really like Liquid Death. That's a great example of brand marketing, because they're not selling water, they're selling not beer is how I think about it, and their whole brand is like, it's, it's just this like ridiculous stuff. Like, um, I don't even remember, they just have these funny names for products, and it's, it's all, they had a, there's a post from them recently that I'd encourage you to look at if you're into this stuff, where they talk about how, uh, they value sort of stupidity in marketing, in terms of their approach is just to do stupid things, again, because they're just competing for attention. It's like Liquid Death versus LaCroix versus the, you know, 200 other brands of, you know, water in a can. It's like, how do you win in that market? Well, every market looks like that market, where there's infinite competition, you know? And so, you just gotta find a way to stand out. And, you know, building the best product helps, but one thing is never enough in any of these things.
Tobias Schlottke: Having the best billboard ad potentially helps as well. So what, what about having, I mean, we're a tech podcast, um, have a few CDOs as listeners and a few engineers as well Builder. Not Technologist -- Tobias Schlottke: . Um, what, what excites you about current state of tech? Like is, is your move away from the CDO, um, also a bit of a, let's say. Um, the, the, the realization that, uh, tech somehow got boring and you, you can't move the needle enough.
David Cramer: I've never been a technologist. Again, I just like building stuff, and so, I like, I think I like writing code because, It's very different than managing people, right? Like you're entirely in control of, of whatever happens at that point. And so even, even tech was always like almost like a means to an end for me.
David Cramer: Again, I really enjoy it, mind you, but I also think some people are like lifelong hardcore technologists. I don't think I ever was, or could have been that, you know, I, I think I'm just very pragmatic. I just, I'm often like, I want to solve the task. And then I want to move on to the next task. And whatever the solution to that task is, that doesn't actually matter to me. And so, I will say there's challenges with this because, going back to like, if I'm building the thing, I can visualize what I'm trying to build. I know exactly what I want the outcome to look like. It's really hard to communicate that to other folks. And so, that's like a really annoying learning lesson, as a founder, I would say. Um, so, yeah. But again, I think it's just like, what I desired was to build a really successful product in the sense of like, I wanted everybody to use our product. I wanted validation that our product was the best, that it was really good. Um, I wanted to do things in a way that I thought was more interesting, you know? Uh, and that's like the self serve thing, where our approach to like privacy or cloud services or whatever it is, you know? But it was like less coupled to the technology. Like I, I think I'm pretty clever at building technology in the sense of I take a lot of shortcuts and they, generally speaking, work really well. Uh, but that's very different than like building real technology. Like I think I'm, I'm a product person at the end of the day, more than I am like a technology person, even though my entire career was basically spent in infrastructure. And so, it's kind of weird in that I'm in the CPO role now, because I would actually argue I'm probably a better product person than I am truly a technology leader. But there's this weird balance, I think, in all leaders that like, it should be about making compromise over and over and over. You know, it's never about like, what is the, you know, the most academically best solution to the problem. It's like, well, what is the best compromise we can make to get this done? Um, and I think that's where my strength is. And, I don't know, it's, it's, it's all kind of the same. You often hear about like, technologists or people that are like, senior in the engineering ladders moving to management. They'll be like, oh, I actually enjoy this more. I like, the, the people problem is more interesting to me. And I think it's the same thing. It's just like, it's like, there are logic problems in different shapes of like, how do you solve this problem that's in front of you? And I think that's all it was for me. But yeah, I don't, I don't know. It's a, it's always an interesting dilemma, but it's also like, we've been doing Sentry for so long, like, you know, I think the project's 16 ish, 17?
David Cramer: I don't even know. Well, it started a long time ago, right? So I've been at this quite a while. "Academics" and High Demand Skills of the Future -- David Cramer: And I think one thing that keeps people like me interested is new problems to solve. And at least Sentry's core, error monitoring, yeah, you could probably rebuild it, but it's solved pretty well. Like, it's, it's, the problems that, to take it to the next level, are very, very difficult.
David Cramer: They're not obvious, is what I would say. And I'm very good at solving the things that are kind of obvious, where it's like, there's a hole in the wall, well, there's an obvious solution, is to like, make the hole go away, right? You know, it's like you kind of know the different ways you can make the whole go away. And I think that gets harder and harder the more complex and advanced technology gets. And especially you look at these days, um, with the rise of things like a lot, a lot more ML in the space, which is, you know, I can reason about a lot of it, but again, I'm not academic. And it's, that's an entirely different problem space to me.
David Cramer: And it's like, I, I think that is going to be more of the future, right? It's more traditional academic, like, like our jobs are not going away by any means. But I think the people. That are very talented, that have like strong CS fundamentals, are going to succeed even more than they have in the past, you know?
David Cramer: Because we kind of went through this era where everything was just like building simple web properties over and over and over and over. I think that's going to shift again, where that's still a thing that exists, but I think we're going to have a lot more hard CS problems once again in the industry, you know? Because I feel like those Those mostly disappeared. We invented CDNs, they were great. We invented complicated distributed databases, they were great. We invented cloud, uh, cloud infrastructure, it was great. Okay, most of the, the sort of core platform problems are kind of solved. You know, it's like, and they shift a little bit, right? But now the problem is there's a lot of data, and there's a lot of these other challenges where how do you make sense of the data, and they're just, it's a lot fewer if statements is how I would think about it. And I'm really good at writing if statements.
Tobias Schlottke: If and go to, eh? So, um, David Cramer: I guess, JavaScript guy. We don't have goto. Tobias Schlottke: Great. Um, so it could also mean that, um, the, the, the technologist of let's say yesterday, As I count myself to that group as well, it's more like the CTO tomorrow because you kind of learned how to, how to, how to shape things, right? How to, how to instruct machines to, to do what you, what you want, right?
Tobias Schlottke: And that, that middle layer, like that, that infrastructure layer is better. Better built by academics, as you just said, right? By the people who really want to solve a particular computing problem, a particular data problem, and not so much by the ones who just want to get something done, right?
David Cramer: I think so. I think the, the saving grace, actually OpenAI is an interesting, uh, case study in this because I know a lot of folks that work there. Some of them are very academic. Some of them are not academic whatsoever. And it's interesting because one thing I always saw in my career because I was in infrastructure and distributed systems is, Like, there are a lot of these hard problems, especially with distributed systems, and academics had really good ideas, but they were not viable ideas.
David Cramer: They would never work in the real world because they could never scale to like thousands of nodes or anything like this where the cost would be way too high or too slow or something, right? And so you always needed infrastructure folks, like practitioners basically, right? And, uh, I think the split between the two was so wild that almost, the academics very rarely had value.
David Cramer: And I mean academics as in like, pure researchers. Um, it's interesting now because you look at a lot of the LLM and the modern ML stuff, and that's a lot of academics, but they're much closer to practitioners, and the practitioners are much more closely paired with them now. And so it's actually kind of interesting in the sense of I think like, expertise is going to become increasingly valuable in these worlds.
David Cramer: Because both, like both Implementing large scale infrastructure and implementing ML technologies are both hard problems, right? They're not, you know, entry level CS stuff. Uh, but it's no longer, say, like, that the academic is kind of, uh, impractical. I don't know how you describe it, but like, um, I see a lot more value in academics now and technology than there ever was in the past in my career. And so I think that's a good thing, but it's nice because it is paired with a lot of these practitioners and whatnot. And OpenAI's, my example is like, they just have a lot of both, right? They have the folks who will help implement stuff. They also have regular product people because they're building, I don't know, a chatbot or something, right?
David Cramer: Which has nothing to do with AML at the end of the day. And so, so it is kind of interesting to see, again, it's going back to some of this hard computer science stuff, um, but also widening the industry a little bit at the same time Work-Life Balance Insights -- Tobias Schlottke: .
Tobias Schlottke: I'd still be curious, um, like, moving away from tech again, even if we just touched it shortly, um, how did your, your, your, your, Work life balance change throughout the years. I mean, you do that for 15 years now. So I guess at the beginning it was just grinding and, um, I don't know if it in the middle and at the end was also just grinding.
Tobias Schlottke: Uh, so I'd be curious if you still work 60 hours or like how much, how much you actually spend on, on, on working and, and how much that, that mixes up with your private life, let's say.
David Cramer: Yeah, um, I'm not a big believer in work life balance. I think at the end of the day, you find ways to balance your life if you are in the kind of career that requires, you know, a lot of, a lot of your time. And I found ways to balance my life. Like, I don't work, you know, 15 hour days unless I want to. Like, it's probably just because I'm really excited about something. Um, and I haven't for a while. Most of my career, in fact. Even long before Sentry. I will, once in a while, put in really long hours. And once in a while, you would have stuff that just goes wrong and you've got to deal with it. Like, there's an incident or something, right? But, I think the reality is, when people The way I often hear people articulate work life balance is like, Oh, when I leave the job at 5 o'clock or whatever, I, you know, I disconnect from everything.
David Cramer: And it's like You can't do that. It doesn't exist. It doesn't exist in any high paying job in the world, mind you, right? And, and that's fine. Not everybody wants that. But, like, there are compromises you have to make. If you want sort of a high profile job, or a high ambition job, or a high salary job, you're probably gonna have to change how your work, like, fits into your life, right?
David Cramer: And so mine has always been, I will take time off and I'll balance my schedule, and I'll do work when it needs to get done. Um, But as an example, during this winter, like, there were Fridays where I just, like, took the day off and skied. And I was able to do that because I compressed all of my work into other days during the week.
David Cramer: Or, I made up some of the async work over the weekend, or in the evenings, or something like that, right? Like, cause, like, I just always think about, like, work has to get done. Or, like, the stuff has to get done one way or another. But it's usually not so time consuming if you're sort of smart about how you spend the time.
David Cramer: Again, other than, like, a few situations. And so So, I wouldn't say I have a good balance between work and life. I spend a lot of time in front of a screen. Um, and if it's not a computer, it's like a phone screen, mind you. But, I don't necessarily spend all day working. Like, my wife actually probably spends more hours working than I do. But I spend like Sort of more off hours, like working or doing work stuff, right? Whether it's like interacting with sort of community folks or travel for work to do networking or responding to emails at midnight or things like that. I may be like responding to emails at midnight and not have done anything from like, you know, 4 to 9pm or something like that, right?
David Cramer: And so, again, you end up balancing it out a little bit here and there. But balance doesn't necessarily look like what I think a lot of people would expect it to look like, you know, where I can just kind of shut off. It's like, I can't actually ever shut off. It's actually really annoying because going on vacation, I can, I can get away with it.
David Cramer: I can completely turn things off. But if I were to say to, like say, go backpacking for three weeks, I would come back to a mountain of emails that would just, I would be miserable. And so even when I like, like take PTO or something, I'll often, you know, Say when the day's done or something I'll just like go through and archive all the emails that I don't need to deal with, you know Just to make it so I don't have a backlog of work when I come back and that's kind of annoying like I'm not happy About that situation in life, but it's fine, you know And I also think when people think about this like nobody should pity somebody like me In fact, you should say that seems fine because you probably get paid a lot of money because you are a founder of a successful company Right, and and that's again.
David Cramer: That's how I think about the compromise, you know, like I I'm I'm I've been very fortunate in life at this point, especially in like, I made some trade offs to become this fortunate. You know, I guess it didn't actually have to turn out this way. It could have gone the other way. But like, it's a risk you take.
David Cramer: And so, I think, again, I think it ends up balancing itself out. And I think later career, you find more of that balance. Whereas early career, all I would do all day long is write code. You know, whether it's work, side product, anything, you know. I had nothing else going on. Later career, I have a lot more going on. David Cramer: So, I don't know Writing Code and Side Projects -- Tobias Schlottke: .
Tobias Schlottke: What is the last piece of code that you personally wrote and when was it? David Cramer: At Sentry or in general? Tobias Schlottke: General.
David Cramer: Uh, I have a lot of code. I wrote a bunch of code yesterday. I wrote some code this morning. Um, I have this, I'm big into whiskey, and so I have this side product. I talked about this thing that Sentry Dog uses the dog food. I have this like whiskey, over engineered whiskey website, basically. And so I've been spending a lot of time on that, and it's a way for me to try new technology and stuff.
David Cramer: Like, as an example, I spent a lot of time writing like a scraper. It basically tries to create a database out of like, just imagine all the whiskey in the world. And it uses LLMs to populate it, uses Google APIs to populate it, and all this other stuff. And so, I will say I don't regularly write code. I'll go in like spurts, because like, again that high and low kind of thing. Um, I'll just get energized, motivated, something, to do it. But, yeah, once in a while I still write a lot of code. I don't know if I'm good at it anymore or not, it's really confusing, because I, I seem to fight with technology a lot more than I used to.
Tobias Schlottke: Yeah. David Cramer: not sure if that's my fault or technology's fault to be honest with you. Tobias Schlottke: All the whiskey's fault, right? David Cramer: Or the whiskey's fault, yeah. Tobias Schlottke: Yeah, thanks a lot. Lots of fun. So, um, I, I, as a closing question, um, I, I still have a little surprise for you Advice to Younger Self --
Tobias Schlottke: . Um, uh, I don't know if you, you knew, but your, your press team told me a bit about a hidden Easter egg in, in Sentry interface, um, which is called the Time Machine. Um, and, and I, I think you personally built that years ago and it's still hidden, unreleased.
Tobias Schlottke: And, um, I. I kind of discovered that, like, in that pre release and experiment with it for a while. And, um, I now want us to try that, that, that time machine feature. And we now have the chance to enter the year 2013 when you yourself worked as a software engineer at Dropbox, um, like way before Sentry. And we traveled back in time. Tobias Schlottke: Um, and, and, and you actually have the chance to whisper something into, into young David's ears. Um, what would it be?
David Cramer: Ooh, hmm, what would I influence? That's uh, I don't know actually, it's, it's tough. Again, I go back to this paradox state. I, I do think like, my, actually here's, here's the one advice I would have for myself in probably almost every situation in life, and it's like take more risk. Because the risk is arguably very little in most things in life. And even when we bootstrapped, like I could have like taken risk earlier and like maybe save some money or something, started earlier, change things.
David Cramer: Or when I made career decisions, it took me a long time to leave a job. I was unhappy at, for example, take more risks. You know, I was like, Oh, but like, maybe the other, it'll be hard to find another good job or something like that. And so, I don't know. It's, it's gotta be that. It's the one thing that I think would only have positive influence on my life, you know, that without completely changing who I am, I guess.
Tobias Schlottke: Thanks a lot. Good advice. Take more risks. Don't be shy to fail. Uh, David was a lot of fun talking to you and I hope that we, we, we will have the chance again in the future and I wish you best of luck for first entry, uh, in the future and the next 15 years, let's say. David Cramer: Yeah. Thank Tobias Schlottke: a lot. Bye. Tobias Schlottke: Bye.