How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)

Brett: Well, thanks for joining. I'm excited for the conversation.

David: Yeah, absolutely. Should be fun.

Brett: maybe a place to start, like, wh where did you grow up and what were you like?

David: what was I like? It's probably easier 'cause I assume I was pretty similar today. I grew up in the Midwest in Nebraska long time ago at this point I was there till, you know, almost 20 years old and then moved out and have been in SF most of the time since then. and that, you know, I'm almost 40, so it's been quite a while.

I would say I'm more San Francisco than I am Midwest at this point in that I do not resonate with anything going on there.

Brett: But they're nice people, some of them.

David: some of 'em are nice people. Yeah. Fortunately I grew up in this little pocket, not blue versus red or anything, but it's like the blue pocket, which is like the city pocket, so like Lincoln, Nebraska area.

And so it was a little bit more less farmer, more. Not well educated, but like a different persona than just, I live in the boonies and don't have any idea what the internet is or anything like that, you know? And so there was a little bit more of that. but there was no tech whatsoever. And so I'm, I'm a big fan of the echo chamber that is San Francisco.

It's good and bad but, generally more positive.

Brett: I love monoculture

David: Yeah. Yeah. And I'll, I'll take this version [00:01:00] over, I dunno, pick, I was in DC last weekend and I'm like, Hmm. I was at dinner with a couple friends, my wife's friends, and I'm like, yeah, it's weird. Everybody in the city's a lawyer or a lobbyist. And lo and behold, the husband and wife, lawyer lobbyist,

Brett: there you go. And it works the same way except, you

David: Yeah, yeah. Yep.

Brett: engineer, et cetera. But, but so what, what were things like growing up in Nebraska? Like what were you into?

David: Mean, this is a different era. So it I mean, I was like, your typical introvert still have an introvert, but typical like nerd, like playing video games, doing whatever, fascinated by the internet, but working class family. So we didn't really have access to a lot of stuff. And so I, I have these vivid memories of going over to my friend's house all the time to use the computer or like, I. Like seventh, eighth grade timeframe. I would go to school like an hour early just to surf the internet. And this is the era, I doubt half the people know what this is, but like hamster dance was a thing and GeoCities was a thing. And sort of all these, it was like, I guess that would've been around the.com bubble.

But like I'm in the Midwest, you don't know anything about that. Right. And I, I literally had no idea that ever happened. but it was like when the internet was taken off [00:02:00] and it was like wild west and, you know, small. but super, super interesting. And I just remember being fascinated by like, the thing that kind of opened my eyes, it really got me hooked was I had a friend who, his dad had EverQuest and I, I didn't have a computer, I couldn't play it or anything, but I went over there and I just see the dad playing and he's like, I dunno, he's sitting on a hill with some other character players in the game and they're chatting.

'cause this is what you did in these early games. They were just chat rooms and somebody cast like a levitate spell or something. I think that's what it was. And I just see him float. Across, like down the hill and then land on the top of a building. I'm like, so cool. You know? and I like that era for me is like when the internet was like very creative, like there were most problems were not solved, right?

Whereas today, ignoring the AI kind of shift, a lot of problems are already kind of solved and there's like, I dunno, it's different.

Brett: Were you into software engineering or that didn't happen until later in life.

David: I got into writing code, I don't know if it was software engineering. I was big on just like the, the sort of network connected thing. So, IRC was a big thing back then, which is like, you know, previous versions of [00:03:00] Discord, but open. and so I was on IRC. It was just interesting. Like half of it was like, I don't know, doing shit.

I shouldn't like downloading wares or. Script kitty stuff, which if you don't know what that means is like, denial of service, other dumb hacks. And these were not like real hacks back in the day. It was like run a command sent to network payload, nobody had any security, so it would disconnect somebody from the internet.

Just dumb stuff like that. but then also like video games and other stuff going on there. and the client I used was MIRC and I had a scripting language inside of it. And that was kinda my gateway. I'm like, oh, this is interesting. I can make things, do things. I actually looked back at the language, not that if you call it a language, a couple years ago and I'm like, this does not look like programming in any serious way 'cause it's all a bunch of like trigger based stuff.

but then that led me into like, I was into games and then I got into like data mining games and building like databases out of them, PHP and stuff back in the day. And it's kinda one of those things where I think I was good enough at engineering and I was really motivated and I was into sort of the, the thing I was doing.

and so like a lot of my early career was just me hacking together stuff that would take like. Probably the biggest early projects were like, [00:04:00] I'd take World of Warcraft's game files, reverse engineer them to pull out, say all the items in the game or something like that. And then we'd build a database out of those so people could search them on the internet.

And so that was a lot of my early career and it's inherently connected to gaming. And then nothing since then has been so,

Brett: And did you think that at some point you might start a company or that wasn't even a part of the way that you thought about yourself or what you were

David: no. So I think it's kind of interesting because startups are like, historically a more accessible version of technology companies, right? Like I, I, high school Dropout eventually got my GED just to drop out of college right away. different opportunities, right? Like nobody's going recruiting me from an Ivy League school or anything like that.

And so I was always in startups, I think partially because of that. like I was not gonna get a job at Google when I don't know what the hell I'm doing, right. but also I like kind of thrive in sort of the, the freedom and the chaos and all this stuff that goes on even today. it's, it's still me.

And so I just always worked in these smaller companies and, and kind of grew with them and developed my skills with them. And then I was also big in the open source scene as a sort of like, I think the, I really like startup culture plus the [00:05:00] open source scene created a lot of opportunities for me.

And then, you know, Sentry was born outta one of those opportunities, but even outside of Sentry, like every job I've gotten, every real job has been like, oh, they knew who I was because they used my code already. and so for anybody that says open source doesn't give you anything, it gives you quite a lot.

Brett: And what's the story behind dropping out of high school?

David: working class, family, not like parents are very loose. I dunno, it was like one of those things where a school is not very good in the Midwest either, so it doesn't help. And I think it was one of these things where I was just like, that rebellious kid, I didn't like it. there's things that didn't work for me and then my parents were super loose so they just allowed me to do it.

I don't think it's a good thing. Mind you, college, I think it's hit or miss, but there's a lot of value in even like what the institutions go through from a theory point of view. but it was mostly just like a. I have no idea what I'm doing with my life. I'm like, school is not working super well.

I'll probably figure something out. But there was this kid thought, there's nothing going into this. You know, there's no plan. And then I wouldn't call it luck, but there was like opportunity, I was able to like take opportunity to start doing things on the web. And,

Brett: what's the path from high school dropout to like your first, what you would consider real Silicon

David: yeah, so I, I dropped out freshman year of [00:06:00] high school, so ninth grade, I was working at, yeah. I was working at Burger King. I was a manager, which was interesting. I fired my cousin. Yeah. I think I had worked there like two years and they promo, I mean it's, it's Burger King, you know, there's not a lot of talent going on there. But I worked there for a little bit and then I was just hacking around on the internet on the side, right. And this video game thing worked. And, it's like true startup culture. It's like people could build technology. That technology had a need. advertising was easy back in the day to make some money off of, And I just met some people. Interestingly, one of the people I worked for is now the, they started, Kraken, the crypto thing. I haven't talked to the guy in like 15 years or something. but I'm like, I'm small world. and he was doing sort of virtual currency stuff back in the day. So I think he's actually a genuine believer.

And I dunno, it was just sort of opportunity and like you take the opportunity when you get it. So my, one of my first opportunities was I worked with these people and then there's a company called Curse back in the day, big World of Warcraft, scene. And it was like these three French dudes living in Germany were all, you know, 19 years old.

And they're like, Hey, you want to, you wanna come [00:07:00] like work for us? I'm like, okay. and so it's like I had gone from Burger King to like this kind of weird gaming content, virtual currency thing.

Brett: This is like as a late teenager

David: That late teenager. and then I turned that into like this slightly more legitimate business in Germany.

Which I was definitely not living there illegally or anything. and then I actually moved to California with that company to San Francisco for about a year. That was the first time. Yeah. And I actually went back to Midwest temporarily. when I left that company, I was gonna go to New York and I never did.

And then that was sort of the, the cementing moment where I'm like, I should go back to sf. partially 'cause New York, this is like the different era of tech. This is when we didn't get paid money. and so it's like housing was already expensive in sf cheaper than today, mind you. But like salaries were nothing.

and so I was like, I'm like, oh, I'll stop in Midwest, hang out with my friends family for the summer and then I'll go to New York. And then I just extended that stay and extended that stay. And then I'm like, you know what? I need to go back to like sf. It's like all the texts there. I had a couple years that like that I was in, Nebraska and it was like one of those things where I'm like, I recognize the personal [00:08:00] value to me to be surrounded with peers, right?

And, and no matter what anybody says, there's no other place like SF that has that. So. but that, and I think I, I would actually argue like that was the defining moment of my career. I'd already done a bunch of open source stuff, but when I came back out here, I worked for a, a company that was also a startup called Discuss.

But this was like the first,

Brett: that kind of like had a hot streak

David: Yeah, yeah. They were, they were like scale wise, technology-wise. It was interesting, business-wise, we never really got it anywhere, but, but it was like a real company. It was a YC company. Yeah, yeah, yeah, yeah. It was like a widget on the bottom of everybody's website back in the day when comments were a

thing. but that was like a, I think that was kind of the defining moment in my career. I was there about three years, ran a lot of the infrastructure back in, wrote a lot of code, spoke at a lot of conferences. And then, I dunno, I, I always believe like, invest in yourself. And what I mean by that is like somebody wants to pay me to go, like, speak about stuff that I'm really interested in telling people about, you know?

and I get to travel to like a random country, do that, and it's like beneficial for the company. Sure. I'll do it. And then it turns into like, you know, other opportunities in the future. And, so it's just kind of one thing led to another and worked at a bunch of startups.

Brett: what was the path into being good enough as a [00:09:00] self-taught engineer to work on some of those important complex problems?

David: Just blind confidence. I think it is, like software is not that hard. Most days. Most of what we build is, and this is why the code gen thing is fascinating because most of what we build is like really low complexities code, like it's a registration form or something like that. It's not a hard problem.

It's been solved for decades, right? It doesn't really change. and I mean, I didn't know all that back in the day, but it, like the barrier entry wasn't there. It's not like I'm building rockets or, you know, Google's page rank algorithm or, or something really genuinely complex. Most things, most technology if you will, there's not a lot of technology behind.

It's just code. and so like, definitely some of the things I did were more novel at the time. Like I did a lot of like, not academic, but like practical duct tape together, distributed systems type stuff. the data mining of like World of Warcraft. I just brute force the whole thing. I'm like, I could probably figure out what this is.

I had no idea what bits were at the time. Like even binary was clueless. I did not know what binary or hex truly were until I, I did like a, I think I did a, a semester at college, like [00:10:00] a community college. and this was after I was gainfully employed kind of thing. that's the first day I knew what any of that was.

The first day I learned about like CPU pipelines and stuff. And I will tell you, none of that is still relevant to my career, but, it's kind of useful to understand. So, but you can get through a lot by just trying really hard is what I would say. I, I, I would actually say this even today, like when we look for people, we look at people that are successful in our organization.

It's like you, you gotta have like the right, I don't know what it's like, I don't wanna say it's like right IQ or something like that, but you gotta have like the right capabilities and then you just gotta try really, really hard. and the combination of the two, I feel like is most things.

Brett: And do you think people overemphasize capabilities like they are more abundant than they try really hard is more abundant

David: actually think both are not that abundant. I mean the law of averages and everything, but like those combined, at least from a business point of view, from like if you, if you step back, like a lot of what I've done has not been software in my career. It's like I wanna build like a product thing and I kind of understand what my goals with the product and sometimes it looks like software, sometimes it looks more like a business.

but generally speaking, I'm trying to build like a customer [00:11:00] facing thing, what not necessarily monetizing or anything. And I think my sort of looseness with software in that I don't care that much about the academics of it and my aggressiveness with like sort of this ambition, which is like, I wanna build the best thing or the most used thing or whatever the version that is like, that pairs really well the, like started a company.

and I tried to spin up little hobby businesses back in the day and none of 'em worked out, but I didn't, I would say I didn't try that hard on the business and this one just had great product market fit. So, but yeah, I think, I honestly think. Hard work makes up for a lot of skill. Yeah. Like I would say every day of the week it beats skill.

Brett: Your interest in open source began when you were a teenager in sort of the edges of these gaming communities, or like that feels like an important through line all the way back to your first real job.

David: I always try to like figure this out. 'cause you know, you stuff happens in your life and you're like, well, I don't quite know how I made that decision or something. And I try to like think back, I'm like, what? How did I possibly get an open source? And the best I can make of it is like when I started, you download a bunch of stuff on from the internet to stick it on your, like your personal website, your dumb blog or whatever you had going on.

It was like Pearl Scripts and all this. I don't know if it was [00:12:00] actually open source or if it was just like a freeware license or something. What? But it was like, that was the thing. It was just free software existed. Free is in beer. Right. and then at some point I got, sort of like when my career started, was when I started learning Python and, and it was like I, I was big in the community and things like this, and I think the code was just public for all these things.

And I'm like. Why would I do anything else? It doesn't make sense. I'm just building stuff that I want my peers to use. It's like supporting libraries and things like that. And so it wasn't really like, I never cared about like FSF or like the freedoms or anything like that. It doesn't matter to me. like I wanna access the software.

'cause access is like a big deal when you come from like the middle of nowhere. Right. and I don't know, it's just, it, it was almost like happenstance is that that's just the way I began to operate is like I would just publicize like pretty much everything I could and all the companies I worked at basically allowed me to do that.

And so I think sort of just that desire to share my work and that it was like a useful thing to do, and that the companies were very supporting of it actually worked out really well. And, and, and so a lot of my open source, I mean, I had some stuff before I think Python and Jengo, [00:13:00] but not really. And then I just contributed a lot in the sort of third party ecosystem of that.

Brett: Is that the primary way you started to build followership or notoriety just by being prolific or were there other things that you were

David: I think it was mostly that, 'cause I would build all these things, I would talk to all my peers about it. Like the community wasn't that big back in the day. Like even if you rewind, like, so I moved back out here like 2008 or something like that. wildly different era. Like this was when I worked at discuss our office.

It's like 10 people. It's under the GitHub office, like 10 people. we're still not making that much money in the industry. It's much smaller. Everybody's hanging out. Like it's like us, the GitHub people might have been the early Twitter people. Like all these people that are actually like industry leaders now.

We're all just hanging out all the time, you know? really different than it's today. And so I think I was very interested in that sort of, that ecosystem. And then also as part of this jingo thing, which was like up and coming and used by a lot of these big companies, like less so these days, but it was like Instagram and Eventbrite and Mozilla and they were all Python Django companies.

and so I just grew like this following within there, but it was less of a following like you would think of today. And it was more like I contributed a bunch of stuff that people valued. [00:14:00] some people use some of it, some people didn't use some of it, you know. I would say pretty much if you were building a Jengo thing in that era and you were actually trying to do anything of substance, you were using something I had written, not necessarily in the core of Jengo, but like some third party thing, like Sentry was born outta this era.

but I did a lot of, I, I think at some point I kind, I had like 200 projects or something. but there were just like little things here and there. So

Brett: you were writing a bunch of contributed to a bunch of open source projects. At that point, did you start to think, maybe I'll start a company, or up until the moment you never thought about, I would start that then would become what would be considered a company.

David: yeah, I never thought about it until one day I was talking to somebody that worked at Heroku that they were like a PM for the add-on scene at Heroku and they were basically trying to like upsell me to like, Hey, you should launch an add-on of this. 'cause like they're trying to expand the add-on store.

Right. And I didn't quite understand what that meant. I'm like, oh, that'd be cool. I'd make a little bit of money at like beer money. It was like the joke at the time and I knew like Sentry already had a lot of adoption at that point. and even then it wasn't very ambitious. I'm like, oh, that'll, maybe it'll actually make some money.

'cause I had little like, [00:15:00] personal sites on the side that were like, content sites had Google AdWords on them. They never make that much money. and so in my head it was gonna be more like that. It's like, oh, maybe this is a little lifestyle thing and then it'll exist. Do not start a lifestyle infrastructure business that doesn't work.

and that grew and I think as it continued to grow, and especially once we decided like, let's go fundraise, like and that was sort of of like permission to be more ambitious, I guess from a business angle. And then especially the fundraising was like the full unlock because like when we fundraise, that was like my learning moment of like, you do not fundraise unless you can grow this into the biggest thing it could possibly be.

Especially in our case we had. So, we're a little bit different. Like we were bootstrapped as on the business side. we had a couple thousand paid customers, like 600 K or something before we fundraised, or profitable, if you will. But, you know, profitable is that we didn't pay ourselves tons of money and things like this.

and so it's like, well, why fundraise when you've got A a successful, if you will, bootstrap business. The answer was like, do something you can't do otherwise. And so I really like cemented that in my mind. And not everybody at the company did at the time. There were like, like six of us, three in the company I think, and [00:16:00] then three were about to join.

And I don't think everybody understood how serious I was when I'm like, we are growing this into like, the biggest thing it can be at the time. I think in hindsight they were thankful that we did go after that aggressive approach, but it's one of those things that I, I, I kind of equated to the software side.

I always wanted to build like the best thing. And so when you think about like companies you work at or any, any kind of job or anything you do, there's always like a reason you want to do it. Some people don't have a great reason, they're just kind of like, I don't really have a choice, whatever. But like a lot of us have a choice.

So when I worked at discuss, I don't care about comments. I'm just like, oh, it's an interesting scale project. There's interesting technical things to work on here. And I joined Dropbox for a couple years and I'm like, I don't care about file sharing. Uninteresting, right? I'm like, oh, but it's, it's Python.

And I was big in the Python community. The scale's really, really large and that's kind of interesting. And they've got like high notoriety and stuff like that. At a Sentry, it's like, oh, I'm like, oh, I wanna build a really great thing that all my peers use. And then, and then eventually it's like, okay, now I just wanna be the best business because I don't actually get to write all the code anymore.

And so you always gotta find that motivation. and I think that's partially, that's a really hard problem and, and founders of like, keeping that going over many, many [00:17:00] years. 'cause I'm, I've been doing this full time for, I mean, January, 2015 is when I quit Dropbox. even 10 years is a long time, but going into it, you don't think it's gonna be that long, right?

You're like, ah, yeah, startups take like four years or something. the old days. but it was just a lot of like happenstance, I think. And then allowing yourself to be more ambitious and, you know, call it luck. Call it what you will. But like we had great product market fit from the get go. We still had to do a lot of work to unlock everything, but it was like it was there.

And so there's no question on like, could we grow this? unfortunately a lot of decisions we made on the way have mostly worked out. So.

Brett: Was there a singular moment that that things flipped in your brain from, this is kind of an interesting project. We'll see where it goes to, I'm gonna raise money, let's go see if we can build something enormous here.

David: Yeah,

Brett: kind of like a slow build and then I.

David: I think it was slow and like I didn't know anything. And I think this is the hard part about not being connected. And it was like a different era. So when I left Dropbox, I left because it was like two full-time jobs and it was just a nightmare. I was on call for both. I was doing, so my, my co-founder for Sentry is a designer, so I ran the [00:18:00] business side, which to be fair wasn't that complex.

But I did all the software, I did all the ops, you know, I did most of the customer support. And so it was a lot of work, right? And then at Dropbox, I was running our CI infrastructure, like automated testing and stuff, which was also, I had this habit of just taking on a lot. I've never fixed this for what it's worth, but, and so I, I realized this was unsustainable.

And also Dropbox was becoming a very annoying company to work at at the time. This is when they went through like massive headcount growth. And if you've ever been through one of these, you know, like it's just lots of bureaucracy and it's just not fun. if you're a builder, it's not fun. and so I'm like, you know what?

I don't like Dropbox. Whatever. I'll leave. I gotta, I got bootstrap business that can pay my salary. And then in parallel, you know, you know, investors, how they work, it's like, we're gonna go, you know, SDR everybody, we're gonna cold email, like see if we can convince anything that looks like a remote opportunity to raise money.

And I did that and it was a very quick learning experience of like, those people were not gonna give me money. and so, so I, I had taken a few of these casual conversations and they didn't go anywhere. Right? And, and then I'm like, oh, but we gotta raise money. That's what you do. Like, literally [00:19:00] that was the level of ignorance I had around the whole thing.

and to be fair, I don't think people with intention have much more information going on. It's like, how do we decide how much money we're gonna raise? Or any of these other mechanics? It's, it's all made up for the most part. Right. so I didn't know anything. So I'm going through this and. We had just decided we were gonna raise money to build a bigger company.

There was a little bit of a push in here in that there were competitors in the space that were venture funded. We were so much bigger than them, but we were, you know, running barely, barely in the black, you know, it was like very close all the time. And I'm like, well, we wanna hire people. We wanna grow out.

We want to like win. We wanna be the best and we need more money to be the best. I'm like, okay, we can justify fundraising. So we go through this whole thing, pitch a bunch of investors. All of them basically ghost me. And then I, I just had a buddy, Dan Levine, who worked with me at, Dropbox, so he knew who I was, which it turns out is the game like, like just bet on people and know who the people are.

and he reached out and, and so one thing led to another, they invested. And I think when that happened, that, that was actually like very helpful because, having somebody invests one, there's like the confidence thing, but it. The useful thing of, of venture. And I [00:20:00] think the useful thing of a venture partner is like pushing the company to do more than it's going to do.

Like pushing, like, you know, you gotta think bigger. Like, and I, I had this lesson fundraising and one of the things I did like a partner pitch for like a whole group of people. I don't even remember what the firm was, but I think the pitch went okay. At the end of it, they asked me some bullshit trivia and it was like, if somebody offered you it was something like $200 million tomorrow for the company, would you sell it?

I'm like, absolutely. We made 600K at the time. That's the only right answer to that question. And it was like this trivia thing. they were like, well, we don't think you're ambitious enough because you've said yes. I'm like, okay. Anyways, I quickly learned to lie after that. But, that is, that was also an important lesson of like, think really ambitious.

'cause at the time we're like 600 K in revenue and we're modeling out like, how do we get to a hundred million? And I'm like, no chance. You know? And, and I'll tell you in hindsight, everybody at the company, we, we talk about this and we're like, none of us believed that you would get there, kind of thing.

We're just like, we, that is the only outcome. It's like you have to be a big real company, you know? And so when you think that way, you're like, well, it is like, what are we gonna do to get more? Our version was what do we do to get more customers because we're not an [00:21:00] enterprise company, or at least not one that looks typical.

and so it was always like, okay, what's the unlocked? like find more customers that can use our product and then how do we remove any objection they have from using the product? And that that's still what we do today. So, but it was all this kind of thing of like, oh, I can be ambitious here and I've got the funding now to do it.

And, and I would, I would say after probably one year of venture funding, it was very clear we were the market leader. Before that, nobody had any idea. And then probably for the next five years, still nobody knew how big we were. Even today, a lot of people have no idea how big Sentry is

What's sort of your meta observation on this path into building something that has now turned out to be large? Meaning, I, I think that there's sort of the Silicon Valley narrative that the best founders start the company with this huge vision of building a 10 or a hundred or trillion dollar company, and they're gonna go build this massive thing.

Brett: your story is, I think, a very common story that isn't well told, which is almost the product pulled you into sort of being this founder. [00:22:00] And then as you executed it seems like as you're describing it, the opportunity kind of unfolded in front of you, and obviously you willed it into existence.

It's not the common, you know, we're gonna take over the world kind of founding story. And so I'm curious, do you have any meta observations or how it maps to maybe people that you consider starting companies that aren't or anything else like that?

David: This is hard 'cause I invest in a lot of companies and product market fit is a really hard thing because it's, it's not just, is the product good or does a customer want the product? There's so many different mechanics that go into the same, like, is the opportunity actually there is the way you're packaging it, there is like, it's all these micro decisions that kind of lead to things.

And lot of days I think we just got lucky. Now I do recognize the things that are valuable along the way that did help us push, but I think the ideal outcome is, so here's a mistake. I think all founders, not all majority of founders make. And you know, we know the SaaS majority founders fail. Maybe this is related and I, and I'm just purely anecdotes from the companies I've invested in, and some of them are like [00:23:00] well-known logos.

so they are what you would consider a good investment. Venture capital is not about building technology. Maybe some people would say it is, that's fair to disagree with me. But like, but you raise money to build a business. First and foremost. It's not charity and there's nothing else. You're not giving goodwill to the world with your technology. Some people might, and that's great, that's a like a secondary benefit, right?

But venture capital builds a business and so many people are not thinking about it every day. At Sentry, I would run this script, this is even pre fundraise, that's like, what's our MRR and who are the 10 newest signups? Or something like this. And eventually we automated all this. But like that was the world we lived in was like, how do we get more customers every day?

And then that translates to, well, what are we gonna do to unlock that in the product? And people just don't think that way. And, and I think the other mistake you make particularly, and this is bootstrap versus venture, which I think is complicated. but when you're bootstrapped, you don't give things away.

It's too expensive, right? We had no free plan, like when we started Sentry. Now I don't know that if I had venture capital and I was building a product, I would make that same decision for what it's worth. But eventually, when we [00:24:00] did have venture and we had more breathing room, we did have a free plan.

And that was just the like. Unlock even more of the tam, right? It was like, grow the funnel even more, cement ourselves even more. but again, we were so like focused on like, we must make money like every single day it has to be money. And you, you get that outta bootstrapping something, right? And so I just think like, if there's only one thing that anybody would take away from this is like build the business right away, like monetize right away and then recognize if it's not gonna work or not.

And I think that comes down to like figuring out how you would reason about your tam or whatever, right? And I dunno, you can basically turn anything into a hundred million dollar business these days. Like the technology's really big. The, the world's really big, you know? as long as we don't figure out tariffs on technology.

and so I think you actually don't even have to think that hard about like, what industry am I am in or what industry am I in and is there a tam here? It's more like, no, it exists. There are no new industries. Generally speaking, you can, you can debate on the AI space, but generally speaking, there's not new industries.

There's just. New versions of the same industry and Sentry was in that we were, we knew we were in the a PM category, like New Relic. [00:25:00] I don't think they were a public company at the time, but they were already big. They were well known, right? a lot of companies were big and well known. And so it's like there's a known tam.

You don't have to think about that. And you shouldn't, honestly. But it's like, well, how are you gonna extract sort of the maximum dollars per, I dunno, person you employ or something like that. And our version was just like, well, we want every company to use it. We're gonna charge a low price point. That means we need literally all of them to make money.

and then we're gonna make every version of compromise along the way that allows that to succeed. And so for us, that was things like, okay, we have to support every technology we have to support the biggest technologies. Most and foremost, we have to support web because web is founders and emerging technology and stuff.

And on the counterside, we said in countless times in my career, we're like, we're not gonna do that. even today, I will tell you at the company, we deprioritize things like Java or.net as a technology stack because most companies are not starting a new project with Java or.net or a bunch of these old languages, right?

It doesn't mean they're not valuable and not well used, but like they don't fit our narrative. And so basically, like I would say the, the one strength I've had over [00:26:00] the years is I am like unwavering in my blind focus of like, my only goal is everybody uses the product and we're gonna do everything we can to make that possible.

And I, I think that was very, very useful. but so that, that was like part one. But the other part is then you also have to like charge money for it. And I think usually what I've seen often in the industry is, I mean the companies that work connect those together, right? They connect the sort of distribution with the monetization strategy.

And a lot of people have distribution, which are good bets, but then they never figure out the monetization. And that's why I think it's just really important to figure that out right away.

Brett: I think you sort of touched on this a little bit, but sort of that desire to not just build a product but build a business. was that just a function of in the early days, being bootstrapped, like, I, I think if you looked at a lot of founders that looked like you, right? That were prolific and open source, that started to build something that would not come naturally to them.

They would wait and wait and just say, let's get this thing really big and eh, in five years we'll figure out how to make money. It's like, what, what's the origin story of your desire to do that early on?

David: I think the bootstrap helps, but I could argue that, well, we could have just made an open source project, never fun, like never bootstrapped or anything, but [00:27:00] like you wanna make a living at some point. So that's, that's important. But bootstrapping certainly forces a lot of this. Like, no, you have to build a business.

Like if, if you don't build it, and I, even today I still think of venture as debt. I know it's not debt, but it effectively, to me it's like. From the way value works in the company, equity value, it's like you kind of have to get back like this. There's like this payback kind of concept in it, right? And like you've gotta get beyond that for the, the genuine value to unlock.

And so I still think that way today. and I think Bootstrap sort of forces some of these principles in you. And it's not even like, I, I'm actually not like, not pro or con on Bootstrap. I think it's like, do whatever you wanna do. Yeah. Different tools. and frankly, a lot of bootstrap businesses, they usually do not look like Sentry or I dunno where Visco is at these days, but like Visco is like famously bootstrap.

There's, there's a few outliers that are famously bootstrapped and get pretty successful. And then there's everybody else that never gets that far because they get crushed by venture companies. So, but all of them make money and I think that's really, really important. And so I, I think you gotta figure out how to ingrain that, but I personally do not have an issue around should we charge for this?

How do we charge for it? I'm always thinking that way, even to my [00:28:00] detriment in the business. I just surrounded with principles of like, well, what, what's the persona we're gonna, you know, charge for? Why do we charge, when do we charge? All these things. But I just don't, just, a lot of people aren't thinking about it.

They kind of have like this pitch deck. It's like, well, this is how we'll eventually monetize and theory is great, but like theory never plays out. And so I, you know, I I, I don't know how YC works, we didn't go through it. I dunno how a lot of investors operate, but I, I do know some sort of forces like you need to validate with customers.

And we did that at discuss and the business never got anywhere. They did discuss, like, I do not envy the founders because they spent like, I think more than a decade on that company and, you know, they're doing okay in life, but it wasn't like a crazy outcome or anything. And, you know, one, I always look back the, the most important thing, so not all founders are gonna be, you know, later in career, like have had a lot of work experience.

But I think when you have had a lot of work experience, the most important thing I draw on is just like failures or things I see of as failures. It doesn't matter if the company was successful or not. So when I look at discuss, I'm like, well, I. I think a failure was, we didn't focus on a path to monetization.

We had like one customer at the time, like CNN, they were paying for like [00:29:00] SAML or something like that back in the day, and it was like two grand a month or something. Like measly, it didn't matter, right? and they're like, oh, maybe we'll build an ADS platform or something like that. And, and, and so eventually they did try to do that, but it didn't work.

And I think you gotta be really, really aggressive about how are we gonna monetize this? And you gotta be thoughtful too. Like, and I, I would argue the better versions of this, of just packaging and what your product is in general are the ones that are not just like, oh, here's the playbook, let's run it.

It's like, no, let's actually think critically about the way the market works and how we will insert ourselves in a valuable position. And, and then Sentry we're just fortunate. It's, it's like an obvious path to a cloud service. It's monitoring. At the end of the day, you probably don't wanna host it yourself.

It's complicated. It has inherent timeless value, you know, and so I. You, you could have figured that out if you put your, you know, head to it back in the day. Like, I didn't have to like wait 10 years and be like, oh yeah, it makes sense. The business works. You know, it's, it's kind of obvious in hindsight that it should be capable of working and then just execution.

So, and I think the problem is if we had waited years and we had just say, worked on the open source version of Sentry, which is so exists, roughly, it's self-hosted. I don't know. I, I don't think that we ever [00:30:00] would've gotten here. If nothing else, you've, you've only got so much time and so much runway. And frankly, like tech doesn't need to be that good. Like Sentry was just like stitched together out of like, it was good, but it was, it was, it had a lot of compromises and constraints in the system to make it work better, for more cheap. and again, yeah, too many people, too many people are engineers when they should not be engineers.

Like, don't start a company if you're just an engineer. And I think that's like this, again, this goes back to I see a lot of these, these founders I've invested in where they don't actually monetize the business. And I think that too much thinking about being an engineer, you know. And it just, you can't be that way, you know?

Brett: What, what's the story behind the first line of Code for Sentry?

David: This is how I remember it, you know, it's a long time ago. I was in IRC and again, IRC is one of these things that like, there were so many different factors for, for value out of it. And one of the, the places I was in, in I rrc was like a Jengo channel. It was like a Jengo community channel, and I would just help random users in there.

I'd ask questions of other random users. It's kind of the same way we use Twitter these days in a, in a lot of ways. and [00:31:00] somebody's like, oh, how would I like log errors to the database? And I'm like, that seems pretty easy. And so I whipped up like an example and I didn't really think that much about it, but I just like tinkering and, and software is particularly fun to tinker because there's no consequences for the most part.

and so I whipped that up, pushed it on, I don't even know, Google code or something, who knows? Back in the day. and I just kept tinkering with it, like over time, like over the next few days and more and more and more. And I. I didn't quite understand the value prop at the time, to be honest with you.

I don't know if the value prop actually existed at the time because it was not, the idea of putting logs in a dashboard in the way I did, it didn't make any sense. But what did make sense was, oh, I can take errors and these really rich reports of data. And all I did was I basically emulated what Jengo did back in the day.

So I took this product, which I actually really liked, which was like, when I'm working on my software locally and there's an error locally, the amount of information it gave me was like, phenomenal. It was like best in class. And, and I actually argued today most technology is still worse than that. and I'm like, oh, if we're gonna put it in the database and put it on a dashboard, we should make it look like that.

'cause that's really good. [00:32:00] And then I just did, turns out that was very valuable. And so,

Brett: when you wrote this very simple app at the time, did you then start to hear people using it in a few days later? Were you going back and forth with folks in the IRC community or like what, what was going

David: yeah, I don't actually remember because there's like. There's like, okay, I kind of remember how I started and there's a bunch of stuff that just happens along the way because it wasn't the only thing I was working on. And then eventually, like there's some people actually using it and I'm like, oh, that's kind of cool, because I don't even know if, I don't even know what I was doing at the time.

I don't know if I was using this thing though. and eventually I started using it as well and I joined disgust and they were using it and, and discuss was kind this pivotal moment because

Brett: Oh, this was even before you joined? Discuss Yeah, yeah.

David: is the project's like 16 years old or something. It's, it's, it's very old.

but they were using it and that kind of gave me permission to improve it. And I always had this like line I drew for myself. I'm like, if we need this for the company, I will work on it and I will do this stuff for the company. And if I wanna mess around with it for other reasons, I'll do it outside of work hours, which I actually don't even think you should.

Companies should not care about that line. It's, it's value either way. but I did, and like fortunately it was [00:33:00] not good software at the time and they were using it to discuss and I joined and like the first day I caused this massive outage and the outage was worse because of Sentry. It just cascaded the failure.

So then like that second week or third week or something like this, I'm like, okay, let's rewrite it to make it scale better, because I knew a lot more than when I had originally built the thing. and then we kept iterating and improving on it. And a lot of people started to use it at the time. And this is again, this is like the era of like Instagram, Eventbrite, Mozilla, all being on DJ go and, and just very different than these days, small circles of people, you know, small communities.

And so, so we'd always talk and work on random open source things together and, and when, and I was always motivated by people using my stuff in any shape or form, right? And so I'm like, I want them to use my stuff. I'll fix the random problems. You have feedback, let me know. I'll spend my weekends and nights on this.

I don't care. You know? And, and I did that for a very long time and I still like live off of that stuff. I probably am way too frequently on Twitter only because it's a really great channel to get sentiment from people using our product. And I'm always looking for like, tell me what's wrong. Tell me what you hate.

That's the stuff that like feeds me because that's like, it's like this signal. I'm like, I know [00:34:00] you want the thing now. and This is your like, objection to it. And I'm like, I think I agree with that objection. So I'm gonna go remove that objection. And that, that to me is like definitionally how you get a product market fit in.

I, I actually think, like if I were to try to like reverse engineer what founder-led sales mean, it is like, fundamentally that is sales. It's like I've got a customer that has a desire for my product. All I've gotta do is remove the blockers and then like basically harass them to use it at that point. so I still treat things that way and, I think it's, it's a very valuable approach.

Brett: And so you are working on this part-time for many years, and you're spending hours a week, tens of hours a week. Like what? What is the multi-year?

David: It's a lot. so the project started in, must be like 2009, 2010 or something, right. It was just open source for a few years. And then while I was at discuss, the Heroku conversation happened. And that convinced me to spin up the cloud service. I did it over like Christmas, basically like, 'cause like end of year usually not a lot of work.

So I took two weeks off, spun it up. Turns out Heroku was a pain to use, but Stripe was up and coming and you could implement billing [00:35:00] really, really easily. and it also turns out I had to build cloud service, which I didn't quite know going into it. I'm like, oh, I'll just put the open source thing on Heroku and I'll make some money on it.

I, and not have to do anything. so I built this cloud service, added Stripe on it over Christmas break and basically launched it. I think that like next month. didn't charge much money, but, but it was kinda one of those things where the open source thing had traction,

Brett: And

David: it had like thousands

Brett: of people use it. Like

David: It definitely had thousands of people, like thousands of companies I would bet at the time or thousands of, I call, we call 'em organizations at Sentry, so it could be a company, it could be a hobbyist thing, you know.

and like the, the first day we started charge or allowing you to pay for the cloud service, we had a customer. I think the second day we had 10 customers or something like that. And it was all organic. and we charge like seven bucks or something awful. But there was clearly like value being delivered and demand there.

And now the mistake I made this turns out to not be a mistake in hindsight is like all these companies were using sent, and especially when, and this was just organic over time, lifestyle business. We would use the money from sent to pay for servers and then to pay for like, I would travel a bunch for conferences to speak.

I'm like, okay, now I can just like cover the cost of Sentry and sent, you know, and [00:36:00] or we'd sponsor a conference via Sentry. So we didn't really have income out of it for a while, for about three years. In fact, three years later we raised money. And I remember going into this, 'cause I'm a big open source believer in the sense of like, distribution is like a really, really important thing.

and I remember we had all these customers, like every great Silicon Valley logo using Sentry, they're all using it, open source, self-hosted at the time. And I'm like, yeah, we'll just convert a few of them to pay for our cloud service. And like I remember I go to like Airbnb, I go to Uber and there's one big other company.

I'm like, I'm just gonna convince you to use our cloud service or something. They're like, why? No? Didn't happen. None of them ever actually converted to cloud. And there was a period of time where I'm like, uhoh, do I not know what I'm doing? Is this not gonna work? And at least the, the do I not know what I'm doing is probably true.

But it turns out the value there was not converting them to cloud. It was the long tail funnel of what happens over 10 years. And so what we saw were two great outcomes from this early sort of traction we had. One was [00:37:00] people work at Uber and then go work somewhere else and then use our cloud service at that next company.

And so that worked phenomenally for us.

Brett: Uber didn't want it just because they were too sophisticated

David: yeah, yeah, actually at the time they were by for a long time they were the largest installation of Sentry larger than ours on the cloud. And so it was partially that. but like that was a really big deal, right? It's like that creates a funnel, a natural funnel for you.

Zero marketing dollars spent as, as long as you pretend the engineering isn't marketing. But if you don't think about that, it doesn't, you're like, well, how am I gonna monetize? Maybe I need to change the packaging. Like, that would be a naive version and be like, oh, I need to sell on-prem software.

'cause we didn't wanna do that. We wanted to build cloud service. And so Uber would pay, Uber actually did pay for a year for a support contract. And it was a lot of money. It was a big, big contract for us. And we did, we chose to not renew it. And I'm like, I don't wanna be in that business. I don't wanna sell on-prem software.

I don't wanna sell this kind of business. But that would've been the naive way to monetize, right? We had so much conviction, like, no, we are building this cloud service period. Like, people are gonna move to the cloud, it's fine. and so we did this and over time we saw that Uber outcome. And so I, I had no idea for many years that that was actually happening.

Then eventually you [00:38:00] get a few anecdotes and you're like, done. It's enough evidence for me. I'm, I'm good with it, you know. but the other great thing that happened, and I remember going into our, our seed pitches and because it was bootstrapped and we didn't charge much money, there was all these, and it was open source, different era.

You know, people actually value open source now they understand what it does with the tam, all this stuff. but. We did all these questions and one of 'em was like, how are we gonna make money? And I remember this like vividly and I was so annoyed about trivia questions at this point 'cause I'm like, we had more customers and more revenue than like most series A companies and we're raising a tiny seed at like a cheap valuation.

So I am still like of strong belief that a lot of people had no idea what they were talking about in these conversations. And so we go into this, it's like, how are you gonna make money? I'm just mad. I'm like, it doesn't matter if we don't make money, nobody will make money in this industry because we will gut the whole thing.

And that was the entire strategy of like, you know what? It's okay that Uber doesn't pay us 'cause Uber's not gonna pay anybody. And we've just removed that and that's what open source does. It commoditizes the market. You know, I didn't know it at the time. I can look in hindsight and it's clear, but, but the great data is some of those companies eventually convert to [00:39:00] SaaS with zero sales funnel whatsoever.

And so, like, I dunno if I'm allowed to say 'em, but like we have a big, big payments customer. They're an open source company back, they started. And what was cool is they switched from a competitor. Took away 10 or 20% of that competitor's revenue to self-hosted Sentry, didn't pay us a dime. And then I think less than a year later, you know, they paid us half a million dollars a year.

And that was phenomenal. 'cause not only that competitor doesn't exist anymore, most competitors actually don't exist. So we were able to like actually do what we said we would do, is we would remove that sort of the market. and then we got this customer with, you know, zero marketing dollars spent, zero sales dollars spent.

Like they came inbound, like we didn't even know they were running it until they told us. And then eventually we're like, yeah, just let us know if you need help or something. We're not gonna actually do a support contractor help you in that kind of way, but like, if you ever wanna move to cloud, we're here, kind of thing.

and so I think a lot of conviction and early decisions and just seeing those through, but knowing that they were rational at the same time was like super, super important for us.

Brett: On a similar line of thinking, if you go back and try to reverse engineer the [00:40:00] three or five or seven things that you did that ultimately got you into really strong product market fit, which is both kind of the overlap of, you know, providing distinctive value and then getting people to pay for that value, what, what would those handful of things be?

David: mean, right time, right place a little bit. So, and I think that's true in history. Like I listen to a lot of like acquired podcasts and they're fun because these are the people that are, you know, they're the greatest people in the world of what they've done. And every single story, there is a notion of right time, right place, right?

Like, you can't reproduce what they did. But the other things you can reproduce and, you know, I, I think you've gotta, the thing, the things that we did really well is we were really empathetic for customers. And what I mean by that is, you know. I'm like, okay, how do I get you to use the product and do I agree with that kind of thing?

like the price point was a good example of this. Like me just going over the top with how we like support customers and things. And, and it was just, again, I just look back and I'm like, that was just sales. It was sales from like the founder and the engineer, [00:41:00] but it was like, I want you to use my product.

I'm gonna do everything I can to get you to use it. You know, and I'm not gonna say no. And that's easy with like small companies. It's hard if you're like going after like banks, like they're never gonna do that. But it's like most people are founders, you know? It's, and, and that was always our market is like, get in early, get into these small projects.

And so I actually think that is the only thing that mattered is like, I was just so driven to get these customers to use the thing I had and right time, right place, whatever. I had built a thing that actually was usable. and so if you have not done that, I don't have great advice 'cause I've not yet repeated that or we've not yet repeated that Sentry.

We have some stuff that looks promising, but like, I, I would not claim we have product market fit on, on the rest of our suite yet. and so I think that was, that was really, really important. So one, just try really hard. two, I think people always talk about this, but I don't actually think they know what they mean.

you gotta like say no to things. And so I'll, I'll give you an example. There was this insurance company. Actually I'll give two examples. These is great 'cause both are now customers. one was, I dunno, big Best Buy, I don't really care. it was Best Buy and they sent an RFC long time ago and I'm like, I don't even know what an RFC is.

And [00:42:00] I think I quickly looked it up and I'm like, I'm not doing this. This seems like a lot of work. It was not. And I had also then gotten advice to validate that it's unlikely we were gonna win this anyway, so don't waste the time. But I didn't wanna do it, so I just chose not to do it. And that's my personality.

I don't do things that I don't wanna do. I'm like, this does not look like the, the best spend of my time. I would rather get 10 new customers instead of Best Buy. And it wasn't optimizing for dollars, it was optimizing for traction. And so I said no. And so that was a really important note. there's another customer and insurance company that wanted us to install any virus for compliance reasons on devices.

And I'm like, I'm not gonna do that. And I said, no, they did not be, neither of them became customers at the time. Right. Both of 'em are now customers and we do not run antivirus and we do not really. Now, we might do RFCs now, but not really. and that was really important. And, and so that's one version of no.

So you can say no to customers and it actually really, really is important. same thing with the on-prem support stuff I wasn't gonna do on-prem, but that on-prem thing also required to say no internally because we had started spin up a sales team. The easy thing to do, especially back then was sell on-prem software.

It's like, oh, they're running it. They just wanna pay for that. Can we have an enterprise version? [00:43:00] And this came up every day at the company over and over, I swear to you, for like months from the sales team. And one day I was just mad and I'm like, we are not gonna do that. Never ask me about it again. And they never did to this day.

That was eight years ago. It's never come up again. We're better for it. And so I think this idea of like focus and knowing, like just say no to things that you don't believe in are actually really, really important. 'cause other people are not gonna do that. Like the, companies are driven by. The founders and sort of key executives, but generally it's, it's driven by one or two people.

And so if you don't sort of intervene in all these decisions, whether people like it or not, like the micromanagement kind of thing, you actually have to steer all those decisions and you have to believe in conviction that they make sense with whatever you view in your head is what's going on. And so, you know, I think that is like unbelievably important.

and I think the other, the last thing I would say that's really important that everybody messes up is, and you're gonna mess. Everybody's gonna mess it up. I still will mess it up in the future. it's just like the talent thing is really hard and you just gotta know. It's hard for everybody if like, you're gonna hire the wrong people, [00:44:00] you're gonna have to fire those wrong people.

Your only outcome is like, how do you minimize the consequence of, of messing things up? 'cause you will mess things up and then a lot of other people will also mess things up and so minimize all outcomes of those, or like consequences of those things. and that has been true since the start of the company.

That's probably still roughly true today at the company. you kinda get better over time, but it's just like you gotta accept that you're gonna make mistakes and like. Get rid of the ego and just like, be like, yeah, mess that up. And, and don't, you don't need to take blame for messing. Or like, rather, you don't need to feel bad for messing it up.

You just need be like, yeah, that's wrong. I'm gonna fix it. And so it's almost like an unempathetic version of it. Right. And, and I think a lot of people don't grasp this, especially people at companies don't grasp this. So like, oh, why, why do we make a mistake and not acknowledge, like take personal accountability.

It's like, that's not the point, you know, it's like you gotta make decisions and then recognize when those decisions have failed, fix them and then move on. It's not about like, can we constantly blame ourselves or blame other people or anything? And so, that's like a narrative that I've heard from every kind of industry, every kind of leader in the world.

Like, I went to this conference early on and there was like a presidential historian or something and they were talking about like actual sitting presidents, [00:45:00] exact same mistakes. 'cause again, they're just running organizations. So anybody running an organization has this problem. And I don't know. And, and I say this because I made a bunch of wrong hires and.

Even though this is the, the wisdom you're always given is to like, it's better for you and for them to figure it out fast. We never actually do it, especially early on. 'cause you like the confidence, right? And so there's this, there's this blend you need as a founder, which is like, you need an extreme degree of confidence that looks like ego.

And at the same time you need humility. And like, you, you need to not actually have an ego. And like, you know, I have, anybody that knows me will tell you I am very confident in everything I say, but then I, you know, gave up board control. I hired a CEO to take my job. I hired a CTO to take my job. I should have no, like, I have just full confidence.

I don't need like, the arrogance of the whole thing. Like, and I'm also like very honest about what does and doesn't work at the company and what does and doesn't work for me. And, and so that's what I mean by like, you need to find that middle ground of like, you need to be empathetic towards you know, what matters.

And then just you, you, you've also gotta not like question what you're doing a lot of times. And so, and I, I [00:46:00] think that's hard to be fair.

Brett: What's the source of that for you?

David: I don't know, but I, one, one trade I have seen, and if I could like find this in founders, I would is like, I definitely have like always this thing where I feel like I have to prove myself.

Maybe it's because of my upbringing or something. but it does feel like a lot of founders that are very successful have this like chip on their shoulder of some sorts, right? It's not the folks who are just like, I'm gonna cruise control my way into this thing. So I like, no, I'm gonna prove them that I can do this.

I'm gonna prove that wrong. I don't know why I'm that way. I'm sure I could hypothesize, but I also don't think it really matters that much.

Brett: Are there things that, you were quite strong-willed or religious about that you have since changed your mind and what's sort of the story about those?

David: I would say probably things I didn't understood or stand I was religious about. Some, I have changed my mind. I would say a lot of people just follow playbooks without thinking like, like first principles are really important. And so I. I don't know anything. So I'm, first principle is everything. And, and I have the flaw of if you ask me an opinion, I will definitely give you an opinion.

If you don't ask me it, I might not care. So it kind of depends, right? and so [00:47:00] a good example of this is early on I was fully convinced sales was a waste of time. I am now fully convinced that sales definitely increases our ACV but is not the most efficient thing in a business like ours, or cannot be run, at least in a traditional way.

and so I have changed my mind in like I actually now value sales. But at the, in the same breath, I will tell you sales teams generally speaking at companies are wildly dysfunctional and waste lots of money and lots of time on stuff that doesn't amount to anything. marketing is kind of similar where I actually, I thought marketing was super valuable and I thought it was like this generic concept back in the day and now I actually think it's even more valuable.

But the things I thought mattered back in the day. I no longer think that matters. Like a good example is content marketing I thought was really important and maybe it actually used to be. And so some of this could be just be times changing. And now for me, the things that matter to me, from ROI and Sentry of Marketing are our brand awareness.

Like, we want people to know who Sentry is, or mostly they just, we want them to know that Sentry exists. And so when they have a use, they will buy our product. That's the entire strategy versus, oh, can we [00:48:00] do run conferences or whatever the, like, more traditional versions of marketing are. Those we never like, had great success in.

And, and so I've actually changed quite a lot of perspective on that. and I don't know, it, it's just, it, there's these interesting things because I'm an engineer, and this goes back to the hiring thing of like, I've hired so many marketing leaders at this point, and whether they were good or bad, it is almost kind besides the point.

The programs didn't really function that well in the sense of they didn't really have the outcomes, which I think is a common problem, to be fair. but I've had to go through so much pain with some of this and I'm like, I have to, like, have better opinions about the thing that matters to us. but you gotta be willing to change your mind.

You know? I don't, I don't know. It's like I. There are things you, you should not change your mind on a whim. You should sort of have a reason to make a decision. And then there, there's this quote, I think it's George Carlin or something, but it's like, I changed my mind when the facts change, which I've just latched onto that quote because people will be like, oh, you changed your mind.

I'm like, I never change my mind. But if there's like some new signal that says my previous opinion was probably wrong, yeah, I'll change it like that on a fly. I don't care. Like, because I'm not, I'm not trying to be like, oh, I, have the ego that I must hold that opinion. True. I'm like, that's just what I think right [00:49:00] now based on everything I know.

Brett: someone calls it the, the sort of, the ability to, to let reality tell you that maybe you should change direction.

David: and I think you see that a lot. It's really easy. We see it in politics every day, right? Like, whatever the flavor of the week is, everybody just goes that way, you know? that may not even be their opinion. It's just the one they spit out publicly. And I, I dunno, again, you gotta have the humility to be like, that opinion is wrong.

Like, you know, this information tells me I'm wrong. And for some people that's tough. particularly like employees. Like I think the people that have succeeded at Sentry are the ones who are willing to challenge opinions, be like, no, what, what about with this information? because the, the counter version is you just end up with decision paralysis and you, or you just make decisions based on nothing, you know?

And decision paralysis, in my opinion, is like one of the worst risks of

anything, you know, indecision in general.

Brett: I wanna go back to the decisions you made around what we're gonna build and how we're gonna monetize. and where did like the philosophy of the product and distribution and business model come from? I. 'cause as you describe it, it sounds like it's a little bit, there's some tension between that.

And [00:50:00] we wanna make money and we wanna make early money early on. And so when you talk to an enterprise company and they'll pay you $700,000 for this on-premise, on-prem version of the product, like there's a lot of things that would make it feel like it's intuitive. Okay, they're asking for it, they'll pay for it.

Let's go build that. what was like the origin story of the philosophy that gave you the confidence to say, no, we will not do that and we will do this and no, we won't do that thing, but we will do this

thing.

David: it's tough to say. So I think the core of it is I have a measurement of if I think a company is interesting or cool or. Forward thinking whatever, whatever version you wanna paint of that. And I'm like, if I don't think your company is that I actually just don't care about your opinion or your team is that, or you are that or something.

I'm like, oh, if you're a random person, I say you're a random sales exec and you wanna tell me how sales works and I disagree. I'm like, and you work at some boring company. I'm like I got nothing to like counter this. Don't care. I just don't trust your opinion. And so when it comes to product, I'm like, I actually don't care about what the insurance company works 'cause they are like such an irrelevant technology company in the world that I'm like, they're not my peer and [00:51:00] I'm looking to make my, or get my peers to use myself or people I actually like respect and are building the next generation of technology.

And so I think that's part of it. And that was like implicit. I didn't, I never really thought about it, but I think that's what it's, and so it's like I respect your opinion so I'm going to build the thing you think we should build or something that solves a problem you have at the very least. and certainly any insurance company was not that.

And so I, I think that's one. I think beyond that, We had data that showed it was working well enough. What I mean by that is we were doubling customers, you know, year over year revenue, we were always missing goals. 'cause all revenue goals are basically based on some kind of sales forecast.

And when you have a selfer business and a bottoms up business, like you can't control sales at all. Even today, we can't control sales at the company. and I think today a third of revenue is sales, which is not that much at our scale. Right. it's a good and bad problem, but from a strategic value of the company and our foothold, it's a very, very high valuable thing from a can we have predictable revenue growth and create demand.

Okay. That that's the, the negative to it, right? But all I wanted was all my peers to use. That was the single motivating factor. [00:52:00] Not business, nothing else.

Brett: And that desire was just a personal desire. It was not particularly strategic. It was just, it had nothing to do

David: yeah. That hundred percent. It's what I wanted. I'm like, I would enjoy my, and this is what I tell people is. You start a company that the only reason to start a company is because sure, you can go in and be like, I'm gonna get rich, blah, blah, blah, blah. And maybe that's a useful motivating thing. But I think the real reason to do it is control your own destiny.

Like, and most importantly, you're gonna spend a long time at this company if it's successful and you want it to be successful. So do it in a way that you value, that you want do it. My version's like I want everybody to use our product. I didn't even, it wasn't even like a conversation or a thought. I'm like, that's just the version of me that exists and then I'm gonna make every decision that keeps that true.

Even today at the company, every decision that I push like very hard is coupled to that thing we've written in our corporate values of like, we are a market share company. 'cause that's what we want to be. Not 'cause it's the best or the easiest or anything like that. Just like that's what we want to be.

And just like you can probably extract a real business out of anything in the industry, you can in most things create a business with sort of any different [00:53:00] characteristics of how to approach it. So like you can build a market share company in an enterprise space, right? Like that's what we've done. and.

A lot of everything else was just like reverse engineering and figuring out how do our decisions connect to each other. So for example, open source, it was open source before as a business. So how does open source relevant? Should it still be open source? And we're like, well, we like open source. We believe in it.

And it's technically not open source anymore, but it's, it still has a lot of these freedoms. So we're like, okay, how do we make that to our advantage? Because we don't want to, we're not gonna change it because, you know, maybe we don't extract the most money. We're like, well actually Yandex uses Sentry.

They can't pay for us. Does that help us? Doesn't hurt us. You know? Or companies in China use Sentry. They can't pay for it. They self-host it. Same thing. Does it help us? Doesn't hurt us. And at least from the strategy of like, if we don't make money, nobody does. It helps us from that regard. and so a lot of these decisions, we can now at least associate with that same goal.

Like, we did this because we wanted people to use our stuff. And that was the same reason I did open source. Right? And so, at the very least, I, I, I would say the, probably the one thing that people. Have well understood about our business internally is like our desire is to [00:54:00] maximize the number of people using our technology.

Brett: how is that not at odds with these old stagnant insurers? it almost sounds like you want to get a hundred percent market share for companies that you admire, or startups that you admire.

David: about it, like the long tail. It's like, where's the biggest block of customers? Oh, it's like the people writing new UIs and JavaScript.

They're not those big enterprise customers, even though they exist in there. It's like, okay, that's, I can get like all of this. FedRAMP is a really good analogy here, right?

FedRAMP will be one of the last things we ever do. Or maybe China, one of these, one of these really nuanced, complicated things to pull off that takes lots of resourcing. Last thing we'll ever do, because one, the bucket of customers is smaller, not the dollars of the customers, but the bucket of them is smaller and it's a pain in the ass, right?

And so I'm like, how do you not do the work that is not gonna service that main goal first? And even back in the day, it's like, I was not optimizing for dollars spent. Now you, you gotta balance this. Of course you need to make money, but. But it was always like, how do we get the customers and do we agree that those are the most important, largest segment of customers we can get right now?

there were just so many versions of this in history where I'm like, yeah, we don't need those customers. Like all the on-prem, like I, I went [00:55:00] to this because like, investors will kind of help you try to help you generate leads, right? Which we have never been able to take advantage of. But I remember going to a dinner and I was, it was like a CEO's dinner and I was supposed to sit next to somebody, our investor put me there, and for some reason I ended up sitting next to somebody else.

and so the person I was supposed to sit next to would've bought cloud software. Totally good. The, the person I ended up next to was a banker who refuses to believe in the cloud. This is 6, 7, 8 years ago. no chance whatsoever. Would they ever buy Sentry while that person's employed? I'm like, that's cool.

I'll come back when you're no longer employed. I'll come back when your bank has failed. Or they've hired somebody that understands the direction of technology and that works. Like patience is a really, really important thing in this, right? And venture capital to some degree does let you be more patient, right?

Because you've got that. Safety net, you've got capital. You don't have to pay tomorrow's paycheck with what you're making, you know, today. obviously that's it all there. There's a counterbalance there. Everybody, like you still need to achieve that growth and whatnot. but I think that that was fundamental.

It is like it's a waiting game. We will eventually get there to every single [00:56:00] customer, but we're gonna prior, like we have like this almost implied priority of who matters most and we're gonna get all the people that matter, and then the next people and the next people and the next people over and over and over until we saturate the whole thing, which will never happen.

But that's a great problem to have. And it's like, again, I'd rather go after, you know, the 80% of web developers than we're doing game consoles right now. I don't know if it's gonna be successful for us. I don't know if we can monetize it. I don't know that there's that many customers that will pay. And I'm like, well, we got everybody else.

We, we've got all the low hanging fruit, I guess, of everybody else from a segmentation point of view. So I'm like, I guess we can go after game consoles now. Much more expensive to develop. You gotta have partnerships. Half of it's closed source. So there's like all these complexities, right? I would not have wanted to do that 10 years ago and I, in fact, I would've said absolutely not.

It doesn't make sense for us.

Brett: how do you define product market fit, and what is the moment that you felt like you had it?

David: My, my version of product market fit is when a customer like emotionally viscerally reacts in a positive way. And what I mean by this is like, here, here's the counter version. Oh, that seems useful. Not runaway. Like either the customer's wrong, the product is useful, something's wrong there, but it's not clicking.

There's, there's no emotion behind it. There's no [00:57:00] excitement. Like impressiveness, you know, and I'll, I'll give you my version at Sentry 'cause I don't know when I knew for a course Sentry, but what I will tell you is like we have this new tech, we're using the language models and what it does is two things.

It generates a root cause analysis using all of our data streams, which are pretty intertwined. And then it generates a, a, a potential patch for the fix. Right? Ignore the patch thing. 'cause that's what people latch onto. The root cause analysis was like the first thing I think ever at Sentry where I'm like, holy shit, that is amazing.

And, and it started because I had this belief system. And so I'm like the ICP to believe in this. So I have this belief system that says the reason senior engineers are valuable is because they have domain experience at debug systems. They can theorize how it works and get to a solution really, really fast.

And that was always why I was a value added companies. And this thing took something that I could not grow, I could not comprehend about my own code with had such little detail and it nailed the answer. And it nailed it in a way where I thought it was wrong. And then the next day somebody reported the problem to me and I'm like, oh my God, it was right.

And I like, and my mind was [00:58:00] just blown. And then somebody else, like similar timeframe was like, had the same like emotional reaction, but I was like, I just wanted to tell everybody. I'm like, and that, that's at the, and this is why I love Twitter, is because it is this channel where people want to talk to other people about stuff.

And you can see it like in real time live and all this stuff, and. I knew we had something here. Product market fit aside, there's something there and there's obviously like, well, can we make money and all these other things out of it? But there's something with the thing we're building that impressed me so much that I wanted to tell everybody else at the company that it was impressing me so much, you know?

And then two, three other people over the next week did the same thing. And Mike, there was something here for sure. And I've never seen that before At our company, it's usually like, yeah, we kind of have a thesis in the space. We're gonna build a thing that roughly looks like this. It'll probably be good, it'll probably make sense.

And we're like, eh, it's not quite great. You know, where did we go wrong? And that's usually the challenge of PMF, right? And the, the solution isn't like, can I go ask customers what they want? It's like, I don't know. It doesn't really get you that far. And so you, you kind of have to have a vision behind it.

And sometimes you get lucky, you know? And I think Sentry was, we had a vision for what it should roughly look like and how it should be low friction [00:59:00] and all these other things. But we got lucky in terms of like the domain matter. It nailed the problem use case. We could apply that same thing to many other customers.

'cause like the, the core version of Sentry, the air monitoring component does not look that different than it did 10, 15 years ago. That, that is not a common thing. You know, like most things, it's like, okay, this will get us in the door and then we gotta build this or, you know, some other, you know, shtick or change the technology to work differently.

And we've never really had to do that, which has been really, really high value. So,

Brett: And you think you attribute that more to luck than anything else?

David: think so, and you, you can call it luck or just, you know, trying lots of things, you know, eventually you kind of get it right. but, because I, I'm like, I, I'm not like a person that's like, oh, you get lucky. It's like, well, you kind of, you know, there's a, the saying of like, you create your own luck.

I believe more in that. It's like, I built lots and lots and lots of stuff. Eventually something had to be useful, and have a packaging model and all these little things that work for it. And so I, I think it's that. And, you know, if I ever figure out how to like recreate PMF in products like scientifically, I mean, if anybody does, [01:00:00] it'll be most successful business of all time.

Money is usually not the hard part of a business. like getting capital or even charging people money is usually not the, the trickiest problem,

Brett: Maybe on this point. Why do you think is so hard?

David: I can tell you, I, I see things that people make mistakes on and sometimes I build for themselves when that's wrong, I always build for myself and I still consider myself like the, the target customer for Sentry.

Which is a great position to be in by the way. Like, if, if you can nail that where you are your own customer, it makes everything easier. But like a lot of people don't have that, right? Like, you're like, oh, I'm gonna go build finance software. I'm like, I'm an engineer. What do I know about finance software? And that, that's hard. And those are valuable problems, right? And so given that, I think you often make the mistake of like, you don't actually know what the right, who the right customer is and what they need. Because most conversations are like, oh, that seems interesting. That seems, that seems useful. And that's like such bad feedback from like a customer.

And that's the common feedback you're gonna get, right? And what you want is like, I want that, but it sucks and this is why it sucks. Or like, oh, I really wish I could use this, but I can't because X, Y, and Z. [01:01:00] And I think some people fail to find those customers because the thing they're working on just isn't that important.

Like there's just not enough value there. There's not the ROI calculation, right? And I think that's even true in some of the stuff we're building today. Now I'll tell you, lots of businesses build stuff that has very little ROI and they make lots of money on it. So it doesn't mean you can't monetize it.

Like our, we have this tracing product. It is, you know, I know something, it's at least 20% of our business at our scale. You would call that like at least a good entry level success. And I would tell you, I don't think the product is very good. I don't think it remotely has PMF and more. So I would tell you, because we're in this distributed tracing space, I'm not sure distributed tracing is a future technology that will be good.

Yet if you look at Sentry, we are so invested in making it successful and building all these things because you gotta try, you gotta run, run these experiments and whatnot. And my version of that, I think is I just built lots of developer tools and lots of stuff. Sentry happened to be one that actually had sticking power and had all these other things.

Right? And I think that's what everybody does in, in startups, right? Is like trying to figure it out. And I don't know, [01:02:00] the, the tough part is like no matter what, you've got a limited time window because you've got limited money. you often overextend the time you're willing to focus on something, but at the same time, if you don't actually focus on something, how are you actually gonna signal that it won't succeed or it can't succeed?

to some degree, I think founders get a little lucky. Like there are certainly people with networks to leverage and they can push distribution. 'cause distribution is the thing that has no luck involved. There's a reason 20% of our revenue comes from this product it's because we have distribution, not because it's the greatest product of all time.

Right. And that is the reason, you know, IBM still exists or Oracle or any of these companies. It's like they just have distribution. They can just sell stuff. It doesn't mean it doesn't matter if it's good, right? and if you don't have distribution, if you don't have personal distribution, like personal brand, celebrity, okay, well then how do you do it?

I think maybe it's luck. Like it genuinely might just be, well, you've got a limited time window. And so then you're like, well, if it is luck, what can I do about it? I think that becomes the immediate next question. And then I think you gotta look like where are my personal competitive advantages?

You know? And mine was like, I can ship code really fast. You know, I can, I can do a lot of stuff on my own. and so I'm gonna use that and I'm [01:03:00] gonna turn it into something.

Brett: so if, you kind of poke at the, tracing product, and a lot of people would say it has product market fit in your definition, it doesn't. Maybe you could talk in more detail about like what is the gap between what is going on with that product and what you would define as really strong product market fit.

David: So I wanna give an anecdote for why this makes sense. So nobody roast me. I was talking to Microsoft a long time ago, strategic partnership and. They had this Azure, or this was the era where everything was Azure. Every department had to funnel money to Azure in one shape or form. So they're just chilling Azure no matter what they do.

Right. But there was one department that did like visual studio and.net that did not have this agenda. And I'm like, and I was talking to the CVP and I'm like, help me explain how your KPIs, developers and every single other organization has to be. We make Azure money. And they're like, well, once upon a time, we did just enough research that said more developers translates to something like more dollars in the work.

Like whatever it was, some loose theory. And I'm like, good enough for Microsoft, good enough for me. And so I, I don't know [01:04:00] if I take that to an extreme, but I'm like, all I need is like where there's smoke, there's fire and, but in like a positive way. So if, if there's something that says something's wrong or something's good and I agree with it, I'm like, done.

I don't need ample amounts of data to make this decision. And so, and this is why I love, and I, I hate what like Twitter has become, 'cause it's kind of a disaster. It's filled with boss all this stuff these days. But like, I've not found a better channel that just, that is that passive thing of like. I get genuine feedback.

And, and what I mean by that is like when you think about product market fit, and the reason I don't think our tracing product has it is because one, I don't actually think it's great yet. And so I'm not impressing myself with it. And two, I don't see a bunch of people on the internet who are real users.

You might see like derell people or marketing people like India developers, like whatever. but like I don't see a staff engineer. I respected a real big company being like, this is so fucking good. You know, I love this. When that happens, you've got it. Don't think too hard about it, but there's something there.

Just latch onto it and, and build. You may not have the tam, who knows, but like, that's what I'm looking for. And if you don't get that, I don't know. It's just not there. And, and, and people always claim it's like, oh, [01:05:00] it's marketing. They don't know about it. Blah, blah, blah, blah, blah. But like, marketing's not our problem.

Like lots of people know what Sentry does. They'll find this stuff if nothing else. And so I think people lean on some of these things too much. They'll be like, oh, well the reason we don't have more customers is 'cause marketing. I'm like, no, you just don't have more customers is because it's not good.

It's not useful. Not, and, and, and it, it could never be useful. Or it's just not useful yet. One of the two is true or something like that. Or it's too high friction or, you know, something. And I think the, challenge probably, and to be fair, I've not tried that hard at this 'cause we have like known tams that we operate in is like, is it never useful or is it just not useful yet?

Like, understanding the difference between those two is like, that seems like a really important question.

Brett: Wait say more about that.

David: Well in the sense of like, are you building something that just has no opportunity and, and like kind of stepping back and saying like, okay, let's actually look at the ecosystem. Is this gonna be a big market?

Can it be a big thing? Is it like, is it just never possible or No, the market's definitely there. I just haven't figured out how to sort of get into that market and differentiate and sort of capture that like, emotion from people yet. to be [01:06:00] fair, I think a lot of it's the latter of like, again, like I said, I think most things, there's like a real tam in these days.

but I dunno if you're building like a to-do app. There's an easy calculation that's like, how is your to-do app gonna matter in the world whatsoever? You know, kind of like, you can find some of this in, I think certain things or like the, the content. Is this a feature argument? you know, like given I was at Dropbox, there was that famous thing where, you know, apple said Dropbox was a feature.

And I'm like, I'd agree it's a feature. You know, it's like we don't even pay for Dropbox anymore. We just use Google Drive 'cause it's free. You know, it's not a great place to be in as a company, but it doesn't matter. 'cause as long as you can get a foothold and get distribution, you can turn that into something else.

And so, even though I would largely say Dropbox looks like a failure from the outside, like, or to me from my point of view of like, they haven't really done much. they make a lot of money and so it's a successful business. You know, just like IBM somehow is still a successful business, as are most of these sort of, I guess ancient enterprise businesses.

So, so I, I think there's a lot of ways I guess you can skin the cat if you will. but I do think when people are early stage, I. The challenge is just like recognizing [01:07:00] if there's actually something

there and figuring out why it's not working and being really aggressive about that every single day of the week.

Brett: I think to your point, the thing that I've noticed that's so particularly difficult is the mild interest

or kind of using it. Yeah. This is helpful. it would be so much better for most founders if people just said, no. I have no interest in this. I think what you're doing is horrendous.

It's completely useless. You can't get anybody to use this.

David: I actually agree I, I think there's a truth that we are not honest enough. It's tough, right? Like some people cannot handle the honesty. But also, I was listening to this interview from, who was a guy that run or started a firm,

Brett: max lip.

David: max. It was like him talking about PayPal days and stuff, and he was going through this story about.

I think he was just talking about this time where he was doing more venture stuff and he was just so pessimistic. 'cause he is like, there's no way this will work to like everything. And I'm like, I feel you. I actually believe, like that's true for most things. That's not helpful. It's not productive. Right.

So on one hand, [01:08:00] like you do need that honest feedback because you don't want to have this illusionary thing where you're just like wasting time. You also need a little bit of this like sort of naive, youthful ignorance of what's going on to make really great things happen. And so you, you see this in everything.

Like you hire new grads at your company versus like a 20 year veteran. There's a wildly different outcome between those two humans. The new grads might mess some things up, but they're just gonna do random stuff without knowing what the consequences are, without knowing what it, what it should be. You know?

And I think that's the challenging part. It's like what it should be or like, no, no, this is just how things are Sometimes that that matters and sometimes it doesn't. And so I, I don't know what the answer is, but I, I think there is, I mean, I'm certainly guilty of this with I, my portfolio companies of where I'm like.

Maybe if you just do this or something, instead of being like, maybe you should just not do any of this and do something else entirely kind of thing. The the cool thing is though, at least in the sort of this AI hype wave we're in right now, there is a just a genuine, real feedback you can give. Like if you are not latching onto that, you are at least missing an opportunity.

Like it's a crowded space, but like, it's the thing where everybody's minds are [01:09:00] right now, and so the attention is already there and attention is usually half the problem.

Brett: what have you noticed about what made the market that you're in so good? It, it sounds like you, you, in, in the origin story of the company, kind of the market found you,

right? You didn't zoom out and say, here's 10 different markets I could go after, but like, obviously the, the, and I'm not really interested in the size of the market.

Like what about the properties or the setup or the dynamics of the market worked so well for this business?

David: I think part of it was like people, people were blind and so here's, here's a really important lesson, 10 years ago. We were, it was sort of the, the beginning of this JavaScript narrative we have today where JavaScript's kind of permeated every day and it's all these UIs, these fancy applications.

It had just started, but it wasn't really there yet. jQuery was still a really big deal, and, and this is around the time we fundraise, I'm like, oh, we need a, we need to do more JavaScript stuff because everybody uses jQuery. Then every, again, going to my funnel, everybody can be our customer. Very naive point of view, I didn't look that hard at the space, but coincidentally what was happening was this JavaScript shift [01:10:00] and we started this investment and then we saw that we eyes wide open.

We're like, oh, this is happening. That's gonna be really important because our thing where we want all the customers and everybody's using JavaScript 'cause they have this jQuery animation thing going on now is even better because now they're just building the rich UI in it and it's like, it just makes our property even more valuable because.

Of these attributes, like, oh, it's on a client device. So they don't have servers, they don't have logs, all these little things in there, but we recognize this JavaScript shift and everybody else ignored it. Even today, half these, half the companies in observability, they're just like SRE companies and stuff.

Now they're ignoring it far less than they used to, but we only exist because people ignored the space. Like, and we might still have like grown and stuff, but, but we are dominant in that market and we are first to market in everything there. We are still first to market in everything there best solution.

And that is like the P zero of the entire company is like, we have to solve JavaScript first. And it's because we recognized that was the growth of the industry. And I think 2019, I don't remember where I get the state, I just quote it forever, was, the first year where the, the [01:11:00] number of JavaScript developers, was growing faster than any other market.

And it was the largest segment of developers already. And I think that's been true every single year since then. That's a really big deal when you're like, how do we get most customers? And again, so I just think people didn't pay attention. 'cause they're like, oh, enterprise customer says I need this and, you know, X, Y, Z and they're always asking for things that are in the past and I don't care about the past and this is why I don't care about Java and stuff.

I'm like, I care about the everything else we're building in the next 10 years. That's the important investment. I care about the banker that is gonna use the cloud, not the banker that refuses to use the cloud. It's like, and I don't know, especially early stage, it's, it's hard to get in the trap of like, well, I, I need to get like validation.

I need to make some money. But does that align with my view of the world? And I think no matter what, you're probably, you have the same dice world being wrong, but the better outcome is when you're like, does that align with the view of my world, in the future versus in the past kind of thing. So,

Brett: you're the sort of, one of the dream setups and there's probably a handful, is there's just enough people living in the future to sort of bootstrap the back of your company until the future happens.

And if there [01:12:00] aren't enough. the company doesn't work, and it might be seven years later that the future happens, but the company's already dead.

Like you need just enough people living in the future that gives you the time for the whole rest of the world basically to catch up,

David: I think this is why Silicon Valley is like super helpful for building these companies because it is this, call it a pyramid scheme, effectively what it is. But it is like we need the, to build the thing that all the next startups are gonna use. Most of 'em are gonna fail and not pay money, but they'll get venture and that'll buy us some time.

But it's a directional investment kind of thing. And even, even at our scale, I'm very much like, why are all YC companies not adopting Sentry Day Zero? Like I, I am thinking that way. And, and that is so irrational when you think about like, we are an, you know, a big enough business that it's like focused on revenue growth and things like that.

I'm, I'm like, I actually. I could not tell you any of the day of the week how much money we make. I can give you rough, ballpark numbers of how many customers we have and if we are growing net customers or not. And I can probably tell you we're probably missing sales forecasts every, any day of the week as well.

and all I care about is like, are all the new startups using Sentry? And then if they ever [01:13:00] turn, why? And are we accepting of that churn? Because like sometimes it might be like, oh, they had a use case we don't wanna solve, that's fine. You know, other times it might be like, oh, they churn for some bad, some, something we would say is a bad competitor in that they're, the product's not that good or something like that, but it's a direct competitor.

And those were like, how do we have stopped that kind of thing. and you don't have to build it this way. I think it's a better way to build a business, to be fair. And certainly strategic outcomes. It's, it's been better for us, but, I don't know. I, I, there's a lot of companies that are like, oh, we're gonna go do the same.

We've got, you know, five random people from banks, which I assume are just people that, investors invited that are, you know, I, I know how the network works. kind of giving them false hopes and dreams, you know. But there's value in that too. So I, I don't know. It's tricky. My world is all non-enterprise is what I'd say.

I'm a consumer person by trade, that happened to build an enterprise business that I refuse to let it look like a traditional enterprise business. So,

Brett: And it goes back to your idea that there are many ways to build a company, and so just all things equal. Find something that fits you really well.

David: and I think the one layer I put on top is enterprise companies cannot compete with us when we undercut them on price, when we undercut them on [01:14:00] market share, when we are the developer's first choice. It just gives that, it's a better way to build a business, is kind of what I'm saying. And, and there's a lot of stories in history, like Okta's a good one, Okta full enterprise, right?

They acquired AU zero the time was not, it was more like the bottoms up thing, but it's now just enterprise and, and this is just what I've been told by Okta people is like, it's really hard to go from enterprise to sort of that bottoms up self-serve s and v mid-market. It's also really hard to go from s and b mid-market to enterprise, and I wouldn't say we do it.

We have enterprise customers, mind you, but SB and mid-markets, mid-market alone is like, who cares? Like, I don't need enterprise customers. They're just more annoying to work with. Now, there are a few of them. Some of, sometimes it's useful to have less customers because I'll tell you the, the downside to having so many customers is like, because just like a consumer company, it's a lot of noise in the data, so it's really hard to figure things out, but, but it feels more rewarding, I guess.

Brett: you touched on this in, in some different ways, but I'm assuming lots of founders who are starting with some open source part of their business and then want to build, a for-profit venture scale business, come to you and try to sort of get your advice on what they're doing.

Are there things you [01:15:00] haven't touched on that's like part of the things that you're constantly telling?

Those type of those founders focused on that shape of company based on your own experience. Maybe you could share and then just send them a, the link to this so you don't have to keep saying the same

David: I, I've, I've started to blog. So again, going back to that honesty thing where maybe sometimes we should tell people, that's a bad idea. I certainly don't do that. So maybe I should do that a little bit more. I think a lot of people who have useful wisdom don't actually share it because they have ego.

I'm not that I don't care. I actually get a lot of street cred by just being authentic. And so I've actually blogged about a bunch of this stuff too. I would say that like, I don't know, like the, the main thing, the main overarching theme, and this is the theme I apply to myself. You don't know what you don't know.

That's okay. It's easy to kind of get into a, a trap, what I mean by this. So here's, here's one sort of narrative I always tell people that I haven't really touched on. You really have to trust your gut and everything. And what I mean by that is. Every hire that has not worked out for Sentry. I kind, I kind of felt like it was not gonna work out, but I went through with it anyways.

[01:16:00] and I optimize for, I want less mistakes, more, better outcomes. And so I would rather not do something that has a pretty strong chance of failing versus do something that has a smaller chance of succeeding, if that makes sense. I don't know if that's a good thing or a bad thing for what it's worth, people always tell me I'm risk adverse in that regard.

And so that might not be the right advice, but at the very least when it comes to hiring, it is the absolute right advice. Trust your gut on if the person knows or is aligned or whatever. 'cause every single time it seems skeptical. Like to me it's like, it's been wrong, it's been a bad hire and you have to unwind.

and that's in. And so I just think about kind of that and it's like. I talk a lot about brand and, and it's the same thing for me. I'm like, I just want people to understand genuinely how I think about things, because I think I'm rational. I, I, like, I'm thoughtful about my, my process. I don't always explain it, but, and there's a lot of things you learn and you learn them like trial by fire.

You learn them by messing things up. And the more wisdom you can get from other people's mistakes, the better. You can't apply their successes. It just doesn't work. Like great Sentry has product market fit, there's nothing [01:17:00] you can learn from how we achieved it that you can apply to your business. 'cause it was like just fortunate coincidence, right?

But what you can learn is maybe you don't need, you know, a, I dunno, I'm making this one up a CRO when you're 10 employees or something like that, right? and so they're almost like truths that you can definitely apply and you should talk to people who, you know, venture folks are great even though I talk a lot of smack.

Operators are sort of the ones who have lived through a lot of this pain. So you need to talk to operators about it. And again, this goes back to my, my double side then where I wish more successful founders were more, they expose themselves more in the sense of like, it's okay to like just be humble and go like, nobody thinks you're perfect in the first place.

Like, just tell people the pain you've gone through. And sometimes we do this in closed forums, right? But good luck figuring things out outside of closed forums. and so I, I think it's just like, look for those opportunities. Look for that like therapy group, if you will. I never had it like when I was a founder and it would've been super, super useful and I don't know, I don't know.

Just are gonna mess things up. That's, that's life, you know, be humble and, and confident at the same [01:18:00] time.

Brett: How do you define marketing what is the role of marketing in Sentry Story?

David: It's interesting 'cause a lot of companies, I think they would define marketing as lead gen or leads because they're just like a traditional enterprise sales company. the way we think about marketing is the goal is here, here's, here's my sort of on the fly thinking behind it. You have a path that a customer goes, like a buying journey of some source, right?

It's like how do you get a successful customer? Yes. There's lots of things that come into play. It's like, does the product work? Does it solve a need? Blah, blah, blah. Marketing is a thing that gets them marketing and or sales. It's kind of hard to differentiate the two in some degree, but like there is this path they go through to get your customer.

For us that path is, they know about Sentry. They have used for Sentry, they'll become a customer kind of thing. And what that translates to us is a bunch of different t. Those tactics for us are generally like brand awareness. Like make people know that Sentry exists and then make them have a clue what Sentry does.

But it's actually two stages for us. and so I, I don't know. I actually think like maybe you could define marketing as like the mechanisms that capture [01:19:00] attention for your product. or at the very least, I think that is a use that is a better focus than what a lot of people do with it. A lot of people just run a bunch of activities that don't really have ROI.

we're at a lot of conferences, for example, we don't get ROI outta most of those. And it's a constant conversation like, should we just like not go to half of these? But then there's like this problem of like, well then our brand is less visible. Do we, do we have a consequence there? So even though we don't get direct ROI do, we get brand ROI billboards are another version of this is like nobody will with a straight face tell you billboards, you know, translate to like demand generation or anything.

But I will tell you, I have lots and lots of armchair anecdotes that are like, I was talking to somebody here and they're like, oh, Sentry, like that billboard that made no sense. I'm like, yes, that's the one. Got your attention. That was the goal. they might not be the ideal customer, but I got their attention.

And then all I gotta do is. Get them to know what we do when the right time happens, okay, we've got them, we're ready for them. And so at least our marketing investments are really about how do we capture people's awareness and mind share and stuff like that. And that comes down to like attention, which is very hard.

Mind you,

Brett: did that look like before you had the resources to do what might be considered more conventional brand [01:20:00] awareness? Like what was

marketing in the first couple years when you actually were working on turning

David: I think marketing first a couple years was more sales. And so what I mean by that is like, I think as sales, it's like when a person is directly trying to talk to a customer, whereas marketing is a little bit more of like a, a broadcast if you will. You can disagree with that. I'm just making stuff up.

early days though, Sentry, I was speaking at a lot of conferences. I was not to none of this stuff. I was going and telling people about, like stuff I had built or how to, how I scale web applications or how I approach open source when it comes to monetization. 'cause I had bootstrap Sentry. I was, creating value, I guess I was giving them something to listen to me that created credibility for me, caught their attention. They knew what Sentry was that East first Sentry, then they bought it, you know, kind of thing. And that, that's it. and so to me it's the same thing I always did. early days, it's just a very different scale and approach and tactics to the whole thing. But it was just like, I, I kind of believe like the way you build distribution is like, brand is like really, really important.

And most technology companies do not invest in brand. And, and it's complicated because brand is a lot of things to us. Brand is mass [01:21:00] market awareness. Brand can also be, oh, I'm selling a security tool to Fortune 500 and nobody else, but my brand is trust. They have to trust me somehow. So how do I create that credibility of trust?

So whenever they think of me that I, oh, I can trust that company so I could buy a product from them. and so brand is just like this representation of yourself. And I think the problem is people get so wrapped up in like building the product that they never solve brand. But the problem is like. You also then still have to have the product that, that will capture a market and, and I don't know, it's this chicken and egg thing where you kind of wanna prove market fit and then you really need your brand to be well known and well established. And you probably should work on 'em in parallel. But implicitly for me, and I think this is true for all startups, like the brand is the founders or the founder,

Yeah, exactly.

And they still are today at Sentry, right. And I'm not in charge of the company, but they are still me, and our marketing is me. Like half of our dumb campaigns come from me and like nobody would suggest them otherwise. Like we just sponsor this like ludicrously expensive thing that is more money than we've ever [01:22:00] spent on a sponsorship by far.

And it was just me being like, let's do this. I'm okay with this risk and then a bunch of anxiety ensuing from everybody else in the company. But like, it's because I inherently believed in that thing and I'm like, this is a good way to represent us. We can tell our story on this. We can do this thing that really pushes this narrative.

Early days, it was like, it was IRC still Twitter for me. it was, you know, in-person conferences, speaking at these conferences and it was just representing myself, which happened to be also my company. So, you know, people like to be cheeky. They're like, my views do not represent my employer or whatever.

They always do. That's the only point like that is, that is marketing is like the people are the marketing engine. A lot of times obviously this changes at like mass scale. like I don't dunno who the people are that run Coca-Cola, but, I actually don't know what the brand means anymore either. but that's true for a lot of things.

I like, I, I think the interesting thing I would think about from marketing that, that startups do not, some sort of, so some startups get this, like Vl Iss a great example of another company that understands brand. but Liquid Death is my favorite, makes no sense company. 'cause all it is is marketing.

There is no product, it's just canned water that has, [01:23:00] like, I just define it as like tattoos on the can to make you look cool or something, but it's just marketing. And then you gotta be like, well okay, what are they selling? You know? 'cause like clearly people are buying it and they're not buying water.

Well, they're buying something else and your goal is to like, sell, sell, whatever that is. It's like your values, and I don't know what liquid best values are, but they're certainly not canned water. They're certainly not. Water in a canned is better than water in a bottle, or our canned water is more delicious than everybody else's canned water.

It's just like they're selling like this sort of vibe, if you will, or this culture or something

else. And, I don't know, marketing, sales, it's like the same thing to me in a lot of ways, especially when you think consumer, or be like, sort of mass market

e-commerce kind of stuff. but I do think that branding is really, really important.

And, and if you are a founder and you're not out there just like representing yourself and your company every day, you're, or as much as possible, you're doing it wrong. And so you still need to charge money. but I think the best founders I know, even if they're not charging money yet, they have cemented so much brand loyalty, even if it's just them themselves as a person, you know?

And, and that will translate to revenue at some as, as long as they have a, [01:24:00] a path to charging money that will translate to money. So.

Brett: Stripe is an amazing example of this, and when you think about like part of the business that I think that most people don't, when you think about, okay, how do you develop power in a business, right? Moats, et cetera. One of them is

brand, but I feel like in B2B software companies, it's the least understood thing. But like I, I believe that Stripe has tens of billions of dollars in enterprise value created through brand.

And to your point, the interesting thing is it just flows from John and Patrick.

it is an odd, like when you think about, well what does Stripe stand for? Or what is the brand? It is them.

David: Well, think about something like box, like Aaron Levy. I'm like, box is uninteresting, but I know who Aaron is for no good reason because like he is the representative. He's the voice of that company. Right? What, what I thought in his particularly interesting is it's almost always the founder founders, but it's usually like one person, maybe it's two.

it could also be like non founders, but it's like less common. At large companies, it often the Microsoft non founder, right? Like [01:25:00] Satya, I don't know, they're, the copilot thing feels a little bit messy these days, but the sort of move towards open source, like they rebranded Microsoft entirely, and he's not a founder. He is just really good. And, and Microsoft clearly is really good at execution, but that's the same thing. It's like, okay, Microsoft used to be known for a thing. I am a Microsoft loyalist now, and I was like the old school, like hate on Windows kind of guy, you know? And now I, I use Windows almost exclusively for like, even work.

fortunately I just don't need to log into certain things. and I love it. Like, I actually think it's way better than Mac these days and that would not have been me before. And partially, and now they might be switching on this. So we'll see. 'cause Microsoft has this famous history of, that's not great in open source, but at least they did a good job of making us believe again, that it's like, oh, Microsoft is an open source company.

They're actually helping developers and they're doing all these things and, and that's just brand, right? And they did such a great job of that brand execution. Know. Now, I'd argue whether you agree with it or not, Microsoft is now full co-pilot shill, right? Their brand is, we are so invested in this ar ai future, which doesn't matter to people like [01:26:00] I know that is Microsoft.

Whether I want that or not is a different question, right? and I think that goes back to like when I say no and who are the right customers, 'cause I gotta resonate with your brand. 'cause like a lot of, especially enterprise customers, like they're buying not your software, they're sort of buying a relationship. It's like they're buying like a partnership. And I was convinced of that. I think that's true. I was convinced of that pretty early on at Sentry though, because like randomly we had, I think it was like JP Morgan reach out long time ago. They did not become a customer at the time. I don't even know if they are today. But, and they just like wanted to like chat with me at reinvent to like understand how they essentially it was like tiny at the time. and I'm like, oh, I just have to convince them that I'm like really good. Like, it's not, I don't sell 'em on features. I just gotta convince 'em. I know everything about this space and I'm the expert and our company is the expert and we are the best partnership they could ever have. and I think they just didn't use us. 'cause like compliance was hard at the time.

but that's brand, right? Like, now it sucks that I had to convince 'em and they didn't already know that. But I think once you figure it out, it's like, oh, okay. You know,

Brett: when you were doing what you would call [01:27:00] sales or founder-led sales, as you were just commercializing the company, what, what were you doing?

David: I was literally being what I wish every PM was, I was, I mean, obviously I was writing the code, but then I was like following up with every customer that had like, you know, if, if there's an open ticket or customer support is phenomenal for this. but it's like if there was a bug that came in through, essentially like we'd see these errors, right?

We would see the email address associated with the bug. I would go fix the bug, then I would email the person with the email address. It was phenomenal. If it was like a signup form or a checkout experience. only goal is like to win that customer in all these scenarios. Right? Again, I had no idea. It just seemed like that's the good user experience.

That's what you'd, you'd be amazed if that happened to you kind of thing. and it was just like any version of that on repeat, I'm like, anybody that wants to use the product, I'm gonna make them the most successful they can be. I'm not gonna do unnatural things, and that's the balance. But I, I am gonna make them successful using the product and I'm just gonna, it doesn't matter the size of the company.

Like I don't care. Obviously it's more exciting if it's a cool logo, but I'm like, I don't care. I don't even know who half the logos are. It's even worse now. Like there's enterprise companies that worth lots of money I've never heard of, and I'll just be like, [01:28:00] well, that's a random startup that said nobody.

I don't care. Fortunately, I just treat them all the same. but that's all it was. It was, it was to me that founder-led sales is not just like, am I talking to the customer over and over? It's like doing all the things to, to make that customer successful. And I, I still do that today. Like we one of the big AI companies was onboarding a Sentry, and don't remember what it was like sales is like, hey. Can, can we get your help? Like, I don't know what it was. Some something, and I look at the account, I'm like, this account is so messed up, they're just using the product entirely wrong in a way that's gonna harm them. And I'm like, did you tell them this? And they're they were like wishy-washy, like sales team was.

I'm like, you know what? I know one of the people here, we're just gonna go over there and we're gonna fix their stuff, you know? And this is literally like last six months. And so I grab one of our directors, who knows, like sort of the domain they were working in. I bring one of the sales engineers along so he can understand what's going on.

We just go to, we literally show up at their office the next day. They knew we were coming. and we just help them get past everything. And you know, there's this argument about like, return to office and remote, doesn't matter which side [01:29:00] you're on, you can't disagree that it's really easy to communicate in person, you know.

And so going into the office and just being able to like, we can just work through any problem that exists in front of us right now in person, talk about it, get past all the cr, and we did. And it, it was great. And like, you know, we still got a lot of work to do with this customer, but, but that is like founder led sales.

That is just, and that's what I'd love all sales to be. But it's like skillset. I have tons of domain experience, tons of context on Sentry, so it's hard to replicate is what

I would say. but I think those behaviors are extremely important. So, and early days you can do this, no problem.

Brett: One of the last things I wanna talk about, when you think about the last 10 plus years of, of building the company full-time, what is the role of competition in anything that you've done? Has it mattered? Has it not, how does it informed what you do?

David: I would tell you I'm at Sentry and I've been capable of building Sentry because I'm very competitive in a sense of like, I want nobody else to exist. And so for a long period of time, we had a bunch of competitors that looked exactly like us. None of 'em exist anymore. And that is not a, that is not a coincidence.

That was not us just [01:30:00] focusing and ignoring what the competitors do. That was me every day being like, we have to be better in every single way than they are in every single territory they're in. And so, for example, one of our big ecosystems is the PHP layer of L ecosystem. Phenomenal thing these days.

It's really good. Lots of people, We are only there in a tangible way. Or rather, the reason we decided to be there, was because one of our competitors was more dominant there than we were. And I'm like, we can't have that. Not only can we not have that, we have the better product, we have better engineer stuff, we can just solve this problem.

And overnight we went from like, we don't really exist there to like unmatchable solution in the space. And we're at the conference, we're hosting like, like we hosted their first official party at the conference. So everybody immediately knew who we were. And it was like, I am, I am like ultra aggressive when it comes to competition.

This is a lot harder to do at scale, to be fair. It's, you know, the numbers are also a lot harder to do at scale. So you actually rely on a lot more traditional marketing, and larger programs. But that's still the truth. Like, I'm gonna Miami next week for React Miami. I have nothing to do with any of this, but like, it is really important to me that I maintain [01:31:00] relationships with this community 'cause it helps me inform decisions, it helps us with market share and marketing and all this stuff.

especially 'cause there's a lot of like content creators now, like call 'em YouTubers or whatever that are actually like super high value in tech. I'm like gonna spend my week in Miami and this may sound fun, I hate Miami. last time I was there I'm like, okay, it's not terrible. But generally speaking, I hate Miami and I'm only going to like, almost main like, kind of do sales, but in a wacky way.

'cause I'm not actually selling anything. I'm not selling to customers, I'm just maintaining an extending reputation. Right. And that is some weird version of marketing. I don't know how you would describe it 'cause it doesn't fit in your clean buckets. Right. but there's just a lot of stuff like that, I don't know.

And you kind of just gotta figure it out

Brett: whenever a new company was scaling or there was an incumbent that launched a Sentry like product, you obsessively tried

David: a hundred percent

Brett: how do we choke the oxygen here?

David: every day. it's, kind of painful these days 'cause our competitors realistically, they're the Datadog of the world, but they don't even do the same thing as us. And that, that's like an annoying version of this that. I don't quite have mastery over.

our strategy for what it's worth is just like deposition. The competitors [01:32:00] like do stuff they can't do, not try to feature, match them or build the same products because their strength is sales, it is distribution. even though we have a lot, they have a lot. It is lots of checkbox features that we just don't wanna build or can't.

Right. And so you're like, well, how do you compete with that? You don't compete by doing the same thing. and so that part's hard, but generally speaking, if a startup enters our space right now, today in the executive team, we are like focused on that startup. Like it, you, you can't allow somebody to sort of, you know, wedge into your, your market, especially for us.

'cause one mistake, I think it's a mistake, but one thing I see people do is they grow over time. They grow their business, become enterprise companies, and then they forget about what got them there. They forget about the long tail customer, the s and b or the mid-market or something. And so many people do this 'cause enterprise dollars add up, like right.

That's where you, you gotta bias it at one point. We don't bias us there whatsoever. You know? And, and I'm still very much like you can't allow anybody to take away that, that marketing funnel, right? That's what it is at the end of the day. and so we're still very, very focused on it, but, you know, as, as is truth [01:33:00] in the world, it is much harder to compete from, velocity, against these small companies because we have so many, like, so many customers, so many technologies, so many things to support.

You know, we can't be loose about compliance or loose about customer data or loose about ai like training, like all these things, right? Much harder to do at scale. And so, so that, I would say that is the constant tension and the constant challenge of the business right

Brett: And, and why do you, other than being obsessed about going after any new company in the space, why do you think you have been successful at, keeping newcomers from, from encroaching on your territory? Is there physics or properties of the actual business that you've built makes it very robust against competition?

David: No, not at all. In fact, every competitor uses our tech these days. 'cause the, all of people like to give us crap because Sentry itself is not open source quotes. all the tech that makes Sentry valuable is permissive open source. And for example, we have this one technology used by every single [01:34:00] competitor in the world, you know, from the biggest to the smallest.

We give that away for free. Everybody should be very thankful. Doesn't mean we get paid on it, and so, no, it's like you can replicate it. There's no, there's no sticking power whatsoever. There's no, there's no sort of weird, just incumbent. We have a mode. It's easy to get outta. It's just like we only win if we are good.

Like if we are actually the great solution for you. And it's really, really good.

Brett: But what about like, in, in looking at the business from a, from a distance, I would've thought that the fact that you are relatively inexpensive is actually a unique part of what makes the business defensible. Because you are, you are so inexpensive that that means you, you need distribution, you need various efficient distribution, you need very broad brand recognition.

And if you don't have that, you quickly end up with someone competing with you on price with a traditional go to market, and the business gets turned upside down. Like do you think about stuff like that

David: that that is,

that is an intentional thing. Like the, we have to be, maybe we're not the cheapest all the time, but it's like you can't really be cheaper than us. The reality is though, you can go raise money and charge half. Like we [01:35:00] have some startups that like try to give you more data. Little do they know you don't need to give more data because like people don't have that much volume.

So we, the good thing is we have a margin model and cogs it. There's like, we can sustain this to infinity, startups can't, but you will take shortcuts in the name of growth and that's fine. That's what you do. Well, I would say yes, that allows us to be defensible over the, the very long timeline. It doesn't really hold us from the near term timeline.

So also it's like $30, $40. It's the same thing if you've raised venture. Neither of those add up on your bill. and so I don't think there's anything really there that kind of cements our position. Obviously distribution is really important. Distribution is the one thing that you can't compete with.

And what I'm, I'm very interested to see what happens in the space with like vs code cursor windsurf, because Microsoft has the distribution and if they keep up on product, which they kind of are, and cursor's been growing great, for example, right? Does, does Cursor have sticking power? Does everybody just go back to Microsoft over time?

I don't know. Like it's a, it's a really big test of like, cursor has no distribution, they have no sticking power. Can they succeed in that? Maybe. It's hard to [01:36:00] say, but it's uncommon at the very least, right? And so that is the strength we have now, but it took a long time to get there. I think things like the ability to self-host and there, there's a lot of these little things that I think do add up a little bit.

But not in like a very serious way. And so I don't think there's an, anything inherently like a network effect or something equivalent to that that like, makes our business more safe from that. we just spent a lot of time trying to make sure those people are successful and we don't always do it to be fair, but it's, it's the same thing.

It's like, okay, you customer, why won't you use Sentry? Maybe we should solve that. Okay, you customer, why would you possibly choose that competitor? We should definitely solve that. We should remove any reason that, that you should use any competitor. And then we've also gotten clever enough to where the, we're a big enough size.

We can actually just go take customers from other competitors. Which, if you're a startup, we don't really do that. But if you get, I dunno, say you're 10 million in revenue, we will come after every logo you have. we haven't done it that much, but we have gone after two companies and they basically don't exist anymore, like two competitors.

And so just how business works, like everybody should [01:37:00] know this is the reality. all the big players try to do this to us. We're just pretty, we defend well enough, not fully, but it is, it is. It's very different, like early stage, you don't worry about these things. It's not a as much of a problem when you think about things, especially when you're in a, like an uninteresting space.

But we, showed that you could make enough money in this space that it's no longer uninteresting. So

Brett: just to wrap up, wanted to end where we always do, which is who's somebody that's had, had a disproportionate impact on this journey into sort of building something with immensely strong product market fit. what's like the thing that they bestowed upon you or an idea or something that's like, has either had an outsized impact or like has a lot of resonance or residue in your brain?

David: I don't actually know on the product that I think it's literally, I just, I'm out to prove something. But I will tell you one thing that has had a genuinely immense impact on my, my view of the world. So, beats like the headphone coming, the Apple now owns, there an event where the, I think former CMO Omar Johnson was speaking, about marketing.

Brand and all this stuff and how Beats competed. I think they had already sold Apple at [01:38:00] this point. and his background, he is, he actually worked at Nike previously. And if everybody knows about Nike, obviously it's a great brand, right? And I, I just love brand. Brand to me is a phenomenal thing. and he's speaking about this, like how they won, and this is probably the most impactful conversation I've ever, not even conversation, just hearing somebody speak that has led to a lot of decisions where he's like, we won against Bose by doing everything Bose would not do.

We didn't look at say like, how would we compete against Bose? We're like, well, if Porsche was us, you know, because that's a company we admire, what would Porsche do in the headphone space? Or something stupid like that. And that, that was just like cemented so much in my mind. I'm like, okay, like, and this is why we do wacky things in marketing at Sentry and, and frankly in anything, because I'm.

I don't care what the random boring enterprise logo company would do. Like, they're irrelevant. Like you gotta like the goal's, attention, stand out, and agree. And going back to like though, and strength we have is distribution and thus market share is like really important. It's like, get market share.

You gotta stand out, you need to do this thing that is like gonna be really representative of what you believe in. And, and so we do it. And so like we have [01:39:00] this open source pledge thing, you can kind of figure out that we ran it, but like we put up billboards with these funny looking faces on them that like made fun of CEOs and stuff.

It's like activism makes no sense for a business. Right? And the only go, and I don't know if it's successful or not, but it was like, that seems like a good idea. Let's try that. Like that's brand building that's like, gets attention and stuff. And it all goes back to like this one conversation where like, we were like a series a company of 25 people.

And I'm like, I would love to employ somebody that thought that way. We never have mind you. but it is the most impactful thing because it, I will also say, most founders look at me because they, they actually are like, we, like hugely admire what Sentry's done in the brand building space. And that was not always true like five years ago.

I don't think that was true. Like you didn't know us really. but I think a lot of those same principles apply where I'm like, I want people to admire what we do. And it turns out brand marketing is a really good way to like say what you care about and ideally then like get that like sort of feedback loop of people appreciating it, you know?

And so that, that, that was huge for me.

Brett: Great place to end. Thanks for such a fun conversation.