David Cramer, co-founder of Sentry talks M&As and why they should be utilized more when you don’t achieve huge success. Plus we talk about the importance of good branding.
We discuss:
The biggest mistake small startup founders make by not exploring potential acquisitions.
The role of ego in startups
Product-market-fit
Hiring entrepreneurial talent and why acqui-hiring is so big.
The significance of branding beyond just marketing – how it builds trust, recognition, and demand.
Sentry’s approach to branding, emphasizing authenticity, community, and accessibility.
What DevTools can learn from Liquid Death and Porsche
Why brand matters
This episode is brought to you by WorkOS. If you're thinking about selling to enterprise customers, WorkOS can help you add enterprise features like Single Sign-On and audit logs. https://workos.com/
Learning from Experience and the Value of Reflection
Evolving Leadership Roles
The Importance of Brand
Building Demand Through Brand
Navigating Complexity in Product Development
Advice for Aspiring Founders
David Cramer, co-founder of Sentry talks M&As and why they should be utilized more when you don’t achieve huge success. Plus we talk about the importance of good branding.
We discuss:
The biggest mistake small startup founders make by not exploring potential acquisitions.
The role of ego in startups
Product-market-fit
Hiring entrepreneurial talent and why acqui-hiring is so big.
The significance of branding beyond just marketing – how it builds trust, recognition, and demand.
Sentry’s approach to branding, emphasizing authenticity, community, and accessibility.
What DevTools can learn from Liquid Death and Porsche
Why brand matters
This episode is brought to you by WorkOS. If you're thinking about selling to enterprise customers, WorkOS can help you add enterprise features like Single Sign-On and audit logs. https://workos.com/
We investigate what it takes to grow a developer tool. Topics include developer marketing, DevRel, developer advocacy and developer experience.
Jack:
David Cramer is the founder of Sentry. I use Sentry to get alerted when things go wrong and then to figure out what actually is going wrong. And I'm not alone. David shares that Sentry is doing 9 figures of revenue, so at least a hundred million. If you haven't followed David online already, then you're in for a good surprise because David is extremely straight talking.
David:
The only way you can hire the best people is by paying ludicrous amounts of money to acquire failed businesses.
Jack:
We start off by talking about m and a.
David:
Almost all of the time, you'll at least get some ROI for your time spent.
Jack:
We also talk a lot about ego.
David:
You gotta have this naive like, almost blind ambition. Like, believe that this stupid thing can be bigger than it possibly should be capable of being.
Jack:
And much more.
David:
The reason I've been able to do what I do is because I'm willing to make just rash decisions. It's how we develop the best product. It's how we develop trust of customers. You can't have a shared vision, generally speaking. Like, the way I paint this is gonna be wildly different than you paint this.
David:
Don't build a damn status quo thing. Don't build logs or something be like that. Like, you will fail overnight. So don't just build something that exists for no good reason. Just don't don't do that.
David:
And then just try a lot harder than you are trying. Success is just grind. There's nothing more to it.
Jack:
David, you you put out this tweet the other day that if someone's, like, to a free company to a free person start up and it's not going that well, they should think about m and a and it's one of the biggest mistakes they'll make if they don't.
David:
Yeah. So I've been angel investing for a number of years now and a lot of, like, what I post whether it's like long form writing or just blurts on Twitter, it's just something that is, like, probably loosely happening. Sometimes I try to be clever about hiding it because people get mad at me quite often, in fact. But this was kinda triggered as, like, I've I've now seen several companies that I've invested in sort of come to completion, not succeed, like, just basically dissolution or something similar. And I'm like, why didn't and not a single one, like, reached out to me.
David:
And I'm like and and there's it's one of those things where I think people just are unwilling. Either they don't know because people are not counseling them or they're unwilling to do it. And and the mistake people make is, like, as a founder is, like, you kinda have to always, like, eat. You always have to do the thing that's unfun or uncomfortable because your goal needs to fundamentally be to, like, do something successful. And people make I I think people naively make the mistake that they're gonna start a they're gonna found a company, and it's gonna turn into a real business.
David:
And it, like, almost never happens. Right? Even Century, like, which were a one two three four five six seven eight, a nine figure revenue business. It's like, yeah, it's sort of successful, but, like, you know, there's sort of these barriers that are hard to reach. And so, you know, we've we've passed a lot of them, but every every sort of step, it gets harder and harder.
David:
And and one of the things you just have to do is always, deal with these uncomfortable situations as sort of this primary founder CEO type personality. And I often wonder if people don't go down this approach because, you know, they don't want to. Like, as in, like, they think it's not gonna work. They're pessimistic about it, or they've been guys not or guided not to. And I definitely know there's a lot of people who are like, oh, no.
David:
No. M and A is bad and blah blah blah. And these are all people who've failed in their careers. And so I would ignore all of their advice. But the problem is almost certainly your business is gonna fail.
David:
So then why would you not explore m and a with every like, why would you not explore every possible outcome you have fundamentally? Right? And that to me is the mistake. And and I think in in this case, like, I pretty much invest almost almost exclusively in companies that it's literally a a a twofold agenda. I invest as somebody who's, like, interested as an angel.
David:
They'll mostly from a, like, a relative I wanna see what's happening in the world, but also from as an executive of a tech company who can acquire most of these. So a lot of the companies I invest in are, like, dev tool startups. And it's it's just one of those things that I'm like, why would you not do this? And I don't know why they they're not, like, investors telling them to do this or like like, real investors, like venture capitalists, you know, or they've not been taught this in YC or something else. It just doesn't make any sense to me because almost all of the time, you'll at least get some ROI for your time spent.
David:
Now maybe you have a two year period where you gotta hang out at this company, which is not good for everybody, or rather, it can be good for everybody. Some people choose to not take advantage of it is what I would say. Like, a lot of people in in acquisitions, especially acqui hires, do not really wanna be part of, like, this other company and contribute and blah blah blah, which is like it's like a known quantity thing. But I I will tell you throughout my career, like, when I was at Dropbox, everybody was like an MIT new grad, good and bad, like, really smart people, not super capable of a lot of things, not really aware of a lot that exists in the world. You know?
David:
But they had a few senior folks. And the way they started growing, at least from my perspective at the time, sort of these senior, really high domain value folks was just through lots of acquisitions. And half the time that acquisition was for like, primarily, there were two people that were really inch like, those were the people they wanted out of that company, and it was usually, like, two founders or something like that. Right? And so I I just think it's silly that people don't explore this, and I've I've yet to uncover the root cause of why.
David:
But I do think it's, like, a really important outcome. And I I do think, like, if you're gonna start a company, you know, yes, build some try to build something very successful and whatnot. Step one is try, which most people don't do. And then if it doesn't work, which it statistically speaking, it likely won't, try to find a good outcome that is not just you being egotistic about, like, how great you are. Because clearly, were not that great if you couldn't succeed at this business.
David:
Like, clearly, you did not have those right skills or some right capabilities, and that's just the truth. Right? Like, and even Century, like, I would argue, like, maybe we got a little lucky. I worked my ass off, but we had product market fit right away, which is really hard thing to achieve. And we had a large TAM that has been able to grow with us for the most part in what was considered a noncategory.
David:
Like, error monitoring was not a thing. And arguably, shouldn't be a thing. It's it's just should be one feature, but we turned it into a 9 figure business. But that that's like a rare thing. Right?
David:
And so I don't know. It's just it's this wacky thing, and I just think there's a lot of people glossing over the details in sort of start up plan in the sense of, like, they just, you know, naively tell each other that they're great and everything's gonna be hunky dory and stuff instead of having, like, honest conversations about, like, this is how the world works. This is how you should think about it. Even even when you raise money like, I remember I had first partner pitch I did, and I didn't know what I was doing. We just made some we had revenue, and I thought it was gonna be easy.
David:
I go in, and they're in this partner pitch. We made, like, 600 k in annual revenue at the time. They're like, if somebody offered you 200,000,000 for the company tomorrow, would you sell it? I'm like, absolutely, I would sell it. That'd be, like, the most ludicrous return in history.
David:
And they declined investing because of that statement. And I'm like, I don't I don't even know if this firm exists anymore, and, you know, good riddance because they don't know what they're doing. But I'm like, and and it's like a trivia game. They know the right answer is, like, take the offer. Like, take the 200,000,000 offer.
David:
It's, like, stupid not to. But still they play a stupid game where they pretend all these other things matter instead of, like, the actual, like, like, ROI. Right? The return on And I don't know. I I find the game silly, and maybe that's partially because I didn't grow up in this world.
David:
Like, I'm a self taught software engineer. But I just think there's too much of this propagation of nonsense between people. And so my view of the world is just ideally in a way that's, like, not harmful, speak what I believe to be a more authentic truth. You know?
Jack:
This episode is brought to you by WorkOS. If you're building a dev tool, at some point, your customers are gonna start asking you for enterprise features. Work OS offers you single sign on, skin provisioning, and audit logs out the box. Work OS is trusted by Perplexity and Vercel, as well as Work Brew, a homebrew management startup that I recently interviewed. I just told Mike that WorkOS is the sponsor, and this is what Mike said.
Mike:
Yeah. So WorkOS isn't paying me any money for this. I I pay WorkOS money for this, but WorkOS is, like, one of the best developer tools I've, like, ever used. It's it's the documentation and the experience with building with them is so, so good. Like, I initially was almost like, okay, this seems expensive, but then I built an integration with them in about twenty minutes that I had spent two days banging my head off the wall trying to build it directly with Okta.
Mike:
And then with WorkOS, I then have like many, many SSO providers like supported instead of just one. So yeah, like for me, Workhorse is one of the nicest developer experiences I've encountered in the last, like, five years probably. And and it's so surprising because a bunch of the developer team are ex GitHub and therefore are very good at their job.
Jack:
Go to WorkOS.com to learn more. Yeah. Is it like kind of, I guess, like doing what is right for you rather than like there's this maybe there's this like, the reason people do it is like this kind of propaganda. Probably like VCs would prefer you to stay in the game on this, like, very, very minuscule chance that things will, like, turn around completely.
David:
It's hard for I I I don't know. I because I've never lived in one of those situations, and there are a lot of really bad VCs to be fair. Like, the standard VC is some finance person who has no idea, like, how any of this works, and it's like an Excel sheet for them. Right? And and so I don't know if it's coming from bad advice from them, like, as in they literally say don't do this kind of thing, or if it's coming from lack of awareness of these things being totally which is kinda the same.
David:
If you don't give advice, that might as well be giving bad advice. Right? Because, like like, I will say our our first partner is super helpful for me because I didn't know how the the venture game worked and all this stuff. And and over the many years now, he just he's he's been able to provide me a lot of advice both personally and professionally. And it's like one of those things where you just don't know what you don't know.
David:
Like, how are you gonna ask a question if you don't even know that that line of questioning should exist? And so I don't know. It it's one of those things where I'm sure if you if you went and interviewed a bunch of people, you could probably root cause a little bit of it, but it's just silly. Like, people should explore every avenue. And, yeah, try to be successful, but, you know, there are other versions of success anyways.
David:
And particularly, venture capitalists are fine. It's not even their money most of the time. And so you should consider your personal ROI too. Like, how much time you spent on something? How do you make up for what almost always is lost personal revenue?
David:
Right? Like, usually, like, when I when I left Dropbox to start Century full time, I took, like, a, like, a 25% pay cut or something at the time, which was a lot of money because, you know, we all got paid less in Silicon Valley way back then. And, I mean, that's a big deal. Like, you rack up debt or whatever. You know, like, you're living much more frugally.
David:
It's not fun. And so if you can make up for that lost time or you can advance your career and you can maybe work with other people who you can learn from things like that, which, again, there's, like, an ego involved in a lot of this, I think you need to consider all of those things. So both and to be fair, I think a lot of founders are considered of their team, but I think they're too considerate of investors and often they're not being fed useful advice.
Jack:
Actually, you kind of spoken a bit about ego a couple times, and I think in your tweet as well, like, how how do you think, like, founders should like like, what what should the role, like, of ego be in the sense of?
David:
I think you gotta be borderline sociopath to be successful. Like Okay. You I I tell people the reason I've been able to do what I do is because I'm willing to make just rash decisions. Now I make them with the information on hand, but I don't I don't go seek out a bunch more information before I make a decision. And part of that is, like, this, like, just huge amount of confidence I have.
David:
You can call it ego, call it confidence. It doesn't really matter to me. It exhibits the same way. Right? And you gotta, like, not care about being wrong.
David:
Right? And that almost certainly is ego, but it's like a rational version of it where that's actually how you have to operate. And if you look at any leader, like, you can even look at you know, we can talk about the all the presidents all day long. The good presidents also do this, and this is why we we do talk is because they're like, they did this thing, and it was, like, clearly bad. But they did it based on the information they had, and they you have to do a thing always.
David:
Right? And so I think the the the two sort of core things are you always need to be ambitious, like, forever ambitious. You you can never sort of settle in the sense of, like, oh, it's not really growing, but maybe if we just keep plugging away at it or something, it will work. It'll figure itself out. Don't know if it if it doesn't work, you try something else.
David:
You try harder. You figure it out. Let's say hiring and firing is a really big challenge for a lot of people, myself included, in that same line of thinking. But it's like, you gotta have this night like, almost blind ambition. Like, believe that this stupid thing can be bigger than it possibly should be capable of being.
David:
You know? And then you've just gotta be really indecisive and not be too sort of like, you can't take these failures personally. Like, a criticism that people would give me early in my career is I would make these decisions, and if they failed, I would not admit fault. And I'm like, yeah. Because that's the the name of the game is not to take personal accountability for everything we do.
David:
We're gonna mess some things up. We're gonna succeed at other things. It's always you gotta move forward. Like, if if if whatever you're doing is keeping you on a flat line, then, like, you're failing. Right?
David:
Like, one of my favorite quotes that, like, really represents what I think founders need to understand or leaders, actually. Leaders is probably a better example than founders. I think it's the same thing, but is I'll butcher this, but I think it's Einstein, which is, like, the definition of insanity. It's like continuing the course of action, like, basically, changing, expecting different results. And so I I use that, and I think about that quite often.
David:
Because, like, if something's not working, you have to change something. Now what you change often varies. Right? But, like, clearly, something's wrong, so try to root cause what most likely could be wrong. You may not get it correct.
David:
You may not be perfect. It may be, like, you accidentally picked the fifth most important thing that was wrong or something like that. But the problem is when you just don't do that, it's worse. You know? Yeah.
David:
So it's a lot I know. But
Jack:
No. No. No. But I think you also talked about like how you would this kind of on the confidence, you you would you mentioned that you believe you could solve every problem that was in front of you, this kind of confidence.
David:
It's an interesting thing because it's a double edged sword. Right? And you see this, like, the massive egos from the most successful people in the world. It's very hard for them to be humble, which is fair. Like, they're unbelievably successful.
David:
And when you hear about their stories like, I've been listening to the Acquired podcast more recently. My god. The episodes are long. But when you hear more about the details of some of these founders, like, the greatest founders of that we've ever known, you know, of, like, sort of the stories, the early days, you grow deep admiration for them. And and, like and I feel like I've been through the trenches.
David:
I'm like, you guys are so much better than me. Like, in every single way, like, you're just insanely good, which makes sense, like, because it's it's so rare to build even a company a century scale, let alone some of the greatest companies, you know, we've ever seen. And so I don't know. It's a really interesting name. But I I do think that my my biggest gripe in the industry, and this is just somebody that's like a an executive at a company, less so a founder, is, like, it's always hard to hire great people, and it's annoying the venture game because the only way you can hire the best people is by paying ludicrous amounts of money to acquire failed businesses.
David:
And it's even more annoying you can't hire those people because they don't even consider m and a because of who knows? Right? And and so that's, like, the personal annoyance I have with the whole thing because that entrepreneur, like, sort of the grit and the the person who's just willing to deal with chaos is, like, such a valuable skill set. Doesn't mean they can be, like, you know, a VP at a company or anything, but, like, you just need those kinds of people to run projects, to run teams, to run basically everything. It's, like, the most successful way you can do anything because they're not gonna they they hate process.
David:
They just wanna get stuff done. They wanna, like, build something that's good. They care about those things, and I feel like it's a hard thing to teach. And the only way I found to bring in those people that's not basically hiring founders is, like, new grads and which is a great way to hire for what it's worth. Obviously, like, there's a challenge you can't have all new grads, but but it is, one of those those awkward things in the industry where a lot of these and everybody knows this in the venture crowd is, like, everybody starts companies.
David:
They know most of these companies. The best case outcome is m and a. And so the reason people often invest in founders over ideas is because, well, that founder's really good. Maybe maybe they'll get they'll strike it lucky here kind of thing. But most companies will be happy to, like, acquire, like, a good team, you know, especially if the team's not huge.
David:
And that that's what the other thing is, like, these conversations and a lot of what I'm saying from that angle is more about, like, if you're earlier stage, if you're, like, sub 10 people. You get ten, twenty, 30 people, and then you don't have a real business, you you definitely up first off. Like, you should never have grown the business that large or the the business. But that's a much different math formula that goes into that kind of acquisition at that point. And usually, I think for any sane company, it will involve not acquiring the whole team just because, like, the whole team is usually not worth that much and you've got a lot of redundancy in there for a, like, an already established business.
Jack:
Yeah. That that's really interesting. I think you answered like one question that maybe I asked you in the first recording before we redid it. But it's that like what the value you have as like the acquirer for these kind of small companies is that this is potentially the or this is the best way to get the best people.
David:
And Yeah. It it is. It's like and and that's why I'm like, more people need to consider it because I need to find those people. And again, it's not everybody. You know, there's so many people that start companies, and and not every company is gonna be aligned.
David:
And you still gotta have, like, cultural sort of alignment. Right? And that's that's a big deal, especially in these days. Like, even though, like, remote versus not remote is a much bigger topic point. And, like, another annoying thing about all these startups is everybody was remote because half of them started in COVID, which is a problem for a lot of companies like ours.
David:
But and so not everything's a fit, but I think it you at least have to go down that path. Because the other thing people don't understand is you don't know anything about a company without being part of the company or really getting into some serious conversations with them. And so this idea of, like, oh, we don't think that company makes sense for us or we don't think they're doing stuff in his face that's related to ours. It's like, you just you have no clue. Like like, most technology applies everywhere, first off.
David:
And often, the scale of what you're doing is insignificant anyways. Right? So a lot of acquisitions that I've seen in my career will come up and be they'll be, like, teams that augment other teams, and it might be internal teams or something like that. That's totally fine. Those problems can be interesting.
David:
You know? But I think it's just like, if you don't explore it, you will never know. Mhmm. You will never know what what opportunities existed. And maybe the right way to explore it is to not talk to venture folks and talk to your angels, the actual operators, the the founders that you've decided you want on your cap table.
David:
But I don't know. That that's the main thing is I I think people don't ask for things enough in the industry. And I think they rely on too much of this what a banker is telling them is true sort of dilemma, which is not the right way to do anything. So
Jack:
Yeah. One one of my friends is not DevTools but he just went through like a kind of on like not like a big exit like this sort of thing and it worked out really well for him and you know, made some made like a good salary that year basically. And then
David:
Yeah.
Jack:
It like looks great and everyone's impressed. Like it's a great like LinkedIn announcement. Like he got a really good job from it.
David:
Yeah.
Jack:
Not there but like somewhere else. And then it's like, he's really happy and, you know
Mike:
Yeah. And that's the thing. And I
David:
think it's also like, there there's no there's no free lunch anywhere. Right? Like, we acquire company. Our hope, our ROI calculation is that that will accelerate something. Right?
David:
Because why would we pay a bunch of money just to make less money than we paid, right, in the grand scheme of things? And I think people also gotta recognize that. It's like, we're investing in a thing because we think that thing is a good investment, and often that's the people. And if those people are a good investment, the business should also grow, right, ideally at a faster clip, and you're getting equity in that new business. Thus, it's really good for you because, like and it's also, like, important because a lot of there's sort of this insider network of of venture and stuff and even even companies.
David:
And so sometimes this opens up opportunities that otherwise would be hard for you to access, which is another really important thing because it's a I actually think it's a lot easier to start a business than it is to get a a job at some of these, you know, high tier companies. And so there's something to consider in that regard too. Like, would it help you accelerate your career? Would it push you into new sort of positions that could be really interesting where you could learn? And maybe you take that, you know, two, four years down the road and try a a new thing with everything you've now learned.
David:
You know? Because I actually think yeah. I've mostly worked at startups all my career, and and Dropbox at the time was the largest company I worked at. I guess, technically, still is because Century's not as large before I left Dropbox from a headcount point of view. But I learned a lot actually.
David:
Like, I was there sub two years, and I learned a lot about, like, just a different kind of organization and different way things were run. How an organization was run when they were super wealthy or when they were all, just sort of Ivy League elite, and they came out of this. You know, there's all these little things you take away that you apply, and those are very, very useful lessons. You get them at small companies and large companies, mind you. And they're there if you look for them.
David:
They're not there if you're like, oh, I hope I just get a bunch of money out of this acquisition, and then I'm just gonna, like, cruise control. Like, good luck. You you'll fail at everything you do in life if that's your approach. Like, it doesn't matter. You know?
David:
It's also a small world. So if that's your personality, you know, any sane person will, like, look for references on you, and they're not hard to find. So
Jack:
Wait. And just to dig in, that's be you're saying, like, don't don't be like a kind of extractor. Like
David:
Yeah. Yeah. Yeah. One of those people. Like Yeah.
David:
I don't know. What whatever your belief system is, karma or something else, like, it it'll inevitably not work out in your favor, you know?
Jack:
Yeah. So Like, yeah. You're selling something that isn't really there like post acquisition, they're like, wait. What? Like, you've faked all the not not even like faking, but, yeah, you're talking about that sort of
David:
Yeah.
Jack:
Hyping it up.
David:
This is the problem. Like, ego is ego is always the thing here because it is that double edged sword. I think some people just have like everybody kinda needs to be humbled all the time, like, single person. And I think it's a tough thing. That's why you see, like, there's all this, like, rhetoric from, like, wealthy people that were like, especially, like, Elon Musk is a great example.
David:
He just says whatever he wants. He doesn't really care because nobody's humbling him. Nobody's, like, sort of forcing him to step back and be like, what the dude? You know? And I think it's especially tricky for early stage founders because you you have to develop this massive inherent belief that you can succeed and you can do this and you're good and all these things.
David:
Right? And then you don't. And and you go through, an acquisition. It's like, hey. Actually, like, maybe you're not as good as you think or maybe you're not maybe good is the wrong word, but maybe you're not capable of the thing you thought you were or not yet or you didn't you know, something.
David:
The something clearly wasn't there, and you can't just say, well, you know, the the product we built, you know, the market wasn't ready for it yet Yeah. Or, you know, something like that. Because, like, you can make any idea generate revenue and be at least a degree of success. Right? And so it comes down to more experience ex execution, all these other little things.
David:
This is my my genuine belief. Because product market fit is not like a it's not like a thing you just generally, you don't stumble upon it. I think that a lot of companies have, but it's like a thing you create. And you create it through understanding, like, how you would get there and what the the faults are and how you'd execute it. You know, all these little things.
David:
And I I definitely have seen a lot of people in my career that think they are more capable than they possibly are, and it creates a lot of problems because they then they don't wanna be less. Like like, imagine you go and I I know somebody like this. You go and, you were like you worked at a company for ten years or something. You got promoted over and over, and then you go work somewhere else. And it turned and but, like, you can't actually get an equivalent job somewhere else because it turns out that company was and it basically just inflated your ego, and you actually were incapable of doing the things at the a normal place like that.
David:
I I know actually a handful of people like this. That's a bad situation to be in, mind you. But that that's, like, a very humbling experience. You know? It's like, you kinda gotta be like, I guess I'm gonna take a, ideally, a better company, a lesser role, and then I'm gonna continue from there, which shouldn't be a problem, but it is a problem for people.
David:
You know? It's just how humans are. So, anyways, I know I'm I'm I'm gone down a a long rabbit hole here.
Jack:
So Yeah. Going massively off paced. But like, I was listening to someone talk about Churchill the other day and like how he like was in charge of this battle in like World War one and he like was responsible for like hundred thousand people just dying. And he took it like really really badly. And he basically resigned like he resigned and like went into the trenches in World War one and like just like redeemed himself which like not many people do.
David:
Yeah.
Jack:
And I feel like it like what you're saying is like it's can be okay to like just take the like, you know, have your ego to take a bit of a battering. It doesn't mean that that's gonna be like the rest of your life.
David:
Yeah. I think it's why it's useful and this is why like, in our other the rest of our executive team knows I my intention is to be somewhat public about what we do. And, like, part of it is because, like, it is humbling just to admit blame. It actually doesn't matter. People people, like, respect it way more than anything else.
David:
So it's like a win win. Like, not only can it bolster your ego, but it also helps you, like, recognize what did and didn't work, which is a useful skill. You know? And I don't know. I it's just, like, more people should do it.
David:
Again, it's this challenge of, like, you're sort of you've been convinced by other people and by yourself that you must be great. You might blah blah blah, all these things. And it doesn't mean you're not great at a bunch of things, but at the same time, you're also not great. Like, there's many things you suck And I I will be the first to tell you all the things I am garbage at, which is why I've changed my role so many times in the company. I'm like, I don't wanna be CEO.
David:
I hate hiring marketing leaders or sales leaders, you know, all these other things. Yeah. And when I I just recently last year hired a CTO and changed my role again, and I'm like, I don't really wanna run a large organization. Why like, I don't have an ego that needs that. I already like, I started a very successful business, and I get to work on interesting things, and I get to work on corporate strategy and all this I don't need 200 people reporting to me to feel like I'm more successful.
David:
You know? Mhmm. And I just you know? Some people, I think, get that in doses. Right?
David:
Like, they might be like, yeah. I agree. I I don't care about the reports, but then they'll have the massive ego about something else that they are not going to be good at too. You know? So
Jack:
Yeah. I think even just the way you describe, like, great and, like, suck and stuff is different to, like, most people. I don't know if it's just like, what you mean is different, I think, to what some other people.
David:
I think I'm just, like, I'm hypercritical. And so not everybody likes this about me for what it's worth, but, like, I am I have a very low tolerance for something that cause even my wife hates this. Like, a a low tolerance for something that causes me grievance, like like, the littlest things. And and, generally, the only way I avoid it is just by, like, out of sight, out of mind kinda thing. But but it is useful, I will tell you, in a lot of things because it means I care about some stuff that is literally a waste of time, which whatever.
David:
You know? I don't try to micro optimize about which things I should care about. But also when you're developing product and any kind of customer centric thing, it is really, really useful to have a low tolerance for, like, friction and things like this. Right? And so, you know, some of the team I'm sure is, like, annoyed by this, but I will go in and I have some side projects once in a while, and I'll I'll be working on my thing, just naturally working on it, and I'll try to use Sentry, I'll get I'll just get annoyed instantly.
David:
Like, I'll be like, this thing sucks. It did not solve my problem in, like, two seconds. You know? And, obviously, it's not that extreme, but I think I'm a big fan of just exaggeration. Whether it's useful or not, I don't know.
David:
But I think this, like, sort of low tolerance is like, I am a I have I have a good product sense, which helps, but I am a very good person to basically do something effectively, like user testing if your goal is to minimize objections. Because I will find everything in, like, in thirty seconds.
Jack:
Yeah.
David:
And it I don't know. It's like, I'm sure other people can too. I don't know if there's a skill here. I I am seemingly good at it, but I don't think it's a hard thing to be good at. But there's, like, this thing of, like, the I'm I'm not a patient person, which is not a good trait for what it's worth.
David:
Or being patient is a good trait. I am not patient. But I do think this thing for just, like, not tolerating things that are frustrating is a really big deal. And I've had that my entire career. It's not like I developed this starting a company.
David:
I you know, it was more problematic when I was, like, 20 years old. It's more useful now that I'm older, probably because I'm a little bit, like, wiser and stuff too. But it has always helped me build better things or be more ambitious with what I'm doing because I'm like, first off, that's not that hard. Most things are not that hard to accomplish, or at least what sort of the result looks like is pretty black and white. And so finding a path there, as long as you're sort of like a, you know, a logic brain kind of person, which a lot of us are in the tech scene, right, is not that hard to extrapolate.
David:
And so then it's just like, okay. Do this stuff. And then when you get to a step, like, you gotta unwind it. It's like, oh, I wanna build this technical thing. You, like you effectively break it down and be like, how would I build this technical thing?
David:
It's it's the same for everything else. And so it's like, if you can reason about these things and just implement them and then just have this kind of I don't know. And, like, I I early in my career, used to associate with, like, work ethic, and maybe it's a bunch of these sayings, but it's it's really this like, I would say, like, good is not good enough. You know, there's the what is the other one? Perfect is the enemy of done or I don't know what it is.
David:
There's bunch of these sayings. But this idea of, like, oh, it could be better. You know? Yeah. Is a really useful idea.
David:
It doesn't mean you should always make everything better. Right? Or you still gotta prioritize in there, but kind of just not resting on your laurels and not tolerating this thing where it's like, well, it kinda works. Because, like, if you look around, like, that's most businesses. They build some, like, and then they wonder why it, like, plateaus really quickly or isn't successful.
David:
You know? It's like, well, you didn't try hard enough. You didn't you didn't say how could this be better over and over and over and over until you ran out of things that it could be better, you know, at. And we did that a lot in early day century where it's just like, oh, this kind of widget, it's annoying. Like, it's not good.
David:
How could it be better? Or, oh, this information is not clear enough. How could it be better? You know, things like that. It was like all these incremental changes, which is much harder to do now at our scale, which is one of those things that bothers me, but it was a really impactful thing early on.
David:
It's how we develop the best product. It's how we develop trust of customers that we were, like, good, that we were gonna be the right partner, which is how, like, you should think about customers. They're looking for a partner, not just to buy a product most days. And so I don't know. I I don't know how I would identify those traits in people without seeing them or working with them kinda thing, but I think it is like a the best people I know exhibit some versions of these things.
Jack:
I've seen it for, like, people of, like, your kinda caliber of, like, really successful DevTools founders do talk about this kind of, like, pain thresholds, like, lowering it and, like, just being really dissatisfied with, like, the status status quo. I was trying to decide whether it's still about hiring or branding. Actually, do you have a preference? Which one do you think is more for
David:
I think branding is more interesting because people have Yeah. No opinion, bad opinion, or just uninformed kind of thing.
Jack:
Okay.
David:
Yeah. Okay. Branding. Everybody has an opinion on hiring. So Okay.
Jack:
So how how do you think about branding at Century, David?
David:
So okay. I it's been interesting because I don't know anything about okay. Actually, I should say I don't know anything about marketing, but I'm not a marketing person by trade. Right? Like, everything I believe in is basically what I've seen or I'm self taught and all this stuff.
David:
And I still would say I'm not a marketing person, but I do think I understand a bunch of this brand stuff. But I've also been learning more about it talking with other kinds of businesses lately. And so one thing I've grown to believe in is that brand is basically just in in an absolute sense extremely important no matter the scale of your business. Because brand can be personal brand. It can be corporate brand.
David:
It actually doesn't matter. Right? But, like, brand is this thing that sells, like, your values, and inherently what you want it to sell is, like like, this thing people want or believe in. Right? And it's really interesting because, like, I remember this this stage of my career, better to articulate why all these things might work that I believed in, but early career, I cannot.
David:
And even early career, like, early century. But I remember this moment we were at the PyCon conference, the Python programming conference in The US. It was in, I think, Portland. And there's this arcade there. It's a barcade.
David:
Fits, like, a hundred people in there. This conference is, like, 1,500 people. And we're like, let's host a century party at this thing. And we're like, oh, it only fits a hundred people. I'm like, it's it's fine.
David:
You know? And my god, is this place honestly, it should fit 50 people. It was super cramped. But what happened is everybody actually wanted to go to this because it's a barcade. It's a programming conference.
David:
This is super fun. It's like a well known place also in Portland. I don't remember what it's called. We let a bunch of people in early who were, like, people that were just interesting folks or sort of members of our community, things like this. And, you know, I was supposed to say start it.
David:
I'm just picking the time. Like, 08:00, we're all in there at seven or something, hanging out, having a good time. There's a line around the block to get in. The place we I don't know if we ever let anybody in because it was at capacity the whole time. And I'm like, that was a success.
David:
To me, that was a success. Right? Because we created demand for something that people wanted, and they couldn't get it, which is still a useful tool. And even at the time, I thought it was a success, but I didn't quite understand how to articulate why. And to me, a lot of brand is that is creating demand.
David:
Like, it's like, oh, like, their brand represents these things. I want those things inherently, or I believe in those things. Thus, I want them. How do I get them kind of thing? And sometimes that brand sometimes the brand is not used in that way.
David:
And so, like, a good example of that might be I'm trying to think who ex like, sports cars are a good example of a brand that's creating a, like, pure demand because of, like, they're they're very big show pieces and stuff. But the other thing I kinda appreciate more recently is brand is also useful in small scale com small scales in, like, low customer accounts. Because say you're say you're a company that can only have 200 like, the fortune 200 or whatever. Let's just say the fortune 50. That that's the only group of people you could have as customers.
David:
It's still useful in that regard because you're still selling reputation and values and trust and all this stuff. And it's gonna look wildly different than, say, what brand might look like if you're Coca Cola or something. Right? You're appealing to a different audience. The things you're you're sort of showcasing as your values change.
David:
But it's one of those things when you recognize that you can understand then why it's important because it it lets people know what you represent. And so, you know, as over the last few years, I've developed a I'd say I wanna say more knowledge, but at least more of an opinion thesis around this brand stuff at Century. And we thought a lot about it. It was like, well, our brand is actually authenticity is a big part of it. And and it's really important to understand that brand is it'll accompany like Sentry, but it I think at most companies, it's gonna come from, like, a founder or a a leader or something.
David:
It's gonna come from, like, a person, not 20 people. Just like everything is gonna come from one person for the most part. Product vision's gonna come from one person. Like, it doesn't always mean it's, like, the top person in the company, but everything successful comes from one person because you can't have a shared vision, generally speaking. Like, the way I paint this is gonna be wildly different than you paint this.
David:
Even if we're looking at what we're supposed to like, we have this exact replica in front of us. Right? And so so a lot of our brands stem from me and what I believed in and things. So things like, let's make a really good product is, like, part of what I care about, or let's just be honest. Let's be sort of tongue in cheek humorous.
David:
Like, all those things are things I believed in. And then you hire other people that also believe in those things, and that's how you kinda scale it out. But so for Century, we've used that in a lot of ways. Like, we're not good at demand generation, and I think part of it is and so, actually, let me step back. So Century's business, if you're if if anybody listening doesn't kind of grasp it, we have something like 65,000 paid logos.
David:
And what you should take away from that statement is we are extraordinarily large for an enterprise business, like in terms of logo count. And to contrast that, we are in the application performance monitoring category, APM. I'm gonna give you two other examples of companies you have heard of in that category, New Relic and Datadog. When those companies went public, they had around 10,000 logos. And mind you, the companies, those logos paid a lot more money than the average person pays Century, but the scale is different.
David:
Thus, the way you execute on the business is wildly different. Right? Like, one core tenant we have is part of that, which you could say is in our brand. It's not quite in terms of how we represent it, but it it is a core value is, well, the product has to be accessible to get that many people, let alone to say get a quarter million logos. And so part of accessibility is affordability, and all these other things go with it.
David:
And so when we think about brand and and just marketing in general, it's like, well, how do we get 250,000 logos? Well, you're not gonna buy, you know, a billion dollars worth of ads to do it because it doesn't make any sense. Like, it's like, how do you get there? Well, the the way we get there, the way we found effective because we've not found anything else, it just brought awareness. Like, if people know what we do, they know what we stand for and why we're good at it, and and they have a use for what we do, for what we build, like, they get they would get value out of it or they have a need for it, they will likely buy our product or at least consider buying our product.
David:
And then when they try it, they'll see it's good or they'll connect with our values, and then they will buy it. And that that works. And that to me is brand in a nutshell. Right? And you can slice and dice that any way you want.
David:
There's there's so many amazing businesses that are represented purely on brand like Porsche. Like, I'm I I love Porsches. If I say Porsche and you know anything anything whatsoever about that that manufacturer, you have some opinion about what they represent. Right? Like, I would tell you, like, their handling is amazing.
David:
Like, the the the design is like, all these things, these attributes that they kind of expose. And it's you can't just talk them. Right? They have to live them. And so, like, a a counter actually, a negative brand can exist too.
David:
Like, back in the day, I don't know if this is true. I'm I'm not that much of a car guy in this sense, but, like, Fords were known to always break down or something. That was effectively part of their brand for better or worse. And so it's kind of interesting when you think about it that way. But to me, brand is what do people think of when they think of your brand, you as an individual or you as your your company, and you need to make sure those are the things that are actually relevant, that are actually gonna drive customers and whatnot.
David:
And so it's just it's an interesting and it's also fun because brand is like a lot of different things. It can be your opinions. It can be visual design language. It can be clever humor and stuff. You know?
David:
There's there's lots of different ways you can slice and dice it. So I think also as somebody who is not really a creative person but aspires to be a creative person, it's just one of those fun areas that allows you to be you or to do the things that you sort of believe in, and which are usually, like, the right things to be fair. And they just help drive success.
Jack:
Yeah. Yeah. So it's like your purse it's like leaning into your kind of what your company does and who
David:
you It's leaning into your belief system Yeah. In a lot of ways. Right? Remote remote first is actually a big thing people put brand behind because they believed in it. A lot of them did at the very least, and that helped them.
David:
Like, it did maybe it didn't sell their product, but it helped them hire or something. You know? And it's like other people that are like, yeah. I believe in remote first. That company represents my values.
David:
You know? And that that's like the an obvious one that you see at face value. But a lot of brand is just kinda like, if you ask yourself, you would be able to answer what what is that that a value like you know, Liquid Death is one of my favorite more recent brands. It's because, like, if you know what Liquid Death so Liquid Death is water in a can, flat water in a can for the most part. And they make a lot more money than Century at this point.
David:
They've grown phenomenally. They're brilliant at marketing. And you gotta ask yourself, why do they make money? It's it's like I love this saying. I never read the the thing, but there's this old thing that people would espouse, like the five whys.
David:
It's like root cause analysis. And you basically just keep trying to drill down till you feel like you've gotten to the bottom of something. And I always like to think that way in a lot of stuff. And so it's like, well, why like, what is interesting about Liquid Death? They make a lot of money, and they're a new entrant to the field, and they just sell flat water.
David:
So why did why did they make a lot of money? And it's hard to say, you know, because brand can mean different things to different people. But one thing I think they did extraordinarily well is they sold it's like anti marketing is what they call it now. But they sold water in a can that kinda looked like beer, and you kinda look cool drinking it. Like, in fact, I was at a concert a festival in Vegas.
David:
This was, the when we were young. It's all the pop punk nostalgia, the only water they sold was liquid death. And I'm like, damn. They did well. They did well.
David:
And that was only possible because they already had the brand. Right? Because everybody's competing for those kind of positions. But the brand is so like, that one's fun because the brand is so wacky. You're like, if you try to reason about it, like, isn't it, like, using algebra or math?
David:
It's it's not gonna make any sense. You gotta reason about it with, like, emotion. Like, why would somebody choose that? Well, I've got this boring can of water here, and I've got this cool can of water here that basically looks like somebody put a tattoo on a can. I'm like, I'm gonna go with the tattoo can.
David:
You know? Because it's it's gotta admit, like, this visceral emotional reaction often. And I actually this is the same thing I would say is, like, you know you have product market fit. Now when you look at some funny math formula that, you know, a consultant came up with, When when you show it to somebody and they are just like their eyes light up and you're like, holy This is cool. Like, you get that emotional reaction, that's when you know you've achieved something.
David:
And I think it's the same for all of these. And and so I I just think that they're, like, they're really interesting analogies, you know, to to why would you choose a company or a product, you know. It's not because it has the coolest feature set most of the time.
Jack:
Yeah. I felt like you like, it's very I don't know, like, Century is like very like it does really genuinely have like a very like it feels like it's gonna have a full like everywhere you look, even in the dark corners, it's gonna be well made and kind of like I remember when I first heard about it and before I used it, like, I asked my friend and he was like, oh, yeah. Sentry's great.
David:
That's good. We have a lot of problems, which again, you can never settle for for it's good.
Jack:
With the context of how you think. Yeah.
David:
But also a lot of people would agree. And I think it's one one of the challenges you get when you get to sort of the multiproduct stage, is where Sentry's been at for a few years, is just inherently everything gets more complex. The problems you're trying to solve are more complex. The solutions are more complex, and it's really hard. And and, like, I think one of the most useful skills in at least product I don't I don't know if you could apply this to everything, is simplification.
David:
You know, engineers love to flex deleting code. I don't care about deleting code, but the one thing I would agree with deleting code is it simplifies a problem. Right? And the more simple you can design a solution, the better it is. No matter what, almost certainly.
David:
Right? And inherently, like, one one problem century has at our scales, there's a lot of complexity. Like, because we have so many customers, which also makes every like, even the brand marketing stuff, really complicated. It's really complicated to do something that you actually know will have any real result. It's like our our current thing that we I I I don't know if we just launched it this week or whatever.
David:
It's like, we're doing this roast of century where it's like, just talk about it. We're like, this will be funny. Who know who knows if it'll be successful, it'll be funny. Also, maybe we'll get some product feedback and maybe it'll ground some people and humble them and stuff. And and I I I think at the very least, there's a a practical lesson you could take away is, you know, think outside the box.
David:
A bunch of blog posts and buying some ads on Google is not gonna make you successful. Like, the industry is way too big, you know. And so if you can stand out a little bit and if you can do it in an authentic way the authenticity basically helps because it grounds you in what actually might be useful, it's really valuable. You know? And so but but, yeah, we are not without our flaws that we are continuously trying to address.
David:
So
Jack:
Interesting. But that that all matches with your your personal brand, your personal beliefs, like, even just like Roast. Roast Century is, like, kind of, like it makes so much sense given the conversation we've just had.
David:
Imagine imagine Salesforce doing something like this. They wouldn't know. Like, they're like a what is Salesforce's brand? Stiff corporate company? Like, with a bunch of salespeople that you don't wanna pay for?
David:
Like, I'm like, what is their brand? What do they stand for?
Jack:
Yeah. Well, there is almost a brand of, like, people dissing Salesforce these days anyway. Like, that's almost a brand in itself.
David:
Yeah. And I actually think the risk and maybe the I don't know. Because like, I only know what I've lived. Right? I wonder if there's a risk that a lot of companies start up with a great brand.
David:
Like, they they have a lot of great value they're adding, people believe in it. And then there's a point where either they lose their way or it's too hard or you can't maintain it where it turns. Right? Because once upon a time, people certainly loved Salesforce. Right?
David:
Yeah. It represented something they truly cared about or IBM or pick one of these companies that PC people don't like whatsoever. You know? Oracle. Once upon a time, they were certainly not that way.
David:
I'd like to believe they were not that way. And it's interesting because not every company is that way, and, actually, some companies recover. Like, look at Microsoft. I actually think Microsoft right now, it's a little weird, but, like, rewind three years or something or four years when they went big on open source and all the stuff.
Jack:
TypeScript. Yeah.
David:
Phenomenal brain recovery in in sort of the developer community. And, like, I'm a Windows I exclusively I have a MacBook, but I almost exclusively use Windows these days. Mostly because I just think it's a better experience now. And I also like gaming and all, and I do a bunch of, like, photo stuff, which is just easier for me on Windows. But I'm like, so you can fix it if you choose to fix it.
David:
But, also, that choice has to come from the top. Right? Like like Yeah. That change was when they hired Satya, like, massive pivot. And now it's unclear because they're big on this AI thing, it's a little gimmicky.
David:
But it's just really interesting if you try to analyze these companies. I don't know. It's become one of those things because I don't really get to build interesting software anymore, And you always gotta find a thing that I don't know if motivation's the right word, but, like, kinda keeps you energized and excited. And and I think that always has to stem from learning. And so for me, this brand and sort of these larger company, like, bigger than us journeys and stuff are what has been, like, really interesting to me in recent history and have kinda kept motivating me to to grow and and learn more and whatnot.
Jack:
That's amazing. Okay. So last two questions. One is, are there any dev tools that you're excited about at the moment?
David:
I will say though the one thing I I'm a skeptic by nature. And this AI hype wave reminds me of the crypto hype wave where everybody's trying to get rich quick. And so super skeptical about a lot of it, but also because I'm not an idiot. Like, it's very easy to see through stuff. But I will say we adopted Cursor in recent history of Century.
David:
I very rarely buy tools at Century. I'm very anti waste money. I was really impressed with Cursor. And, primarily, just the type ahead was, like, so damn phenomenal. And so, like like, really happy with that.
David:
Also, the guy seemed really I I don't know any of them personally. I'm not an investor. I wish they had called me before they raised any money. I would have happily invested. But the folks I've interacted with also seem insanely smart.
David:
You know? So that I I really, really big fan. Beyond that, I'm like, have I used anything even? Like because I don't use much software. Like I mean, I have a few side projects I spin up that I run on various hosting services.
David:
I, like, use I have, like, some Hello World LLM rag thing like everybody and their mother. This one does, like, it tries to answer questions about board games because, like, if you if you ever play board games, inevitably, you're like, wait. What happens in this? I ain't gotta dig through the rule book. And I'm like, LLMs can definitely solve that.
David:
And so I built something with that that I run on Vercel, which is generally a really good developer experience. I I wouldn't say I'm a fan of the JavaScript, you know, dev tool scene in general because it's just a lot of complexity. And I have this whiskey thing I've been working on. But, like, my problem is in a lot of them. Nothing's really excited me for the most part in terms of, like, groundbreaking ideas or something that's made my life so much more pleasant.
David:
And I think part of it is because I don't I still can write code fairly confidently, but I'm not really a developer these days. You know? When I'm writing code, I'm just, like, hacking around on stuff. And so it's it's been hard to find stuff. I I think there is a lot of interesting stuff happening in the space, to be fair.
David:
But I do bias towards sort of, like, I live in the JavaScript ecosystem. What does that tool chain look like? What if things do there for me? And I'm very old school as well. You know, like, I run a bunch of Kubernetes stuff on a service called Northlink because it's not that hard for me.
David:
Will.
Jack:
Yeah. He's he's from The UK. I love Westlink.
David:
Yeah. It's like the Canadians. Everybody knows each other. But, yeah, it it's like it's been pretty good. Mostly because, like, there's if you look now around, everybody's like, giant cloud provider, which is insanely expensive, VPS, which I'm scared of, mostly because often you have to handle your own security or something.
David:
Or it's like this past abstraction, which then requires eighteen third parties, and I don't wanna spend, you know, a thousand dollars a month on my toy project. Granted, my my whiskey website somehow still cost me, like, a hundred and 50 a month, but it's overengineered. But again, beyond that, like, there's not been much that's like really made my life significantly easier. I am really excited about what Tanner Linsley is doing in the JavaScript community with TAN stack, which because I'm a big LAMP guy from back in the day, like normal web stack request response cycle. I understand these paradigms super, super well, and I think they're good, and they're well established and mature.
David:
And I think he's probably the closest to bringing something that looks like that to the JavaScript ecosystem, particularly the sort of the front end rendering cycle, which to me is sorely needed. But beyond that, I I haven't actually done a lot. You know, I it's like I mostly just, like, try to entertain myself and continue learning outside of work hours these days. And so it's very rare that it actually ends up, like, using any kind of tooling or or even writing code unless I'm really feeling it some days. Maybe that'll change this year.
Jack:
We'll see. That's super cool. And then very last question. If you had to kind of like just like one piece of advice to like an early stage DevTools founder that just, they'd really really want them to hear.
David:
Two one sense snippets. Don't build a damn status quo thing. Don't build logs or something like that. Like, you will fail overnight. So don't just build something that exists for no good reason.
David:
Like, don't pivot. That's like, the same thing. Just don't don't do that. And then just try a lot harder than you are trying. And, like like, success is just grind.
David:
There's nothing more to it. You can be successful at any terrible idea. You probably be successful at building a law company. You need something that's a little different because, like, just it's crowded. You don't wanna be in a super noisy space.
David:
That's why the AI space is really complicated right now too, but but I just don't think people try hard enough. I don't think they actually recognize what that means. Like, don't have a family and expect work life balance with 16 children and start a company. Do something else. It's not for you.
David:
Your life's gonna suck. Your family is gonna be a disaster. Like, it it takes sacrifice. It's really hard, and you have to grind. You know?
David:
It just it's the reality of it. Whether people want it to be true or not, it is. You know? Like, I I don't have kids yet as an example, and I am almost 40 now, which is, I think, boredom. I'm too like, a little late in life for it, but but all I did was work.
David:
In my twenties, I did nothing else than work. Yeah. Sure. I'd go out at night sometimes with folks and whatnot, but I, you know, sun up to sundown. I'm basically, like, with peers grinding away at stuff.
David:
And that I think is also what helped me, like, make Sentry successful, particularly early days. So
Jack:
Mhmm. Yeah. That's really good advice. Try hard. Try harder.
Jack:
Mean,
David:
Try harder. I think I think
Jack:
it's like sacrifice.
David:
It's the one thing you
Jack:
can control. Yeah. Amazing. Well, David, thank you so much. It was, really an honor to speak with you, someone I've admired for a really long time.
