Sentry

“Their first product they ever built and prototyped was? It was called Century, but it wasn't the tower. It was a autonomous firefighting tank that would roll into a forest fire and could deploy, like, fire suppression”

“As agents start to do work that is not writing code, but more general work, again, for software engineers or beyond for any builder, they're gonna need to start interfacing with other systems. Right? So as they start, maybe your agent is talking to Sentry, rig…”

“We also think the next evolution is going to be beyond code repositories because again, As much as IDE and AI system and code repository is like the home for developers, that's not the only place that they work in. It's always like the prod is down. Okay. So y…”

“I feel like in a way the MCPs are like, Cannibalizing the products themselves.”

“I would say pretty much if you were building a Django 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 Django, but like some third party thing, like century was b…”

“We had, so we're a little bit different. Like we were bootstrapped 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…”

“Here's a mistake I think of all founders. Not all. Majority of founders make. And, you know, we know the SaaS majority of 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 …”

“There are no new industries, generally speaking. 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 Century was in 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? Doesn't mean they're not valuable 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 still exists roughly. It's self-hosted. I don't know. I don't think we ever would have gotten here.”

“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 want to be in that business. I don't want to sell on-prem software. I don't want …”

“We have some stuff that looks promising, but like I would not claim we have product market fit on, on the rest of our suite yet.”

“I gave up board control. I hired a CEO to take my job. I hired a CTO to take my job.”

“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 I think today, a third of revenue is sales, which is not that much at our scale, right?”

“FedRAMP will be one of the last things we ever do, or maybe China, 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 customer…”

“The core version of Sentry, the air monitoring component, does not look that different than it did 1015 years ago.”

“We have this tracing product. It is, you 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 h…”

“And that is like the P zero of the entire company is like, we have to solve JavaScript first. And it's because we recognize that was the growth of the industry. And I think, I don't remember where I got this data, I just quote it forever, was the first year wh…”

“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 forec…”

“Enterprise companies cannot compete with us when we undercut them on price, when we undercut them on market share, when we are the developer's first choice.”

“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 …”

“You can't apply their successes. It just doesn't work. Like, great. Century has product market fit. There's nothing you can learn from how we achieved it that you can apply to your business. Cause it was like, Just fortunate. Coincidence, right?”

“We're at a lot of conferences, for example, we don't get ROI out of most of those.”

“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 SMB or the mid market or something. And so many people do thi…”

“All the tech that makes Sentry valuable is permissive open source. And for example, we have this one technology used by every single competitor in the world, you know, from the biggest to the smallest. We give that away for free.”

“If you get, I don't know, say your ten 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.”

“We have 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, and it's like, activism.”

“So I think MCP or something like it is going to be the next major unlock because it allows systems that don't know about each other, don't need to just decoupling of Like Sentry and whatever tools someone else was building.”

“We were literally taking desktop GPUs GPUs and liquid cooling them to get these things to work in a hot desert under solar power.”

“We were able to go and get a prototype up in about three months and then move into like a pilot in about six months and then a full scale in about two and a half years.”

“If you go to Sentry, which is one of these error tracking tools that a lot of developers use, they already have a beta feature right now where if there is an error, it tries to figure out why that error exists. And then tries to suggest a way of fixing it and …”

“Sentry, a lot of people don't know this, but Sentry is like a three billion dollar company. I think they do like nine figures and ARR, like it's a big business.”

“This is the decade for data and developers, the one we are in. The prior decade was cloud and SaaS, and the one before that was software-defined everything.”

“I'm a big proponent that even as companies transition out, and I know some of the founders get tired, but how do you preserve their first principle thinking, the value thinking, the intensity of how they thought about the first product and where it could go? I…”

“You don't sell to developers. You know what I mean? Like there's no selling to developers. You have to just show up in the right way.”

“Pricing and packaging was done by product marketing at VMware initially. Everyone was technical. They understood the product. They could actually You know, demo and sell the product, which helps. Some of the same principles we're using now at Sentry which is y…”

“It starts in-house with our own developers. Are you going to use it? Are you using it? If you're not going to use it, why the hell do you think some other developer at another company is going to use Sentry for solving that scenario.”

“From around 20 odd million to now north of a hundred, which we crossed last year during this period of time.”

“Number one, the software, a SaaS offering is exactly the same as the open source offering. There's no feature delta. So as a company, you can run the fully functional, up-to-the-minute value of Sentry on your own without paying us anything.”

“We've just crossed a 100,000 SaaS orgs because of the sustained kind of commitment to building a great product, being in the community, making sure access is easy, and then participating in the community.”

“There was art from pricing and packaging prior art, which is, it's X dollars, and we're like, Now, for the way we operate, we don't want to be at X dollars. We're going to basically focus on adoption. It helps kind of solve this problem, which is our core mark…”

“The art of saying no is the best thing a product manager can do to actually eventually win in a product, right? Because you, typically have like one company. You're basically jamming their features. Oh, I'm paying you ten million dollars. You've got to do this…”

“What we had built initially was successful. Double digit millions in like 18 months. It was growing thousands of customers and everything else.”

“When you are trying to be a large, sustainable, long-term company, you have to go after new, net new opportunities. They have to be adjacent though, so they can't be completely disconnected. So the way we said it is, this needs to be able to win as a standalon…”

“Means if you take a VMware or any other enterprise company, they package it up. It's all good enough. We'll be number two, number three. Distribution, ELAs, life is good whether it gets used or not. Can't afford to do that. If you are in the developer land, I …”

“The issue really is the fact that these observability companies isn't actually doing observability for the system, it's just doing the LLM thing. Like I still end up using like Datadog, right? Or like, you know, Sentry to do, like, latency. And so I just have …”

“Even at Excel, our first investment in Slack was a seed. Our investment in Sentry started as a seed. Our investment in Cloudera was an EIR.”

“The first investment I led in Century was at a six million dollar post money, and we purchased about 20% of the business. That was five years ago. Scale, the first deal was at a fifteen million dollar post money, and we bought 25% of the business.”