The Ledger, every show

“You can basically turn anything into a hundred million dollar business these days. Like the technology is really big. 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 t…”

“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…”

“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…”

“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.”

“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 …”

“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 pass because Uber's not gonna pay anybody. And we've just removed that. An…”

“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.”

“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.”

“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?”

“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 no…”

“Like that era for me is like when the internet was like very creative, like 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 don't know, it's different.”

“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 complexity code. Like it's a registration form or something like that. It's not a hard problem. It…”

“Do not start a lifestyle infrastructure business. It doesn't work.”

“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 …”

“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.”

“And I actually argue today, most technology is still worse than that.”

“I'm like, I know 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 going to go remove that objection. And that, that to me is like, definitionally how you get a product market fit. And I ac…”

“The companies are driven by the founders and sort of key executives, but generally 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 actual…”

“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.”

“They'll be like, ah, well, the reason we don't have more customers is because of marketing. I'm like, no, you just don't have more customers because it's not good. It's not useful. Not, and it could never be useful or it's just not useful yet.”

“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 …”

“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.”

“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 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 th…”

“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.”

“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.”

“And so I'm a big fan of the echo chamber that is San Francisco. It's good and bad, but generally more positive.”

“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.”

“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…”

“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.”

“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.”

“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…”

“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 us…”

“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…”

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

“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…”

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