Automattic

“And then that became WordPress.com, which allows us to host hundreds of millions of sites on the same code base, same databases, in a super scalable way where each incremental site only costs us like a penny per year.”

“I personally don't like that because it seems to take what makes open source successful and essentially, you know, create the incentives against it, right? Because if you play that out 1020 years from now, your very best features are going to go into the paid …”

“WooCommerce, which is, I think, one of the fastest growing e-commerce platforms in the world. It's essentially e-commerce built on top of WordPress, so you get the best of both. And that's doing well over twenty billion of GMV now and growing really quickly.”

“Internally, I get almost zero email. So inside the company, we basically don't use email. Maybe like some HR stuff or something you might get via email if it's truly private, but everything else happens on the blogs.”

“Going from 20 to 50 people, you lose that ability to brute force the collaboration and getting everyone on the same page, and you really need to start communicating in a way which is, Well understood across the existing people, but also at that point, you're p…”

“And it's now, 10 years later, it still has over five nines of accuracy for blocking spam and keeping and allowing good stuff through.”

“We had an offer at that time to sell the company for about two hundred million, and it was absolutely the right answer not to do it. But I was very close to, and it was partially because I was like, okay, that'll resolve these people issues. I won't have to de…”

“So our regretted churn is something like four percent per year, three percent, three and a half percent.”

“And so I really kept us sub 50, probably two or three years longer than we should have been. And so that meant that we got really spread thin and we under invested in things like customer service. Because I was trying to keep the company really small, because …”

“I believe asynchronous interactions can be far richer than synchronous ones. You unlock the power of the introverts in your company. People for whom, in a real-time meeting, they might hang back a little bit or be shy, or they might need to think about things …”

“So we were able to take 25, thirty million a year of cost out of Tumblr, just by kind of bringing it over to our systems, which brought them a lot closer to being breakeven.”

“It's like, is there anything I can do to help you? Versus What do you need for this to be a success? One is like putting the power with me to help you, and the other is putting the power with you to define what you need, and then I can support that, but ultima…”

“We turn down an investor who wants to invest in the company at a maximum of five hundred million enterprise value, and like, a week or two later, someone invested a three billion dollar valuation.”

“More than the money in our bank, more than our software, anything is this, ah, sort of now, kind of like a 15 year record of every decision, every design process, everything is in these internal blogs.”

“The problem we have actually in distributed work, so to get to another downside, is not under work, it's over work.”

“If every meeting is transparent and has really good notes, or a recording, people don't feel the need to be there, and so the meeting can be smaller. Which also means it's more effective, where it's like, you know, not everyone is like, ah, I'm not in this mee…”

“The only places where we'll do something really top-down is if there is a really large capital impact.”

“And I kept finding this ratio that's like 20 to one everywhere in successful platforms, not in fake platforms, like it's not on the Facebook platform. Facebook made like 90% of the dollars in that ecosystem, but in others.”

“We ended up reducing that to about 800. So we went from 6000 servers to 800 and part of that was, you know, doing a lot of engineering work to bring things on to sort of what we've learned with best practices and being super duper frugal with everything we bui…”

“We used to not track any vacation, or what we call AFK, away from keyboard time, because we have a completely open policy there, take what you want. But the problem was people weren't taking it, so we started tracking it to encourage people to take it, which i…”

“And then Tumblr, which actually was an acquisition we did last year, which is a, you know, one of our blogging competitors. We were able to acquire it, and we're redoing it, switching it to actually be powered by WordPress on the back end.”