Mastery is essentially being challenged and getting good at what you do ... Autonomy is essentially the freedom to be able to do it. So, you're not being micromanaged ... Purpose is working for something bigger than yourself. I think that it's very difficult to drive world-changing performance if it's just for a paycheck or just for your own personal benefit—you need to be connected to something larger.

If you're able to design an organization that [allows for] people popping in and out at whatever time zone or whatever times to fully contribute and move forward with goals in a meaningful way, then you unlock access to the world's talent; you unlock ultimate flexibility in everyone's day; you give people a ton of autonomy. And, I believe asynchronous interactions can be far richer than synchronous ones.

There's a quote I love from Hafez: 'Fear is the cheapest room in the house. I would like to see you living in better conditions.'

I actually hired a CEO; I consider him like a co-founder—Tony Schneider. He's like my business soulmate. And one of the things he taught me early on was 'make reversible decisions quickly and irreversible ones deliberately,' and I still return to that on a weekly basis.

We all operate on pattern recognition, and most of these patterns are subconscious ... I think, far too often, do we truly invest in creating deliberate patterns—ones that don't just happen by accident but that we truly challenge, and choose to adopt in our life, and actually practice.

I think it's really hard to go wrong if you... pursue wonder and awe. You can probably overdo it... but I think there's a wonder deficiency in most lives.

I'd say that very much Automattic is a written communication culture. And I believe clear writing represents clear thinking, and we filter for this in our hiring, and we talk about writing a lot.

I do believe in the cosmic insignificance. It's very humbling to think our timespan, even all of human recorded history, is just a speck of dust of the universe's timespan.

Markets always trump anything one individual or company can do, and I think WordPress is a great example of that.

I think meaninglessness can be terrifying, but in a way, it can also be liberating, because it frees you to kind of do whatever you choose to pursue.

Automattic, from the beginning, has been distributed. [We have] people working from all around the world. Today, it's about 1,300 people in 77 countries in almost every U.S. state [and] I think four of the provinces in Canada.

Everything is always changing. I'm not good at staying still.

I think it's easier to slack off in an office than it is in a distributed environment.

I believe all proprietary software to be an evolutionary dead end.