I do think it’s important to have as much clarity as possible about the problem you’re trying to solve.You should know the emotional effect you want to instill, what the other priorities are, and most important, who you are serving and how.

It's tempting to start from seeing a cool technology and try to figure out what you can do with it, or from noticing a trend and trying to build from there. But if you aren’t clear on the problem, you’ll end up kind of lurching from opportunity to opportunity.

The issue I see most often is the business model—especially with venture-backed companies, because it’s easy to think, “Well, I have this funding now, so I don’t have to figure that out yet.” But it’s not about money. It’s about alignment.

When I’m doing something especially difficult, though, I have a framework that helps me, which is to ask myself, “Is this actually hard? Or is it just unpleasant?”

The first thing that comes to mind is eating apples whole—the core, the seeds, even the stem if it’s not too big.

Clarity in written communication is always important, more now than ever with everyone being remote. But mainly I think someone’s writing is a window into the person—their character, their style, their attention to detail, the way they think. I can get more out of 45 seconds of reading something a person wrote than I can in talking to them for 45 minutes.

The part of your brain that wants to prevent bad stuff from happening will almost always overpower the part that wants to make good stuff happen, and you’ll just pick whatever option is least bad.