It’s all uncertainty, right? That’s the default state of the world. But 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.

This is something I’ve learned from the brilliant product designers I’ve worked with; in my first two companies, I often wasn’t clear on any of those things. And I think that’s a struggle for a lot of founders. 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. Whereas if you can point to actual, living human beings who have the problem you’re solving, you’ll be much more eager to iterate through different solutions until you find one that works.

Something I’ve been trying to lean on more is asking my friends and mentors for help. It doesn’t come naturally to me—I’m much more likely to reach out if there’s something concrete I think we can work on together. But I’ve realized that’s silly; there are all sorts of things a friend or mentor can do, and it’s often most helpful when those conversations aren’t transactional or even specific.

I used to always resist discussing people-related problems, for example, especially with someone outside my company. But I’ve found that those are some of the most important concerns to discuss. If I’m worried a team member isn’t working out, and I get advice about it early on, there may still be plenty of time to fix the issue. I have a much better chance of repairing that relationship, versus just keeping the problem to myself until it gets worse.

I think the central thing is eliminating any conflicts of interest right from the beginning—and I don’t mean in the traditional sense, like self-dealing, though of course that’s also important to avoid. But what’s far more common is different stakeholders in the company simply wanting different things. I have cultivated an acute allergic reaction to anything that seems like it’s going to create that kind of friction, even if it won’t happen for a year or two.

This means you have to get a lot of things established very early on, from the kinds of contracts you want to have with partners to what your company policies and values will be. 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. I personally stay away from any kind of indirect revenue model, for example, because it sets up an immediate conflict between what customers want and what advertisers want. We’ve all seen how much damage can be done to the world when those misalignments happen, and you won’t know it’s coming if you don’t know the plan.

I can tell you two of the easiest ones: fundraising and shutting a company down. Both can be extremely unpleasant, but they’re also very straightforward. It’s clear what to do next.

Literally everything else is hard, because you’re never exactly sure what’s optimal. Your company might be doing pretty well—but could it be doing better? Are you spending your day in the best possible way? 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 vast majority of the time, it’s the latter. Maybe I have to fire an employee or a customer, and I really don’t want to. But I do know it’s the right thing to do, and no one is forcing me to be a CEO. So I just do it, and try to reserve my mental energy for the problems that are truly hard.

The first thing that comes to mind is eating apples whole—the core, the seeds, even the stem if it’s not too big. It freaks people out, and I’ve never seen anyone else do it. I just tried it once years ago, when I had a core I was too lazy to throw out, and it was actually pretty good. So I kept it up.

At work, one thing I used to do differently and I want to start doing again is asking job candidates for writing samples—even if they’re not applying to be a writer. I don’t really care what the writing’s about; I just want to see complete sentences and paragraphs. 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.

People usually try to weigh the pros and cons of different options, but that never works and you shouldn’t do it. 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. Sometimes that’s the right approach. If you’re guiding a nation through a pandemic, “least bad” may be the way to go. But we entrepreneurs are lucky in that probably 80 percent of the time, it’s better to do whatever creates the most good. So I always start by asking myself whether it’s a “least bad” or “most good” type of decision.

This is especially helpful in groups, because the more people making a decision, the more conservative and risk-averse the process tends to be. Pointing out problems makes you seem smart, whereas talking about what’s exciting makes you seem like a doofus. So sometimes I’ll go around the room and ask everyone specifically, “What’s the best thing that could happen?” Then we can talk about the downsides later, without it automatically leading us to something safe and mediocre instead of something awesome.

I think the “most good” framework from the previous question is helpful here, too, because it feels so wrong to talk about the positives when things are bad. Our brains resist it. And it’s definitely important to think about what we can do to mitigate problems. But for all the things that are worse right now, some things are better. Maybe it feels scary to hire people I’ve never met in person—but it means I can hire from anywhere in the world. Maybe we miss being in the same room for meetings and reading people’s body language—but we’re hearing far more from our brilliant employees who happen to be introverted. I think the opportunities come from leaning into those things that are better and asking what’s the most we can do with them—how we can supercharge what’s good.