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Aaron Levie's 5 Rules for Startup Founders (Rule 4: If You're Comfortable, You're Doing It Wrong)

By Aaron Levie · Mindset & Career · 1 min read

Levie shares the five lessons from building Box — from timing technology shifts to never writing your obituary too early.

Key Points

Do something that wasn't possible 3 years ago
Do something you're extremely passionate about
Don't compromise — think in terms of 'bests'
If you feel comfortable, you're probably not doing it right
Don't write your obituary too early

If you feel comfortable, you're probably not doing it right.

Do Something That Wasn't Possible 3 Years Ago

Levie: If you're looking at a business opportunity that you could have done 5 or 10 years ago, it might be too late. Or it might not be different enough to make a lot of people care.

Look for new technologies that are enabling your solution. Box wasn't possible in 2000. The enabling technology was cheaper storage, better browsers, more connected devices, faster internet.

Do Something You're Extremely Passionate About

Levie: Startups are very hard. There's a lot of bad news that happens every single day. Bad things in the competitive space, bad things with hiring. You have to be able to push on through.

You have to do something that's actually really exciting. Something you're going to be inspired about and that's going to create inspiration for other people.

Don't Compromise

Levie: One of the coolest things about starting your own company is you get to make a lot of decisions. You don't have to sacrifice on who you work with or how you're going to build your technology.

We think about things in terms of bests. What's the best team we can build? What's the best technology we can produce? What's the best way we can communicate? It's all in your control.

Think about things in terms of bests. What's the best team, the best technology, the best marketing. It's all in your control.

If You Feel Comfortable, You're Not Doing It Right

Levie: There are a lot of hard decisions. Who you're going to work with, how you're going to compete, are you going to raise money, are you going to leave school.

You're going to have to go well beyond your comfort zone. There are decisions that aren't going to be easy. That's actually a good sign. It's a good thing when you don't really know the answer and you make that leap.

If you feel comfortable, you're probably not doing it right. It's actually a good thing when you don't know the answer and you make that leap.

Don't Write Your Obituary Too Early

Levie: This is a mistake we've made a handful of times. We've been extremely competitive with Google and Microsoft and EMC — companies we normally shouldn't be afraid of. The venture capitalists are often afraid of these guys.

Don't write yourself off. Keep pushing. Make sure you're optimizing on the right dimensions and in areas where you can beat other people. That's why we still have the company today.

Don't write yourself off. Keep pushing. That's why we still have the company today.