No. 1: Hang Out With Geniuses
Surround yourself with the most brilliant people in your life. Don't have the ego to think you can do it alone because you can't. (At least, I don't think so.) It's your responsibility to find those people who you respect and trust, and who challenge you to make something greater than the sum of its parts.
"Even if there's challenge or difficulty or pain along the way, you won't even have a shot unless you go for it."
There are five of us who are cofounders [at Casper], and everybody always asks if that comes to blows very often. The answer I always give is that we have such different areas of expertise and such trust among us that it's often turbo-charging, because we have so many dedicated folks who are working so hard and so diligently, and we trust one another to collaboratively build our castle.
No. 2: Be a Builder
It's a natural tendency to try and figure out why something won't work. It's a really tough thing to focus on how it can work and what can make it work, and acknowledge that even if there's challenge or difficulty or pain along the way, you won't even have a shot unless you go for it.
"I was in my pajama bottoms on a Sunday morning trying to figure out how to get this website up and running because there was no one else but me."
The same could be true of Casper. There were a lot of naysayers before we were able to get to market. There were times when, if we'd been listening to the swarm of opinions, it just would never have happened.
No. 3: Figure Out What You're Good At
It takes a lot of self-awareness and a lot of humility to know what you're good at—and to know what you're not good at. Trial and error is the most tried-and-true method that I've found. You don't know what you're good at until you really give a fighting shot and keep doing it, if you really care about it.
"Home in on what makes you special and what you bring to the table."
Hold yourself to a higher standard and evaluate how you did on something. Be honest with your assessment of how you felt a project went. I think by really having a self-assessment that's not critical, not accusatory (but not grandiose or megalomaniacal, either), you can really home in on what makes you special and what you bring to the table.
No. 4: Expect the Unexpected
I remember our first big press hit, which I think was CNN. It was a Sunday morning and I wasn't really expecting anything big, and I wake up to a bunch of texts telling me that our website is under a little bit of strain. By that, I mean fully down. I was in my pajama bottoms on a Sunday morning trying to figure out how to get this website up and running because there was no one else but me.
No. 5: Always Be Flexible
We're over 250 people now in offices worldwide. For everybody in the company, myself included, that means that your job is changing all the time. It's harder to do the same job tomorrow than it is today because the stakes are increasing and your contributions have to increase commensurately. That's true for me, too. It's always an exciting challenge and an opportunity to think about what growth means in a new context, and how one can be most effective within that new context.
For more on what Casper is up to, see casper.com.