Staying the Underdog

At the end of last summer, my first startup was acquired by Chegg. We had around 70 employees at the time and revenue growth was strong. Our vision was to create a global brand in education and we were well on our way in doing that. Chegg gave us an offer we couldn’t refuse so we took it. That exit was a huge success for everyone involved and I’m honored to have been part of it since starting it out of my Princeton dorm room in 2006.

Because of that successful journey, I’m often invited to speak at universities, join panels at events, or judge business plan competitions. I get phone calls, emails and other requests from young entrepreneurs seeking advice. Some would argue that I’ve “made it.”


That feeling is a death kiss no matter who you are – but especially if you’re a successful entrepreneur chasing a new startup dream. It’s a dangerous feeling – complacency isn’t easy to wake up from.

It’s rare for entrepreneurs to have multiple successes. It remains insanely difficult to create something people want whether you’ve done a successful company or not. Odds will always be against you. Just ask Kevin Rose.

I think the best entrepreneurs preserve that underdog mentality no matter how successful they become. They treat their next thing like it’s their first. They keep that chip on their shoulder and work like it’s day one. They’re still willing to run through brick walls and work harder than anyone else. They remember that their poop still stinks and that nothing will come easy.

Guarding, cherishing and preserving those feelings are key. I’m still sitting at the kids table. I’m still on the outside looking in. I’m still that scrappy, young college dropout that no one will listen to.

I’m still the underdog. And this underdog won’t rest.


Now read this

For the Single Founder Who Can’t Code

This post originally appeared on TechCrunch as a guest post. Last summer when I started working on Undrip, I was in a tough spot. I grew up doing web and graphic design so I was a pretty good front-end developer and designer. But I knew... Continue →