Overcoming Rejection: Lessons from Dropbox Founder Drew Houston

In 2013, I had the opportunity to meet Drew Houston, the founder of Dropbox. During our conversation, he shared some insightful thoughts on handling rejection. 😮

When I was at Y Combinator (YC) as a founder, Drew Houston was one of the speakers. During the Q&A session, I asked him about his experience with rejection. Here’s what he shared:

Early Rejections and Lessons Learned

The first time Drew applied to YC, he had an SAT prep idea called Accolade Online SAT Prep, launched in 2004. However, he got rejected. The rejection letter stated, “There has to be something you can build better than an SAT prep company.”

Undeterred, Drew spent a year brainstorming a new idea that could get him into YC. He applied again and faced another rejection. ☠️

The Breakthrough

Three years later, in 2008, Drew came up with a groundbreaking idea: a web app that "synchronizes files across your/your team's computers. It's much better than uploading or email because it's automatic, integrated into Windows, and fits into the way you already work."

This idea evolved into Dropbox, which is now valued at $7 billion.

You can let rejection stop you, or you can let it drive you. The hustle never stops.