Dropbox
Most of his wealth comes from his ownership in Dropbox, the online file-storage and collaboration company that shot up to a $10 billion valuation in 2014, just seven years after its founding.
There are a lot of different reasons for Dropbox's success, but Houston pointed to one quirky reason during an exclusive interview with Business Insider: an illustration of a happy cupcake.
Houston said the picture of a smiling cupcake is meant to represent his commitment to keeping a fun office culture, which he believes has been instrumental to the company's rapid growth, and helps him instill the same kind of easy-going mindset to the rest of the company.
It's why he even made the image of a smiling cupcake (with no additional words) one of Dropbox's five core values.
"We believe that just because you're in a corporate environment doesn't mean you should be sentenced to having a corporate experience. We think work should be fun and human and you should have great relationships and we try to imbue our tools with that sense," Houston said.
In fact, according to Kurt Varner, a recently hired designer, Dropbox actually delivers a cupcake kit to all new potential hires following an interview.
"The icing on the cake was this little pink box that greeted me on my apartment doorstep that night...I eagerly opened it to find a cupcake kit with a letter-pressed note from Dropbox expressing their excitement about the potential to have me join," Varner wrote in a recent blog post.
And for those wondering, here's the full list of the five core values at Dropbox:
- Be worthy of trust
- Sweat the details
- Aim higher
- We not I
- "Cupcake image"