Jon’s solution worked well for the biggest realities Dropbox was facing at the time. What the style did have, however, was a well-reasoned argument for why it would work. He was the most connected to the users, and Jon was damn good at connecting with an audience at a universally human level. After all, in the early days, Jon worked in customer support. Ok, not really - it was actually just a meeting, but in that meeting, co-founder Arash Ferdowsi passionately fought for Jon Ying’s vision. It took a long, drawn-out Dance Dance Revolution battle between the two founders.

This decision was hashed out in an absurdly unconventional way. In the early days of a company, these decisions can become hard to untangle, as it’s often two heartfelt, passionate beliefs pitted against each other. People started writing in and tweeting to apologize for hurting us by leaving. The image we made was a weeping PC with a thought bubble with a broken heart inside. “I made a drawing for an email campaign sent to people that recently downgraded from Dropbox Pro. He believed it could even help retain customers through some tough times. However, Jon believed simple universal drawings connected on a human level and inspired empathy when things might not be working right. The drawing could actually cost the company. If they didn’t trust that Dropbox was going to take care of their needs, they were out. Who are we? Should we be just like all the other respectable companies and play it safe? Or should we try something interesting and make a statement? The decision to publish the stick figure wasn’t easy, but it was an important decision. The image portrayed a stick figure chasing after a bug with the intent to smash it to oblivion, and it sparked an intensely debated existential question for the company. Jon Ying, who does not consider himself an illustrator, drew a piece for a blog post about some bugs they were working on. Illustration at Dropbox comes from very humble beginnings. First illustration drawn for Dropbox by Jon Ying

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