Johannes Simon/Getty Images, Steve Jennings/Getty Images
Box CEO Aaron Levie (right) and Dropbox CEO Drew Houston
Box cofounder and CEO Aaron Levie, known as being one of the funniest guys in tech, likes to quip about Dropbox:
"Any time you ever want to see what Dropbox will do next, look for what we did 3-5 years ago."
Levie famously tweeted that in 2015 about Dropbox's products for corporations and has said similar things many times before and since.
Dropbox CEO Drew Houston finally got his chance to lob a dig back at Levie, on Monday at the Fortune Brainstorm Tech conference in Aspen.
When asked about that quote from Levie, Fortune's Dan Primack challenged Houston to name one thing his company has done before Box.
"Generating cash," Houston said without missing a beat. The audience laughed.
Houston was referring to Dropbox's recent announcement that it is cash-flow positive. This means that Dropbox has a certain amount of "freedom" because its main operating business is generating actual cash after you account for the capital expenditure costs.
Box, on the other hand, had a famously rough attempt to IPO, when the world freaked out over how much cash it was burning on sales and marketing to grow its customer base. Box still remains operating cash flow negative, but has said that it will turn cash flow positive by early next year.
On the business models, Primack pushed Houston to name a product feature that he thinks is a first. He said Dropbox Paper, a feature that lets you create and edit apps in Dropbox on the web (a la Google Docs).
Paper was announced in October, 2015 (it's still in beta).
Box's document editing feature, Box Edit, isn't exactly the same. It taps into the Office apps installed on your computer (like Microsoft Office) to let you edit documents from within Box. But it was announced in March, 2015.
That said, Houston seemed quite comfortable taking on Box. Dropbox has had bigger success with consumers. Dennis Woodside, Dropbox COO, said on stage that Dropbox has 500 million users, is adding 10 million users a month, has 8 million paying users and 200,000 business customers.
Box says it has 39 million users and 50,000 organizations as customers.