In 2011, Drew Houston was invited to Apple headquarters, to meet with its late founder Steve Jobs.
Houston is the cofounder and CEO of Dropbox, the file-sharing service with more than 500 million users. It generates $1 billion-plus in annualized revenue, and was valued at about $10 billion in 2014.
“I had talked to a bunch of my friends, and the stories fell squarely in two categories: You either got Chill Steve or Very Mean Steve, so we didn’t know which one we were gonna get,” he told Business Insider US editor in chief Alyson Shontell on an episode of Business Insider’s podcast “Success! How I Did It.”
It seemed that things kicked off with Chill Steve: “So we went into the boardroom, and you’re looking around the walls, and it’s just this pantheon of all the Mac products or all the Apple products over the years, you know, from the original Mac onward, maybe even before,” Houston told Shontell. “And so everybody sits down, and he leans back in his chair and he’s like, ‘Where to begin?'”
After telling Houston that Dropbox had a “great product,” he asked if Houston was willing to sell. “We told him that we’re really enjoying building this, we really admire everything that Apple has done, but we want to stay independent,” Houston said.
“And so he started trolling us a little bit, saying we’re a feature, not a product, and telling us a bunch of things like that we don’t control an operating system so we’re going to be disadvantaged, we’re going to have to figure out distribution deals, which are risky, and sort of a bunch of business-plan critiques. But then he was like, ‘Alright, well I guess we’re gonna have to go kill you, basically.’ Maybe not in those words, but pretty close.”
However, Houston told Shontell, it didn’t worry him overly because the issues Jobs presented were universal — “Apple has the same issue if they want iCloud to work seamlessly on Android or any other platform. And if anything, we were much more focused on solving this problem.”
“I didn’t want to get into much of a debate or make him angry,” Houston continued. “I was just like, don’t make him mad, leave a reasonable impression. That was the only goal.”
After Jobs was done trolling Houston, he stayed about an hour to chat, and even answered Houston’s questions and gave him business advice.