Drew Houston, Founder, Dropbox

  • Dropbox founder and CEO Drew Houston started doing focused deep dives into an aspect of business he didn’t understand while he ran his first company.
  • To keep learning, he and his Dropbox leadership team read and discuss a book per quarter.
  • One of their favorite books is Clayton Christensen’s “Competing Against Luck.”

When Drew Houston took a year off from MIT to start Accolade, an SAT tutoring company, it didn’t take him long to realize that outside of the product side of things, he had no idea what he was doing.

Houston, who would go on to found Dropbox in 2007 and lead it to over $1 billion in annual revenue, explained what it was like for an electrical engineering student to get a real-world crash course in business in an episode of LinkedIn founder Reid Hoffman’s podcast “Masters of Scale.”

“I realized that I did not know anything about sales or marketing or financing a company or managing people,” Houston said. “And the list gets pretty long pretty quick — and not a lot of time to learn it.”

On a whim, he decided to go on Amazon and type in a specific topic, like “sales marketing strategy,” and order one or two of the top books. He would fly through these books, he said, and soon started treating them like textbooks, taking notes to absorb the information.

It worked so effectively that he decided to bring the habit to his leadership team at Dropbox. Now, Houston and his executives read a new business book every three months and discuss it at their quarterly offsite leadership meeting. He also recommends a book ahead of larger, biannual company meetings.

Houston told Hoffman that one of his team’s favorite books from this reading series is renowned Harvard Business School professor Clayton Christensen’s 2016 book “Competing Read More Here