Check out Dropbox CEO Drew Houston Journey to success

The file-sharing service that began as a two-person team in 2007 is now a sprawling enterprise with more than a thousand employees and a stock ticker symbol that’s soon to be listed on the NASDAQ. The cloud storage giant now provides services to more than 500 million people and generates a billion dollars in annual revenue.

In October, he was named to Forbes’ 400 list for the first time, ranking among the wealthiest billionaires in the United States.

But things weren’t always easy for Houston or his company. He struggled with his initial entrepreneurial venture and faced several obstacles getting Dropbox off the ground. Dropbox has taken 10 years of growth to get to the point it’s at now.

But Houston hung in there. Despite multiple opportunities to sell his company in its early stages — including a bid from Steve Jobs in 2009 — he held on.

Houston started programming when he was as young as five years old. He began working on ideas for startups when he was only a teenager. Before his junior year at the Massachusetts Institute of Technology, Houston took a year off to work with a former high school teacher on a test prep company. The company’s goal was to help students get perfect scores on the SAT college admissions test.

He founded Dropbox about two years later in response to a personal technical problem. While riding the Chinatown bus from Boston to New York, Houston realized he had left his thumb drive containing files he needed at home. The initial idea for creating Dropbox was born out of his immense  frustration over leaving his thumb drive behind.

Arash Ferdowsi, then a student at MIT, had reached out to Houston after seeing a demo video Houston put together for Dropbox. After a conversation that lasted no more than two hours, Ferdowsi agreed to drop out of MIT and work with Houston. Houston compared his business deal with Ferdowski to a shotgun wedding.

Dropbox’s initial funding came from Sequoia Capital after Houston met with the venture firm’s chairman, Michael Moritz. Houston said Moritz dropped by his apartment to discuss the deal. After the funding round had been agreed upon, Houston waited for the funds to go through. The debut came about a year after the company got its funding from Sequoia.

Apple expressed interest in Dropbox early on, and teams within Apple met with folks at Dropbox to discuss technical details of the service. Jobs then asked if Houston would be willing to sell to Apple. When Houston turned down the offer, the meeting became less amicable.

In 2013, Houston delivered the commencement address at MIT. He credited the school for Dropbox’s success, noting it was where he had met his cofounder, Ferdowsi.

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