How Drew Houston Made His Tech Fortune

Drew Houston is the 38-year-old co-founder and CEO of DropBox. In recent years, he’s made one sizable stride in his entrepreneurial career after another. In the process, his net worth has continued to soar to unimaginably impressive heights.

So how did a computer science major from Massachusetts become one of the wealthiest people in America before turning forty? It certainly wasn’t something that happened overnight. But inevitably, preparation and luck met opportunity at just the right time.

Let’s take a look at how the co-founder of one of the biggest tech companies out there made his mega fortune.

His Early Career

Andrew Houston graduated with a degree in Computer Science from the Massachusetts Institute of Technology. It was at MIT that he first met Arash Ferdowsi; they would eventually become the co-founders of Dropbox. However, getting there would take some trials, errors, and a few failed attempts.

Long before Dropbox, Houston tried his hand at several other start-up ideas that didn’t pan out. He also worked on other well-known start-ups as he learned the ropes. The most well-known projects he contributed to include Bit9, HubSpot, and Accolade. Other business ventures never got off the ground or were rejected or revamped, but they all laid the groundwork for what was to come.

In the mid 2000s, Houston was still working towards his billion-dollar idea, even if he wasn’t quite sure what it was yet.

Launching Dropbox

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Like many great ideas, Dropbox started out as a simple solution to a common problem. In an interview with Business Insider, Houston recalled how the idea for his leading tech company came to be. One day, he’d absent-mindedly left his thumb drive at home. According to Houston, this was not the first, second, or even fifth time he’d forgotten it, but it would soon become the last.

He told Business Insider he never wanted to have this common, yet majorly frustrating occurrence happen again. So he thought up a solution to his annoying problem. “I opened up the editor and started writing some code. I had no idea what it would become,” he revealed.

By 2007, Houston and Ferdowsi co-founded Dropbox. He was 24 years old at the time. The co-founders secured $15,000 from the start-up funding firm Y Combinator. The following year, Dropbox officially launched. Houston has said that DropBox took significantly longer to get off the ground than other startups–but that was no accident. More than once, Houston has stated he knew DropBox was the type of company that they “had to get right” for it to succeed. And how right he would turn out to be!

Even Apple CEO Steve Jobs expressed interest early on and called DropBox “a great product.” When Apple asked if they’d be willing to sell, Houston declined the offer. To some, saying “no” to Apple seemed like a pretty big risk for a somewhat young, albeit booming, company. But Houston’s move turned out to be well played in the end.

Achieving Unprecedented Success

Today, Houston remains the CEO and owns about 35% of Dropbox. The file and storage sharing service has 5 million users. The San Francisco-based company is now a global powerhouse, revered as one of the best of its kind from the West Coast to the United Kingdom. And it’s not just individuals who are using DropBox; the wildly successful startup has officially welcomed over 150,000 company signups.

The accolades keep pouring in, too. Houston was named one of “the most talented players in the technology industry” by Business Week. To date, Dropbox is ranked as one of the most successful investments from Y Combinator. In turn, Houston was also dubbed one of the top entrepreneurs under 30 years old several times after Dropbox took off.

Thanks to Dropbox, Houston has the means to pursue whatever projects he wants, so he continues helping others by giving back where he can. In 2014, Houston put his creative problem-solving skills to good use. He became the co-founder of a lobbying group called FWD.us. The aim was to lobby for immigration reform and lasting educational improvements.

His Personal Life

Thus far, Drew Houston is not married. Unsurprisingly, the thirty-something billionaire finds himself on the “most eligible bachelors in the world” list year after year. While he’s not quite off the market, he’s reportedly in a serious relationship and has been for some time. Houston is said to be dating a woman named CeCe Cheng. Cheng is a graduate of Princeton. Currently, Cheng oversees PR for the New York City-based startup Qwiki. 

He might be one of the wealthiest and most eligible bachelors on earth, but Drew Houston is said to be a humble guy. In his free time, he likes to sing or play video games and sports in order to unwind. Just like everyone with a day job, he’s endured his fair share of burnout over the years. And he has no problem admitting it.

Dealing With Burnout

In a Q&A for the Bits and Pretzels podcast, Houston got real about how hard it can be to be the CEO of a top tech company. Despite his success, he felt himself stagnating. Houston explained, “I’m in meetings all day, inbox all night, and then wake up and repeat, and it was bizarre because I couldn’t remember the last time I was using my brain. I was working really hard, but feeling I’m making less progress.“

Houston warns that burnout might be inevitable in the start-up world. He notes that we’re using our brains so much more these days, adding, “I think we’ve hit a breaking point of how much we can process.“ He says that as an entrepreneur, being on call 24/7 was not in his, or anyone’s, best interest.

Taking his work everywhere had to become a thing of the past in order to move forward and get his drive back. In other words, Houston finally learned the importance of “work-life balance” the hard way. In turn, he was able to reapproach his work refreshed, with new ideas once again, and fully ready to bring home the billionaire bacon.

Drew Houston’s Net Worth

When asked how he achieved such incredible success in his field, Houston is refreshingly humble for a tech billionaire. However, Houston does credit the company he keeps. As far as business philosophies go, he believes that the people you surround yourself with count for more than one might think. In fact, Houston has repeatedly said this played a vital role in his long-term and ongoing success. He advises others to stick with “inspiring people” when aiming to focus on their goals and succeed in their careers. Perhaps his keen awareness for what works is what ultimately led to his billionaire status in 2021.

These days, Drew Houston is regarded as one of the youngest self-made billionaires on the planet. Earning his tech fortune as the founder and CEO of Dropbox has paid off in some very big ways. In 2018, the cloud storage provider finally went public. Reportedly, shares jumped more than 35% on their first day. Still holding over 20% of the company, Houston remains the largest individual shareholder of this two-person startup turned global enterprise.

Currently, DropBox’s CEO has a reported net worth of $2.2 billion in the bank. And potentially more. Some sources calculate his estimated net worth closer to $3 billion.

His Next Big Career Move

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Steve Jobs wasn’t the only high-power CEO to know real innovation when he saw it. It was only a matter of time before others reached out to Houston with major offers. Next up was Mark Zuckerberg.

The Facebook CEO expressed interest in what Dropbox was doing and eventually struck up a deal with Houston. In 2020, Drew Houston joined the Facebook board of directors. In a statement about Houston’s role, Zuckerberg said, “Drew brings a valuable perspective to our board as a leader of a technology company with services used by millions of people and businesses,” adding that he “thinks deeply about where technology is going” and has the know-how “to build a culture that delivers services that always work well.”

We may not what Drew Houston will do next, but his career trajectory is worth paying close attention to. While he continues to make a six-figure base salary, Dropbox’s seemingly unstoppable revenue growth began falling in 2020. Perhaps this explains the career move to serve on Facebook’s board? Forbes called the decline “a dark cloud on Dropbox’s horizon.” But is it really? Only time will tell. Revenue is said to be on track to drop another 10% percent by 2022, but maybe that looming cloud will pass.

After all, Drew Houston could very well land on his next billion-dollar idea when he least expects it. He’s done it before.

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