From Dorm Room to the Cloud: How a Class Project Sparked Box’s $3B Journey
The unlikely startup tale of Aaron Levie, cold emails, and a contrarian bet on online storage before 'cloud' was even a thing
This story is based on Box CEO Aaron Levie’s MAD Podcast interview: Box’s Big AI Leap.
The Spark: An Unlikely School Project
Aaron Levie and Dylan Smith co-founded Box in 2005, while they were sophomores in college. The idea stemmed from a class assignment that required students to do a SWOT analysis of a market. While others chose giants like Nike or Walmart, Levie took a weirdly contrarian route: online storage.
"It was obviously the weirdest... everyone's doing like I'm going to choose Nike and I'm going to choose Walmart and I chose online storage."
But that odd choice kicked off a chain reaction. Levie realized the difficulty of moving data in 2004–2005—emailing attachments, USB drives, and external hard drives were the norm. At the same time, the world was shifting:
Storage was getting cheaper
Internet speeds were improving
People were using multiple devices
"Maybe there was this moment where you could access your data from anywhere... it wasn't called the cloud, but you put it on the internet."
This was the seed of the “cloud” as we now know it.
The Team: Lifelong Friends Turned Founders
Levie and his co-founders (including Dylan Smith, who is still Box’s CFO) were high school friends, some dating back to middle school. That long-term trust played a big role in starting a company while still in school.
"We had known each other for 10 years... incredibly lucky to have a friend group you can start companies with."
The MVP: Launched from College
Their first launch was simple, but real people started using it.
"Five people signed up the first week, then 20 the next. I started talking to the users... this was maybe what it feels like to launch a real company."
It was Levie’s first time experiencing direct user feedback, unlike his previous side projects. People emailed bugs, feature requests, and treated the team like a legit company—even though they were just replying on a BlackBerry in class.
Raising the First Money: Rejection and Hustle
Back home in Seattle, they tried to raise money. Every local VC passed on them. After three or four rejections, they found one investor who seemed “a little bit philanthropic”, putting in $20,000 and bringing three friends.
📌 First angel round: 240K–$320K
"We hadn't even heard of the word dilution... you’re telling me someone’s going to give us $80,000? Incredible."
They were in college. They didn’t know startup terminology. But the product was real, and momentum was slowly building.
The Mark Cuban Moment
Here’s where the story takes a turn.
Levie cold-emailed Mark Cuban, who famously replies fast.
"He got back to us in like 10 minutes and said, 'Interesting company.'"
That cold email led to a partnership discussion, which turned into an investment of a few hundred thousand dollars. It was a make-or-break moment.
"The company would not be around without him."
As part of the due diligence, Cuban had them meet Travis Kalanick, who was then working on Red Swoosh. Travis gave them the thumbs-up — and later inspired them to drop out of college when growth picked up.
Why Box Was Early—And That Was Good and Bad
They launched in 2005, just 6–12 months before AWS existed, which meant:
They had to build and manage their own infrastructure
They were selling cloud before cloud was cool
For a decade, banks and enterprises kept asking if they’d offer an on-prem version
"You’d go into meetings... they weren’t there to meet about your cloud version. They were just like, 'When is your on-prem version coming?'"
Still, they rode the wave of increasing trust in the cloud and grew alongside the market.
Reflections and Lessons
Rejection built grit: Getting rejected by all Seattle VCs early on became a resilience-building experience.
Timing mattered: Too early for cloud infrastructure, but just early enough to be a category leader.
Cultural foundations were strong: The company emerged from long-standing friendships and trust, which likely helped them weather tough transitions.
Cuban’s belief was catalytic: His quick response, investment, and network played a pivotal role in Box’s survival and early growth.
"There’s probably 2,000 or 5,000 people with a story like ours. Mark Cuban replied to a cold email and changed everything."