At 20, he cold-emailed Mark Cuban and landed a $350,000 investment—now the company is worth $4.6 billion

CNBC

19-05-2025

Cloud storage and file-sharing business Box is worth $4.6 billion. It might never have gotten off the ground 20 years ago if Mark Cuban hadn't been closely monitoring his email.
In 2005, Box CEO and co-founder Aaron Levie was still a student at the University of Southern California, where he was developing a cloud-based data storage startup from his dorm room. Since the company needed funding to get started, co-founder Dylan Smith contributed roughly $20,000 he earned playing online poker.
Then, the summer before their junior year of college, Levie and his three co-founders — Smith, Sam Ghods, and Jeff Queisser — received an $80,000 seed round from angel investors to help them get Box incorporated as an official business and launch their initial product, Levie says.
Still, the founders knew they would need a lot more to build out the platform and attract enough customers to turn it into a viable business. So Levie started sending cold emails to every potential investor he could think of, including Cuban, he says.
"If you were [even] remotely an investor in 2005, you got an email from me," Levie says. He estimates that he reached out to dozens of investors from "anywhere in the world," starting in his hometown of Seattle, then expanding out to Silicon Valley and even Cuban in Texas. "If there was any theoretical chance that you could invest in the company, I was probably emailing you."
Cuban responded just a few hours after the students reached out. The billionaire entrepreneur and then-owner of the Dallas Mavericks initially proposed working together on a data-hosting project for one of his businesses, Levie says. "But then it basically expanded from there."
Cuban agreed to invest $350,000 before he'd even met Levie and his Box co-founders in person.
"That was wild, because it happened so fast," says Levie. Cuban's funding represented Box's "breakthrough investment," he adds, which gave him the confidence to drop out of college and focus on building the company.
Cuban maintains a public email address and checks it regularly. As of 2020, he received up to 1,000 email pitches per day, he told CNBC Make It ibn November 2020. However, the billionaire is a tough sell: Cuban estimates he deletes roughly 90% of those messages and it only takes him a couple of seconds to decide if he's interested, he said.
Levie insists Cuban received "the same pitch as everyone else," consisting of Levie's observation that online data storage was getting cheaper, the internet was getting faster, and with more people using a variety of devices for work and personal use, there was an opportunity for a company to make it easier to securely store data online and allow people to "work from anywhere," he says.
So why did that resonate with Cuban, specifically? Cuban did not immediately respond to CNBC Make It's request for comment. Levie believes the tech billionaire "was just very primed for that pitch," particularly because Cuban's time developing the streaming media market in the 1990s likely meant he was familiar with the need for more online data storage options, the Box CEO says.
"I think our pitch just landed at the right time with him," Levie says.
Still, the Box co-founders weren't sure Cuban would respond so quickly, or at all. In fact, Levie admits that basically all of his cold email pitches "were shots in the dark." But that was the idea, he says: "I don't know what part of my brain didn't develop properly, but I don't see it as any risk of pinging people and pitching people [out of the blue]. You just have to have as many at-bats as possible."
Levie offers similar advice to young entrepreneurs today. "Email everybody," he says, reasoning that you have little to lose by doing so. "Most of the time they're not gonna respond. But the good news about math is you'll catch the one that does, whether it's an investor or a prospect or somebody you want to hire. So to this day, I love emailing people [I want to work with]."
Working out of Smith's parents' attic in Mercer Island, Washington, and then from Levie's uncle's garage in Berkeley, California, the co-founders put Cuban's investment to use. They hired contract engineers who helped develop their product and put money toward server costs, online marketing and a 1-800 phone number for customer service, Levie says.
"We didn't pay ourselves anything. This was just purely, like, 'Let's grow the business as much as possible,'" he says.
Just a year after Cuban made his investment, however, the billionaire had a change of heart. He and the Box co-founders disagreed on the decision to pivot to a "freemium" business model where Box gave away a free gigabyte of online storage to attract more customers. Cuban didn't like that idea, or the fact that Box would have to take on additional venture funding to subsidize the cost of customer acquisition, Levie said in a 2012 interview with design company Zurb.
Box raised more money in 2006 — a $1.5 million funding round led by VC firm Draper Fisher Jurvetson, according to TechCrunch — and Levie used part of that capital to buy out Cuban's stake.
In 2014, when Box went public in an IPO that valued the company around $1.7 billion, Cuban reflected on his decision to walk away. Cuban wrote on Twitter that he "would combust" if he was responsible for a business with losses that outweighed revenue, like Box's did at that point. At the time of the IPO, Box had still not yet turned a profit.
Box has posted an annual profit each year since 2023, though, with the company reporting net income of $129 million in 2024.
While their partnership was short-lived, Cuban's investment helped kickstart Box's initial growth — and, 20 years later, Levie vividly remembers the excitement he and his co-founders felt when he received Cuban's email.
"It's very surreal when you see the name of somebody that you hold in high esteem in your inbox," Levie says. "That's a very good feeling. It may have been the first time ever that I felt that rush of like: 'Wait, I'm sorry. Mark Cuban literally responded? His name is literally in the sender line?' We were just super pumped that it actually happened."