What began with a college student sending unsolicited emails to prospective investors eventually became one of the technology sector’s notable startup stories, after Box co-founder and CEO Aaron Levie persuaded billionaire entrepreneur Mark Cuban to invest $350,000 in the young company before the two had even met.
Today, cloud storage and file-sharing company Box is valued at about $4.6 billion, but its early survival was far from guaranteed. Two decades ago, Levie was a student at the University of Southern California, developing an idea for online data storage from his dorm room alongside co-founders Dylan Smith, Sam Ghods and Jeff Queisser.
The founders were trying to solve a problem that was becoming increasingly relevant as internet connections improved and consumers began relying on multiple computers and other devices. Their proposition was straightforward: create a secure online platform that would allow people to store their files and access them from wherever they were working.
But turning that idea into a functioning company required money, and the young founders had very little of it.
Smith, one of Levie’s co-founders, initially put about $20,000 into the venture from money he had earned playing online poker. Then, during the summer before the founders entered their junior year of college, they secured an $80,000 seed investment from angel investors.
That money helped the group formally incorporate Box and launch its first product. It was enough to get the company moving, but Levie and his co-founders knew it would not be sufficient to build a technology platform, attract customers and establish a sustainable business.
Rather than waiting for investors to discover them, Levie decided to approach potential backers himself.
The cold-email strategy that reached Mark Cuban
Levie began sending unsolicited emails to investors he believed might have an interest in the company. His search was not limited to established Silicon Valley venture capitalists. He contacted people across the United States and beyond, including Cuban, who was then based in Texas.
His philosophy was simple: if there was even a remote possibility that someone could invest, there was little reason not to make contact.
“If you were [even] remotely an investor in 2005, you got an email from me,” Levie recalled.
He estimated that he contacted dozens of potential investors, beginning with people in his hometown of Seattle before expanding his search to Silicon Valley and eventually reaching out to Cuban.
“If there was any theoretical chance that you could invest in the company, I was probably emailing you,” Levie said.
Among all those messages, one produced an unusually quick response.
Cuban replied only a few hours after Levie contacted him. At first, the billionaire entrepreneur and then-owner of the Dallas Mavericks proposed collaborating on a data-hosting project connected to one of his businesses. But the conversation developed into something much more significant for the young startup.
Cuban ultimately agreed to invest $350,000 in Box.
The remarkable part for Levie was that Cuban made the commitment before meeting the founders face-to-face.
“That was wild, because it happened so fast,” Levie said.
For the young company, the investment was more than another injection of cash. Levie described it as Box’s breakthrough investment because it gave him enough confidence to make a major personal decision: leaving university to devote himself to the startup.
The company had gone from a project being developed by students to a business with a serious investor backing its potential.
Why Cuban responded to the pitch
Levie has said he did not create a special presentation specifically for Cuban. According to him, Cuban received essentially the same pitch that had been sent to other potential investors.
The argument centered on several technological changes that Levie believed were converging at the right moment.
Online data storage was becoming less expensive. Internet connections were becoming faster. At the same time, people were increasingly using multiple devices for both professional and personal activities.
Those trends created an opportunity, Levie believed, for a service that could make storing information online easier and more secure while allowing users to access their files regardless of where they were working.
The central idea was that people should be able to “work from anywhere.”
Levie believes the timing of that argument may have been particularly important in getting Cuban’s attention.
Cuban did not immediately respond to a request for comment on the account, but Levie believes the entrepreneur was especially receptive to the concept because of his previous experience in technology and the emerging streaming-media industry during the 1990s.
That background, Levie reasoned, may have given Cuban an appreciation for the growing importance of online infrastructure and data storage.
“I think our pitch just landed at the right time with him,” Levie said.
There was no guarantee that the approach would work. In fact, Levie described his early investor emails as essentially “shots in the dark.”
But he did not regard sending them as particularly risky.
His view was that entrepreneurs should maximize the number of opportunities they create rather than spending too much time worrying about rejection.
“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],” he said.
For Levie, every unanswered email was simply another attempt that had failed, while a single positive response could potentially change the trajectory of a company.
Box was built without founders taking salaries
Cuban’s money gave the founders additional resources to turn their concept into a functioning operation.
The company initially operated in humble surroundings. The founders worked out of Smith’s parents’ attic in Mercer Island, Washington, before moving their operations to Levie’s uncle’s garage in Berkeley, California.
The money went toward practical necessities rather than lavish spending.
Box hired contract engineers to help develop the product and paid for server infrastructure, online marketing and a customer-service telephone number.
The founders also chose not to pay themselves.
“We didn’t pay ourselves anything. This was just purely, like, ‘Let’s grow the business as much as possible,’” Levie said.
The strategy was focused almost entirely on expanding the product and building a customer base.
But the relationship with Cuban would not last indefinitely.
Cuban eventually disagreed with Box’s strategy
About a year after making his investment, Cuban and the Box founders found themselves on different sides of a major strategic decision.
The company was considering a “freemium” approach in which users could receive a free amount of online storage as a way of attracting customers. Box planned to provide a free gigabyte of storage before seeking to convert users into paying customers.
Cuban did not support the strategy.
The disagreement was not merely about giving away storage. The approach also meant that Box would need additional venture financing to help absorb the cost of acquiring customers.
According to Levie’s account from a 2012 interview, those differences ultimately led to Cuban’s exit from the company.
Box raised $1.5 million in new funding in 2006, with the round led by venture capital firm Draper Fisher Jurvetson. Levie used part of that new financing to buy Cuban’s stake in the company.
Cuban was therefore no longer a Box investor, but his early contribution remained an important part of the company’s history.
From a $350,000 investment to a $1.7bn IPO
Box continued expanding after Cuban’s departure, eventually reaching the public markets.
When the company went public in 2014, its initial public offering valued the business at roughly $1.7 billion.
By then, however, Box had still not achieved profitability, a fact Cuban later highlighted when reflecting on his decision to leave the investment.
Cuban wrote on Twitter at the time that he would “combust” if he were responsible for a company whose losses exceeded its revenue.
The subsequent trajectory of Box, however, demonstrates how dramatically the economics of a technology company can change over time.
Box has reported an annual profit every year since 2023. In 2024, the company recorded net income of $129 million.
Its current valuation of approximately $4.6 billion puts the business far beyond the scale of the startup Levie was running from a college dorm room in 2005.
For Cuban, the early investment eventually became a decision he was no longer involved in. For Levie, however, the investment represented a pivotal moment when an unsolicited email suddenly produced a response from one of the most prominent entrepreneurs he admired.
Levie’s advice: keep making the attempts
The experience has shaped Levie’s approach to entrepreneurship long after Box’s early fundraising days.
His advice to young founders remains remarkably similar to the strategy that helped him reach Cuban in the first place: contact people directly.
“Email everybody,” Levie advises.
He acknowledges that most people will not respond. But that, in his view, is not a reason to stop.
The same logic applies whether someone is looking for an investor, trying to acquire a customer or attempting to recruit an employee. The entrepreneur does not need every person to say yes. The objective is to create enough opportunities for one of them to become meaningful.
“Most of the time they’re not gonna respond. But the good news about math is you’ll catch the one that does,” Levie said.
That philosophy proved particularly powerful in 2005, when one of those unlikely responses came from Cuban.
Cuban himself has maintained a public email address and has said he checks it regularly. In 2020, he told CNBC Make It that he could receive as many as 1,000 email pitches a day. Despite that volume, he said he quickly rejects most of them, estimating that about 90% are deleted after only a few seconds of consideration.
Levie’s email survived that filtering process.
The moment that changed Box’s trajectory
Two decades later, Levie still remembers the reaction inside the young Box team when Cuban’s name appeared in his inbox.
The founders were students attempting to persuade investors to believe in an idea that was still in its earliest stages. There was no guarantee that the company would become a major technology business, much less one worth billions of dollars.
Then Cuban responded.
“It’s very surreal when you see the name of somebody that you hold in high esteem in your inbox,” Levie said.
For the founders, the significance went beyond the money. Cuban’s decision to invest validated their belief that the problem they were trying to solve could become a substantial business.
“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?’” Levie recalled.
The founders were, in his words, “super pumped” that the gamble had actually worked.
Box’s journey from a dorm-room project to a multibillion-dollar company did not depend solely on a single investor or a single email. It involved years of product development, fundraising, strategic disagreements, expansion and the eventual transition into a profitable public technology company.
But the $350,000 check from Cuban remains one of the defining moments in its early history.
For Levie, it also became proof of the principle he continues to promote: sometimes the biggest opportunity available to an entrepreneur is simply the opportunity to ask.
At 20, Aaron Levie Cold-Emailed Mark Cuban for Funding — The Bet Became a $4.6bn Company
