Enterprise

The incredible rise of Box CEO Aaron Levie, who stared down the naysayers to prove them wrong

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Aaron Levie
Box CEO Aaron Levie  Reuters

In a couple of weeks, Box will be celebrating its 11th anniversary. It launched as a corporation on April 8, 2005, with an $80,000 seed round. 

It's been a whirlwind decade for its charismatic founder CEO, Aaron Levie, in which he's been hailed as both a Valley wunderkind, and then as the master of a "house of horrors" and is now being vindicated once again.

Aaron Levie was born in Seattle, which means he grew up surrounded by Microsoft. When asked if he ever wanted to work there, he answered: "No."

bill gates 1992
Bill Gates 1992 AP Photo/Jim Davidson

Aaron Levie was obsessed with running an internet company from an early age. He launched about 15 companies as a teenager, including one called Zizap, which Levie jokingly described as "the fastest search engine on the Internet – minus Google."

Aaron Levie
Getty Images/Bloomberg

He founded Box.net with his friend from middle school Dylan Smith.

Box Dylan Smith Aaron Levie
Box co-founders Dylan Smith (left) Aaron Levie Box

Box was founded in a garage with his friends. In addition to Dylan Smith, he started the company with his buddy Jeff Queisser, who lived four houses down, and high school pal Sam Ghods.

Box founders
Box cofounders Twitter/@levie

He was just 20 years old when he founded Box. He dropped out of college to run the company, but he doesn't recommend that others drop out. "College is critically important."

Aaron Levie Box
Box CEO Aaron Levie Wikipedia/Fortune Brainstorm

(By the way: In 2010, co-founder Dylan Smith, age 24, appeared on an episode of Bravo's "Millionaire Matchmaker" reality show, where matchmaker Patti Stanger called him one of the nerdiest guy she's ever met and made him take dancing lessons.)

dylan smith dancing
Hulu / Bravo TV

The original angel investment was $80,000.

Levie landed billionaire Mark Cuban as an angel investor by sending him a cold email and asking him to invest. "He wrote us a check without ever meeting us," Levie said. He invested $350,000.

mark cuban
Mark Cuban, owner of the NBA Dallas Mavericks, speaks during the Wall Street Journal Digital Live ( WSJDLive ) conference at the Montage hotel in Laguna Beach, California October 20, 2015. Mike Blake/Reuters

For the longest time, Levie was known as that young, 20-something CEO. By 2011, he had raised over $158 million from venture investors. Then he had a growing-up moment when Citrix offered $600 million to buy Box. Levie turned the offer down, facing down his board full of investors who wanted to make their money back with that sale.

Aaron Levie talking
Box cofounders Aaron Levie (R) and Dylan Smith Flickr/Kevin Krejci

It turned out to be a good call. Today Box is a public company with a market cap of about $1.5 billion.

Box cofounders Aaron Levie (R) and Dylan Smith
Box cofounders Aaron Levie (R) and Dylan Smith AP

Levie always wanted to run a big public company but Box's initial attempt to go public was a disaster. Its IPO documents revealed that Box was burning through huge amounts of money to acquire customers. People were shocked at how the well-funded Valley startup was handling its cash.

Aaron Levie
Reuters

Mark Cuban, who was bought out a year after his initial investment, slammed the company at the time, saying he'd "combust" if he were responsible for the company's balance sheet.

mark cuban
Stephen Dunn/Getty

Box delayed its IPO several times, and Levie answered endless questions about it and the sustainability of his company. In early 2015 he finally took Box pubic and stock popped big on Day 1, making Levie's share worth over $94 million. He was 29.

Box IPO
Box rings the bell at the NYSE NYSE

Box shares haven't fared that well since, down about 48% from that first day pop, and below its initial IPO price of $14 per share.

Box shares
Google Finance

However, Box just passed $300 million in revenue in 2015, and most analysts are bullish on the stock, which is sweet vindication for Levie.

Box CEO Aaron Levie
Box CEO Aaron Levie Box

Aaron Levie is paying it forward with his success. He's a huge angel investor who has backed some 26 startups including Stripe, Gusto, and Instacart.

Box CEO Aaron Levie
Box CEO Aaron Levie GettyImages/Lisa Lake

Beyond the drama of the IPO, Aaron Levie is known in the Valley for a lot reasons. He wears colorful sneakers.

aaron levie shoes
TechCrunch / Flickr, J. Crew, Zappos

Sometimes he wears snazzy socks, too.

Aaron Levie shoes socks sneakers colorful
Here's a close-up of his favorite shoes and equally bright socks JDLasica via Flickr

Levie is also a magician. Here's a video where he performs some card tricks.

And he's hilarious, constantly cracking jokes. He once posted an April's Fool joke (and subtle dig at competitor Dropbox) in which announced he was merging with payments processor Square to form a new company called "Polyhedron."

Aaron Levie
Flickr/ TechCrunch Disrupt 2013

Because he's so funny, he's absolutely awesome on Twitter, with a running commentary on the Valley, the software industry, and even politics.

Aaron Levie Tweet
Twitter/@levie

If you're on Twitter, follow him at @levie.

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Julie Bort was Business Insider's Editor at Large for the Tech team. She loves investigating stories and shedding light on the tech industry's most amazing people.Here's a small sample of some of Julie's work.Former Pinterest employees describe a traumatic workplace where managers humiliate employees until they cry, Black people feel alienated, and the toxic culture 'eats away at your soul'Sex, tequila, and a tiger: Employees inside Adam Neumann's WeWork talk about the nonstop party to attain a $100 billion dream and the messy reality that tanked itInsiders say WeWork's IT is a patchwork of cheap devices and Band-Aid fixes that will take millions to fixWeWork's toxic phone booths were created in-house by its Powered by We business70-hour weeks and 'WTF' emails: 42 employees reveal the frenzy of working at Tesla under the 'cult' of Elon MuskElon Musk works so many hours at Tesla, employees are constantly finding him asleep under tables and desksHow this woman went from a Pizza Hut employee to a founder of a $4 billion startupAn Oracle insider explains how some salespeople gamed the system to sell more cloudTHE TAKEDOWN OF TRAVIS KALANICK: The untold story of Uber's infighting, backstabbing, and multimillion-dollar exit packagesMicrosoft is in talks to buy GitHub, a startup at the center of the software world last valued at $2 billionThe alarming inside story of a failed Google acquisition, and an employee who was hospitalizedInside Facebook's plan to eat another $350 billion IT marketHow a registered sex offender wound up living in an Airbnb hosting unsuspecting guestsA controversial ex-banker is the person who really runs Twitter — and he's gambling the company's future on one risky betSecret passages and skipped meals: Oracle's CEO gave us a rare peek at what it really takes to run a $37 billion companyHP told some employees to choose between becoming contractors with no benefits or being fired without severance'I felt like we were being extorted': Customer says Oracle tried to strong-arm him into a cloud saleHow the queen of Silicon Valley is helping Google go after Amazon's most profitable businessAirbnb host: A guest is squatting in my condo and I can't get him to leaveLIES, BOOZE, AND BILLIONS: How one of the fastest-growing startups in Silicon Valley history raised $580 million then spiraled out of controlGitHub is undergoing a full-blown overhaul as execs and employees depart — and we have the full inside storyWhen she's not writing for Business Insider, Julie can usually be found on the trails, on my mountain bike, or on my skis, if you know where to look.