Eric Simons never did like doing things the normal way.

He’d been a below average student at his Chicago high school. Not because he didn’t have the brains to learn, but because traditional teaching methods held little interest for him.

It was when his chemistry teacher asked Simons how she could better engage him that his entrepreneurial mindset kicked in.

Simons suggested he build some software that would allow students to work on projects via the classroom computer. Eventually, the concept changed into ClassConnect, a company that allows teachers to create and discover lessons plans that they could then share with their students and peers.

“I said, ‘I’m going to take a crack at this’. I’m young enough that I can take a crack at some crazy stuff. Ten years from now, maybe I can’t be sleeping on people’s couches,” he told CNET.

And sleep on people’s couches he did. First, at the University of Illinois, where his school friends had commenced tertiary study, then in California, where he took part in the inaugural Imagine K12, a Silicon Valley project designed to mentor education-oriented startup founders.

Simons looks back at the program as a great source of inspiration, but the $20,000 he and his ClassConnect partners received to start the business barely lasted the four-months for which Imagine K12 ran.

His friends returned to college, but Simons wasn’t willing to give up.

Imagine K12 took place on AOL’s Palo Alto campus, and everyone involved had received a badge which gave them security clearance to the building. After the project ended, Simons tried the badge again…and it worked.

“I couldn’t afford to live anywhere,” said Simons. “I started living out of AOL’s headquarters.”

Having already spent four months in the building, he was a familiar face to AOL staff, who assumed he worked for another department. Simons found a desk, and began putting in 16 hour days coding ClassConnect. He’d work until midnight, before relocating to one of three couches he had found away from the paths of patrolling security guards. He’d sleep from 2 a.m. to 7 a.m., go to the gym to workout, shower, and wash his clothes, go upstairs to the free cafeteria, and then get to work as the actual staff arrived to begin their day.

Initially, Simons saw the experience as a game, but after a month, he started to get cocky. “Honestly, I didn’t think they were going to catch on.”

But they did. One morning, a security guard arrived at 6 a.m, and found Simons asleep.

Though he was angry, it was known that Simons was part of Imagine K12. His badge was revoked, but he was still allowed access to the building, where he continued to have meetings.

David Temkin, Senior Vice President of Mail and Mobile for AOL, stated “It was always our intention to facilitate entrepreneurialism in the Palo Alto office – we just didn’t expect it to work so well.”

It worked out for Simons too. A revised strategy saw ClassConnect receive $50,000 in seed funding from Ulu Ventures and Silicon Valley VC Paul Sherer.

“Tenacity and commitment are key attributes of a great entrepreneur. Eric has these in spades as demonstrated by his willingness to do whatever it takes to get his company off the ground,” said Ulu Venture’s Clint Korver.

The money allowed Simons to rent out a house, which he shared with his new staff – an engineer, and a couple of interns. The house’s spare bedroom was immediately listed on AirBnB.

That was in 2012. Today, Simons works as the co-founder of Thinksterwhich gives web and mobile engineers free access to educational information on various design platforms.

Can you imagine going as far as Eric Simons to bring your business to life? If not, why not? Let us know in the comments.

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