“As an intellectual person, I wanted to understand everything about everything,” he says. “We would be running a play and I would say, ‘Why would he cut behind?’ [My coach] would say, ‘Don’t think about it. Just do what I said.’” His coach once wrote “K.I.S.S.” on O’Kelley’s shoe as a reminder to “Keep it simple, stupid.”

At the time, O’Kelley looked up to his older, more experienced teammate, Miguel McKelvey. In a way, McKelvey was his opposite – a smooth, instinctual player who went on to play college basketball at the University of Oregon.

That was back in the ‘90s. Nowadays, the former teammates have more in common: they’ve each built a billion-dollar company.

AppNexus, which O’Kelley started in 2007, is an advertising technology company most recently valued at $1.2 billion. WeWork, the brand of co-working spaces McKelvey launched in 2010, carries a valuation of $16 billion. Their headquarters are down the street from each other in New York City’s Flatiron district.

At AppNexus, other members of South Eugene’s basketball team pepper the ranks. They include the SVP of marketing, the director of product management and the data science manager.

While these sorts of connections aren’t rare in startup land, they often can be traced back to college – Google’s founders met at Stanford, Mark Zuckerberg met his co-founders at Harvard. It’s unique that the founders of two individual unicorn companies would have played basketball together at a public high school in Oregon. And both say the experience helped them become the leaders they are today.

A high school of excellence

South Eugene High School, located in hippie-friendly Eugene, Ore., is situated less than a mile away from the University of Oregon, the city’s top employer. Eugene and neighboring Springfield comprise what’s known as the Silicon Shire, a hub of high-tech manufacturing south of Portland; Nike actually got its start in Eugene and the city last year was named one of the 10 up-and-coming cities for tech jobs. According to 2014 Census data, the population of Eugene is approximately 160,000, and 93.3% of its residents have obtained a high school degree or higher. Out of 326 high schools in Oregon, South Eugene ranks ninth in the state, according to U.S. News & World Report.

But those are just numbers. O’Kelley says it was the type of people who chose to make Eugene their home – professors, entrepreneurs and former athletes – that made it “a perfect incubator” for ideas.

He remembers how a fellow classmate’s parents kept getting arrested for chaining themselves to trees in hopes of saving them from getting chopped down. In the same class was a student whose dad made big money from working for a company responsible for cutting down those very trees. “You could have these incredibly controversial debates, but everyone would then hang out and be friends,” he says.

The fact that O’Kelley, 38, and McKelvey, 41, have remained friends 20 years after competing for stardom on the basketball court is a testament to how they learned to handle conflict at South Eugene. “If you look at these companies we’re building – these are companies full of conflict, but people can then walk out the door and play ping–pong together,” O’Kelley says.

A basketball bromance

Though O’Kelley and McKelvey say they welcome conflict today as a result of what they learned at South Eugene, there were some boundaries they did not cross – especially when it came to basketball.

Dean Stepp, South Eugene’s head basketball coach from 1977 to 2000, led his teams to the state tournament 19 of those 23 years. He had three big rules for his players – get to practice on time, don’t shoot outside the key, and never use your left hand to play. (Stepp was unavailable for an interview.)

To this day, O’Kelley remembers being publicly humiliated by his coach in front of 2,000 people for shooting when he wasn’t supposed to. And that has stuck with him through the years as a lesson of what not to do. “Walking around our office, I’ll sometimes think, ‘Am I pulling a Stepp? Am I yelling at people in a way that humiliates them? Am I taking away their chance to do something,’” he says.

McKelvey, however, appreciated the coach’s rigid routine. The WeWork co-founder describes himself as “a wild kid” who was bumbling around the court. “I remember Coach Stepp as the most strict disciplinarian I’ve ever come across,” he says. “I didn’t grow up with my father, so I never had someone telling me to keep in line.”

Basketball practice was typically each day after school and sometimes on weekends. Pat McCarthy, AppNexus’s SVP of marketing and fellow teammate, vividly recalls those early morning drills.

“You go through those 7 a.m. practices where you’re working so hard, you throw up in the corner. You go through those times when someone on your team misses the game-winning shot and is crying in the locker room,” he says. “Brian [O’Kelley] and I moved from playing together to working together.”

All’s fair in business and basketball

Because of their relationship on the court, O’Kelley and SVP of marketing McCarthy’s entrepreneurial careers have intersected pretty much every step of the way. The duo fixed and sold old computers in high school, ran a web development company out of their dorm rooms in college, and worked together at O’Kelley’s first advertising startup Right Media post-grad. McCarthy then ran his own startup, Fantuition, until O’Kelley acquired it in 2012. Today, McCarthy, 39, runs marketing out of AppNexus’s satellite office in Eugene.

McKelvey’s entrepreneurial career took a different path, but he never lost touch with his basketball buddies. After college, he started his own company called “English, baby!” – a social network for people learning English as a second language. But he decided he wanted to change direction. After five years, he moved to New York to take a job at a small architecture firm. His experience there led him to launch WeWork.

McKelvey’s biggest challenge has been the social and emotional journey of running a startup – but he takes comfort in knowing that there’s someone down the block who knows how he feels. While they don’t spend much time together, the two former teammates still get together for the occasional basketball game. And they’ve never broken Stepp’s biggest rule – always be on time.

“I still have this internal stress,” McKelvey says. “I’ll be late to a meeting, but I’m never late to a basketball game.”