Jai Shekhawat stood out from the other MBA students in Howard Tullman’s class at Kellogg School of Management 22 years ago. He sat in the back row, never raised his voice, and kept a low profile. Rather than talk about his aspirations or accomplishments, he came to class prepared, and it quickly became evident that he was putting in the work behind the scenes to make big things happen.

“Jai is just as kind and self-effacing today as he was then,” Howard confides.

So how has Jai changed? Far from sitting in the back row today, he has successfully founded and sold a business for $1 billion, and is considered one of Chicago’s most successful entrepreneurs. In 2012, Jai was named Ernst & Young’s 2012 Midwest “Entrepreneur of the Year”, and has been recognized as an innovator in the Vendor Management Software (VMS) space.

In 1999, Jai took what he had learned from Howard and others and channeled it into a project that addressed a problem he was deeply familiar with. He started Fieldglass, a company that offers the world’s most widely used Cloud platform for the procurement of contract labor and services.

Over the past two decades, Jai and Howard have kept in touch and maintained a student/mentor relationship that has blossomed into a friendship. Howard credits Chicago’s unique business culture in part for helping to make Jai a success.

I know of few people with more enthusiasm, and being in his class gave me the confidence to eventually find my own path as an entrepreneur.

— Jai Shekhawat

“Chicago is different,” says Howard. “People here are loyal in a way that perhaps you don’t see on the coasts — we’re in it for the long haul. Loyalty is a competitive midwestern advantage, and we also have an economy that is good for entrepreneurs who have diverse interests.”

Chicago can’t take all the credit, though. Howard taught Jai early on that it takes five things to be successful as an entrepreneur: passion, preparation, perspiration, perseverance, and principles. These “5 Ps” are instilled in many of the young, hopeful entrepreneurs that come to Howard’s prestigious startup incubation program, 1871 Chicago. And Jai gives credit where it’s due.

“Back then and right up to today, I thought of Howard as half teacher and half preacher. He’s always spreading the gospel and excitement of innovation and entrepreneurship. I know of few people with more enthusiasm, and being in his class gave me the confidence to eventually find my own path as an entrepreneur.”

Always the teacher, Howard deflects with more praise of Jai’s work ethic.

“Of course everybody wants to be the next Jobs, but with Jai, we sensed that he had the determination to be really successful. Perhaps more important than talent or anything else is the ability to keep your head down and stay focused. Half the battle is keeping your butt in the chair. Jai’s got that.”

What does one do after selling a company for $1 billion? In Jai’s case, he’s staying active in the city’s entrepreneurial scene with Howard at 1871, but he’s also focused on making Chicago the best city it can be by way of social activism and community service. He is heavily involved with an inner city academic program called MetroSquash, which helps to teach underprivileged urban youth how to play the unlikely game of squash while devoting an equal amount of time to academics. In doing so, MetroSquash mentors teach them dedication and discipline,two traits that Jai discovered are crucial to making it in his much-loved city.