Ashish Rangnekar (BenchPrep) & Michael Alter

Ashish Rangnekar, MBA ’11, grew up in a sleepy town in India where success looked like a white-collar job, not entrepreneurship.

But early on he encountered a problem: he had few resources to prepare for college entrance exams. A decade later, when he was living in New York and planning for the GMAT, he realized test prep options were still lacking outside of lugging a big book around or attending expensive in-person classes.

It was the dawn of the Apple app store, so Rangnekar and a friend launched a mobile GMAT test prep app, priced it at $9.99 per download, and hoped some friends might sign up. In the first month, it was downloaded by more than 1,000 people in 20 different countries.

“That was the first aha moment,” Rangnekar said.

The second “aha moment,” he said, was when he won the 2010 Edward L. Kaplan New Venture Challenge, giving him the confidence that his little test prep business could make it big.

BenchPrep, headquartered in Chicago’s Willis Tower, is now an online learning platform for standardized tests as well as professional certifications, credentialing and training. It has raised $28 million, partnered with 50 learning organizations and helped 7 million learners. It counts more than 130 employees.

In a conversation with Michael Alter, a clinical professor of entrepreneurship at Chicago Booth, Rangenkar, BenchPrep’s CEO, reveals the stumbles along the way – including how the company regrouped after a deal to be acquired fell through at the last minute.

“That was the moment of reckoning,” Rangnekar said.