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Christopher Pitts understood the value of a good education growing up in Birmingham, Alabama, where he first learned to love science and math, and it was that foundation that propelled him to earn an electrical engineering degree in college.

But when he began tutoring math classes in Hannibal, Missouri, as a volunteer during his spare time after graduation, he witnessed the strong disparity in learning outcomes between students living in rural and urban areas.

“I’d been very fortunate that I went to schools with a lot of resources, and teachers were able to adjust their methods to me and other students who performed like me in order to [enhance our] performance,” Pitts says. “That is one key aspect I saw missing in some of those areas.”

That’s when Pitts started toying with the concept of a software platform that could provide teachers with more accurate, efficient data on their students’ performance. Partnering with Ima Richburg, a former classmate who specializes in STEM education, Pitts created Calypso.

Essentially an automatic grading system, the software leverages artificial intelligence and data analytics to score assignments, including handwritten responses. “The mission of Calypso is to bring equity in education to every child in the developed and undeveloped world,” Pitts says.

How does it work? A teacher uploads a test, a test key, and the students’ paper tests, and the Calypso system takes care of the rest. Any response the software can’t decipher is flagged for teachers to review. Upon completion, both the student and teacher get a digital copy of each completed assignment, as well as a table of the results from everybody in the classroom. The goal is to liberate teachers from tedious grading and instead focus on the individual learning needs of each student.

“We take the speed of Scantron testing, but also do it for handwritten answers,” says Pitts. “We want to provide value to the students and teachers, so we’re having to make sure that we cater our tech to what assessments are going to look like in the future. Once we really homed in on focusing on digital assessments, we started to get a lot of traction.”

Calypso is entirely bootstrapped at the moment, and the team just now started to write and send out letters of intent to potential investors. However, they already have a growing base of enthusiastic teachers, students, and superintendents in Houston and the Midwest who've signed up for beta testing as of January 2020. (Coronavirus-related closures have pushed that date to October 2020.)

Pitts is also involved with the New Teacher Center and the Chicago branch of the Obama Foundation, which have both helped him get in touch with administrators, community leaders, and teachers in the Indianapolis and Chicago areas.

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Perhaps the biggest learning curve for Pitts has been handling Calypso from a business perspective — an aspect he's focused on with his mentors at the Founder Institute, an accelerator program from which he graduated this year.

“At different stages of your company, you need to get the right kind of mentors,” says Pitts. “Neal Murthy and James Phelan [from the Founder Institute] have been really integral to me removing my tech hat and thinking about establishing business partners with whom I can establish mutually beneficial relationships.”

“The best lesson I have learned throughout this process is to go for as much smart advice as you can, but also develop the ability to vet what you hear,” he adds. “There’s going to be a lot of right answers, but there’s going to be a specific right answer for what your specific situation calls for.”


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