Where Are They Now? Chicago Booth First Year Reflections with Sai Kumar

Sai graduated from West Point in 2018 and began his career as a U.S. Army Aviation Officer flying Black Hawks. Later, he transitioned to the U.S. Space Force as a developmental engineer, helping to field new weather satellites and pilot rapid-iteration acquisition strategies. When Sai decided to transition to the civilian sector, specifically into technology and startups, The University of Chicago’s dual MBA/MPCS program stood out to him as the ideal bridge. To Sai, it offered both the analytical rigor and entrepreneurial freedom to make a complex career pivot smoother. 

Having been at Booth for over a year now, does the academic experience live up to what you expected? Any favorite classes so far?

The academic experience has absolutely lived up to its reputation. Some of my favorite classes at Booth so far include Game Theory with Professor Emir Kamenica, Building the New Venture with Professor Scott Metcalf, and Accounting for Entrepreneurship with Professor Ira Weiss. Some of my favorite classes from the Computer Science Department include Design, Build, Ship with Professor André Marques and Discrete Mathematics with Professor Ishan Agarwal. The ability to immediately apply classroom concepts, whether through my VC internship or while building my own startup, has been transformative and helped me internalize what we learn.

Looking back on your first year, what are some takeaways, and what excites you most about embarking on your second year?

My first year was all about optionality, testing different paths and figuring out where I fit after the military. I’m grateful Booth gave me the space to do that, because it’s left me confident and energized about the direction I’m pursuing moving forward. That clarity and purpose is what excites me the most about my second year.

Where did you intern over the summer? Tell us more about how you secured your internship, prepared for the job, and what the overall experience was like.

Over the summer, I participated in Booth’s Entrepreneurial Internship Program (EIP), which allowed me to work full-time on my own startup while receiving a stipend. After spending an incredible and informative first year interning at Listen Ventures and engaging with founders, I realized I wanted to be on the other side of the table at this moment in time. The EVC community, my Booth courses, and the Listen experience all prepared me to take that leap. Through EIP, I built a functional AI voice agent, which I’m now continuing to develop alongside a professor from the Computer Science department. It was my first real immersion into startup building, and I wouldn’t trade it for anything.

What piece of advice would you give to someone currently going through the admissions process and considering an MBA from Booth?

The admissions process is long, but absolutely worth it. Booth gives you the time and freedom to explore career paths you might never have considered otherwise. The professors, academics, and students constantly push you to be your best, no matter the domain. You’ll meet people chasing wildly different goals, but all deeply committed to them, and can learn from every one of them.