Sai Kumar

About Me

From defense operations to deep tech and venture conviction — bridging service, engineering, and investment.

Education

University of Chicago

MBA & MS Computer Science (Joint Degree) · Sep 2024 – Jun 2026

MBA Concentration in Entrepreneurship; MPCS Coursework in Python, Networks, and Databases

United States Military Academy

BS Systems Engineering with Honors · Jul 2014 – May 2018

Dean's List eight semesters; Published three international papers; Powerlifting Team

Trajectory

VC & Investing2024 – Present
Investment Analyst — Listen Ventures

Chicago, IL

Sourced, analyzed, and presented recommendations for over 30 startup investments ranging from pre-seed through Series A. Conducted market research and created investment thesis reports on consumer AI.

30+ startup investments analyzedConsumer AI investment thesisLP coordination and fund management
Venture & Startups2024
Operations Intern (Skillbridge) — FlashCash

Orlando, FL

Rewrote existing React/NextJS website as iOS app in Swift using AI tools. Oversaw customer acquisition generating over $100k in annual revenue streams.

React to Swift conversion$100k+ revenue generationData analytics scaling
Space Force Engineering2022 – 2024
Lead Engineer, EWS Operational Capabilities — US Space Force

Los Angeles, CA

Led engineering team developing next-generation weather satellites, delivering global operational capabilities to millions of users.

3M+ global users servedNext-gen satellite developmentDoD acquisition innovation
Army Aviation2018 – 2022
Aviation Officer — United States Army

Savannah, GA & Romania

UH-60M Blackhawk Pilot-In-Command and Air Mission Commander. Managed $6M+ flying hour program and led 64 soldiers in deployed environment.

Pilot-In-Command qualification$6M+ program managementNATO operations in Europe

Skills & Expertise

Investment AnalysisStartup EvaluationPythonSwiftReact/NextJSMilitary LeadershipAviationReal Estate InvestmentMarket ResearchSystems EngineeringProject Management

Languages

HindiAdvanced Intermediate
SpanishAdvanced Intermediate
TeluguElementary (Verbal)

Additional Information

Investments & Achievements

· Real Estate Investor

· 2021 #1 New Airbnb Host in Georgia

· Angel Investing in consumer and biotech

Certifications & Interests

· FAA Commercial Fixed & Rotary Wing w/Instruments

· Advanced Open Water Scuba Diving

· Machine Learning & AI Research