Sai Kumar

About Me

From defense operations to deep tech and venture conviction — building at the intersection of 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, Databases, and AI. Founded the UChicago chapter of the Claude Builder Club. Clubs: EVC, Armed Forces Group, South Asia Business Group.

United States Military Academy

BS Systems Engineering with Honors · Jul 2014 – May 2018

Academic GPA: 3.58; Dean's List eight semesters; Distinguished Cadet for 2 years; Published three international papers; Fundamentals of Engineering License; Powerlifting Club

Trajectory

Deep TechMar 2026 – May 2026
Palantir American Tech Fellow

Remote

Selected as a Palantir American Tech Fellow, working at the intersection of defense technology and national security.

American Tech FellowDefense technologyNational security
StartupJun 2025 – Mar 2026
Startup Founder — Renux

Chicago, IL

Identified a critical inefficiency in single-family renovation workflows by conducting 40+ stakeholder interviews. Built a Python-based AI voice agent to automate contractor outreach, synthesizing project data and web scraping contractor repositories.

AI voice agent MVP40+ stakeholder interviewsAutomated procurement
VC & Investing2019 – Present
Investor — Real Estate, VC, Angel

Chicago, IL

Real estate investor since 2019 with $1.65M in AUM and $250k in ARR. Investment Analyst at Listen Ventures, sourcing 30+ startups (pre-seed through Series A) and developing the firm's Consumer AI thesis. Angel investing in consumer AI and biotech.

$1.65M AUM, $250k ARR30+ startups sourcedConsumer AI investment thesis#1 New Airbnb Host in Georgia (2021)
Space Force EngineeringSep 2022 – Sep 2024
Lead Engineer, EWS Operational Capabilities — US Space Force

Los Angeles, CA

Led a cross-functional team of engineers, scientific researchers, budget analysts, and vendors to deliver next-gen weather satellite capabilities serving over 3 million global users. Facilitated launch of multiple demo satellites for iterative design improvement.

3M+ global users servedNext-gen satellite developmentDoD acquisition innovation
LOS ANGELES AIR FORCE BASE
Army AviationMay 2018 – Sep 2022
Aviation Officer — United States Army

Savannah, GA & Mihail Kogalniceanu Airbase, Romania

UH-60M Blackhawk Pilot-In-Command and Air Mission Commander. Deployed for Operation Atlantic Resolve, leading 64 soldiers and managing $9M in international logistics. Earned #1 ranking as Platoon Leader and pilot from a cohort of 20 Aviation Officers.

Pilot-In-Command (fastest in cohort)$9M international logistics#1 ranked Aviation Officer
UH-60M Blackhawk Slingload OperationBlackhawk PlatoonEB Promotion CeremonyFlight School Graduation
West PointJul 2014 – May 2018
BS Systems Engineering with Honors — United States Military Academy

West Point, NY

Graduated with honors in Systems Engineering. Academic GPA: 3.58. Dean's List eight semesters, Distinguished Cadet for 2 years. Published three international papers focused on optimization. Fundamentals of Engineering License.

Dean's List (8 semesters)Distinguished Cadet (2 years)3 international publicationsFE License
West Point GraduationWest Point Cadet HeadshotWest Point A-Day

Skills & Expertise

Investment AnalysisStartup EvaluationPythonSwiftReact/NextJSMilitary LeadershipAviationReal Estate InvestmentMarket ResearchSystems EngineeringProject ManagementMachine Learning

Languages

HindiSpanishTelugu

Additional Information

Investments & Achievements

· Real Estate: $1.65M AUM, $250k ARR

· 2021 #1 New Airbnb Host in Georgia; Superhost 5 years

· Angel Investing in consumer AI and biotech

· Founded UChicago Claude Builder Club

Certifications & Interests

· FAA Commercial Fixed & Rotary Wing w/Instruments

· UH-60M Blackhawk & UH-72A Lakota Pilot

· SERE-C (High Risk Survival School)

· Advanced Open Water Scuba Diving

· Machine Learning