AARON J. ARMSTRONG
Entrepreneur |Real Estate Developer| Strategist
A trusted business advisor for entrepreneurs, investors, and executives.
Offering technical expertise in marketing strategy, real estate, and emerging ventures.





His time at West Point honed his strategic thinking and resilience, qualities that continue to define his approach to business and life. Commissioned as a U.S. Army officer, Aaron served with distinction, overseeing operations for the cutting-edge PATRIOT missile system, one of the military’s most advanced air defense platforms. After an honorable and medical discharge, he transitioned to civilian life, channeling his strategic acumen into entrepreneurship. Aaron built a successful real estate portfolio through multifamily investments using the BRRR (Buy, Rehab,

Aaron J. Armstrong is a distinguished business consultant, author, strategist, systems engineer, and entrepreneurship expert whose remarkable career blends military discipline, entrepreneurial innovation, and faith-driven leadership. A 2015 graduate of the United States Military Academy at West Point with a Bachelor of Science in Systems Engineering, Aaron earned a full football scholarship as Wisconsin’s number-one ranked fullback in 2010, showcasing his athletic prowess as an Army football letter winner.
Rent, Refinance) method, creating passive income streams and laying the foundation for his business ventures. As the founder and host of the acclaimed podcast Winners, Wallets, and Worldviews, Aaron has interviewed elite performers, including General David Petraeus, U.S. Senator Ron Johnson, billionaires, entrepreneurs, NFL players, and industry pioneers like T.J. Rodgers (Cypress Semiconductor), Jim Vandehei (Co-founder of Politico & Axios), & Culver’s founder, Craig Culver offering listeners actionable insights into business, leadership, and purposeful living.
A devoted husband to Marissa Armstrong, a fitness specialist and entrepreneur, and proud father of three children, Aaron’s commitment to faith and family anchors his life’s work. While previously residing in Oshkosh, Wisconsin, he co-founded The Venture Project, a coworking space and business incubator that empowered local entrepreneurs to launch and scale their ventures. He also served as a board member of the Oshkosh Chamber of Commerce and as an overseer/elder at Community Church, driving economic and spiritual growth in the region. Aaron co-founded the Vetrepreneur Program, a multi-state business accelerator and pitch contest that equips veteran entrepreneurs with mentorship, resources, and funding to turn their visions into reality.
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Now residing in Florida, Aaron serves on the Worship Team and as a guest speaker at Deep Creek Community Church, where he inspires congregants with messages of faith, purpose, and perseverance. An accomplished speaker, he has delivered keynote addresses and workshops at over 100 churches, businesses, universities, and conferences across the country, sharing stages with thought leaders and appearing as a guest on dozens of podcasts. His book, The Holy Hustle: Faith, Family, Fortune, is a powerful manifesto for ambitious individuals, blending biblical principles with practical strategies for success in business and life. Aaron earned an MBA from the University of Wisconsin Oshkosh, where he was honored as the 2024 Outstanding Alumni by the School of Business for his contributions to entrepreneurship and leadership.
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Currently, Aaron serves as a systems engineering manager at Lockheed Martin, where he oversees the development, integration, and sustainment of some of the world’s most advanced weapon systems, applying his technical expertise to national security. His unique combination of military precision, entrepreneurial vision, and faith-driven purpose makes him a trusted consultant, empowering organizations and individuals to achieve transformative growth and lasting impact.
Education
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Bachelor of Science - United States Military Academy at West Point, NY - Systems Engineering
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Graduate Certificate - Northeastern University at Boston, MA - Business Administration
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Masters of Business Administration - University of Wisconsin at Oshkosh, WI - Finance
Professional Credentials
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Certified Systems Engineering Professional - INCOSE
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INCOSE Member
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500,000+ Listens on Podcast Winners, Wallets & Worldviews
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Lectured or spoken to over 100 companies, universities or conferences including United States Military Academy at West Point, University of Wisconsin, & INC
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Owner of Armstrong Ventures with over $2.5MM+ AUM
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Former Division 1 athlete and Army football letter winner
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Consulted with 50+ small to large companies, including Aerospace & Defense contractors, and Fortune 500 brands
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Wrote the technical proposal for new fleet of USPS vehicles winning over 6 Billion dollars of business
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Wrote engineering requirements for various DoD prototypes including aerospace C5ISR products, hyperspectral imagery designs, electric and non-electric ground vehicles, marine vessels, and advanced robotics
Community involvement & volunteering
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​Worship team member, guest speaker, and member of Deep Creek Community Church 2023- Present
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Board Member of the Oshkosh Chamber of Commerce - 2022-Present
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Overseer/Elder and Board Member of Community Church Oshkosh 2022-2024
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Board Member of Business Improvement District Oshkosh - 2019-2024
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Board Member of Oshkosh Chamber Economic Development Advisory Council - 2022-Present
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Chairmen of the Board University of Wisconsin System - WiSys VentureHome Oshkosh - 2020-Present
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Member of Amplify Oshkosh Consortium 2022-Present
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Member of the Oshkosh Chamber of Commerce - 2017-Present
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Worship team member at Community Church Oshkosh - 2020-2025
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Member of Community Church Oshkosh - 2020-2025
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Men's Ministry Steering Committee Member Community Church Oshkosh - 2021-2023
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Board Member of STOIC Garage non-profit Auto Services - 2020-2021