Entrepreneur |Real Estate Developer| Strategist

Helping entrepreneurs and business leaders create a legacy through real estate, strategy, and leadership. 

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His personal investment strategy was to find asymmetric risk versus reward, therefore, finding disproportionate up-side versus downside in business strategy and investments. Therefore, he worked for a Fortune 400 automotive defense contractor as a Systems Engineering Manager while simultaneously growing his real estate business and investments. Later, he continued to grow his career as a systems engineering consultant in the defense and aerospace working with high profile defense contracts on dozens of complex weapon systems.

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Aaron (A.J.) Armstrong is a real estate developer, engineer, and serial entrepreneur. He is a former D1 football player and graduate from the United States Military Academy at West Point with a BS in Systems Engineering. He and his wife are the owners and founders of Armstrong Ventures LLC, Armstrong Real Estate Group LLC, and Marissa’s Fit Boutique LLC. He has a business graduate certificate from Northeastern University, and an MBA from University of Wisconsin – Oshkosh with a concentration in finance.

Meanwhile, he launched Armstrong Ventures, a Consulting & Equity service offering real estate and business solutions. The most recent business is “The Venture Project” a 7,500 sf coworking space and business incubator. His current asset portfolio is estimated above $2.5MM AUM placing his net worth above $1MM at the age of 30 years old. He is also the host of “Winners, Wallets and World Views” a podcast featuring expert lead discussions on tips and tactics for business leaders.


  • Bachelor of Science - United States Military Academy at West Point, NY - Systems Engineering

  • Graduate Certificate - Northeastern University at Boston, MA - Business  Administration

  • Masters of Business Administration - University of Wisconsin at Oshkosh, WI  - Finance

Professional Credentials

  • Certified Systems Engineering Professional - INCOSE

  • INCOSE Member

  • 200,000+ Listens on Podcast Winners, Wallets & Worldviews

  • Lectured or spoken to over 100 companies, universities or conferences including United States Military Academy at West Point, University of Wisconsin, & INC

  • Owner of Armstrong Ventures with over $2.5MM+ AUM

  • Former Division 1 athlete and Army football letter winner

  • Consulted with 50+ small to large companies, including Aerospace & Defense contractors, and Fortune 500 brands

  • Wrote the technical proposal for new fleet of USPS vehicles winning over 6 Billion dollars of business

  • 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

  • Licensed real estate salesperson specializing in commercial real estate. 

Community involvement & volunteering

  • Board Member of Business Improvement District Oshkosh - 2019-Present

  • Board Member of Oshkosh Chamber Economic Development Advisory Council

  • Chairmen of the Board University of Wisconsin System - WiSys VentureHome Oshkosh 

  • Member of Amplify Oshkosh Consortium

  • Member of the Oshkosh Chamber of Commerce - 2017-Present

  • Worship team member at Community Church Oshkosh - 2020-Present

  • Member of Community Church Oshkosh - 2020-Present

  • Men's Ministry Steering Committee Member Community Church Oshkosh - 2021-Present

  • Board Member of STOIC Garage non-profit Auto Services - 2020-2021