We invest in entrepreneurs solving tomorrow’s hardest problems, bringing them capital, cutting-edge technology strategies, operational expertise, and mentorship to accelerate their impact.
Our goal is to help teams move faster, make better decisions, and build durable companies with lasting impact.
Our portfolio concentrates on early-stage companies in five high-conviction sectors: enterprise software that drives digital transformation, data science and AI that power intelligent systems, defense technologies critical to national security, and space industry ventures commercializing the final frontier.
Our Team
Managing Partner, Cape Fear Ventures
Lead Instructor, Elevate CEO Retreat
Richard Stroupe is a serial entrepreneur, seasoned investor, and leading technologist with a proven track record of turning innovative ideas into thriving, scalable companies. Over the past two decades, he has founded, built, and successfully exited multiple ventures across technology, defense, and real estate, each time honing the operational discipline, strategic insight, and leadership skills that now define his approach to business. Driven by a mission to empower the next generation of groundbreaking startups, Richard provides hands-on mentorship to founders, guiding them through the complex and often unpredictable challenges of early-stage growth.
As Founder and Managing Partner of Cape Fear Ventures, Richard invests in and builds high-potential businesses that combine operational excellence with strategic growth. Under his leadership, the firm has become known for its ability to identify promising ventures early, provide deep operational support, and position companies for long-term value creation.
Beyond his role as an investor, Richard is deeply committed to leadership development and entrepreneurial education. He has served as a Part-Time Faculty Member at George Washington University and as an Entrepreneur-in-Residence at Georgetown University, where he mentored students, alumni, and emerging founders on how to scale ventures and lead with purpose. Richard is also the creator of the Elevate CEO Retreat, a transformational program for growth-stage founders, and host of The Amplified CEO Podcast, where he shares actionable insights from top leaders and operators.
Director
Matt Gittleman is an early-stage venture investor and startup operator with a sharp eye for founders building defensible businesses in complex markets. Before moving to the investment side, Matt spent five years as an operator at venture-backed startups including LivingSocial, Yesware, and Catalant Technologies, where he developed a ground-level understanding of the challenges founders face in scaling operations, acquiring customers, and building repeatable growth engines.
As a Director at Cape Fear Ventures, Matt leads deal sourcing, due diligence, and portfolio management alongside founder Richard Stroupe. His investment thesis centers on data moats, dual-use technology, and regulated markets, and he brings over a decade of experience backing ambitious teams from pre-seed through Series A, with prior investment roles at Blu Ventures and Core Capital Partners.
Matt also serves as a Director at JHH vc, a Washington, DC-based family office venture fund focused on early-stage companies, and is a founding partner of VC in DC, the Mid-Atlantic’s largest institutional investor community, connecting more than 700 investors across 400+ funds. Through VC in DC, Matt has played a central role in growing the region’s venture ecosystem, building the connective tissue between founders, investors, and institutions that drives long-term startup success. Matt holds an MBA from Georgetown University’s McDonough School of Business and is based in the Washington, DC area.
Let’s talk!
Our mission is to bolster the crucial undertakings of emerging enterprises, operating with a transparent and accessible investment strategy. We understand what it takes because we have deep domain experience in building, managing, and executing successful outcomes.