Richard Stroupe
About Richard Stroupe
Richard Stroupe is the founder and managing partner of Cape Fear Ventures, based in Wilmington, North Carolina. PitchBook lists a BS in Computer Information Systems from Appalachian State University (1998). His Blu Venture Investors profile adds an MS from The George Washington University.
Before investing full time he built companies in national security and enterprise technology. He founded TRS Consulting, which NCI Information Systems acquired in July 2009. He then co-founded Sequoia Holdings, a provider of engineering and analytic solutions to the national security sector, where he is Vice Chairman. He also served as Senior Vice President and General Manager of the National Security Group at Empower AI.
He taught part time at George Washington University and was entrepreneur-in-residence at Georgetown University. He hosts a podcast, The Amplified CEO.
Crunchbase and Blu Venture Investors show him investing since at least 2011. He joined Blu Venture Investors that year, is now a partner emeritus there, and has also been managing partner of TAOS Capital since 2017. His personal site describes him as an operator-led venture capitalist. Today he invests through Cape Fear Ventures and affiliated vehicles.
PitchBook lists him as an individual angel with two recorded investments. Public records show only part of his activity, so treat that count as a floor.
Skillmaker is an AI and XR workforce training platform in Wilmington. Cape Fear Ventures took part in its earlier $2.5M pre-seed round. Skillmaker then announced an oversubscribed $4.5M seed round, which names Stroupe among existing backers doubling down. PitchBook records the seed as dated 11 June 2026 and lists him as a Skillmaker board member.
He is also Chairman of Ohanafy, which sells software to beverage distributors. Crunchbase shows Cape Fear Ventures as lead investor in Ohanafy's seed round. A Wilmington entrepreneur network says he has doubled down on both Ohanafy and Skillmaker.
His personal site lists experience in AI and data infrastructure, national security and defense, aerospace, and enterprise technology. It says he works alongside founders on operating systems, capital strategy, and scaling. Cape Fear Ventures describes a focus on operational performance and growth.
He has attracted other North Carolina investors into his Wilmington portfolio companies. Check size and fund size are not public.
- Skillmaker: AI and XR workforce training platform in Wilmington, NC. Cape Fear Ventures joined the pre-seed, and he was among the backers of the $4.5M seed (2026-06).
- Ohanafy: software for beverage distribution. Cape Fear Ventures led the seed round, and he is Chairman. The year is not stated in the sources.
Investing activity
Richard Stroupe appears in 1 AI deal tracked by the Lounge deals desk. The rounds are mostly Seed, with a median round size of $5M. The most recent is Skillmaker (Seed, $4.5M, Jun 2026).
Richard Stroupe most often invests alongside Full Circle, Lee Provost, Lelon Winstead and Partners, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Richard Stroupe
Does Richard Stroupe invest in AI startups?
Yes. He has backed Skillmaker, an AI and XR workforce training company, and chairs Ohanafy, which sells software to beverage distributors. His site lists AI and data infrastructure among his areas of experience.
What is Richard Stroupe's typical check size?
No check size is public. Neither his site nor the PitchBook and Crunchbase profiles state one.
What stage does Richard Stroupe invest in?
Public records show seed and pre-seed participation, including Ohanafy's seed round and Skillmaker's pre-seed and seed rounds. TAOS Capital's Crunchbase profile lists seed and early-stage venture.
What fund is Richard Stroupe associated with?
He is founder and managing partner of Cape Fear Ventures in Wilmington, NC. He is also managing partner of TAOS Capital and a partner emeritus at Blu Venture Investors.
What companies has Richard Stroupe built?
He founded TRS Consulting, acquired by NCI Information Systems in 2009. He also co-founded Sequoia Holdings, a national security engineering and analytics firm.
Does Richard Stroupe invest outside North Carolina?
His recent AI deals are in Wilmington, NC. His site also cites exposure to space, defense, and national security technology, but it does not name a geographic limit.
Is Richard Stroupe an angel investor?
Yes. Richard Stroupe invests personally as an angel.
What AI companies has Richard Stroupe invested in?
Richard Stroupe's AI investments include Skillmaker. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
What stage does Richard Stroupe invest at?
In the rounds tracked on Lounge, Richard Stroupe has invested at Seed, with a median round of $5M.
Who does Richard Stroupe co-invest with?
Richard Stroupe's most frequent co-investors on Lounge are Full Circle (1 deal), Lee Provost (1 deal), Lelon Winstead (1 deal), Partners (1 deal) and Workshop Ventures (1 deal).