Cliff Holekamp is Cofounder, Managing Director, and a General Partner of Cultivation Capital. His board service in the Cultivation portfolio currently includes Decide, Benchmark Email, Clever Real Estate, PlanGap, ScopeStack, and Parsec Education. Cliff has been recognized by Business Insider as one of the “Seed 100 Best Early Stage Investors” in the United States (2022) and as the top startup investor located in South Carolina (2026).
Cliff started his career in enterprise sales for IBM. Following graduate school, he was the Founder and President of Foot Healers (sold to private equity in 2007). Subsequently, he served as the Professor of Practice and Academic Director for Entrepreneurship at the Olin Business School at Washington University in St. Louis (retired in 2019) where he was named one of the Top 100 Entrepreneurship Professors in the World (2015) and where he led the entrepreneurship program to being ranked #1 in the world (Inc. Magazine, 2019).
His nonprofit board service currently includes work with the Clemson University Research Foundation, NextGEN, and the Holekamp Seed Fund and Skandalaris Center at Washington University in St. Louis. He is also on the Board of Trustees for Christ Church Episcopal School and for Washington & Lee University.
Cliff holds a BA from Washington and Lee University and an MBA from Washington University in St. Louis.
The background described above reflects this individual’s professional experience, including prior roles, outside activities, and involvement with Cultivation Capital portfolio companies. It does not represent the investment performance of any Cultivation Capital fund and should not be relied upon as an indication of future results.
