Winklevoss is a former adjunct professor of insurance at the Wharton School of the University of Pennsylvania. He is a graduate of Grove City College and received a PhD in mathematics from the University of Oregon. He has written more than 20 books, including Pension Mathematics with Numerical Illustrations. He is also the founder of Winklevoss Consultants and Winklevoss Technologies.
- Pension Mathematics with Numerical Illustrations (1977, 2d ed. 1993)
- Public Pension Plans: Standards of Design, Funding, and Reporting (1979, with Dan McGill)
- Munn, Russell (January 1990). "Chamber Opposes Early Retirement Bills". South Carolina Business Journal. Retrieved July 6, 2011. (subscription required)
- "About Us". Winklevoss Technologies. Retrieved July 6, 2011.
- Rosenblatt, Joel (January 11, 2011). "Facebook Seeks Finality in 'Social Network' ConnectU Court Fight". Bloomberg Businessweek. Retrieved July 6, 2011.