[1] O'Shaughnessy's areas of expertise include quantitative equity analysis, portfolio management, research decisions, and investment models.

He has authored several books that use Standard & Poor's Compustat database to provide extensive quantitative analysis of stock market performance.

During this time, his interest in quantitative research was recognized by a colleague who was on the board of directors with O'Shaughnessy at the St. Paul Chamber Orchestra.

[2] In 1999, O'Shaughnessy started Netfolio, The Personal Fund Company, to offer individual investors the ability to build their own diversified portfolio over the internet.

[10] In addition to its flagship investment into Stability Ai, O'Shaughnessy Ventures' other key investments include Positive Sum, Chaotic Capital, Permanent Equity,  Anchorless Bangladesh, Prefect, Synthesis School, Eighty-Seven Capital, Entrepreneur First, and Ladder.

O'Shaughnessy is the former chairman of the board for the Chamber Music Society of Lincoln Center and currently serves as the chair of the capital campaign for CMS.