She has worked with CNN, NPR, Bloomberg TV, Yahoo News, ABC and the BBC.

O'Leary graduated cum laude from Williams College with degrees in English and Art History.

[3] O'Leary began her career with ABC as a member of a team including Diane Sawyer, Charles Gibson, and Peter Jennings, which won a Peabody Award for reporting on the September 11th terrorist attacks.

[1][4] She worked for NPR from 2003 to 2006, before moving to Bloomberg TV, where she covered politics and economic policy.

[7][8] O'Leary suffered most of her life from symptoms of endometriosis, which she was eventually diagnosed with at the age of 37.