He cofounded the Washington, D.C., investment firm Friedman, Billings, Ramsey Group in 1989, where he served as president, secretary and co-CEO through 2001.

[5] Ramsey received a baseball scholarship[2] and became senior-year team captain and MVP[6] of the George Washington Colonials.

[9] Following his time there, he joined brokerage firm Johnston, Lemon & Co.'s sales and trading group in 1986,[8] and became a vice president of the company.

[21] The GWP was formed as an initiative to boost the region's economy by addressing issues of transportation, human capital, innovation, and entrepreneurship through collaboration among the area's largest employers.

[22] With the launch of the Capital CoLAB in June 2018, the Partnership expanded to include leaders from academic institutions in order to focus on talent and innovation initiatives.

[5][26] During his tenure on the board, Ramsey chaired the committee that lead to Steven Knapp's hiring as the 16th president of George Washington University.

[5] Additionally, in 2005, the Ramsey family donated $1 million to the university to create an investment portfolio to be run by Master of Business Administration students, so that they could build real world finance expertise.

[27][28] In 2013, he was elected Chairman Emeritus of GWU Board of Trustees and was awarded the honorary degree of Doctor of Public Service in May 2014.

[26] Ramsey was selected in March 2014 as chairman and CEO of the nonprofit Washington 2024, founded to run the city's effort to host the games.

Following the announcement, Ramsey released a statement that he would continue working with leaders in the D.C. area to develop opportunities for young people in sport.