[8] Weiss attended Yale College and received his MBA at Harvard Business School, where he was a Baker Scholar and a Loeb Fellow in Finance.

From 2001 to 2009, Weiss was based in Paris, France where he served as a vice chairman of European investment banking, and subsequently global head of mergers and acquisitions.

[15] Weiss testified before both chambers of Congress to explain PROMESA and the Obama Administration's plan to address the Puerto Rican debt crisis.

[16] The law was criticized on the right by fiscal conservatives unhappy with the possible cost to U.S. taxpayers and on the left by advocates for workers and for Puerto Rican autonomy, but was heralded as "the only piece of major economic policy to pass Congress" to date in 2016.

[21] Weiss co-authored the December, 2012 Center for American Progress report, “Reforming Our Tax System, Reducing Our Deficit,” which recommended a more progressive tax regime and a balanced approach to long-term debt reduction and the May 2017 Peterson Institute report, “The Financial Stability Oversight Council: An Essential Role for the Evolving U.S. Financial System”, which discussed the importance of the Council in the face of pressure to limit its authorities.