Leaving the First Boston Corporation as a Vice-President, Kaufman joined Gordian Group LLC, an investment bank specializing in distressed and/or complex financial challenges.

Finance discussing the future and whether more companies will file for Chapter 11,[17] Healthcare Bailouts and Hertz Trying to Sell Equity,[18] the COVID-19 government bailout,[19] Bloomberg TV, CNBC,[20][21] CNN (including Anderson Cooper 360), Fox Business with Maria Bartiromo,[22][23][24][25][26][27][28][excessive citations] Fox Business,[29][30][31][32][33][excessive citations] NBC (Today Show) and WSJ TV, on matters relating to insolvency, corporate reorganization, federal "bailout" issues and broader stimulus and economic issues, including General Motors (GM),[34][35] Chrysler and British Petroleum (BP),[36][37] American Airlines[38] & Hostess Brands,[39][40] as well as municipal and state insolvency issues.

[43] He is often cited in leading publications and international news sources such as The New York Times,[44] The Wall Street Journal[45] and Reuters,[46] and was the subject of a Bloomberg feature.

[citation needed] Kaufman's investment banking practice primarily encompasses advising Boards of Directors, private equity firms, and buyers and sellers of distressed, stressed or "story" situations.

[55][56] In 2014, the University of Virginia awarded him an honorary appointment as a Visiting Executive Lecturer at the Darden Graduate School of Business Administration.