In 2004, Kaufmann co-founded (with Mark Bernstein) Hundreds of Heads Books to publish a series of books that help people through life’s biggest challenges, based on advice and entertaining experiences collected from hundreds of people across the US who have "been there, done that". Their best-selling book "How to Survive Your Freshman Year" is in its 5th edition. Kaufmann has written op-ed articles about his professional activities, especially relating to the role Israel can play in promoting Palestinian private sector technology-related enterprise. In 2017, he wrote a feature article in Foreign Affairs entitled, “Start-Up Palestine: How to Spark a West Bank Tech Boom.” He has also published articles in the Times of Israel  and Haaretz. When studying a J.D. at Harvard Law School, Kaufmann was an editor of the Harvard Law Review. He has spoken at forums including TEDx Rome, StartupGrind Ramallah, Seeds of Peace, American Israel Public Affairs Committee (AIPAC) and DLD Tel Aviv.