He received his bachelor's and master's degrees at the University of Virginia, where his studies focused on English and American literature.
and a doctorate at the University of Michigan, Ann Arbor, where he won a Hopwood Writing Award and the Brubacher Prize in the History of Education.
He has been a Visiting Fellow at Johns Hopkins University's Paul H. Nitze School of Advanced International Studies, and at the American Enterprise Institute; an Ella Baker Fellow at Antioch New England Graduate School; a consultant to the John Templeton Foundation; and from 2001 to 2004 a staff member at the American Academy for Liberal Education, where he created new K-12 programs.
Amid controversy, the Shimer College Board of Trustees announced in January 2006 that at his urging it had accepted an invitation to move the school to the Illinois Institute of Technology campus on the south side of Chicago.
He collaborated with Mark Bauerlein in editing the republication of John Andrew Rice's suppressed autobiography, I Came Out of the Eighteenth Century (1942), in the Southern Classics Series of the University of South Carolina Press (2014).