Stein writes frequently on a variety of topics, including politics, investing, and economics. He writes a regular column in the conservative magazines The American Spectator and Newsmax. He has also written for numerous publications including The Wall Street Journal, The New York Times, New York Magazine, Penthouse, Los Angeles Magazine, and Barron's Magazine, where his discussion of the Michael Milken Drexel Burnham Lambert junk bond situation, as well as the ethical dimensions of management buyouts, attracted heavy US national attention in the 1980s and 1990s. He wrote a regular biweekly column for Yahoo! Finance online, with his last article dated August 7, 2009. His bestselling books (with investment advisor Phil DeMuth) include Yes, You Can Retire Comfortably, Can America Survive?, and Yes, You Can Time the Market. In 2009, he published a collection of essays, The Real Stars.  Stein was fired from his position as a Sunday Business columnist at The New York Times in August 2009, due to a policy prohibiting writers from performing product endorsements or advertising. Stein had recently become an advertising spokesman for credit information company Freescore.com, and according to a Times statement, had assumed there would be no conflict provided that he did not discuss credit scoring in general or FreeScore.com itself in his column. However, the publication felt that it would be inappropriate for him to write for them while he was involved in advertising, and terminated his contract. Writing in The Spectator, Stein states his belief that the real reasons for his firing were budget cuts at the Times, his criticism of President Obama, and pressure from those critical of Expelled, who "bamboozled some of the high pooh-bahs at the Times into thinking there was a conflict of interest".  Stein is currently an in-house journalist at Newsmax Magazine, a magazine by the conservative media group Newsmax Media.

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