After graduating in 1968, he had a brief sojourn in the high-flying world of business, rising to a vice president's spot at then-hot/then-not National Student Marketing Corporation (about which he wrote The Funny Money Game, his first book to gain national attention).

Slightly older -- 23 -- and very slightly wiser, he entered Harvard Business School, writing magazine pieces for New York Magazine on the side, and then going to work full-time as a Contributing Editor upon graduation. For New York he covered the world of finance, and when New York was sold, he followed Clay Felker to Esquire. For several years he had a column in Time and since 1986 has appeared annually in Parade. His work has also appeared in such places as The New York Times Sunday Magazine, Money and Worth.

His books include three New York Times best-sellers.  His Managing Your Money software for a time dominated the personal finance category and has helped hundreds of thousands take control of their finances. (For his own finances, he still uses DOS version 12.)

His anti-smoking commercials have run throughout the former Soviet Union. 

His work on auto insurance reform led to the placement of three initiatives on the March 1996 California ballot. (Backers ranged from former Secretary of State George Shultz to former San Francisco councilwoman Roberta Achtenberg to Quicken co-creator Tom Proulx.)  The measures lost, but may have laid the groundwork for future reform.

He has appeared on such shows as Today, Tonight, Tomorrow, Good Morning America, Face the Nation, and the MacNeil-Lehrer Report.   With Jane Bryant Quinn, he co-hosted Beyond Wall Street, an eight-part 1997 PBS documentary.