In 1981 Fluegelman was the owner and sole employee of The Headlands Press, a small book publisher in Tiburon, California. He had attended an early computer expo in San Francisco in the late 1970s, and after agreeing to publish and coauthor Writing in the Computer Age decided to purchase his first computer. In October Fluegelman received one of the first IBM PCs sold in San Francisco, and in two weeks began to write his own accounting program in IBM BASIC.
In late 1982 Fluegelman developed PC-Talk, a very popular and successful communications software. He marketed it under a system he called "Freeware", which he characterized as "an experiment in economics more than altruism". Freeware was licensed under terms that encouraged users to make voluntary payments for the software, and it allowed users to copy and redistribute the software freely as long as the license terms and text were not altered. He collaborated with PC-File (database software) developer Jim Knopf to adopt similar names (PC-File was originally "Easy-File"), and prices, for their initial shareware offerings; they also agreed to mention each other's products in their program's documentation.
Fluegelman was admitted to The State Bar of California in January 1971.
Fluegelman edited PC World magazine from its introduction in 1982 until 1985, and Macworld magazine from its introduction in 1984 until 1985.
In 1985, Fluegelman, already suffering from colitis, was diagnosed with cancer. On the afternoon of July 6, 1985, he left his office in Tiburon, California. A week later, his abandoned car was found at the north end of the Golden Gate Bridge near San Francisco. His family held a memorial service for Fluegelman, and he is presumed dead, though his body has never been found. Kevin Strehlo, then an InfoWorld columnist, submitted a memorial column which mentioned that "friends say a suicide note was found inside" his car. InfoWorld rejected this column, but an online news service published it.
The Headlands Press produced books and negotiated publishing contracts for them with major publishers. Many of the books were designed by Howard Jacobsen and produced by his company, Community Type and Design. This list is arranged by year of book publication:The New Games Book
Edited by Andrew Fluegelman and Shoshana Tembeck. A Headlands Press Book, Dolphin/Doubleday (1976). ISBN 0-385-12516-XA Traveler's Guide to El Dorado & the Inca Empire
By Meisch, Lynn. A Headlands Press Book. Publisher: Penguin Books New York (1977). ISBN 0-14-046280-5Familiar Subjects: Polaroid SX-70 Impressions
By Norman Locks. A Headlands Press Book. HARPER & ROW, PUBLISHERS, San Francisco (1978). ISBN 0-06-250530-0How to Make and Sell Your Own Record
By Diane Sward Rapaport. A Headlands Press Book. Putnam, Prentice-Hall (1979). ISBN 0-8256-9932-0How to watch a football game
By Frank Barrett; Lynn Barrett. Publisher: New York : Holt, Rinehart, and Winston (1980). ISBN 0-03-056958-3Worksteads: Living and Working in the Same Place
By Jeremy Joan Hewes. The Headlands Press, Inc., San Francisco. Doubleday (1981). ISBN 0-385-15995-1More New Games
By The New Games Foundation. Main Street Books New York: Dolphin Books/Doubleday & Company (1981). ISBN 0-385-17514-0SUSHI
By Mia Detrick, Illustrated by Kathryn Kleinman A Headlands Press Book. Chronicle Books LLC (1983) ISBN 0-87701-238-5
Books co-authoredWriting in the Computer Age: Word Processing Skills and Style for Every Writer
By Andrew Fluegelman and Jeremy Joan Hewes. Anchor Press/Doubleday Publishing Group (1983) ISBN 0-385-18125-6Mime: A Playbook of Silent Fantasy
By Kay Hamblin. The Doubleday Publishing Group (1978) ISBN 0-385-14246-3