[2][self-published source] Winer is noted for his contributions to outliners, scripting, content management, and web services, as well as blogging and podcasting.

He is the founder of the software companies Living Videotext, Userland Software and Small Picture Inc., a former contributing editor for the Web magazine HotWired, the author of the Scripting News[3] weblog, a former research fellow at Harvard Law School, and current visiting scholar at New York University's Arthur L. Carter Journalism Institute.

[12] Ready, a RAM resident outliner for the IBM PC released in 1985, was commercially successful but soon succumbed to the competing Sidekick product by Borland.

[15] In 1987, at the height of the company's success, Winer sold Living Videotext to Symantec[16] for an undisclosed but substantial transfer of stock[17] that "made his fortune.

"[18] Winer continued to work at Symantec's Living Videotext division, but after six months he left the company in pursuit of other challenges.

Frontier was an outliner-based scripting language, echoing Winer's longstanding interest in outliners and anticipating code-folding editors of the late 1990s.

[30] With products and services based on UserLand's Frontier system, Winer became a leader in blogging tools from 1999 onward,[31] as well as a "leading evangelist of weblogs.

[33] In June 2002 Winer underwent life-saving bypass surgery[34] to prevent a heart attack and as a consequence stepped down as CEO of UserLand shortly after.

"[36] Winer started DaveNet,[37] "a stream-of-consciousness newsletter distributed by e-mail"[38] in November 1994[39] and maintained Web archives of the "goofy and informative"[40] 800-word essays since January 1995,[41] which earned him a Cool Site of the Day award in March 1995.

[42] From the start, the "Internet newsletter"[43] DaveNet was widely read among industry leaders and analysts,[44] who experienced it as a "real community.

"[50] Scripting News started as "a home for links, offhand observations, and ephemera"[19]: 59  and allowed Winer to mix "his roles as a widely read pundit and an ambitious entrepreneur.

"[19]: 50  Offering an "as-it-happened portrait of the work of writing software for the Web in the 1990s,"[19]: 59  the site became an "established must-read for industry insiders.

Winer spent one year as a resident fellow at the Harvard Law School's Berkman Center for Internet & Society, where he worked on using weblogs in education.

[64] In February 1996, while working as a columnist for HotWired, Winer organized 24 Hours of Democracy, an online protest against the recently passed Communications Decency Act.

As part of the protest, over 1,000 people, among them Microsoft chairman Bill Gates, posted essays to the Web on the subject of democracy, civil liberty and freedom of speech.

[79] Winer's weblogging product, Radio Userland, the program favored by Curry, had a built-in aggregator and thus provided both the "send" and "receive" components of what was then called audioblogging.

[85] Winer also has an occasional podcast, Morning Coffee Notes,[86] which has featured guests such as Doc Searls, Mike Kowalchik, Jason Calacanis, Steve Gillmor, Peter Rojas, Cecile Andrews, Adam Curry, Betsy Devine and others.

BloggerCon I (October 2003) and II (April 2004), were organized by Dave Winer and friends at Harvard Law School's Berkman Center for the Internet and Society in Cambridge, Mass.