Better Offline

Working In The Dot Com Bubble ft. Matt Rosoff

41 snips
Jan 26, 2026
Matt Rosoff, longtime tech journalist and editor-at-large at The Register, recalls life inside 90s web startups and CNET’s rapid rise. He tells stories of early product misses, the cultural excesses that hinted at a bubble, and comparisons between dot-com burn and today’s AI hype. Conversations touch on telecom excess, retail trading mania, and why many premature ideas later succeeded.
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ANECDOTE

From Early Web Rookie To CNET Insider

  • Matt Rosoff joined CNET in 1995 as employee number 42 and launched its first email newsletter, Digital Dispatch.
  • He watched the company grow to 500+ staff and go public during the dot-com boom.
ANECDOTE

The Startup With No Content System

  • Matt describes a 2000 startup that had no CMS, used Visual Source Safe, and was incompetently run despite ample funding.
  • He left quickly and found steadier work, noting many dot-com firms were 'hot air.'
INSIGHT

Failure Often Came From No Business, Not No Idea

  • Many dot-com failures lacked customers, revenue, or realistic unit economics rather than tech promise.
  • Rosoff cites Pets.com and Cosmo.com as early ideas that later found viable second attempts.
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