Working In The Dot Com Bubble ft. Matt Rosoff

January 26, 2026

AI Summary

5 min read

🎙️ The Voices & The Context

The Format: Casual interview with host-led banter, diving into personal history and industry analysis.
The Key Players:
- Ed Zittron (Host): Tech skeptic and podcaster, probing with finance insights and modern parallels.
- Matt Rozoff (Guest): Editor-in-chief of The Register, a 325-year Silicon Valley veteran (jokingly a vampire), sharing firsthand dot-com tales.
The Vibe: Nostalgic fun mixed with skeptical education—light-hearted laughs at past hype, intense warnings on today's AI bubble.

🗝️ Key Themes & Topics

The episode nostalgically dissects the dot-com bubble through Matt's career, contrasts it with AI hype, and questions modern economic risks.

Topic 1: Dot-Com Bubble Beginnings & Excess: Matt recounts joining CNET in 1995 as employee #42, rapid growth, wild parties, and early web excitement amid naive optimism.
Topic 2: Startup Failures & Warning Signs: Stories of incompetent ventures like Cadido (no CMS despite funding) and flops like Pets.com, Cosmo.com, MyLackey.com—hot air with no revenue.
Topic 3: Telecom Bust & Broader Collapse: Circular deals in fiber optics (e.g., Sienna Networks, WorldCom), retail investor frenzy via eTrade/Yahoo chats, and the 2000-2001 peak-to-trough.
Topic 4: AI Parallels & Skepticism: Internet felt re

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What you'll learn

1 (00:00) **🎙️ Introduction: Matt Rozoff**
2 (03:34) **Matt's Early Dot-Com Career at CNET**
3 (05:07) **CNET Ownership and Peak Hype**
4 (07:03) **Microsoft Antitrust Case**
5 (08:23) **Seattle Move and Cadido Startup Debacle**
6 (10:08) **Early Signs of Bubble Burst**
7 (12:40) **Telecom and Fiber Boom Bust**

+ Full timestamped outline available in the app

Show Notes

To kick off this week’s Better Offline Dot Com Special, Ed Zitron is joined by The Register’s Matt Rosoff to talk about what it was like to be in the tech industry during the last time the markets got drunk on a major digital hype cycle.

Matt Rosoff: https://www.theregister.com/Author/Matt-Rosoff/

https://bsky.app/profile/did:plc:agrmux4phzmfvgyblvhxrbnh

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