Investopoly

Ep 396: The AI trade – what can we learn from the dot-com bubble?

Feb 17, 2026
A comparison between today’s AI investment frenzy and the dot-com bubble. A look at why picking long-term winners is so hard and why many top names may not survive. Why broad market exposure and rules-based indexing can capture AI’s gains without betting on single winners. Practical policy and tax discussions affecting investors, including potential changes to capital gains tax.
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INSIGHT

History Repeats In Technology Booms

  • The AI trade mirrors the dot-com era: tech will reshape industries but market winners are uncertain.
  • Stuart Wemyss warns that correct technology theses can still produce many long-term losers.
ANECDOTE

Firsthand Dot-Com Valuation Memories

  • Stuart recalls valuing dot-com companies at Deloitte and seeing valuations disconnect from reality.
  • He notes firms listed or received venture capital while being pre-revenue or idea-only.
INSIGHT

2000 Tech Giants Mostly Failed

  • Most top tech companies from 2000 lost huge market value over 25 years; Microsoft was a rare survivor.
  • Stuart lists Cisco, Intel, Nokia, AOL and Yahoo as prominent examples that declined dramatically.
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