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Bob Mason | AI is a Tidal Wave

2026-10-02

He gave his personal life savings to the company to make payroll. There were about forty people left and the cash had run out.

That company was Art Technology Group. It went public in 1999 and Oracle bought it in 2011.

In this episode of CTO Confidential, Mike Rispoli sits down with Bob Mason, cofounder and managing partner of Argon Ventures. Before investing, he went zero to IPO twice as a founder and CTO, first at ATG and then at Brightcove.

Two engineers who lived through the web transition comparing it to the one happening now.

We get into:

  • The innovator's dilemma, and running the old business while betting on the new one
  • Why he puts NFTs, the metaverse, and meme coins in a different category than this
  • Jevons paradox, and why cheap intelligence expands the market instead of killing it
  • Computer vision inspecting every inch of parachute webbing
  • LiDAR scanning entire streetscapes into a digital twin for municipal budgets
  • Why agentic tooling may finally deliver what Agile actually promised
  • Fixed bid software, and the entrepreneurs that were never able to say yes before
  • Whether a bubble and a genuine transformation can both be true at once
  • Daily urgency and strategic patience, and why founders always think it is almost easy

Connect with Bob:
LinkedIn: https://www.linkedin.com/in/robertmason/
Argon Ventures: https://argon.vc

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