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Imagine spending millions of dollars and months of preparation on a revolutionary e-commerce platform, only to launch to absolute crickets. In the inaugural episode of The Qualified Answer, host Simon Elisha takes us back to the dot-com boom to dissect a spectacular B2B reverse auction failure—and explains why the hard lessons learned then are repeating themselves in today's AI gold rush.

From navigating the "irrational exuberance" of tech bubbles to making calculated decisions under pressure, Simon lays the groundwork for what this podcast is all about: exercising good judgment, learning from the expensive mistakes of others, and understanding that every tech decision comes with a "yes, with an if, or a no, with a but."

Key Takeaways & Topics Covered:

The Dot-Com Disaster: The story of a highly funded, heavily hyped reverse auction platform that failed on day one because it fundamentally ignored customer needs.

The Gorilla Game in the AI Era: Breaking down Geoffrey Moore’s market dynamics (Gorillas, Chimps, and Monkeys) and how players like Anthropic, Google, and OpenAI are currently battling for the Gorilla spot.

Mastering the OODA Loop: How to apply the military concept of Observe, Orient, Decide, and Act to your business strategy—and why the "Orient" phase is the one AI can't do for you.

"Buy What's on the Truck": A hard-learned lesson in IT procurement. Why betting on tech futures and "coming soon" software can ruin your architecture.

The Power of Network Effects: How open standards and network effects win markets, featuring throwbacks to the fax machine, AWS S3 APIs, and the new push for Anthropic's Model Context Protocol (MCP).

Resources & Concepts Mentioned:

• Crossing the Chasm, Inside the Tornado, and The Gorilla Game by Geoffrey Moore
• The OODA Loop (John Boyd)
• Model Context Protocol (MCP)

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Every honest answer in technology comes with conditions.

The Qualified Answer is a decisions podcast for senior technology leaders - the ones who own the call, and the ones who execute it.

Each episode is either a decision case - a senior leader walks you through one real call they had to make, what they chose, what they traded away, and what they wish they'd known - or a solo deep dive into the mental models, frameworks, and patterns behind how consequential decisions actually get made.

Hosted by Simon Elisha - 35 years in enterprise technology, first AWS technical hire in Australia, 700+ podcast episodes, and decades of decisions (some great, some not-so great).

New episodes coming soon. Subscribe now.

Yes, with an if. No, with a but. Keep on building!