Ami Daniel, founder of maritime AI company Windward, returns to the pod with a front-row view of the Middle East energy shock — and a confession about the one big thing he got completely wrong about AI.
With US naval pressure tightening around Iranian ports and ships going dark in the Strait of Hormuz, Ami explains why this energy crisis has no quick fix: 20% of the world’s oil and gas cannot simply be rerouted. He maps the geopolitical reshaping of the Middle East, why Israeli and UAE capital markets are telling a different story to the headlines, and why the Abraham Accord alliance may become the defining axis of the region for the next two decades.
Then the conversation shifts to AI and investing. Ami’s big admission: he thought data would be commoditised and insight would be scarce. He had it exactly backwards. Insight is now effectively free — you can get PhD-level analysis on an API. Data is the scarce resource. That one inversion is eating the entire SaaS industry alive.
But Ami argues the SaaS collapse is a buying opportunity for patient investors — if you know what to look for. Proprietary data moats. High average order values. Strong net revenue retention. And it’s also a good idea to look for wartime CEOs who have navigated real adversity before the good times arrived.
We also get into Windward’s own journey — why leaving the London Stock Exchange wasn’t a vote against the UK market, why he’s now backing a company to list there, and what it means to steer a business through years of people thinking you’re wrong.
Five takeaways:
Brought to you by Progressive Equity.
Links mentioned in this episode:
Windward insights: https://insights.windward.ai
Ami Daniel on LinkedIn: https://www.linkedin.com/in/amidaniel
Windward on X: @WindwardAI
Ami Daniel on X: @AmidanielOne
Orlando Bravo / Thoma Bravo—software is a buying opportunity (CNBC): https://www.cnbc.com/2026/02/11/tech-investor-orlando-bravo-software-ai.html
Ben Horowitz — Peacetime CEO / Wartime CEO: https://a16z.com/peacetime-ceo-wartime-ceo/
Previous episode with Ami (September 2024): https://substack.com/@jeremymckeown/p-148564789
HyperNormal Times: https://jeremymckeown.substack.com
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