Ari’s Secret Fortune (500)
Episode Overview
Sean is mysteriously missing (global tour? Carmen Sandiego arc? Grain Gang business trip?), so Ian sits down with Ari for a behind-the-scenes look at Ari’s Fortune 500 AI advisement. What starts as “we need an AI strategy” quickly turns into something far more important: figuring out who owns AI and how to drive real outcomes.
Additionally, please stick around for a very important announcement after the interview.
Key Takeaways
- “We need an AI strategy” is often code for “we don’t know who owns anything.”
Ari’s biggest insight from the Fortune 500 engagement is that the ask wasn’t the actual need. The work really started when they got honest about ownership. Barring that, “AI strategy” is more like “AI vibes.”
- Ari calls it plainly: the slow part wasn’t implementing AI, it was actually the human questions: who signs the PO, who owns the workflow, who schedules the security review, and who’s accountable when all of this spans multiple teams.
- Your AI lab can’t ship outcomes if it doesn’t have business context. One of the most useful “aha” moments was that AI work living in an innovation lab without operational grounding doesn’t scale.
- To win the room, you have to talk about the negatives. Progress stalls until the skeptics are addressed honestly. Yes, AI can slow engineers down; yes, failures happen; yes, trust and governance suck the oxygen out of meetings. But naming those issues is how you get to adoption.
- AI changes who does the work. Cloud changed where compute lives, DevOps changed how we ship, and AI changes who does the work. That’s why measurement is harder and why this transformation hits every department.
FAQ
Q: What did the Fortune 500 actually need when they asked for an “AI strategy”?
A: They needed operational clarity: clear ownership (who decides, funds, governs), plus visibility into bottlenecks and where productivity is leaking. The engagement shifted from “cool AI ideas” to a real plan with an operating model that can keep finding opportunities over time.
Timestamp: 2:47–5:44, 4:48–5:44
Q: What surprised Ari most about how big companies struggle with AI?
A: The politics of ownership and cross-functional work. AI was stuck in an innovation lab, nobody owned cross-functional automation, and there was constant tension between “the business wants it yesterday” and “IT wants control and governance.” The biggest breakthrough came when everyone started aligning on outcomes.
Timestamp: 12:12–13:50, 16:55–17:27
Q: How can IT leaders tell the difference between a real AI partner and “AI theater”?
A: If the conversation never leaves the demo, you’re watching theater. Ari’s filter is outcomes: a real partner helps define success metrics, governance, and continuous improvement, and can explain how AI actually reduces work (or cycle time) across your tools and workflows.
Timestamp: 29:07–31:22, 32:32–33:31
