Why Companies Aren't Getting ROI on AI (with Brenn Hill)

Everyone's spending big on AI coding tools — but is anyone actually measuring if it's working?

In this episode, we're joined by Brenn Hill, a Berlin-based engineering leader and author of "The Delivery Gap," to break down the AI ROI myth: why token-based pricing is nearly useless for real business planning, why companies like Uber and Microsoft have pulled back on major AI investments, and the three-part framework (cost, verification, intent clarity) Brenn uses to actually measure whether AI is paying off.

We also talk about:

• Why AI gets you "80% of the way there" — and why that's not the same as production-ready
• Machine catch rate vs. change failure rate, and why they matter more than token counts
• Why tokens can't be compared across AI providers or even across tasks
• What it's like navigating Berlin's housing crisis as an American expat
• Entrepreneurial culture differences between the US, Vietnam, and Australia

Brenn's book, "The Delivery Gap," lays out the research behind what's actually working (and mostly not) in AI-assisted software delivery — plus practical roadmaps for engineering leaders and individual contributors navigating this shift.

📖 Get the book: "The Delivery Gap" — available on Amazon

🔗 Connect with Brenn Hill on LinkedIn

🎥 Watch on YouTube

If you enjoyed this conversation, subscribe for more casual, honest conversations at the intersection of tech, careers, and the future of work.

Timestamps:

• 00:00 – Intro & catching up with Brenn in Berlin
• 08:00 – The AI ROI myth
• 12:00 – Why tokens are a useless cost metric
• 17:00 – The cost/verification/intent-clarity framework
• 24:00 – Machine catch rate & change failure rate
• 52:00 – About "The Delivery Gap" and where to find it