In this episode of Project Gamma, Warner Moore sits down with Robb Winkle, technologist and Co-Founder & CTO of Doohickey AI, to explore what happens when the abstractions meant to simplify software start getting in the way.

Robb shares his journey from enterprise consulting to running a services business, then building a venture-backed product, and ultimately deciding to shut it down. Along the way, he breaks down four major pivots, the decision to raise outside capital, and the realities of being “profitable but stuck.”

We discuss:

-> Why services often surface product-market fit faster than product alone

-> How pivots signal abstraction failures, not founder mistakes

-> What “language is the best abstraction” really means in practice

-> How agentic coding and rapid feedback loops change how teams build software

-> Why removing layers like OpenAPI specs and workflow schemas can unlock speed and clarity

Robb also explains how modern AI makes it possible to move directly from business intent to working code, and what that shift means for teams building complex, integrated systems.

Whether you’re a founder, engineer, product leader, or security professional, this episode offers a grounded look at systems thinking, tradeoffs, and the hard decisions required when abstractions break.

💡 Guest: Robb Winkle

Connect with Robb on LinkedIn:https://www.linkedin.com/in/robbwinkle/

🎙 Hosted by: Warner Moore

Technologist, cybersecurity leader, and Founder of Gamma Force

👉 Learn more about Gamma Force:https://gammaforce.io