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

In this episode of Project Gamma, Warner Moore sits down with Ray Bohac, serial entrepreneur, technologist, and Co-Founder & CEO of Spearfish.AI. Ray has built multiple companies from zero to one, including CallCopy (Uptivity), and now he’s redefining how contact centers understand their customers through AI.

We explore the hard-earned lessons of a 5× founder, the real meaning of product-market fit, how to avoid costly scaling mistakes, and the hidden operational signals inside customer conversations that companies never knew how to measure…until now.

Ray explains why contact centers sit on a goldmine of unstructured data, how Spearfish extracts actual intelligence instead of vanity metrics, and why concepts like Time to Relevance can save millions in churn and service inefficiencies.

Whether you’re a founder, technical leader, AI practitioner, or customer experience professional, this episode gives you a new lens for building better companies and for truly understanding customers.

Books Mentioned:

Give and Take — Adam Grant

The Innovator’s Dilemma — Clayton Christensen

Mastering the Rockefeller Habits / Scaling Up — Verne Harnish

The 7 Habits of Highly Effective People — Stephen Covey

💡 Guest: Ray Bohac

Reach him on LinkedIn: https://www.linkedin.com/in/raybohac/

🎙 Hosted by Warner Moore

Technologist, cybersecurity leader, and Founder of GammaForce

👉 Learn more about GammaForce: https://gammaforce.io

What happens when a lifelong engineer ends up running HR?In this episode of Project Gamma, Warner Moore sits down with Alan Gilbert, a technology executive who turned structure into culture and helped build startups like CoverMyMeds into billion-dollar success stories.

Alan shares how he transitioned from corporate life at DuPont to startup chaos, why he believes great leaders “make the right way the easy way,” and what it really takes to build teams, manage founders, and eventually step back to focus on impact.

We talk about:✅ Moving from engineering to people leadership✅ Working with founders and managing startup chaos✅ Decentralizing engineering teams✅ Lessons from retirement and mentoring entrepreneurs

Books mentioned:

• The Innovator’s Dilemma – Clayton Christensen

• What Got You Here Won’t Get You There – Marshall Goldsmith

• Slack – Tom DeMarco

💡 Guest: Alan Gilbert Reach him at: alan@swiftcurrent.partners Learn more: https://graniteball.com

🎙️ Presented by Gamma Force Fractional cybersecurity leadership for tech and healthtech companies. 👉 Learn more at https://gammaforce.io

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