WholeCEO With Lisa G Podcast · 2026-06-22 · 15 min
Most AI initiatives fail. Not because of the model. Because organizations skip the boring, essential engineering work that makes software survive contact with reality. Jake Dubin has spent 25 years building production systems, starting with neural networks that solved CAPTCHA back in 1999. He is the founder of Transcendent Software and is building CoffeeBreak, an AI platform focused on reliable human-centered workflows. In this episode, Jake breaks down why human in the loop almost never means what people think it means, what vibe coding is, and why it is quietly creating massive technical debt, and why the same fundamentals that built dependable software for decades still apply, no matter how powerful the model gets. If your AI investment is not delivering what you promised the board, this episode tells you exactly why.
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