AI Rebels

AI can win championships, write convincing answers, and still get the facts wrong. What would make it worthy of our trust? Spencer and Jacob sit down with Jonathan Schaeffer, the AI pioneer behind the checkers-playing system Chinook, for a candid conversation about privacy, bias, accountability, and the road to artificial general intelligence. Jonathan makes the case for independent AI audits, explains his approach to private local AI through KIND, and challenges the idea that language model...

Sreedhar Peddineni has built companies through the internet, SaaS, cloud, and now AI, which makes his perspective especially valuable because he is not reacting to hype — he is comparing this shift to every major technology wave he has lived through. He argues that AI is moving far faster than most leaders and companies can absorb, and that the widening gap between what is possible and what teams are actually doing is becoming a serious competitive threat. His own experience growing GTM Buddy...

Everyone's shipping agents. Almost nobody is asking what happens when a hundred of them go off the rails at 100% utilization while a customer is on the other end. Logan Kelly — CEO of Waxell and a guy who's been punched in the face by real-world sales operations — joins us to argue that a dashboard isn't governance, it's an autopsy, and that most teams are "cavemen playing with fire, hoping there's a bucket of water somewhere." We get into why governance actually *accelerates* agent developme...

Barbara Wittman has spent 25 years cleaning up broken transformation projects, and the root cause is never the technology. In this episode, she breaks down how AI is exposing dysfunction that companies have been hiding for years: misalignment between business and IT, unchecked assumptions, and a total lack of shared understanding. She explains why boards pressure CEOs into AI adoption out of fear, why the people actually executing get sidelined, and why most “AI use cases” fall apart the mome...

Bhaskar Sunkara built AppDynamics into a $3.7B company. Now he's back with Bicycle AI, an always-on agent that catches revenue leaks before your team even knows they exist. In this episode he breaks down why most AI products will never make it to production, how to actually build enterprise trust, and what "doing the boring stuff" really means. We get into real use cases across travel and payments where Bicycle is already saving companies millions. If you're building in AI or buying AI tools ...