In this episode of Tank Talks, Matt Cohen is joined by James Baskin, Founder and CEO of ZeroStone AI, to explore how businesses can transition from AI experimentation to real-world impact. James, a three-time founder with multiple successful exits, shares his journey from engineering at the University of Toronto to building and selling telecom ventures alongside Globalive’s Anthony Lacavera. He offers valuable insights into leadership, resilience, and overcoming imposter syndrome.
Drawing from over 300 conversations with CEOs and AI leaders, James discusses why many companies are “AI-aware but not AI-ready.” He reveals how ZeroStone helps mid-market firms turn failed pilots into scalable, impactful AI systems. James also highlights the differences between generative and agentic AI, the dual transformation of technology and people, and the importance of fostering a culture of curiosity and continuous learning for long-term success. This episode offers practical advice for founders and executives navigating the AI revolution.
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The Founder’s Journey & Imposter Syndrome (00:09:41)
“Scaling Your Everest”: the emotional toll of leadership
Facing imposter syndrome in boardrooms
Anthony Lacavera’s hard advice: “You don’t know what you’re doing.”
How that painful truth became a turning point
From Go-To-Market to AI Strategy (00:16:00)
Consulting with Series A/B startups on GTM and sales
Transition to AI after dozens of founder conversations
Why most OKRs fail: objectives must tie directly to long-term strategy
Introducing a new framework rooted in “Seven Powers” by Hamilton Helmer
Building ZeroStone AI (00:22:22)
Founding mission: help mid-market firms (>$50M revenue) unlock real AI value
Observing 300+ executive discussions on AI, awareness high, action low
Why cultural and digital transformations must happen together
Moving beyond “copilots” to autonomous, agentic AI systems
The AI Leadership Gap (00:24:27)
Boards push for AI results, but internal teams lack clarity
“You need both a data transformation and a human capital transformation.”
The rise of self-selecting teams, who adapts, who opts out
Building cultures of learning, not fear
Why 95% of GenAI Pilots Fail (00:31:16)
Most projects don’t touch core business processes
Generative AI ≠ Agentic AI: only the latter changes workflows
AI agents as “digital workers” vs. human productivity tools
How CEOs can start small, measure impact, and scale over three years
Overcoming the Pilot Trap (00:36:30)
Scaling beyond sandboxes by fixing data architecture
The critical role of clean data lakes, enrichment, and governance
Why early-stage companies move faster than legacy enterprises
About James Baskin
Founder & CEO of Zero Stone AI
A three-time founder with successful exits, James is a seasoned expert in go-to-market strategy, OKRs, and sales leadership. Through ZeroStone AI, he is now guiding mid-market companies to unlock true, measurable value from agentic AI, moving beyond failed pilots to autonomous systems that transform businesses.
Connect with James Baskin on LinkedIn: https://www.linkedin.com/in/jamesbaskin/
Visit the ZeroStone AI Website: https://www.zerostone.ai/
Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1
Visit the Ripple Ventures website: https://www.rippleventures.com/
