Why 95% of AI Projects Fail (And How to Be in the 5% That Succeed) with James Baskin of ZeroStone AI

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.

A Quick Word from our Sponsor, Fasken

At Fasken, our clients don’t wait for the future. They build it. As the first and largest dedicated emerging tech practice in Canada, our team is composed of founders, ex in-house counsel, developers and business advisors who have guided clients from startup, to scale-up, to exit. The trust of our clients has enabled us to consistently rank at the top of every major Canadian M&A, Capital Markets and Venture Capital league table. With deep industry knowledge and experience across all areas of emerging and high growth technology including ClimateTech, MedTech, Artificial Intelligence, Fintech, and AgTech we’re your partners within the innovation ecosystem as you transform the landscape of what’s possible.

Tomorrow starts here. Own it with us.

For more information, visit fasken.com/emergingtech and follow us on LinkedIn.

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/

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