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Human-in-the-loop AI tutoring

In this episode of Chalk and Code, host Theron Davis sits down with Raj Valli, Founder and CEO of Thinkster Math, an AI-driven tutoring company that blends patented AI with human coaches to deliver measurable outcomes in math learning.

Drawing on experience across 12 industries and decades of nonprofit work in education, Raj unpacks why so many students still struggle with foundational math and what it really takes to design systems that reliably close learning gaps instead of just delivering content.

From AI-powered diagnostics that probe “wells of knowledge” to deep analytics that surface patterns like “this student struggles with two-digit multiplication when numbers end in 9,” Raj explains how Thinkster uses data, instructional design, and human tutors together to guarantee outcomes rather than hope for them. He also explores the limits of today’s AI, arguing that most models still rely on crystallized intelligence, while truly transformative learning and innovation depend on human fluid intelligence.

If you care about how AI, behavior science, and human relationships can be combined to help learners “learn better, faster, sooner,” this conversation offers a practical, grounded look at what high-accountability edtech can be.


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About the guest

Raj Valli

Raj Valli is co-founder and CEO of Thinkster Math, a remote tutoring program that blends patented AI-driven personalization with human coaching to build math and analytical skills. Thinkster uses AI-powered diagnostics to pinpoint exactly where a learner’s understanding starts, then gives tutors targeted insights to make every session count. Before founding Thinkster, Raj worked across 12 industry verticals on three continents and volunteered extensively with a nonprofit providing basic education to underprivileged children in India.

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