#505 From VC to Education Disruptor: Ted Dintersmith on Fixing Math, Schools, and Our Mindset for the AI Era

What if our education system is training students for jobs that no longer exist? In this eye-opening conversation, bestselling author, film producer, and former venture capitalist Ted Dintersmith shares why decades of math education have missed the mark — and what we must teach instead to prepare for the AI-driven future.

From his years in venture capital spotting disruptive innovation to his current mission as an education reformer, Ted reveals why rote memorization and high-stakes testing are holding us back, how AI changes what skills matter, and why creativity, decision-making, and real-world math will be the new competitive edge.

Whether you’re a founder, tech leader, parent, or investor, this episode will challenge your assumptions about what it really means to be future-ready.

Key Takeaways

• Why most high school math has little real-world relevance — and what to teach instead.

• How AI changes the equation for human skills and employability.

• Why decision-making and risk assessment should be core to every student’s education.

• The hidden cost of high-stakes testing and standardized curricula.

• How to reconnect students (and adults) with curiosity and creativity.

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What You’ll Learn

• The wrong math we’ve been teaching for decades — and why it’s stuck in the curriculum.

• How venture capital insights shaped Ted’s view on education reform.

• Practical ways to make math and problem-solving relevant in any career.

• The link between AI, workforce disruption, and the urgent need for new learning models.

• Why embracing unconventional career paths may be the best preparation for the future.

About Ted Dintersmith

Ted Dintersmith is a former partner at Charles River Ventures, named by Business 2.0 as one of the top U.S. venture capitalists. Today, he’s a leading voice in education transformation, focusing on aligning school priorities with the skills and mindsets needed to thrive in a rapidly changing world. He’s the author of multiple books, producer of the Sundance-premiered documentary Most Likely to Succeed, and a sought-after speaker on the future of learning. Ted is consumed with issues at the intersection of education, innovation, and democracy. His films, books, keynotes, and philanthropy focus on the urgency of reimagining school to keep pace with the tsunami of innovation reshaping society. He is the founder of WhatSchoolCouldBe.org, a non-profit organization catalyzing progress in schools, districts, and states across America, and in countries around the globe.

https://www.teddintersmith.com/most-likely-to-succeed

https://www.teddintersmith.com/about-ted

https://www.linkedin.com/in/ted-dintersmith-0211985a/

https://wscbpodcast.com/

https://www.youtube.com/watch?v=Rvhb9aoyeZs

https://www.ted.com/talks/sir_ken_robinson_do_schools_kill_creativity

Episode Highlights

[00:02:00] Ted’s journey from Stanford PhD to startup, VC, and now education advocate

[00:04:30] The “Where’s Waldo” test of high school math — and why most adults fail

[00:09:00] Why AI makes rote math skills obsolete

[00:15:00] The case for teaching estimation, prediction, and optimization

[00:21:00] AI’s exponential growth and its implications for human advantage

[00:29:00] How Finland restructured its education system — and what we can learn

[00:34:00] Understanding risk and decision-making — the missing life skill

[00:43:00] Why creativity is the most valuable skill schools should protect

[00:48:00] Multiple Choice — Ted’s upcoming documentary on integrating career and academics

[01:00:00] The venture capital lesson: the best ideas often face the most resistance