Episode Summary:

In this episode of First Cheque, Cheryl and Maxine sit down with James Tynan of Square Peg to explore why EdTech might be one of the most misunderstood (and underinvested) sectors in venture capital. James recounts his early days bootstrapping a startup in Australia’s tough 2001 tech climate, and the lessons he took with him to Khan Academy—where he witnessed firsthand how technology, when done right, can revolutionise education.

Together, they dive into the massive shifts happening in learning today: how kids are skilling up at breakneck speed thanks to platforms like Scratch, YouTube, and AI tutors; why the “Prussian model” of schooling persists; and where personalisation, assessment, and vocational learning could unlock new investment opportunities. James also offers candid advice for early-stage investors trying to spot the next breakout idea in an era of AI-fueled growth—and shares why stepping away from the “prestige path” (like skipping Stanford) was one of his biggest and bravest decisions. Whether you’re an EdTech founder, an investor, or just intrigued by how fast education is evolving, this episode is a must-listen.

Key Takeaways:

00:00 – Intro

02:16 – James’s first big bet – Starting a company in Australia’s early 2000s “hellscape” and the lessons learned

07:18 – Why MOOCs weren’t the answer – The early EdTech hype, misconceptions about online courses, and how Khan Academy did things differently

11:12 – Assessment as the control point – How exams and credentials shape mainstream education and what might disrupt that model

15:08 – AI’s impact on education – Could personalized, AI-driven learning (and cheating) force schools to rethink how we test knowledge?

18:20 – Kids, dopamine, and the next-gen learning paradox – Balancing entertainment and deep learning, and why “edutainment” rules

24:00 – VC skepticism vs. reality – Why it’s so hard to invest in K–12 EdTech, and where vocational and adult learning might be more promising

32:00 – Rapid AI adoption – From legal tech to healthcare, how ambient tools are skyrocketing and what it means for founders

37:00 – Wedges, moats, and growth – The playbook for AI startups moving from “just a feature” to a sustainable product

42:00 – James’s “big kahunas” moment – Choosing Khan Academy over Stanford and why walking away from “prestige” can change everything

47:07 – Wrap-up – The future of EdTech, AI’s role, and parting wisdom for founders and investors

Resources Mentioned

James Tynan on LinkedIn – Partner at Square Peg and former operator at Khan Academy. - https://www.linkedin.com/in/james-tynan-ba54b93/

Square Peg – The VC firm James Tynan is a Partner at. - https://www.squarepeg.vc/

Khan Academy – Free world-class education for anyone, anywhere.

College Board + Khan Academy Partnership – Free SAT and AP test prep.

Ambience Healthcare – AI for clinical documentation and patient notes.

Harvey AI – Legal AI platform disrupting law firm workflows.

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