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James Tynan

James Tynan

Former Partner at Square Peg

Investor

James Tynan is a Partner at Square Peg, where he invests in exceptional founders solving significant problems across Australia, Israel, and South-East Asia. Before joining Square Peg, James was the CEO of Startmate, Australia's most powerful startup network, where he created the Startmate Fellowship to enhance people's careers through the network. Prior to that, he was based in the US, where he played a pivotal role in scaling Khan Academy from a YouTube success to the largest ed-tech organization globally. As VP of Strategy and Operations at Khan Academy, he built the Business Development and Adoption (Marketing) functions and managed the Educator/Classroom business. James holds a Bachelor of Laws (LLB) and a Bachelor of Arts in Media Arts & Production from the University of Technology Sydney, where he was awarded the University Medal.

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In their own words

From James Tynan shares his unpopular views on startup accelerators · The History of the Australian Startup Ecosystem - Interview Series
I think that accelerators are generally terrible businesses and generally not a good idea. I think Startmate is an exception.
▶ James Tynan shares his unpopular views on startup accelerators

Career

  1. Now Former Partner · Square Peg
  2. Until 2020 CEO · Startmate
  3. Earlier · Scale-up VP, Strategy and Operations · Khan Academy
  4. Earlier Consultant · McKinsey & Company
  5. Earlier General Manager · Purpose PBC

Sources: squarepeg.vc

Key moments

Jump straight to the part of How James Tynan from Square Peg Invests in EdTech you want.

  1. 2:16 James’s first big bet – Starting a company in Australia’s early 2000s “hellscape” and the lessons learned
  2. 7:18 Why MOOCs weren’t the answer – The early EdTech hype, misconceptions about online courses, and how Khan Academy did things differently
  3. 11:12 Assessment as the control point – How exams and credentials shape mainstream education and what might disrupt that model
  4. 15:08 AI’s impact on education – Could personalized, AI-driven learning (and cheating) force schools to rethink how we test knowledge?
  5. 18:20 Kids, dopamine, and the next-gen learning paradox – Balancing entertainment and deep learning, and why “edutainment” rules
  6. 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
  7. 32:00 Rapid AI adoption – From legal tech to healthcare, how ambient tools are skyrocketing and what it means for founders
  8. 37:00 Wedges, moats, and growth – The playbook for AI startups moving from “just a feature” to a sustainable product
  9. 42:00 James’s “big kahunas” moment – Choosing Khan Academy over Stanford and why walking away from “prestige” can change everything
  10. 47:07 Wrap-up – The future of EdTech, AI’s role, and parting wisdom for founders and investors

Heard on

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First Cheque · 7 April 2025 How James Tynan from Square Peg Invests in EdTech
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The History of the Australian Startup Ecosystem - Interview Series · 31 May 2022 James Tynan shares his unpopular views on startup accelerators

Square Peg on Day One

Square Peg Square Peg is a venture capital firm founded in Australia in 2012, dedicated to supporting visionary founders in Australia, New Zealand, Israel, and Southeast Asia. 2 people · 5 episodes →

Connections

Spot something wrong? Suggest a correction Updated 25 September 2026

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