First Cheque with Cheryl Mack & Maxine Minter 
About James Tynan
James Tynan is a former partner at Square Peg, the venture capital firm he joined in 2020 and left at the end of 2025. In early 2026 he said he was in an exploratory phase, talking with people interested in investing and building in artificial intelligence.
At Square Peg he was a principal before being named a partner in 2023, and his interests included education, climate, healthcare and software. He joined from Startmate, the Australian startup accelerator, where he was chief executive. Earlier he worked at McKinsey & Company in Australia and helped scale Khan Academy in the United States.
On The History of the Australian Startup Ecosystem interview series he shared his contrarian views on accelerators, and on First Cheque he explained how he invests in edtech.
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- Venture Capital, Fundraising, Startup Lessons
In conversation.
2 episodes
Start hereJames Tynan shares his unpopular views on startup acceleratorsA one-on-one interview built around his contrarian views on startup accelerators, a subject he knows from running Startmate.
First Cheque with Cheryl Mack & Maxine Minter 
The History of the Australian Startup Ecosystem - Interview Series James Tynan shares his unpopular views on startup accelerators
Recorded as Principal, Square Peg
Go straight to the good bits.
Key moments from How James Tynan from Square Peg Invests in EdTech.
- 2:16James’s first big bet – Starting a company in Australia’s early 2000s “hellscape” and the lessons learned
- 7:18Why MOOCs weren’t the answer – The early EdTech hype, misconceptions about online courses, and how Khan Academy did things differently
- 11:12Assessment as the control point – How exams and credentials shape mainstream education and what might disrupt that model
- 15:08AI’s impact on education – Could personalized, AI-driven learning (and cheating) force schools to rethink how we test knowledge?
- 18:20Kids, dopamine, and the next-gen learning paradox – Balancing entertainment and deep learning, and why “edutainment” rules
- 24:00VC skepticism vs. reality – Why it’s so hard to invest in K–12 EdTech, and where vocational and adult learning might be more promising
- 32:00Rapid AI adoption – From legal tech to healthcare, how ambient tools are skyrocketing and what it means for founders
- 37:00Wedges, moats, and growth – The playbook for AI startups moving from “just a feature” to a sustainable product
- 42:00James’s Biggest Brave Moment – Choosing Khan Academy over Stanford and why walking away from “prestige” can change everything
- 47:07Wrap-up – The future of EdTech, AI’s role, and parting wisdom for founders and investors
In their own words.
“The ability to ingest a whole bunch of really well-known information and then regurgitate it is something AI can do way better than any student.”
“I think that accelerators are generally terrible businesses and generally not a good idea. I think Startmate is an exception.”
The path so far.
- Now
Former Partner · Square Peg
- Until 2020
CEO · Startmate
- Earlier · Scale-up
VP, Strategy and Operations · Khan Academy
- Earlier
Consultant · McKinsey & Company
- Earlier
General Manager · Purpose PBC
Sources: squarepeg.vc
Square Peg on Day One
Square Peg is a venture capital firm founded in Australia in 2012 that backs startups from Australia, New Zealand, Southeast Asia and Israel, with investment themes…
2 people · 5 episodes
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Spot something wrong? Suggest a correctionUpdated 29 October 2026
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