The Startup Playbook Podcast

Insights and lessons from the world's best entrepreneurs and investors

Ep181 – James Tynan (Partner – Square Peg Capital) on storytelling & entering the business olympics

My guest for Ep181 of The Startup Playbook Podcast was James Tynan, Partner at Square Peg Capital.

Square Peg Capital is one of Australia’s largest venture capital funds. In 2022, Square Peg closed a $860M fund, taking its total funds under management to $2.4B across all of its funds.

Prior to this, he founded Tiny Green Gorilla, a company he bootstrapped for 8 years before it was acquired in 2008.

He was also an early team member and eventually the VP of Strategy and Operations at the Khan Academy, which was the largest edtech startup in the world at that time.

In this episode we covered a range of topic including:

  • How James and his wife make important decisions by their “moleskinning” process
  • The key ingredients that made Kahn Academy so successful
  • Why investors need to overcome their own fears
  • The importance of operating in your zone of genius
  • & much more!


  • 01:50 – James’ Background
  • 03:41 – Starting his first business in first year university
  • 08:17 – Joining Khan Academy
  • 12:08 – “Moleskine-ing” tool for decision making
  • 14:55 – Building a venture backed business isn’t for everyone
  • 21:22 – What made Khan Academy so successful
  • 32:40 – Transitioning out of Khan Academy and deciding what’s next
  • 36:36 – The early days of Startmate
  • 42:15 – How investors should think about helping companies they invest in
  • 44:34 – The decision to leave Startmate and join Square Peg
  • 52:16 – James’ “zone of genius”
  • 57:31 – Overcoming your fear as an investor and coming from a place of service
  • 03:23 – Picking the right fund and partner as a founder
  • 01:05:09 – Advice to founders on approaching investors
  • 01:06:28 – What James looks for when making investments
  • 01:07:38 – Storytelling advice to founders

Our partners

A big thank you to Kate Mason, Jethro Cohen and George Peppou for their help with this interview.

Also a big shout out to our partners for the show:


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Links mentioned

James’ links

People mentioned

Companies mentioned

Feedback/connect/say hello:

[email protected]
@RohitBhargava7 (Twitter)
/rohbhargava (LinkedIn)
@rohit_bhargava (Instagram)
My Youtube Channel


Music: Paycheck

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