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!

Timestamps

• 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:

Scendar 

Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com

Vanta

Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on.
Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time.
Get started with a Sydney-based Vanta team member today, or watch a 3-minute demo to learn more, at vanta.com/playbook.

Links mentioned

James’ links

• LinkedIn
• Twitter/X
• Square Peg

People mentioned

• Sal Khan
• Kate Mason
• Bill Gates
• John Doerr
• Annie Case
• Eric Schmidt
• Cliff Obrecht
• Didier Elzinga
• Daniel Petre
• Niki Scevak
• Nick Crocker
• Michael Batko
• Jethro Cohen
• George Peppou
• Alex Zatarain

Companies mentioned

• McKinsey & Company
• Canva
• Culture Amp
• Khan Academy
• Y Combinator
• Google
• Stanford University
• Playbook Ventures
• Kleiner Perkins
• Microsoft
• MIT
• Harvard University
• Uber
• Startmate
• Blackbird
• Grok Ventures
• Skip Capital
• Vow
• Q-CTRL
• EightSleep

Feedback/connect/say hello:

Rohit@startupplaybook.co
@RohitBhargava7 (Twitter)
/rohbhargava (LinkedIn)
@rohit_bhargava (Instagram)
My Youtube Channel

Credits:

Music: Paycheck

Other channels:

Find all of the links for the podcast on Linktree here

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