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

The Startup Playbook PodcastInsights and lessons from the world's best entrepreneurs and investors Twitter Facebook YouTube Instagram Ep181 – James Tynan (Partner – Square Peg Capital) on storytelling & entering the business olympics May 2, 2024 rohitbhargava Podcast 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: [email protected]@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 https://traffic.libsyn.com/secure/startupplaybook/Ep181_-_James_Tynan.mp3Podcast: Play in new window | Download | EmbedSubscribe: RSS admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. 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