The TradeMe Origin Story: How Rowan Simpson Turned a $10k Investment into a $750 Million Exit

In this episode, we sit down with one of New Zealand’s most quietly influential tech investors and founders: Rowan Simpson.

As employee #3 at TradeMe and an early investor in Xero, Rowan helped build two of NZ’s biggest startup success stories.

But his story goes far deeper than money. He shares how he went from near-bankruptcy to the $750M TradeMe exit, his role in backing Kiwi founders, his philosophies on parenting, time, failure, AI—and why ‘business is like a rollercoaster’ metaphor is bullshit.

🧠 Topics include:

– The TradeMe origin story (and the nightmare before the sale)

– Why “fail fast” is bad advice

– Lessons from Xero, Vend, and a year of world travel

– How to pitch to investors (and how not to)

– Saying no, picking your 3 things, and building a life of purpose

– Sport, family, AI, and the future of New Zealand tech

📍 Watch, listen, and subscribe on YouTube, Spotify or Apple Podcasts.

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