Rowan Simpson has helped shape some of Aotearoa’s most iconic startups - from Trade Me and Xero to Vend and Timely - usually from behind the scenes. But with the release of his new book How to Be Wrong, he’s stepped into the spotlight to share some hard-earned lessons about success, leadership, and the quiet people who build great companies.

In this episode, we talk about what startup culture still gets wrong, how stories are told and who gets left out, and why the real impact of startups should be measured far beyond headlines and valuations.

Rowan opens up about the mistakes he’s made, the decisions that still stay with him, and the power of doing the right thing even when it’s hard. We dig into ideas he hasn’t been asked about elsewhere - from capital gains tax and the role of government, to the inside story of one of the stories he shares in the book that host Simon Pound was working on with him, the restructure of Vend after a funding round failed.

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Mike Caroncio

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