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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...
Rowan Simpson on the right way to be wrong is an episode from Business Is Boring by The Spinoff. 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 sc...
This episode belongs to Business Is Boring.
Use the player on this page to stream the episode online.
Published Jul 21, 2025, 62:21 long, audio available.
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. Learn more about your ad choices. Visit megaphone.fm/adchoices
You can listen to Rowan Simpson on the right way to be wrong online on Radio and Podcast. Open the player on this page to stream the available audio.
Rowan Simpson on the right way to be wrong is an episode from Business Is Boring by The Spinoff.
This episode is 62:21 long.
This episode was published on Jul 21, 2025.
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Yes. This page shows related episodes from Business Is Boring when more episodes are available from the podcast feed.
You can listen to Rowan Simpson on the right way to be wrong on this page when the episode audio is available from the podcast feed.
Rowan Simpson on the right way to be wrong is from Business Is Boring by The Spinoff.
Published Jul 21, 2025 and 62:21 long