How To Be Wrong: A crash course in startup success

Sometimes the only way to be right is to get comfortable with being wrong.

Most startup advice is dangerously misguided. The mythology of the lone genius founder, the obsession with capital raising and the theatre of startup ecosystems lead countless ventures astray.

Drawing on two decades at the heart of New Zealand's most successful technology companies – Trade Me, Xero, Vend and Timely – Rowan Simpson unravels the messy reality behind familiar glossy success stories. With raw honesty and sharp analysis, he challenges conventional wisdom by sharing compelling firsthand lessons about focused execution, team building and genuine ecosystem growth.

This myth-busting guide is essential listening for founders, investors and policymakers alike. Simpson demonstrates that embracing uncertainty, recognising patterns and learning quickly from mistakes are not just steps on the path to success – they are the path itself.

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"Every upcoming entrepreneur needs to listen to this immediately." – Derek Sivers, author and founder of CD Baby

"There’s wisdom in these stories that could only come from someone who has seen startups from every angle – founder, employee, investor and advisor." – Ana Wight, former CEO of Vend

"A remarkably honest and enjoyable tale of how to take risks – and why it’s worth the effort." – Sir Bill English, former Prime Minister of New Zealand

"Rowan is one of the smartest thinkers I have met on the unique potential Kiwi founders have to create globally significant businesses." – Tim Brown, co-founder of Allbirds

"Exactly the sort of typical boring business-y drivel we’ve come to expect from you over the years, Dad." – Alice Simpson

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Audiobook: 26 September 2025