“A landmark addition to the slim shelf of truly important New Zealand business books
Rowan Simpson, veteran investor and early employee at Trade Me, Xero, Vend and Timely, delivers a masterclass in embracing uncertainty, recognising patterns and transforming mistakes into fuel for success.
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Bursting with stories from Rowan's first hand experiences
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 reading 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.
Sometimes the only way to be right is to get comfortable with being wrong.
Where can I buy the book?
How To Be Wrong is available now in paperback and ebook, plus (coming soon) audiobook.
Buy online and get the book delivered directly:
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Auckland: The Open Book
Auckland: Unity Books
Hamilton: Poppies Books
Wellington: Unity Books
Christchurch: Scorpio Books
and many more
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Who is Rowan Simpson?
"The most important figure in New Zealand technology you've never heard of."
Rowan Simpson has been at the heart of New Zealand's most successful technology companies. As a founding team member at Trade Me and Xero, he witnessed firsthand how great companies are built through consistent execution. His subsequent investments and hands-on work with ventures like Vend and Timely have helped shape a generation of high-growth companies.
Here's a taste of what some early reviewers are saying about this book.
There's wisdom in these pages that could only come from someone who has seen startups from every angle - founder, employee, investor and advisor.
Rowan is one of the smartest thinkers I have met on the unique potential Kiwi founders have to create globally significant businesses. This book brings extraordinary authenticity to this glossy opportunity while reminding us all that being wrong in a start-up is a necessary part of finding 'right'.
Here's an author who understands the power of mythology, and shows how it's at play in our popular understanding of tech start-ups - their births, triumphs, and failures.
There's wisdom in these pages that could only come from someone who has seen startups from every angle - founder, employee, investor and advisor.
Oscar Wilde said "To live is the rarest thing in the world. Most people exist, that is all." Rowan has lived four of the greatest New Zealand startup lives in history, and they are told in delicious detail in these pages.
Rowan cracks the code on start-ups and it's gold. Wherever you are on your entrepreneurial journey, you need to read this book.
A masterclass in effective startup investing that every founder and investor needs to read.
Rowan is one of the smartest thinkers I have met on the unique potential Kiwi founders have to create globally significant businesses. This book brings extraordinary authenticity to this glossy opportunity while reminding us all that being wrong in a start-up is a necessary part of finding 'right'.
Rowan has captured the lessons from a successful career and shaped them into practical advice that will be incredibly useful to any founder or early stage employee.
A masterclass in experiential learning - Rowan's insights about focussing on the rewards of Deep Fun rather than the sugar rush of Shallow Fun will change how you think about starting and building organisations. I loved it.
Startup leaders will love it. Political leaders & their advisors must read it.
Here's an author who understands the power of mythology, and shows how it's at play in our popular understanding of tech start-ups - their births, triumphs, and failures.
A remarkably humble honest tale of taking risk, how to roll with it, how to beat it and why its worth the effort.
Rowan has done a very rare double act in life - wildly successful founder and investor. So anyone interested in start-up success must read this.
This book is a delightful window into the world of some of New Zealand's best startups and in my opinion founders. If you ever wanted to be a fly on the wall this is your opportunity.
Where can I see more?
Read and watch some of the recent interviews and articles about the book.
by Rowan Simpson
Scrapping Callaghan Innovation is a necessary reset. But what comes next?
Who should read this book?
Want to understand what it really takes to build successful companies, and why their success or failure affects us all, without the usual hyperbole and sugar-coating? This book is for you.
You'll learn candid lessons about growth, fundraising, team building, and how to navigate the journey from early-stage to high-growth company - including what it really takes beyond a good idea.
You'll gain insights into what makes startups successful, how to evaluate opportunities, and how to add genuine value beyond just capital.
You'll discover the realities of startup life, the different stages companies go through, and how to contribute effectively as part of a high-growth team.
Whether as a friend, advisor, accelerator manager, or ecosystem builder - you'll learn which activities genuinely help founders and which may actually be counterproductive.
You'll discover how early-stage and high-growth companies can meaningfully contribute to prosperity, what constraints they face, and how to create the conditions for them to thrive.
You'll get an insider's perspective on the evolution of New Zealand's emerging startup ecosystem over two decades through the stories of companies like Trade Me, Xero, Vend and Timely.
You'll gain practical insights into what support for innovation and entrepreneurship actually works (and what doesn't) when trying to grow a vibrant startup ecosystem.
You'll discover the fascinating inside stories of how these companies were started - the struggles, near-death experiences, and key decisions that shaped their success.
You'll come away with better questions to ask about how high-growth companies can benefit everyone, not just founders and investors.
The companies described in this book are remarkable startup success stories. Together they have created thousands of high-paying jobs, generated billions in value, and helped put New Zealand's technology sector on the global map. They each faced unique challenges but found innovative ways to succeed and scale. Rowan was a key early employee, investor, advisor and director - helping shape their trajectory.
In 2000 Rowan was employee #3 at Trade Me. He led the software development team as the business grew rapidly to become an iconic Kiwi brand, including through the sale to Fairfax for $750m in 2006.
In 2007 Rowan was a pre-IPO investor in Xero, and worked as part of the original executive team at the time the business was listed on the NZX. Xero is now one of the most successful businesses ever started in New Zealand, with millions of global subscribers.
In 2010 Rowan was one of the initial investors in Vend. He was the chairman of the board of directors until 2015. Vend was acquired by Lightspeed for ~US$350m in 2021.
In 2013 Rowan was the first investor in Timely. He was as an advisor and director through to the sale to EverCommerce for ~$US100m in 2021.