“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.
Pre-sales are available now
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.
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.
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Here's 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's perspectives on playing the long game, the reality of "overnight successes", and the value of substance over style are so important and insightful. This book also serves as an inspiring reminder that category defining/leading companies can be built from this part of the world
I wish Rowan had written this 5 years ago, as we set out on our own start up journey. We’ve learned some hard lessons and they are all in this book. Rowan shows success and struggle are two sides of the same innovation coin. Each of his successful business is a result of years of testing ideas relationships, system teams and determination I enjoyed his discussion of government innovation policy as he strips down the borrowed hype of tech policy. This is a remarkably humble honest tale of taking risk, how to roll with it how to beat it and why its worth the effort.
Most start up books focus on hyping up the destination and downplaying the messy, boring and difficult work involved in actually getting there. 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.
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's perspectives on playing the long game, the reality of "overnight successes", and the value of substance over style are so important and insightful. This book also serves as an inspiring reminder that category defining/leading companies can be built from this part of the world
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. And I especially loved his (sometime painful) pearls of wisdom about the roller coaster realities of successful start-ups.
A masterclass in evidence-based ecosystem building and a must-read for anyone interested in what makes startups tick. Rowan's deep thinking on startups and their broader environment is second to none. His writing combines an enviable intellect with pragmatism and lots of hard-won experience to give the reader an objective, nuanced, and accessible insight into why startups succeed or fail - with some rollicking good tales along the way.
I wish Rowan had written this 5 years ago, as we set out on our own start up journey. We’ve learned some hard lessons and they are all in this book. Rowan shows success and struggle are two sides of the same innovation coin. Each of his successful business is a result of years of testing ideas relationships, system teams and determination I enjoyed his discussion of government innovation policy as he strips down the borrowed hype of tech policy. This is a remarkably humble honest tale of taking risk, how to roll with it how to beat it and why its worth the effort.
Exactly the sort of typical boring business-y drivel we've come to expect from you over the years, Dad. I'm sure it will be a bestseller.
Founding a startup is often glamorised as all excitement and a smooth ride to success. The reality? It's bloody tough, messy, and far from a fairytale. This book cuts through the noise with a no-BS take, packed with juicy tales from some of New Zealand's most well-known startups.
Most start up books focus on hyping up the destination and downplaying the messy, boring and difficult work involved in actually getting there. 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.
This book is a masterclass in experiential learning - it's like the Outward Bound course of startup world! 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. Reading this book felt like a conversation with Rowan - deliberate, sharp, and always rewarding. This book puts the 'up' in 'startup'. I loved it.
Building Tractor, I've seen how Rowan Simpson is that rare breed of investor who truly moves the needle for founders. His deep thinking and willingness to tackle the hard stuff - from product pivots to the really hard moments - has been transformative for our business from day one. This book brilliantly captures his journey. What I love most is his refreshing honesty about both the wins and losses. "How To Be Wrong" is a masterclass in effective startup investing that every founder and investor needs to read.
Who is this book for?
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.