“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.
Bursting with stories from Rowan's first hand experiences
From the very beginning of early-stage ventures to the peaks of multi-hundred-million-dollar exits, this myth-busting examination of the startup landscape unravels the messy reality behind familiar glossy success stories.
With raw honesty and hard-earned wisdom from two decades spent working on companies like Trade Me, Xero and Vend, this book exposes the pitfalls of "startup theatre", challenges the obsession with capital raising, and redefines what it truly means to build a startup ecosystem.
It is an essential read for anybody interested in business success—founders, investors, and policymakers alike—proving that 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.
Who is this book for?
If you 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.
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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.