PHOTO: Trade Me wasn’t born out of Silicon Valley—it was crafted in the hands of a small team of New Zealanders. FILE
🧠 The Kiwi IT Consultant Who Became a Multi-Millionaire Tech Icon
Trade Me wasn’t born out of Silicon Valley—it was crafted in the hands of a small team of New Zealanders who didn’t have a blueprint, just belief. And one of the earliest and most influential of them all? Rowan Simpson.
What started as a side project to help Kiwis find flats turned into one of New Zealand’s biggest-ever startup success stories—scaling from humble beginnings to a $750 million exit. But for Simpson, the story of Trade Me is only the beginning.
🛠️ The Trade Me Origin Story: From Flathunt to Fortune
In 1999, Simpson was working as an IT consultant in Sydney when he built Flathunt, a site to help Kiwis find places to live. That small project put him on the radar of Trade Me founder Sam Morgan, who was then developing a broader online marketplace.
Simpson joined as employee #3 and helped shape the site’s development, user experience, and back-end systems during its most crucial years. The early days were rough—money was tight, and the idea of success seemed more like a gamble than a guarantee.
But by 2006, Trade Me had exploded in popularity and was acquired by Fairfax Media for a staggering $750 million. It was a historic moment in New Zealand’s digital economy.
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💸 Beyond the Payday: Lessons from the Edge of Bankruptcy
While many celebrate the sale, few know how close Trade Me came to failing. In interviews and his own writing, Simpson has openly shared the brutal realities—late nights, financial pressure, and the rollercoaster of startup life.
But what makes Simpson unique is not just his success—it’s his candour. He challenges clichés like “fail fast” and says most lessons come from being wrong slowly, learning through humility and patience.
💡 Building Xero and Backing Kiwi Founders
After Trade Me, Simpson didn’t sit back. He became one of the first investors in Xero, helping Rod Drury turn it into a global accounting software powerhouse. He also chaired Vend, which later sold for over $500 million, and invested in companies like Timely, Melodics, and Thematic.
Simpson is now widely regarded as one of New Zealand’s top tech investors—but he’s also refreshingly grounded. He focuses not just on financials, but on purpose, people, and product.
📘 “How to Be Wrong”: Simpson’s Blueprint for Smarter Startups
In his book How to Be Wrong, Simpson dives deep into what most business books avoid: failure.
He categorises being wrong into three buckets:
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Mistakes you didn’t know were mistakes
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Mistakes you chose to ignore
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Mistakes you learned from (hopefully)
The book offers practical, no-BS advice for entrepreneurs: be skeptical, focus on the fundamentals, and stop pretending that big success happens overnight. It doesn’t.
🏡 Life After the Millions: Family, Focus, and the Future
Now living near Nelson, Simpson has shifted his energy into investing with heart. Through his private firm, he supports startups that align with his values—integrity, innovation, and long-term thinking.
He’s also a vocal advocate for balance, parenting with purpose, and saying no more often. For Simpson, success is no longer just about the bank account—it’s about building a meaningful life.
📊 Trade Me Property: The Legacy Lives On
While Trade Me has changed hands several times since the Fairfax sale, the site remains a major player in New Zealand’s property and retail markets. Trade Me Property continues to dominate the online housing space, offering buyers, sellers, and renters a central hub for listings, data, and trends.
Simpson may have left the day-to-day operations long ago, but the systems and philosophy he helped shape still ripple through the business today.
🎯 Key Takeaways from Rowan Simpson’s Journey
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Don’t romanticise failure. Learn from it, but don’t aim for it.
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Build slowly and deliberately. Growth is a marathon, not a marketing stunt.
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Put people first. Culture and teams are more powerful than code.
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New Zealand has global potential. Think big—but stay grounded.
💬 Final Word
Rowan Simpson didn’t just build a company—he helped create an ecosystem. From Trade Me to Xero, his fingerprints are all over New Zealand’s most exciting tech ventures.
His story is a reminder that with grit, vision, and a willingness to be wrong—you can help shape the future of an entire country.