# Rowan Simpson

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#63: Rowan Simpson – How I Made Millions Backing NZ Startups and NZ's Tall Poppy Problem

Rowan Simpson is one of the most influential figures in New Zealand's startup scene, employee #3 at Trade Me and early shareholder, and an investor in Xero, Vend, and Timely. Some might call him New Zealand's very own Warren Buffett?! Rowan opens up about his journey from startup employee to mu ...

How to Be Wrong: Rowan Simpson on Startups, Squiggly Paths and Why Wellington Won

Some founders make the news. Others build the future. Rowan Simpson is one of those quietly iconic figures who’s helped shape some of Aotearoa’s most successful tech stories—Trade Me, Xero, Vend, Timely—without ever chasing the spotlight. In this wide-ranging conversation, Rowan unpacks the art ...

Growing Kiwi Giants - Trade Me & Xero

New Zealand’s tech sector has produced major success stories, and Rowan Simpson has been behind many of them. As a founding team member of Trade Me and Xero, and an investor in firms like Vend and Timely, Rowan has helped shape a generation of Kiwi innovation. He shares the lessons learned in hi ...

The TradeMe Origin Story: How Rowan Simpson Turned a $10k Investment into a $750 Million Exit

In this episode, we sit down with one of New Zealand’s most quietly influential tech investors and founders: Rowan Simpson. As employee #3 at TradeMe and an early investor in Xero, Rowan helped build two of NZ’s biggest startup success stories. But his story goes far deeper than money. He share ...

Seb Cox: the Lowdown on Venture Studios

In this week’s issue, Seb unpacks for us what it’s like working with a venture studio, his rules of thumb for deciding if an idea is worth pursuing, and some insider thoughts on creativity, team building, and capital raising. The theme throughout Seb’s experiences is the line entrepreneurs must ...

Rowan Simpson on the right way to be wrong

Rowan Simpson has helped shape some of Aotearoa’s most iconic startups - from Trade Me and Xero to Vend and Timely - usually from behind the scenes. But with the release of his new book How to Be Wrong, he’s stepped into the spotlight to share some hard-earned lessons about success, leadership, ...

Ep 15: Rowan Simpson (TradeMe/Vend/Xero/Timely) on growing tech companies & how to be wrong

In this episode of the Funding Files, we interview Rowan Simpson, a key figure in Aotearoa New Zealand's tech scene. He recounts his founding and funding journey, starting with Flat Hunt, which was acquihired by Trade Me, leading to his early involvement in Trade Me's growth and eventual $750 mi ...

Trade Me & Xero’s Rowan Simpson Picks Apart Our Business

Is your business a pet or livestock? Rowan Simpson, employee #3 at Trade Me and an early Xero investor, sits down with Steve, Seamus and business coach Di Foster to pick apart the business behind Between Two Beers. What’s really holding it back, where it could grow, and what should we stop doing ...

Paddy Gower Returns to Discuss Election Night, Kane Williamson’s Golf Sim Obsession & More!

Five years ago Paddy Gower came on Between Two Beers over a lockdown video call, sitting between about seven craft beers. He’s back on Hambassadors, and he’s now off the drink completely. We talk about what giving up drinking and the Newshub redundancy did to him, why election night is “the Ever ...