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 of getting it wrong (and why that’s okay). From his early days in Wellington’s tech era to investing in ideas that didn’t always go to plan, he shares what it really takes to build something meaningful—and why the best founders aren’t the loudest in the room.Rowan’s gift? He asks better questions. Ones that challenge the hype and centre what really matters: culture, founder-investor fit, and building for the long game. Whether you’re in the trenches of your own start-up or just love a good origin story, this episode is a masterclass in humility, insight, and seriously good storytelling.Plus, don’t miss Rowan in real life. We’re hosting the launch of his new book, How to Be Wrong, at Mountain Club Beach St on Friday 13 June. Space is limited—so if you’re keen to catch this conversation live, get in touch with the team.