How to Be Wrong and Still Succeed with Rowan Simpson

🌟"Most people can do anything, but a lot of people interpret that to mean they can do everything. And that’s just not true. You have to choose." 🌟The startup world is filled with big dreams, bold bets, and the constant pressure to be right. But what if the secret to success isn’t about always getting it right, but learning how to be wrong? Rowan Simpson has spent decades at the heart of New Zealand’s most successful tech companies—Trade Me, Xero, Vend, and Timely—and his journey is a testament to the power of making mistakes, adapting, and building things that last.In this episode, we talk aboutthe real startup journey—the messy, unpredictable, and often misunderstood reality of building great companies. Rowan shares his philosophy onfailure, investment, and decision-making, why he challenges the way we think about success, and how his book,How to Be Wrong, offers a fresh perspective on navigating uncertainty. Whether you're an entrepreneur, investor, or just someone figuring out whatenough looks like, this conversation is full of insights that will reshape the way you think about risk, ambition, and growth.Episode Highlights:💡The Myth of Doing It All: Why success isn’t about doingeverything, but about makingthe right choices.🚀Behind the Scenes of New Zealand’s Biggest Startups: The untold stories from Trade Me, Xero, Vend, and Timely.📉Failure as a Superpower: Why being wrong isn’t the problem—not learning from it is.🏆What Really Makes a High-Performing Team: The crucial early hires that shape a company’s future.💰Investment & Growth: The difference between a startup that thrives and one that stalls.🎯Finding Enough: How Rowan defines success beyond financial gain and whybalance is harder than it sounds.📖How to Be Wrong: The key takeaways from Rowan’s book and why every founder should embrace uncertainty.Timestamps:00:00 – Introduction to Rowan Simpson and his journey through New Zealand’s startup world04:08 – What does living a bountiful life mean to Rowan? A fresh take on success andenoughness07:20 – The startup myth: What people get wrong about success, failure, and overnight wins13:33 – Trade Me’s early days and the lessons learned from scaling a high-growth company18:03 – Why Rowan doesn’t call himself an "angel investor" and his philosophy on investing24:50 – The reality of startup failure and the moments that almost broke now-famous companies31:17 – The personal sacrifices behind high-growth ventures—finding the balance between work and life39:47 – High-performing teams: What makes or breaks an early-stage startup?45:03 – Money and meaning: How Rowan’s relationship with wealth has evolved49:57 – The discontent that drives ambition—and whether the grass is really greener on the other side58:25 – Founders get too much advice—how to filter the right guidance for you1:05:43 – Final thoughts and where to find Rowan’s bookHow to Be WrongGuest Bio:Rowan Simpson has been at the heart ofNew Zealand’s most successful technology companies, playing pivotal roles inTrade Me, Xero, Vend, and Timely. As anentrepreneur, investor, and advisor, he has witnessed first-hand how great companies are built—and how easily they can fail. Now, through hiswriting and investments, he’s helping shape the next generation of high-growth businesses. His book,How to Be Wrong, challenges the way we think aboutstartups, failure, and success, offering a refreshing and sometimes provocative take on what really matters.📖Learn more about Rowan’s work and his book:👉Website |How to Be Wrong |Buy the Book |LinkedInThe Bountifull Podcast explores what it means to live a bountiful life through stories of wellbeing, resilience, connection and creativity. Bountifull emerged out of a simple yet profound desire to see more joy in the world.Join the joy channel:www.bountifullworld.com/subscribe/⁠#startup #decisionmaking #enough #podcast #decision-making