Bountifull Podcast: 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 about the real startup journey—the messy, unpredictable, and often misunderstood reality of building great companies. Rowan shares his philosophy on failure, 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 what enough looks like, this conversation is full of insights that will reshape the way you think about risk, ambition, and growth.
About Rowan Simpson:
Rowan Simpson has been at the heart of New Zealand’s most successful technology companies, playing pivotal roles in Trade Me, Xero, Vend, and Timely. As an entrepreneur, investor, and advisor, he has witnessed first-hand how great companies are built—and how easily they can fail. Now, through his writing and investments, he’s helping shape the next generation of high-growth businesses. His book, How to Be Wrong, challenges the way we think about startups, failure, and success, offering a refreshing and sometimes provocative take on what really matters. 📖
Learn more about Rowan’s work and his book:
In This Episode, You’ll Discover:
💡 The Myth of Doing It All: Why success isn’t about doing everything, but about making the 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.
đź’° Investment & Growth: The difference between a startup that thrives and one that stalls.
🎯 Finding Enough: How Rowan defines success beyond financial gain and why balance 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 world
04:08 – What does living a bountiful life mean to Rowan? A fresh take on success and enoughness
07:20 – The startup myth: What people get wrong about success, failure, and overnight wins
13:33 – Trade Me’s early days and the lessons learned from scaling a high-growth company
18:03 – Why Rowan doesn’t call himself an "angel investor" and his philosophy on investing
24:50 – The reality of startup failure and the moments that almost broke now-famous companies
31:17 – The personal sacrifices behind high-growth ventures—finding the balance between work and life
39:47 – High-performing teams: What makes or breaks an early-stage startup?
45:03 – Money and meaning: How Rowan’s relationship with wealth has evolved
49:57 – The discontent that drives ambition—and whether the grass is really greener on the other side
58:25 – Founders get too much advice—how to filter the right guidance for you
1:05:43 – Final thoughts and where to find Rowan’s book How to Be Wrong