When the Facts Change cover image

When the Facts Change

The startup savant behind Trade Me and Xero

Feb 20, 2025
Rowan Simpson, a pivotal figure in New Zealand's tech scene with success in Trade Me and Xero, shares insights from his book, "How to Be Wrong: A Crash Course in Startup Success." He reflects on the dramatic acquisition of Trade Me and the hard-earned lessons from the highs and lows of startups. He discusses the significance of teamwork and adaptability, the unique challenges faced during COVID-19, and the impact of housing affordability on the entrepreneurial landscape. His journey reveals what it truly takes to navigate the volatile world of tech startups.
40:04

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

  • Rowan Simpson's journey emphasizes the essential role of resilience and adaptability in navigating the volatile landscape of tech startups like Xero and Vend.
  • The acquisition of Trade Me dramatically reshaped New Zealand's digital economy, illustrating how strategic decisions and funding challenges can significantly influence startup success.

Deep dives

The Impact of Critical Business Decisions

A key moment in New Zealand's economic landscape took place in 2006 with Fairfax's acquisition of Trade Me for $750 million, significantly shaping the digital media environment in the country. This milestone highlighted the precarious nature of startups, as Trade Me initially faced near-failure due to a lack of funding and strategic revenue models. The introduction of a success fee system ultimately transformed Trade Me from a struggling classified site to a lucrative enterprise. Such decisions underscore the volatility inherent in the startup space, where fleeting moments can determine a company’s trajectory.

Get the Snipd
podcast app

Unlock the knowledge in podcasts with the podcast player of the future.
App store bannerPlay store banner

AI-powered
podcast player

Listen to all your favourite podcasts with AI-powered features

Discover
highlights

Listen to the best highlights from the podcasts you love and dive into the full episode

Save any
moment

Hear something you like? Tap your headphones to save it with AI-generated key takeaways

Share
& Export

Send highlights to Twitter, WhatsApp or export them to Notion, Readwise & more

AI-powered
podcast player

Listen to all your favourite podcasts with AI-powered features

Discover
highlights

Listen to the best highlights from the podcasts you love and dive into the full episode