How To Be Wrong: A crash course in startup success

by Rowan Simpson, Duncan Greive (foreword)

Sometimes the only way to be right is to get comfortable with being wrong.

Most startup advice is dangerously misguided. The mythology of the lone genius founder, the obsession with capital raising and the theatre of startup ecosystems lead countless ventures astray.

Drawing on two decades at the heart of New Zealand's most successful technology companies – Trade Me, Xero, Vend and Timely – Rowan Simpson unravels the messy reality behind familiar glossy success stories. With raw honesty and sharp analysis, he challenges conventional wisdom by sharing compelling firsthand lessons about focused execution, team building and genuine ecosystem growth.

This myth-busting guide is essential reading for founders, investors and policymakers alike. Simpson demonstrates that embracing uncertainty, recognising patterns and learning quickly from mistakes are not just steps on the path to success – they are the path itself.

Genres: Business, Nonfiction

372 pages, Kindle Edition

Published February 24, 2025

Reviews

[Nigel Parker · Rating 5 out of 5]

Parts of this story I knew, and parts filled in gaps and disproved things that I thought I knew.

Thanks, Rowan, for sharing your experience and passion for startups and growth companies and stressing the three ways that we can be wrong:

Neglect (Not Asking the Question),
Error (Making Mistakes),
Malice (Lying to ourselves and others)

Having been heavily involved in startup theatre, investing money in startups through angel programmes, along with working closely with founders through seed, growth and acquisition, investing time and resources into helping their businesses to succeed.

After almost 20 years in corporate roles the last 12 months as a scrappy startup founder have been exhilarating.

I purchased a copy of this book for everyone that is working in our startup. I see it as compulsory reading.

"Ka mua, ka muri" reminds me that true progress comes when we carry forward the wisdom of our past as we step into the future.

I think this whakatauki also talks to servant‑leadership and ancestral reciprocity as an ongoing, intergenerational dialogue.

Literally “those who walk in front, those who walk behind.”
A leader often “walks behind” so their people can walk ahead safely—and then “steps forward” to show the way.

Our tūpuna (ancestors) light the path, and we in turn clear the way for those who follow.

That mutual exchange—receiving guidance, then giving back—keeps the whakataukī alive in our actions and our attitudes towards past and future alike. You talk in this book about your father and the connection you have with him through sport, this is something I also shared with my father, and your grandmother (Marge Simpson) and the persona to ensure she was not left behind as Trade Me developed.

Ehara taku toa i te toa takitahi, engari he toa takitini
“My strength is not that of a single warrior, but that of many.”

Thank you for the role you have played to build the ecosystem in Aotearoa, bring founders together and the contribution you have made to the success of others through your writing and mentorship.

We are all better off as a result of your mahi.

[Ewen Stapley · Rating 4 out of 5]

A very well considered book about business startups that contains so much more. It contains deep thinking about life, business and motivation. Great analogies and inspirational quotes from diverse sources. I am probably not the target reader but enjoyed it and was inspired to think about many topics from a different perspective.

[Sam · Rating 5 out of 5]

This is the most relevant business book I have ever read. I've been on the periphery of startup theatre but not participated. Rather being content to grow a business that on the surface may seem pretty mundane, but executes well.

The stories are a joy, the frameworks make sense and it's encouraged me that I'm doing something meaningful to enrich NZ.

[Jayne · Rating 5 out of 5]

An excellent book which cuts through the Americanised hype and mythology around start ups. It combines a slice of history NZ tech startup history (actually a pretty big slice, because somehow Rowan was there for most of it?!) with some insightful takes on the ecosystem (for want of a better word) and practical frameworks to think about start ups, product management and business in general.

I was glad to read a little about Rowan’s wife Emily and the role she played, albeit indirectly, in making these companies happen. Because if you can only Pick Three à la Randy Zuckerberg, then we all know someone else is probably picking up one or two of the others for you - something not mentioned in the “lone genius” start up lore.

If you’ve read Rowan’s blog you’ll be familiar with most of the material but nonetheless it was worth the $36 to have it all logically stitched together in a lovely physical form.

Thoughtful, funny, and despite the sick burns about startup theatre & startup derivatives, ultimately very positive & optimistic.

[Kirsty O’Hara · Rating 5 out of 5]

For any fence sitters, you’ll likely wonder if you were wrong not to by this book (btw - if you’re massively into weightless exports and enabling tech to solve problems, I’d say don’t let an online shopping cart haunt you … that just seems, well, wrong). Rowan ~ Thank you for distilling 20 years of learnings, into 10 years of writing, resulting in a book that is excessively well crafted and beautifully typeset. Permission to be a quietish one, focused on deep fun, playing a long game was gratefully received. I found it reassuring to hear how little capital you need to get started, how good startups attract funders, how patience plays out, and how the right questions are essential. ‘Flailing’, ‘The Seat of our pants’, and ´Getting Lucky’ were chapters of note! And I applaud your founder-centric ethos!!! The next reader in our house will be my 15 year old Mechatronics obsessed dyslexic son, who has asked me to mark up the chapters he might enjoy (which says a lot, if a reluctant teen reader is willing to skip the kindle and audible versions to crack into the copy we own). For international Startup readers: parts 1 and 2 will be inspiring and globally relevant, with Part 3 sharing a more local ecosystem-centric lens. Much like the infinite product loop, I’m guessing this will be a book I’ll reread and get more nuance from each time (when it’s not out on loan to friends).
Marge Simpson would be impressed!

[Simon Gianoutsos · Rating 4 out of 5]

I enjoyed reading this, helped by the fact that I am familiar with some of the companies and people mentioned.

Lots of good product management and investment insights, particularly with respect to being deeply involved with TradeMe, Xero, Vend and Timely. A superb book to read if you are starting or considering doing a technology startup.

Rowan is critical of the startup theatre that is prevalent as a way to get funding, and advocates for investors and founders to choose one another and for investors to be actively involved to help increase the likelihood of success.

Part of the book is the history of various startups and the startup & venture capital ecosystems in New Zealand.

[Matthew Mudford · Rating 4 out of 5]

The first chapter was an interesting biographical account of some unheard startup stories, awesome. Chapter 2 is a playbook for NZ startups, this could form some part of some curriculum. Chapter 3 felt like a big whinge with little in the way of credit to any ‘ecosystem’ nodes for any level of success, just pot shots at people and orgs doing things differently to how the author would want despite desiring a similar outcome.