This week, Hugh Mason published his review of my book How To Be Wrong. With his permission, I’d like to share it with you…
Hugh actually has a small uncredited cameo in the book, in the chapter about the time I spent in Singapore in 2012 and 2013. He was one of the co-founders of JFDI (officially the Joyful Frog Digital Innovation bootcamp), where I was a mentor.1 In a blog post the previous year I’d recommended it to any Kiwi founders who were underwhelmed by local incubator programmes. Three who took me up on that were Cameron & Bradley Priest and Carl Thompson - the founders of Trade Gecko. Eight years later they sold that company for a reported US$80 million.2 Not bad!
Hugh is an Associate Professor at the National University of Singapore. Originally from the UK, he’s been in Singapore for a long time, and has done a huge amount to foster startups and encourage people there to be excited about working on them.
In this considered review he turns the book’s argument back on itself, describing it as “a retrospective account designed to warn us against taking retrospective accounts too seriously”. He manages to be generous and sceptical at the same time. Just the way I like it!
For those of you who have read the book already, I hope this is a useful refresher. And for those who haven’t, I hope it encourages you to grab a copy and enjoy it for yourself.
Over to Hugh…
Can entrepreneurs learn from experience without turning uncertainty into mythology?
Rowan Simpson’s reflective account of building and backing technology companies asks whether entrepreneurs can learn from experience without turning uncertainty into mythology
“History isn’t fact. It’s narrative,” Rowan Simpson writes near the beginning of How To Be Wrong. It’s an unusual premise for a founder retrospective/advice book. In my reading, most see a successful entrepreneur finally rewarded with time on their hands trying to figure out what the hell the last decade or two was all about, selecting anecdotes that seem consequential in hindsight, then using them as evidence for recommendations to others following in their footsteps. Simpson has spent enough time building and investing in successful technology companies to distrust those resulting stories, however well-intended.
Perhaps unwisely I was listening to the audiobook version of Patrick O’Brian’s Joseph Banks: A Life over the same time I read How To Be Wrong (Yes, that’s the same Patrick O’Brian who wrote Master and Commander, with the lead character played by another eminent Kiwi, Russell Crowe). Anyway, the combination turned out to be interesting as both books collided inside my head. Joseph Banks was, of course, the botanist who accompanied Captain James Cook on his first voyage to the South seas, mapping New Zealand and touching on Australia along the way. O’Brian’s book is a very entertaining story based on the anecdotes of that voyage, as recorded in Banks’ journals. It struck me that trying to write a retrospective narrative as a founder is rather similar. One thing happens after another, an author records what they can about the strange things and events along the way (Cannibals! Tahiti! Kangaroos! WTF!), and only years later gets around to trying to make sense of it all. Great entrepreneur-storytellers like Derek Sivers have made encore careers out of doing just that, and indeed Sivers had a hand in helping to shape Simpson’s book. From a professional perspective I hope many more founders are inspired to do the same, because the episodes they choose to record take us inside the lived experience of entrepreneurship and often make fantastic teaching cases for educators like me. All the more if they are honest about the messiness of the experience.
That matters because, viewed in the rear mirror, companies such as Trade Me and Xero can look like products of prescient founders making unusually good decisions. Yet, from inside, Simpson remembers how people acted without knowing what would happen, pursued ideas that went nowhere, changed their minds, got lucky and depended on colleagues whose contributions largely disappeared from the eventual success story. How To Be Wrong is Simpson’s attempt to recover some of that uncertainty before, somewhat paradoxically, deriving practical advice from it to the point that it changes the way he now wants to hear pitches as an investor. This makes the book a curious exercise in entrepreneurial sensemaking: a retrospective account designed to warn us against taking retrospective accounts too seriously.
Simpson has an unusually good vantage point from which to attempt it. He was an early employee at Trade Me, an early investor in Xero and subsequently backed companies including Vend and Timely. The book’s three sections (“Build”, “Invest” and “Grow”) progressively widen the lens from what happens inside ventures, through the decisions of those who finance them, to the institutions that attempt to create entrepreneurial ecosystems. What connects all three is the honesty of recognising that doing something new will always involve being wrong, again and again. Simpson does not celebrate failure or repeat the tired Silicon Valley injunction to “fail fast” but rather builds on a more consequential observation: entrepreneurs have to act before they possess enough information to know whether their assumptions are correct. The practical problem is therefore not how to avoid being wrong, but how to discover that you are wrong, while there is still time to do something about it. Simpson repeatedly returns to measurement, feedback, experimentation and actual customer behaviour. Ideas must encounter reality. Teams need people willing to disagree. Activity needs measures capable of distinguishing progress from mere motion.
This makes him particularly good on the mundane work subsequently edited out of entrepreneurial success stories. He has little interest in ideas and sees first-time founders’ fears that somebody might steal theirs as naive. Truth is, indifference from the world is a much more common experience: people don’t say no, they just don’t care. Simpson highlights execution as the real challenge for entrepreneurs as they learn, pivot and turn an idea into something that people actually want. Hence, as an investor, Simpson wants above all to learn what a founder has learned: a humble, honest “we realised ...” is a much better way to start a pitch to him than an overbearingly confident “X is broken ...”. He is interested in what what a team actually learnt, why customers are doing what they do, which assumptions remain untested, and what evidence would change their minds.
Simpson’s argument grows broader, and perhaps more interesting, in the section called “Grow” where he turns his attention to New Zealand’s efforts to foster an entrepreneurial ecosystem. He points out that governments can make the same error as founders: measuring what is conspicuous rather than what matters. More programmes, startups and investment do not necessarily amount to greater entrepreneurial capability. His alternative is slower and less amenable to policy announcements. Successful companies create experienced people; those people become founders, employees, advisers and investors elsewhere; subsequent companies create another generation. Ecosystems accumulate capability. They are grown rather than installed and it all takes time.
There is, however, an unavoidable difficulty in Simpson’s perspective, as his evidence comes largely from a remarkably successful career. He knows which experiments mattered and which apparent setbacks became consequential. The unsuccessful alternatives mostly remain invisible. Recognition of hindsight does not abolish hindsight. That matters because the book sometimes moves rather quickly from remembered episode to general prescription. As in the journals of Joseph Banks, an experience can establish that something happened; it cannot by itself establish why it happened or whether another entrepreneur should behave similarly. How To Be Wrong is most convincing when Simpson allows the messiness of events to survive his interpretation of them. To his credit, he repeatedly acknowledges luck, context and collective effort. He is also suspicious of the heroic founder around whom business histories are commonly organised.
The book is dedicated instead to the “quiet ones”: the less visible people through whose accumulated work companies actually get built. Simpson, and the New Zealand ecosystem are perhaps both quieter voices in the shouty world of startups than most. This helps explain why How To Be Wrong is more interesting than its subtitle, A Crash Course in Startup Success, suggests. Simpson wants other people to build companies, but he wants to encourage them by dismantling rather than reproducing the mythology surrounding entrepreneurship. The resulting lesson is less satisfying than a sure-fire formula for success, but a lot more useful. Entrepreneurs must make consequential decisions without knowing whether they are right. The important capability is therefore not prescience. It is organising practice so that assumptions repeatedly encounter reality, errors become visible, and beliefs can change. No personal business memoir can escape the limitations of retrospective sensemaking from a N=1 sample. How To Be Wrong succeeds unusually well when it leans into the paradox faced by every founder-author sharing their experience: we learn from experience by turning it into stories, even as those stories risk concealing what the whole experience was actually like.
Buy The Book
How To Be Wrong: A Crash Course in Startup Success
Rowan Simpson, Electric Fence, 2025. ISBN: 9780473729967.
Also available as an ebook and audiobook, from all of the places where you find those.
Singapore, Yah La - rowansimpson.com, March 2012.
My blog post about my time at the first JFDI.
Intuit to acquire Singapore’s TradeGecko for a reported $80m - Tech In Asia, August 2020.