You’re book How to be Wrong is very well produced. You published this yourself – can you tell us a bit about why you chose to “self publish”?
It was a mixture of stubbornness and impatience.
I started out working with a traditional publisher, however that opportunity evaporated when their team was re-structured. At that point I decided I could get it finished faster by myself than by going back to the beginning with somebody else. That made some things more difficult (e.g., I’ve learned more than I ever intended about things like paper stock and international shipping) but the flip side is it gave me much more control over the final product and, even more importantly to me, how it was launched and marketed.
I’m really proud of the end result. However, calling it “self-published” feels a bit misleading. It was edited by Toby Manhire, who is obviously hugely experienced, and the design and layout was done by Imogen Greenfield, who has also worked on many books and magazines previously. There were many other people who helped with advice along the way.
Your pitch to bookstores was pretty slick for a first-time author promoting their own work. Did you have any advice from any booksellers along the way? Or what resources helped you navigate the publishing and distribution for your book?
I don’t know what I don’t know – maybe that’s the key!
I was introduced to a potential distributor early on, and had a very discouraging conversation with them — they didn’t think they could sell many copies. After that I realised I needed to put most of my effort into selling it directly to the audience of people I’d already built for myself and hope that bookstores would eventually see the potential. So I tried to make it easy for people to buy directly from me (https://howtobewrongbook.com), and just as easy for stores who want to stock it. I’m very grateful to those bookstores who have been willing to take that risk.
I’ve discovered en route there are just not many business books like this published here. Perhaps because it’s not obvious there is an audience, although that’s a bit chicken-and-egg.
You’ve no doubt spent a lot of time in bookshops around NZ. From observing their businesses, do you have any comments on the business model or observations on how this very traditional business is carving a place for itself in the future (or not)?
I’ll be honest: I sometimes find physical bookshops quite intimidating. Or maybe overwhelming is a better word. I’m not somebody who loves browsing and there are so many titles to choose from, so I always appreciate a good recommendation. Perhaps that’s the unique value that bookstores can provide?
I know that the retail business model is really challenging. That’s unlikely to get any easier in the future. But there will always be room for retailers who focus on doing the things that large online stores will never replicate. As always, start with the loyal customers you have, or hope to have, and work back to the experience that will keep them coming back and telling their friends.
How long did it take you to write the book?
There isn’t a simple answer to this question, unfortunately.
I didn’t begin with a blank page. I started blogging in 2006, when I was still working at Trade Me, and I’ve been writing about these companies ever since, sharing the patterns and lessons I was learning along the way. So, many of the ideas in the book have had many iterations over the years.
In 2021, in a thinly veiled attempt to clear out a long neglected “Drafts” folder, I set myself the ambitious goal of publishing a post on Substack every week. On Boxing Day, feeling a combination of satisfaction and relief, I published the 52nd and final post. I thought I was finished. I was finished. But others saw that as just the beginning. After that it took about 18 months to package it up into a book, with a couple of false starts along the way. Luckily I didn’t know it would take that long at the outset or I may have been reluctant to start.
What advice would you give to other independently published authors?
Actually, similar advice to what I would give to somebody who would like to start their own company: be prepared for it to be much more difficult than you might anticipate; keep in mind the trade-off between good, fast and cheap (while self-publishing might seem like the cheaper option that’s probably only because you’re not putting a price on your own time); and surround yourself with the best people you can to help make that happen, because while it might only be your name on the cover, it will be a team effort to get there.
If you were hand-selling your book on the shop floor, how would you pitch it? Can you write a catchy 50- to 100-word shelf talker for your book?
Of course! Here are 85 words:
“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. This myth-busting guide 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. Sometimes the only way to be right is to get comfortable with being wrong.”
What businesses are you keeping an eye on or what startups are exciting you?
Here are three local startup companies I’ve invested in and am currently working with, for example:
Stickybeak: An innovative market research platform transforming how companies gather consumer insights through engaging, interactive surveys that deliver faster, more authentic feedback. (https://www.stickybeak.co/)
Melodics: Music education software that teaches people to play instruments through game-like exercises, adaptive learning, and real-time feedback that makes practice feel like play. (https://melodics.com/)
Thematic: A powerful customer feedback analysis platform that uses AI to automatically identify themes in survey responses and reviews, helping businesses uncover actionable insights from qualitative data. (https://getthematic.com/)
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