1<!DOCTYPE html> 2<html lang="en"> 3 4 <head> 5 <meta name="generator" content="Hugo 0.154.5"> 6 <meta http-equiv="Content-Type" content="text/html" charset="UTF-8" /> 7<meta http-equiv="X-UA-Compatible" content="IE=edge,chrome=1" /> 8<meta name="viewport" content="width=device-width, initial-scale=1.0" /> 9<meta name="author" content="Rowan Simpson" /> 10<meta name="description" content="Hello, Iâm Rowan ⦠Rowan Simpson 11I live in Aotearoa New Zealand. 12I am the chairman of Hoku Group, our family office, which combines our private investments, â¦" /> 13<link rel="canonical" href="https://rowansimpson.com/" /> 14<link rel="alternate" type="application/rss+xml" title="Rowan Simpson RSS Feed" href="https://rowansimpson.com/index.xml" /><link href="/main.min.432c9455e9a9d1084ede573e881d769cc5addfc25d29634730d59e0e60a68a5d.css" rel="stylesheet" /> 15 16<link rel="apple-touch-icon" sizes="180x180" href="/apple-touch-icon.png"> 17<link rel="icon" type="image/png" sizes="32x32" href="/favicon-32x32.png"> 18<link rel="icon" type="image/png" sizes="16x16" href="/favicon-16x16.png"> 19<link rel="manifest" href="/site.webmanifest"> 20 21<link rel="preconnect" href="https://fonts.googleapis.com"> 22<link rel="preconnect" href="https://fonts.gstatic.com" crossorigin> 23<link href="https://fonts.googleapis.com/css2?family=Lora:ital,wght@0,400;0,700;1,400;1,700&family=Montserrat:wght@400;700;800&display=swap" rel="stylesheet"> 24 25 <title>Rowan Simpson</title> 26 27 28 <meta property="og:url" content="https://rowansimpson.com" /> 29 <meta property="og:type" content="article" /> 30 <meta property="og:title" content="Rowan Simpson" /> 31 <meta property="og:description" content="Essays, quotes, and nuggets by Rowan Simpson - thoughts on technology, business, and New Zealand" /> 32 <meta property="og:image" content="https://rowansimpson.com/img/shared/how-to-be-wrong-cover.6659dce4c0feb08390edc80b9de73c24976a368316700b964a1270c894ebb7e9.png" /> 33 <meta property="og:image:alt" content="Rowan Simpson" /> 34 <meta property="og:image:width" content="1800"> 35 <meta property="og:image:height" content="1200"> 36 <meta name="twitter:card" content="summary_large_image" /> 37 <meta name="twitter:creator" content="@rowansimpson" /> 38 39 40 </head> 41 42 <body> 43 44 45 <div class="w-full"> 46 <nav id="header" class="nav-light fixed w-full z-10 top-0"> 47 48 <div id="progress" class="w-full md:max-w-4xl mx-auto flex flex-wrap items-center justify-between mt-0 p-4"> 49 50 <div class=""> 51 <a class="text-base no-underline hover:no-underline font-extrabold text-xl" href="/"> 52 Rowan Simpson 53 </a> 54 </div> 55 56 <div class="block lg:hidden"> 57 <button id="nav-toggle" class="flex items-center px-3 py-2 border rounded appearance-none focus:outline-none"> 58 <svg class="fill-current h-3 w-3" viewBox="0 0 20 20" xmlns="https://www.w3.org/2000/svg"> 59 <title>Menu</title> 60 <path d="M0 3h20v2H0V3zm0 6h20v2H0V9zm0 6h20v2H0v-2z" /> 61 </svg> 62 </button> 63 </div> 64 65 <div id="nav-content" class="hidden w-full flex-grow flex lg:items-center lg:w-auto lg:block mt-2 lg:mt-0 rounded-md z-20"> 66 <ul class="list-reset flex flex-1 flex-col py-4 lg:py-0 lg:flex-row lg:justify-end items-start"> 67 <li class="hidden"> 68 <a class="inline-block no-underline hover:text-underline py-2 px-4" href="/">About</a> 69 </li> 70 <li class=""> 71 <a class="inline-block no-underline hover:text-underline py-2 px-4" 72 href="/essays/">Essays</a> 73 </li> 74 <li class=""> 75 <a class="inline-block no-underline hover:text-underline py-2 px-4" 76 href="https://howtobewrongbook.com" target="_blank" rel="noopener noreferrer">Book</a> 77 </li> 78 <li class=""> 79 <a class="inline-block no-underline hover:text-underline py-2 px-4" 80 href="https://topthree.rowansimpson.com" target="_blank" rel="noopener noreferrer">Top Three</a> 81 </li> 82 <li class=""> 83 <a class="inline-block no-underline hover:text-underline py-2 px-4" 84 href="/nuggets/">Nuggets</a> 85 </li> 86 <li class=""> 87 <a class="inline-block no-underline hover:text-underline py-2 px-4" 88 href="/archive/">Archive</a> 89 </li> 90 </ul> 91 </div> 92 </div> 93</nav> 94 </div> 95 96 <div class="container w-full md:max-w-4xl mx-auto p-4 py-20 prose"> 97 <div class="w-full text-xl text-gray-800 leading-normal"> 98 <h3 id="hello-im-rowan-">Hello, Iâm Rowan â¦</h3> 99<p><figure> 100 <img src="/img/shared/rowan-portrait.a1ffb96c76a1ae15e6bac10a81d2a5c3f84358a22bba33ba61519e2dfdcc222a.jpeg" alt="Rowan Simpson" 101 width="1200" height="800" 102 loading="lazy" decoding="async"><figcaption>Rowan Simpson</figcaption></figure></p> 103<p>I live in Aotearoa New Zealand.</p> 104<p>I am the chairman of <a href="https://hoku.nz">Hoku Group</a>, our family office, which combines our private investments, early-stage venture investments and <a href="https://hoku.nz/foundation">Hoku Foundation</a>, our non-profit foundation.</p> 105<p>I am the author of the book <a href="https://howtobewrongbook.com">How to be Wrong: a crash course in startup success</a>, published in February 2025. <a href="https://shop.howtobewrongbook.com">Buy now</a>.</p> 106<p>I am a founder of and early investor in multiple high-growth technology businesses.</p> 107<p>In 2000 I was employee #3 at <a href="https://trademe.co.nz">Trade Me</a>
107. I led the software development team as the business grew rapidly to become an iconic Kiwi brand, including through the sale to Fairfax for $750m in 2006.</p> 108<p>In 2007 I was a pre-IPO investor in <a href="https://xero.com">Xero</a>, and worked as part of the original executive team at time the business was listed on the NZX. Xero is now one of the most successful businesses ever started in New Zealand, with millions of global subscribers.</p> 109<p>In 2010 I was one of the initial investors in <a href="https://vendhq.com">Vend</a>. I was the chairman of the board of directors until 2015. Vend was acquired by Lightspeed for ~US$350m in 2021.</p> 110<p>In 2013 I was the first investor in <a href="https://gettimely.com">Timely</a>. I was as an advisor and director through to the sale to EverCommerce for ~$US100m in 2021.</p> 111<p>Current active startup investments include <a href="https://histerling.com">Sterling</a>, <a href="https://huckleberry.work">Huckleberry</a>, <a href="https://www.tractorventures.com">Tractor Ventures</a>, <a href="https://www.melodics.com/">Melodics</a>, <a href="https://www.lightyearssolar.co.nz">Lightyears Solar</a>, <a href="https://www.atomic.io/">Atomic</a>, <a href="https://parkable.com/">Parkable</a>, <a href="https://stickybeak.co/">StickyBeak</a>, <a href="https://www.firmcheck.com">Firmcheck</a> and <a href="https://getthematic.com/">Thematic</a>.</p> 112<p>I hold a Bachelor of Science degree in Computer Science from <a href="https://www.wgtn.ac.nz/">Victoria University of Wellington</a>.</p> 113<h3 id="buy-the-book">Buy the book</h3> 114<p><a href="https://howtobewrongbook.com"><figure> 115 <img src="/img/shared/how-to-be-wrong-cover.6659dce4c0feb08390edc80b9de73c24976a368316700b964a1270c894ebb7e9.png" alt="" 116 width="1800" height="1200" 117 loading="lazy" decoding="async"></figure></a></p> 118<hr> 119<h4 id="selected-media">Selected Media</h4> 120<ul> 121<li><a href="https://www.youtube.com/watch?v=VEH8bvvQ0QQ">The Story Behind Trade Me</a>, <em>Between Two Beers Podcast</em>, 2025</li> 122<li><a href="https://www.youtube.com/watch?v=5kCMRwmZycE">Why Govt shouldn’t be picking start-up winners</a>, <em>Q+A, TVNZ</em>, 2025</li> 123<li><a href="https://www.rnz.co.nz/national/programmes/saturday/audio/2018977017/how-to-be-wrong-a-crash-course-in-startup-success">How to be Wrong: a crash course in startup success</a>, <em>Sunday Morning, Radio New Zealand</em>, 2025</li> 124<li><a href="https://www.newstalkzb.co.nz/on-air/mike-hosking-breakfast/audio/rowan-simpson-kiwi-entrepreneur-talks-start-ups-business-confidence-and-economic-growth/">“No shortage of capital”: How to build successful businesses in NZ?</a>, <em>Mike Hosking Breakfast, NewstalkZB</em>, 2025</li> 125<li><a href="https://businessdesk.co.nz/article/technology/startups-being-wrong-and-near-death-experiences">Startups, being wrong, and near-death experiences</a>, <em>BusinessDesk</em>, 2025</li> 126<li><a href="https://www.nzherald.co.nz/business/is-artificial-intelligence-having-its-lightbulb-moment-rowan-simpson/BC2S3LPH2BBP5LH2ZKRN7UCZJM/">Is AI having its lightbulb moment?</a>, <em>NZ Herald</em>, 2025</li> 127<li><a href="https://thespinoff.co.nz/business/29-01-2025/scrapping-callaghan-innovation-is-a-necessary-reset-but-what-comes-next">Scrapping Callaghan Innovation is a necessary reset. But what comes next?</a>, <em>The Spinoff</em>, 2025</li> 128<li><a href="https://vimeo.com/1068554281">In conversation with Joel Little</a>, <em>Sunrise Festival</em>, 2024</li> 129<li><a href="https://www.youtube.com/watch?v=5xdkipArVY4">Keynote: If technology is the answer, what is the question?</a>, <em>Sport NZ Connections Conference</em>, 2024</li> 130<li><a href="https://open.spotify.com/episode/4zK2nGldeuH1uZMEEKWBSa">
130High Flyers Podcast with Vidit Agarwal</a>, 2022</li> 131<li><a href="https://hard-mode.simplecast.com/episodes/rowan-simpson-YRsC23WL">Hard Mode Podcast with Matt Allen: Technology & People</a>, <em>Tractor Ventures</em>, 2021</li> 132<li><a href="https://podcasts.apple.com/nz/podcast/what-weve-learned-about-working-from-home/id1558395118?i=1000537851639">When The Facts Change Podcast with Bernard Hickey: What weâve learned about working from home</a>, <em>The Spinoff</em>, 2021</li> 133<li><a href="https://medium.com/airtree-venture/rowansimpson-182ceced2b12">The Halo Effect</a>, <em>AirTree Ventures</em>, 2020</li> 134<li><a href="https://thespinoff.co.nz/business/07-07-2019/the-reluctant-founder/">The reluctant founder</a>, <em>The Spinoff</em>, 2019</li> 135<li><a href="https://www.youtube.com/watch?v=j2wRe1cffz4">In conversation with Sam Gribben</a>, <em>Sunrise</em>, 2019</li> 136<li><a href="https://thespinoff.co.nz/business/08-05-2019/in-the-beginning-we-had-no-idea-on-the-birth-and-growth-of-trade-me/">In the beginning, we had no idea: on the birth and growth of Trade Me</a>, <em>The Spinoff</em>, 2019</li> 137<li><a href="https://www.youtube.com/watch?v=kD5TjNfJiJM">A conversation with Adela May</a>, <em>Startup Grind, Wellington</em>, 2018</li> 138<li><a href="https://player.whooshkaa.com/episode?id=192135">Open The Pod Bay Doors Podcast with Ian Gardiner</a>, <em>Australian Innovation Bay</em>, 2018</li> 139<li><a href="http://www.radionz.co.nz/national/programmes/sunday/audio/2018626703/rowan-simpson-how-to-make-a-startup-business-last">How to make a startup business last</a>, <em>Sunday Morning, Radio New Zealand</em>, 2017</li> 140<li><a href="https://play.acast.com/s/business-is-boring/the-rowan-simpson-founder-centric-approach-to-bein">Business is Boring Podcast with Simon Pound</a>, <em>The Spinoff</em>, 2017</li> 141<li><a href="http://www.radionz.co.nz/news/national/283459/flag-the-rest,-the-red-peak-is-best,-says-campaigner">Flag the rest</a> & <a href="http://www.radionz.co.nz/national/programmes/morningreport/audio/201770659/could-the-red-peak-design-fly">Could the RedPeak design fly?</a> & <a href="https://www.rnz.co.nz/national/programmes/morningreport/audio/201769568/social-media-provides-platform-for-flag-design-change">Social media provides platform for flag design change</a>, <em>Morning Report, Radio New Zealand</em>, 2015</li> 142<li><a href="http://www.stuff.co.nz/business/industries/5460928/On-being-a-most-blessed-geek">On being a most blessed geek</a>, <em>Stuff</em>, 2011</li> 143<li><a href="http://www.radionz.co.nz/national/programmes/saturday/audio/2376802/playing-favourites-with-rowan-simpson">Playing Favourites with Kim Hill</a>, <em>Radio New Zealand</em>, 2010</li> 144<li><a href="http://www.stuff.co.nz/business/4048810/Entrepreneurs-buy-into-point-of-sale-firm">Entrepreneurs buy into point-of-sale firm</a>, <em>Stuff</em>, 2010</li> 145<li><a href="https://www.nzherald.co.nz/technology/news/article.cfm?c_id=5&objectid=10615430">Six degrees experiment finds camera owner</a>, <em>NZ Herald</em>, 2009</li> 146<li><a href="https://vimeo.com/1048043025">Fireside chat with Sam Morgan</a>, <em>Webstock</em>, 2008</li> 147<li><a href="https://www.geekzone.co.nz/content.asp?contentid=7181">Former Trade Me manager joins Xero</a>, <em>Geekzone</em>, 2007</li> 148<li><a href="https://www.slideshare.net/rowan/teched-nz-2006-keynote-rowan-simpson">Microsoft TechEd Keynote</a>, 2006</li> 149<li><a href="http://www.scoop.co.nz/stories/SC0104/S00040.htm">Trade Me Diversifies Into Flats & Flatmates</a>, <em>Scoop</em>, 2001</li> 150</ul> 151<!-- * [Opinions split over RedPeak flag](http://www.newshub.co.nz/home/new-zealand/2015/09/opinions-split-over-red-peak-flag.html), *3 News*, 2015--> 152<!--* ["How To Pick A Winner"](https://www.rnz.co.nz/programmes/two-cents-worth/story/2018704875/how-to-pick-a-winner), *Two Cents' Podcast, Newsroom/RNZ*, 2019--> 153<!--* Deloitte Fast50 Keynote, ["Lessons from Red Peak"](https://www.youtube.com/watch?v=xXYQIMz_8O4), 2015--> 154<!--* [People Supporting TriNZ](https://www.facebook.com/TriathlonNZ/videos/1706184766091716/), *Tribe*, 2018--> 155 156 </div> 157 </div> 158 159 160 </body> 161 162 <footer> 163 164 <div class="container max-w-4xl mx-auto flex py-8"> 165 <div class="w-full mx-auto flex flex-wrap"> 166 <div class="flex w-full md:w-1/2 "> 167 <div class="px-4 w-full"> 168 <h3 class="hidden font-bold text-gray-900">About</h3> 169 <p class="py-4 text-gray-600 text-sm"> 170 Made in Aotearoa from local and imported ingredients. 171 </p> 172 </div> 173 </div> 174 175 <div class="flex w-full md:w-1/2"> 176 <div class="px-4 w-full md:text-right"> 177 <h3 class="hidden font-bold text-gray-900">Links</h3> 178 <p class="py-4 text-gray-600 text-sm"> 179 <a 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