2015 Annual Report

Exhausted, Invigorated, Excited

In the 1960s, while their husbands were en route to the moon, the wives of the Apollo astronauts got sick of journalists asking how they were feeling, so came up with the collective non-answer of: “proud, pleased and delighted“. We’ll never know how they really felt.

If I had to nominate my equivalent, as 2015 turns into 2016, I would go with “exhausted, but invigorated and excited”. It’s accurate. It only just scratches the surface.

If I’m honest, I’m pleased to see the back of 2015, but it’s finished on a much better trajectory and what is to come is shaping up to be epic.

Let me explain…

Not Work, If You Enjoy It

Top of Corkscrew

A photo posted by Rowan Simpson (@nzrhan) on

I didn’t take many days off in 2015, but when I did I packed them full:

A winter’s New Year at Whistler in Canada, including a blast down the Olympic bobsled run from Vancouver 2012 (hitting a top speed of 126.6 km/h on the final corner); my first visit to Disneyland; camping with my boys at Lake Rotoiti (before getting smoked out by sandflies); climbing up and flying down the eastern end of the new Old Ghost Road MTB track; a family clean sweep at X-Race Nelson in March (with the painted toe nails to prove it!); driving to Hanmer via the Rainbow Road and back on the Molesworth with MOD and family at Easter; teaming up with my brother to finish in 8th Place in the Wellington City Safari in May (not bad for a couple of old novices!); cycling on the Avanti Dome velodrome; kayaking in Abel Tasman with Tango in October; racing Sarah Walker on a BMX over 20m at the Fast50 Awards in November (for the record: I finished second); completing my first full marathon in Queenstown in November, and another blast down the Remeka Track. And, then, just before my punished toe nails got complacent, running the Tongariro Crossing with Darryl in December.

All of that meant at times that my downtime wasn’t very down.

Keeping Score

I managed three months off Sky Sport at the start of the year, a streak eventually broken by the Black Caps’ unexpected progress in the World Cup. Still that was a nice break, which left me refreshed ahead of the exertions of the Rugby World Cup later in the year.

I didn’t completely deny myself live sport though – highlights were another scorching day and entertaining night at the Australian Open in Melbourne in January (including the treat of finally seeing Roger Federer live, plus Serena Williams at the peak of her powers, 13 years after I first saw her at Wimbledon), followed by the Cricket World Cup featuring the Black Caps live in Christchurch, Wellington and Auckland. It was also an honour to attend the Halberg Awards in February.

If I play my cards right, involvement in sport in its various guises is going to be to be a bigger and bigger part of how I spend my time. I hope.

It’s Business Time

Business, Business, Business.

A photo posted by Rowan Simpson (@nzrhan) on

I try to avoid describing the experience of working on an early stage ventures as being “like a roller-coaster”. Sure there are highs and lows, often in quick succession, but generally the intention is not to end up where you started. So, for the purposes of summarising the year just been, let’s go with squiggly line.

I made two new early-stage investments during the year, in Wynyard and Melodics. On the other side of the ledger two smaller existing investments, Respondly and Gelato, accepted acquisition offers (from Buffer and Mashape respectively). In both cases the products will continue on under new ownership and I wish them well.

A significant chunk of my time was spent helping the companies I’ve invested in previously try to raise more. Vend, Atomic and ThisData (previously Revert) all successfully closed new investment rounds during the year, and I went again in all of them. Amongst the companies I work with directly, Timely was the exception, as they continued their impressive expansion without being distracted by looking for new capital.

In total I’ve invested a little over $5.5m now, across 23 ventures. They already owe me nothing, even assuming all of the remaining investments are worthless (which might be safest). Haters gonna hate, but I’m increasingly proud of the companies I’ve backed and the progress they’ve made and I’m excited to have the opportunity to work closely with some of them along the way. I try to contribute more than I capture.

I encourage all of the founders I work with to ignore the cheering from the grandstand and run hard to the tape with the capital they have. If they do that all of them have an opportunity to be another story worth telling.

At the Deloitte Fast50 Awards in November I quietly celebrated a three-peat, as Vend joined Trade Me and Xero to become the third company I’ve worked with to earn the title of fastest growing technology company. In their case they followed up 4th place in 2014 with 7th place overall this year. Being near the top of that index two years in a row is nothing to sneeze at. For them it was a bright spot in an otherwise challenging year, so well earned. While my direct role ended soon after that, I’m thrilled to have been involved over the last five years. I’ll watch now from the side of the pool.

As the year wound down I also reluctantly stepped down from the board at Powershop. Selfishly, the three years I’ve been a director was an invaluable apprenticeship for me, and I’m grateful to John, Ari and the team for having me along for the ride during an interesting time in the development of their business.

And did those feet in ancient time?

Sunset bonfire, with a new filter I invented called "Canon 7D screen" #nocord

A photo posted by Rowan Simpson (@nzrhan) on

Once again I spent a big part of the year not at home. I was away for 185 days (one less than in 2014, meaning that record stands … for now), completing 90 flights and two inter-island ferry crossings in the process.

Most of that was work, but there was some visits to amazing new places in the mix too.

In June I had the opportunity to travel to Israel as part of an Australian technology delegation organised by Square Peg Capital. It was a great group and we were privileged to meet some remarkable people and visit some normally off limits places. Highlights included lunch with Eitan Wertheimer, a visit to an airforce base, a tour of the old city of Jerusalem and caking myself in mud and floating in the Dead Sea. I wish I’d had more time to reflect on the many lessons and write it up, but as it happened it was a pretty distracted trip, immediately followed by an intense week in Berlin, so I’m left with photos and fading memories. But I did return convinced that there is zero chance that we can reproduce their Start Up Nation miracle in NZ without compulsory military service for all 18 year olds.

Business Incubation Center

A photo posted by Rowan Simpson (@nzrhan) on

Then, in August, Emily and I finally made it to Africa with Jake and Billy from Nuru International. It was an honour to meet their teams in Kenya and Ethiopia and see the enormous impact they are having in both of those communities. Given the calibre of people involved it’s been a relatively easy project to support over the last five years, and especially cool to visit Kuria in Kenya (near the border with Tanzania), where the impressive local leadership team have now taken over the on-going management and are quickly planning further growth into surrounding areas.

We were also able to visit the incredible monolithic chiseled churches at Lalibela in Ethiopia and prior to that spent a week kicking back on a beach in the Seychelles. Blurring the line between travel for work and pleasure generally means I get to experience the best of both worlds. I’m fortunate to have a great network of people that I see regularly in both Auckland and Wellington. And, even when I’m overseas, it’s great to be able to mix in great food and/or live sport in Melbourne or “Artisanal liquid nitrogen blood orange and pistachio cookie ice cream” @ Smitten Ice Cream in SF. My problems are entirely first world problems.

Why'd ya have to go and make things so complicated?

A photo posted by Rowan Simpson (@nzrhan) on

When I was at home, a lot of that time was soaked up in a new building project. In the course of the year it’s gone from hole in the ground to now completed working space. It’s been fun watching it take shape (and a pretty interesting shape it is too – triangles are not just for flags, you know!) In early December it was excellent to see it used in anger for the first time at the third annual Flounders Retreat. Spaces are for the people that fill them, and this one is going to be a good one by that measure, hopefully.

Red Peak?

In September I stumbled somewhat accidentally into the later stages of the NZ flag debate when a post I wrote about a design that had caught my attention was widely shared and suddenly #RedPeak entered the lexicon.

Last light of the day on the "First to the Light" flag. #RedPeak #nofilter

A photo posted by Rowan Simpson (@nzrhan) on

It’s not everyday that you convince parliament to sit under urgency, so that was something, I suppose. I learned more about flags and politics than I really wanted to. It still seems unresolved whether it was a left wing or right wing conspiracy, but if you work it out do let me know! But in the end it was all for nothing – for every person who was convinced to support Red Peak, ten voted for one of the Lockwood Fern+Stars flags, so the seemingly pre-determined winner prevailed. That was obviously disappointing but not surprising.

It would have been great to see Red Peak be the contender, but I’m still proud that we managed to get a real choice in the first vote. It would have been easy to just make a throw away snarky comment and forget about it. But, it was so much more inspiring to see a national conversation about identity and how we represent ourselves to each other and on the world stage. I’m not sure that would have happened otherwise. I’ve been amazed to see the creativity displayed by people who found something in the Red Peak design that made it their own. It was genuinely remarkable. I hope that conversation continues.


But, sadly, it doesn’t seem likely. Those who short-listed the options were determined to pick a design that was unmistakably from New Zealand. A bit of the silver fern combined with the current flag is hard to compete with, given that criterion. And so were left with the Hakarena flag, which to me screams 1994 Cricket World Cup. But, she’ll be right, I suppose. Luckily I will be some distance away, physically and mentally, by the time the second vote rolls around next year.


Following a wonderful disconnected month or so at the start of the year, I spent a some time thinking slightly longer ahead than I normally do. While I was doing that I read an article written by Ben Casnocha which has ended up having a significant impact.

It started a domino fall which eventually forced me to move beyond brute force and negligence. We’ve already made a significant dent in this, even in the first few months of working with Sacha. We’ve set up a whole new suite of tools to help us work together. Amazingly email is no longer a source of anxiety for me. My dream of implementing surge pricing on my inbox is a step closer. I’m genuinely invigorated and excited to think about what will be possible once we really hit our straps.

A part of the urgency to make this change was driven by our plans to shake things up in 2016, in a way that just wouldn’t have been possible previously. We are taking our kids out of school for the year and in a couple of weeks we hit the road, with plans to visit all seven continents. I have no desire to broadcast or live stream it, but if you’d like to follow along we’ll post occasional updates here. It promises to be an amazing adventure. I can’t wait.

Auf Wiedersehen

This is the final annual report, and likely the final post full stop on this site, at least in the current format.

I started writing these annual summaries in 2008, when I was in a very different place. Reading back over the full set it’s interesting to spot the things which are constant and the things which are nearly unrecognisable with the benefit of time and distance.

Once upon a time this blog was a place where I would post most days. That activity, including all of the conversation which used to happen in the comments has in recent years switched almost entirely to Twitter, for better or worse. What’s left is a smaller and smaller volume of posts of which I am more and more proud.

It’s become a bit of a joke amongst friends how often I reference back to old posts. It’s odd that a particular thought or idea should have a timestamp – both because to the extent that they are still valid and correct they shouldn’t seem dated, and to the extent that they are not they should be able to evolve (or be quietly deleted) rather than be frozen in perpetuity. So, it’s a relief to ditch the blog format and at some point I look forward to repurposing most of the recent content into something that will be more useful, more easily shared and hopefully more widely read.

Onwards and upwards.

Thank you. Take care. Talk soon.

Previous Annual Reports:

My Favourite Posts (from each of the last nine years):

More favourites

It’s funny how some distance makes everything seem small

Continuing my New Years Eve tradition, here are some favourite tweets from the year just been. Enjoy!

And some memorable retweets:

But, still nothing beats this one, from November 2014:


Previous Years:


Red Peak: Distinctly From New Zealand

What story will you tell?

We are the No. 8 wire nation. We believe we can do anything. This has some big upsides. It means we have more than our fair share of inventors and innovators. But, sadly, it also means we are sometimes far too slow to engage specialists who can help us take our good ideas and make them genuinely world class. In fact, we’re often suspicious of experts.

The whole process to select a new flag is yet another example of this. It’s crazy that the final four designs were selected by a panel that included a former All Black and a reality television producer but no designers. The result was actually predictable. They ignored expert advice and leaned heavily on popular opinion to make their selections. And with the final four choices they offered the country, they ended up offering little choice at all.

Design is a strange thing. We all have an opinion. But, for most of us it is difficult to explain why we like one design but not another. This is what makes experts, experts. They can explain!

For example, they can explain the difference between an emblem and a flag:


We have a world class emblem; earned and worn by our greatest. I’m extremely proud of it. Whatever happens in these referenda it will continue to be the symbol that we choose to represent ourselves. Like many people, I initially thought it would be an obvious inclusion on our new flag.

But, like most emblems, it’s a detailed shape, and therefore visually challenging to include on a flag. Even more so since it cannot use a simple fern without being too similar to trademarks such as the All Blacks logo. So any silver fern flag inevitably becomes compromised and complicated with multiple colours and a mixture of symbols.


A common criticism of Red Peak is that it is just a bunch of triangles and doesn’t scream “New Zealand”. This is true of the South African flag too. It’s also a simple geometric design, but one which we now instantly recognise as representing South Africa. Why is that? Of course there is a story, and all of the colours and shapes have meaning, but those details are really only important to South Africans. We don’t need to know the story to know this is their flag.

Red Peak has a wonderful story, referencing the mountains that literally define our country, and the Māori creation myth of Ranginui and Papatūānuku. It is a flag of two halves: one referencing the colours and designs of traditional tāniko and tukutuku panels, the other referencing the colour and shapes of the current flag. It’s strong, but it doesn’t shout. It’s humble but aspirational. It has the same qualities that define us as New Zealanders.

Red Peak

These stories have meaning and can be something we share with the world. But they are mostly for us. Others will come to know this design over time; as a result of the way we proudly fly the flag, wear it on our backpacks and paint it on our faces. Whether large (on the giant flag pole greeting tourists at Auckland airport) or tiny (next to an athlete’s name at the Olympics) Red Peak is a elegant and distinctive design that works.

When you come to rank the options in the upcoming referendum consider the overwhelming support the Red Peak design has among the experts. I don’t claim to be one of them, but having listened to their advice, I was convinced. We’re lucky that Red Peak was included as a fifth option. But, it’s still the underdog. It needs your support. Please vote, and rank Red Peak #1.

When people from around the world ask about our flag it would be great to have an amazing story to tell them. What story will you tell?

Level Up

“I wake up in the morning unsure of whether I want to savour the world or save the world. This makes it hard to plan the day.” — E.B. White

I was recently invited to travel to Israel as part of a delegation organised by Square Peg Capital and the Australian Israel Chamber of Commerce.

One of the people I met was Eitan Wertheimer, who sold his family business to Berkshire Hathaway in 2013 for $6.05 billion (that .05 is $50 million – when talking in billions even the second decimal point is material!) He spoke about the challenges of growing and selling the business. But, interestingly, he also talked frankly about how he struggled with what came next.

While our windfall from the Trade Me sale to Fairfax in 2006 was several orders of magnitude smaller, that resonated with me, as it similarly forced me to develop a whole new range of skills in short order: managing money, investments and philanthropy.

To date we’ve managed by a combination of brute force and negligence.

Ben Casnocha recently wrote about his experience working as Chief of Staff for Reid Hoffman. He talks about “The 40% Question” – i.e. if you think you’re working at 60% efficiency then what would it take to bridge the gap, and how would life be different if you did? That question is full of intrigue for me! And the rest of the article hinted at some of the answers.

Clearly the way we have been working doesn’t scale. It’s time to level up.

So, we’re delighted to announce that we have hired Sacha Judd as our new managing director, with effect from October this year, across our private investments, early-stage ventures and non-profit foundation.

Sacha has been a corporate and capital markets partner at Buddle Findlay for the past eight years, and has specialised in working with early-stage and high-growth technology companies. She is a significant contributor to the sector, through her work with events like Refactor, and her focus on educating and empowering founders.

We have worked together with Sacha on many of the ventures we have invested in, including Vend, Timely, Atomic and Revert, as well as co-hosting an annual Flounders’ Club retreat at our fabled Unicorn Farm, near Nelson.

I’m still in shock, frankly, that we were able to get somebody of her calibre to agree to do this job. I’m very excited about the possibilities that this creates for all of us.

You can now find us at hoku.nz. Stay tuned…!


I spent the last month more-or-less disconnected.

I’ve done this sort of thing before, but never for this long. It’s been a rare opportunity to take half a step back and think a bit about how I use technology, and consider some changes.

Disconnected in this context didn’t mean offline. I still had access to the internet. I still used the web to search, teach myself new things, book tickets and rent cars etc. I just made myself unavailable to inbound things that would take attention and went cold-turkey on some negative browsing habits.


It took me about a week to stop the tide on new messages, before I could put an out-of-office notification in place without interrupting anything mid-conversation. That, by itself, was pretty depressing. I went back into my inbox a couple of times during the month, to get in touch with people I was arranging to meet and also one time when delayed at an airport and the temptation to use the downtime productively was too great. But, otherwise, ignoring email was probably the easiest change to make.

I discovered that the badges that show a count of unread messages on the app icon and dock had at some time been re-enabled on both my laptop and my phone (presumably as part of operating system upgrades?) and that was triggering me to automatically check whenever I used my computer or phone for other reasons.

After a few days I didn’t give my inbox much more thought.

I did return to a large backlog, which will take a while to trawl through. It highlights how much noise I normally filter out using Triage (although it’s even easier to do it in one click). It’s slightly surprising how many of the threads are still relevant a few weeks later, although does show how little is as urgent as I otherwise treat it.

I realise it’s a privileged thing to be able to just say “nope, not looking” for as long as I did. Those I work with were very patient, which I appreciate. Towards the end I started getting a few txt messages from them suggesting I take a look at something urgent, but by then I wasn’t able to do much either way.

I really don’t enjoy the deteriorating relationship I have with my inbox. The anxiety it generates seems completely unnecessary. It got even worse in the second half of last year. After this clean break I’m keen to be much more strict about where and when I check for new messages and try and better batch my responses.


It’s a few years since we cancelled our newspaper subscriptions and stopped watching television news. Since then I’ve relied on online news sites. But, especially with Stuff and NZ Herald, I’m no longer convinced that I’m a customer of these services, rather than the product being sold by them to advertisers, and have found the signal-to-noise ratio to be getting lower and lower (with the exception of the celebrity gossip, of course). All it takes to lose confidence in the quality of what you’re reading is one story on a topic you know a lot about. You can extrapolate from there.

I need to be careful here since I’ve been warned by somebody whose opinion I respect (and normally follow) that the way I talk about this is boring. I’m not being superior. But, honestly, it was a relief to stop reading these sites, literally, first thing every morning. It’s hard to see myself re-establishing that habit.

I switched to using the Radio NZ Timeline to quickly scan the headlines, and went looking for more details on the rare occasion when that was warranted (e.g. following the Charlie Hebdo bombings) but otherwise don’t feel I missed anything.

No news is still good news.

Social Media

Lastly, I stopped using Twitter. This was hard. I knew I was a bit addicted, but didn’t realise quite how deep it ran. It didn’t help that I was doing cool things, and I constantly found myself wanting to broadcast the details.

I basically failed completely for the first week. I continued to reflexively check whenever using my phone or laptop, and, worse, when I was otherwise in the company of others. I aspire to be more Amish than that.

Even after I said goodbye and stopped tweeting I had classic withdrawal symptoms. I caught myself sending links to tweets I wanted to remember via email, rather than favouriting them, so that people wouldn’t be able to tell I was still secretly online.

I eventually got away, by deleting the account details from the apps, so I couldn’t easily check without having to login each time.

I discovered that there are basically three things I get from Twitter:

1. A place to brag.

It’s obviously important you know all about the great things that I’m doing and you are not (and vice versa), right? Otherwise how will we know who is winning?

Towards the end of the time away I dabbled with Facebook, as a substitute (the quantity of shameless bragging there is even greater than on Twitter, I found) but I just couldn’t get into it. It’s fun to share photos or videos and get comments or “likes” from people you haven’t seen in person for ages, but my problem is that the “friends” I have there are a slightly incomplete snapshot from about 2008, and I think I lack the enthusiasm at the moment to curate that list much better.

2. A place to talk shit.

It was a bit chilling to go back over a whole years worth of tweets and discover how many of them were just junk. Visiting the water cooler is fine, but somebody who spends all day there has no right to talk of being full.

I don’t think many of the just over 3000 people who follow me on Twitter will miss random tweeted song lyrics out of context, or silly arguments about incubators and accelerators, and I’ll find something much more useful and interesting to do with that time.

3. A source of interesting links.

I really missed this. As a result I started using Nuzzel, which aggregates links based on things tweeted by the people you follow, and found that in some ways even better than the real thing. I think this is going to fundamentally change the way I use “follows” on Twitter – in the past I’ve limited myself to 100 people, and generally had a bias for those I know in real life (i.e. Q: “would I stop on the street to talk to this person?”) but now I think I’m going to change that to preference those that share the most interesting things and people I aspire to maybe meet one day.


I have no idea how well these changes are going to stick.

As Andy Lark pointed out in his first post for the year:

“One of the downsides of working in tech isn’t just that you are surrounded by seriously distracted people, but you become one over time”

That’s dark. But accurate.

Maybe publishing about this reset makes me slightly less so?

Either way, if you can convince yourself to try it, I throughly recommend some disconnected time.


2014 Annual Report

“Beware the barrenness of a busy life.”
– Socrates

“Don’t say you’re busy. Say you’re getting lots done. If the latter isn’t true the former is irrelevant.”
— Not Socrates

I managed a whole year without using the word “busy” to describe how I was. It’s amazing how much more you can get done when you’re not constantly complaining about how busy you are!

What started so well, with a long relaxing break, mostly spent doing nothing of note, was quickly swallowed by a very full schedule. I don’t know how that looked from the outside, but from the inside trying to do a few too many things at once did eventually wear me down. Because the next thing was always hovering I didn’t always appreciate what I completed during the year, so hopefully writing all of this down helps to put that right…


My work in 2014 was nearly all LLB and bugger all BSc(CompSci).

At the top of the list, it was a huge year for Vend. Deja vu!

The early part was once again dominated by capital raising. It was very exciting to close a US$20m round in March. We are humbled to have the support of some great investors, and it was excellent to add Valar to that list this year.

With more fuel on board, we doubled the team. Again! In fact, we doubled just about all of the key numbers. There are now 12,000+ stores using Vend in over 100 countries around the world. We opened new offices in Toronto, Berlin, London and Wellington. We processed more than 60 million sales through the platform during the year. It’s really come a long way, and it still feels like we’re just getting started.

There were many opportunities to dress up and accept awards – Vend won the Emerging Company of the Year and the Exporter of the Year under $5m (for the last time!) at the Hi-Tech Awards in Christchurch in May, where we surely secured the homepage spot for another year with our official photograph; Vaughan won the Technology category at the EY Entrepreneur of the Year Awards in October; and we celebrated with a table full of women working in technology; and in November we picked up 4th place at the Deloitte Fast50, with 1097% growth.

I’m relishing my role as Chairman. I’m committed. I’m learning a lot.

It was also a year which saw Timely start to get a bit more attention. So much so that it’s already nostalgic to look back at my debut in the ODT in February.

Shortly after that we announced a $1.3m capital raise. The team has more than tripled since then, with people distributed around New Zealand (in Dunedin, Wellington & Auckland) and also in new sales offices in Melbourne and London. There are now over 2000 salons, clinics, trainers and many other small business customers using the Timely booking platform. During the year they took more than 5 million appointments!

I was upgraded from advisor to director in October. I’m excited to be involved.

It wasn’t such a great year to be a Xero shareholder, but I suppose I still need to mention that here having given myself credit for backing them early over the last couple of years, as they were on on the way up. I remain long.

I invested in three new companies during the year: Atomic, Revert and Respondly. It was exciting to see them start to talk about what they are working on. Expect to hear more from me about these in 2015. I have high hopes for all of them.

I’m increasingly proud of the ventures I’ve backed, and will continue to focus on investing in the best companies, not the most companies. Overall, the portfolio doesn’t owe me anything at this point, which is a privileged position.

Southgate Labs has been the foundation for a lot of this over the last four years. Investing in Vend was literally the first decision we made together. We always talked about the possibility that one of our ventures or products would suck us all in. In the end it turned out to be a few different ventures. So it goes. It’s been a fun team to be part of and I can’t wait to see what they do next.

However, prior to that, we did finally manage to launch Dr SaaS, which we’ve been using internally with the ventures we work with for a while. Hopefully I can get a few more companies using that next year.

I work with amazing people. That alone justifies my founder-centric approach. They all do things that I can’t or wouldn’t, and increasingly haven’t, which makes it a bit odd, at times, to be an advisor. Nonetheless I enjoy my part.


It was a great year of #sportsball. This started out as just a conscious attempt to get along to more live sport, which is something I love doing. But, it ended up taking on a life of its own. It was fun to see it embraced by a wide group of people, some of whom might have even surprised themselves.

I did see some great live world class sport: ASB Classic Tennis in Auckland, Black Caps Cricket v West Indies in Nelson, Speedway, Australian Open Tennis in Melbourne (where I was thrown a real live sports ball!), Black Caps Cricket v India in Wellington, A-League Football in Melbourne and also with the boys in Wellington and then Phoenix v West Ham in Auckland, Sevens in Wellington (more, more), Dragon Boats (more), AFL on Anzac Day in Wellington, Super 15 Rugby in Wellington and then All Blacks v England enjoyed with some old friends in Dunedin (although my choice of wardrobe had me sticking out a little) and even MLB Baseball in Toronto. Thanks to everybody who came along and enjoyed these with me.

Where I couldn’t get there in person, I soaked it up on the big screen, and there was a lot to take in during the year: the Winter Olympics, the Masters, the Football World Cup, the Commonwealth Games, the FA Cup (although the crowd didn’t exactly go wild for Arsenal), the US Open Tennis, and the Baseball World Series.

Of course, there is a lot more to #sportsball than sitting and watching…

In February a combined Vend/Southgate (+ some ring-ins) team ran around Lake Taupo, finishing the relay in 14h 3s (3 seconds, grrr!)

In March I ran the X-Race with my oldest son (an event at the intersection of endurance running and Lego which was great fun – we’re looking forward to the 2015 edition) and also ran the length of the Abel Tasman track with my brother, over two days (it was worth every kilometre just for this great photo).

And lots more: Skiing in Nelson Lakes, Queenstown, Wanaka (including a great day cross country at Snow Farm), Table Tennis in Toronto, Tennis in Wellington, Golf in Otaki, Ice Skating in Wellington, Mountain Biking up and down at Kaiteriteri and just down at Rameka, a couple of Sea Swims, Putt Putt in a few different places, including Picton and Paraparaumu (I honestly cannot recommend the latter to you unless very hung over), Pheasant Shooting with Rathmoy in Te Para, Rangitikei (there was some debate about whether this qualified as #sportsball, but we eventually settled on #sportsbang), and Sailing on San Francisco bay.

Towards the end of the year I got a bit more serious about training. I ran a new personal best time of 21m 22s for 5km in Wellington in August, more than 2 minutes faster than I’d previously run, thanks to some great pacing from Nick. And in December I ran The Goat from Whakapapa to Ohakune in 3h 11m.

Thanks to all of that I finished the year fit and weighing less than I started for the first time in a couple of years, which feels good.

We’ve enjoyed some good family holidays. Before Christmas we rode with a big group from Mt Cook to Omarama on the new Alps2Ocean Cycle Trail. We spent a great week on Hamilton Island with a different big group. And we end the year skiing in Whistler in Canada.

I spent a lot of time playing and listening to music, and in January we finally got along to our first (and last?) Big Day Out.

I also logged 104 movies. I don’t read much fiction, but I do watch it.


We purchased the rest of a tennis court, burnt down one old house and made plans to build another. If only we were brave enough to film it, our ongoing project would make an epic episode of Grand Designs.

I installed iBeacons and tinkered with ambient status lights. It is quite fun living in the future, when I’m there.

Sadly few of the things above happened in Nelson, so doing so much meant a lot of time I wasn’t. According to TripIt I was away for 186 days during the year, which is an inauspicious new record. Just adding up the time I spent on planes and at airports represents a pretty significant opportunity cost.

Looking forward to 2015, I don’t think my schedule has ever been so well planned so far in advance. It’s definitely going to be another interesting one.

Beyond that, this is, I think, the penultimate annual report. Life goes on, but perhaps gets documented slightly differently. I still struggle to answer the “what do you do?” question that triggered this whole series of posts, but for entirely different reasons now.

Of course, there are pros and cons to a “full” life too. The pendulum swings back and forth. My new definition of luxury would be not feeling rushed.

Next year, I resolve, there will be more slack.


Previous Annual Reports:

An odd little distorting sliver

As has become the New Years Eve tradition here, some 140-char musings I’d like to remember, selected from a total of 3,204 tweets from the last 12 months.

I remain confused about the payback for the 2,995 people who choose to follow, to be honest. Mostly it was song lyrics (old and older), or ranting about accelerators and reality television. C’est la vie.


And, while I’m at it, some of my favourites from others from the last year:

I’m @rowansimpson on Twitter, if you would like to join the conversation.

The Quiet Ones

In 1997 Apple launched a new advertising slogan: Think Different, celebrating the crazy ones like Picasso, Gandhi, Einstein and others. In hindsight this may have been the turning point, as they recovered from being lost and near bankruptcy to become one of the largest and most iconic companies in the world.

In 2010 Derek Sivers gave a great short TED talk, called How To Start A Movement, about the importance of first followers. As somebody who has never really started anything of note, but has been lucky enough to be an early follower a few times now, I was encouraged and inspired.

This is my juxtaposition of the two: Here’s To The Quiet Ones

Please share this, using the hashtag: #QuietOnes

These are the people featured in the video, many of whom are my heroes:

This is the text of the voiceover:

Here’s to the quiet ones.

The co-founders, the assistants, the collaborators.

The round pegs in the round holes.

The ones who see things as they are.

They work behind the scenes, helping the crazy ones with their rough edges.

You can overlook them, disregard them, trivialise or underestimate them.

But as you ignore them they quietly get on and change things.

They push the human race forward.

And while some may see them as the quiet ones,

We see genius.

Because they are the people that know that what matters most is what you achieve,

Not who gets the credit.


Fine Words

All That Glitters

Tweet storms are fun, but I do miss blog posts. :-)

The Dark Net

NZVIF have released their latest Young Company Finance report. The report includes a list of all of the companies that raised new capital so far in 2014. It is an appallingly incomplete list. These are the companies that I know of they have missed:

I’m sure there are many others. Please add a comment to this post if you can give me more names. If you add up the amount raised by just those I’ve listed it comes to more than the $23m that is reported, meaning they miscalculate the amount of investment by at least half. No wonder officials are convinced there is a shortage of capital. They are overlooking all of the best companies who typically don’t need to resort to angel networks to raise money. This was the report on Stuff this morning: Angels give tech start-ups a good shot.

Investment in young companies by Dragons’ Den style investors topped $50 million in the year to June, according to a report by the New Zealand Venture Investment Fund (NZVIF) and the Angel Association.

Angels and Dragons, y’all. Apparently when it comes to young companies calling yourself simply an investor isn’t sexy enough. Just a thought, but maybe we should make it more about the companies and less about the investors.

UPDATED: added a few more companies and some links to media stories about these capital raises – in most cases this information is already in the public domain.

Full on Keynes

Here are three possible explanations for why we all feel so busy:

  1. We all spend too much precious time telling each other how busy we are, as if it were something to be proud of. (ref: this blog post)
  2. We all mistakenly believe we can have it all. And multitask. (we massively underestimate the switching costs)
  3. Men, of course! (at least according to this recent book review in the New Yorker – it’s unclear, as a man, who I should blame, but maybe I just need to lean in more, I don’t know?)

By the way, Keynes’ prediction was actually right, in my opinion: most of us struggle to do three hours of productive work per day. How else would we find the time for so much reality television otherwise?

As an experiment I’ve been trying to stop using the negative versions of the words we use to describe our activity, when we are unconsciously sympathising with each other: busy, stretched, slammed, etc. There are alternatives which are much more positive: full (as in full of interesting and awesome things), focussed, engaged.

Of course, using those words to describe your day does force you to consider how accurate they are as a description, and if not, maybe think again about how excited you are to be “busy”.

Give it a try.

Related Posts:


2013 Annual Report


Never has a full year report been more accurately named. I tried to squeeze a lot in.

There were lots of exhausting but invigorating adventures…

I completed three of the Great Walks, without putting on tramping boots. We paddled the Whanganui River in the rain in January, I rode both the Queen Charlotte and Heaphy Tracks during winter, and then in September I ran the Abel Tasman Coastal Track (in 4h 44m).

I was a regular visitor to the Kaiteriteri MTB park and also completed a couple of rides over the Copper Mine track. I managed one night ride, and look forward to more next winter.

In spring I took our oldest on his first overnight tramp – from Caanan to Castle Rocks Hut on the Abel Tasman Inland Track via Moa Park.

We visited friends in Boulder Colorado and while there walked to the continental divide at the Rocky Mountain National Park.

There were also some less wet and muddy trips…

I spent two weeks in Singapore, on a return visit to the Joyful Frog Digital Incubator.

In Autumn, we spent a week in a camper van trip through central Otago, including my first trip over the Lindis Pass.

We soaked up some heat in Bali in July and I enjoyed some time in the snow (both cross-county and downhill varieties) in Queenstown in August.

We were delighted to attend a couple of family weddings – Josie & Lo in Stinson Beach California and Cam & Michelle in Auckland.

I saw some live sport, including both the All Blacks (v Australia) and the All Whites (v Mexico) in Wellington.

But without question the highlight was the Americas Cup in San Francisco in September (unfortunately we couldn’t stay for the whole thing, but left feeling pretty confident about the outcome, with the score at 4-1).

There was no shortage of work either…

It was my first full year on the Powershop board. I’m learning a lot.

I spent quite a bit of time in Wellington with the team at Southgate.

Early in the year we launched Triage. The critical response to that was overwhelming and flattering and unexpected. We briefly topped the productivity category and were featured in the US app store during the first week. However, we discovered in the process that financial success doesn’t necessarily follow from that any more. It was, in the first instance, a selfish project and it’s still the first app I use every morning.

We worked with Glen on Company Box, and later in the year we launched Rabble. We continue our search for the next big thing.

It was also a huge year for Vend.

We worked hard during the first part of the year to raise additional capital to continue to fuel our growth. In the course of just a few days in May it was exciting to announce the successful completion of that $8m round, welcoming some awesome new investors into the mix as part of that, and then to be recognised at the Hi-Tech Awards dinner in Auckland where we picked up awards for both Innovative Hi-Tech Service Product and the Hi-Tech Exporter of the Year (under $5M revenues)

Startups are squiggly, and unfortunately people mostly only tend to talk about the clean and easy bits. Vend is no different. Over the last year we’ve more than doubled the size of the team and the business has grown even faster. That creates some chewy challenges for those of us lucky enough to be working on it. It’s been excellent to be part of the story so far. Stand by for what we have planned for 2014!

In June I made a new investment, in Timely, and have enjoyed working with them too as they have started to build their team and hit their straps. I have high hopes.

It was an unbelievable year for Xero, which masks a bunch of other poorer decisions when you look further down the list of companies I’ve invested in over the last few years. It already seems nostalgic to look back on old tweets celebrating the day it passed a $1B valuation, way back in March.

I enjoyed Webstock in February, where I also MC’d at the Startup Alley and got to chat on stage with Derek Sivers.

As I look around there are no shortage of opportunities. It’s definitely an exciting time to be involved in early-stage technology companies in New Zealand.

I spent way too much time in my inbox. I received 13,653 messages and sent just over 6,000. That’s about the same volume as for the last few years, but having eliminated nearly all of the noise it subjectively felt like more of these required consideration than in the past. Even if I assume just one minute per message that still accounts for over five and a half full working weeks.

tweeted, probably more than I should have. And blogged, much less than I could have.

I spent 168 days away from home (taking 95 flights, visiting 20 cities in 6 countries and travelling over 82,000km, according to TripIt). That’s nearly half again more than the 113 days away I reported just two years ago, which I already thought was too many then. Not all of that was work, but I doubt that distinction matters to a 9 year old and 6 year old.

And, even when I was at home, there was always a lot going on there too…

We finally officially warmed our new house in March, complete with jenga, fireworks and feijoas. The lasting legacy of that weekend is a new haircut (inspired by Andre Agassi) and a street sign (inspired by a flippant comment on twitter).

I kept mostly fit and healthy. It’s now four years since I first dipped under 80kg and I haven’t been back since. But this is the third year in a row that I’ve ended slightly heavier than I started, so it would be nice to break that trend in the coming year.

There was some downtime, including a disconnected week in June. But, not nearly enough.

I started the year aspiring to focus, and failed miserably. All of the things listed above combined to mean I spent big chunks of the year red lining, feeling more anxious than vital.

I did a little experiment during the year – giving myself five points every day (roughly equivalent to one point for every three hours awake) as a way to track how I was actually spending my time. It made for some slightly uncomfortable pauses when I was asked what I was up to – I knew exactly, but didn’t always want to admit it. Various work commitments soaked up just over 800 of the 1820 points for the year (~44%), which is difficult to justify in retrospect. I did manage to carve out a decent chunk of time for myself (~16%) and family and friends (~28%), although both of those were significantly lower in the first part of the year (thanks, Observer Effect!)

Perhaps in 2014 I’ll be a bit more selfish?

Previous Annual Reports:

Much Ado About Nothing

For my own record, some tweets worth keeping from 2013: