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 Stay tuned…!

Anything vs Everything

We’ve been brought up to believe we can do anything. It’s a powerful and important message. But, many of us have mistakenly interpreted that to mean we can do everything.

We want to have our cake, get lots of likes on the photo of our cake, eat it, and still have visible ribs.

It’s just not possible. We must choose.

Four loosely related examples…

I Wanna Hold Your Other Hand

In 1964 The Beatles played a long series of concerts at the Olympia Theatre in Paris. Eighteen days straight. Two or sometimes even three shows per night.

At the same time they were preparing for the filming of their first movie and were under pressure from their record label to come up with a new single to follow “I Want to Hold Your Hand” which had just reached number one in the US.

John Lennon arranged for a piano to be placed in their hotel room, so they could use the small amount of free time they had to work on some new songs. Somehow amongst all of that Paul McCartney composed their next hit “Can’t Buy Me Love”.

It’s remarkable they were able to create something so iconic under that sort of pressure and with those sort of constraints.

It’s easy to feel overwhelmed by the commitments you have and hard to focus on the things you know are important. And yet, most of us constantly soak, and often drown, in Twitter and Facebook. And blog posts about busyness. It’s useful to be reminded that it’s possible to do so much more.

Stories like this make me wonder: what other things did they not do in order to focus on the things we remember?

All The Things You Didn’t Do

It’s very difficult to assess opportunity cost.

For example, as Vend continues to grow I’m increasingly proud of the contribution I’ve made to the success so far. Of course, I rarely, if ever, take much time to think of the many opportunities that I’ve missed or passed on by deciding to focus on that.

Time and energy are precious things. Much more so than capital. Spread too thinly across multiple things they barely make a dent.

For those working on early-stage ventures there is a long long list of external distractions: networking events, panel discussions, meet-ups, pitch fests, fail cons, dragons’ dens, mentoring events, demo days, and coffee meetings. Endless opportunities for you to preach to others about the success you haven’t achieved yet or agree with each other about how hard it all is.

Perhaps even more important are the internal distractions. As soon as you have customers you have customer feedback which inevitably tries to drag you in a number of often contradictory directions. As soon as you have a market an adjacent market will reveal itself, if only you make one small change to the product (all product changes are small, right? just a SQL query!) or go-to-market.

But, you don’t have to design a product for everybody, as long as there is a big enough group of anybodies who will find it very appealing and you have a good way to reach those people and make them aware that you’ve solved a problem that they specifically have.

It takes conviction to have confidence about the bird already in the hand, or at least within sight. It’s hard to fight the fear of missing out. But it’s important. Otherwise you are “beating yourself up for being unable to count to infinity”.

This vs That

A friend once told me that it’s boring and selfish to be so focussed. She’s probably right.

It might seem boring to focus, when there are so many interesting things to be distracted by. Of all the people I know, it’s only the ones I most admire who think that focus is important. We are generally quick to forgive the selfishness of successful people, I’ve noticed.

I was recently asked to talk about my failures. It’s a good question and I gave an unprepared answer at the time about the long list of things that I’ve done which were not successful and the various ways that I’ve fallen short of what I wanted to achieve. Understanding these is probably more useful than listening to the stories about the unrepeatable successes.

Interestingly, Warren Buffett, possibly the most successful investor of all time, says his biggest mistakes are mistakes of omission – i.e. the bigger regret is not the things he did which turned out badly, but the things he didn’t do which could have been amazing. The retrospective in the 2014 letter to shareholders gives a few billion dollar examples.

This story re-told by Buffett’s personal pilot (!), which may or may not be true, provides a useful method for helping to determine your priorities:

1. List your top twenty-five priorities
2. Circle the top five – these are the priorities to focus on

(If you’d like to use this method for yourself, stop here and complete these first two steps before going onto the final step)

3. Highlight the other twenty – this is your do not do list

As James Clear says in the post I linked to above:

“Items 6 through 25 on your list are things you care about. They are important to you. It is very easy to justify spending your time on them. But when you compare them to your top 5 goals, these items are distractions. Spending time on secondary priorities is the reason you have 20 half-finished projects instead of 5 completed ones.”

What are your five? What are your twenty?

Getting Ahead

It was recently reported that only 19% of senior management roles in NZ are held by women. And 37% of businesses don’t have any women in these roles.

One of the common explanations for this is the fact that more women take time out from their careers to focus on family or community responsibilities.

Of course there is much, much more which must be done to make it easier for those people who do take time out for family or community to return to work and find this balance, and the full report details many of these.

But I think there is something even more fundamental that we’re missing.

The idea that anybody, man or woman, can take time out from their career, and then pick it up later as if they hadn’t is just wishful thinking. There is an opportunity cost. You have to choose.

You probably can’t do it all, have it all, be it all.

Lean in too far and you fall on your face.

As it says in the report:

“Many of the women we spoke to say they could not have reached the level they have without their partner making sacrifices.”

I expect that all of those people currently in senior positions have made some significant compromises in terms of their contribution to their family and their community. It would be remarkable if they hadn’t.

Perhaps part of the solution, if we want a better gender balance in this particular area, is to do more to acknowledge the value of those who choose to focus on the other areas, so they are not seen as less important or second class choices.

Eyes Wide Open

It’s wonderful to think that you can do anything. Please don’t let anybody tell you otherwise.

But don’t fall into the trap of thinking that you can do everything. At least not if you aspire to do anything well.

You have to choose what you’re going to focus on, and then have the conviction to say no to other lower priority things. And every time you do that there is an opportunity cost.

So best make them conscious choices.

Photo Credit: Beatles, Backstage Paris, 1965

Most People

This is based on a talk I gave at the end of last year to the prefects at my old school, Rongotai College. I really enjoyed meeting them and hearing a bit about how they think, and would be keen to do this again, if there is an opportunity. Let me know if you’d like me to give a similar talk to a group at your school.

The Definition of Success

Peter Thiel was one of the founders of PayPal and after that the original investor in Facebook, not to mention an investor in some local companies such as Xero and Vend. When he is interviewing people, for a job or potential investment, one of the questions he apparently asks them is1:

“What is something you believe that nearly no one else does?”

It’s a good question. Most people, I expect, can’t answer it.

I don’t want to give you the same old empty advice that I remember getting when I was sitting where you are, not that long ago2: work hard, do your best, follow your passion, yada, yada.

Instead, I thought it would be more interesting to talk a bit about some of the things I believe which most people don’t, and think about how you can use those things to help you be more successful in your lives.

This is an important thing to realise:

When you are at school, success is measured by how well do can do things that people have done before. That’s important. You’re building a foundation for yourself by understanding all of the things that others have discovered and learned.

But, once you leave school, it’s the exact opposite: success is measured by how well you can do things which nobody has done before and, what’s more, which most people don’t think you can do.

By definition, to be successful you just have to do those things which most people don’t. Think about that…!

Here are five specific things which I think most people don’t agree with, or perhaps just don’t think about long enough to realise.

1. Everything was made by somebody

Most people, especially as they get older, are not curious about how things are made and how things work.

Most people assume the world is just the way it is, and that their job is to live inside that world3.

However, actually, everything was made by somebody – the places where we live and work, buildings, shops and offices; the vehicles we get around in, cars and bikes and planes; our public spaces, streets, bridges, parks; the clothes and shoes we wear; the sports we play and even the teams we support; the devices that power our lives, computers, phones, software (not to mention the power stations and electricity network that make it all possible); all of the things which entertain us, television shows and movies, art, music, theatre; even the companies, organisations and institutions that make up our communities, with their rules and traditions and processes.

Don’t assume that the people who made any of these things are any different from you or that you couldn’t find some ways to make improvements if you’re so inclined.

When I was younger I used to enjoy taking things apart to see what was inside. One time I dismantled our VCR4. It’s easy to assume that the electrical things we use everyday, and increasingly depend upon, are a bit magical, you put a tape in and a movie plays on the television. But, once you take off the cover you realise that actually this is an object that has been designed by somebody and that a lot of thought has gone into it – for example I discovered that the head which reads the signal off the tape was oriented on a strange angle, so that the width of the tape could be keep smaller.

Likewise, when I get the chance to watch the All Blacks play live, I try and get to the ground early to watch the players go through their pre-match routines. I focus on one player at a time and see the various drills they complete. It’s easy to assume they are untouchable gladiators, but actually they are just skilful individuals5, preparing methodically, and together with their coaches they have thought about how they want to play as a team. They are following a well considered plan.

Once you understand this about the world, you realise something important: you can change it, influence it, improve it, and build your own things that others can use to make their own lives better.

So, be discontent. Look out especially for things that make you angry or frustrated. Don’t just accept things the way they are. Ask yourself, who made them? Why are they made that way? And, what could you do differently to make those things better?

2. Be prepared to be wrong

Most people don’t take risks, because they worry about what other people will think if they fail.

I’m not saying you should be happy to fail. I think a healthy fear of failure is a great motivator to do the hard work you’ll inevitably have to do if you aspire to do anything interesting. If you do fail, it will hurt, and so it should – go and feel terrible for a bit, then remind yourself that you’re not most people.

(Some people think that we should be more tolerant of failure in New Zealand. Sometimes you hear people suggesting that we should celebrate failure like they do in the US. Interestingly, not very many of the people who say that are as excited when I suggest that quid-pro-quo we should also celebrate success like they do in the US. Vive la inequality!)

I am saying you shouldn’t be scared to try.

Most people are generally optimistic, so their thinking tends to be mostly wishful thinking.

The important thing is not to be scared of taking risks, it is to better understand the risks you are taking. Try anything, provided you have a plan for getting back on your feet if/when you do fall on your face.

After I left school I went to university and worked hard and got a good degree. After I graduated I got a good job at a good company with good prospects for a good career. And then, after a few years of that, I quit to try my own venture. At the time, most of the people who knew me thought I was mad, and that I was throwing my career away6. They were probably right to think that – there was a very slim chance that what I was doing would be successful and a much greater chance that it would be a complete flop.

As it was, I wasn’t actually really risking much, other than my pride. If it didn’t work, I could have always gone back to a suit-and-tie job working for somebody else7. But, given what happened, it would have been a much greater failure not to have tried just in order to not seem a bit crazy to people who didn’t understand that.

So, don’t spend too much time agonising about what other people think. Especially those who are lot older than you, like me! With age comes experience, and with experience comes an understanding of all of the reasons why something is impossible, as well as a much greater fear of falling.

(And for good reason: when you are a kid you fall on your face multiple times a day and it doesn’t make much difference, but by the time you are an old person a fall can literally be life threatening, so it’s worth constantly assessing where you are on that spectrum!)

There is a caveat to this, which is that most people who make things are terrified of criticism, so they generally prefer to keep the new things they are working on secret until some mythical point in the future where the thing is finished and perfect. This is nearly always a mistake. As Elon Musk says, better to take the view that you are wrong and that your job is to be less wrong and the best way to do that is by asking for considered feedback from anybody who will give it to you, but especially from your friends who know you well, and will give you an honest opinion.

By the same measure, don’t spend too much time judging other people for the risks they take. It’s a foolish thing to predict somebody else will fail anyway, as if you’re right then you look mean and if you’re wrong you look silly, so you lose no matter what happens.

3. Ask for forgiveness not permission

Most people think they need to qualify, in some way, before doing the things they’re interested in and passionate about.

As you decide what to study at university you’ll learn about pre-requisites. That is, somebody else will decide what things you need to have done first in order to qualify for the things you want to do next.

This is how it works on reality television too. If you want to be a “pop idol” or “master chef” the way to do this is to wait for the auditions for the show to come to your town, then line up with all of the other hopefuls, compete in some contrived challenges and have your fate decided by some random celebrity who will give you the thumbs up or thumbs down, followed by either 15 minutes of fame or shame.

(Of course if you want to be a real pop idol or master chef, without the double quotes, then probably best to avoid the televised audition – do the hard yards in the relative anonymity of the shadows).

It’s easy to fall into the trap of thinking that the whole world is like this, and to continue with that mindset once you leave school. But, reality television isn’t real. If you want to do anything interesting you nearly always have to work it all out for yourself.

This is not to say you should ignore the experience of those who have gone before you. You should learn as much as you can about the things they did right, and wrong. Just don’t wait for them to open the door for you.

It’s worth constantly asking yourself: what or who are you waiting for?

If it’s not clear then often the best option is to just press on and do what seems like the logical next step to you, based on what you’ve learned so far. If you’re wrong then you may find yourself having to apologise to the owners of the toes you’ve stepped on, but that’s nearly always better than leaving yourself to wonder what could have been.

Most people think they need to work for somebody else.

Luckily, not everybody, or else there would be no jobs.

Of course, to start with you almost certainly will work for somebody else.

Try to treat them as a “we” rather than a “they”. Your boss was in your position once, probably not that long ago. Aim to become what they are, and get them to help you with that, rather than spending your life being suspicious and resentful.

On the other hand, don’t put them on a pedestal. They are likely unsure about a lot of things too, and will need your help. That’s why they’ve hired you, right?

When I work with early-stage companies, I always encourage the founders to hire people smarter than them who could, if things go well, eventually do their job. Because, when everybody hires their replacement that enables them to take on more responsibility at the next level up. That’s how you grow a great team. A’s hire A’s. But it’s a scary thought for most people. B’s hire C’s.

4. Who is telling the story?

Most people mindlessly believe what they see on television and read in the media.

Always ask yourself: who is telling the story, and why? It’s okay to be suspicious. Think about what that person or group is trying to sell you, or how they might benefit from having you believe one thing or another.

You should learn about the different types of bias that can confuse or distort how stories are presented.

For example, history is normally written by the winners. The reason I get to talk to you today is because the things I’ve worked on have mostly been successful. You don’t get to hear from the many others who tried similar things and didn’t have the same result, even though you would probably actually learn a lot more from them than you can from me.

You should seek out media coverage of a topic that you know well. You’ll most likely find that it’s confused and shallow, if not inaccurate and misleading. Then, extrapolate from that and consider what this means about all of the other areas where you are not knowledgable and therefore take what is reported at face value.

You should look for repeating patterns.

One of my guilty pleasures is seeing how the media cover large Lotto jackpots. It’s the same stories repeated every single time: the buzz of anticipation as the prize pool grows; the excitement of the “lucky” outlet that has beaten the odds and sold the winning ticket; and finally the winner, once identified, will inevitably tell journalists about all of the things they are going to spend their windfall on, while at the same time wanting to remain anonymous and/or continue with their existing life.

Interestingly, we never hear from the unlucky losers.

We soak in this sort of high-calorie/low-nutrition news constantly, and hopefully (from the perspective of the people selling us the stories) also notice the advertisements which are sold around them.

You should try to avoid confusing famous and successful. Those that make the most noise about their achievements aren’t always the only ones who are most deserving of your respect or attention. It’s good to have heros and role models to compare yourself to, but be careful who you choose. Try not to compare your inside with anybody else’s outside. Chances are you don’t have to dig too deep in order to find some major flaws or shades of grey.

And, don’t forget that everybody spins their story. I’m doing it right now! Few things are as simple, or obvious or absolute as they are often presented.

5. Choose your friends

Last but not least…

Most people don’t realise the influence that their friends and colleagues have on their life.

We all normalise our behaviour. We reasonably quickly become the average of the people we spent the most time with. If you hang around with people who behave a certain way, odds are that you will behave that way too, for better or for worse (unfortunately this seems to be true for negative behaviours just as much as for positive behaviours). So, it’s important that you choose those people carefully.

You can use this to help you change something about yourself that you want to change. If you want to be fit and healthy, choose friends who are fit and healthy. If you want to stop smoking, stop spending time with people who smoke. If you want a better balance between work time and family time, find people to work with who already organise themselves this way. Likewise, if you want to really push yourself in your career it will be much easier in a company where your colleagues are doing the same.

At the same time, work hard to keep in touch with the friends you’ve made here at school, because you’re probably not going to have the same opportunity again. It may seem to you now like that will be easy. At the moment you all have a lot in common. More than you realise. But, once you leave you’ll find your lives diverge quite quickly. Some of you will go to university, and study different things. Some of you will get jobs. You’ll find yourselves in different places around the country and around the world. Some of you will have a family. Some of you won’t. But, either way, all of you will get older, and when as you do it’s worth remembering those who knew you before you were any of those things. They are the ones who will keep you honest.


Think about the definition of success. You don’t have to be most people if you don’t want to be. You just have to ask yourself: what is it you believe that nobody else does?

Thanks for listening8, and good luck!


  1. Peter was asked this question himself in an AMA on Reddit and his answer was: “Most people believe that capitalism and competition are synonyms, and I think they are opposites”
  2. *cough* 20 years ago!
  3. This is not an original observation, and not even an original wording. I’m directly quoting Steve Jobs from this video:
  4. At this point in the talk I segue into a brief history lesson, to explain what a VCR is, but assuming the audience for this blog post is a bit older than at the school, I’ll skip that here and just provide a link to Wikipedia.
  5. As Brendon Radcliffe (founder of says, the All Blacks are executing the same skills as any other rugby player: tackling, passing, kicking, running. They just need to do it instinctively, under extreme pressure of time and space.
  6. Interestingly, there was only one person who was brave enough to say this to my face at the time – the managing partner at the company who had hired me, and he may have just been saying that in his own self-interest, hoping that I’d change my mind. It turns out that there is also some risk telling somebody that they are throwing their career away, as they may turn out to be making a fantastic decision which will make you look a bit silly down the track.
  7. Actually, that almost never happens, because in the course of trying something new you change, and so the thing you want to do next is something different, even if you fail.
  8. As Mary Schmich says in her famous fake valedictory speech: “Advice is a form of nostalgia. Dispensing it is a way of fishing the past from the disposal, wiping it off, painting over the ugly parts and recycling it for more than it’s worth.”


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.