After five years as a director at Vend, yesterday was my final meeting.

I’ve written here about a number of milestones in the Vend journey to date: from the bike ride where I first got the pitch, the announcement of our first investment round, Vaughan describing the early history in his own words, notes from our recent visits to San Francisco, watching the team expand, and more recently the search for a “real” board.

So, I thought one final post would be appropriate.

It’s been a privilege to be part of the team from the beginning. It doesn’t feel like that long ago we were putting together cheeky advertisements and videos and hoping that people would notice.

A billboard concept. Probably better this never saw the light of day…

POS Advert

Steve, the potty mouthed, bigoted and small minded, crappy old 1980s cash register, finally meets his fate…

An early recruitment video…

Thankfully, people did notice. Suddenly we had retailers from all around the world using our software to run their business. And more and more of them over time!

As the team expanded, it was great to be able to spend some time in Auckland, Melbourne, San Francisco and Toronto with the local people who are working hard to make Vend a success.

We have also been joined along the way by some of the very best SaaS investors – from here in New Zealand and from Germany, Australia and the United States.

When you look back on this sort of thing it always seems like time is short. So, it’s easy, generally, to be motivated by negative FOMO – the fear of missing out. But, in this case, my overwhelming memory will be TOBI – the thrill of being involved. Thanks to Vaughan and the team for having me along for the ride so far. And, especially to Miki, Barry and (too briefly) Claudia and Sarah for your support as part of the board over the last couple of years.

Vend is in an exciting period as the team works to put the business on the right track for the next phase of growth. To everybody involved now, I remain an enthusiastic investor and will watch with interest to see where you can take it from here. You have a huge opportunity to be part of something special, and I know you’ll make the most of it!

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?

I ❤️ the Silver Fern

Dear John,

It seems my last letter struck a chord with many.

I didn’t set out to advance a movement. I wasn’t even the first to write about the Red Peak flag after the current shortlist was announced. I was simply expressing my disappointment at the options. There seemed to be no choice.

We were promised four choices for the first referendum, but in the end have been presented with a single solution – four variations of a fern.

Here is something that might surprise you … just like you and lots of others, I love the Silver Fern.

It’s an enduring and unique symbol. It’s widely associated with New Zealand and New Zealanders, and is the only symbol most of us would pick if we had to choose a single icon to represent our country. It is something we should all be proud of.

It is most commonly associated with our sports teams and specifically with the All Blacks. But, of course, it goes much wider than that. It’s extensively used, in business and trade, tourism, on our money and our passports, and importantly on the headstones that commemorate our fallen soldiers.

For these reasons I’ve long been an advocate for a Silver Fern flag. I was pleased to see a simple Silver Fern on Black design included in the long list.

But, as we now all know, there are a number of reasons why that sort of simple Silver Fern couldn’t be considered for selection – most importantly that it is almost impossible to design a flag featuring a fern that doesn’t look like one of the many other existing trademarked designs.

Of course, the Silver Fern is not part of our current flag, and whether it’s included in the design of the new flag or not, it will still to be our national symbol. We will continue to use it everywhere we do today, and no doubt find even more uses for it in the future.

That’s not the question. The question is: what is the best design for the flag, given we can’t use the simple Silver Fern?

This is what first attracted me to the Red Peak design. As the designer Aaron Dustin explains on the Red Peak website:

The Red Peak flag was intended to be a ‘new’ symbol that expressed our NZ identity while avoiding the use of Southern Cross, koru, kiwi, and fern motifs.

In just a month, since the long list was announced, and especially in the last week, since the current shortlist was announced, this elegant and considered design has received an overwhelming amount of support, from a wide cross section of New Zealanders. Very few of those people were engaged in this process before, if we’re honest. They are now! This is the first sign that people actually do care about changing the existing flag. Let’s not waste that.

Because it uses an abstract geometric design, its symbolism is less obvious. It isn’t just a rehash of existing symbols to fit on a canvas. You need to take a bit of time to understand the meaning and story behind the shapes and the colours. It allows room for each person to add their own interpretation.


This is why it’s no surprise that when asked, based just on the shapes, it didn’t rank very highly in public polling. It’s like asking people to choose their favourite singer just based on a photo. But, it’s also why, once people were given the opportunity to consider it in context, it has resonated with so many and become their preferred option.

If you reduce many of the great flags to their shapes and colours they are also meaningless. The Japanese flag is just a red circle. The French flag (like a lot of other flags for that matter) is just three rectangles. The Union Jack is just some lines and triangles. The Stars & Stripes is … well stars and stripes. It is the story attached to these shapes and colours which give all of these flags great meaning. And, it’s the same with Red Peak.

The fact that, like them, Red Peak is a simple design, means that it stands strongly alongside all of these examples, and all of the other great flags. The same cannot be said for the other designs in the current shortlist.

Here is another wonderful thing if, like me, you love the Silver Fern on black: the Red Peak design stands strongly alongside the Silver Fern too. It complements. It makes it look better. Again, unfortunately, the same cannot be said for the other contenders, which compete for attention.


So, it’s disappointing that the current short list doesn’t include the Red Peak option. It would be great to have the choice, and to leverage all of the engagement and support for replacing the current flag which has been generated in the last week.

However, it’s not too late. It would be really easy to make this change. Even more so, because the current shortlist includes those two identical designs. All Cabinet needs to do is to pick one of those and replace the other with this Red Peak design by Order in Council on Monday. You can do this. Then we can have a process which includes real choice.

That would be choice, eh!

So, John. I ask again, respectfully: why not give New Zealanders a real choice?


Dear John


I’ve watched your video which describes the reasons you believe we should change the flag.

I am one of the many New Zealanders who strongly agree with you.

I know there are some who have dismissed this whole process as a waste of money and a distraction from other more important issues. I don’t agree with that. I believe we are all capable of doing more than one thing at a time and actually I believe the symbols we use to represent ourselves on the international stage are important and worthy of discussion.

It’s well publicised that your preference is for a design featuring the silver fern. The fern is a symbol we should all be proud of, and indeed my own submission to the design process was a simple silver fern design on a black background (what a shame that we let terrorists and pirates steal that option from us).

However, as shown by the English Rose, Scottish Thistle and South African Springbok & Protea (as well as many many others) it is possible to have a strong and widely recognised national symbol without necessarily having it represented on the national flag. Indeed all three of those countries have simple and distinctive flags which are also well loved and recognised. Whether our new flag includes a fern or not will not change at all the fact that we use and will continue to use the silver fern symbol almost ubiquitously, everywhere from rugby teams, to coins, to war graves.

During the process of public consultation I learned a lot about what makes a great flag design. I’ll admit prior to this I wasn’t familiar with the term “vexillology”. Presented with new information, I changed my opinion. There were a lot of very average designs proposed, but there were some great ones too, including this, which I now consider the best of the bunch:


The Red Peak, by Aaron Dustin

This is a considered and elegant design.

It has a story, referencing the Maori myth of Ranginui and Papatuanuku.

It cleverly combines two halves.

On the left a nod to tukutuku panels, with the traditional colours of black, red and white:


On the right a reference to the stars and Union Jack from the current flag:


It is designed to be a flag, with a single black panel in the critical top-left corner, which is prominent when the flag is hung.

It does not look out of place when displayed alongside other great flags, as will often be the case




(yeah, nah!)

It works large and, importantly, small:


It is also very simple to draw, even for somebody with no artistic skills:


I was pleased to see this included in the long list and was looking forward to making the case for why this should be selected as the new flag design in the referendum process.

So, I was saddened and disappointed to see the four designs which have been selected for the short list.

I know you want this to be a democratic process, but frankly, given those choices it feels like no choice at all, since three of the designs are so similar and two are identical except for substituted colours. At the moment it’s like being asked to choose between a Carl Jr, a Big Mac, a Whopper and … actually I don’t know the burger equivalent of the hypnoflag, so I’ll leave that to your imagination.

To win broad support, a challenger product or service needs to be remarkably better than the status quo (e.g. selling something on Trade Me vs using traditional newspaper classifieds). I worry that none of the options which have been put up will succeed on that basis. Even as a strong supporter for change, I don’t believe any of these four designs are good enough. But, worse, I worry that one of them will be preferred over the current flag anyway.

You have set this process up, and you (and probably you alone at this stage) have the ability to change it.

I ask you to reconsider the short list, to replace one of the two identical silver fern designs with Red Peak, and at least give us the option to choose.


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