Living Impossibly – My TEDx Experience

I recently had the opportunity to share a very personal story at TEDxAuckland. It’s a story of doing impossible things, and how my mother inspired me to do so. The experience doing this talk was one of the greatest experiences of my life. Mainly because I got to share the story, but also the amazing people I met along the way, the other speakers and the organisers. Rehearsing with the other speakers was intimate and fun. And on the day, the buzz of the event, and the mind filling stories on the day were exponentially more powerful when presented in front of a few thousand people.

Do something impossible, and if you get the opportunity to talk about it, do it. It is one of the best things you can do, especially if you are like me, scared shitless of talking to a room of people.

Be amazingly impossible.

UPDATE: Wow. I just realised it is 4 years TO THE DAY. Could not think of a more fitting way to remember it than sharing this. Funny world huh?

It’s ok I’m only busy for a while

This is a pretty typical view of my calendar, in fact this is next week and I haven’t even scheduled in all my catch ups and things to do yet. This is just the meeting requests! I also have to squeeze in things like “real work”. I consider this normal.

Only busy this week


The next week after, it looks identical. The week after similar but with a few holes. In fact if someone wants to catch up with me, my default response is:

“Oh man I am slammed for the next 2-3 weeks, but I am wide open after that so get in touch then”.

When Mel pulls me up on being home late constantly, or leaving home early, or not being able to schedule in family things my default response is:

“I’m sorry, I am slammed for the next couple of weeks, but look, here see, it’s ok my calendar gets less busy then”

And that is true. My calendar, as of today, is mostly free in 3 weeks. Woohoo! Relaxing times ahead.

However, my calendar is a rolling window of destruction with it’s view into a maelstrom of craziness.  By the end of Monday, I have filled the Monday and Tuesday 3 weeks out with new appointments. I don’t get less busy in 3 weeks, I just don’t know yet the things I will be busy doing.

This is a common theme with a lot of people I know. And if you have a calendar like this, then you have a risk on your hands. It is okay for me, I have learn’t how to manage my calendar well over the last year, but every now and then, I teeter over the edge of the crazy busy precipice, people frown at me because I am too busy then I pull back. For the most part it works for me. But here are some things I have learnt.

You need to stop thinking you are only busy “for a while”, and start thinking you are busy FOREVER, and develop some tactics to prevent your calendar turning into a blackhole from the weight of everyone’s expectations and collapses into itself.

Don’t just use your calendar for meetings with other people.  Unless that is all you do in your life, meet and talk and drink copious amounts of coffee (actually not too far off for me), you will have regular commitments and things you need to do. Put them in your calendar like:

Email. When I am not in meetings, I am writing email. In fact when people ask me what I do, I am usually honest and say “Talk a lot and write emails”. Depending on your volume schedule in an hour at start and an hour at the end of your day. That keeps you focussed in-between to get other stuff done.

Lunch. You do it every day. Book it out.

Preparation. You probably need to read stuff, or prepare notes, or papers, or just stare out the window and think about crap from time to time. Put it in! Perhaps just schedule in an hour now and then for general “prep”.

Travelling. Unless you live in your office and have all interactions with humans in your office, you will need to factor travel. Also, try and make all meeting at your place. Then you don’t need to factor this in.

Phone catch ups. I found this cool app on my iPhone the other week. It’s called Phone. And you can “ring” people and talk to them. I spent ages trying to figure out how to delete it, as people would”ring” me. But it is actually quite useful if you have the power. If you need a regular 10 min catchup with people, then do it as a phone call when you commute. Just pre-arrange it with them as they may have been trying to delete the Phone app from their smartphone too.

Coffee meetings. Those vague requests for a “catch up” over coffee, set a quota on how much time you can give to these each week, and put them in as a placeholder. Say 10-11am as many days a week as you can spare, block them out with placeholders, and once they are booked they are booked.

Friends. These can also be your lunch slots, but make sure you are scheduling in time with people important to you. Drinks after work. Coffee. Whatever. Put it in!

Exercise. Run, swim, walk. Plan it in. Walking or running meetings are awesome time hacks. Pro tip: in a running meeting make it with someone who needs to do all the talking. Also, swimming meetings are not productive.

Plan out your calendar with the “non-meeting” things every Monday, so you have a 3 week rolling window of all your other stuff too. Then the gaps you have left, they are the slots you can give to all the time bandits who want your attention. All the things you need to do every day are as important as each other. Be firm with your time.

Here are some “don’ts” to do as well.

Don’t convert pre-planned slots for friends, email, lunch, reading etc for meetings (unless it is critical). You are kidding yourself if you think you can squeeze all these into the imaginary gaps in your day.

Don’t work late every day. Even if working late is pounding emails at home on the couch or networking. Keep a quota of evenings free for the people you live with. If you are solo, well fill your boots, you need to get out and meet people at networking events.

Don’t think about everything being an hour. Default all your meetings and catch ups to be 30 mins. Doing this alone gives you twice the time.

Don’t think it is going to get any better.

So here is my calendar 4 weeks out. This is my regular template, with my regular commitments and I fill in the blanks between 10am and 4pm with anything that comes up. The placeholders for exercise, lunch and coffee etc I move around to suit. If no coffee catchups, they get converted. Evenings limited to two late out nights. Sometimes it’s one. Sometimes it’s 3.


I keep this updated a couple of months in advance. It works well. I think it gives me a good balance. Yours will probably look different. But give it a go.

Being busy isn’t bad. Having a full life is a good life. But make sure you are filling it will all the right things, and making room for everything you consider important.

5 Years ’til the Future

I was thinking about and progressing a five year goal of mine this morning and I realised something cool.


Did you know that in 5 years it will be almost 2020? That is THE FUTURE. All of a sudden it felt to me that the future is almost here. You know, the real future. 2020. It sounds like a real futuristic year. After the year 2000 we went into this period of lame years. Not that the years were lame in content, but the numbers just sucked. First of all we went through that period where no one was really sure what to call the years in short hand. “oh-one”, “two-double-oh-seven”? Then Twenty Ten arrived and it sounded better, and I was expecting it to be impactful in some way. The sound of it was quite punchy, and you could imagine a sci-fi film from the 80’s leading with “It was the year Twenty Ten!” and it would be all future and shit. But it didn’t happen. Twenty Ten just felt like any year.

I got to thinking about Twenty Twenty over coffee this morning as I pondered my 5 year goal I am working on (I will share at a later date). Other than an assessment of how well you can see, this year 2020 sounds like it will, finally, be an impressive future year. I have high hopes because today, right now, we live in an age now where the future feels just around the corner. We have Elon Musk and Richard Branson (and others) going into space. We are entering a golden era of manufacturing, with electric cars (Musk again), Makerbots and Kickstarters for almost anything you can imagine. Innovation used to be “The Internet”, now it’s real stuff of the future, and anyone can build it. Things you can touch, and sure that are connected via The Internet, but finally the future is almost tangible.

Five years is not that long. Like, if you had a five year goal to do something, then you would do that, THEN IT WOULD BE THE FUTURE. And this excited me no end. This is what excites me about 5 year goals, amazingness waits at the other end. But there is another reason I get excited about the impending and exciting future, because there is a dark side of five year goals that people don’t usually contemplate. It is something I have known about for a while, and probably explains some things about me and what motivates me.

Five year goals are awesome. 5 years is long enough to achieve something pretty cool, and because it feels like half a decade is a good nice rounded (yes I know it isn’t a round number) period of time. People always tend to think in terms of 5 years. It is a tidy number. You can fit two in a decade. And you can do all sorts of things in a 5 year goal.

Start a business.
Learn a language.
Move to a new city.
Have kids.
Grow kids.
Wait for kids to move out of home.
Change some aspect of you physically.
Get fit.
Build a house.
Travel the world.
Change some part of the world.
Fall in love.
Get married.
Achieve great things in your career.

There are all sorts of more interesting things you will think of as you contemplate what you want to achieve most in a 5 year goal.

There is one reason in particular I love the 5 year goal. I want to share it with you and this may be a little depressing. But it’s super important to contemplate and I ask you to contemplate this. Not to depress you, but hopefully to get you to think about 5 year goals a little differently. I am a little nervous about this, because it took me by surprise about 10 years back and I didn’t want to leave my room for a week.

Using the 5 year goal as a rough unit to achieve all the great things in life you want to achieve. Big chunky meaningful things. How many can you do? I mean think about it, and assume you can’t do many of the goals in parallel. And some of them may just be unattainable. The reality is life is all consuming and if you want to achieve something big you need to give it 100% of your focus.  So if you had to give 100% of your focus on achieving amazing new things, outside of the noise of regular daily life, how many could you do before you, you know, die? Kick the bucket.

Say you are 30. You can do two chunky 5 year goals then you are 40. That is cool. 40 is cool. I am 40. It IS cool. Then you can do two more the you are 50. I am sure 50 is cool too, but at 50 you will find that perhaps the options of goals in your list shrinks somewhat. It is kinda late to be thinking about growing kids or climbing Everest, not too late, but you know what I mean. Not the optimal time to do it. Two more then you are 60. That business you wanted to start? You can still travel, but not backpack like when you were 30.

You have a finite number of 5 year goals. Pick the wrong ones, or get them in the wrong order, and you find yourself wondering where all the years and your dreams to spend them on went.

Sucks huh? Sorry.

I personally hate thinking about the fact I have perhaps 6 – 8 big goals I can achieve, and all the ones I am most excited about doing right now have an expiry of perhaps 55 years of age. So I only have 2 or 3 of these I can do. Arggggh! What? CHEATED!

But I don’t think about that, you can’t because it is just depressing. Instead I think about what if you only had 3 things you could achieve in your life. Not an infinite number, just 3. What would they be? This I find incredibly liberating as it really focusses me on the things I want to do with my life. Before I use it all up. It focusses me on the future constantly, wondering what the next 5 years will bring, and how I will maximise them. And that’s why I am pretty excited about 2020. I have the feeling there will be some pretty cool stuff to do in the future. Perhaps some new goals will become apparent, like go to space! But one thing that won’t change is I have only a fixed number of goals left to achieve.

And that is why I get impatient in life. And why when I find myself procrastinating I get on with living it and achieving one of those 5 year goals.

Observing July

Found this old story I wrote in a journal a few years back, from a previous life. Thought it fitting on this July eve sitting by the fire.

My stove snaps and grumbles as it quietly snacks on the wood I feed it, loyal like my old dog was. I sit by the window observing the world with eyes closed. The window doesn’t close fully and I recline in my chair leaning onto its peeling frame to let the wind blow across me in. The fire warms me and the chilled air cools and I can’t make up my mind on which I prefer.

My legs and arms are crossed with my hands buried deep into my armpits. I have to extract them to sit up and toss the stove another bone, and I miss the outside air washing my face. The Kanuka is dry and burns quick and the smell leaves me wanting to smoke a fish. With pose resumed I close my eyes again.

The rain is clapping onto the thin and very tin roof; its waves of applause almost smother the sound of the fires delight. It teams together with the wind from time to time and manage a splash of droplets across my face. I know the surprise is coming but can’t stop my eyelids flinching, no matter how hard I try. I smile at the rains game, with the cooler of my cheeks rising slower and stiff.

Out in the greyness, beyond the baubles of water on the pane, through the essence of smoked snapper, past the waving Toi-toi and behind the drenched and exhausted dunes come beats of the waves. Kkrooowwkkkshhccccssssshhhh. I try to count them, sometimes two or three at the same time.

I stretch out further in my chair re-crossing my legs with left over right this time. I dry my face on my sleeve and close my eyes again. They all vie for my attention. I just sit and observe, letting my mind filter each sound in turn.

snap, tip tap tappy tip
fhewww e ewwww splash
tippity, snap, tip tap, kkrooowwwkkkkssshhhcccssssshhhhhhh.

I’m observing this July day with resting eyes.

CEO Idol

Every year I do an impossible challenge. It’s a thing. Okay so obviously the things I attempt are not impossible, because impossible is impossible! Right? It’s funny how often we use the word impossible in life not really meaning what we think it means.

impossibleImpossible. We say it but really, is it?

In previous attempts I have cycled solo from Steward Island to Cape Reinga. I told people and they laughed at me in my face, as I was a 100 and something KG fat guy who hadn’t done anything physical ever, and hadn’t ridden a bike since I was 13.  I dropped from 100+kg to a trimer 80ish on the way.

I’ve quit drinking for a year, quit watching sports. I’ve quit reading, listening and watching any form of news media.  I have started my own software startup. I have run 1,000km including 5 half marathons.  Again not bad for a recovering fat guy.I am pleased to confirm that I have succeeded in every challenge so far. See, not impossible.

I’ve mainly been alternating between quitting things and doing crazy physical things. I figure this way I gradually remove all the things that make my life worse, like bad news and smoking and do lots of good things for my body that make my life better, like running and cycling crazy distances.

This year I am adding a new category to my impossible challenges. To learn a new skill. I’m not talking about learning to do woodworking, or pottery, or hand-gliding. I have to learn a new skill and reach expert level. Well perhaps not expert, but generally nail it in some epic way.

This year my challenge is to learn to sing, in a band. Now, that alone sounds pretty doable. So to make it an impossible challenge, I need to learn how to sing (I am not a singer. Ask my kids) and get a paid gig singing in front of at least 100 people, for MONEY. And not get booed off. So not only do I have to learn to sing, but master a level so I am good enough that someone wants to pay me money and attract a crowd of 100 or more people. I have to overcome all my horrible fears and demonstrate my new skill publicly in front of a bunch of really critical people, basically not my family. Considering that any form of public speaking turns me into an incredible sweating twitching nervous wreck, singing is bound to give me a full nervous breakdown. I think I can probably get half decent enough at the signing bit. It’s the public gig part that is the impossible bit for me. But just as I felt a few years ago when I announced my bike ride of NZ to everyone, and quietly shat myself, I then overcame all my own doubts and I then went about doing it. One step at a time. Instead of focussing on what you have to do at the end, focus on each step that will get you there. One at a time.

That’s the bit I think that makes people think things are impossible. Self doubt. When you stop saying “I can’t” and then start saying “I’ll give it a go” you will find out there is a whole lot of things you can do. Amaze yourself at how impossible you are.

So I have the most part of a year to get a paid gig and nail this. In the meantime, DO NOT ask me to sing a song for you. I might punch you in the face. I am terrified of this challenge, and I need to slay some demons first before I can even consider humming a tune. But I will invite you along to my gig, if you are happy to pay ;-)



Moxie thoughts – UFB

Tonight was another fantastic Moxie session, thanks to Hayden Glass for organising these.  Tonight we were talking about the UFB rollout in New Zealand and what this means to us all, what opportunities it creates, and the value it brings.  Well that’s what I thought we were talking about.  I tend to absorb the discussion at the Moxie Sessions, then post-process it a lot.  Mulling over the conversations of the evening.  I am a little bit slow.  But here are some thoughts to share with the group and anyone else who is interested.

Here is what I think about UFB and the opportunities it creates for NZ, other than giving us faster Netflix, albeit illegally.

UFB is infrastructure.  It will take us years to roll it out to the majority of NZ’ers.  When we do it will be a great asset for us to use and abuse on porn.  Unless we find something else to do with bigger pipes to the home and business in NZ.  Consuming video, be it Apple TV, Netflix or Hulu (or Sky TV should they join this Internet phenomenon thing), is the obvious app for UFB.  It is the chunkiest content or data we consume today.  But consuming more of this via UFB just means we need to import more data from content producers offshore.  This doesn’t help NZ thrive, at worst it means we spend more time at home in front of screens lining US content producers pockets.  UFB will give us amazing infrastructure, and we will be the envy of the rest of the world.  This is the suggestion, not my assertion.  So how do we make the most of fiber, UFB and this advantage we will have over the rest of the world?

We need to get in the business of content generation.  New Zealand needs to export digital content to the world, or technology that helps generate and the consumption of digital content. This is a great opportunity for NZ, to do really cool shit with data.  Or we could wait until we can legally get Netflix and Hulu here and just consume.

10 years ago YouTube didn’t exist.  Neither did Twitter, and a lot of other tech we take for granted today.  YouTube was a couple of dudes.  So was Twitter.  They had some infrastructure and an idea and they built some stuff.  They happened to be in the US.  What if the next killer data app was invented in NZ.  I use the “Invent” word as this is something we Kiwis think we are good at. Inventing.  What if we invented a teleporter?  That sounds like it will need a lot of data, to send a whole person across space.  Might need fiber for that.  What about the next raft of Xeros, Vends and other software apps.  Sure you don’t need fiber for these, but to encourage every SMB to move their office infrastructure to the cloud. Fiber helps with keeping this fast.

In short, I think we need to get in the business of content generation and export it to the world. Content isn’t Shortland Street episodes either, but it could be.  It is apps, video, entertainment, and devices (yes hardware) that leverage off of really fast connections.  Holographic video conferencing.  A better Skype. Live reality TV streamed from your Google Glass glasses. Whatever.  We need to get in the business of exporting more bits to the world.  UFB has to help give us a competitive advantage here. Let’s get a bunch of big thinking ideas people together, give them access to capital and let them invent the future tech that will be in every home in 5 years time.  That’s what UFB enables us to do.  Not watch Netflix.  Although that is a pretty good use too, and I would like that.  It is just a pretty lame outcome of the UFB project if that is all we do.

Just some random thoughts.

Keeping busy, aiming high, and taking names.

I am part way through a bunch of projects so it is probably time for an update as I have been quiet lately. For very good reason.

For those that don’t know, I do a crazy goal every year. So far I have stopped reading newspapers (online and the “offline” versions) and TV news media for a year. That was a few years ago and I haven’t resumed media consumption since. I cycled the length of New Zealand solo, from the bottom up. Uphill. Started a startup. Gone from watching 5+ hours of rugby a week to none. Did a year of not being a consumer. And some other weird but interesting challenges.

Last year I was a little late in starting, and at the beginning of August I kicked off a dry year. 12 months of no alcohol. 10 months in and I can report some interesting findings.

Firstly, wow! Is alcohol really a big part of our life and culture or what? You don’t really realise this until you step outside and look in. The simple gesture of sharing a drink with someone is the thing I miss the most, and it is really hard replacing the significance of this with some other social interaction. Mostly people expect you to have a beer with them after doing a deal, or completing a project, or hitting a milestone, and when you suggest an orange juice, there is that awkward “I’m sorry, I didn’t know you had a problem with drink” situation or are you some religious fundamentalist where you have to explain that it is a dry year just for the challenge, and no other real reason other than just because. Going to a party and watching everyone progressively turn into morons over the course of the evening is quite surreal, and highly amusing. I can’t rate this high enough for it’s entertainment value. Sometimes I miss being a moron.

So two months to go and not sure if I will resume my habit of a glass of pinot in the evening. Running has become my new wind down tool.

About that running. So this year’s goal is to run 1,000km. The 1kk it has been dubbed. Roughly 3km a day. 20 a week. I picked 1,000k’s as it is specific, measurable (with your iPhone or a GPS watch), achievable, realistic (anyone can run 3km, you just need to do it every day) and time-bound, 1 year to do it. That makes it a SMART goal. Or something. But yeah, like my goal from 4 years ago to ride NZ solo, it comes down to being able to do something really achievable (run 3km, ride a bike for 6 hours) and repeat it on a regular basis, like daily.

In the first month I wondered if I could ever run 5k’s without stopping or puking. Now I can run 15km without any pause. Crazy to think I went from desk jockey to serial runner so quick. I now can’t wait to get out for a run. I love it.

I am 39% through on my 1,000 and on track to complete it by 31 December.

Screen Shot 2013-05-25 at 9.10.30 AM

I do a couple of 5km runs during the week then do a big 15+km run on the weekend. This works the best. I tried running 3km every day, then 6km every second day, but have settled on my current regime and it means if I feel like it I can push for a 20km run on the weekend. A secondary goal for the year is to do a half marathon.

The other thing I am running is my startup Vend, my goal from 3 years ago to do a startup my way.  Well, not 100% my way, I am not inventing anything new here. But 100% how I want to do it, and so far I have learnt my approach is not conventional, well in New Zealand anyway.

Vend is going exceptionally well.

There are many ways to measure the success of Vend, depending on your point of view. We are not cashflow positive yet, which seems to be to some the only way to measure success. Obviously that’s the endgame. Same for Xero and other high growth companies. We have been cashflow positive twice! First time it lasted a day then we bought a new laptop. We were a handful of people then. Second time we hired 4 new people, and havent stopped hiring since. We are, as Rod so eloquently puts it, not going to swim to the side of the pool. I think of us as going from the “Medium” speed swim-lane to the “Fast” lane. We want to grow as quick as we can to capitalize on the opportunity we have to establish Vend as the #1 platform for bricks and mortar retailers globally.

We have been doubling, tripling, quadrupling the value of the company every year, supported by our customer and revenue growth. We are growing between 10% and 20% month on month.

We have won a bunch of awards. 2011 Innovator of the year, Xero add-on partner of the year, Best Workplace 2012 in the Small Business category, 2013 Hi-tech Exporter of the Year (under $5m), 2013 Best Service Product, and others. I am proud of every award my team has earned. It is great recognition that we are doing amazing things, and will continue to.

Our team has gone from 1, me in 2010 to 11 at the end of 2011, 40 today and heading for 140 people as soon as we can find them, in three countries as we roll out our teams to the US, Australia and Europe. If you are looking to be part of something big, get in touch.

When I started, I wondered what it would be like to have 10 people on board. Then 40. Culture is a big part of our success. We have fun, work hard, and are passionate about retailers. We have built an amazing team who all feel like they have always been on board. That tells me we are doing something right when your team feels like one big family. 140 people will be the next cultural challenge for us, something we are not attempting lightly.


We have raised money four times. $100k, $1m, $2m, and just the other week we closed a round for $8m meaning we have raised $11m of capital in 3 years. We have raised all of our capital outside of the US with a large chunk of it coming from NZ, but half of our investment coming from offshore from Germany and Australia. I have an amazing shareholder list including Sam Morgan and Rowan Simpson from Trade Me, Christoph Janz, Christopher and the Point 9 team, Paul and Matt founders of Seek, Craig Winkler from MYOB, David & Nicki Wilson, Brian Gaynor and the Milford team, Koz and Amnon and the Southgate crew, Josh, Lance, Sacha, Nina and Craig, Miki and each of the Vend team who are all shareholders too. All A listers and all see the same big picture we see. We are building the #1 platform for bricks and mortar retailers. They all know a think or two about building big things too.

Not that there are rules around how you build a startup, but we feel we are writing our own in a way. Everything from our focus on culture, how we have raised capital, our global approach, and our product strategy. We are aiming high and pulling the slingshot back as far as the team can pull it, and are launching into the stratosphere.


So that is my update. Exciting times. Super busy times!

I wouldn’t want it any other way.

Long Exposure Effects

You got an idea.

You have taken that idea through to a product or a service.

You are ready for customers.

Now what?

There is always an element of “Built it and they will come” in every startup founders thinking when they come to launch day, 10X if it is an Internet business because every potential customer just needs to click on a link to your site, and “kaching!”.  Of course this is completely delusional thought.  Even just getting a link in front of a potential customer is pretty hard.

Again, same caveat as before, all I can do is share what I did and hope that it was right and is good advice.  If not, well at least I got you to click on the link to my blog post.

Before I even had a working version of Vend I was looking for every piece of exposure I could find, any opportunity to tell the world about what I was doing.  I had a working(ish) prototype on my laptop and I sat and had coffee with anyone who would listen and look at what I was doing.  The list got pretty long.  In a way I was testing the market, making sure what I was building was actually needed and wanted.  Of couse a lot of people thought I was mental, and didn’t think I would even get Vend off the ground, and if I did, it would most likely burn.  My prototype was ugly and I was hopeless at demos.  I really wanted to show off an idea, with broken code and a good story.  I probably wasn’t doing myself any favours with my Adobe Fireworks skills.

But something was working, amongst all the people I spoke to, some were already telling others about this crazy/awesome/ludicrous (pick 2)  idea that I shared with them.  Even if they didn’t like it, they were telling people about me and Vend.  Simple word of mouth was spreading my idea, albeit slowly.  I was already starting to talk to future investors as an outcome which I talk about elsewhere, but how do you get the all important validation from CUSTOMERS, the real people wo will pay you money?

Ben Kepes was one of those early people I barraged over coffee and Skype and any other channel open to me, including airport lounges.  He liked the idea, and suggested I enter for the Cloud Connect Launch Pad, an event in the Valley.  All I needed was a pitch, and a video demo.  Easy, I can use iMovie!  I was working on something at the time to help me with explaining my grand vision, so I did a quick recut (yes, seriously in iMovie) and submitted it to the Cloud Connect LaunchPad just to see what happened.  I don’t know if it was the charm of my kiwi accent narration, or my awesome iMovie edit skills, but VendHQ (as it was back then) was selected as a semi-finalist.  Whoohoo, I had no idea what the Cloud Connect conference was, or where exactly Santa Clara was, but if things went my way I would be there on stage as a finalist pitching my idea.  All I needed was 18 bazillion people to vote for me online.

Webstock was rolling up the following month, and a couple of weeks before the voting ended for the Launch Pad event.  And so I spoke to as many people before, during and after webstock making sure everyone knew Vend was a semi-finalist.  The levels of interest in what I was doing were increased somewhat, what was this Cloud Connect thing and why is Vend a finalist?  My demo video was doing the rounds, where I extolled the virtues of Vend and what it could do.  Part vapourware, part good iMovie edits, but it was working.  I had two retailers introduced to me, as a result.  Someone knew someone opening a store who needed a POS, and so I was introduced via email at Webstock.

These two retailers became my first beta users, and are still big Vend fans.

As part of my video I waxed lyrical about how awesomely Vend integrated with Xero, which it didn’t at the time, but I was working on it!  Tony from the Xero API team got in touch and invited me over to Xero HQ.  We sat around the board room table, and they eyed me up looking very seriously.
“You can’t use our logo and tell people you integrate with Xero when you don’t” he told me sternly.  “But tell me more about Vend and when can you get the integration ready?” he continued.  They thought Vend would be a smashing add-on.

VC’s were watching the video, and sending me emails to find out more.  Having something that people could watch and see what I was going on about for over a year made opening doors much easier.  Emails, Skypes, and phone calls.

Vend was not picked as a grand finalist, but just being a semi-finalist gave us exposure, our first two customers, and also introductions to a half a dozen VCs as a result of my video doing the circuit.  Well that and id being a smashingly good idea.

At Webstock one of the people I bored to death with Vend Vend Vend was Matt Cooney, Editor at Idealog at the time.  He was used to founders telling them why their next big idea was worthy, hoping for a plug in Idealog in their new future.  Matt was bored, and I wasn’t doing a great job of it.  Possibly the hangover post Webstock closing party was not helping.  But I smiled a lot.  I think that helped.  A year later Matt recounts that hungover pitch, and my face is on the cover of Idealog.

Me banging on my drum constantly got me talking to the majority of my future investors. Sam Morgan, Rowan Simpson, Christoph Janz, Sacha Judd, Lance Wiggs.  Each of them I shared coffee, or lunch, or a bike ride, or a Skype.  It was never the case of me sitting down with them, telling the story of my vision, and them saying “Great, how do I invest?”.  These relationships took several coffees, bike rides, and Skypes.  The more I spoke to them and updated them on the vision and progress, I painted a picture of where we had been and where things were going.  On overage, 6 months from first coffee to them joining the team.  These things take time, so you need to start telling your story as soon as you can.

I also was not shy in approaching people either.  What have you to lose?  New Years in 2010, I was at my summer home at the beach and was following Robert Scoble on twitter.  I tweeted him, on the off chance he might be interested in Vend and doing a post.  A few months later I was in his house at Half Moon Bay California telling the Vend story.  I sold him in 140 characters on Vend enough for him to invite me to his house to do a video.

Then I spoke to NBR, originally about getting Sam on board as an investor, and then to talk about our PayPal partnership..

Then there was the time I presented at Under the Radar.

Then the time I presented at Webstock Mini.

Then there was a geek talk about HTML5 at WDCNZ.

I am terrified of public speaking (can you tell?).  But any chance to tell a story and I was in, even if speaking in front of a room of people smarter than me make me feel physically ill.

Then there was the time I blagged my way into the board rooms of PayPal, Xero, Intuit, Google, Groupon, Square… the list is a long one.  The point is you have to start somewhere, with something that tells your story.  I didn’t even have a product, but I could sell the idea on day one.  And these stories I told, let on to introductions to journalists, investors, partners and perhaps even future investors and acquirers.  But most importantly it led to CUSTOMERS.  My first half a dozen customers came from referrals from people who had heard the Vend story.  They liked it enough to tell someone else.

Have you got your story?  It wont be perfect at first.  You just need a story.  I cringe when I look at all our early pitches and promo videos.  But they did the trick. Your list of intros will eventually get very long too.  But everything starts at the number 1.

Start talking.

1,000 1,000

Update: Oh, BTW. I clocked up the last k at 3pm on 31 December. I had to take the last 3 weeks slow just so I could hit the last KM on NY eve.

Screen Shot 2014-02-15 at 12.19.37 pm

Next year, 2013, I am doing something I am calling my 1kk challenge.

“What’s a 1kk challenge Vaughan?” I hear you ask. Well, as you asked…

Every year I do a mad challenge. A few years back it was cycling the length of NZ solo, this year is going dry for a year, a couple of years back it was starting some startup thingy. I have quit watching all televised sports for a year (now into my 6th year), quit all mainstream news media for a year (into year 3 now).   Sometimes it is quitting things, sometimes doing new things.  I try and alternate.  And so next year I am doing a 1kk.

The idea is simple, you can run, walk, swim, ride, pogo but you have to do it for 1,000k’s (1k-k).  Or 1,000,000 meters.  Woah, that sounds a lot.

1 million meters

You don’t have to do it all at once, that’s a lot of running or walking and would be MAD, but the aim is that over the course of a year (or a bit longer or shorter) you clock up 1,000k’s.

I am going to run it. The aim is a daily 3km run, or a weekly 20km run. 1,000km is far enough that you would need to keep to a regular commitment to do it, and obviously measure it.  Doing something 3km a day is achievable by almost anyone, and get’s you into a good regular fitness pattern.  Well that’s what I figure anyway.  Ask me again in July if it is a good idea.

You should do it to.  If not only so I have someone who can hold me accountable, but more importantly ’cause I think it would be awesome!  We can become best buddies on RunKeeper.

You may just walk it, that’s a 3km walk a day (2.74km to be precise). Rollerskate? Might be tough. It is a WHOLE YEAR, and trust me, that’s a long time to do something EVERY DAY. But the rewards from doing something like this are huge, HUGE! How great will you feel at the end?  AWESOME, trust me.

I will post how I go here.  If anyone is keen to do something similar let me know.  Think twice about that xmas ham.

Oxygen Supply – Getting Funded Part I


The most common question I get asked by other founders and people interested in the startup scene is “How did you go about capital raising, how much did you give away, and were you happy with how things went?”.

To a founder these questions can be as awkward as “What color is your underwear?”, “What’s your sexual preference?”, and “Have your stopped beating your wife yet”. Personal, kinda none of your business, and sometimes where “Yes and No” are both the wrong answer.

Not to say these things are or should be secrets, but every founder wonders if they went about it the right way, raised the right amount and gave away as little as they could have.

At the end of the day, funding is like oxygen, having a lot of it makes you dizzy and stupid. Have too little, slow, exhausted or dead. The trick is to find that middle position.

Simple right?


It is freaken hard.

You will need to spend all your time in full time capital raising mode, usually at the same time as you are building your product, or trying to find customers. But here is a summary of how I went about the seed capital raise, and my thoughts at the time, where I can remember them.

NOTE: This is not a playbook for how to get funded. This is how I did it, and only the initial round and could be wrong for you, besides my underwear is green, what color is yours?

Before you start:

Before you even start talking to investors, you need to build a good profile and case. They will mostly invest in you, so make sure you talk to people who you can relate to, and you impress them as someone who knows what they are talking about, and can get things done. I was lucky I was involved with Trade Me very briefly, so I could throw that name around a bit (if you have big names, put them in bold and italics). I had just been involved in a failed startup, Vianet, so wanted to add another credential to my CV that showed I could complete something and win. In the US being involved in a failed startup is considered a positive thing to have on your CV. You can learn from the mistakes. However in NZ, this is not the case mostly and tends to work against you “Bro, didn’t you hear he crashed and burned in XYZ!  Flaky!” and that sort of thing.

So I rode the length of NZ solo on a bike (and uphill).

Read my blog about my ride for all the motivations to do it, there were a few. But I wanted to raise some profile for me, and prove I could do what I set out to do. But this created a backstory, and ultimately made it easier for me to raise some capital. Everyone likes a half crazy founder doing amazing physical feats. Having a crazy moustache also helped. More more on this later and in another post. For now…


My bike ride raised my profile a lot, and put me in touch with a lot of great people who were huge supporters of mine. Some in tech circles, some in investment circles, some just big fans of facial hair.

After my bike ride, I was still building Vend in my part time, I was running a software consultancy business and in the global financial crisis I had quite a bit of spare time. So that’s why I was building a product in all the downtime hours I was not able to sell to clients. But I still needed to find work to feed the family. The time came when I needed to make the call, do I do this thing and go at it 100% or go do something else. Basically I couldn’t do both. So I went out and looked for some early stage seed capital.

“Angel” is a term that was once used to describe the retired banker who does some small investments from time to time for fun, and to help out entrepreneurs starting out. Now it mostly means “VC” without all the strings (mostly). The professional Angel is the easiest to find as they will have websites with portfolios. I googled and researched the local Angel scene, and found a few that looked like they got involved in early stage technology companies. Well that’s what their websites said. Some even had online forms that you could submit your funding request and business plan through. Awesome. I just complete the form then they wire me some cash! Yesss! One had a very comprehensive form that asked all sorts of the right questions, so I gave that one a go. A few hours later, after many pages of questions on a very flash application form, the whole thing crashed gave me errors and said my application could not be completed.  Their website also said they only take applications that have completed the form.

So I followed up via email instead, and it turned out the machine “ate” my application. Neat. So a exchanged a half dozen emails with this Angel instead. Now, when I say “exchange”, I mean I send an email, wait a week then have to chase up on it as it seems the machine eats emails too. The times I did get a response, sometimes with some questions in it for me to come back on, sometimes months later, I replied the same or next day. Then waited a week, and then two, then a month and then nothing. No reply.

I got to meet with one angel and Vend wasn’t for them, another wasn’t actually an Angel but brokered introductions to Angels (huh?).  But mostly people failing to reply to emails and phone calls. At the time I thought this was normal behaviour, and I was failing an initial screening process, and perhaps they got hundreds of approaches a day.  I had never done this before.  But now, having been through the cycle a few times, up and down Sandhill Road in the heart of Silicon Valley, I know that this was not normal behaviour. My timing could have been wrong. Perhaps I was too early stage. My business plan could have sucked. My bike shenanigans could have been a turn off, thinking I might disappear for another 6 weeks on my bike any second. Perhaps it was the moustache. Things might have changed since the GFC and I hope so. But an email or phone call saying “no thanks” or “we are busy” would have actually been nice.

My advice is to be friendly, firm and direct and set the expectation that you want to hear back from any professional Angel ASAP and then if you don’t get the attention you are after, move on very quickly. Remember, these guys do this for a living, so don’t think you are inconveniencing them by bothering them. They do get busy, and sometimes need a reminder email.  It happens.  But think, would you want an investor on board whom when you needed their help they may or may not reply to your emails? The answer is of course no.

For me at the time I gave up on this path completely disillusioned believing no one is interested in funding NZ technology companies. I was still slowly pushing my product closer to market. The irony being if I had just put my head down and not been distracted with seed funding, I may have got my product to market 3-6 months earlier, and burnt through less of my savings.  Capital raising is always a distraction, as it takes you away from doing other things like building the business.

Talk to others who have raised from local Angels, there are a lot of them around but they are quite hard to find. You need to be doing dozens of meetings over coffee to find them. Failing that go here and find some Angels and tap into these new Angel networks around the country, but really do try your networks first that way you will have a common connection and applying cold via websites dosent yield good results in my experience.

Friends and Family?

Friends and family is a good alternative to the angel round, money is money right? If it gets you going then it reduces the risk of your failure. However, I really wanted to avoid this path having had good people and friends lose money in other startups I was involved in. I wanted to keep this completely professional. If this was my next big failure then I would still have some friends and family left. Considering my failure to find a good professional Angel and the disappointing market for investment in general, my choices were limited. I tapped deeper into savings, and cleaned that out, and things were getting really tight.

I entered Vend into the Cloud Connect Launch Pad in Santa Clara, and was surprised to be picked as one of the finalists. This gave me some great exposure so early on, and helped validate that what I was doing was interesting to others. People were starting to get interested in what I was doing now.  I was building a profile and validating my idea. A few friends and family were starting to get interested as this seemed to be more than just some side project I was working on.

Two friends I was somewhat hesitant to call on, were Rowan and Sam. Looking back, I think I was perhaps afraid they would say no, after Vianet crashed and burned. I have since discovered this to be typical “kiwi” thinking pattern, “Nahh they wouldn’t want to invest! Besides, the shame if they said no” and just the whole way failure is considered, well a failure. I had caught up with Rowan on my bike ride and at the time told him about my crazy idea for Vend. I think I even had some screen shots in my bag. He helped me with my thinking around my model, and then we rode out of Wellington together over the Akatarawa ranges.

Over a number of months I asked them both for a lot of advice, still hesitant to ask them for cash. I had also gone off the whole investment thing to be honest.  I was just focussing on getting the product to market and taking help where I could find it.

Sam gave me a loaner desk in one of his other companies to get me out of my spare room. I only worked on Vend when I was at that desk and I was spending more time at that desk than anywhere else now.  I had some beta customers using the software.  I was running on the scent of an oily rag, even selling stuff on Trade Me (ironically) for extra cash.  Then one day Rowan popped by, and suggested I need to raise some capital now if I was serious about this thing. We talked some terms, assuming he was interested. A month later both Sam and Rowan had invested $100k. I could start working in the business fulltime, and gave us a budget to promote and hire in some help as I needed it. I publicly launched Vend the next month, and we were off.

In the months preceding the actual raise, I spent a lot of time with them showing them my model, talking about what we would do with the capital, and our go to market strategy. It helped that they knew and liked me. But I still had to do the hard yards proving I had a business. I could have had the exact same conversations with others, but Sam and Rowan were a part of a minority of people who took the time to listen and ask questions. I must include Lance Wiggs here too, who gave me a lot of time, and invested later on down the track.

I went to them both for advice first. I respected their experience and valued the input they could provide me and Vend. I didn’t go to them for money straight up. This is true for a lot of my other current and potential investors. Start the relationship around advice, and guidance. Ask them what you should be doing, not just about funding, but about structuring the business, go to market plan. Get their advice on everything. If they have invested in a number of companies they will have been through first hand some of the challenges you are about to face. Take their advice. Demonstrate you can take advice and act on it. Smart investors will be looking to see if you can take guidance, or do you think you know it all. The latter never ends well, unless you really do, but then why would you be asking for their help? You know it all!

Just a couple of weeks before Sam and Rowan signed the dotted line, I caught up in person with a couple of Angels at a founder + angel meet and greet event.  They were talking at the event about investment and the ups and downs of being an Angel in NZ.  Afterwards I approached one, who had stopped replying to emails, just to say “hi” and let them know about progress. I was pretty excited about Sam and Rowan chipping in, and wanted to say thanks for all their help (which was me being polite because they stopped replying to my emails). I only got as far as introducing myself and Vend then was cut off mid sentence with,

“Oh you, I sent you an email saying we are not interested. You must have missed it. We don’t invest in the retail space.”

I only wanted to say “Hi”. I never got that email, either their or my machine “ate” it.  So I just moved on to the sausage rolls.

Investors get approached a lot, and probably get stalked too so they can get blunt. Next I sat down (cautiously) next to Phil McCaw from Movac (whom I had never spoken to before), to get his opinion on what I was doing. He was engaged, interested in what I was doing. At the end I mentioned Sam and Rowan were looking to back me and asked what his thoughts were on the both of them, from his experiences from the Trade Me days.

“Go for it, you won’t look back.” And so I did, and I haven’t.

Do some due diligence on your investors. They will be doing it on you, and you want to make sure you know who you are getting into bed with. Are they helpful, completely hands off? Hard nosed, or relaxed? Do they reply to emails? I have since chatted to Phil a few times, not asking for funding, and he has given me some pretty great advice. Some investors you will talk to won’t be as helpful so hunt out the ones that are. They don’t need to invest in you to be helpful. The smart ones will see the benefit in helping the ecosystem,and perhaps they might get an opportunity to invest in you later on.

So yes finding angel/seed investment in NZ is hard, and still is hard based on the conversations I have two or three times a month with other founders trying to do the same. But with a number of great success stories starting to emerge now, like:

…it has to be getting better. Surely? Honestly I don’t know if that is true.

Don’t let a cold response from a potential investor put you off. When you are getting going, a “no” (or worse, no response at all) is devastating. You desperately want to know others see your vision, and that you are not some crazy nut-bag. I almost packed it in when it seemed no investors wanted to talk to me. But I just needed to feel out what and who were the best partners for me. People do actually get funded, even though we are not in Silicon Valley. But it is hard hard work, and it is hard work in the Valley too. Did I mention how it is hard work? It is hard… work.

So here are some tips if they are helpful to you.  Again this is just based on my limited experience:

  • Build a profile, and establish a story around you. Investors will invest in you first then your idea second.
  • Get enough cash to get you going 100% into the business. Doesn’t have to be a lot. But it starts the investment cycle which is a long one that only ends when you exit or break even. Plan on getting good at raising money.
  • This seed backing will make it easier when you come to the next round as you will have some history and a track record, and you will be a little more practised in capital raising.
  • Getting backing from successful business people is a bonus, especially if they exited for large amounts of money.
  • Friends and family are good too. Spend all your money first before asking them.
  • When talking to investors claiming to be professionals (i.e. they do this for a living), if you are not getting a response then drop them a line to say “thanks” and move on quickly. Time to market can make all the difference to your business, and it sucks having to chase people up for a response to an email.
  • Talk with a lot of people. A lot.
  • Talk with people you like and feel comfortable with. You will hopefully be working with them for a long long time.
  • Look for really simple terms. Leave complicate stuff like vesting, liquidation prefs and all the other stuff for much later. You are looking for a small amount of cash to get you going. That is all. You aren’t raising $10M.  Seed funds should come with little to no strings.
  • I gave away 30% for this round. Your call on if that is right for you. I am a sole founder, so I was looking at my early stage investors as being part time co-founders, and they have supplied more than just cash, in the form of time and resources. It was a good deal for me. You should reward your early stage investors as they are taking a huge punt on you before anyone else does.

I have since moved onto two additional funding rounds totalling over $3M and will cover this stage in another post later on about the A and B (and possibly C, D, E) rounds.  Like I said, you are always in capital raising mode :)

Good luck! If you have a story I would love to hear it.