Who cares? Who cares what the future brings?

I've just come home (at the time of the first draft anyway) from watching the incredible 20,000 Days on Earth. I've been a Nick Cave fan for years, so whether or not I would enjoy the film was never in doubt. I even travelled to Sydney in February of last year to see him and it was one of the best concerts I've ever seen. The combination of his brilliant catalogue, that band, his showmanship, and a deep, personal connection with Sydney and particularly her Opera House lead to a jubilant and emotional experience that I don't think I'll ever experience again. But that's not what this piece is about.

The thing that really struck me about 20,000 Days on Earth was Cave's dedication to nurturing his genius. I was both full of admiration and struck by an intense jealousy that he has been able to devote his life to this craft. It made me think hard about my current position. About the nature of my being, even, which is quite an achievement for an 88 minute biopic.

Watching Cave go through his 20,000th day on Earth one is forced to contemplate what one's own 54th year may look like: where you'll be, who you'll be with, what you'll be doing, what you'll be known for. It made me uneasy I must say - though I appreciate that it finally gave me an emotion strong enough to motivate me to write after my last piece, the story of Popin.

At my core I'm a perfectionist. I want, nay, expect to be excellent at everything, and this is only made worse by my tendency to not self-promote - which butts up nicely with an intense desire for success and recognition. There's a glaring issue with all this: I'm not excellent at everything, far from it normally (don't worry, I'm emotionally stable and this isn't a cry for help, merely a clumsy attempt at an illustrative example). I'm a relatively quick swimmer, but I never made the times I wanted. I'm a pretty good musician and songwriter, but I'm still looking for the magic. I'm a pretty good developer, but I'm far from the best. I've got some good skills and experience around starting businesses, but mine never seem to work. I've got a pretty good life, but it doesn't fit the idealised view of what I really (think I) want.

My point above is not to list some skills I have, but to express that I live my life bouncing between disciplines; throwing myself headlong into something only to sniff the possibility of a better life somewhere else, shifting course and throwing my weight behind that. If nothing else I seem to have an aptitude for the adjustment, but I know this constant sense of inadequacy and unfulfillment is always there, always encouraging me to try the next thing because maybe that time it'll be easier. Maybe then I'll get that win that I crave, that elusive win that appears to drive me.

The thing is, I don't actually think it's just me. In fact I feel it could be generational, though I have no data to prove it and haven't had much luck coming up with any. In my work with The Distiller and the broader startup community I see a lot of people who are quite similar to me. People who just want success, and who aren't particularly concerned about what it looks like, so long as it's theirs. This desire for success is hardly specific to a generation, but it seems that my generation (I'm 27, you can work backwards from there) is predisposed to being constantly unhappy with their current situation, at least that's what it feels like. In my narrow bubble of the world most of us were brought up with a lot, and I think we find it quite hard to reconcile how we're ever going to achieve a life that was as good as the one we were raised within, particularly while doing 'what we love'. Under constant time pressure, automation, scaling house prices, globalisation etc., the concept of having a comfortable middle class life feels quite distant, so I think we've all told ourselves that we're OK with sacrificing that particular dream, so long as we can travel and party. I know I've told myself that.

It feels like, as the old pathways have disappeared, we're all being forced into taking more risks with our lives, careers and livelihoods, risks which the generations before us haven't had to encounter, while all the while dreaming of being able to de-risk as soon as something works. It all raises a question...

What if something we do actually works? What if I luck onto that hit song, that killer startup, that swimming...hah no that one's definitely not happening.

I don't really know what happens then, but I don't think it's in my nature to actually be happy with it. I'd likely be looking to the next thing, already dissatisfied with the last one as my threshold shifts and my self adjusts. That's what we've been conditioned and told to do, after all. I feel like my entire education and upbrining was always oriented around looking after oneself and making sure that you got yours. This isn't a sleight to my parents as they did their best to raise me as conscientious and community minded, but I think all of us post-rogernomes have been fucked up a bit, in a way that older generations haven't.

We post-rogernomes were born into a country freshly unshackled and opened to a whole new, consumer world. We don't know anything else and things that before Roger seemed self evident, just aren't for us. Where older (than us) people become selfish dicks because their circumstances encourage such behaviour, we don't have a choice. We were raised this way.

I don't really know what to say now. I don't have any snappy conclusions or tips. This isn't an instructive blog post with an easy to digest morsel hidden at the end. I hope that others have seen something in this though. I know I'm not alone in such apprehensions and motivations, but I feel like few people talk openly about this. I guess that's because it's hard to admit that you're afraid, or that you'd really rather be doing something else. I think it's also embarrassing. There's nothing worse than trying to put on this facade of success and self-starting, to admit that there's very little behind it.

At the end of Cave's 20,000th day on earth he goes home, sits on the couch and watches Scarface with his kids. It's scripted, sure, but I bet to your average 20-something, stuck in a shared house in an overpriced city that they will probably never be able to afford to settle in, it strikes close to home and hurts, just a little bit.

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Three years

Three years is a long time to spend on most things. If you'd asked me when I started this last, perverse, journey where I would be three years down the track, I probably wouldn't have told you negotiating the end of it with the options being considered consisting of just shutting it down, letting a partner take it all, or shutting it down and releasing all our work into the public domain. No willing buyer. No riches. No, I definitely would not have predicted that.

What am I even talking about? I'm talking about my last, proudly failed startup that we called Popin.

Just quickly, if you're hoping to get a list of '20 Things You Should Definitely Not Do As A Founder', you're not going to get that here. Those lists are plentiful and most are filled with great advice which you will devour and, promptly, ignore until you're in the post-mortem stage and those lists come flooding back and help you to categorise what you did wrong. I don't plan on giving any direct advice either, the internet is full of blowhards people who will happily shout at you about their long experience gleaned reading books and blog posts, or who write with so much survivorship bias as to slaughter all hope of their message being universal or relateable.

To be honest, this essay is for me. Like most I've been 'meaning to write more'. A major block has been my desire to at least address this part of my life formally, publicly; this urge disrupting (ha!) any other attempts I've made to start writing on other subjects. I've been wanting to do this for a while (we agreed to stop working on Popin in September 2013), so as much as anything, this is just an adhoc way for me to acknowledge something that happened and then move on. Perhaps with some insight along the way. Perhaps not.

Popin was originally a website, built in 2010, called Let's Tweet Out. This was founded by Jamie MacDonald (now the founder of a great startup called Storypark) and myself while we were being noobs down in Dunedin (New Zealand) as members of The Distiller. We were in The Distiller ostensibly to build businesses, but for both of us it ended up being more of a personal development exercise than a business development exercise. Jamie was the designer, I was the coder; we were both, at best, enthusiastic imposters when it came to being 'founders'. Let's Tweet Out was (and I think still is...) a great idea. We'd seen What the fuck should I make for dinner and were both blown away by how simple yet effective it was at making you actually choose something. We decided we should build this for choosing where to go for dinner.

I'm not going to dwell on that product too much, suffice to say we built it and it kinda worked. But then we got distracted...

Like all good early tech founders, we didn't know much about building a website audience. We had heard of a Sydney-based accelerator called Startmate and we immediately pivoted (ha! ha!) our focus towards getting into this. We were convinced that, once they realised the giant opportunity to build Let's Tweet Out for everything, they would take us instantly.

Things didn't quite work out that way: they were nervous about hospo people being cheap and this making our sales process expensive.

We did the rational thing next. We decided that, because they were nervous about hospo, we should just build the ambitious thing now! We recruited two more co-founders (James Bushell, now running an agency called Motif, and Stevie Mayhew, currently a senior developer at a prominent agency here in Auckland) and set out building what a friend of mine would later describe as "the internet". This was a social network which had business listings and could do location stuff and had ways for people to follow you and businesses and group your friends into businesses and would probably be adding Washio's features if we had kept it up. Eventually, due to no one knowing what the hell they were meant to do on the product, we realised we'd created a monster and set about taming the beast. Jamie had, wisely, started Storypark by this time, so we enslited Felix Terpstra to help us design the new, leaner Popin.

This process went really well. Felix produced some great designs which we set about implementing. Problem was, the initial code base was a mess and both Stevie and I were quite busy with other contract work now - due to us both having grown up and become useful to people who needed dev work done. I was mostly doing Ruby on Rails work so in my infinite wisdom I decided it would be best to rebuild in Rails as a way of cutting ties with the legacy app and because Rails felt totes more productive (I wasn't that experienced in it yet). I convinced the others of this and off I went. Of course, Stevie was still a PHP developer so wasn't able to help much: my desire for productivity now meant I was the only person able to work on the app. I also decided that the front end should be built in Ember JS (recently released, still not 1.0). Things were as productive as you'd expect.

Throughout this whole ordeal a little thing called mobile had stopped sucking. All of the people who were meant be our customers were now carrying around small computers which had location capabilites and were always connected to the internet. They were using apps which did the same things that our app did but weren't our app. James and I, over a delicious Japanese lunch on Courtenay Place, decided that we should restart once more. We decided to build an iPhone app which would allow you to share short notes about places, privately among your friends. The idea was that if everything were private and everyone was known to the user, they could both be more honest when they were posting, and more able to reason about the recommendations they were seeing from their friends - i.e. if you know your friend has terrible taste, you can use their recommendations as warnings and then the information is still valuable.

Stevie, wisely, left at this point.

Felix got to work and we produced a nice little app. It did everything I just said, but didn't seem to capture anybody, especially not the way that Snapchat and other apps that work on more intimate networks have since. We got to about 70 users or so, some who actually quite enjoyed it, but in the end we'd all just lost enthusiasm. There's only so long you can work off the back of your own hubris.

Now, I know I said I wouldn't try give any advice, but I'm willing to plead a charge of hypocrisy in order to convey this one, very important point: In the early days of an endeavour EVERYTHING is your fault.

You may have co-founders/collaborators/bandmates who you can (and probably really want to) blame, but you'd be wrong to. They likely may have contributed to something going wrong, but, when there's only a few of you, you either let them do it (bad) or (worse) didn't know they were doing it.

To clarify, I don't raise this in any specific sense for any specific action Popin took. We were all guilty of blindness to each other in some way - that's probably why this is a failure tale - but it's all very irrelevant now. I merely want to emphasise that, when you start something from scratch you're confronted with an object that just won't gather momentum no matter how hard you try. This leads to bad decisions and they aren't any single person's fault, they're everyones' fault because no one stopped the bad decision being made. This isn't malice, this is just life. Learning this was my biggest lesson from Popin. You have to trust your co-founders, but everyone also has to be in each other's business too. You have to confront everything when and as it happens - it saves far more energy than you'd imagine, despite what other discomfort you may feel at the time.

Back to the story though, to describe an ending without fanfare. On a typical, miserable, Auckland 'spring' day last September, the remaining three of us decided to wind down the company and open source the code over coffee at Imperial Lane. If you'd been friends with me on Popin you would've known to go there.

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The blurst of times

This is the first post. As usual on most blogs, it's meaningless. Time will tell if the content gets any better.

Keep in touch,
Chris

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