My failings

Posted: January 27th, 2012 | Author: | Filed under: General | No Comments »

I’ve run 8 different businesses over the last 10 years. Some have been successful, others have failed.

You can read a lot of blog posts out about successful startups, projects or campaigns but few people post about the ones that sucked. Here is a list of some of my failed projects.

360Desktop (2008)

What was it?
An angel-funded startup building a Windows application that extended your desktop into a panoramic display giving you (in theory) more screen real estate. I joined as the marketing manager.

Why did it fail?
A range of issues but I think the biggest red flag was when I was hired with the view that they would launch the product the following week. 6 months later and with the launch nowhere in sight I left the company to do something actually productive. I think it took them another year or so to launch and not long afterwards the company folded leaving a bunch of employees out of pocket.

What did I learn?
Know when to hold ‘em and when to fold ‘em. I also met some incredible people, particularly user experience designers Benson Low and Adam Schilling.


Mr Chop (2009)

What was it?
A music-centric blogger advertising network I started in part to monetize my own blog.

Why did it fail?
The network made a bit of money but nothing significant. It certainly didn’t get much beyond ramen profitable, and not consistently.

That said, over the last 12 months I’ve revived the business as a service we offer through Native. With a stronger client base and a better understanding of media buying it has definitely been a good addition to our bottom line.

What did I learn?
A great idea is nothing without the right networks or distribution. Also ad sales isn’t hard when you’ve got a good product. Also sometimes a good idea needs a couple of years to work – for me I needed to learn how to sell media and manage client accounts well before this business made sense.


Orgnition (late 2009)

What was it?
An organisation management system for not for profit organisations, specifically those like Rotary or Lions clubs.

Why did it fail?
We underestimated the strengths and overestimated the weaknesses of our competitor. We also massively underestimated the sales cycle. It’s not an easy task to sell a technical product to older organisations, especially when their existing solution doesn’t completely suck.

What did I learn?
It’s better to do something you know than chase a dollar. Also working with non-profit organisations is not an easy task. I still believe in the solution that we had but think that it will be some time before I step back into this space.


There are plenty of other ideas I worked on but didn’t go anywhere with. I have notebooks filled with ideas, research and sketches. But the above are ones I spent any considerable amount of time on.

During this period I also made the conscious decision to treat each failure as a learning experience, to resign myself to failure as if each project were another semester of study into how to build a company.

I didn’t start any of these projects wanting to fail but I always went in with the idea that it was about the process, “the journey” rather than the end result.


Be embarrassed

Posted: November 15th, 2011 | Author: | Filed under: General | No Comments »

The goal for your the first release of your new product should be to be embarrassed by it.  It shouldn’t be perfect, it should be good enough.

“If you’re not embarrassed by your first product release, you’ve released too late.” – Reid Hoffman, Linkedin

That’s not to say I don’t think beautifully designed products are important – they most definitely are – but you won’t know what goes into a beautifully built product until you have some data from your potential customers.

Andrew Mason at Groupon did just this when they pivoted towards their current business model:

“We took a WordPress Blog and we skinned it to say Groupon and then every day we would do a new post. It was totally ghetto. We would sell T-shirts on the first version of Groupon. We’d say in the write-up, ‘This T-shirt will come in the color red, size large. If you want a different color or size, e-mil that to us.’ We didn’t have a form to add that stuff. It was just cobbled together.”

Your first release is unlikely to get a mass market release. The odds are that not many people will see your less than perfect product.

In fact your first marketing and product development release should be fairly targeted to a subset of your target market. And it should have just enough functionality to settle some of the assumptions you’ve made. By limiting the number of people exposed to your product you also limit potential fallout until you get some data to improve it, you also increase the number of iterations you can serve to different market segments to gather further data.

You need to be able to gather enough data to know that you’re onto something and that you should invest more time and money into the project.

A few people you release to might poke fun at the work you’ve done but it doesn’t matter.

If they’re people you respect then when they see the well finished product at the other end they’ll understand the path you took.

Aim to be embarrassed.

Invest in yourself

Posted: November 8th, 2011 | Author: | Filed under: General | 1 Comment »

This last weekend I made an investment in myself that paid off.

I’ve been wanting to find new startup collaborators for a while – or even just smart people to work with at Native. So I signed up to Startup Weekend – a competition where you pull together a team to build a startup project and (hopefully) launch something in a weekend.

I wanted to invest in my ability to develop compelling startup concepts and execute on them.

It was an intense weekend. We worked hard from Friday at 8 until the pitch on Sunday at 7 with very little sleep in between. The two main things I got out of the weekend.

1. Everybody sucks.

It’s hard to articulate your idea to people who you don’t know in a cold pitch.

When I pitched the idea for Theme Pivot no one really got what it was and I didn’t really know how to convince them.

I sucked.

Yet somehow I still managed to convince a couple of people that my idea had merit. First our small team of legends and Mark Pesce who ended up giving me an HTC Android phone for “Best Pitch”. Thanks Mark!


2. No reward without risk

There was a fair bit of risk getting involved in doing Startup Weekend. It was a lot of time to give up, particularly at this time of year. There was also a lot of people I respect there. It wouldn’t have been great to fail in such a public way.

It would have been a lot easier to focus on perfecting a project over months without that kind of pressure and release when I was ready, when the product was finished. But then I wouldn’t be seeking rejection.


We ended up winning the weekend with our concept Theme Pivot – a service which takes your CSS from “good enough” to pixel perfect. We won $5k in cash, $1k in Amazon credits and $5k in credit against co-working at the York Butter Factory.

And the investment I made in improving my startup and product development skills paid off.



The Art of the Cold Call

Posted: September 29th, 2011 | Author: | Filed under: General | 1 Comment »

Last night I went to my first Skillshare class, the Art of the Cold Call.

I’ve been a cold caller for a while. My first cold calling gig was giving away tickets to a design expo. My next was cold calling motorcycle dealers for Vmoto. Then entrepreneurial speakers for the Hive.

More recently I’ve cold called for entrepreneurs for the used it to find trainers for Sessions in Melbourne and New York.

Cold calling isn’t about harassing people about their mobile phone plan – at least not for me – it’s about getting in touch with people who you would otherwise have no personal connection with.

The teacher was a recruiter for tech startups and the other people in the class were in mergers and acquisitions, the founder of a travel-based film festival and an art dealer.

A great class for anyone working on a startup, particularly around customer development.

Here are my notes:


Prepare your call sheet the day before
- reduce the barriers that stop you making the calls
- separate the task of gathering information (an easy task) on who to call from actually making the calls (a not so easy task)
- include name of lead, company and a talking point for the intro

Seek rejection.

Aim low
- start with making 1 call a day
- don’t try to start with 20 calls a day, you’ll suck and then burn out
- build slowly as your confidence and ability increase

Mark success
- but not by the outcomes of the calls
- mark it by the volume or other factors
- rejection is par for the course, embrace it

Find a cold calling partner
- lock yourself away somewhere together for an hour and commit to making 5 calls
- remove ego from the equation by doing it with someone else
- helps to let your guard down and relax you
- increases accountability through the social contract
- introduce game elements “I’m going to keep this call going for at least 2 minutes”
- make it competitive

Cold calling is like asking someone out
- you don’t start with what you really want – a long and loving relationship
- start with something small – like time (a meeting or a follow up call)
- then shoot for something bigger
- then shoot for the close


The Anatomy of the Call

1. Intro

- always script it. Remove any doubt around what you need to do to get on that call
- Once you’ve done the intro throw the script away and have a conversation
- The opening line ensures you get past any trip wires, make it personable and relevant and demonstrate that you’ve done your research.
- “I thought I’d give you a call because noticed that you do x, y and z”
- Reduce ability for rejection

Respect their time
- acknowledge that you’re interupting their day and this might not be a great time
- Let caller decide if now is a good time or not
- If now not a good time, setup a time when it would be appropriate
- Once you’ve got that commitment you’re at second base.

2. The Middle

- always freeform
- focus on getting the lead to talk to keep the conversation going
- ask “how” and “why” questions versus questions that can be answered with “yes” or “no” which will halt the conversation
- drive energy and enthusiasm in the conversation, build it to a crescendo
- switch to the ask

3. The Ask

Be direct
- be clear about what you want and why
- it could be a meeting, another call or to send an email with more information

When unsuccessful
- have a plan B, C and D
- if you can’t get the meeting ask to send something via email, ask for a meeting at a later date, ask for a referral to the right person etc
- get something out of the call



Start by calling as high as possible
- like the VP of Marketing
- you’re seeking the Director of Online, ask who that is and you have a referral
- people love to help, helping is easy
- can be then used as an internal reference
- helps to navigate larger organisations

Call the Sales Department
- they always pickup
- they love to talk
- they’re usually incredibly helpful
- they know a lot about how the company works
- use it as an exploratory call to scope out the target organisation

Overall it was a great class and I thoroughly recommend it. Check it out here:

Seek Rejection

Posted: August 2nd, 2011 | Author: | Filed under: General | 7 Comments »

I’m a massive fan of rejection. It’s what keeps me moving. If I wasn’t a fan I probably wouldn’t be in the business I am in.

Every day I send an email or make a phone call to someone that is likely to get me a rejection. I make sure that it’s about something big and meaningful – something that is likely to cause rejection but if it doesn’t will lead me onto something bigger, something interesting.

Yesterday I emailed a publisher I know about the potential for a book around Tourisms, the photographic travel guides.

The day before I emailed a Singapore-based agency about the potential for cross-collaboration on a different project.

The day before that I struck up a conversation with a NYC startup about a way to add a viral loop to their product.

Most days I get rejected one way or the other. I hear nothing back or I get a short response that the person on the other end isn’t interested in my idea and would like me to go away.

Sometimes it takes days or weeks to get the rejection but it usually comes.

The reason I do it is because when the rejection doesn’t come, when acceptance comes, it’s spectacular.

And every day I ask myself the question “what did I do to get rejected today?”. It’s my way of keeping score, of making sure that I’m still moving forward.

Seek rejection. Every day.


Drew Houston on deciding to pursue Dropbox

Posted: July 31st, 2011 | Author: | Filed under: General | No Comments »

I found this great post from the founder of Dropbox, Drew Houston, on Hacker News.

Someone had asked him if Dropbox (currently valued at $5b) was his first idea.

“[I] informally came up with and tossed around 6 or 7 ideas at the same time — not so much coding as investigating/talking to potential customers and bouncing them off other friends and entrepreneurs.

this was crucial — ideas don’t really fall out of the sky, they evolve.

there were several times where i’d get really excited about one idea — like pacing in my living room at 5:30am excited — and then 5 days later find out (via a different set of search terms or something) there were 3 other people doing the same thing, with a head start and more money.

ultimately they say scratch your own itch — this was a problem (syncing a 3gb file across several computers efficiently) i routinely had working on a prior company i had started and i was frustrated that no one had solved it well, and it turned out to be more promising than my original company :)

Stay hungry

Posted: June 9th, 2011 | Author: | Filed under: General | No Comments »

“the key to staying on top of things is to treat everything like its your first project. Like its your first day working as an intern, that’s how you try to treat things. Just stay hungry.”

The future of relationships

Posted: March 30th, 2011 | Author: | Filed under: General | Tags: , , , | 2 Comments »

I’ve been mates with Nick Crocker for three years now. We met after discovering we both ran music-related marketing agencies.

In June I started working with Nick on Native Digital. Shortly afterwards I became a partner in the business, running it as a going concern while he was in the U.S with Boxee. Nick was still actively involved in the business, particularly in strategy and business development, but as of March 1, I took over the business as sole director and majority owner.

In our time working together we’ve taken the business to its largest contracts, its largest quarter, and if all goes well, its best financial year to date.

Yet only today, in one of our frequent Skype calls, we realised we had met in real life on three occassions. The last was 2 years ago.

We’ve built a rock solid friendship and a successful business. Nick has transitioned out and I’ve taken up the reins. And it’s all happened while we were on opposite sides of the planet–with communication split between Skype and email.

Is this the future of business? I’m not sure, but it worked for us. YMMV.


Andy Warhol on Coke.

Posted: July 25th, 2010 | Author: | Filed under: General | Tags: , | No Comments »

“You can be watching TV and see Coca-Cola, and you know that the President drinks Coke, Liz Taylor drinks Coke, and just think, you can drink Coke, too.

A Coke is a Coke and no amount of money can get you a better Coke than the one the bum on the corner is drinking. All teh Cokes are the same and all the Cokes are good. Liza Taylor knows it, the President knows it, the bum knows it, and you know it.”

Running as release.

Posted: July 13th, 2010 | Author: | Filed under: General | Tags: | 1 Comment »

I’ve been running on and off for a couple of years now. I’ve been prone to injury so I have probably spent more time off than on which makes everyone I know ask me why I continue. I run because it’s an enourmous release.

Running for me is a cure-all. When I’m feeling stressed or angry I find that running makes those feelings of frustration disappear. I can have had the worst day/week/month but an hour around the track with nothing but me and the clothes on my back puts everything into perspective.

Running gives me time to put problems into perspective, to realise that everything is surmountable. It also reminds me of how resilient my body is and that while it’s often easy to quit the greatest rewards come when you push past the pain point.

Running is a time for self reflection disconnected from everything else. There is no one nearby to talk to me or interupt me; there is no Twitter or email or phonecalls; there is nothing.