Software Assisted Sustainable Ventures

note: this is a long one – and a genuine request for assistance – so make yourself a cup of tea, put on some krishna das and put your feet up – you might be here for a while ….

Building a game-changing sustainable enterprise requires much more than yet another ‘good’ idea. It requires a combination of genius, pragmatism, and sheer bloody-mindedness. It requires a willingness to sacrifice certainty and short-term financial gains for the long-term benefits the project will bring to the individuals, organisations and communities you are seeking to serve (including yourself). It requires enormous flexibility and agility and the willingness to make use of whatever tools are immediately at your disposal – trading up to new ones as you can afford them, or the existing ones have been worn out through over-utilisation.

And thus it is with w1sd0m – a venture I’ve been blessed to be involved with since my first trip to Boulder last year, and the primary reason why I flew back here in January (sans my remarkably sanguine, beloved and yogic wife Georgi). I’m now working on something that I firmly believe will represent my own life’s work better than anything else I’ve engaged with throughout my entrepreneurial history. The other ventures we’ve established continue to grow (and I’m in prelaunch for wellnessconnect, icologi and uncompromise here in the US), but this one, really, is the one that keeps me up at nights, working weekends and generally feeling as if there is no great sacrifice to ‘not having a life’, when the work we’re doing is about enabling thousands of other ventures to guarantee millions of others a life at all.

The purpose of this post is simple – we need new tools to grow this enterprise.

We started with a bunch of things (listed below) and now, as a result of that, have come to a much better understanding of what our requirements are. We’re a rapidly evolving organisation, taking the principles of Agile Software Development and applying them to business development. Where we started by asking ‘what tool do we need to achieve a specific outcome?’ we’re now at the point of asking ‘what tool suite do we need to run the entire organisation?’

So I’m not looking for comments on a particular tool, but on what we are proposing as our toolset – an entirely different question. Our decision making process and requirements are outlined below, as well as the tools we’ve tried and dropped, and the ones we think are the ones that we need.

Hopefully this post and the ensuing discussion will be useful for anyone seeking to build a more sustainable venture by leveraging existing software and hardware solutions in a cost effective, intelligent and adaptive framework.


Our needs over the next twelve months are going to be substantially different to what they are at maturity. We are building out dozens of projects with hundreds of milestones and thousands of tasks. Our team are distributed (not all in the one office, timezone or even necessarily country). We need to be nimble and adaptive, and as much as we are looking for an integrated and sophisticated toolset, we don’t want to get bogged down in something so fine-grained that it takes the team a month to upskill. To that end, UI (user interface – not just what it looks like, but how it operates) is of high importance. As is the ability to work mobile, especially on iPhones or iPads (although I still think that the lack of ability to play flash and the absence of a camera on the latter device are an inexcusable oversight on Apple’s part … just sayin’).

In short, we need something that just works so that we can keep moving.

The primary criteria by which tools are assessed seem to be:

  • open-source (generally free and configurable) vs proprietary (closed system, monetized through subscription fees)
  • open (has an API for connecting other applications to) vs closed (no API, no way to plug in your own applications; we’re not going to get into this here, because a closed system should be an absolute deal-breaker for anyone who’s serious about having the freedom to determine how best to operate their own organisation)
  • internally hosted (on a local or remote server) vs SAAS (software as a service – web-based applications)
  • free(mium) vs paid

The comments below are not general to the criteria above, but specific to what we think we need for our ongoing development.

open source vs proprietary

We’re huge proponents of open-source – for both philosophical and practical reasons. Yet having said that, we’re pretty much all working on mac’s and iPhones (Apple being the most successfully marketed closed-system hardware and software developer in the world), and those who aren’t, are on PCs running Windows. Yes – we’ve tried installing Ubuntu (am writing this post through Firefox on Ubuntu installed as a virtual operating system on my mac; running through vmware, a proprietary virtualisation tool), and despite the fact that Linux is generally considered to be the most intelligent and secure OS, try finding someone with the time and experience to not only get it up and running, but to learn how to use it and manage it (adoptability vs adaptablity) and have the software you’re using seamlessly translate across multiple platforms (ever seen what a NeoOffice or OpenOffice word doc looks like in Microsoft Word?)

open source benefits open source costs
  • free
  • highly innovative
  • distributed development
  • extremely open API
  • highly flexible due to large numbers of third-party plugins
  • can be slow to deploy a feature-rich set due to required investigation on plugins
  • stickin’ it to the man
  • not generally enterprise ready (out of the box)
  • requires heavy customisation
  • unpredictable development pathway
  • leverages core functionality through third party developers
  • plugins often not updated for future iterations (lack of monetization a frequent disincentive to keeping software updated)
  • toolsets generally limited (due to lack of commercialisation incentive)
proprietary benefits proprietary costs
  • works out of the box
  • (generally) predictable development pathway
  • (generally) stable and reliable platform (if somebody’s paying for it, you’d better make sure it’s working)
  • rapid to deploy for roughly 90% of an organizations needs
  • third party plugins typically created by commercial software developers (hence robust)
  • financial expense
  • functionality (generally) restricted to what customers will buy (as distinct to what might be useful)
  • innovation restricted to company’s development team and imagination
  • API’s are sometimes restrictive (or non-existent)
  • philosophical mis-alignment

our conclusion: proprietary is more robust, extensible, scalable and reliable

internally hosted vs SAAS

I have to admit to having a bias here – one that comes from having worked with both solutions. I’ve deployed and relied upon both Mac and Windows servers (and one of my clients, a gold-certified Microsoft Partner informed me that they run all of their internal Windows servers virtualised on a Linux platform ‘because it’s more stable’!), and have recently switched over to SAAS. Ultimately, my greatest concern relates to hardware failure, and the costs of having true disaster recovery to mitigate this risk (triple-redundant onsite and offsite backups for local servers as well as fully functional hardware standing by for swapping out in part or in whole, combined with the costs for IT management whether internal or outsourced). To speak plainly, I will never deploy a Windows server again …. ever. The costs seem to far outweigh the benefits, and let’s face it, Microsoft is like the Borg of software – if they didn’t create it, they will assimilate it and destroy its soul along the way ….

internally hosted benefits internally hosted costs
  • tight control
  • data security
  • customisation
  • data speed (if hosted within office)
  • setup costs (hardware + time)
  • disaster recovery costs
  • maintenance costs
  • upfront licensing (if proprietary)
  • setting up & supporting remote users requires IT team
  • client-side issues (hardware, software and capability) cannot be mitigated
SAAS benefits SAAS costs
  • speed to deploy
  • low setup costs
  • affordable mobility
  • backups and maintenance outsourced (and costs absorbed within licensing fees)
  • highly & quickly scalable
  • often online only (loss of internet = loss of tool
  • limits to customisation
  • data security concerns (not necessarily valid, but consume mental bandwidth)

our conclusion: SAAS is cheaper, faster, more scalable, more reliable

free(mium) vs paid

We’re all cheap, let’s face it. Who wants to pay for something they don’t have to? Entrepreneurs – unseasoned by the practical concerns of growing an enterprise – will typically shoot for the free versions of tools as frequently as possible. How many people do you know who have a paid LinkedIn subscription, for example? And free is good … for as long as it is. Paying for a service is sometimes a bitter pill to swallow, but the reality of paying for something is that, more often than not, instead of focusing on software, you free up your time to focus on your venture. You don’t need to be a software engineer to launch a social enterprise – if you want to be of service, you need to be intelligent enough to recognise that, if you expect to get paid for doing what you do, maybe you should expect to pay to maximise your leverage. Freemium is always a good way to test out a platform, but most platforms these days will provide you with a 30 day free trial of fully functioning software; if they don’t, it’s highly likely that they’re out of touch with commercial reality.

There’s no cost-benefit analysis to do here – you either pay, or you don’t.

our conclusion: paying for a service from a reliable vendor provides you with rights you don’t get from a free service; money buys attention (and a certain level of professionalism) from your vendor of choice

our overall conclusion is that we need a proprietary, SAAS solution that we are more than happy to pay for


mail & calendaring: google apps premier provides robust IMAP email and CALDAV compliant calendaring which means, in essence, that your data is stored on their servers and can be mirrored down to your computer and mobile device without the attendant concerns of ‘what happens if my machine is stolen or the hard drive fails?’ In short, local backups become a thing of the past. Why do we like this solution? Because, in short, for $50 per user per year, we make Google our software partner, and can eliminate hardware and software failure concerns as they apply to our email and schedules (the lifeblood of  our day to day operations). And let’s face it, if Google fails, I’m pretty sure we’ll have bigger things to worry about than the fact that we can’t access our email ….

scheduling: like many entrepreneurs, we run multiple calendars; I have a calendar for my companies in Australia and one for w1sd0m; virtually everybody on our team has a personal calendar and a w1sd0m calendar. So how do you effectively schedule meetings, knowing what your team’s availability is, without having to let everybody in the organisation know that you have an appointment at the clinic? Tungle, is the short and simple solution that every organisation needs. It allows us to see our entire teams availability in a single view, quickly and easily schedule meetings with each other and, the bit that we really love is that people can propose times for appointments directly through the web interface, which saves the usual back and forth on email and phone trying to coordinate meetings. Best of all, it’s free so there’s really no excuse for not using it.

document collaboration: google docs (via google apps premier) is a long way from the perfect tool, and I won’t go into cataloguing it’s shortcomings here; the advantages are obvious … you get an online document that can be shared with anyone with specific permissions for each user role (editor or viewer); further, the capacity to work with your online documents offline through either Googles Gears (Safari & Firefox cross-platform) or the OffiSync integration with Microsoft Office (PC only) means you have a fully functional ‘free’ synchronisation tool for whatever documents you choose to work with in this manner

mindmapping: there’s dozens of tools out there for this; we are currently using Mindjet MindManager – it’s cross platform, has great UI, and, put simply, just works (there’s also an iphone app, but it’s a little tedious and slow on the 3G and I don’t really use it much) and have been experimenting with their online Catalyst tool; at close to $300 per user, however, you need to be serious about this, because it gets expensive the faster you scale ….

document storage: google docs is our current solution because each user gets 25GB of storage and you can upload any document of any type. There are third party plugins such as memeoConnect and and EpicenterDMS that will permit you to synchronise local folders with remote folders, as well – reducing even further the need for local backup solutions

It’s highly likely, however, that we will switch over to the even more robust and extensible combination of Jungle Disk Workgroup and RackSpace Cloud Files in the not-so distant future due to automated synchronisation, scalability and the more sophisticated nature of these tools.

project management: manymoon is a google apps enabled project management tool. We’ve been working with this for a few months, and whilst we like the general trajectory of the tool, and the responsiveness of their support, it’s not right for our requirements moving forward. They’re a company to watch, however, and if you’re looking for a simple tool that will work for a small and relatively mature operation, or even a way to manage all of the various domestic projects that seem to keep cropping up (unless you need the excuse of not having fixed the garage door because it slipped your mind) it has a lot to recommend itself.

We’ve discovered a couple of deal-breakers that are worth being aware of if you’re considering going down this path, however:

  • data portability – there is currently no export function, and no indication of when it will be implemented; for an organisation that is seeking to scale, you will be tied to their development pathway for an undetermined period – in this day and age, we consider vendor lockin to be inexcusable, and are disappointed by what appears to be a significant oversight on the teams partmobility – whilst SAAS, there are no apps of any description to plug into your projects and tasks through a mobile device
  • mobility – there are no apps to provide you with access to projects via a mobile device (sure, you can access it through a web browser, but the speed and reliability of the connection is a major drawback to even attempting to use it – think AT&T if you’re on an iPhone and you’ll understand why)
  • extensibility – the system does integrate with google apps (a huge plus if, like us, you are using the premier version to deliver mail, calendaring & collaboration docs), but it does not integrate with other vendors outside of this framework (eg. we’re trialling FreshBooks – also google apps enabled – as an invoicing & billing platform, and there is no way to plug timesheets directly into billing)

CRM: zoho CRM works, to be sure, but the interface is not particularly enjoyable, and the costs to expand it out beyond it’s existing service make scaling a significant issue; having said that, it’s a robust and effective solution that draws its greatest strength from being part of an overall suite of products developed by ZOHO that might well be the holy grail for a small and growing venture’s SAAS requirements


  • google wave – an interesting idea that was supposed to revolutionse online communications (and still might) if google will only remove thumb from butt and do something about integrating wave with google apps premier (after all, what’s the point if you can’t use it within your organisation?)
  • ZOHO wiki – the tool works, sure enough, but the multiple logins across different applications was the real killer here – that plus the inability to post from email, or direct from web, and create discussions on the basis of real time information
  • google voice – we haven’t actually abandoned this (I’m still using it within my own companies because I’m both here and in the USA, and don’t want to get stuck with one number) it’s more that we’ve chosen not to deploy it due to the fact that, like the wave, it doesn’t integrate with our apps premier account.


As mentioned at the outset of this post, we’re looking for a robust, scalable, cost-effective SAAS solution; one that, as much as possible, binds in together so our team are not having to manage multiple logins or learn multiple different platforms. The types of tools we need are:

  • enterprise standard email and calendaring
  • project management
  • CRM
  • document storage
  • document collaboration
  • integrated messaging
  • wiki / pages / forums etc
  • email marketing (not essential, but helpful)

Thus far, it seems, there are really only two contenders that will provide us with what we’re looking for – ZOHO or 37signals (creators of BaseCamp) in conjunction with our Google Apps account. We are also investigating some of the Agile relevant tools – such as Rally, Nozbe and Atlassian – but find that they are largely designed for software development (which we’re obviously doing) and seem an imperfect fit for our general business needs.

Zoho’s toolset is comprehensive and definitely covers our requirements. Their UI is ugly, however, and the sophistication of their tools creates the potential for confusion in the less software-savvy user. We’re on the fence about this as a result.

37signals’ toolset seems to be slightly less sophisticated than Zoho’s, but appears to have been developed with usability in mind, and a thoroughly enjoyable Web 2.0ish experience. Because it’s an easier toolset to get one’s head around, we’re leaning strongly towards them.

We’re not wedded to the Google Apps solution, of course, but until we can find another Exchange ‘replacement’ that doesn’t require us to deploy our own server (a path we don’t want to go down for all of the reasons listed previously) and that has the scalable and affordable data storage capacity Google gives us, we’ll be sticking with it.


Thanks for sticking with this … if you made it this far, you’re a smarter man than I am, Charlie Brown ….

As I said somewhere further up the line, hopefully this post will serve two purposes – to both illuminate to anyone wanting to use software in service to their sustainable initiative and provide us with some useful feedback along the way.

If you’ve got something to say about this, please share via the comments rather than contact me directly – aggregating w1sd0m is about ensuring that we all get to benefit from the discussion.

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