Blogging with a computer

I am in Las Vegas for the next couple of days, here to celebrate with my friend Tara Hunt her birthday. She has brought together a group of her friends from all over the world and together we are spending sometime in what is perhaps my least favorite city but much improved by the company of friends.

As I packed for my short trip I debated about whether or not to bring my new MacBook Pro with me. It is a fantastic new machine and working on it still feels more like play than work. But if I had brought it I would have to watch it, would have to secure it when I joined the group at a cabana by the pool or went to a show (Ka tomorrow evening).

So instead I decided to only bring my iPhone 4 (along with bumper case – I haven’t had any antenna problems other than AT&T’s usual horrible service and dropped calls). I didn’t even bring my trusty and fairly new Panasonic Lumix.

As you can see from the photo, taken of the Irish band that played while er had dinner this evening, the iPhone 4 does indeed shoot well in low light and with the right apps – such as the WordPress app I’m using now – is a very powerful tool for new media creation.

I don’t know how many more posts I’ll write this week – mostly this is a vacation and though every move is likely documented by cameras, tweets and foursquare checkins in this particular crowd my focus this week is on catching up with my friends and making new friends.

But as I work on a new venture around helping game companies (mostly online social game companies) make more money there are a lot of lessons big and small I am seeing in how casinos (ie “gaming”) work here in Las Vegas.

Where the gaming is a bit less social though the social aspects are important and where the rewards are mostly very simple – cold, hard cash.

But I can also see that with casinos such as the Mandalay Bay Resort gambling is no longer the only (and indeed perhaps not the major) source of revenues for these establishments. Clearly food, drinks and entertainment as well as the hotel rooms themselves are now also significant revenue streams and may actually often be more profitable than gaming.

I haven’t been back to Las Vegas in a few years I think it may have been nearly four years and even in that short of a time it is clear that a lot has changed. As I sit here writing this post I am seeing a lot more people dressed (well barely in the case of many of the women) for a nightclub.

At the same time the poker rooms I have passed have been very full (since the World Series of Poker (wsop.com) is ongoing this doesn’t surprise me. But while much of Las Vegas depresses me at least with poker real actual skill is present.

I may try to catch some of the WSOP tomorrow after I tire of lounging poolside or swimming.

New podcast subscriptions for February 2010

At the beginning of the year I posted the state of my media diet in 2010 and based on that post have received a lot of great suggestions for additional podcasts and other media which I should add to my diet in 2010.  I’ve also found a bunch of new podcasts through searches of iTunes directory and via referrals from other new podcasts which I have subscribed to recently.

Here is a list of new podcasts I subscribed to in January and earlier this month. In each case I have also added the feeds to Google Reader which includes many non-podcast blog posts.

• Dragons Landing – One of a number of gaming related podcasts which I have subscribed to recently. I’m undecided about this show which while interested and well produced does tend towards being a bit long.
• Robertson Games podcasts - One of a few podcasts I have subscribed to which are podcasts of live play sessions of role playing games. I really like the blog these podcasts are from, but am uncertain about the live play (in part because it tends to be, so far at least, just a single one-shot game)
• Icosahedraphilia - a long running live play podcasts of a D&D 4E campaign. Very well produced and the game is interesting, if a bit a tame language wise due to the players & DM’s personal religious beliefs. Really fascinating for the detailed descriptions of the props and resources used in the course of each game.
• The Tome Show – A reviews and interviews show about role playing games. Very well done though I have only listened to a few shows so far.
• NPR Planet Money Show – A show I have been meaning to subscribe to for some time now as I have really enjoyed the episodes of This American Life which have featured the team behind the Planet Money podcast.
• Studio 360 with Kurt Anderson (blog) – One of the two most recommended shows in the comments and responses to my initial post. So far I have enjoyed this show but have found that I listen to other podcasts before catching up with this one.
• WNYC’s RadioLab – The other most recommended show in the responses to my initial post. A show about science but presented in a very intelligent and engaged way. That said, I also find myself listening to other podcasts before I catch up with this one.
• Huffduffer (personal feed) – not a podcast in a traditional format but rather a service for handcrafting a podcast feed from audio content available online. My friend Marshall Kirkpatrick at Read Write Web wrote up a glowing review of Huffduffer and based on his recommendation I checked out the service and signed up. I have, so far, found it to be a great way to quickly and easily create a personalized feed of various bits of audio content I find online and want to listen to on my iPod.

So still haven’t found any tech podcasts to subscribe to but I have added a great deal of new content to my podcast listening diet. I welcome suggestions for other media I should add – podcasts, video podcasts, magazines or other media forms & experiments.

What do you actually use your computers to do?

Last night I wrote about why I think the iPad will be a great device for content creation – and included a number of potential million dollar plus ideas.

Today as I read a bunch of blogs and articles covering the iPad I am struck by how many people who are objecting to the iPad or predicting that it will fail seem to have some idea of computer usage which differs, dramatically so, from how I have used my computers for the past decade and very much from how I use my computers today.

The image that people have of “using” a computer seems to involve lots of overlapping processes, deep customization of the system and a variety of applications running which all push the limits of the system.

My reality?

I usually have one application running on my computers – a browser. On my tablet I currently use Google Chrome as my primary browser (not least of which because it doesn’t have lots of extensions and thus loads quickly and smoothly).

Recently I have been using Mindjet’s MindManager (I have the old 7.0 version installed here) which I enjoy but really only barely use, mostly I use it to capture all my various ongoing projects, to-do lists and the like (in short as my electronic GTD system).

Occasionally I use an IM application, mostly Google gchat – which I could just about as easily just use from within the browser, though I do appreciate the occasional notifications that pop up about new messages in my primary inbox. Though since I have at least three main email addresses and only get notifications for one email address and then only for my inbox and not for the many important messages I get but autofilter into various labels, the utility of this notification service is minimal at best.

And when I sync my iPod and iPhone I fire up iTunes – but since my library is vastly larger than my laptop’s HD, doing so requires that I attach an external HD to my system for the syncing to work. I use a wide array of complex smart playlists to result in every device I own and sync getting exactly the content I want to reside on that particular device – which always includes the latest podcasts I have downloaded as well as any other new content I have recently added to my iTunes library (so if I buy new content, rip a CD or download legal digital content it will get onto my music player automatically and be added to the primary playlists I use to select what to listen to during my walks, waits for buses and other podcast listening opportunities during the day.

But that is about all the applications i use on a regular basis. Sure, I have some compilers installed on my laptop, the full MSFT Office suite and much more but the reality is that I almost never need to run any of these applications. And when I do other than looking up information in my browser from time to time, I rarely need to have multiple applications open at the same time – for one my screen resolution though good for a laptop is still so low that I almost always run every app I use in full window mode.

Perhaps I am missing something major about how people use their computers today – some suite of applications that everyone other than me uses – but I don’t think this is the case.

A few possibilities.

1. Photo & Video editing. My digital camera died a few months ago and I have yet to replace it (need a camera but don’t have the spare funds to buy one at the moment) so I don’t do a lot of photo and no video editing. But there are some great online alternatives to applications such as Photoshop. Aviary is my personal favorite – they offer a wide range of image and vector art online editing tools along with even some music editing tools. Adobe even offers an iPhone application for Photo editing (limited but
2. Games. I don’t have powerful enough video cards in either of my computers to do much gaming (definitely not in my tablet, my iMac could handle a bit more though there are far fewer MacOS games to select amongst). But PC gaming is and likely will remain a big deal. But so too is gaming on the iPhone and in the future on the iPad and I suspect very rapidly the iPad will attract games that may be better in many ways (or at least very uniquely different) than games not just on PC’s but even against games on any of the major game console systems. I predict that the iPad will be a gaming platform as big, perhaps bigger, than the current game consoles (not their portable game systems which the iPhone already is a potent competitor to but also the main game consoles – Wii, Playstation3 and Xbox360)
3. Personal Finance. Here in the US we have started to shift into preparing for Tax season shortly. I know in the past many years I have used TurboTax in some form to help prepare my taxes and that many friends run software such as Quickbooks for their family finances or small business finances. That said, there is a reason why Intuit bought Mint last year. Finance software including tax preparation and small (and large) business bookkeeping is rapidly moving from local computers to web/cloud delivered products.
4. Customized “run the business” applications. These vary by business but think the Point of Sale systems in a retail shop or restaurant. Even here, however, with the rise of platforms such as Square there are many opportunities for many retail transactions to move to the cloud & mobile applications.

So what uses of your personal or business computers have I missed?

Social game ideas – open ended, multi-sponsor ARGs

My background in games and the current state of things

I have been a game player since my grandfather taught me to play chess at the age of 4. In my youth I played AD&D, Shadowrun and many other role playing games – usually at the DM. At my high school there were a bunch of us who played all types of games on a regular basis, we played many boardgames after school, had AD&D campaigns including one we ran at times over lunch in the cafeteria and were regulars at the local games shops.

In fact the father of one of my high school classmates was a professional game designer at the time for Mayfair Games where he lead the development of many classic board games, games such as Cosmic Encounters. A number of us, myself included, occasionally were drafted as gametesters for new board games.

At the local games shop, a massive, custom designed building built by a serious historical minatures gamer, we would spend hours many evenings and weekends playing a wide range of games, including historical minatures, roleplaying games and all types of boardgames.

I always assumed that I would stay playing games on a highly regular basis when I entered college but that didn’t happen, somehow I didn’t stay as active a game player, though I did play the occasional game of chess and lots of card games with friends.

In the 90′s I spent many years as literally a professional Magic the Gathering player and dealer, in one year I earned over $40,000 trading pieces of cardboard and won prizes valued into well over $5,000 in many tournements which I often won or placed very highly. Friends of mine were even better, winning at a global level and traveling around the world to play Magic the Gathering (and winning well over $10k from some tournements in the process). I quite my regular job at the time when I realized I could make far more money in a few hours than I would earn in days.

A bit later I also became active in a range of Live Action Role Playing games, mostly around White Wolf’s World of Darkness game. The game I played started in the mid-90′s in Chicago, grew rapidly to include nearly 100 games in cities all around the world all sharing a common set of rules and world and which allowed players to play their characters from one city at the games held in other cities. As a result players could and did interact across continents (friends of mine went to Brazil to play the game) and there were games happening multiple times every week near to Chicago.

It was  great fun – immersive and engaging. While we did play in spaces we reserved just for ourselves (we would contribute to rent spacees from time to time) we also played in the midst of other events – often in nightclubs, once very memorably at the Chicago Museum of Modern Art when they stayed open for 24hrs to celebrate the Summer Solstice. Playing in the midst of 100′s or even 1000′s of people who were not playing the game added layers to the interactions and was extremely fun.

In the past few years Alternative Reality Games (ARGs) have become increasingly popular and successful, though with some notable caveats. Most, though not all, have been run as commercial promotions for a specific event or product – very often a movie or TV series. Currently the upcoming movie District 9 for example is running an ARG where you can play either a human or an alien in the world of the movie.

The model of ARG’s has become in some ways fairly formalized. They start with a series of clues usually embedded inside of something in mass release – billboards & posters, movie trailers, occasionally other forms of advertising. The clues in these ads, often a phone number or a web URL lead a player to signup to the ARG. From there a series of clues lead to other sites or phone numbers often with embeded small games or challenges.

Over time additional clues are released which further the ARG’s storyline. For most ARG’s the model has become a bit of a funnel, with fewer and fewer players continuing as the puzzles are released, usually these ARG’s lead up to a final end clue and often the players who figure it out in time arrive at an event or get a prize of some form (a sneak preview of a movie for example as well as other gifts & prizes). Then often the ARG comes to an end as the movie or TV show is released (or the season ends in the case of ARG’s such as Lost’s or Fringe’s where there were clues embedded inside of each episode).

These games are effective ways of engaging and building fans for a new media property but they have many unfortunate side effects of this model.

1. They generally are less and less engaging for new players as they grow in complexity – sure most of the time players set up Wiki’s or other sites to explain what is known so far, but as the game goes on it becomes less compelling for new players – and once the final reward is given out it often is far less interesting to new players (and even existing players may cease engagement)
2. While some ARGs have included a wide degree of player driven content & storytelling, for most there is a very heavyhand of the ARG designers at work in telling the story and though players can visit many parts & sites in any order they want there tends to be a very linear path of the story being told by the nature of new clues being released on a specific timetable.
3. A few ARGs have had occasional “real world” events but the global distribution of most media for the most part means that most ARGs now primarily employ mass media & the Internet for the game play (also often voicemail/800 numbers for some parts and frequently SMS messages to players).

A few weeks ago a variation of a type of game which has been popular for a few years inside of social networks such as Facebook was released on top of Twitter – Spymaster – these games build upon usually preexisting social elements and relationships to form part of the game play. In the case of Spymaster your twitter followers become the size of your “spy ring” and you gain game play advantages by having more of your followers also playing Spymaster (they become “spymasters” in your “spy ring” and give you game bonuses).

Add in the fact that social tools such as Twitter (or Facebook) have many ways for you to communicate with people – and the games take advantage of these tools to send out messages about your game play activity to your social network (with your permission) and not surprisingly these games can and do often experience rapid, exponential growth as large networks of friends all start playing.

However while fun games such as SpyMaster or the multiple Mafia based games on Facebook (and in those cases now also with iPhone apps) suffer from (but also benefit from) a fairly simple game play and room for interactions between players. They offer only relatively limited sets of actions, have constraints on what you can do in a given period of time, and allow for only a handful of direct in game ways to interact with other players. Though often players evolve ways alongside of the formal game play elements to interact. In the case of SpyMaster many players have set up Twitter accounts only focused on playing Spymaster and have builtup networks of followers with whom they coordinate in game actions and for strong in game cliques.

I play Spymaster and enjoy it, though it is a relatively lightweight game, so I only play for a few minutes most days, if that. They haven’t yet settled on a business model, but it should be noted that some of the Mafia games on Facebook are already part of game companies rumored to be rapidly approaching over $100M/year in revenues, primarily through the same of virtual currencies to game players to use to enhance their game experiences.

A few players of SpyMaster are starting to expand the game via sites such as SpyMasterFans. There they are forming groups, sharing ideas & insights into the game, challenging each other to new interactions etc.

You may have noted that in my recounting of my own game playing background, I have not mentioned a lot of computer gaming. In the early 1990′s I ran a Muck (think an all text based version of Second Life) but I never got into computer gaming very much. So I haven’t played, though I do follow, the rise of social computer games. At present there are two very important models of social computer games.

1. Massively Multiplayer Online Games (mmog’s) most famously World of Warcraft (or WOW) but also dozens of other games from companies around the world. There are three primary models of MMOG’s – subscription (usually with regular expansion packs as well) – this is WOW’s model and is the most common, free to play but game and expansions needed (Guild Wars is one of the few that use this model) and the newest model free to play including the software but virtual goods & items available for purchase (Sony’s Free Realms uses this model though subscriptions are available with additional benefits).
2. Server based games. Increasingly console games as well as many PC games have multiplayer options and game companies are now often offering services that both run server instances and help players find other players to play against. Microsoft’s Xbox live for the XBox 360 and Valve’s Steam service for PC games are two examples of these game services. Often a fee is required for membership (for XBox live) and in most cases the games have to be purchased to play them.

There are many further nuances to computer and console games. For this post the most crucial of which is the number of players they are designed to facilate interactions amongst and the length of that interactions. Console games often are limited to a relatively small number of players competing against each other (4 vs 4) which can be over the Internet or over a local area network. MMOG’s differ in how many players they handle interactions amonst – many have multiple “servers” which are different instances of the world and which may have slightly different game rules, meaning that in most cases players on one server do not interact with players on another so they are limited to the number of players who choose to play on a given server. Some games are designed to encourage cooperative play where players cooperate together to achieve game goals (WOW has quests that can involve 40 or more players from a single Guild working together). Many games also have elements of player vs player interactions where players fight directly against other players – depending on the game this could occur anywhere in the game world (on a given PvP server) or in many games may be limited to a specific area of the game.

Some ideas for the future – open ended, multi-sponsor ARGs of a new form

While I know that computer and console games have many incredible aspects offering amazing graphics and game play capabilities they also have in-built limitations. Even with voicechat which is increasingly an important part of the player to player interactions in many games playing such games is limited to players who have the required equipment and financial resources to buy the necessary games & game subscriptions.

So here are a few ideas I have for where social games could go in addition the ongoing evolution of computer & console games.

Instead of an ARG which is sponsored by a single media property – and which is thus usually tied to the world of that particular movie or tv show (or less often an artist such as NIN) I would suggest a game with the following models & business elements.

• A combination of lightweight, easy to adopt technologies AND frequent, multi-city live interactions & events. Neither element would be necessary to enjoy the other but if you used both your game play enjoyment would be enhanced.
• The technologies could leverage and be built upon existing social tools such as Facebook or Twitter but would likely have a website and perhaps mobile applications as well
• Much of the world and game interactions would be driven by the players with a light touch of the people designing and running the game – they would mostly design the world & backstory and would occasionally facilitate in game activities and elements, but the game would be designed for the players themselves to evolve the plots & ongoing stories.
• In place of a single sponsor driving the event to a particular end point the game would have sponsors that come and go and which interact with the game in a variety of ways – I could see some sponsors embedding story from the game into their media (tv shows perhaps even movies) while others would provide real items and help support game related events in the “real” world (as well as having in game repurcussions). These interactions could at times be lightweight – having characters from the game (probably mostly actual player’s creations) who appear in the background of a movie – say as items in a newspaper story – this would I think be a lot of fun for players – and great marketing for those movies or tv shows.
• The game would be designed to allow for new players to join at any time and for players to play at a wide range of play cycles – some playing daily while others playing only a few times a month or taking a summer off and resuming months later. This takes careful game design to balance and to give everyone a lot to do without the game becoming boring for anyone – but it suggests that for the most part these games would only have light elements of “levels” or the like but heavy elements of role playing and interaction. Though there could also be puzzles and cooperative quests so players uncomfortable with heavy roleplaying could ease into participating in the game as well and be rewarded for that interaction.
• The business model could include clues & game elements embedded in physical items (t-shirts, trading cards, books, comic, digital downloads of many forms etc) which is a model that other similar in some ways games have already used quite successfully. Some of these products could be from sponsors who not only embed game elements in something they sell but also support the game finacially & through promotional efforts.

So that is the basic ideas – I haven’t yet designed an entire game example just started thinking about this, if it sounds like fun (or if you know of examples I should take a look at) please leave comments or contact me privately.

What is a business designer or how to work with Shannon

Of late I have started to describe myself as a business designer in response to the usual question of “What do you do?”

But what do I mean by the term?

A Business Designer, as I intend the term, is someone who uses the techniques of design firms, such as IDEO, to design new businesses – whether entire new startups or within the context of an existing, larger business.

I have been highly active online since 1991 and working on the web since the mid-90′s so a great deal of my work does involve the application of technology, especially web technology, to business problems. However my process starts before deciding what the solutions will be, it starts with the discussions about the specifics of the business, the resources available, and objectives.

Only then do we address the specific solutions required, in many cases applying technology both purchased, open source and customized to the business objectives.

So what is my process?

Earlier this week I attended the SanFran Music Tech Summit and over the course of the fantastic conference I had many long conversations with entrepreneurs and business people who were attending the conference. In these short conversations and discussions I practiced a shortened version of my business process.

1. Hear how the current business, or the business idea, is described today.
2. Explore what is behind the business, what technology if any current exists, what are the current clients, what is the current business process.
3. Get a quick sense of the business objectives of the team at present – new customers, investment, partners etc.
4. Brainstorm. In this process I leverage the diversity of industries and companies I follow closely, seeking examples often from unrelated industries which can help us decide on direction and business models for the business.
5. Make concrete suggestions of next steps for the business from simple text copy changes to complex shifts in business model.

That is the shortened process, at times taking only a few minutes, other times taking an entire lunch.

What I follow

At the moment I pay very close attention to a number of industries and technologies, these include:

• The music industry, especially the emergance of the online, digital music industry.
• “New Media” from the business models of old media applied to the new digital world to the emergance of new businesses and media leaders
• Web 2.0. I define Web 2.0 as the shift to a data centric view of web applications. Practically this means more open web sites, api driven services, dynamic flows of information, and in many cases user generated content
• Mobile applications. In particular I have been an early adopter of smartphones, currently heavily focused on the iPhone.
• Gaming. Though I am not an active game player, I have a longstanding and deep interest in games and gaming. I’m very interested in the application of gaming elements to serious purposes.
• Social Networks. I started Meshforu, a conference on the study of Networks in 2004 and have been an early adopter of online social networks. I also follow closely the academic study of Social Network Analysis as well as related fields of Network Science.
• Advertising. I believe that advertising, across all forms, is in a major transition. In particular I am a passionate proponent of Brands and believe that brands need to adapt to the new, digital landscape
• Internet Radio. While I follow the whole music industry closely, many of my current ventures relate to the new forms of Internet Radio.
• Community. Most successful businesses are driven by a community both online and offline. I’m an advisor to a number of startups focused very much on the support of specific communities enabled by the new digital media world. In many cases these cross over many types of media including online websites.
• The Food Industry. My father is a leading food technologist who has designed new products and business processes for most of the major food companies around the globe. I am a passionate foodie and follow emerging trends in the food industry, including restaurants very closely.
• Social Entrepreneurship. I run a small non-profit, MeshForum and am passionate about new models of business which include a strong social mission and purpose.

There are many other industries and specific technologies which I also pay attention to on a regular basis, I have worked for some of the largest banks in the world. I’ve also designed and build AI driven automated data applications and other complex pieces of enterprise software. But at present the above list of industries are the ones I follow most closely and where, primarily, I seek clients.

How I work

My preference is to work with clients over an extended period, typically via a monthly retainer with at least a three month minimum. In three months any business whether large or small can see specific results from the engagement. A retainer, instead of the more common hourly or day rate, allows for the wide range of ways I work for and with each client.

For most clients I will meet with the client, often onsite for a series of meetings and observations each month. I am often a part of internal discussions and meetings with partners and external vendors.

I am based in San Francisco but will work with clients anywhere in the world, combining in person meetings with extensive online collaboration.

Every engagement is different but a few specifics you can expect from working with me.

• New Ideas – a primary part of my job is offering a new, interdisciplinary perspective on the challenges of your business. A key part of this is carefully suggesting specific, implementable new ideas and approaches.
• Simplification - much of my practice is around paring ideas and processes back to identify what is most key and value creating. Many startups, as well as large companies, build technologies and processes which are overly complex. By focusing on simplification we end up with greater value.
• Clear processes and designs – After we have focused and defined clearly the specific business objectives, my role shifts to achieving those objectives. There my job is to define and often help manage the business processes, including working with development teams, to build and design the related parts.

I have over a decade of experience as an Open Space Facilitator and use that as part of my consulting. The result of a facilitated open space event is usually clearer understanding of both the business opportunities and the resources available to address them, as well as focused groups of employees (and often external partners including customers) to address each business need.

If you are interested in working with me, email me at shannon AT nearnessfunction.com or call me at 1.800.454.4929.

Evaluating the Cloud – first impressions

In theory I am a huge fan of and proponent of moving towards cloud computing, in practice as I look at currently available options even I find the curent landscape confusing, a bit convoluted, and rife with decisions and options. 

Though I can program (in lots of languages) I am mostly an strategic consultant and business advisor, so while I do have specific technical requirements to look at, this article will mostly be written as a record of my process of evaluating cloud computing options from a business perspective. For a good, though incomplete, starting point for looking at cloud computing options from a more purely individual developer perspective IBM has a great article on current clound computing options. 

As I have noted many times on this blog and on my twitter I am not a fan of Microsoft Vista (I consider it the worst OS I have ever used in some 25+ years of using computers). Though I have managed fairly large scale Miscrosoft servers in the past, I am also not a fan of Microsoft centric solutions for web applications – I don’t use Visual Studio as my primary development platforms, I would never encourage a client to build a web application that requires IE. So while Microsoft Azure is a cloud computing option I am not going to consider it in this blog post.

There is a more practical reason for this as well, as I write this, Microsoft has not yet announced the costs of Azure and it is currently only a Community Technology Preview. Without this data or a production ready environment Azure is not a responsible choice for a startup nor for a new venture which will be used in production of a larger company. 

So what factors will I use to evaluate cloud computing options? And then what are my initial conclusions?

Factors

1. Development platforms and options. Google App Engine, for example, currently only supports Python but will soon also support Java bytecode (which in turn opens it up to a range of other languages potentially). For some development needs and teams this is not a limitation at all, for others it removes App Engine as an option. Any cloud computing offering that allows for in essense virtual server instances will typically support a wide range of languages on those servers (as well as development frameworks). However other business concerns, such as how you plan on load balancing and scaling your applications may impact language and framework choices.
2. Business tools included. This is more of a factor for a startup, especially a bootstrapping startup than it is for a larger company. A larger company may have preexisting payment processing systems established or may build an application for reasons other than direct revenue via the application. Not every startup either will need monetization or pass-through billing options. Here Amazon Web Services has a small lead over competitors at least in my initial research as they offer a range of options to handle payment from clients, including billing which includes the Amazon Web Services costs and only charges a small percentage on what you bill your clients over the costs of the client’s usage (currently 3% + $0.30 in most cases).  Salesforce.com for example might offer access into a pre-qualified pool of potential customers, customers already paying on a monthly, per-user basic for software-as-a-service. 
3. Match to your business model. Different providers of cloud solutions have created those solutions based on a wildly different assumptions about the business model of their customers, understanding this and making best guesses (in the case of a startup or of a new project at a larger company) will help narrow down to a manageable pool of vendors. Some providers are optimized for the needs of applications which will store and distribute large amounts of data – here the costs per GB of data (stored and distributed) could be a key business factor in evaluating vendors. As importantly performance could be a key factor, some cloud computing vendors have already built relationships with Content Distribution Networks which can help with the delivery of large files to large numbers of people. But the same cloud vendors might not be a good solution for streaming options (depending on how they work with those content distribution networks and a range of other factors such as network topology). 
4. External factors - a simple example, if you have the type of service which can (and should) be crawled by search engine robots, then it needs to be easily crawled by them at all times – this means that your service needs to be persistent and likely you need a static IP address for the web server(s) hosting anything which might be linked to via external services. A more subtle point, if you will be exposing your appliction as a widget in other sites or as an application inside of social networks you will likely need to ensure 24/7 access to your application and need to have very good response times. Add in a requirement to work with external 3rd party API’s and services (ads, web services etc) and you may need to look at hybrid approaches or base your business models upon an assumption that at least one instance remains up at all times (and then have to factor in how much time it takes for additional instances to instantiate when you are looking at how you will scale if demand spikes). 
5. Your comfort with business partner risk - some cloud computing vendors seem unlikely to either go out of business or to exit the cloud computing business. Google and Microsoft for example are unlikely to go out of business any time soon, Salesforce.com has built a substantial and growing business on the cloud, and Amazon.com seems both profitable and deeply committed to their cloud services. Smaller vendors such as Rackspace or GoGrid or the dozens of smaller still companies present a bit more of a risk. In Rackspace’s case the risk is not so much that they will go out of business (they have prospered for many years now and are growing) but rather how/if they will consolidate a number of aquisitions. GoGrid has a compelling suite of offerings but presents a bit greater risk. For really business critical deployments (including for many startups especially once past the initial bootstrapping stage) I would thus recommend an exercise of exploring how to move from one cloud vendor to another as well as to stay aware of and have plans in place to use non-cloud based options. 
6. International considerations - if your business is entirely inside of the US then any cloud vendor with a US presense is a viable option. However many cloud vendors have restrictions which may impact your decision as you look at global use cases. Payment processing, a key selling point for some vendors, is often restricted to only US customers. Some vendors have great pricing of data usage within the US but charge additional fees for international traffic (directly or indirectly). For example, Amazon Web Services has different clouds for the US and the EU, data transfers within a cloud (between EC2 instances and S3 for example) are free, but if you need to move data between the EU and the US then fees are charged. 

And these are by no means the only factors I am looking at, but are some of the initial ones I am considering as I research options. In follow up posts I hope to explore the current Cloud Computing landscape as well as my initial perceptions of each vendor I look at seriously. I will also, I hope, write up in more detail the technical requirements I have at the moment for the specific project which is inspiring this search. 

Please add other factors you would suggest I consider in the comments below!

Tasks for a new startup – Radioki.com and Startup Weekend SF

Saturday was a busy day. Spent at Startup Weekend SF.

Today will be an even crazier day as in less than 24 hours I will be taking 4 pages of notes sketching out a whole application and putting together a mess of parts and web services into what will be a compelling and useful service for many people. After I post this, my evening (well early morning) will be reading API and data format specifications and working out how to build out our first functional pieces.

However just having a great working application is not all of the tasks that a modern, web 2.0, 2009 edition company needs to do to be successful. Here for my own use (and my teams) as well as I hope for many other entrepreneurs is a checklist of tasks we also will have to try to do this weekend. Please add anything I have missed in the comments below!

[and before you mention it - legal structure & incorporation, partnership agreements etc are indeed important and if as we hope it does Radioki takes off we will complete them, we are building this in the context of pre-existing friendships as well as the Startupweekend open & collaborative ethos]

• Register your new brand domain. We did this Saturday afternoon. Nothing at Radioki.com yet, but that will change rapidly.
• Sign up for Twitter for your new brand. I’ve set up @radioki follow us to get updates on our progress, access first and we hope a few other surprises.
• Set up an internal tool for documentation and collaboration. We chose the very simple and easy to sign up for and use PB Wiki as a repository for our team notes, drafts, pseudo code, internally important data etc.
• Establish a simple version control system. Even if you have just one developer, work with a version control system everywhere you can (which is pretty much most things). A wiki for internal team documentation gives you version controls & who made what change data tracking inherently (assuming you as I would suggest use a private tool for that collaboration)
• Register for all of the relevant API keys your applications will require. These days this can be a very long list. In our case we have at least three major API’s which we will use, multiple web services, Javascript frameworks, web hosts, domain registrar and much more which we need to sign up for and use.
• Establish early on (as in before we launch) customer support & feedback channels. Almost certainly in our case this means that we will create and set up a GetSatisfaction for Radioki (using the free version first until we have a business model to support more) – note, when we complete the next task, we have to go back to sites such as Twitter and GetSatisfaction and upload our logo there as well.
• Design a logo and pick a basic design pattern. Be comfortable with this being basic and expect it to change, but to launch quickly create a simple (even text only) logo to use at your avatar image across the web, to use on your home page, and along with it a basic color palette and design style for your overall web presence. Expect to change this but spending a few minutes early on in the process helps you create a clean, consistent look across web services and sites.
• Set up corporate email addresses. Even if all you do is have them auto-forward to your regular email, yourname@newcompany is useful and is used as proof of employee status by some sites such as GetSatisfaction.
• Join the appropriate networks as the new corporation. In the case of Radioki this means Facebook but because we have a strong Music component also means active engagement with Myspace.com (and especially MySpace Music).
• Update the personal sites and network profiles of all founders. When you launch your personal site and blogs should note this and the profiles of all of the founders (and early employees if you have any) should be updated to reflect involvement with the new company. This is a signal for people who follow you on each network or who read your blogs that you are working on something new.
• Link back to and thank publically as well as privately all the services your new company uses and works with. Besides being just common politeness everyone who builds any service wants to see it used and welcome thanks and updates about how their solutions are being deployed. Also many API providers offer directories of applications using each API. Building relationships with each company your solution relies upon and works with can also lead to lots of helpful advice, guidance, updates about new features and opportunities for promotion.
• Remember to add contact information and background to your new company site. Yes, focus on getting the service built and launched, but also remember to include who you are who are building the company as well as how to reach you and who to reach out to for any media who might want to contact you. Photos of the core founding team are great as are short bios. All serve to humanize what can often be a dehumanizing process (web applications for example). And yes, real names and a corporate mailing address do combine to give lawyers someplace to send stuff – but it also gives journalists, bloggers, investors and future business partners someone to talk with as well.
• Build logging and analytics into your site and application from the beginning. Deploy Google Analytics or another similar product on your new domain from before you share the URL with anyone (hmm we’ve broken this one so have to fix this quickly) For your main application make sure that user actions are logged so you build up a history of interactions. In our case this means ensuring that every search query entered is captured. Ideally you also log what output (or if something failed what error messages) resulted from that interaction.
• Reach out to your friends. A new project whether big or small is perhaps the best excuse to catch up with your friends old and new. In fact I love it nearly every time a friend sends me an update about new projects or companies. Often these updates are the first time I’ve heard from someone.
• But don’t forget to also reach out to the media. Start with the media who are also your friends. If you friends also covers your space then reach out to them on a personal level. Don’t send your friends mass, blast emails if you can avoid it – if not, then follow up (or send in advance as well) a personalized note. Do not rely on your friends having your contact details handy – include a direct phone (cell phones are great) as well as your personal email address.

And those are just the relatively simple, basic stuff. When a new company is launched a whole additional set of tasks get added nearly immediately. A few things to think about relatively soon.

• Corporate banking relationship. This will require legal incorporation in some form (or will require initially to work off a founder’s personal accounts – opening up reams of tax/legal complications. However such a relationship is a key part of being a real business – it gives you a way to sell to people via giving you a means of depositing checks.
• Corporate legal relationship. Establishing a legal relationship, even if a relatively simple and low cost relationship is another part of being prepared to be a real business. A lawyer may early on be called upon to help with incorporation, reviewing various agreements and you hope reviewing customer contracts or investment documents (or best case both).
• Building out the non-functional parts of your new site. What I mean here is collecting excerpts of blog posts and news articles & embedding audio or video coverage. This also includes keeping a new corporate blog up-to-date and continued use of the corporate Twitter account etc.
• An ongoing PR relationship. Of course with a firm who knows your business area, with whom you can work closely and who gets your product as well as process. Great PR firms add incrediable value.
• Telling a clear, updated and ongoing story. If you (or co-founders or early employees) are not great storytellers or public speakers then likely your PR firm (and perhaps other advisers) will need to help with this but especially early on it is vital to have a clear story about the company and your new, emergent brand. This story should be short and clear (oh and compelling)
• Have a business model (or two or three or four). You do not have to implement the business model immediately, nor do you need to share it with anyone (though your co-founders should also know). But having a business model in mind can be exceptionally helpful as you evaluate what to use/not use, what to build/not build, what to track/not track

And yes, this list is long and incomplete.

I skipped over raising money, I skipped over legal incorporation (rarely a good reason not to just incorporate as a Delaware C corporation). i skipped entirely over office space. Until an income is generated a large number of boring but important tasks are delayed (salaries and benefits for example).

For now, sleep then back to work.

Radio Schedules 2.0 at Startup Weekend San Francisco 2009

Back in Dec I posted about Radio Stations 2.0, an idea I had for a return of great radio schedules, updated and enhanced for the 21st century. My post attracted some great feedback and some comments as well as backchannel reactions. I placed my ideas out in public under a bit of a CC license and encouraged anyone to implement them (though I requested at least some attribution).

Friday night after the fantastic Web 2.0 Expo I arrived late to Startup Weekend San Francisco which this time is organized by many fantistic people (and friends of mine). As people went around the room offering up their pitches to the crowd (and to the panel of VC/angel investors who were offering feedback on the form of the pitches) I decided that I would offer a pitch myself.

So I remembered my Radio Stations 2.0 idea, since it is an idea I have already shared publicly, I don’t mind sharing it again, and there is the chance that by doing so at Startup Weekend (and of course following up with a great deal of work most likely) I may be able to inspire enough help from others to make it a reality!

I’ve updated my original post with some more analysis of the competitive landscape (in the comments). In the rest of this post I will set out our goals, targets and next steps for this weekend. Hopefully we will be able to cobble together something working by Sunday evening (and continue to refine it further after that).

Basic Idea

Finding radio content whether in a rental car in a new city, on a mobile device or at your desktop is frustrating. Radio Schedules 2.0 is a simple, lightweight, API driven directory of terrestrial, satellite and Internet radio shows. The API will allow for both write & read functionality and likely will be combined with a wiki(like) set of data (station ranges & descriptions, show descriptions etc)

Competitive Landscape:

Since RadioTime does exist (and is a commerical entity already) we are going to look carefully at what we can (and should) do to be different, lightweight, and add real value as a competitor (in some ways) or perhpas even as a complementary service in other ways.

Other competition includes PublicRadioFan.com which lists most public radio stations from around the world (with Internet presenses) and a project started in 2003 (and put on hold in 2003) do something similar.

Steps for the weekend

1. Define a simple data structure(s) to store the data we gather. Of particular note this will likely include a geographic focused set of data – station data driven by actual tower locations & signal reach. Potentially this could include variations by time of day & date especially the case for AM radio in the Midwestern US. It will also include a temporal set of data – shows on a given station aired (or scheduled to be aired) at specific times.
2. Design our data to build up over time – i.e. not just “what is on now” or “what is scheduled to air next” but also “what just aired” or “What was on this morning during my commute…”
3. From the beginning expect to build & deploy on servers located in the Cloud. This means evaluating Rackspace, GoGrid, Amazon’s Web Services as well as others.
4. Design for a data-driven business model. Perhaps surprisingly a great deal of this design will be involved in streamlining and simplifying what data we need to collect & store from people. But by design this will include storing a great deal of log data & anticipating using such data extensively.
5. Stay and work openly. I will likely update my blog with one or more posts of our progress as it happens this weekend – probably including some calls for help in specific areas.

Current design thoughts (very early, very rough)

• Stations – are associated with One or more “dial” positions For terrestrial radio this is the dial number (or numbers in cases of stations with multiple towers). Have a related schedule (or schedules in a few rare cases). Associated with a bunch of data about the station (probably in a wikilike manner that allows for versions)
• Schedules - related to a station (rarely but occasionally multiple different stations). Composed of many “shows” and a true temporal dataset (with start & end times, times normalized to a single timezone) may occasionally also have further details in a wiki (but less often, though “source of data” will be tracked – could be API calls, could be web crawl)
• Shows - A unit of a schedule, but shows can have a meaning by themselves (syndication). May have further data in the wiki.

When a request comes into the system that request MAY have the following:

• a geographic location (which in turn implies an likely interest in Terrestrial radio schedules)
• a range of time (blank may imply “right now”)

At some future point the system may do more with who makes the request (individual web user, individual web user w/tracking cookies, API called etc.). The system may also do some matching/recommendations (using Last.fm profile info or the like as a starting point) but that’s probably not in the first release.

Technology thoughts

• Start with standards – ideally calendar data will be available in an iCalendar form, via standard means of access. Where microformats make sense we should use them to semantically market up pages we generate (ideally this happens in the background so if a given page is editable ala a wiki the microformats are applied on top of that where they apply)
• Design for API use - ideally this means even for our own interfaces we use the SAME API’s we make available for third-party use. This then forces us to make the API’s simple and as stable as possible (we may of course use white-lists in the future to rate throttle some API access). It should also facilitate the use of other web standards – for example since we are starting from the beginning there is no reason we shouldn’t start using OpenID/OAuth instead of implementing our own Identity systems.
• Focus on simplicity – there are many directions we could go and we will want to explore how best to compete (or not) with RadioTime. Almost certainly our best approach is to keep it simple, do something exceptionally well and iterate.

a business idea – radio schedules 2.0

I’m old enough, just barely, to recall a time when local radio schedules were printed in the local newspaper. As a kid I used this to track down “old time” radio shows and Dr. Demento. Today almost no schedules here in the US are available in any form, individual stations may publish them somewhere on their website, and a few specific shows publish a schedule of when their show may be syndicated, but there is nothing (at least that I have found – if there is please leave a comment) as good as the extremely well done The Radio Times in the UK.

So a thought for a modern 21st century twist on a very old idea – simple, location & timezone aware radio schedules – probably driven via a community powered wiki like tool (with options for “official” schedules from any station interested). Schedules which would be published in many formats – with full, open API’s to access them (as well as iCal subscription links and probably RSS feeds including search driven feeds).

I’m thinking a website and likely iPhone app (probably for other devices as well). And it should be platform neutral so have options to also display Internet radio stations, streams, satellite radio and also podcast links for shows which have them (many commercial as well as non-commercial shows do).

And ideally there could be many interfaces to this data – time & day & location being just one.

Not neglecting very basic data would be key here – call letters but also the actual dial location (or locations) & URL’s etc. Best case also some estimate of reception for a given geo location – though this is wildly hard.

And don’t neglect AM and non-English stations (heck don’t limit this to US stations).

I suspect I am far from the only person who has moved to a new city and now has no dial sense – ie I don’t know where to find radio stations which I might be interested in or specific shows on those stations.

Anyway a thought for a service which I’d love to see – and a reminder that factual data isn’t copyrightable (so while show descriptions might be the fact that a show starts at a given time on a specific station is not) plus I suspect anything which helps rebuild audiances/build them will be welcome.

Consider this idea cc-atribution licensed. Feel free to turn it into a commercial project – though if you do I’d love to be involved and even if not, would appreciate some attribution. 

Done well I think such a schedule could seriously help terrestrial, online, and satelitte radio. It could also include other “scheduled” audio (and perhaps video) content – so might also include the expected release schedules for podcasts, video series, online shows and more. 

A bit of my background, for many years I worked on and build calendaring systems and served on the IETF iCalendar working group, including a brief stint as an editor of the RFC for iCalendar. I’ve been thinking about calendaring issues for many, many years. I’ve also been a lifelong radio and audio entertainment fan. I even did audio sound effects for a college production of the entire Hitchhiker’s Guide to the Galaxy.

Evaluating a new laptop vs refreshing old – MacBook Air vs ThinkPad X60

If you have been reading my blog for a while you may know that I have a ThinkPad X60 as my current laptop and that I have been seriously unhappy with the laptop and Vista (as well as Office 2007 and related software). At the recent SXSW conference where I mostly went without using my laptop at all (as a bit of an experiment in being highly mobile and not carrying a bag at all) when I did try to use my laptop I was seriously frustrated – in one instance it almost literally took 15+ minutes of work before I was able to actually start doing anything – and I had to shut down 5 minutes later.

While at SXSW I was also emailed an opportunity to purchase a friend of a friend’s MacBook Air – he’s decided to buy the MacBook Pro instead. Buying it from him would save me sales tax and would include the external superdrive. But it is the lower end, 80GB edition. And there are more than a few things I would have to add to the system package (AppleCare more crucially).

So in this post I am going to look at the pros and cons of my current options – and most likely won’t reach a clear conclusion. Please add a comment if you have solutions to any of my issues/concerns or if you have suggestions for alternatives I should be considering.

First note, my laptop is an extension of me – I’ve had a laptop as my primary computer since about 1994. Historically I kept most of my machines until they almost literally fell apart – driving them hard though I also have tended to buy very close to the peak at the time I could buy (not as ‘full desktop replacement” but as best weight-to-performance-to-battery-life. So each time I’ve replaced my laptop I have spent up to about $3000 – that said, I don’t really have the spare money to buy a new computer at the moment – but then neither can I afford to be unproductive or to continue to have serious issues on a daily basis.

My use of a laptop

• heavy and frequent web browsing and research. I am “online” for many hours every day, much of which is spent with many tabs open in my browser (typically Firefox) in which I am researching, writing, and monitoring
• syncing my iPhone. Most critically with my full contacts database which is, in turn, also synced up to Plaxo. Slightly less critically (since I rarely use Outlook these days) syncing my iPhone with my calendar (this is an area I hope to improve). And I do sync about 6gbs+ of music and the occasional tv episode or short film to my iPhone for later viewing. Most crucially this must include my most recent podcast subscriptions
• syncing my iPod, especially when traveling. I have 100gb+ of my music (and a few tv shows I’ve bought) on an external HD, I have about 30gb of podcasts on my local disk, I synch about 30gb of my library to my 30gb iPod Video (3gb of new content such as recent podcasts, 16+gb of content I haven’t played recently, and a careful collection of my favorite content I want to have with me)
• preparing and giving presentations. I speak at conferences, I pitch to investors, advertisers and partners. While I don’t love PowerPoint, I do have to present on a regular and increasingly frequent basis. I do not, however, do much in my presentations which couldn’t easily be done with Keynote (perhaps even could be done better)
• manage my digital photos. I don’t take enough digital photos (or videos) but I am trying to increase the frequency with which I take photos – and I have a growing collection of photos I’ve taken. I don’t yet have a Flickr Pro account (probably should do that soon) but even with one, I would still want to retain the full resolution, local copies of every photo I’ve ever taken (perhaps stored on an external drive but everything – or at least the stuff that is good enough I might use it – should be at my fingertips at any time
• manage my contacts. I have something close to 6000 contacts in multiple Outlook contacts files. While this is far too many and many are generated contacts from the testing of various systems (which analyzed my email traffic looking for people I should have as a contact) I really do know a ton of people. My contacts data about them is one of my most precious resources, in many cases complete with photo, bio, notes on when/how we met etc – and in many cases updated via sync with Plaxo (and in some cases LinkedIn as well)
• manage my email archives and search them. I currently have email going back at least to 2005 and I think with archives back to 2000 on my current laptop (in a collection of Outlook files). Like my contacts data, my email archives are key data for me – data about when I met someone, what our past interactions have been on etc. Overtime I am slowly weeding and culling my archives of the cruft (old mailing lists, commercial solicitations, spam, updates from various websites etc) but even with that process done (which it is far, far from being so) my email past holds much of my memory.
• keep up with my current email. I mostly use gmail these days, and almost entirely viw the web or my iPhone. I have multiple gmail addresses I watch (my personal address and various emails aliased or forwarded to it, and my professional email address given to only a very few people at the moment but those numbers will rapidly increase) For this as present I use Thunderbird as Outlook is far, far too flaky for me to rely on it
• Read PDFs. Mostly as part of my ongoing research and product development, I end up with a lot of PDF files to download and read. With more arriving every day. My preference these days is to “print to PDF” rather than to paper for about the past 2+ years I have almost gone without printing anything – just occasionally a travel document or contract needing a physical signature. On my ThinkPad I have a useful but not great “print to PDF” application, Macs have this feature built into the OS.
• MindMapping and notetaking. Historically I have used MindManager a great deal (but almost not at all for the past year+). More and more I have just taken notes down in simple text files when offline or when online in various applications (including as draft posts for this blog). This is far from ideal, especially as my needs will be growing exponentially in coming weeks and months. Whether I stay on Vista or migrate to a Mac laptop, I will need to get a great note taking, brainstorming, and task management/project management tool or tools.
• Offline HTML writing. I occasionally blog for other sites than this blog, when I do that I tend to write my posts in an offline HTML editor and then send the editor an HTML file instead of retyping the post or trying to compose the post online (since many conferences where I might be writing from have poor to non-existent and flaky internet access even for the press). Currently I use Microsoft Expression for this, though mostly out of inertia and from having a full copy (actually multiple copies) given to me by Microsoft at various conferences I have attended over the past few years.
• Very rarely but likely to increase spreadsheet analysis. I can crunch numbers with the best of them, but I’ve never been a spreadsheet junky. My tools of choice start with text and flow out from there – but as I grow my company I will have to make more and more use of spreadsheets over time. And likely web based alternatives won’t fully do everything (currently at least) which I need to do, though for basic collaborative tasks they are great). At least once a quarter, if not more often, I will, however have to present numbers to my board (currently small but as we close our first round of funding likely to grow). On my ThinkPad I have Microsoft Office, on a Mac I’d likely start with iWork Numbers (which I already have on my iMac) and will only buy Excel if I truly need it.
• and that is about it really. I don’t have games installed on this ThinkPad (just the basics which come with Vista but haven’t used them in years). I have other software installed but almost never run it (Visual Studio for example). Running at boot I have Skype and Google Chat – but actually rarely use either (and for that matter they are both available for the Mac as well). I have Microsoft OneNote (my laptop is a tablet) but I actually almost never use the tablet functionality – silly I know and a bit of a shame, but also very much the truth. I kinda wish I did use it more often, but in actuality I don’t (and apparently I’m far from alone). I also almost never use video playback on my ThinkPad – I think mostly because the experience even with a local file is quite poor. Instead I watch any videos (including video podcasts) on my iPhone or on my iMac desktop – which is also the machine I’ll use mostly when I buy any video content or when I test/use a service like Joost or Hulu.com or another video service.

So with all that said, how can I decide between my various options.

Scenario One – keep ThinkPad but try refresh/reinstallations

At SXSW I spoke with friends who work for Microsoft. One suggestion was that the OEM installation of Vista, especially on ThinkPads unfortunately, is not very clean or well functioning. His suggestion was to get a full install disk of Vista and do a complete wipe and reinstall everything from scratch.

This would require I backed up all my data. That I made a very complete list of all of the software I have installed (antivirus software, firefox, thunderbird, MSFT Office 2007, MindManager, etc) and made sure I had all the relevant license keys for each product as well as the current installer (or at least how to get the latest versions – or in some cases the versions for which I have a license). Then I would have to reformat my disk completely (likely wiping the IBM special partition as well) and reinstall Vista. Then install MSFT Office 2007, FireFox, Microsoft Expression, Thunderbird, anti-virus software, Skype, Google Pack, some of the key pieces of IBM software (password manager using my fingerprint scanner perhaps, power management software etc) and then migrate back my key data (iTunes, Outlook files, recourses/research, writings, photos etc.

All in all that would likely require 1 to 2 full days between the full backups, reformats and very significant post-installation patching efforts.

But as a result I also quite likely have a much cleaner installation, less cruft, likely a much better performing laptop, and might take the opportunity to structure the laptop to also dual boot with a linux installation (Ubuntu?). If I can use the full license to Vista Microsoft gave me a while back the cost for this would be minimal – but the time and effort could be considerable. And almost certainly there would be one or more issues around licenses with something I want to install.

Scenario Two – I buy the MacBook Air (used) from a friend of a friend 

This would cost me about $1800 for a MacBook Air + external superdrive. On top of that I would probably buy additional AppleCare (another $250 or so) so as to have support into the future.

It would have to be shipped from the east coast to here on the west coast – or I might pick it up in person on my next trip to the east coast in a few weeks.

To make the MacBook Air functional for me I would have to install an office suite (iWork? – which I do have a copy of for my iMac have to check on the licensing for whether I can also use that on a laptop). I would likely buy a small bit of software to help migrate my data from Outlook to formats importable into the Mac built-in applications (though I’m not sure if I want to use those apps or not – haven’t ever used them so don’t fully know if I would like them or not).

I would then have to migrate my iTunes library (always painful) and connect an external drive with my music library to the Air, probably connect via a USB Hub so I can also connect my iPhone and/or my iPod. For the iPhone I owuld have to do this AFTER contacts have been synced and I would have to set up the new connections for data for the iPhone (not sure if I also have to reformat it to work smoothly with  the Mac).

If my iTunes data import works smoothly I should have everything set up, but it not I’ll have to spend a lot of time getting iTunes set up for my use (rebuilding smart playlists etc) and I may lose a lot of key data such as timestamps of when I added data to iTunes, playcounts of files, ratings of songs, podcast subscriptions.

Likely I’ll also need to replace my current, 120gb external portable drive with a much larger but still very small external drive. Ideally at least 300+gb but very lightweight. I’d expect the cost for that will be at least $100, likely closer to $150 but I’d be happy to find that’s high. In setting up my podcast subscriptions as well as my subscriptions to tv shows via iTunes I’ll have to decide where those files come from and are stored (ideally I can do this is in a way usable via my iMac as well – but that might be tricky and some files likely should be local to the Air so I can use them when not online)

Very likely I’ll also have to spend $99 a year to get a .mac account so I can use the “back to my mac” feature to reach my desktop iMac and perhaps use the .mac account to do some data synching (though Plaxo may be sufficient for much of what I actually need done.

I’ll also then need to install a variety of useful Mac software – Skitch for example is a big draw for moving to the Mac laptop, a tool I’d expect to use fairly frequently. I knwo there are dozens of other applications which friends would suggest I use and which I would test out and decide amongst over time – apps for productivity, apps for business/brainstorming/notetaking etc. All told I would like spend a fair chunk of change on new software for the Mac laptop – whether I get an Air or another model. But, for the most part, these would also be tools which pretty clearly would be helping me get more done and be more effienct.

In the case of the Air however I almost certainly won’t install VM Fusion or Parallels as there likely simply isn’t the diskspace to use either effectively. In my current home network configuration this means that I have to give up entirely on using my current printer (for which there are not OSX or Linux drivers). So though I don’t print a lot, likely I’ll have to also plan on investing in a new printer.

Scenario Three – another model of a Mac portable 

I do like the Air’s multi-touch trackpad, I can see myself using gestures frequently. So that rules out (for now) the lower end MacBooks or a used/refurbished MacBook Pro. But I would have to give the other MacBook Pro models serious consideration. The 15″ laptop has nearly the same resolution as my current ThinkPad (one of my major concerns with the MacBook Air is that the resolution there is lower than on my ThinkPad – and my ThinkPad’s resolution isn’t high enough for me – I really like be able to have a lot of information on the screen at once. That said the clarity of the Air’s screen is fantastic and the performance of the graphics is better than my ThinkPad so video etc likely will look much better (be playable in fact).

A 15″ MacBook also weighs around the same as my ThinkPad does with the extended life batteries which I have. However the battery life is a bit lower (3 hours or is what I’ve heard but I’ll be checking with people on that). But overall it would be a great machine and would cost not a lot more than the MacBook Air (less perhaps if I can get a discount from a friend who works at Apple which is a serious possibility).

Scenario Four – another model of PC laptop – running Vista 

Least likely, as there are aren’t many other models I might want to buy but this is a consideration.