So what’s next? Well, I think what’s next (and by far most interesting) is some concept of the “strength” of a connection. Specifically, today I can see a lot of my friends’ social networks, but I have no idea for the relative strength of connections. Sure, if I see Person A knows Person B, I can always make an offline inquiry to see if that connection is strong or weak. But very soon I think we are going to have tools like Xobni that profile communications patterns and surface that information both to end users and to other applications. And it won’t be just social networking and community applications that benefit. Enterprise applications (collaboration tools, CRM tools, HR/recruiting systems, etc) will all benefit from having access to some of this information. We’ll call this contextual “strength” Phase III.

Phase III is really interesting to me because I think it has to be a largely machine-driven approach. Communication patterns are too dynamic for any user to bother continually updating “strength” of connections. Also, as Xobni has shown me, if you are a power emailer you’re likely to be surprised by who shows up as ranking highly. There’s no reason the same can’t be done for IM. I’m not sure that I’m going to turn my phone logs over to some 3rd party analytics company, but IM and email would be a pretty decent picture of what I do and with whom I communicate. Passive profiling of communications patterns is going to be really interesting and I think will expose really interesting information about the nature of communications. I think Xobni is on to something really cool and big as it’s delivering value to me today (even though I have to use it in Outlook) and I can see a path to a lot more value in the future.
As an aside, I think this is the best shot that Google, Microsoft, and Yahoo have to wedge their way back into social networking relevance. They already own the message stream and have the data they need to get a sense for who knows whom. It will be interesting to see whether they choose to open this information up and let other applications take advantage of it or whether they use it for the bedrock of their own auto-generated social networks.

• The interface is quick – The Gmail interface is really snappy. It loads quickly and refreshes automatically. As is the case with most Google products, speed is clearly a high priority and it works really well.
• I can process/triage messages very quickly – Once you master the key keyboard shortcuts (j,k,x,n, and p are the crucial keyboard shortcuts to master in my opinion), it’s really easy to blast through a bunch of messages in your inbox and quickly triage them or otherwise mark them for future reading/evaluation.
• Search trumps foldering once you make the big leap – I am an active labeler in Gmail, but I’ve gotten lazy/sloppy with some of my labels over timer. The key “ah ha” moment in most Gmail user’s evolution is the moment in which the light bulb goes off and you realize that search is a more powerful navigation paradigm for email than foldering. It’s a leap of faith until you make the change.

One thing worth noting about the three things that I like most about Gmail – they only really matter if you are in a position where you need to manage (read, write, retrieve, and share) large amounts of email. If you don’t get a lot of email, most of these features and benefits don’t buy you much. In fact, you probably would not even bother mastering these things if you are not a power emailer.

The subject of to whom Gmail-like interfaces appeal is a subject for its own post. For the purposes of this post, we’ll just say that things like Gmail are designed for expert power users and have a high bar to adoption. However, once you adopt, it’s hard to switch.
After trying to go back to Outlook as my every day mail client, I’m finding it to be a very difficult adjustment. There are 3 things that stand out after a few days of non-Gmail email existence:

1. I miss keyboard shortcuts – a lot. After being out of the Outlook experience for over two years, I find the keyboard shortcuts to be a bit slow. Also, with the myriad number of formatting and presentation options that Outlook offers, it’s hard for me to actually remember all of the keyboard shortcuts at my disposal. The relatively short list of Gmail shortcuts that I can use really do the trick and allow me to get my work done quickly.

2. The Outlook client feels really slow. The time spent selecting messages, opening them, waiting for them to open, and then closing them and moving on to the next message just feels a lot slower in Outlook. I don’t know whether it’s because I’m less familiar with the interface or if there is something else at work. It just feels like it requires more keystrokes and work to get through my email using Outlook.

3. Working offline is not as big of a bang as I had thought originally. Now that I have a broadband access card for my laptop, there is relatively little time when I cannot be online if need be. Suddenly the ability to use my mail client offline is of less value as I find myself offline with declining frequency.

At the end of the day, I think that has big implications for folks who are building apps that plug into Outlook. Sure, not everyone in the world who uses email will switch from Outlook to Gmail. However, I know a lot of power email users who are moving away from Outlook and adopting Gmail. Given that so many of these interesting email products target power users, I am curious to hear how they will deliver their solutions to the (relatively) closed environments that we find in webmail. Greasemonkey scripts? Biz dev deals to get access to the platform? Lobbying hard for more opennes and APIs? I’m sure they’re all thinking about this stuff and what it means for their businesses.

As always, comments are welcome.

The traditional packaged enterprise software industry doesn’t feel like a high growth area. It’s large, but not so dynamic. Enterprise software is definitely a really large industry. However, with Oracle, SAP, and Microsoft buying up almost every category-leading vendor out there, the industry feels like it’s a large behemoth with limited growth opportunities. Aside from SaaS and open source, there aren’t a lot of areas of software that look attractive to new folks in technology. On the flipside, consumer-facing web companies are not nearly as large (in terms of profit potential), but appear to offer much better growth prospects.

The nature of the sales and product development process tends to keep younger people in the background. Most traditional enterprise software companies, save those who are targeting mid-market or SMB customers, tend to sell to senior executives at Global 2000 companies. The folks to whom these software companies sell tend to be senior executives and well, older in general. I’ve certainly seen software companies who want to send sales, marketing, and product folks whose age and experience profiles more closely match those of their target customers. As such, it means that many younger people end up having to “pay their dues” in the background before they get additional levels of customer-facing exposure. Contrast this with the latest wave of web 2.0 companies, many of which feature people in their early 20s in leadership positions. Without the need to sell directly to customers who are senior executives, it’s not as necessary to have “grey hairs” in visible roles on the team.

Enterprise software companies have really long product cycles, whether it’s initial development or future revisions. I don’t know a lot of enterprise software companies who release more than one major upgrade of their core product with a frequency greater than every 12-18 months. For someone who’s eager to get feedback about what they’re working on and get experience with the product launch process, that’s a long time to wait. You’ll basically need 3-4 years to see a few revs. You’ll learn a lot in that time, but it’s a long time to wait. There are lots of web companies who launch new revisions to their core platform in a near constant basis. This offers a young person many more opportunities to see the launch process in action in a fairly short period of time.

It’s hard to start an enterprise software company until you understand enterprise customers. Simply put, I’m not sure how you develop a CRM software solution, the next generation security application, or the next financial application unless you’ve gotten to understand the basic needs of these customers. As such, I’m not sure how many college students or young folks in the industry have this kind of insight until they’ve been in the industry. And if you don’t enter, then how will you learn these things? Again, many of the folks in the web 2.0 space are building apps to solve problems they understand where they are part of the core customer segment.

Enterprise software companies are a great place to learn how sales, product development, and marketing all work together. Despite all of the many issues identified above, enterprise software offers a much better place to learn the business of software (or just business in general, for that matter) than most web 2.0 customers. In enterprise software, you learn a lot – you can learn a lot about how the direct and channel sales processes works (which is largely absent in most web 2.0 companies), how to manage a longer-run product development process that involves direct interaction with existing and prospective customers, and how more traditional marketing (product and corporate) can help drive effectiveness in software. The interplay of development, sales, and marketing in an enterprise software company can teach a young person quite a bit about how business works and how these three forces need to balance each other. Oh, and let’s not gloss over the fact that enterprise software tends to generate cash and lots of it – nothing like having your performance and

For all of the downsides of working in enterprise software, I think the current generation of web 2.0 entrepreneurs could benefit from some of the hard-learned lessons from a career in enterprise software.

Presumably the companies being targeted with this fund do not have to build exclusively for the Salesforce platform – There is isn’t anything I’ve read that makes me think there is any requirement to build exclusively for the Salesforce.com platform. I can’t imagine that would be in the best interest of the companies in question. If the requirement is that you build on the Force.com platform while retaining the ability to build a standalone business, this is not a terribly onerous condition to fulfill. I’d imagine that Salesforce will be one of several channels these companies use to grow themselves into larger businesses.

While Salesforce is a great business, I’m not sure that you can build a venture-scale business solely on the back of Salesforce – While Salesforce has built a great business around CRM and ancillary areas, I’m not sure that there is enough breadth (as opposed to depth) of activity on Salesforce.com to build a software company with a $50 million revenue run rate (yes, I know that’s an arbitrary number, but it’s big enough to be viable and interesting) purely on the back of existing and future Salesforce customers. I am, however, quite sure you could build a smaller business that would be interesting to an individual entrepreneur, though.

Salesforce clearly benefits from getting the opportunity to screen and get early access to promising SaaS firms – It seems to me that Salesforce could be a big winner here. They aren’t putting up any investment capital (as far as I can tell), are getting access to early-stage SaaS companies open to building on their platform, and the success of those companies will ultimately make the Force.com platform more useful.

At the end of the day, this sounds like a developer relations and marketing play operating (cleverly, perhaps) under the guise of an investment vehicle. Given the stakes involved and the opportunities in SaaS, I’m curious to see whether all 3 parties get what they expect out of this arrangement – it’s certainly worth watching.

Is it just me or does there seem to be a subtle (or not-so-subtle) recasting of web office suites to be less about new functionality and feature differentiation and more focus on the price differential versus Microsoft Office? Early in the web office discussion, it seemed to me that there was a lot more conversation about the benefits of using web-apps (no VPNs, universal accessibility, easier to manage and deploy, etc) versus traditional desktop applications. Repositioning the conversation around price comparisons is a shift, it seems – there are certainly folks for whom price is the major impediment but this recasting strikes me as an admission of how far the industry has to go to reach real competitive parity.

Also, it’s important to note that some of these “disenfranchised” folks who do not have desktop productivity applications on their computer don’t need them. If you are in a task-oriented job where you enter data into a system, you might as well have a terminal as opposed to a full-fledged PC. Why would you need access to spreadsheets, word processing, and email?

More than revenue and sales, this partnership could give Google much more insight into what corporate IT folks need to see out of Google Apps for Enterprise before they start writing checks. It’s worth noting that Google has one major touchpoint with enterprise IT folks today and that’s the Google Search Appliance. The folks who are managing online advertising spend are likely not the same folks who make IT infrastructure decisions. Working with a large system integrator is a good way for Google to get a handle on the key requirements they’ll need to address to make GAFE a more palatable product for larger organizations. I also wonder if spending more time with the guys over at Salesforce.com might not also be the answer – those guys seemed to have cracked this nut before and I bet they’d be willing to share parts of the playbook.

From my experience, many employees struggle to use the tools that they have at their disposal today – adding more tools in might just make life more complicated. I’m sorry, but the whole “Team Productivity” moniker just sounds weird to me. I’ve worked at a handful of places and in almost every case I’ve seen employees befuddled by the full range of things you can do with the existing tools at their disposal. Adding in a new layer of tools and interfaces to learn when the existing products aren’t being fully utilized today might make life harder (as opposed to easier) than it is today. The history of groupware and group-oriented productivity applications has shown that it’s a tough nut to crack. Often times, the individual must find a way to be productive before he/she can worry about improving the productivity of the whole.

All in all, it’s an interesting announcement. I expect it will generate modest amounts of sales for both parties but will help Google get smarter about how to sell, develop, and position their product for a more sophisticated audience.