I noticed something when I tried out two apps (Mingly and Cobook) this morning – they each immediately asked to connect me to Facebook, LinkedIn, and Twitter during their onboarding process. And, by using my Gmail as the starting point / authentication, they connected me to G+.

Microsoft is conspicuously absent from this. I’ve noticed this many times in the past but when you onboard yourself in two contact-related apps in the same morning and there is no Microsoft anywhere, there’s something going on that’s important. I wonder if this will change with Office 365 – I hope Microsoft is building a trivial to use oauth to O365 so it’s easy to connect to, along with a good sync API.

I was trying to think of other authentication that would be helpful to me in the context of my contacts. Almost everything else I use is based on either my email address or auth with one of these four services. Hmmm.

So far Mingly feels basically the same as Gist but Cobook seems different than anything I’ve used. I have no idea if I’ll keep using either of these, but like many things in the themes we invest in, I love to play around with new apps for a while and see if it sticks.

Over the past month I’ve been systematically cleaning up my social graph. It took me a while to figure out how I wanted to do this, as I’m a very active user of Twitter, Facebook, LinkedIn, Foursquare, and Google+ along with a bunch of applications that leverage these various social graphs. Historically, I’ve been a very promiscuous friender, accepting almost all friend requests.

While this strategy worked fine for me for Twitter (since I didn’t have to do anything, and could deliberately choose who I wanted to follow) this didn’t work for any of the other services. Specifically, Facebook had become basically useless to me, LinkedIn’s activity feed was pointless, Foursquare scared me a little, and Google+ was just a cluttered mess.

As I used each of these services daily, I thought hard about how I was using them and what I was doing. I realized that I was using Twitter ideally and no changes were needed. I broadcast regularly through Twitter, which connects to Facebook and broadcasts there as well. I consume content in a stream throughout the day from about 600 people who I follow. I unfollow someone periodically and add someone new periodically. The tempo works fine and I have my Twitter activity feed up on my Mac all day long.

Facebook was more perplexing to me. Ultimately I decided to orient around my activity feed and started unfriending anyone who I didn’t want to see in my activity feed. Given the current Facebook infrastructure, these folks will still “subscribe” to me (same as Twitter follow) and anyone who wants to subscribe to me can. Unfortunately, the UX for unfriending someone Facebook is horrible, so it’s a tedious and long process. I’ve decided to unfriend 10 people a day which means I’ll be done in about 200 days. I realize that once I’ve got this done I need to adjust my security settings to reflect what I actually want to share. That’ll happen at some point.

LinkedIn was easy – I just decided to ignore the activity stream. I’m remaining promiscuous at LinkedIn with two exceptions – no recruiters and no totally random people. LinkedIn continues to be the best way for me to discover professional connections to people I want to reach and the wider the network, the better.

Foursquare was the hardest to figure out. I rebroadcast Foursquare to Facebook and had a very uncomfortable experience this summer with someone pretending to stalk me on Foursquare. While it was a prank, I never found out who did it which caused me to quit Foursquare for a few months. I get too much value out of Foursquare as a historical record (I love 4sqand7yearsago) so I’ve just decided to aggressively unfriend anyone who I’m not close to. Once I get this done, Facebook done, and my security settings right, I’ll be in a happy place.

Google+ is more dynamic right now as I figure out how I really want to use it. I’m finding the integration into Gmail to be very interesting and I expect my use case will change as they roll out more features, like they did today. For now, I’m using it much more like Twitter.

As I’ve been cleaning this up, I realized that I have a bunch of awesome friends. When I look at my friends lists in apps like RunKeeper and Fitbit, I smile a big smile about who I’m connected to. Most importantly, I realize that all of this technology is enhancing my relationships, and it reminds me to be deliberate about how I use it.

Recently my partners and I spent some time discussing three of our recent investments – Spanning, Yesware, and Attachments – which are each applications built on top of Google Apps. Specifically, they are built for Google Apps and available in the Google Apps Marketplace or the Chrome Web Store.

Each company is going after something very different. Spanning is all about cloud backup. Attachments is all about getting control of your email attachments. And Yesware is “email for salespeople.” However, they have one very significant thing in common – they are all deeply integrated into Google Apps. In our thematic definition, they are in the Protocol theme.

The Google Apps ecosystem snuck up on us. We have all been hardcore Google Apps users for the past year and are psyched and amazed about all the easy integration points – both into the browser and the various Google Apps. In the past, we would have been more focused on “email as a datastore”, which would have resulted in multiple platforms, including of course Outlook / Exchange and IMAP. However, the pace of iteration on top of Google Apps, and the ease of integration is spectacular when compared to other platforms.

Notably, when the choice of building for Outlook vs. Google Apps comes up, many people who I know comes down strongly on the side of building for Google Apps. Their mindshare for cloud based business apps far outpaces Microsoft. A decade ago, Microsoft made a huge push with Visual Basic for Applications and the idea of “Office as a Platform” and – while plenty of interesting tech was built, something happened along the way and the notion of Office as a Platform lost a lot of visibility.

Theoretically Microsoft’s huge installed base of Outlook / Exchange users should drive real ISV integration interest, but the friction associated with working with Microsoft seems to mute the benefit. And – if you’ve ever built and tried to deploy an enterprise wide (say – 100,000, or even 1,000 seat) Outlook plug-in – well, I feel your pain. It’s possible that with Office 365, Microsoft will re-energize focus on Office as a Platform, but I haven’t seen much yet.

While Google has been building this all very quietly, I’m extremely impressed with what they’ve done. Companies like Yesware are able to release a new version of their app to all users on a weekly basis. For an early stage company that is deep in iterating on product features with its customers, this is a huge advantage. And it massively simplifies the technology complexity to chose one platform, focus all your energy on it, and then roll out other platforms after you’ve figured out the core of your product.

I expect to see versions of each of these products expand to work with Microsoft – and other – ecosystems. But for now, the companies are all doubled-down on Google Apps. And I find that very interesting.

This is a note from your Gmail tech support person (my life in a parallel universe) just trying to help with whatever frustration you are having today.

Over the weekend I noticed that my iPhone (which had recently upgraded to the latest iOS (5.0.1) was now regularly giving me an error from within the native email app. A little box would pop up and tell me that my Exchange Password was incorrect. I use Gmail, but use the Exchange connector on the iPhone (as recommended by Google). Until recently, this was working just fine.

I entered my password 100 times or so in a fit of stubbornness. It worked every now and then. However, when my iPad started borking with the same error message, I decided to figure out the problem.

My search “gmail iphone exchange password incorrect” turned up some interesting stuff. I quickly figured out the problem what the Google Captcha. Apparently the Microsoft connector logs in but then borks on the Captcha which is never surfaced in the connector. Fortunately, there’s an easy way to unlock (or disable) the Captcha in Google Apps.

It seems like Google could fix this on their end without waiting for Apple. Just don’t toss up the Captcha whenever an iOS device hits Gmail. My guess is a recent push on Google’s side broke this as I didn’t notice a real iOS upgrade correlation. While at first I thought it might be iOS 5.0.1, I realized there was a few day delay, pinning the issue most likely back on Google.

Either way, my near term frustration has once again vaporized and I can resume ferociously emailing on my iOS devices.

I’ve recently discovered two awesome tools for helping me manage my contacts in Google Apps. One is a TechStars Boulder company called Rainmaker and the other is a Paris-based company called Kwaga that has an app called WriteThat.Name.

I’ve got a large address book in Gmail (> 11,000 contacts). I get numerous new inbound contacts on a regular basis from people reaching out to me and Google automatically puts their email address in Google Contacts, which is cool. However, it doesn’t put any additional info – either from the email body (which often has contact info in it) or from other sources like Twitter, LinkedIn, and Facebook – which often has a lot more contact info, including a photo.

Let’s start with WriteThat.Name. Once you tie it to you Google account, it automatically scans emails, parses out any contact info it finds, and automagically adds it to the contact record. I’ve been looking for this for a very long time (over a decade) – I’ve never understood why Microsoft didn’t build this into Outlook. Sure – there have been plenty of plug-ins along the way, but nothing that “just worked” invisibly in the background. WriteThat.Name does – beautifully. After using it for a week for free I paid for it. I met the CEO Philippe Laval at lunch the other day in Paris and gave him a big hug. Do yourself a favor – try it.

The next app is Rainmaker. This is from one of the TechStars Boulder teams from this year that is just killing it. You connect it up to your social networks and your Google account. You can then selectively, or in bulk, “make it rain” on your contacts where Rainmaker will use all the magic it can to enhance your existing contacts using whatever information it can find. Like WriteThat.Name, this information is going directly into your Contact database, enhancing it dramatically.

While there is a lot more that can be done, both of these applications make good on the promise of “my computer being smarter than me.” I find that I spend almost no time in my Contacts entering data and updating it any more. All the stuff I need is there – all the time – and I can call, email, IM, chat, txt, or whatever I want without having to search around for the info.

One last hint – before you crank up any program that you give write access to your Google App data, make sure you use Spanning Backup to backup your Google Contacts, Calendar, and Docs data (we are investors in Spanning Cloud Apps, the company that does Spanning Backup.) While I’ve had no issues with either Rainmaker or WriteThat.Name, better safe than sorry!

Jeff Clavier is hanging out with Amy and me in Paris for a few days. We had an incredible dinner last night at L’Arpege - we’d been there once before with another friend (Ed Roberto) about five years ago and it was even better than we remembered it to be. We got home five hours after we started dinner which included an epic cheese course and two dessert courses.

Jeff’s been spending a lot of time on Google+ as have I and many of the VCs and tech early adopters that I know (my VC Circle is my largest circle.) Google+ is rumored to have reached 10m users already and show no sign of slowing. My experience with it has been fascinating – I didn’t do much beyond set up my account, figure out the right login approach since I use Google Apps and Google+ doesn’t yet work with a Google Apps account, and put up a few posts. I’ve got 1400 followers already who presumably simply auto-discovered me via Google’s algorithms (they do have a great social graph already given all the Gmail emails and address books.)

Recently I wrote a post titled Rethinking My Social Graph. I’ve struggled to get my Facebook social graph in order (3000 friends later – lots of acquaintances, not that many friends) and pondered how I use LinkedIn (promiscuously – I link with pretty much anyone). Twitter has been my ultimate broadcast tool and when I think about Google+ vs. Facebook, I realize that the power is the “follow” model vs. the “friend” model.

Facebook has become not that useful for me because while it’s the friend model, I’ve treated it as a follow model. As a result, there isn’t that much intimate communication on it for me, or if there is, it’s completely lost in the noise of the people who I’m acquaintances with. I’ve tried to solve this by sorting them into Lists but there are two problems. The UI for doing this is awful / tedious / excruciating and the control over what you do with lists is weak, especially in places where you really want the control (such as the news feed).

In contrast, Google+ nailed this with the follow model, letting anyone that is interested in what I have to say follow me, while I only follow people I’m interested in. While this is the Twitter model, you get much finer control over both consumption and broadcast through the use of Circles. Now that I have enough activity on Google+, I’m starting to understand and see the impact of this. Oh – and I guess I should start calling it G+ like all the cool kids do.

As Jason and I are about to launch our new book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist I’ve been once again thinking about communication and promotion via social media. My experience setting up the blog and twitter feed for Startup Marriage reminded me how easy it is to get the tech set up, but how challenging it is to get engagement. And my investment in Gnip is showing me the continued geometric expansion of social data across an ever increasing number of platforms.

Get ready – I think we have now finally “just begun.”

Today Google announced that they had now raised the limit on number of contacts to 25,000 (from 10,000) for all Gmail users (including Google Apps users.)  Boom – done – deployed for everyone – and announced in a short and to the point blog post.

70 days ago I wrote a post titled Dear Google, I Have More Than 10,000 Contacts where I bitched loudly about this problem. I have about 6400 actual contact records and the other 3600 had been autofilled by Google’s magic “create a new contact record whenever you respond to someone” feature. This is a great feature as I get 100+ emails a day from people I’ve never communicated with before who I respond to. Suddenly, I couldn’t add any new contacts at all.

Impressively, Google Entreprise Support responded immediately to me. I learned that this issue was high on the priority list and being worked on. Several weeks ago, I was contacted again and let into (under NDA) an early adopter program to test out the new feature. Magically my contact limit was raised and everything worked as planned. And then today they rolled it out to every single Gmail user. Wow.

While I’m psyched with the feature, I’m really impressed how Google handles stuff like this. No one at Google was defensive about the issue – they just addressed it directly. No one said “we don’t support that” – they said “we are working on it.” No one made a big deal about it – they just did it, tested it, and rolled it out. For everyone.

Well done Google.

I just received the “amusing email of the day” from Google. I feel like I’m in one step forward / one step back with Google Enterprise Support. If you read my two recent posts on this, you saw that I started by saying that it’s Time For Google To Get Serious About Enterprise Tech Support and I followed up with My Increasing Love Affair With Google Apps.

A few days ago, I realized that Google was no longer allowing me to enter new contacts. When I checked Contacts in Google Apps, I saw I had exactly 10,000. That triggered some neuron in my brain to fire at which point I did a – ahem – Google search and quickly found that the Apps limit is 10,000 contacts. I complained to Ross (our IT guy) who sent Google the following email:

One of our users has hit some sort of limit of 10,000 contacts – we need this increased as this user needs more than 10,000. Can you let me know how to increase this limit?

Early this morning Ross got the following response.

Hello Ross,

Thank you for your message. I understand that you are inquiring about the Contact limit per user for a Google Apps for Business account.

This is expected functionality at the moment and we suggest that you remove some of the contacts that you don’t use to free up some space on your account. You are not able to increase this amount, however if you would like you can submit a feature request for increasing the amount of Contacts each user has. To do this please follow these instructions

1. Login to your Google Apps account.

2. In your dashboard, scroll down to the very bottom on the screen and you will see a link called ‘Suggest a Feature.’

3. Click on this link and you will be able to fill out a feature request.

I hope you found this information useful, Ross and thank you for your understanding.

Dear Google, no, this is not helpful. While part of me fantasizes about never meeting anyone again in the future that I’d want to put in my Contact database (that’s the introvert part of me), my business dictates that I meet lots of new people every week. And CardMunch is relentless about munching their business cards and putting it in my Address Book (or – well – Contact Database). And – you are now the source repository for all of these dudes and dudettes!

I can’t imagine any particularly good reason why 10,000 would be the limit, or that I couldn’t simply pay you money (I will!) to get 20,000. Yeah, that seems like plenty – how about 20,000? Yeah, I know, we’ll never need more than 64K of RAM in a computer.

At Foundry Group, we have now completely switched to Google Apps. This started in August when I decided to Try Gmail For A Week. Five months later I am ready to declare this experiment a complete success.

As every day passes, I find a new magic happy thing that ties my life together better. Today it was Google rolling out a bookmark importer for Delicious.  Amy and I have been heavy delicious users, although I stopped a while ago when it was uncertain what delicious’ future was. Amy kept asking me what the long term solution was now that we are on Google Apps – it turns out that the answer is “import your Delicious tags into Google Bookmark and keep on going.”

About once a week I’m stymied by something, but the +1 each day nets out to +6 for the week. That’s fine for me – I figure out a work around and usually, voila, as if the $GOOG could read my mind, the thing that didn’t work right or didn’t exist suddenly appears.

Yesterday’s magic was finally connecting up my Youtube account (which was connected to my personal Gmail account) to my Google Apps account. Ahem – it did exactly what I wanted it to and now my Youtube life is smooth and happy again.

And even when I publicly criticize Google, they react amazingly well. A month ago I wrote a post titled Time For Google To Get Serious About Enterprise Tech Support. Within an hour of it going up, I got an email and a call from the head of Google Enterprise support. We talked through the issues, he acknowledged certain weaknesses, talked about what they were doing to improve things, and listened carefully to my very specific feedback on a few things. He connected up with our IT guy (Ross) and they spent some time going through our experiences. Again, he listened to the feedback. And we’ve seen real improvements based on what we told them. Oh, and now that we are through the migration, we almost never need support.

If anyone still doubts Google’s intention in the enterprise, you shouldn’t. Count me impressed.

We are in the final stages of completely switching Foundry Group to Google Apps. This began as an experiment in August 2010 when I decided to Try Gmail for a Week and evolved into an actual plan after Gmail Won Me Over in September 2010. We took it slow to make sure it was actually possible to easily switch from a legacy Microsoft Exchange environment where everyone’s brains were hard wired with Outlook and Windows and shared calendars managed by multiple assistants were a critical business function for a relatively small number of people who travelled constantly.

It’s been a huge success. Oh, and a bunch of Mac’s crept into the organization at the same time. I’m now 100% Mac and am amused by myself whenever I try to do something on a Windows machine (after using Windows or DOS for my entire professional life.) And the integration / proliferation with iPhones and iPads is entertainingly sweet.

For all of the success with the migration to Google Apps, there is one very big obvious thing missing. Google doesn’t have an enterprise support approach. We are lucky in that we have lots of friends at Google so when we need to do weird things (like – ahem – port my Google Voice number from my Gmail account to my Google Apps account) we are able to find someone to do the magic for us. Or when the Google Apps Migration for Microsoft Exchange tool crashes in the middle of the night on a mailbox migration that is 10 hours into its conversion, we can find our way to someone that actually works on this tool who makes some changes to the backend processor that fixes the problem. And, when this happens on another mailbox migration, we can get to them again to help us fix the problem while they debug the tool for our error case.

Now, there is a Google Enterprise Customer and Partner Site and there is plenty of Google Apps enterprise level help on the web. But that’s not the issue. At 7am, when the guy doing the migration checks in and sees a error message that says something like “Failure: While migrating Email for user=xxx@foundrygroup.com to Google user=xxx@foundrygroup.com Error:80041065″ you kind of want to call 1-800-HELPMERIGHTNOWBEFOREANYONESHOWSUPATTHEOFFICE.

There are nice, well proven pricing models for either (a) per instance support or (b) per user annual support. And, if Google wants to be price disruptive, just charge 10% of whatever Oracle or Microsoft charges. Or be like WordPerfect and charge nothing. But put a real enterprise level support organization behind this with humans to call.

The really cool thing about Google Apps is that once you are migrated, there doesn’t seem to be any need for support. I’ve been using Google Apps for four months and I don’t believe I’ve had a single issue that I couldn’t figure out myself. I’ve seen a number of new features automagically roll out and I’ve just started using them. Basically, the post conversion / deployment experience has been superb. And, someday, when Google finishes a real single sign on approach between my Gmail and Google Apps account and finishes their migration to their new infrastructure so I can really use things like Youtube on my Apps account without having to log out of apps / log into gmail / logout of gmail / log into apps to save stuff, I probably won’t even notice that there is any complexity.

Regardless of if and when Google ever gets around to this, I want to thank all of my friends at Google for their help whenever issues came up. You guys are awesome.