In general, I love Gmail. While Amy likes to complain to me about how ugly it is, I don’t even see the UI anymore as I just grind through the endless stream of email that I get each day. My biggest struggle is figuring out how to keep up, without the email ending up dominating everything I do. In the past year, this has gotten a lot harder, but I continue to try new things.

Fortunately, spam is almost non-existent for me. We invested in Postini, which Google ended up buying, and it’s been a joy to have flipped a switch almost a decade ago and had spam go from “overwhelming” to “almost nothing.”

Every now and then, I get a flurry of spam from a new attack before Gmail figures it out. Today was one of those days – I had about a dozen things that looked sort of eBay notification like but with Arabic characters. So I hit ! and marked them each as spam as I was going through my inbox. Suddenly, my inbox reloaded and I got the following message.

I expect that by the time I finish writing this post I’ll have access to my inbox again. But stuff like this makes me physically uncomfortable – my morning routine was just interrupted and the machines decided I don’t get to access my email for a while.

While plenty of folks complain about the ambiguity and lack of precision around many of the issues surrounding Google apps, and more specifically the general lack of support, I usually don’t worry about this much. However, in the last month I’ve had two issues that caused me to remember that I’m increasingly less in control and the machines are increasingly more in control. This is one of them; the other was that I noticed an incredible slow down of performance of Gmail – just for me. After a week of pressing on it, the response from Google enterprise tech support was “you have too many things hitting IMAP – disable all of them.” A quick look at my Google Dashboard showed around 100 different apps that I’d authorized to access my account. I cut it down to about 30 – and got rid of several that I knew were high traffic that I liked, such as the awesome new Mailbox app – and things sped up again after 24 hours.

I recognize that if as we hand over control to the machines, they will make mistakes. That’s ok. But it’s jarring when one doesn’t have control over it, even for a little while. And yes, my Gmail is back up.

I’m finding myself using Google+ more and more. I recently decided that the long game Google is playing is absolutely brilliant. They are being understated about it but doing exactly what business strategists talk about when they describe the long game as the one to play.

Rather than making a bunch of sweeping pronouncements, struggling to jam together a bunch of random crap in a big bang release, and then worry about staying involved in a feature race with a competitor, Google is continually experimenting with new functionality, rolling it out broadly in a fully integrated fashion on a continuous basis, and providing it as a core part of an ever expanding thing that is getting more and more useful by the week.

By now I hope you are saying something like “What the fuck is he talking about – Facebook is crushing Google+” or something like that. Yeah, whatever. That’s why it’s the long game that they are playing.

Here are some examples.

I live in Gmail. Suddenly, I found this magical thing called Circles to be useful. When I get behind on my email, I simply go through a few of the circles (Foundry, Foundry Ents) and clear the email from my partners, my assistant Kelly, and the CEOs I work with. I have persistent chat up – I find that 80% of my chats now go through Gchat (the other 20% are Skype, and they are almost always requested by someone else.) And now that there are Hangouts integrated, many of these are videos.

Google Voice is my Phone Number. I used to have desktop phones. I don’t anymore – I have a Google voice # and an iPhone. I give everyone my Google voice #. It works everywhere. I never think about what phone I’m using anymore. And I do many calls via the computer.

Google Hangouts is my new Calendar Invite. I hate the telephone. Hate hate hate. But I don’t mind chat. And I don’t mind a Google Hangout / video call. All of a sudden I can make invites from Google Calendar that are Hangout invites. Done – every phone call / conference call is now a Hangout.

I live in Chrome. I have several computers. I never notice the difference between them. I’m downstairs at my place in Keystone right now on my Macbook Air. When I go up into my office, I’ll be on my treadputer with a different Macbook Air (an older one) connected to a 27″ monitor. I switch regularly between the two throughout the day and don’t even notice.

Now you are thinking “Ok Brad, but other than the Hangouts, Circles within email, and Hangouts within Calendar, what are you using Google+ for?” Just those three things have completely changed my workflow massively for the better. And they just showed up for me one day – I didn’t have to do anything.

In 2012 I used all the normal Google+ stuff. I reposted content there. I followed people. I occasionally chatted, commented, or +1ed. Facebook-like features. But I didn’t care that much about that stuff – yet.

All of a sudden I’ve got Communities. I’ve got Events. I’ve got Pages. And Hangouts, and Circles integrats seamlessly with each of these things. And they are nicely integrated with Gmail and Calendar. And suddenly I can do On Air Hangouts. And, I can record them automatically and save them to my Youtube channel. Keep playing for another few years, user by user, company by company, integrated feature by integrated feature.

Yeah, it drives me batshit that Google still things I’m brad@feld.com, brad@foundrygroup.com, brad@startuprev.com, and brad.feld@gmail.com. Some day they’ll integrate these. And as I approach 25,000 contacts, I’ll probably start bitching about how this limit is ridiculous, just like I did at 10,000. But I can deal with all of that.

Google – thanks for playing the long game here. I wish more companies, especially other tech companies, did this especially when they have massive resources. Sure – some think they are playing the long game, but they are really playing the short game with a bunch of things that take a long time for them to get out the door. Different game.

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.

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.

I entered Gmail hell yesterday morning. Whenever I sent an email from within a browser, I got a 707 error back and Gmail would go into an endless “Retry” loop. It was early Monday morning and I wasn’t ready to deal with this, so I grabbed my iPad and did a bunch of email on it. I didn’t connect that the client was working fine, but the browser version wasn’t until I got the office.

The answer was a simple one once I figured it out. I disabled all the Google Labs and it magically started working again. I then re-enabled Labs until I found the one that was causing the 707 error – the “Background Send” Labs. Apparently something broke over the weekend with Background Send and the newest browser version of Gmail.

If you are getting a 707 error, just turn off Background Send. That should fix it.

Consider this a public service announcement as of 11/8/11. When I searched Gmail 707 Error in Google, I didn’t find anything that referred to this. I found a few “clear your browser cache” suggestions, which didn’t help. I also found plenty of “I’ve got this problem” with no answers.

We did contact Google tech support via email and got a response back later in the day to turn off Google Labs to see if that fixed the problem. I also got a similar response from my special magic wormhole tech support line to Google engineering.

This was on the heals of a weekend of Gmail / iOS hell. My email clients on my iPad and my iPhone unexpectedly stopped working on Friday – constantly asking me to login to my Exchange account (I’m using the Exchange connector to access Gmail.) I didn’t figure out what the issue was until Sunday afternoon when I realized that the Gmail iOS app was interfering with the iOS mail app. I’d downloaded the Gmail app on both devices when it came out. It was crappy, but when Google pulled it from the app store, I thought it was novel enough to leave on my iOS devices for a while. Error! Once deleted it, email went back to normal.

Google, I love you, but please amp up the QA!