Brad Feld

Tag: gmail

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 GmailSuddenly, 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 NumberI 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 ChromeI 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!


Gist just released their Chrome extension for Gist in Gmail.  Chrome is my browser of choice for Gmail and I’ve been anxiously awaiting this release.  It’s just awesome.

It’s tightly integrated with both consumer and enterprise Gmail.  It’s fast, light weight, and takes advantage of the huge amount of data discovery that Gist does via the cloud (rather than in-browser).

It’s been really fun to watch my friends at Gist really come into their own in the past six month.  With the release of Gist in Gmail on both Firefox and Chrome, along with the Gist Gadget for Google Apps, they’ve got Gmail now totally wired.

If you haven’t tried Gist, give it a shot.  And if you are a Chrome and Gmail user, make sure you grab the Chrome extension.


About a month ago I wrote a post titled Trying Gmail For A Week.  I haven’t thought about Outlook, Entourage, or Mac Mail for a month and I don’t think I’m ever going back.  It took about a week to rewire my brain for how conversations worked and what the keyboard shortcuts were, but not that I’m there it’s just awesome.

A few weeks ago Fred Wilson wrote a post titled Inbox Zero.  In it he mentioned two Gmail services he found indispensable – Priority Inbox (from Google) and Unsubscribe.com (from James Siminoff who created Phonetag, another great service.)  I agree with Fred on both of these, but have discovered a few extra things that are killer.  I’ll list them below and for balance talk about a few shortcomings.

Priority Inbox: I’ve seen numerous tweets and blogs about how Priority Inbox doesn’t really do much.  These are wrong / misinformed reactions.  The trick to Priority Inbox, like many other things, is to actually use it for a few weeks.  Part of using it is training it by quickly marking things up to “important” (by clicking +) or down to “everything else” (by clicking -).  A small configuration change can make Starred emails (for quick follow up) a different category.  I found that it only took about three days of this before I saw benefit and now (a month later) Priority Inbox gets it right 99 out of 100 times.  I get over 500 emails a day – there is a long list of them that fall in “Everything Else”.  I used to have to check / clear email obsessively throughout the day to stay at Inbox Zero.  With Priority Inbox I’m finding solid email stretches a couple of times during the day are more than enough for me to stay on top of everything.

Unsubscribe.com: Like many people, I’m stuck in the endless “unsubscribe from email lists” infinite loop.  I get vigilant for a few days and do the annoying unsubscribe drill one by one and knock a few off the list, but within a few weeks I’ve got even more.  I’ve never seemed to be able to eliminate all the stuff I don’t want, especially around an election when it all escalates like crazy.  With Unsubscribe.com, I simply click the Unsubscribe button in Gmail and the service gets rid of it.  Don’t bother with the trial – trust me and just pay $19 for the service for a year if endless mailing list email that you don’t want is a problem for you.

Google Voice: I’ve had a Google Voice for a long time but I never fully switched over to it.  The Google Voice integration with Gmail has tipped me over.  I’ve been dreaming about getting rid of my desktop phone for a while – I now find myself almost exclusively doing every call from my computer except when I’m not online (where I have to use my cell phone.)  More importantly, video chat and text chat is completely integrated within Gmail so from one screen I have email, my phone (inbound and outbound calling) Skype-equivalent video chat, and text chat.  While I still use Skype extensively (I’m bradfeld) I find I’m using it much less as I end up using brad.feld@gmail.com instead.

Gist: I’m an investor in Gist and use it for my unified contact manager.  Google Contacts is ok, but has a long way to go.  But Gist integration with Gmail at a data level is superb.  I’m still using Gmail’s consumer service so the integration is primarily at a data level, but I’m now playing around with a full switch over to Google Apps and the Gist + Google Apps integration (via the Google Apps Marketplace) just rocks.  In addition, there’s a new browser-based Gist add-on coming out shortly (hint hint) that will provide direct integration into the consumer version of Gmail.

GooTasks: Since I am an Inbox Zero guy, I don’t keep anything (including paper), but I do have a short task lists of things like blog posts I’m going to write.  I went through an Evernote phase recently but it’s overkill for me.  Google Tasks is perfect, but I didn’t have an obvious way to sync with my iPhone.  Now I do.

There are a handful of annoying things.  The biggest one is that I have multiple accounts on Google (brad.feld@gmail.com as well as brad@feld.com) and they aren’t tightly integrated across all services.  The other is the weak / inconsistent iPhone integration which keeps pushing me toward using an Android phone full time (I’m now carrying both an Android phone and an iPhone.)  My dad’s recent story on the Samsung Fascinate has me seriously considering a full time switch over to Android.

My “while I’m working” migration from a full Windows / Outlook / Exchange / Office world to an almost completely non-Microsoft world has been fascinating.  I’m in Seattle next week including a 24 hour stretch at Microsoft for some stuff – maybe it’ll come up and be an interesting discussion that my friends at Microsoft can learn from.  In the mean time, I think the next big switch will be an organization one completely over to a Google Apps infrastructure.


My week-long experiment with Gmail continues with my first big bump happening last night at around 9pm.  After sending a lot of emails (apparently 500) I received an error message “You have reached a limit for sending mail“.  I tried again.  This perplexed me.  So I clicked on the link.

I read through it and couldn’t figure out what I’d done wrong.  I tweeted about it and immediately heard back that Gmail had throttled me for up to the next 24 hours because I’d been sending too many emails.  I poked around a little to try to figure out if there was a way around this and finally concluded that the solution was to go to sleep and try again in the morning.

When I woke up, email was magically sending again.  I guess I got turned back on in less than 24 hours.  We’ll see what happens today.

Of course, one solution is to use SendGrid.  I’ve just gone and signed up for an account in case I get rate limited again.

In the mean time, Gmail feels slow this morning.  I’m getting used to my new friend, the yellow “Working” link at the top middle of the window.


Ever since I switched to the Mac, I’ve had N (where N is a suitably large number) tell me that I should switch to Gmail from Exchange.  I finally decided to try it for a week and see if it works for me.  Given my Mac experience – where I had to commit and really use it, I’ve decided to do the same on Gmail.

For now, I’m just going to use Gmail (instead of Google Apps) because I don’t want to go through the hell of switching the feld.com domain since I’ve got a bunch of other people (e.g. my family members) on it in a variety of configurations.  That’ll limit me a little as I won’t be able to use the Apps Marketplace, but the benefit is I’ll be able to mess around with a variety of other Gmail stuff.

If you’ve got Gmail addons, hints, tips, and trick, leave them for me here.  At the end of next week, I’ll either be switching to Gmail or heading back to Mac Mail against my Exchange server.