Fred Wilson had an excellent post up this morning titled Social Media’s Secret Weapon – Email. I completely agree that email is the key communications channel for social media and have written about this before in posts like 100% Click Through Rate, Email – The Original Social Graph and Email Is Still The Best Login.

I’ve been investing in email related stuff for over 15 years going back to Email Publishing, my very first Boulder-based investment which I believe was the very first email service provider (ESP) and was acquired by MessageMedia which was then bought by Doubleclick. Fred and I are both investors in Return Path which he calls out in his post as the category creator and market leader in email deliverability. I love Return Path as a company and am incredibly proud of what they’ve done as a business.

My partners and I have continued to invest aggressively in what we believe is social media’s secret weapon which we refer to as the comm channel in a hat tip to the TV show 24. In Fred’s post, the comm channel is email. Our investment here is in SendGrid, a company that came out of TechStars Boulder 2009 and is one of the white hot companies in Boulder. They directly address the problem Fred describes which every software developer knows is a pain in the ass, uninteresting, hard to do well, but needs to be done right. Every web app sends transactional email – rather than build all the code yourself, just let SendGrid to it. They are now doing it for over 24,000 companies, sending out over 60 million transactional emails a day, and just sent their 10 billionth transactional email.

But email isn’t the only comm channel. Everyone that uses apps on a mobile phone is likely experiencing push notifications as an increasingly important as a form of engagement. While mobile phones used to only really work effectively with SMS, you now have SMS, email, and push notifications. So we invested in Urban Airship who does for push notifications what SendGrid does for email. Like SendGrid, they are growing like crazy, are in use by over 10,000 customers and have sent over 3 billion push notifications.

My message to all web developers – if you are serious about what you are doing, focus on your app. Don’t waste precious development time on all the activities around the app. You likely no longer sit around with a screwdriver setting up a server in a datacenter – instead you are using a cloud provider like Rackspace or Amazon.  Don’t spent your time coding up an email notification infrastructure – use SendGrid. And if you are a mobile developer, don’t waste your time writing a bunch of code for push notifications – use Urban Airship.

Most importantly, don’t ignore the thing that will actually make your web app get adoption and retention – comm channels!

Over the past year the amount of emails I receive on a daily basis from entrepreneurs has reached a point where I can’t deal with it any more.  My partners at Foundry Group feel the same and as a result we’ve moved to twitter to deal evaluation. 

If you are interested in talking to me about a potential investment, please just tweet it.  Limit yourself to 140 characters – that’s more than enough to describe what you are doing.  Optimally, you’d DM me, although I realize that I have to follow you for this, so just use @bfeld in your tweet and I’ll see it.  And please – don’t sent me multiple tweets – that kind of defeats the purpose.

After downloading Skype 4.2, I realized that I could now invite all of my Facebook friends who had Skype accounts to my Skype contact list.  So I did.  Unfortunately the Skype UI for this sucks so I had to go through about 1,000 entries a screen of five at a time unchecking the Facebook friends I didn’t want on Skype.  I ended up inviting about 280 – fortunately I was on a conference call for the thirty minutes it took me to grind through this.

The data field used for the match was email address.  Shocking, I know.  It’s the same data field used to log in to Facebook and Twitter.  Google sort of uses email (at least the gmail) account for their authentication, although now that I have both my gmail account (brad.feld@gmail.com) and my email account (brad@feld.com) in Google’s system, I am constantly having to fight with the “reauthorize me to access that thing via brad.feld@gmail.com) game” since Google hasn’t solved for multiple email addresses yet.

More and more sites are integrating Facebook Connect, Twitter “Connect”, or both.  Yahoo has such a golden opportunity to do this and own it but they blew it.  Google seems to have also missed this and ceded it to Facebook and Twitter for some reason.  Microsoft has been trying for a decade first with Passport and now Live ID. And then there is Skype with their 20m simultaneous users.  Or Amazon with their gazillion users authenticating via email.  And then there’s Barnes & Noble – if I want to create an account I get to use my email address.  And the list goes on and on.

Facebook and Twitter are in a perfect position to own single sign on.  I just don’t understand why Yahoo and Google blew this although I don’t really care.  What I do care about is that there seems to be a natural convergence on email as the user id and authentication via widely pervasive services like Facebook and Twitter rather than entertainingly complex approaches like Oath. 

I predict email is going to become even more important in the next few years.  There’s no reason for me to have a phone number any more – you should just be able to contact me via brad@feld.com.  And that should authenticate me anywhere.  And – as a messaging protocol – I should be able to use my “inbox” (wherever or whatever it is) as my central notification point.

It’s remarkable that 15 years after commercial Internet email started to proliferate, it is still at the root of all the commercial Internet activity.  Very very cool.

I was thinking about how to drive CTR’s up via different mechanisms this morning when this email arrived in my inbox.

I remembered talking about high CTR email response rates with Dave McClure and Shervin Pishevar when we were in DC on our Startup Visa trip at the beginning of March.  I’d forgotten about this conversation until this email showed up while I was thinking about this.  Of course, I clicked to see where Dave had tagged me (it was on a Huffington Post article about innovation.)

I thought about it for a few more seconds and realized that to date I have a 100% CTR on an email from Facebook that says “<X> tagged you on Facebook.”  I can’t come up with anything else that I have a 100% CTR on, but I’m now looking out for it.

Do you have any examples of transaction emails like this you receive that have 100% (or even 50%+) CTRs?

I’ve been obsessed with the notion of email as the ultimate social network for a while.  I wrote a post in 2007 titled Social Networks In Obvious Places that catalyzed me to thing harder about this as an investor.  I eventually decided that the email address is the ultimate reference id for one’s current online identity and that it was ludicrous to ignore this notion. This ultimately led to my investment in Gist in 2009. 

Today, there are a number of folks approaching different parts of the problem.  I believe the underlying data architecture and approach is critically important, as email resides in many different data stores and move through many different systems.  In addition, there are numerous other applications that use email as the key reference id independent of username (LinkedIn, Twitter, and Facebook come immediately to mind, but there are thousands of others.)  There is no question in my mind that the web (or the cloud if you like) is your friend in this scenario.

This morning, I noticed that Microsoft had released a beta of Microsoft Outlook Social Connector for Outlook 2010, 2007, and 2003.  I’m running Outlook 2007 on my desktop at home so without thinking too hard I downloaded it, installed it, restarted Outlook, downloaded the LinkedIn connector (the only one available for 2007), restarted Outlook again, and started cranking through email.  I liked the Email Connector window that appears at the bottom of my Inbox view, but I noticed that none of the LinkedIn data seemed to be appearing for my specific contacts.  I didn’t think much of this and figured Outlook was doing something magical in the background (since various info from my Inbox and Calendar started appearing in this view.)  I noticed a few things I didn’t like, such as the every calendar item taking up two lines in the display because the second line was an invite.ics file, but I figured that was just beta stuff.  After an hour or so, I had to jump in my car and head to Denver for a board meeting. 

Once I got into AT&T cell phone range (about ten minutes from my house) I swiped left on my iPhone and typed in the last name for a CEO of a company I’m on the board of.  I noticed that I had two entries for him.  This was strange because I’m meticulous about keeping my address book clean and deduped.  The first entry didn’t have his phone number.  That was really strange since I call him regularly.  The second entry did and looked like the correct record.  I called him, but something was bugging me.

After we talked, I did this again to call another person.  Same issue.  This time I noticed a picture with the little LinkedIn logo on the first entry, but again no phone number.  The second entry didn’t have the LinkedIn picture, but had the correct phone number (and full entry).  By this point I’d figured out what had happened.  I called Amy, told her to shut down my computer at home (I usually leave it on during the day) just in case my new friend the Outlook Social Connector could be stopped before it imported my entire LinkedIn file as new contact records.

I was annoyed throughout the day that I’d munged up my address book.  Tonight, when I got home, I hopped on another board call.  I fired up my computer, uninstalled the Outlook Social Connector, and then spent a few minutes poking around in Outlook contacts trying to find an easy way to delete all the new records.  I fought my way through a few different Outlook contact views and couldn’t figure out how to get the records to consistently appear.  If I searched by name, all the dupes came up.  But if I went into a list view, no such luck – only the correct record appeared and the new LinkedIn ones were no where to be found.  I manually started scrolling through my address book on my iPhone while on the call but by the time I got through the B’s I realized this was an idiotic way to do this and there must be a better way.

A few minutes later it occurred to me that Outlook might have created a new “subfolder” in the contacts view and put all the LinkedIn ones there.  Lo and behold it did and all I needed to do to get rid of the 1800 new contact records was to delete the LinkedIn folder.  Done.  After some happy iPhone syncing they are all gone from my iPhone also.

The decision to take this approach at a data level is beyond comprehension to me.  Almost 100% of the duplicate LinkedIn contacts shared the same email address as my Outlook address records.  I didn’t want a NEW contact record for each LinkedIn one, I wanted them to be “magically attached” to my existing contact record.  So – when I look up Brad Feld, I don’t get the “Brad Feld” Outlook contact record and the “Brad Feld” LinkedIn contact record.  They are both brad@feld.com – that’s all I want.

So – be forewarned – unless you want to gunk up your address book with duplicates, don’t install the current beta of Microsoft Outlook Social Connector.  Maybe I did something wrong, or have a weird configuration of Outlook 2007, but I simply did a straight install.  Maybe Microsoft will fix this in the next version, but it definitely doesn’t seem ready for prime time, especially on live data.

I’ve been an Internet email user since early 1984 when I got my first Project Athena account as an undergraduate at MIT.  Notwithstanding all the “email is dead” messages over the years, I continue to use email as my primary online communication mechanism.  There are an enormous number of things that frustrate me about email, most notably the lack of fundamental innovation in email clients and servers.  That said, as a messaging tool – it still dominates for me.

Several years ago I started saying that “my social graph is in email.”  I found it interesting that Facebook and LinkedIn used email as a primary messaging layer to remind me to come back to Facebook and LinkedIn respectively to check what was going on.  This signaled confirmation to me that these systems were making sure they were using the most persistent messaging layer to build and reinforce their social graphs.

For whatever reason, the primary email product providers have been either painfully slow at realizing this or have decided to ignore this.  Facebook and LinkedIn have benefitted massively from this, but the biggest recipient of this neglect is Twitter which has created an entirely new messaging protocol (think Twitter API as analogous to SMTP).

Suddenly, in the past year, entrepreneurs have woken up to the potential of the email social graph.  As I’ve mentioned before, we invested in Gist to directly address this opportunity.  Xobni is another well known company that is attacking this.  But another intriguing fact is the number of younger entrepreneurs that are working on this problem.  Each of the TechStars locations (Boulder and Boston) has a company that – at its core – is built around the premise of email as the original social graph.  In addition, as a mentor in the fbFund Rev 2009 program, I’ve recently started working with another company working on yet a different angle to this problem.

Now, these companies aren’t creating new email clients.  They are working on products or web services that take advantage of all the implicit information generated by your email activity.  They aren’t limited to just email (if you are a Gist user, you understand this well), but use email (name@domain.com) as a key information pivot point.  If you step back and think about it, while http://www.facebook.com/bfeld is new and full of yummy chocolaty goodness, brad@feld.com is really my “unique” identifier.

I’m not going to talk about the three new companies I’m working with on this problem yet – I’ll let them “launch” on their own timetable and I’ll talk about them when they are ready.  In the mean time, I’ve continuing to look to talk to more people that share this premise.  If that’s you, feel free to email me.

The amount of mailing list spam I’ve been getting has been steadily increasing with a huge jump in the last few months.  I was perplexed by it – this isn’t real spam (they are all opt-in mailing lists – many of which I recognize the associated organization.)  However, I hadn’t opted-in to any of the lists!

Some were political lists, some were technology lists, and some were random things.  As the election got closer, the political ones increased.  Today, as I was hitting delete over and over again I realized that I must have been on a seed list that got passed around between organizations.  This is a pretty typical spam thing and gets 99.999% blocked by Postini (my anti-spam system), but until recently I hadn’t connected the dots on it from legitimate opt-in emails since I actually want to get the emails I’ve opted in to.

Specifically, any mailer who understands CAN-SPAM and cares about reputation won’t share their lists this way.  At the minimum, I’d get an opt-in request from the new list which – while not great – is at least tolerable.  This phenomenon isn’t limited to the political lists – I’ve been noticing it more broadly across all the tech email lists.

In addition, it appears that I’m getting added to email lists whenever I give someone my business card.  I find this particularly annoying for all the non-profit organizations that I’m involved with.  My reaction to getting email spam from them is negative, which I presume is the exact opposite of how they want me to react.  While this practice doesn’t actually violate CAN-SPAM, it’s definitely in the category of "bad email practices" in my book. 

We’ve been involved in this arena as investors for a long time with both Postini (on the email security side – now part of Google) and Return Path (on the email deliverability side).  I’m really proud of each of these companies – they’ve both created real businesses helping eliminate bad email and insure that good email gets through to the inbox. 

Fred Wilson just wrote a long post on why his firm – Union Square Ventures – recently invested in Return Path.  After thinking about my mailing list spam issue, I think we are going to have another major iteration of spam dynamics that we’ll have to address and Return Path continues to be extremely well positioned to do it.

BTW – do you want to Simplify The Season with Dell Small Business?  Unsubscribe.  Delete.

I noticed two articles in the NY Times this morning that pressed my email theme button.  The first was actually from yesterday – Lost in E-Mail, Tech Firms Face Self-Made Beast.  The second was In the E-Mail Relay, Not Every Handoff Is Smooth.

Both are interesting, but relatively light weight articles.  That’s not really a surprise since they are aimed at the mainstream public instead of Joe Techie.  There are a few fun things in Lost in E-Mail … such as the new and exciting "Gmail E-Mail Addict" feature that lets the user take a 15 minute break by hitting a button or a neat program called Rescue Time which tracks how much time you are spending in different applications (I used it for a few weeks until I got bored of seeing how much time I was spending on email.)  However, neither really gets at the core of the issue they are addressing, which is something approximating "how can human beings deal with the current onslaught of email?"

I find it more interesting to see what my "high performance / lead user friends" are struggling with.  I’m an inbox zero guy (I go to bed every night with no emails in my inbox – where "no emails" is an approximation for "less than 30 and nothing urgent.")  I don’t save things in folders for a future response (I think that’s equivalent to deleting them) but I do put things on my task list when I need to remember to respond (my task list is never longer than something I can clear with an hour of focused effort.)  I regularly check my email throughout the day, but I don’t let it interfere with me when I need to concentrate on something and I’ve trained myself not to look at my handheld until I’m truly bored in a meeting.  I rarely go to the bathroom in the middle of a meal out with Amy to sneak a quick look at my email.  As a result, I don’t struggle with email – it’s just an efficient (and integral) part of my work communication.

A set of my friends are really struggling with it.  I commonly hear the "I’m way behind on email" refrain.  Several of my friends have deep disdain for email, including one who basically equates it to "homework" (hey – I liked doing homework!)  Another friend decided to take the summer off from using email (while I was happy to hear from him when he called me to thank me for doing something, it was at an inconvenient time and I thought he must have needed something urgently when I saw his name pop up on my phone.) 

When I sit on an airplane next to someone doing email, I like to observe their pattern as I drift off to sleep (watching them helps me fall asleep faster.)  A remarkable number of people have a "hunt, click, read, and then don’t respond" approach to email where they read messages that they selectively choose to read but then don’t respond or delete, resulting in yet another "read" message clogging up their inbox.  These people clearly need a lesson in processing their email.

I’ve got a long list of additional examples, but you get the idea.  There is a deep sociological thing going on.  A decade ago email was lauded as the savior of business communication.  Today, it’s a giant pain in the ass for many people, although it’d be interesting to see how they’d cope without it.  The fact that it’s popping up in the weekend NY Times reinforces that the problem is continuing to build toward a tipping point, which reminds me that there is a big opportunity out there somewhere. 

BTW – can someone tell the NY Times that it’s ok to use "email" instead of "E-mail" – even Wikipedia says so.

In my I Love Email post, I got a wonderful comment from my friend Fred Wilson that said:

to each his/her own these days. my kids use facebook and text messaging for the most part but now that they have email on their phones (bberry and iphone) they use that as well, but it’s not their primary messaging system. i still use email as my primary method, but as someone else said, it’s the new snail mail. i hate doing it and its a chore. i called it "homework" on twitter today. that’s how i feel about it. i find text messaging and twitter are best for me, but they will only be better for a while. they will get more noisy and i’ll have to move to something else. i don’t use facebook messaging at all. when people send me facebook messages, they are talking to a black hole

To that I say "Correct!"  When I say "email", I’m really saying "messaging", although I hate the phrases "messaging" and "collaboration".

Deva Hazarika, the CEO of ClearContext, has an excellent followup post titled Three next steps for email.  In it he identifies three areas where email clients haven’t kept up with the pace of change (volume, integration, and context.)  I’ll add a fourth – social graph – I only want one of them!

Email.  Email.  Email.

My partner Chris Wand just put up a post titled Did Darwin Skip Over Email?  Every now and then the "Email is dead" meme makes the rounds and lights up TechMeme.  The right answer isn’t that "email is dead"; it’s that new and exciting stuff is happening around the use of "messaging" and it’s time for some new innovation.

For those of you who suggest that I switch all my email over to Facebook, I say to you "Laugh-a-while you can, Monkey Boy."

If I had to do all my "messaging" in Facebook, that’s what would happen to me. And since Lithium is no longer on credit, I doubt I’d be very pleasant to deal with.  Rather than facing this reality, help us help out by bringing us your new email (ahem – or messaging if you want to be politically correct) innovations.