In December I wrote a post titled It’s Not About Having The Most Friends, It’s About Having The Best Friends. Since then I’ve been systematically modifying my social networking behavior and cleaning up my various social graphs. As a significant content generator in a variety of forms (blogs, books, tweets, videos) and a massive content consumer, I found that my historical approach of social network promiscuity wasn’t working well for me in terms of surfacing information.

I made two major changes to the way I use various social networks. I went through each one and categorized each on three dimensions: (1) consumption vs. broadcast and (2) public vs. private, (3) selective vs. promiscuous. These are not binary choices – I can be both a content consumer and a broadcaster on the same social network, but I’ll use it differently depending where on the spectrum I am.

For example, consider Facebook. I determined I was in the middle of the consumption/broadcast spectrum, public, and selective. With Foursquare, I determined I was closer to broadcast and private and very selective. With LinkedIn, I was 100% broadcast, public, and promiscuous. With Twitter, I was similar to Facebook, but with a much wider broadcast and promiscuous. With RunKeeper, very strong on broadcast, public, but selective.

I then looked at the tools I was using. Yesterday I noticed Fred Wilson’s email The Black Hole Of Email and it reminded me that I view email as my primary communication channel for broad accessibility (I try to answer every email I get within 24 hours – if it takes longer you know I’m on the road or got behind) and often respond within minutes if I’m in front of my computer. But I’ve worked very hard to cut all of the noise out of my email channel – I have no email subscriptions (thanks OtherInBox), I get no spam (thanks Postini), I run zero inbox (read and reply / archive immediately), and am very selective with the notifications I get via email (i.e. I check Meetup.com daily, but the only email notifications I get are for Boulder Is For Robots.) As a result, I find email manageable and a powerful / simple comm channel for me.

Tuning each social network has ranged from trivial (15 minutes with RunKeeper and I was in a happy place) to medium (Foursquare took an hour to clean up my 800+ friends to 100-ish) to extremely painful (going from 3000 Facebook friends to a useful set seemed overwhelming.) I decided to clean up the easy ones first and then come up with manual algorithms for the harder ones.

My favorite approach is what I’m doing with Facebook. Every day I go into the Events tab and look at the birthday list. I then unfriend the people whose name I don’t recognize or who I don’t want to consume in my news feed. Since Facebook’s social graph is on the public side, people can still follow me (ala Twitter follow). I view this as a reverse birthday gift which probably enhances both of our lives.

In contrast, I’ve continued to just accept all LinkedIn requests except from obvious recruiters or people who look like spambots. I know they can pay to get access to my social graph – that’s fine – I want them to have to pay someone or work a little for it, not just get it for free, but the benefit of having a wide social graph on LinkedIn for the one time a week I use it to hunt someone down somewhere far outweighs the pain of being promiscuous.

I’ve continued to find and use other tools for managing all the data. One of my new favorites is Engag.io. Rather than getting a stream of Facebook email notifications, I check it once a day and respond to everything that I see. I’ve noticed that I find comments in other services like Foursquare that I was previously missing, and rather than having a pile of clutter in my inbox, I can interact it with once a day for ten minutes.

When I reflect on my approach, it doesn’t surprise me that it’s very algorithmic. That’s how I’ve always driven my content consumption / content generation world and part of the reason it doesn’t overwhelm me. Sure – it spikes up at times and becomes less useful / more chaotic (like it did last year when I realized Facebook wasn’t really useful for me anyone.) This causes me to step back, figure out a new set of algorithms, and get it newly tamed. And yes, Facebook is now much more useful and interesting to me after only a few months of cleanup.

I’m always looking for new tools and approaches to this so if you have a great one, please tell me. For example, the “unfriend on birthdays” approach was suggested several times in the comments to one of the posts and after trying a Greasemonkey plugin, manual unfriending on the iPad while watching TV, and other brute force approaches, I just decided I’d clean it up over a year via the birthday approach. So – keep the comments and emails flowing – they mean a lot to me.

I had a great breakfast meeting at the Cambridge Marriott with Michael Schrage, a research fellow at MIT yesterday morning. We had never met before and I loved the conversation – his brain was bubbling with ideas that are relevant to many of the things I’m interested in, he challenged some of my thinking, and we had a deep and awesome conversation about open source hardware, makers, and MakerBot.

This morning Raj Bhargava (who recently co-founded two companies I’ve invested in – Yesware and SkedulMe) sent me a blog post by Michael titled Tip for Getting More Organized: Don’t. In it Michael makes the argument that the notion of spending time each day organizing your tasks, the concept of email folders, and the idea of productively organizing yourself is obsolete. The money quote at the end is:

“The essential takeaway is that the new economics of personal productivity mean that the better organized we try to become, the more wasteful and inefficient we become. We’ll likely get more done better if we give less time and thought to organization and greater reflection and care to desired outcomes. Our job today and tomorrow isn’t to organize ourselves better; it’s to get the right technologies that respond to our personal productivity needs. It’s not that we’re becoming too dependent on our technologies to organize us; it’s that we haven’t become dependent enough.”

I couldn’t agree more. I spent almost no time “organizing my tasks.” In fact, I no longer have a task list. I have outcomes I’m going after. They fit within a daily, weekly, quarterly, and annual tempo. The daily and weekly outcomes are dynamic – I have to think about them regularly and they change and shift around (I have new ones each day and new ones each week.) I call these my Daily P1s and my Weekly P1s (which I wrote about recently in a post titled Managing Priorities)- the daily ones are the three things I want to accomplish before I go to sleep; the weekly ones are the three things I want to accomplish each week before Monday morning.

But that’s it. I have a daily schedule that is highly structured (and managed by my assistant) so I don’t have to spend a millisecond thinking about who I need to meet with, where I need to be, or what I need to schedule for later. If you know me, you know that I just “go where my schedule tells me to.” I process all of my email with one touch, I write what I want when I want, and I have a strong conceptual hierarchy for prioritizing high interrupt things. I also stay off the phone unless scheduled – if you spend time with me for a day it’s likely that the only time I’m on the phone is with Amy to say “hi – I love you” or have a pre-scheduled call.

I love the notion of focusing on outcomes rather than organization. For as long as I’ve been an adult, I’ve been hearing about, reading, thinking about, and experimenting with different technology to be “more organized and productive.” I’m an aggressive user of whatever exists and when I reflect on where I’m at in 2012 I definitely feel like I’ve gotten to the place where I’m spending almost all of my time and energy on outcomes and achieving them, not on organizing myself.

If you are someone who spends 30 minutes or more a day “organizing yourself”, I encourage you to step back and think about what you could change and how that might shift you from focusing on organizing to working toward outcomes. It’s liberating.

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.

Today’s “founder hint of the day” is to create an email address called founders@yourcompanyname.com and have it automatically forward to all the founders of your company.

I interact with a ton of companies every day. For the ones we have a direct investment in via Foundry Group, I know each of the founder’s names (although with 40 companies, at age 45 – almost 46, there are moments where I have to sit quietly and think hard to remember them.) For the TechStars companies, especially early in each cycle, I have trouble remembering everyone’s names until I’ve met them. And for many other companies I have an indirect investment in (via a VC fund I’m an investor in) or that I’m simply interacting with, I often can’t remember all of the founders names.

Ok – that was my own little justification. But your justification is that as a young company, you want anyone interested in you to be able to reach you. While info@yourcompanyname.com is theoretically useful, in my experience very few people actually use it because they have no idea where it actually goes. On the other hand, founders@yourcompanyname.com goes to the founders. Bingo.

We’ve been using this at TechStars for a number of years and it’s awesome. I’ve set up my own email groups for many other companies, but this morning while I was doing it for another one I realized that they should just do it. Sure – there’s a point at which the company is big enough where you probably don’t want to have this list go to all the founders, or there are founders that leave, or something else comes up, but when you are just getting started, be obsessed with all the communication coming your way and make it easy to get it.

founders@yourcompanyname.com rules.

I continue to be obsessed about email – it’s by far the most significant comm channel I use. And – it’s accelerating, not decelerating, especially as it proliferates across devices as well as other comm channels.

I’ve watched as many of the companies we’ve invested in use email and CRM systems (such as Salesforce) as though they existed in separate parallel universes. I’ve listened to the endless complaints about the complete and total lack of real integration between the two. I’ve watched the workflow, even from very disciplined sales people, and shaken my head in total bafflement at the lack of integration and the perverse contortions the sales person goes through to try to make the two systems work together. And – as I’ve continued to manage the enormous flow of email I get in Gmail, I’ve been searching for more efficient (and effective) ways to deal with it, besides just ignoring it which, while efficient, wouldn’t be very effective.

To address this, we’ve invested in a new company called Yesware.

At the beginning of the year I was kicking around some ideas with my long time friend Raj Bhargava. Raj and I have done a bunch of companies together since we met in 1994. He acutely felt this problem in his most recent company StillSecure as he dealt with the garbage in / garbage out problem of his CRM system. Over a few months we bounced some ideas around until one day he mentioned to me that he’d run into two entrepreneurs in Boston – Matthew Bellows and Cashman Andrus – who were working on something similar. Over a few weeks everyone connected, Matthew, Cashman, and Raj decided to merge efforts, and I agreed, along with Rich Miner at Google Ventures, to provide a seed financing.

A few weeks later we had our first board meeting in Google’s NY office where I discovered Zico Coconut Water. Matthew and Cashman showed us a detailed product road map along with the MVP they were working on and planning to ship in 30 or so days. We spent the entire meeting talking about the product (I’m sure Matthew had other slides but I don’t remember them.) While the first MVP was interesting and an extension of the ideas they had started with, it didn’t feel right to anyone in the room.

Rich and I both suggested – in different ways – that the team delete what they had done so far. We felt they were falling into a classic startup trap as they’d spent three months raising their round and were now anxious to get a product out the door. But they hadn’t spent much time in the previous three months thinking deeply about the product, so their plan was an awkward continuation of their demoware and concept pitch.

At some point in the meeting I said something that Matthew has told me stuck with him. I said, in my most Yoda-like voice, “slow down to speed up.” The seed round was an ample amount of money for them to go for at least a year. Their vision didn’t have an expiration date. Sure – other people were likely working on similar stuff and getting to market fast is always important, but getting to market with something compelling is even more important.

The team heeded the advice, stopped trying to ramp up headcount to work on extending the demo, deleted the product roadmap, and started again. The progress over the next 60 days was awesome as they went very deep with real salespeople on the problem, simplified their product vision, and defined a very clear MVP, release plan, and path to a revenue producing product.

At the time we made our investment I asked Matthew if he wanted me to blog about it. He didn’t – he saw no reason to talk widely about it until the company had shipped something interesting for people to use. That time has come – if you are a salesperson and use Gmail in Chrome, give Yesware a try. And give us feedback.

At Brad Feld’s Amazing Deals, we only bring you shiny happy deals. If you are a Mac user and like to live in a mail client instead of a browser, Sparrow Mail is for you. I paid $10 when it came out but through the magic of daily deals am making it available for $5 for the next 24 hours (up to 1000 copies).

Jason Calacanis even loves it – on G+ he says:

“I’m absolutely in love with Sparrow Mail. It’s made me 10-35% faster in GMAIL/Google Apps.”

For the next 24 hours, you can get Sparrow Mail for $5 instead of $10. Just wander over to Brad Feld’s Amazing Deals and grab it. And be able to say “I got something for $5 that Brad paid $10 for that he then made available for $5 bwahahahahaha.”

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!

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.

Congrats to my friends at Gist for being acquired by RIM.

I met TA McCann, the CEO / founder of Gist at the first Defrag Conference when he took me for a pair of runs along the Denver Creek Path and it’s been a blast to work with him and the Gist team ever since.

Also, congrats to RIM for picking up an awesome team that’s been thinking about and building software for the intersection of social and email since before talking about it was in vogue.