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.