Yesware

I’m a solo runner. While I regularly get asked to go on runs with other people, I almost always decline, as one of my great joys is to run alone. There is one exception – I love to run with CEOs and founders of companies. There are some great stories about the outcomes from these, like my runs with TA McCann that resulted in our investment in Gist . I’ve run marathons with TA , Matt Blumberg (Return Path CEO), Matt Shobe (FeedBurner co-founder), Herb Morreale , and a bunch of people including my partners Jason and Ryan . ...

Let’s start with a brief history of my investment-led fight against the perils of spam and my never-ending love of SMTP. We were investors in Postini and my partner Ryan sat on the board. It transformed my life – with one minor change of an MX record some time in 2002 all the spam in my inbox disappeared. Well – it disappeared before it got to my inbox. Or even my server. The awesomeness of Postini was that it was the first cloud-based email anti-spam solution. And it was a beautiful thing that Google acquired in 2007 for $625m . ...

On Monday we had a Foundry Group portfolio company sales summit. We are fortunate in that we’ve got a bunch of amazing sales execs in our portfolio, including several CEOs like Howard Diamond of MobileDay and Matthew Bellows of Yesware who have long histories selling and building sales organizations. The “enterprise sales software ROI analysis” as a selling tool comes up over and over and over again. And most people blow it, or try to bullshit their way through it, or put together something that is clearly not credible. ...

Yesterday Yesware announced that Battery Ventures led a $13.5m round that we participated in . A few days ago Xconomy wrote a great article about the very first Yesware board meeting on April Fools Day, 2011 . When I reflect on the journey of Yesware over the past 2.5 years it’s a pretty awesome example of a company going from a seed investment with three founders (Matthew Bellows, Cashman Andrus, and Raj Bhargava) to a rapidly growing 40 person company. ...

I’m spending the day working at Yesware . I’ve been an investor from inception and love what this company is doing. I also love the culture – I wrote about it in my post The Monastic Startup . If you use Gmail and Salesforce and are not also using Yesware, take a look at email for salespeople right now. It’s an atypical day for me. I was supposed to be in DC all day today and tomorrow. I had full days of meetings, including two Startup Communities related events – one with the World Bank and one with a Congressional Caucus on Innovation. I had a few company meetings along with some stuff I was exploring. And I was going to drop in on 1776 and check it out. ...

Yesware just announced a $4 million financing . I’ve joined the board. If you are a salesperson who uses Gmail, go download and try it now . I’ve been using Yesware since the first alpha release. While I’m theoretically not a salesperson, I believe every CEO and professional plays the role of a salesperson. And many people, especially in young, fast growing companies, are salespeople even if that’s not their title. As far as I’m concerned salespeople are the unsung heros of most US companies. ...

Last week at our Yesware board meeting, we talked about the idea of “the monastic startup.” This was a phrase that Matthew Bellows, Yesware’s CEO, came up with, and it characterizes the culture they are creating at Yesware. It embodies two concepts: The monastic startup is a place where engineers do the best work of their lives. This place involves work with long stretches of uninterrupted time. ...

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. ...

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. ...