Greg Reinacker – NewsGator’s founder and CTO – has a two part roadmap post up. His first post summarizes what NewsGator has been up to over the past 18 months. His second post talks about where NewsGator is going with their products. I’ve heard plenty of chatter lately about the fundamental differences in enterprise software between shrink-wrap software, appliances, and hosted (or SaaS) software. Most VCs I know have fallen in love with SaaS – often without understanding the fundamental economics of the SaaS model (“trendy is good – thank you SFDC”.) Others are convinced there will never again by any life in enterprise software – which is just fine with me as I love a counter cyclical trend (e.g. enterprise software is my friend again – but don’t worry, I’ll stay away from the “marketing automation” vertical.)

I’m looking for recommendations for headphones for running. I’ve been using some from Sony for a while – they are ok, but I’m having some trouble with how the right one fits (I guess my ears are different sizes – how exciting.) If you have any suggestions for sport headphones, can you leave comments here?

A few days ago I wrote that there wasn’t enough talk about failure. I had an awesome run tonight in the mountains behind my house and pondered – among other things – some of my early failures. As my mind wandered and I tried to keep from stumbling on the rocks, my thoughts drifted to my first software company – Martingale Software. I co-founded Martingale Software in 1984 with three fraternity brothers. Three of us were second term freshman (me, Andy Mina, and Sameer Gandhi) and one was a senior (Dave Jilk). After Martingale failed, Dave joined Viewlogic Systems as their first non-founder employee and – after having success there – went on to start Feld Technologies with me (which succeeded.) After college, Sameer had a strong run at Oracle in the late 1980’s, then spent some time at Broadview, before joining Sequoia Capital, where he’s been since 1998. I’ve lost track of Andy.

I’m two degrees of separation away from two people that died tragically yesterday. I’ve been thinking about it on and off all day. Both were friends of very close friends of mine. One died in a plane crash – he was in the prime of life, a huge success, and apparently a very happy person. He was flying his new plane with an instructor – they crashed and both died. The other was a young mother who was out for a bike ride with her daughter. A truck lost control and ran her over. I’m not sure what happened to the daughter.

Our good friend Mollie Fager (the executive director of The Dairy Center for the Arts) has a great rant up on the New West Network blog on “why opera rules” titled Opera: It’s Not for Wusses. In my endless effort to avoid wussness, I’m a believer.

Ryan McIntyre pointed me at a car that gets 3.14k miles per gallon. Now, if it only ran on pi.

I received a lot of interesting and positive feedback on my post on talking about failure. There’s no question that enlightened entrepreneurs get the value of failure and generally enlightened people have noticed the absence of VCs (and entrepreneurs) publicly talking about it for a variety of reasons. Adam Green pointed me at a podcast he did with Adam Bosworth (now at Google) discussing his lessons learned from the failure of Reflex. I hadn’t thought of Analytica / Reflex for a long time (I had an original copy and loved it) – and subsequently discovered this useful essay about it on the web.

Thankfully I no longer get fedexed binders of board packages from my portfolio companies in advance of a board meeting. Through the modern miracle of email, the board packages show up in my inbox – hopefully a few days (rather than a few hours – or even minutes) before the board meeting. The board packages tend to show up in three different formats – one that is easy to deal with, one that is ok, and one that sucks.

Periodically FeedBurner gets all their engineers in a room, turns over tech support to the business team for the day, and cranks out a bunch of features. Hackathon III occurred a week ago on Friday and generated a healthy list of new things for all the friendly neighborhood FeedBurner users, including: Map It FeedFlare: Link to Google Maps if you have address info in your post. BuzzBoost Brush-up: Spiffy new BuzzBoost features, including subscribe to feed. Download Tracking Tweaks: UI cleanup on Download Tracking. FeedBulletin via Email: Get email alerts (instead of RSS alerts) for your FeedBulletin feed. IP To Location: Live hits page now displays countries where your items are being viewed. Mobile Feed Stats: Check your stats on a mobile web browser. FeedFlare Scratchpad: Play around with and test out new FeedFlare’s easily FeedBurner Module for Netvibes: See a bunch of FeedBurner stuff in Netvibes. New Email This FeedFlare: Email This webpage instead of mailto: (for non-nerds – this works better). FeedBurner Help: Lots more help. I love this approach to pushing features out.