Last night at the TechStars Boulder Mentor dinner I got into a conversation about what makes a better CEO of a new startup – an experienced entrepreneur who’s last company was a failure or a big company executive with a stellar pedigree who has never worked in a startup. Give me the experienced entrepreneur whose last company was a failure 100% of the time. The cliche “you learn more from failure than success holds true”, but more importantly the dude that just came off a failure and is ready to go again is super-extraordinary-amazingly hungry for a success. It doesn’t matter how much money he’s made in his past companies – once he decides to go for it again he’s going to be ready to crush it.

Eric Norlin has a great post up this morning titled A conference is about community*.* In it, he describes clearly the difference between a conference and a trade show, what makes a great conference, and what you’ll get at a great conference. Having been involved in Defrag since it was a germ of an idea and now watching Eric put together the first Glue Conference, he knows of what he speaks. I won’t try to summarize – go read the post (it’ll take you two minutes.) 

After Bill Ritter was elected governor of Colorado in 2006, I was asked to be a member of the IT transition team. We had about a month to review the current state of affairs with regard to broadband, the Colorado IT structure and strategy, and to recommend a CIO candidate. I’d never been on a transition team before so I found it to be an interesting experience. I don’t remember the number of transition teams (I have the number 16 in my head) – they were all busy trying to collect, assimilate, and understand what existed, put together clear recommendations that the new Governor and his staff could build on, while trying to separate a bunch of signal from noise of the outgoing administration.

My friends at Foodzie (TechStars 2008) and Brightkite (TechStars 2007) were both recently named Best Young Tech Entrepreneurs of 2009. There are a bunch of neat links up on the Businessweek.com site: Foodzie Overview Brightkite Overview Foodies Will Welcome Foodzie article Foodzie video Congrats guys. You make me (and everyone at TechStars) proud! We’ll be sure to roast y’all at the TechStars Boulder Mentor dinner tonight.

I stayed at my parents’ house in Dallas on Tuesday night. My mom has been going through a “clean all the shit out of the house” routine and keeps dumping piles of old stuff on me. This trip, I got my high school prom album and my bar mitzvah album. Following is my high school prom picture. My partner Seth just informed me that my fundamental essence hasn’t changed since I was 17. There’s 40 pounds more of it, but at my core I’m pretty much the same.

I did another Beers with Brad event tonight in Vancouver. Danny Robinson and Boris Mann of Bootup Labs pulled it together with some help from their friends and a few sponsors. 150 people showed up to talk about early stage entrepreneurship. For these events, I have a few themes to riff on around entrepreneurship (e.g. entrepreneurial communities, the role of venture capital, and leadership) that are set in my head. Rather than do a presentation, I just get up and talk for 15 to 30 minutes and then do Q&A until everyone is done. I deliberately don’t have a prepared stump speech and what I say varies with each event, but the themes are consistent. I like to just talk off the top of my head because – in addition to requiring zero preparation time – I’ve always felt that overly prepared talks around entrepreneurship are missing the point. Entrepreneurship is messy; if the talk is too tidy, then it’s incongruent with what is being talked about.

I’ve been fascinated with the notion of the Implicit Web since I determined that I was tired of my computer (and the Internet in general) being stupid. I wanted it (my computer as well as the Internet) to pay attention to what I, and others, were doing. Theoretically “my compute infrastructure” should learn, automate repeated tasks (automatically), figure out what information I actually want, and make sure I get it when I want it.

Sorry – I just could not help myself when crafting that title. I wonder if it’ll get good SEO juice. And yes – it was a really sunny day today in Boulder. By now everyone in the tech universe knows that Oracle has signed an agreement to acquire Sun. I – for one – did not see that coming. There has already been plenty of analysis on the good and the bad of it from a tech industry perspective. However, I haven’t seen much commentary on what it means for the Colorado tech community.

I had a phenomenal day. A few months ago my friend Bill Flagg recommended that I be a speaker at this year’s Gathering of Titans (GOT) event. This is an annual gathering of graduates of the Birthing of Giants (BOG) program. I participated in the first or second BOG event back in the early 1990’s and it was my introduction to the Young Entrepreneurs Organization (then about 100 members; now called EO and over 7,000 members around the world). BOG was a transformational experience for me – it was the first time as an entrepreneur that I really found my true peer group.