The videos from my talk in Vancouver last week are up on the Bootup Labs Entrepreneurial Society web site.  They are embedded below – the first one talks about entrepreneurial communities and the second talks about the dynamics between VCs and entrepreneurs.  There’s also a throwaway line about my mom, a reference to the smell hanging over Boulder on 4/20, and the last vestiges of my voice before it departed me for a week.  Enjoy.

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.

Spend four minutes listening to Mark PIncus’s interview on Vatornews about his lessons from Tribe – fail fast.  Two great entrepreneurs that I’ve worked with before (and intend to work with again) sent it to me this morning with a note saying “wow – awesome – must watch.”  (n.b. each of them had one success and one failure before I funded their third company, which was a huge success.)

Mark is the CEO of Zynga (I’m on the board).  I love working with Mark – I’ve known him since the mid-1990’s and funds I’ve been affiliated with invested in his first two companies: Freeloader and SupportSoft.  Both were successes.  We didn’t (for a variety of reasons that I can’t remember) invest in Tribe which was a failure.  When Mark started talking about Zynga, it was an easy decision to jump on board and do the first round funding with Fred Wilson at Union Square Ventures.

Mark amazes me on a regular basis – not only has he synthesized everything he learned from Tribe, he has developed unbelievable sense of self-awareness as an entrepreneur and a human that helps accentuate the things he’s great at while opening up for help when he needs it.

Note to everyone: check your pedigrees at the door – tell me about your successes and failures when we meet for the first time.  And fail fast.

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.) 

If I’ve learned two things from Eric (and I’ve actually learned a lot more), the key to a great conference is (a) a superb list of presenters and (b) plenty of whitespace around them for everyone to talk.  You can see this in the Glue agenda which is pretty much locked down at this point. 

The presenters include Josh Ellman (Facebook), Aaron Fulkerson (Mindtouch), Andre Durand (Ping), Eric Marcoullier (Gnip), Peter Coffee (Salesforce.com), Tim Young (Socialcast), Mitch Kapor, Phil Wainewright, Kevin Matheny (Best Buy), Oren Michels (Mashery), Lew Moorman (Rackspace), Drummon Reed (InfoCard), and Bob Frankston.

Oh – and then there are all the folks on the panels: Steven Greenberg, Ben Metcalfe, Chris Saad, Stewart Alsop, Danny Kolke, Andrew Nash, Naveen Agarwal, Chris Shipley, Rick Nucci, Pam Dingle, George Reese, Jackson Miller, Sam Charrington, Jeff Fedor, Jeff Collins, Zoli Erdos, Peter Saint-Andre, Jack Moffitt, Seth Fitzsimmons, Jeff Nolan, Jud Valeski, Shane Pearson, Alex Iskold, Stu Charleton, Albert Wenger, T.A. McCann, Jeff Lawson, David Weekly, 
Jason Milgram, John Minnihan, Jim Reavis, Jeff Lindsay, Kevin Mullins, Kevin Marks, Mike Clymer, Randy Bias, Patrick Harding, Kyle Roche, Phil Windley, Todd Clayton, Angus Logan, Dave McClure, Andy Morgan, Jake Sorofman, and Celeste Merryman.

I hate trade shows.  But I love conferences.  When Eric and I first started talking about Defrag several years ago, I told him I wanted to get a bunch of super smart people together to talk about the Implicit Web, which was a theme we were starting to invest in.  Last year, my partner Seth Levine and Eric had a similar conversation around our Glue theme and Gluecon was the result.  I can’t wait to go hang out with the awesome people above and immerse myself in Glue for a few days.  Come join us.

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.

I was part of a group of about 30.  I knew nothing about broadband policy (which I later found out was in the extremely capable hands of Phil Weiser) so I focused my energy on the State of Colorado IT systems and on recommending a CIO.

Both turned out to be easy to deal with.  I was part of a task force that reviewed over 50 credible CIO applications, interviewed a dozen CIO candidates and had an easy choice in selecting Mike Locatis.  Mike had previously been the CIO of the City of Denver and had plenty of private sector experience; he stood out as a uniquely qualified candidate. 

Assessing the State of Colorado IT systems was equally straightforward – they were a disaster.  The entire IT organization was completely decentralized by agency.  Each agency had the equivalent of their own CIO that had purchasing authority up to $100,000.  The was minimal central planning and coordination, no purchasing leverage, and no integrated strategy across all the agencies.  I felt bad for the incumbent CIO – it was a classic case of all the downsides of decentralization with none of the benefits.  Oh – and this was written into the law so you couldn’t just reorganize the IT organization – the law actually had to be changed to centralize the State CIO’s authority.

We recommended the obvious – change the law to centralize everything under a single CIO.  Being government, this took a year, but it got done.  Then the real work began as Mike and his team went from talking about IT consolidation to actually doing it.

They’ve got a bunch of it under their belt and are now looking forward to the next wave of ideas around modernization of many of the IT systems and approaches.  Like most of the country, Colorado is working through their budget shortfalls to economic leverage on any level – including at the raw systems level – is a good thing.  Mike and his team recently put out Solicitation RFI-TK-003-09 which is an RFI for Transforming the State of Colorado’s Common/Shared IT Services.

As the cliche goes, you need to walk before you run; this RFI gives companies developing innovative Cloud Computing approaches (e.g. Google and Amazon) as well as numerous entrepreneurial companies an opportunity to get in front of Mike and his team to weigh in on the forward directions of the State of Colorado’s IT infrastructure.

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.

The 15 – 30 minute talk simply sets the stage for the Q&A.  Tonight’s Q&A went on for about 90 minutes and was fascinating.  We covered a wide range of topics, including a handful that hadn’t come up before and wouldn’t have occurred to me in a vacuum.  Part of the reason I do these types of things is very selfish – I’m always trying to learn and understand what is top of mind for entrepreneurs – and the questions bring that out.  It’s particularly interesting to me to listen for the nuances in the questions from people in different parts of the country.

I picked up a cold a few days ago and started feeling crummy around mid-day today.  The energy in the room tonight was a huge lift; even though my voice deteriorated rapidly and was basically gone by the end of the evening, I had a dynamite time with my new Vancouver friends.  Boris promised to put up links to the video along with a summary in a few days; in the mean time you’ll have to make do with the Bootlabs tweets and the event hashtag which, after some debate, settled on #blesfeld.

Time for bed.  At least I won’t be talking in my sleep tonight.

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.

In 20 years, I expect we will snicker at the idea of having to go search for information by typing a few words into a text box on the screen.  It’s way better than 20 years ago, but when you step back and think about it, it’s pretty lame.  I mean, I’ve got this incredible computer on my desk, a gazillion servers in the cloud, this awesome social network, yet I find myself typing the same stuff into little boxes over and over again.  Ok – it’s all pretty incredible given that it wasn’t so long ago that people had to rub sticks together to get fire, but can’t it be amazing and lame at the same time?

Several companies that I’ve got a personal investment in that play in and around the implicit web recently came out with new releases that I’m pretty excited about; each addresses different problems, but does it in elegant and clever ways.

The first – OneRiot – came out with a new twist on using Twitter for search.  OneRiot’s goal is to provide a search engine for the real time web.  To that end, they’ve historically gotten their data on what people are looking at from a collection of browser-based sensors (anonymous, opt-in only).  They’ve built a unique search infrastructure that takes a variety of factors, including number of people on a specific URL in a particular time period, freshness of the content, and typical content weighting algorithms.  A little while ago they realized that people were tweeting a huge number of URLs, mostly via URL shorteners (which are loathed by some very smart people.) Twitter search addresses keywords in the tweet, but it doesn’t do anything with the URL’s, especially the shortened ones.  So, OneRiot built a pre-processor that grabs tweets from Twitter’s API that include a URL, tosses the shortened URL into OneRiot’s search corpus (which expands the URL and indexes the full page text), and then references it back to the original tweet.  It also correlates all tweets with the same URL (including re-tweets) across any URL shortened service.  Now, imagine incorporating any URL data that’s real time that has an API, such as Digg.  Aha!  It’s alpha so forgive it if it breaks – but give it a try.

The second – AdaptiveBlue – has released their newest version of Glue.  Glue is a contextual network that uses semantic technology to automatically connect people around everyday things such as books, music, movies, stars, artists, stocks, wine, and restaurants.  It uses a browser-based plugin to build this contextual network implicitly.  When you are on a site such as Amazon, Last.fm, Netflix, Yahoo! Finance, Wine.com, or Citysearch, the Glue bar automatically appears when it recognizes an appropriate object, categorizes it, and let’s you take specific action on it if you want.  Glue has been evolving nicely and now includes the idea of connected conversations between friends (e.g. talk about whatever you like regardless of the site you are visiting), smart recommendations (e.g. implicit recommendations), and web wide top lists of the aggregated activity of all Glue users.

In addition, we’ve finally found a company that we think is attacking a wide swath of the problem of the Implicit Web the correct way, at least given today’s technology. We hope to close the investment and start talking publicly about it early next month. 

For now, I expect the applications around the Implicit Web to continue to fall into the early adopter / you need to see it to believe it category (where it’s harder to explain than just to show).  In the near term, if you are interested in this are, try out OneRiot and Glue – they are both evolving and maturing very nicely.

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.

If you live outside Colorado, your first reaction is probably “who cares.”  However, did you know that both companies have their second largest US operations in Colorado?  Nope, that hadn’t occurred to me either until I met with senior execs at both companies two weeks ago with Colorado Governor Bill Ritter.  Think about it – two native Silicon Valley companies have their largest US operation in Colorado. 

During my two day trip to Silicon Valley with Governor Ritter, Don Elliman (head of the Colorado office of economic development), and Mike Locatis (Colorado CIO), we had about a dozen meetings.  The Sun and Oracle meetings were uniquely interesting because of the large presence each company has in Colorado.  Sun’s comes from a combination of organic growth and their acquisition of StorageTek; Oracle’s comes from organic growth and their acquisitions of PeopleSoft (which had previously acquired JD Edwards), BEA (which had a good sized operation in Boulder that resulted from two other acquisitions), and Hyperion (which had previously acquired Decisioneering).  I don’t have the exact number of total employees of both companies in Colorado but I’m guessing it’s around 10,000 with a heavy concentration of them near Boulder, Denver, and Colorado Springs.

In both the Oracle and Sun meetings, the executives that we met with were extremely enthusiastic about their teams in Colorado.  Even if you discount their enthusiasm based on the fact they were talking to the governor of Colorado, it was sincere and substantiated by their perspectives on the capability, quality, and loyalty of their Colorado-based workforces.  It was clear that regardless of future acquisition activity, both companies had plans to continue to grow their bases in Colorado.

Now, acquisitions are always complex and this one isn’t expected to close until sometime this summer.  However, given the existing presence of both companies in Colorado, I expect there will be additional focus on the appropriate integration dynamics.  While they will likely include some rationalization of people and facilities, I expect it will be healthy for the long term growth of Colorado as a technology center, especially given the positive experiences each company has had with large workforces in Colorado.