Today, I was really fortunate to go to the Big Omaha conference that was put on by Silicon Prairie News. As soon as I heard about it, I started lobbying my manager to send me, so I could listen to the likes of Jason Fried from 37signals, Matt Mullenweg from Automattic (the creators of WordPress), Jeffrey Kalmikoff of Threadless and the king of internet wine shows, Gary Vaynerchuk.

It was a terrific day as Jason Fried kicked us off and talked about what became a common theme for the day, failure. While there were others who thought that failure was a good thing, Fried felt similarly to the way I did:

When did “fail early and often” become cool? - Jason Fried

What followed after Fried was a Yahoo guy a presentation about Girls in Tech and Micah Baldwin, who talked at length about failure. We headed over to lunch across the street where Ramsey, Whitney and I spent time talking with the very visionary web team at the University of Nebraska, who are really doing some interesting things with their web initiatives.

After lunch is when Big Omaha really came alive. Unfortunately, Matt Mullenweg was not able to make it because of a conflict, but we were very fortunate to have a lively panel with Fried, Vaynerchuk, Baldwin and Kalmikoff. It was all Q&A based and was a lot of fun to see these thought-leaders and visionaries on the web talking and bantering back and forth. Of particular note was their rant on the higher education system, which is a little too colorful for this blog.

That was followed up with one of the most insightful and thoughtful talks of the day by Kalmikoff, where he talked about transparency and accessibility and what they mean to Threadless as a company and as a community. His slides included a great large/medium/small fanged Pac-Man illustration as well as great insight like:

“Spend time with your community.” and “Listen. Review. Respond. Act.“

I got the opportunity to spend some time talking to Kalmikoff after the talk and I really found him to be approachable and friendly as I asked him such lame questions as “How do you apply your community models to a B2B environment?”

Kalmikoff was followed by Ben Rattray of Change.org who gave a well-polished (albeit a little forgettable) presentation. I couldn’t help but think that Rattray was actually Chris Pine from the new Star Trek movie (mixed with a little Jake Gyllenhaal). You decide:

There was a local entrepreneurial panel that highlighted some of the really cool projects that are going on in Omaha, including the concert hall/non-profit 2-screen theater that they’ve got, which is very cool.

The day was closed out with a great keynote (so to speak) with Gary Vaynerchuk. Now, say what you will about Gary, you can’t ever say he’s not genuine. The guy knows who he is, knows what he loves, and isn’t afraid to tell you what’s what. Instead of doing his typical talk, he realized that much of the crowd had heard him speak before, so after a short 7-minutes, he went into an open Q&A session.

I decided that I should take a crack at asking a question. Much of what I found to be challenging about ideas presented at Big Omaha was that much of it is extremely difficult, if not impossible, to apply to the corporate B2B world. That’s not to say it can’t be done, but I have a hard time taking Gary’s advice of “you can’t change them, just quit”, very lightly because I was unemployed for 3 months.

But getting to interact with Gary during the Q&A session (as well as briefly after it was over) was a lot of fun. Plus, I even got a Thunder Show wrist band!

Big Omaha was an extremely well-organized conference for its initial outing. Even down to the smallest of details. The folks at BrightMix put together a heckuva day that made the 3-hour northward trek completely worth the price of admission (a steal at $200). Many thanks to Jeff and Dusty (and all their great volunteers) for working so hard to hold such a great event. You can find my pics (and others, tagged with ‘BigOmaha’) on Flickr.