Last night I was speaking with a friend about a couple of issues he was experiencing both professionally and personally. We talked through several options, and near the end of it, I decided that the best thing to do was to talk in person.

So, this morning, I put Billie and Taylor into the car, packed a backpack full of water and poop bags, and headed up to Boulder. Three of us met at a trailhead, and we started the hike.

Initially, the thought was to hike for about an hour, we would all be able to vent to each other, offer support and suggestions, and at the conclusion, we would separate, one to go work, me to a hot yoga class, and the third went wee wee wee, all the way home. (Im making one of those up).

As we started hiking, dogs and all, we decided to take a path that we hadnt before. That path continued away from the trail head, and after about two hours ended at a sign that said, “Attention hikers! The trail dead ends here. The rest is private property. Proceed and die.” (I made one of those sentences up.)

Instead of turning around, already having decided to forgo our subsequent plans, we began to forge our own trail. We climbed over and down rocks, through cactus and brier, and after about another hour, finally reconnected with a lower trail. Each one of us sore, beat up, cut up, tired and thirsty, we began the trek back to the car, not realizing it was probably around a mile away (I am not making that up.)

We got back to the car, grabbed some food, and separated after four hours. What was originally planned to be a quick 1 hour hike (maybe a mile in total), became a 4 hour, 4.5 mile scurry and climb.

But, at the end, we all agreed it was a great day. And the conversation I have heard after the hike didnt include any of the lousy parts. In terms of transparency, we really werent transparent at all publicly. As far as most people know, the hike was great from beginning to end. There was little communication (and interest) about the entire trip.

Over the past two weekends, there have been three StartupWeekends. Toronto, NYC and Hamburg.

Toronto, based on Andrew Hyde’s comments and Brill’s comments, was not the most fun. During the weekend itself, there was little to no communication to the outside world. Other than a few blog posts at the end of the weekend, the only thing I could think about it, was that it generally sucked, and that it was not a positive experience for anyone.

Transparent, it was not.

NYC, on the other hand, seems to be going much more smoothly. Currently, there are 25 blog posts about the weekend activities. Toronto had 15 posts. Currently, there are 29 tweets from NYC, and there were 8 from SWTO.

There are multiple blogs following NYC, and the general feeling is one of abject postivitity. Andrew even posted a bunch of photos he took to his own Andrew Hyde blog.

But, where are the mistakes? Where are the errors? Where is the process?
NYC, Transparent you are not.

I understand that StartupWeekend is a work in progress, and I am a huge supporter of the concept and of Andrew himself. So much so, that I am going to travel to DC, on my dime, just to be around (I feel like its their weekend, and I can be called on for advice, but I really shouldnt have a material role in the weekend).

But, part of the beauty of this concept is transparency. The biggest disappointment for myself ,and many others at SW Boulder, was that while everything seemed to be great, we didnt launch. There was little indication–internally or externally–that was going to be the case. Sure, we made a major error, and to Andrew’s credit, he blogged about it. But the mix of disappointment and anger in the follow up posts is clearly there because the failure was a surprise.

At the end of the day, if StartupWeekend is going to be a success, and if its going to continue to be the global phenomenon it has become (There are cities in Europe signing up!) it has to bet its future on transparency. There has to be clear vision into the process itself, because the companies created during StartupWeekend dont matter–only the process does. Until everyone can see the process clearly and transparently, StartupWeekend will continue to be a nice experiment that a small number of people enjoy on select weekends, and like every other buzz-filled event, it will die.

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Last Sunday, I headed to the airport to fly down to Dallas for work. I did all my normal prep work. Downloaded the requisite songs and videos to my iPhone, made sure to pack my Bose headset, threw an extra charger in my suitcase, put my ipod nano in my shoes for working out, charged my Macbook, and, of course, packed some clothes.

Deciding that I really didnt want to sit with my two coworkers, I checked to see if there was room in first class (I have a billion miles on United, and a bunch of upgrade certificates). I was in luck, first class was open.

We get on the plane, and I settle into my seat. I put on my Bose headphones (I like to sit on the right side of the plane, because the power switch on the Bose is on the right ear, and therefore, the flight attendants cant see if its on or off), attached it to my iPhone (turning on airplane mode), and stuck the iPhone in my pocket.

I always put it on the side where the headphones would plug into the console, so the flight attendants dont ask me to turn off my music. I cant stand airplane music.

About 1 hour and 15 minutes into the flight, I feel for my iPhone wanting to check out an episode of Mad Men, and as I reach down, I can feel the iPhone slipping between the seat and the center console. “Dammit!” I muttered to myself.

As I tried to pull the iPhone out by the headphone connector, suddenly the music in my ear disappeared. I knew it would take just one slip of the fingers and my iPhone would be lost. Gently, I wrestled with the iPhone; slowly it made its way out of the crevice of the seat, and just as I was about to declare victory (in my best Johnnie Chase impression), the iPhone slipped out of my fingers and into the center console.

At the conclusion of the flight, I asked for help from the flight attendant. She tried to reach into the console and reclaim my phone, but only succeeded in knocking it down further. “No worries,” she said chipperly, “give me your card and I will mail it to you when we get it out.”

Being trusting, I gave her my card, and went on my way to the hotel. And, fully expecting to have my iPhone mailed to me back in Denver, with 15 minutes to spare, I found an AT&T store, and bought a new iPhone.

Resyncing it was a breeze. In fact, this phone has worked 100 times better than my old iPhone. No crashes, no freezes. Pretty excited about that.

After three days, I returned to Denver. Wednesday, I sit down in my office and there is a package, with no return address, waiting for me on my desk. “C’mon,” I thought, “this cant be my iPhone.”

Quickly ripping open the package, there was an iPhone sized item wrapped in a protective sheet and a rubber band. With glee, I opened it to find, the first iPhone Flip Phone!

Yes, I am well aware that it is not an iPhone or even an iPhone Flip Phone. But, what amazes me is that there are only two explanations why I got the above, instead of:

Evil Theory: Some United employee decided that they liked my non-flip version of the iPhone better than their iPhone Flip Phone and decided to send me the Samsung POS.

Less Evil Theory: United found multiple phones in the console of the first class seat I was sitting in, and sent back the first phone they found to me.

My plan is to call United tomorrow and see what happens. In the worst case, I will try and contact the person who’s phone I now possess and get it back to him or her. (If you lost a Helio Samsung Fin on a United Flight shoot me an email).

And so my vacation has come to end. I usually try and check out for a bit, but am never able to completely disconnect. I am too interested in what my friends are doing, and in a way, its a bit like being at your own funeral.

If you dont see a tweet, does that mean the person ceased to exist?

This vacation was an opportunity for me to really try and come to terms with the quality of my communication versus its shear volume. At what point does volume outstrip quality? Is taking a measured approach to communication better for all parties?

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