Every day I get emails from entrepreneurs that make me think.  In this case, it’s from a friend who is on the fundraising trail.  He started off the email with “I felt compelled to share this with you as someone who would appreciate it.”  I thought it was dynamite and asked him if I could share it since – in its unedited form – it captured so nicely what I expect many entrepreneurs feel. And, just as importantly, it’s something I hope VC’s realize that entrepreneurs – even very experienced ones – feel.

I am fortunate to have successfully raised venture capital from top tier investors before. 

I have been a failed and successful CEO and know the difference.

I have earned my CEO stripes by being a successful operator in startups and big organizations.

I can lead, problem solve and think strategically.  I am technically adept, I can sell.  I work hard.

Yet, as I set out to raise money, I still have a great feeling of unease of the result.  I guess I have humility as well.

I’ve noticed, or maybe more accurately, I’ve become aware of the ether that is between a venture investor and entrepreneur.  In the ether, all things that can make or break a deal exist: idea, market risk, technical risk, team competence, economy, deal flow, competition, VC mood that day, entrepreneur pitch that day, first impression, gut feel, blog post for or against the idea read that morning, breakfast/no-breakfast, bias for or against, smarts or not-so-smarts of the VC and entrepreneur.

In my pitch experience, VCs I have been convinced hated me and my company after my pitch have invested.  VCs I am sure as shit loved me and my company after my pitch blew me off.  I have also been right that VCs I thought hated me and my company told me they in fact did; and, those who loved me and my company did in fact invest.  It’s been a crap shoot at best. 

Assuming there is something of merit in the idea, market, team and company, somewhere in the ether is a term sheet and a kick to the curb.  Coalescing just the right combination of elements in the ether at the right time has proven to be more art than science.  Anti-portfolios highlight how successful companies didn’t get it coalesced with one investor but did with another.

If I get it right and a financing comes together for my new company, I hope to have learned something that tips the scales of randomness in the scrum.

At dinner tonight we started telling miserable airplane travel stories.  Everyone has a least one (or 7,321) so it’s fun to hear some of the really abysmal ones, especially the night before I head to the airport to catch an early morning flight.

We were also talking about various philosophies of life and how to deal with difficult stuff.  After a while the conversation circled back to air travel.  And then I heard the best line of the night.

“When I travel I pretend I’m luggage.  From the moment I set foot in the airport, my expectation is that I’ll be treated no better than my luggage gets treated.  As a result, my expectations are so low that any little bit of happiness and politeness brings me great pleasure.”

I laughed out loud.  It was said with a sardonic grin, so the backdrop was framed appropriately.  There was a quiet pause after my laughter.  And then I pondered it – and thought how incredibly right this approach was.

Rather than bitch endlessly about the misery of our air travel experiences, let’s all spend November pretending we are luggage.  The only goal of the plane is to get us from point A to point B.  I guess there are circumstances where this won’t happen, but in most cases we’ll eventually get there.  Time doesn’t really matter to a piece of luggage, nor does comfort.  Politeness?  I’ve shoved many a piece of luggage into a space that it didn’t fit without even saying “excuse me.”  Oh – and I’ve put my smelly feet on my luggage many, many times.

In addition to pretending I’m luggage, I’m also going to make sure I use my super power on every plane flight this month. Luggage is very good at sleeping on planes, as am I.  Luggage sleepers unite.

See you at the airport.

We’ve been investors in Oblong since 2007 and I’ve talked about them regularly on this blog including a post titled I’ve Seen The Future from my first meeting with them.  I’ve known two of the founders – John Underkoffler and Kevin Parent – since we lived together at MIT (we all lived in a fraternity called ADP on Mass Ave. at the same time, along with a bunch of other entrepreneurs including Colin Angle – the founder of iRobot and Jeet Singh / Joe Chung – the founders of ATG.)

A few months ago my partner Jason Mendelson was introduced to a reporter from Bloomberg who was looking for “innovative companies to interview” for an upcoming Bloomberg TV series called Bloomberg Innovators.  Jason immediately thought of Oblong and made the introduction. 

Bloomberg Innovators has four thirty minute episodes – the first one titled Turning Point is about Oblong.  In addition to highlighting the amazing stuff the gang at Oblong is doing, the show takes you through the history of how the innovation that is called Oblong’s g-speak Spatial Operating Environment was created.  As part of this, you get to see some pictures of John Underkoffler 20+ years ago in the Media Lab working on the Luminous Room along with some background on John’s work on the movie Minority Report.

If you are interested in how innovations evolve, the future of human computer interaction, Oblong, how some VCs think about investing in the future, or just want to have your mind blown with some amazing stuff, spend 30 minutes enjoying the show.

Bloomberg TV doesn’t allow embeds, so you’ll have to launch Bloomberg Innovators: Turning Point from here.