“It’s the weirdest thing,” confided an entrepreneur to me the other day.  “Talk about role reversal:  when I was raising my series A, the VCs were so negative and pessimistic that I had to exert every ounce of optimism in me to overcome their objections and convince them to invest.  But now that we closed the round, successfully launched the company and they’re on the inside sitting on my board, they are the over-the-top optimists and I find myself, as the one slogging through the hard details of building the business, I am suddenly the pessimist!”

It is an odd phenomenon I have observed.  VCs love to shoot holes in other people’s projects and plans, particularly during the due diligence phase of evaluating a project where the exercise is to identify all the major risks and scrutinize every one of the entrepreneur’s lofty claims, finding all the points of weakness and using them as rationale to either walk away or beat down price in the deal negotiations.

But once a VC has invested in a company, they suddenly go native.  When speaking about one of their own “babies”, they can often be the biggest promoters on the planet.  At times, they are even more over the top than their entrepreneurs. How many press release or article quotes in financings contain the effusive “this could be a billion dollar company” description from the lead VC?  Or how brilliant the entrepreneur is that they’ve just backed?

You will never hear them confide in a cocktail party conversation that, "this company is a dog"?  Or hear them describe one of their entrepreneurs as simply weak?  Instead, ask any VC how they’re portfolio is doing and you’ll likely get the common refrain:  “Somewhere between strong and very strong”.  They are either being promotional, or they really believe it.  After all, everything looks better from 30,000 feet.

On the other side of the table, the entrepreneur who is slogging through the start-up muck sees all the warts. During the fundraising process, they spend hours upon hours covering up these blemishes. But once the VC is in the tent and on the other side of the table, the entrepreneur exposes everything.  And then the tension can begin, because the entrepreneur is the one on the hot seat dealing with all the problems – sweating out each quarter, each product release, each competitive move.  They can often get frustrated when the VC glosses over the issues and dismisses them with a glib comment at the end of a board meeting – and see you next quarter.  And so, their positions switch – the VC morphs into the optimist and the entrepreneur morphs into the pessimist.  So next time your local VC is raving about their latest portfolio company, before you jump to any conclusions, remind yourself to check in with the entrepreneur – you may get a very different picture.

I’m pleased to provide a “shout out” for my partner, David Aronoff, and his new blog GeekVC  David is far funnier, more colorful and creative than I am, as his blog attests, and I’m thrilled he’s decided to step up and join me in the blogosphere!  My other partner, Chip Hazard, provided a guest blog a while ago on his views on the Enterprise IT market (with a nod to Spam-a-lot, we refer to it as the “Not Dead Yet” investment philosophy).  Now my 4^th partner, Michael Greeley, is the sole “blog virgin” in the partnership.  We’ll see how long that lasts…

We picked blueberries last weekend with our kids.  They are in season here in New England and yielded a great crop this year.  Afterwards, I read to them the classic children’s book, “Blueberries for Sal”, a charming story of a little girl who follows her mother around a blueberry patch, eating berries as fast as she gathers them.  When they drop into her empty pail, you can hear the refrain “kerplink, kerplank, kerplunk”.

As I intoned these sounds, I thought about a VC spin on the story.  What if VCs walked into Monday morning pitches with entrepreneurs and each partner dropped their beloved Blackberries into a pail?  "Kerplink, kerplank, kerplunk".

The Monday Morning Partners Meeting is every entrepreneur’s dream and nightmare rolled into one.  It’s their big chance to present to the entire partnership – a sign that their deal is being taken seriously and that the lead partner is comfortable exposing it to their colleagues.  On the other hand, it’s a forum rife with pitfalls and potholes – either everyone is bored, distracted and checking their Blackberries every few minutes, or they’re peppering you with tough, pointed questions and frowning cycnically.   When my business partner and I pitched the Kleiner Perkins partnership on the Upromise Series A, I still remember how John Doerr drilled into the deep specifics of a slide with a number on it just to see if we truly knew our stuff, caring less about the answer and more how we responded under fire.  In many other pitch meetings, I’ve felt like I was talking to a log as the VC would furrow their brow, nod their head and pretend to listen, while staring down at their rapidly twitching thumbs.

For some VCs, having Attention Deficit Disorder seems to be a competitive advantage and the ever-present Blackberry on the hip is like a narcotic – we always check it to see what new deal might be coming over the transom, how the latest portfolio company did in the quarter and the final score of the Red Sox day game.  But what if VCs literally dropped their Blackberries into a pail when meeting with entrepreneurs and actually focused on the meeting?  I know many an entrepreneur who would breath a sigh of relief if they heard "kerplink, kerplank, kerplunk" as they walked into the Monday Morning Partners Meeting.  It would show great respect for the entrepreneur, a signal that their project is the most important thing right now and deserving of full, high quality attention.

So the next time you’re entering into the dreaded Monday Morning Partners Meeting, bring your pail and collect some Blackberries.  If you have the courage to do that, you might get that coveted term sheet after all.