[Originally posted over at PEHub as the guest column on July 2, 2010]

So there I was, listening to the infectiously giddy (and, indeed,
bittersweet) Katy Perry tune “Waking Up In Vegas.” Now, I realize that
I’m probably more than twice the age of the typical Katy Perry
listener, but the ditty struck a chord. There’s a great moment about
halfway through the song in which Katy seems to be at the bottom of her
stack of chips, and she urges her gambling partner to “Send out an
S.O.S.” But, then, as she pauses to inhale, the momentary silence is
filled with an ethereal, angelic sigh, perhaps portending a change of
luck. With the wheel of fortune finally spinning her way, she changes
her tune and exhorts her sidekick with renewed optimism: “and get some
cash out!”

Maybe it was because I was driving back from an annual meeting
during which I’d heard some GPs describe a great year after a period of
difficulty, but the first time I heard the song on the radio I thought
it was a must-add to my mental soundtrack of the VC world. After all,
the way some people think about venture and its potential for
discontinuous outcomes (and punishing loss rates) makes it akin to
gambling; I’ve always thought of Curtis Sharp as the patron saint of
some venture investors, no?

Anyhow, as I thought about it a bit more, I re-envisioned the song
as a lament from entrepreneurs to venture capitalists who sit on their
Boards. Spoofing the song, I’ve replaced Vegas with Woodside, a tony
Silicon Valley hamlet that’s home to many VCs and entrepreneurs.
Keeping true to the original, there’s little rhyme and funky meter, but
here it is for your enjoyment:

Waking Up In Woodside

We’ve got a Board meeting
Last quarter’s all a blur
We need a term sheet ‘cause you’re under-reserved — and we’re broke

I lost my sales VP, but you lost a key LP
Spare me the lessons from G-S-B
or Mike Porter
You just want to sneak out and get to Tahoe

Don’t be a baby
Remember what you told me:
Sometimes the guys at TechCrunch can be such haters
That’s what you get for waking up in Woodside
We need some cash to get us out of beta
That’s what you get for waking up in Woodside

OK, we’ll cut our burn
Why do you act so stern, dressed up like Steve Jobs?
And why, why did you drop us from your firm’s website?
Call up your partners
‘Cause now we need a bridge loan

Don’t be a baby
Remember what you told me:
Sometimes the guys at TechCrunch can be such haters
That’s what you get for waking up in Woodside
We need some cash to get us out of beta
That’s what you get for waking up in Woodside

How do we all get out of this?
Capital efficiency, intellectual property
Send out a press release
And get a slot at DEMO
We’re gonna file an S-1!

Don’t be a baby
Remember what you told me:
Sometimes the guys at TechCrunch can be such haters
That’s what you get for waking up in Woodside
We need some cash to get us out of beta
That’s what you get for waking up in Woodside

We’ll make the quarter; make, make, make the quarter!
Let’s file for IPO, baby
Let’s get some cash out, baby