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: