In my younger and more vulnerable years, I must have read The Great Gatsby a dozen times.  Maybe more.  And I loved and identified with the humble narrator, Nick Carraway.  His thousand mile journey to New Haven from Minnesota was much further than my hundred mile one from Brooklyn, but we shared the same occasional outsider's bewilderment at the antics of the eastern elite.

And yesterday, as I sat out on the deck of the Rosewood Sand Hill gazing up at the thin wafer of the moon rising out of the verdant hills and ascending the sanguine sky I wondered what Nick would've thought of this place.  Because sometimes I wonder if Silicon Valley is the modern version of Fitzgerald's Jazz Age playground.  Call it East Egg 2.0.  

But there are days on which it feels like there's a hush about the place; the raucous energy is muted and the punchbowls seem to have gone missing.  Sure, the future's still under construction here; the quiet is punctuated by the staccato tap-tap of programmers and designers working on the new new thing as cooling fans whir in the distance.  But there's a whiff of introspective stillness like that to be found on crisp autumn evenings after the grand shore places have closed for the season.

And maybe that stillness is the melancholy realization that the receding tide will beach some of the dinghies in the harbor.  Some even suggest that the venture business should shrink by half.  But which half?  There's a pandemic of bellyaching about "the venture asset class" among LPs, but I suspect that most investors will keep coming back . . . remember, most Americans hate Congress, but love their Congressman.  I think the venture business is the same way.  

But I'm always asking myself, "what do I need to believe to believe that a particular fund will be successful?"  There are a lot of good investors out there with compelling stories; in fact, there are probably more than I could invest in if I had three lifetimes.  But there's a whole other swath of the business for whom heroic leaps of faith are necessary; the arithmetic of their funds doesn't quite work, or they need too many outcomes to come out just-so, or the IPO market needs to be bubble-icious once more.  Like Jay Gatsby's, their reality is an idealized and stylized rendition of a sloppy present; it's not necessarily a false rendition . . .  just a hopeful one.  And it occurred to me as I pondered the imponderable future that the last few paragraphs of the book capture the challenge facing these funds, The Gatsby Funds, better than I ever could:

And as I sat there brooding on the old,
unknown world, I thought of Gatsby's wonder when he first picked out
the green light at the end of Daisy's dock. He had come a long way to
this blue lawn, and his dream must have seemed so close that he could
hardly fail to grasp it. He did not know that it was already behind
him, somewhere back in that vast obscurity beyond the city, where the
dark fields of the republic rolled on under the night.

Gatsby believed in the green light, the
orgastic future that year by year recedes before us. It eluded us then,
but that's no matter – tomorrow we will run faster, stretch out our
arms further . . . And one fine morning – 

So we beat on, boats against the current, borne back ceaselessly into the past.