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This is all excellent advice! The one about the startup that struck a deal early and then was hamstrung in pursuing its business is, sadly, a classic.
The advice is sound but the analogy is ridiculous.
The analogy strains at times, but I don't find it completely ridiculous. In the world of sales and BD, "whale" is a common name for a very big account or target. Oftentimes this means a big company.
I think what the parent meant was that "Moby Dick" as a metaphor for "something alien and unknowable whose behavior you can't predict or understand" is not how it's usually used, which can be confusing. Usually when Moby Dick is used allegorically, it means "something very rare", or it's a metaphor about being consumed by the pointless desire for vengeance. Neither of those are the way the author used it here.

(More abstractly, if X is usually used in literature as a metaphor for Y, but you use it as a metaphor for Z, and Z and Y are unrelated, readers will sometimes find it hard to follow.)

A closer metaphor might've been Solaris, or some kind of Lovecraftian monster, but that reference may have eluded readers. Oh well.

Gotcha.

I've usually heard Moby Dick referenced to mean something elusive or borderline impossible to catch -- which is not necessarily the same thing as rarity, but has a similar outcome I suppose.

Of course, as you point out, the ultimate point of most Moby Dick metaphors is caution: chasing the white whale leads to your doom.

That latter point, even though it isn't the thrust of Andreesen's metaphor, nevertheless comes through in the article. So the whole "Moby Dick = unpredictable" thing doesn't quite hit its mark, but "Chasing Moby Dick = fruitless and possibly self-destructive" still does.

I'd love to see someone reference Solaris in a post like this, but yeah, it's just too obscure for most audiences.

I definitely had trouble taking the analogy serious, maybe it wasn't meant to be serious.
> Fourth, beware bad deals.

> I am thinking of one high-profile Internet startup in San Francisco right now

which specific startup is being referred to in this section of the article?

This was from @pmarca's old blog, so I am not sure the date on the post is correct.

No idea.

Just shut down a company because we fell into some of these pitfalls. Such a great article to remember next time.