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Founder stock agreement boilerplates restrict founders from encumbering or pledging their shares without the approval of the board.

I have heard of loans either secured by or "based on" shares of privately-held startups. I have no idea how common this is -- probably pretty uncommon.

See e.g. https://www.svb.com/private-bank/founder-liquidity/ and http://www.founderscircle.com/services/

I would be interested to know (1) what the legal and regulatory implications of such a deal would be, and (2) what the implications would be with respect to the deals the founder would have signed with regard to the equity they were holding.

My suspicion is this couldn't be done without causing problems in one or both domains, but I don't base that on anything solid.