The cypherpunk dream wasn't just permissionless finance—it was freedom to conduct peer-to-peer commerce without gatekeepers. Silk Road offered the first glimpse of this world before its collapse shut down that vision along with the marketplace. Meanwhile, Web2 platforms built trillion-dollar empires by intermediating commerce, extracting 20-30% while controlling who can participate. My research fellowship at the Ethereum Foundation examines why blockchain has revolutionized finance but failed to disrupt commerce. I'll present how recent advances in programmable cryptography, attestation frameworks, and AI agents now make it possible to realize the original cypherpunk vision of trustless commerce—not just for contraband, but for the trillion-dollar markets of goods and services that power our economy.