Rules, guidelines, regulations, and “laws” are all sometimes used interchangeably — but what’s legal and what isn’t is far more complex when it comes to policy, especially when politics (and technology) enters the picture. Take encryption for instance: The debate has gone beyond the “Crypto Wars” of yore to a war of attrition playing out today as companies (like Apple) go head-to-head against law enforcement (FBI); but who wins and who loses if the battles play out differently in litigation vs. legislation? And what of cybersecurity more broadly, Russia and hacking, and other top-of-mind policy and politics topics, such as immigration? What are the legal and technical (not to mention moral) nuances of military drones … including the possibility of automating even government decision making in the future?

All of these issues share in common the power of technology to both “discriminate” — such as between military targets and civilians — as well as scale beyond borders. Technology doesn’t just level asymmetries; “It levels all asymmetries,” observes Benjamin Wittes, Senior Fellow in Governance Studies at the Brookings Institution, and editor-in-chief of the (now) popular Lawfare blog that focuses on “hard national security issues”. In this episode of the a16z Podcast recorded while on the road in D.C., we (with Sonal Chokshi and Hanne Tidnam) take a quick tour through those issues — as well as the meta story of Lawfare as a story about the evolution of media and expert blogging on the internet.