Only a few select lawyers get to argue before the Supreme Court. But even fewer are personally appointed by a Supreme Court Justice to do so. Deepak Gupta is one such attorney, and is no stranger to unusual or uncharted territory. Before launching his own firm in 2012, Deepak helped start the Consumer Financial Protection Bureau as senior counsel for litigation.

After discussing life as a Supreme Court advocate, Adam and Deepak descend into wonkery about regulation, the administrative state, and whether various agency structures might be considered constitutional. Sure, Adam once tried to sue the CFPB into oblivion — but what’s a little constitutional litigation among friends?