Finding success as a stand-up comedian, he left his day job as a lawyer to pursue a full-time career in show business, in large part influenced by his older sister, Amy Poehler.
Hän menestyi stand up -komiikassa ja jätti päivätyönsä asianajajana pyrkiäkseen päätoimista uraa viihdealalla, suurelta osin isosiskonsa Amy Poehlerin vaikuttamana.