A few years back, Sheryl Sandberg--COO of Facebook--started a wide cultural conversation with her book Lean In. She talked about how few women led large companies--or countries--how most women were judged differently than men in their companies, and how the prospect of having children was a constant talking point and question for women. Tom and Dave are joined by Trudy Choi, a lawyer and creator of a Hot List newsletter for millennials, and Emily Reynolds, a product manager in the travel industry, to talk about what this looks like for them and many of their friends.