Donald Trump has proposed a $1 trillion spending plan to rebuild America's infrastucture. But for what ends? Better roads? More people working? Evan and special guest host Daniel Roth debate the right and wrong ways to spend $1 trillion and the problems that can't be solved with asphalt and nostalgia.

Speaking of building and rebuilding! If you were alive during the original dotcom boom, you knew Webvan, the company that sought to deliver just about everything to anyone anywhere. This was Amazon before Amazon was Amazon and Coppy Holzman was the co-founder of the one-time $9 billion (!) in market cap company. Then, as quickly as it expanded, Webvan went bust in the dotcom crash. Coppy has since gone on to build and sell charity-experience company CharityBuzz and is now creating a dog-friendly coffee chain called Boris and Horton. He talks about how his vision of what it takes to build a sustainable business has changed over the years and what matters most.