Some follow up questions came to my mind after listening to this. I am going to list them here. If you see this @craigcannon, please consider them for the next one.
1. One disadvantage of being young is that they are usually inexperienced in managing people and conducting business. How would you recommend young people to improve their skills in people management and business? What kind of books should they read? What kind of habits should they inculcate? Is there anything else you would recommend?
2. A non technical founder needs to be a product guy. It is also easy for a n00b to pick up coding skills as there are so many great resources on the internet, many of them operated by YC companies. The follow up question here is the converse: how can a technical founder learn product skills? What kind of resources are available and which ones would you recommend?
3. Sam mentioned AI and computer security as two areas that he thought was important. With AI, we are already seeing hints of disruptive technology (deep learning). What is the situation with computer security in comparison?
4. Stickiness of a new platform can be taken as an indicator of whether it is worthwhile to develop things on it. How would you rate voice platforms like Amazon Echo, Google Home, Apple Siri in terms of stickiness?