On life as an angel, failure and success, humility, portfolio construction, what we can know

East Coast vs West Coast 

Differentiation in a world of cheap capital

What a restructuring background can teach you and why he didn’t pursue private equity

This moment in technological and political history

What he’s reading

Whether you should become a VC today

Why he teaches

“The biggest mistake most new angels make is they invest in things where they know it’s going to succeed”