Before co-founding Flatiron, Zach was Co-Founder, President & COO of Invite Media, an advertising technology company based in NYC. Invite Media built the industry's first enterprise advertising platform for buying and optimizing online media in real-time. Invite Media was acquired by Google in 2010.
Entrepreneur -> Angel Investor
For seed / early A's, ability to stretch up and down. Up to markets / competitors / sales strategy / pricing etc. Down to product features, technical stack, understanding software tradeoffs. Ideally founder can do both in the same person. Assuming that baseline is true, then look at market size, ability to be a monopoly etc. Criteria changes to be much more data driven later stage.
Hand them my cell phone and let them text/call me literally anytime. Reply ASAP, ideally within 2 hours.
Know the details.
NYC founders tend not to think that tech is the answer to the world's problems. Much more practical.