Fairly easy if your job description fits into one of the 13 designated jobs and you are from North America. Computer Systems Analyst and Graphic Designer are two that can work for startups - but whatever you do, do not include "programming" or "programmer" in your job description or tell the border agent you are a programmer. "Programming" or "programmer" is a huge red flag for the TN-1.

In fact, Microsoft brings on a lot of Canadian developers via TN Computer Systems Analyst and outright tells them to lie at the border and say they don't do any programming.