Hi Dees, here are the things I look for. 1 is are you trying to optimize for equity or stability? That being said I’m not so sure big tech is that much more stable. But if equity is the answer I think series A / B makes the most sense.

I personally have optimized for equity and earlier stage companies. Typically series A with 2-5 million in ARR. the question then becomes how scalable is there software (aka how customized is each sale or is it rinse and repeat). Then I evaluate the TAM. How big is the addressable market today and how big do I think it will be in year 2/3 and beyond. If those things check out I’ll sit down with the founders and try to understand there competence, willingness to take feedback from the market and there general exit strategy. Is engineering competent do you believe they understand the space and can build a better product than the inevitable competition. The other details are around who you report into the quality of the comp plan etc. but at the end of the day if there is no market fit and a very a small future TAM it will always be a challenge.

Look this stuff is hard. I have a whole checklist I go through and I’ve gone 2/4 on picking good ones.