Quitting a safe job to join a start up. Anything I need to do or prepare for before I quit? And one insurance question as well.

I currently make almost 50k at my one job and 5k to 15k at my other jobs. My part time will increase to maybe 20k if my classes are approved (adjunct).

I'm planning on quitting my 50k job to join a start up and I am in charge of development. No pay for a while but the people are smart and well connected. I also trust them to have revenue by the end of next year. I live with my parents so no rent to worry about. It's a dead end career and mind numbingly boring so I'm quitting regardless for my mental health. I have the support of my parents because they believe in my potential which is nice.

I have 12k for emergencies. 600 a month for student loans.

My current checklist

1. Get a medical check up
2. Get insurance
3. Move pension to my part time job

My questions are, should I get medical through my part time job or covered California?

What else do I need to do to prepare for this jump?

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