Ask HN: I'm 30, how to break in Product roles at tech company/startup?

I thought my entrepreneurial spirit and experiences trying to start businesses/build products, helping out at a University "startup course" (much imposter syndrome, yes) and my past in Project Management were gonna be enough to get a shot at a startup but I've been getting rejection after rejection.

Quick recap of my CV

- 3 years PM in Advertising. Strategy and management of the creative team

- 2 years working as Customer Support drone in Big Boring Company with very little room to move and change departments

- 1 year or so helping out at university Venture Lab where we do workshops and Pitch simulations for entrepreneurs and students (about 50-50).

- I did 2-3 projects that never took off and one app that gave me some satisfaction (someone bought it) but never even broke even. In that case I acted as a Product Manager and had 1 developer doing the work for me.

- I did CS50 from Harvard online and a Python course with MIT both on EDx, but I am not able to apply for a programmer job (which I think I would enjoy and might be a way to eventually turn into a technical PM)

I'm playing around with selenium and chromedriver building a bot that swipes on tinder based on certain parameters, but I don't feel like I could be considered for a programming job.