As others have mentioned, avoid startups, unless they are one of those unicorns. You have moved to product and project management. You know, every guy wants to transition from programming/coding/engineering (all those individual contributors roles). Where have they moved to: product management (if they got MBA from any school), project management (with PMP and CSM certified scum master). Some have moved to engineering leadership. Once you transition to these roles, you can't jump out the way a programmer can: you need to find another full time at an established company.

In many companies in the states I have worked as a consultant, product and project managers don't have direct reports. If I were you, I avoid becoming a project manager (PMP, SCM) like a plague, unless you see lots of upside financially in the short turn.

Even for a job as a product manager in the states, you will have hard time getting offers/interviews form established companies: these companies have lots of qualified local candidates for product manager roles.

If you were a graduate of an elite school, try your connections, thats the way to get your foot in the door.

I have avoided becoming a project manager: every mid-career guy without hands on is a project manager these days. Some have become consulting architects for VMware, Cisco, if they can talk tech. Others have got evening MBA from Columbia-Haas etc: even here, all these guys are planning to become C-level execs. But what I see now in the valley: Columbia-Haas MBA does not cut, except to become a senior product manager. Thats the case with Kellog, Chicago Booth, etc; I had seen a kellog MBA with prior experience as a product manager, working as a contractor for a startup.

Are you trapped? I don't know. What I can say is this: you have too competition to get a product manager role at top tier companies.