This skillset just isn't that useful to a large software shop.
Startups are fun. I work at one now. 3/4 software engineering roles I have had have been startups. But all the work I am doing is also very shallow because everything is a fail fast timeboxed sort of thing where you work across a large spectrum of stuff and I will eventually need to change that.
You’re simultaneously doing some of the hardest work of your life but also watching some of your skills atrophy simply because you’re spread so thing across so many different problems.
Startup founders tend to make good product managers or cross-discipline engineering managers for this reason, but it can take some time to slide back into the groove of deep technical work in specific domains.
This doesn't really seem unfair as ORMs stop working at a certain level. He seemed to have been targeting companies doing more complex things than he was previously doing.