> May 2022 - Left my SWE job at Wave and incorporated my own startup called Path (a Delaware C corp) I was permitted to remain in the USA, since I was not employed by Path yet. My understanding is that it is permissible to do exploratory work on a new startup as long as you are not employed by that startup, and your previous visa has not expired. It was during this time that my cofounder and I raised money for Path. Note: If I had left the USA during this time, I would not have been permitted to re-enter on my old L1-B visa.

This sounds iffy. I'm in the US on a L1-B visa as well, and my company went through rounds of layoffs, which concerned me. All information I've read, including the immigration team from my company (Big Tech), points out that if I lost my job, I would have had a short time to leave the country with no chance to find other jobs.

Unless I'm reading too much into it, it sounds like OP spent some time in the US in an illegal status, until that gap was bridged with the new visa.