"Maybe it's better/a good time you leave" as part of a conversation is one such way to recommend someone leave rather than a likely alternative.

I don’t understand. Do you care to explain?

That kind of phrasing often carries an undertone of "and if you don't leave voluntarily, we will fire you".

I understand that. Thanks.

I just don’t know how this relates to what I wrote.

Basically it could be that he's not "lying" by speaking a half-truth, e.g. if he didn't resign then the writing was on the wall that he would have otherwise been fired.

Understood thanks.

I meant something different though: I was thinking if he might remember it differently today than if actually happened.

Human memories are not very reliable.

Some people's memories aren't very reliable, people who develop lying as a habit, who weave webs of lies - "the lies we weave when we learn to deceive" - are especially not going to be reliable with their recall; and you can get signs of this based on how they respond or react to questions or engagement.

A talk with YC head like Paul or other, a "read the room" situation, the writing is on the wall, etc.