This looks awesome! Playing it now. It's a really good idea.
Edit: I looked at a few pitches, I thought they were very realistic. For the Pointer acquisition it only listed the requested round size, not the valuation, which I think is really important for investors. It didn't completely make sense to me why they would need an investment for an acquisition, but when a company gets an acquisition offer is a pretty good time to raise money.
Feedback: I'd recommend using a different branding rather than Y, since YCombinator invests at the seed stage using standard terms, and doesn't make follow-on investments as far as I know. (I could be wrong.) It's better if you make it a hypothetical VC rather than use YC's branding.
Game was very fun, thanks for making it.