In the meantime, Troy sent over a Letter of Intent and explained that it needed to be signed and returned by Monday. I was very frustrated by this. You don’t send a legal document to someone over the weekend when their is no time for a lawyer to review it and demand it back by that same Monday. Whether it was the intention or not, this was a high pressure sales technique and just one more red flag.
Which is well put- "whether it was the intention or not." So, why wasn't Talkroute simply rejected for taking too long? If Techstars was concerned about an undersized cohort, they could simply sign another startup with no ill will - Talkroute just missed the deadline. No harm no foul.
A Saturday -> Monday LOI signing isn't typically considered a reasonable expectation.