I agree. If I founded a YC Company, or any other startup, I'd look at Omnisio's story and think about duplicating it. Clearly Chris Sacca was an important part of that acquisition. I think it's a very smart move to get him to invest.
It's just so incredibly important to take money from people are in the position to help you reach liquidation (if that is what you want). I know that sounds really obvious, but I'm sure some founders struggle with the decision to take money from the first person who offers, no matter how un-connected they are.
I'm not saying I don't envy Omnisio's trajectory, but YC (and any other investor) has a vested interest in investing in companies that DON'T follow this path. They want empire builders, not build-to-flip folks. Not that Omnisio built with that in mind-- I heard them talking about a lot of long-term stuff, so I'm pretty sure they were building for the long term and just got a great early offer.
"It's just so incredibly important to take money from people are in the position to help you reach liquidation (if that is what you want)."
I've heard many times that companies get bought-- they don't get sold. In practice, I think having experienced folks in your corner helps (especially with setting price and terms)... But not nearly as much as having a company worth buying.
how many hours did it take him to close the deal? (jk)
And I agree with dustineichler, I haven't used RescueTime long, but it is already helping.