Foursquare Founder's Pivotal Moment

It looks more and more like Yahoo is offering big money for Foursquare—and like Foursquare creator Dennis Crowley is taking his time deciding whether to accept. It can't help that's he's lost one potential advisor, his longtime girlfriend.

Rumors that Yahoo would pay in the neighborhood of $100 million for the mobile-phone "check in" service first surfaced nearly two weeks ago on Business Insider. They've since been reinforced by TechCrunch's reporting, and Crowley hardly batted them down in an interview with our own Doree Shafrir for New York:

When I ask Crowley about the Yahoo-acquisition rumors, he doesn't deny, them, exactly. "We're trying to figure out what the best thing is for us going forward," he says. "We're raising financing and meeting with tons of different companies. Don't read into it too much... We could make it work as a stand-alone business, or it might turn out that there are other companies that would find us valuable. The future is rosy."

The future might be rosy, but the present isn't entirely peachy; we've heard from multiple sources that Crowley has split with fashion-industry girlfriend Chelsa Skees (with Crowley in the picture up top, from his Flickr stream). It wouldn't be the first time the stresses of running a startup undermined Crowley's relationships. Apparently Crowley and Skees last split just a few weeks before the launch of Foursquare at South by Southwest.

Chalk it up as another brutal lesson of entrepreneurship: The moment you're drowning in unsolicited advice tends to come when you're least able to give proper attention to the associates you trust most to sort through said advice.