The dialogue in the movie is almost completely improvised, as it also is in Larry David's Curb Your Enthusiasm (2000) HBO series.
Likely inspired by Ronald Wayne, who co-founded Apple with Steve Jobs and Steve Wozniak, but sold his ten percent stake in the company after just twelve days for eight hundred dollars. Those shares would now be worth over thirty-five billion dollars.
In the same way that the protagonist's name "Rolly" sounds like "Larry" in reverse, the plot also takes of on a real-life angle from Larry David's life. In 2007, his wife Laurie Lennard filed for divorce, after it was revealed she had an affair with a young contractor working on the couple's estate in Martha's Vineyard, Massachusetts, the setting for this movie.
The three co-Writers Alec Berg, David Mandel, and Jeff Schaffer all wrote for Seinfeld (1989), then later co-directed EuroTrip (2004). They became infamous for the way they decided on who should get the solo directing credit on that movie, by drawing the name from a hat.
Other than the aerial shots, no part of this movie was filmed on Martha's Vineyard.
The artist of the Shopping Cart painting is named "Plepler", this may be after CEO and Chairman of HBO (who made the movie) Richard Plepler.