The company has run into obstacles at every step of the way--partners who failed to give necessary support or who even turned hostile, and competition from a multitude of corporate Goliaths (including Bill Gates, who declared that he could either buy AOL or bury it). Worst of all, AOL has created a cascading sequence of operational and technical blunders, often offending or infuriating the people they most need to survive; yet the company still manages to dominate the online service industry.

Swisher speculates that one main factor enabled AOL to succeed against overwhelming odds: the superior vision of marketing executive Steve Case. While other online services focused on games, shopping, and business, AOL worked on building community and interpersonal contacts. This service proved valuable enough to outweigh the company's mistakes and misfortunes.

However, it is this same focus that has also brought on many of AOL's problems. Swisher describes AOL's struggles with the seamier side of online life--people who use the service for criminal activities and for discussing raunchy sexual issues. Swisher also discusses the problems that come with too much success, such as the overload of users that routinely slows down or completely crashes the system, the backlash on the Internet when masses of netiquette-challenged AOLers appeared in cliquish newsgroups, and the national outrage when a technical problem brought down the entire service for many hours.