Robertson faced numerous lawsuits from major record labels due to copyright infringements from the company's "Beam-it" and "Instant Listening" programs.

Robertson founded OS technology company Lindows, which later changed its name to Linspire after settling a trademark lawsuit with Microsoft.

Despite the early success of MP3.com on Wall Street (the day of the stock IPO (ticker:MPPP), the stock rose from $28 to peak at $103[2]), Robertson quickly led his company into a firestorm of lawsuits generated by the major record labels and music publishing concerns.

Although MP3.com purchased the CDs for their index and users had to supply their own copy as well, MP3.com violated copyright laws by failing to acquire licenses for the music that was internally duplicated by digitally storing the material on their servers.

After the trial started, in the case of UMG v. MP3.com, MP3.com was found to have violated copyright laws and ordered to pay as much as $250 million to Universal Music Group.

[4] This legal outcome triggered a class action complaint charging MP3.com and certain officers, including Robertson and company directors with violations of the Securities Exchange Act of 1934.

The action was ultimately resolved under the terms of an agreement whereby the defendants, while continuing to deny all liability, paid into an escrow account $35,000,000 and agreed to issue 2.5 million shares of MP3.com common stock which MP3.com valued at the time at $5,391,000, in exchange for complete dismissals and releases of all claims with prejudice.

The first line of the Court's opinion reads: "The complex marvels of cyberspatial communication may create difficult legal issues; but not in this case.

[10] Linspire championed an easy-to-use system for desktops and laptop computers and signed on popular retailers, both offline and online, including Walmart.com, TigerDirect, Frys and MicroCenter.

The San Diego Police Department investigated and quickly came to the conclusion that this was a simple dispute between Robertson and Linspire's CEO at the time, Kevin Carmony, and no embezzlement or other crime had been committed.

[14] Judge Taylor stated in his ruling, “It is plain to the court that Linspire [Robertson] was not required to act in the protection of its interests as it did.

Judge Judith F. Hayes stated in her ruling, "...the Court finds the general purpose of the website to be a free speech forum wherein Defendant criticized the management of Plaintiff.

In addition to selling phone adapters and routers, SIPphone developed free VOIP software to compete with Skype based on the SIP standard called Gizmo5, which is available on a variety of platforms.

Robertson boasted that, unlike Apple's iTunes Music Store and most other competitors at the time, MP3tunes did not use digital rights management (DRM) technology to limit the use of songs its customers purchased.

In April 2008, Robertson pleaded with the MP3tunes user group to help fund the legal defense regarding the EMI lawsuit.

The decision was viewed as a victory for online storage and cloud music services,[19] but the legal battle was very costly for the company.

Founded in early 2006 by Robertson (CEO) and Hisham El-Emam (CTO), Ajax 13 Inc. is a software development company that provides web-based applications written using XUL.

[22] In October 2012, Robertson filed a petition to legally change his name to Michael Lee Hammer,[23] alleging he was abused during childhood by his stepfather.

[24] In Judge William Pauley's ruling in the MP3tunes/EMI copyright trial, Pauley singled out the story Robertson told on the witness stand about this alleged abuse, stating that Roberton's "seemingly rehearsed, five-minute fable-like narrative left the jury nonplussed and Plaintiffs' counsel shell-shocked.