With the release of his first single in 2001, “Hell Bent”, Kenna gained moderate popularity and an underground following of fans who eagerly awaited the release of his debut album, New Sacred Cow. After many delays and swapping of record labels, the album was finally released under the Sony imprint Flawless in 2003. A subsequent North American tour was launched in the Summer of 2003 with Depeche Mode front man Dave Gahan.

On October 6, 2006, the world premiere of the song “Out of Control (State of Emotion)”, from Kenna’s EP entitled Black Goodbye Ride, was played on East Village Radio on Authentic Shit with Mark Ronson; it became available on iTunes on December 19, 2006.

Kenna’s second album, entitled Make Sure They See My Face, also co-produced by Hugo, was written over the course of three years, finishing in early 2007. The album was originally set to be released on June 5, 2007, then pushed back to June 19, 2007, finally being released on October 16, 2007. Kenna, in an interview with Vibe magazine, cited the reason for delays as being over the video for the album’s debut single. The inspiration for the album came from Kenna’s attempt to climb Mount Kilimanjaro, the title, inspired from phone calls by Pharrell asking Kenna; “are you going to make sure they see your face?”. Kenna’s climb took him to 18,200 feet before he fell ill from taking a sulfur-based altitude medicine, to which he had an unknown allergy. On October 23, 2007, the album debuted at #1 on the Billboard Top 20 Heatseekers Chart.

On July 7, 2007, Kenna opened the New Jersey portion of the Live Earth concert. He also toured with Nelly Furtado throughout various stops on her “Loose” tour.

“Never Let Me Down”, an unreleased track from the Make Sure They See My Face sessions, was released on the charity album Download to Donate for Haiti in 2010, in which the proceeds go to Music for Relief, Linkin Park’s charity. This album also contains “Resurrection”, a collaboration with Lupe Fiasco, which was accompanied by a music video.

In 2010, Kenna and Chad Hugo worked with Kid Cudi on a track unofficially titled “Capcom!” for a Street Fighter game. It was never officially released, but was streamed on the internet the following year.

When Kenna learned about the global water crisis affecting even his home village in Ethiopia, he decided to create the SUMMIT ON THE SUMMIT project, when he and friends Lupe Fiasco, Jessica Biel, Emile Hirsch and others climbed Mt. Kilimanjaro on January 7, 2010 to bring attention to the water crisis. The documentary on the climb aired on MTV on March 14, 2010.

A new song called “Turn” was made available as a free download on his official MySpace for a limited time. It has since been released on the iTunes Store on January 26, 2010. Proceeds from the sales of the track are donated to the SUMMIT ON THE SUMMIT project.

On February 13, 2011, Kenna announced plans over Facebook and Twitter to release a series of 3 EPs with 3 songs each, titled the Land 2 Air Chronicles, which will serve as the “runway” to his third album to be titled Songs for Flight, described by Kenna as a “first ever musical journey.”

The first EP, titled Chaos and the Darkness, was scheduled to be released on March 8, preceded by the first single “Chains”. The song was streamed on Kenna’s official website on February 22. On March 4, it was announced that there had been an unfortunate technical failure with the hard drive that stored the majority of the files that made up the songs for the EP and the album. Kenna rerecorded and reproduced all the songs, reworking the concept for the entire series. Chaos and the Darkness was eventually released on April 26, 2011, with “Chains” being available as a single on iTunes & Amazon on March 8.

The second volume of the Land 2 Air Chronicles series saw its release spanning three EPs, titled Imitation is Suicide Chapter I, Chapter II and Chapter III, respectively. Four singles would accompany their release, including “Relations (An Ode To You And Me)”, “Long Gone”, “Love Is Still Alive” and “How Will It End?”. All of them have an accompanying music video, with the exception of “How Will It End?”. The video accompanying “Long Gone” was filmed in an Hitchcockian-style and also marks Kenna’s directorial debut. It was released on MTV on October 17, 2012. Additionally, a remix to “Relations” featuring Childish Gambino was released on November 12, 2013.

Kenna’s strategic development company Translator serves as the umbrella for all of Kenna’s endeavors, including his music, technology and philanthropic efforts. In March 2012, Translator in partnership with Myspace produced a successful outdoor concert featuring Edward Sharpe and the Magnetic Zeros and Mumford & Sons at the annual South by Southwest Festival in Austin, Texas. The event saw more than 12,000 attendees and 1.3 million livestream views on Myspace. Kenna continues to curate and consult on many projects in tandem with his own music endeavors.

In 2013, Kenna released a cover of the U2 song “Gloria” to his SoundCloud and Myspace pages, as a way to reach out to Bono, one of his biggest musical influences. He received a call from Bono shortly thereafter.

The first single from Songs for Flight, “Sleep When We Die”, was released on July 15, 2015. It premiered on Zane Lowe’s Beats 1 Radio show on Apple Music, and was subsequently released for digital download.

“Sleep When We Die” was used to promote the launch of the Flipagram app in July 2015.