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In 2012, after more than 25 million records were sold on Aware, Latterman decided to return to school. He attended the University of Pennsylvania, and earned a master's degree in positive psychology under Martin Seligman. In 2014 he began teaching at Northwestern, where his classes examine work ethics, talent, and entrepreneurial drive, and encourage students to integrate their passions and values into their professions.

As the new venture was built, Latterman realized that the day-to-day business of running the label limited his ability to be creative; rather than finding music and mentoring artists, he was focused on logistics and crisis control. In 2012, at 45, he decided to return to school. He enrolled in a master's program at the University of Pennsylvania, and in 2013, studying with Martin Seligman, he earned a master's in the field of Positive psychology.

Aware released more than 50 records in partnership with Columbia; in addition to multiple hit records from Train, Mayer, and Five for Fighting, the label had significant success with Guster, The Thorns, and Mat Kearney. In 2010, with more than 25 million records sold over the 15-year period of the joint venture, Aware entered into a new distribution agreement with Universal Republic.

In 2000, Latterman was sent an EP of John Mayer. He included two of Mayer's songs on Aware 8, and in early 2001, Aware released Mayers debut album, Room for Squares, as an internet-only album. It was re-released on Columbia in September, and went on to sell more than 5 million albums. Mayer was one of three Aware artists to receive Grammy nominations in 2002; Train was nominated for the album Drops of Jupiter, and Five for Fighting was nominated for their song "Superman (It's Not Easy)." Mayer won Best Male Pop Vocal Performance for "Your Body is a Wonderland." The ninth Aware compilation was released in January 2002; it was followed in October by a 14-song Greatest Hits collection. In 2009, The Fray's songwriters Joseph King and Isaac Slade filed a lawsuit against Latterman on the grounds that he failed to disclose that A Squared obtained ownership to a portion of the band's music when a publishing agreement was signed in 2005. Latterman countersued, alleging breach of contract. The suit was settled out of court in 2010. Although the terms of the settlement were undisclosed, a magistrate judge ruled that Latterman could argue at trial that the band's attorney was aware of terms of the publishing deal.

In 1999, Latterman founded A Squared Management. A Squared managed artists including Liz Phair, The Fray, Brandi Carlile, Michelle Branch, Motion City Soundtrack, Jack's Mannequin, Rachel Platten, Five For Fighting, and Mat Kearney. As The Fray's manager, Latterman worked with ABC to use The Fray's "How to Save a Life" on Grey's Anatomy,a placement that "catapulted the Denver band into another stratosphere, making its debut one of the best-selling albums of 2006."

In 1997, Aware and Columbia Records launched a joint venture that provided distribution for Aware's developing artists through RED, Sony's independent distribution arm, while at the same time serving as a "farm team" for Columbia—at a certain sales threshold, releases were moved to the Aware/Columbia imprint and marketed through Columbia. In 1998, Aware/RED released Train's self-titled platinum debut.,

Latterman received his MBA in 1996. Aware had a staff of eight and an office in Chicago; it had released the third Aware compilation—which included a track from Tabitha's Secret, the precursor to Matchbox 20—and produced the first Aware Tour. The company had put out full-length albums by Stir and Thanks to Gravity, and had set up one of the first online music stores, as well as a traveling store with the exclusive right to sell CDs on the H.O.R.D.E. Tour. Latterman had also served as an A&R consultant for Atlantic (in 1995) and MCA (in 1996).

As he prepared to release Aware 2, Latterman was accepted to the MBA program at Northwestern's Kellogg School of Management. He moved to Evanston, Illinois, and as a full-time student, he continued to build Aware Records. Aware 2, released in 1995, featured songs from artists who would go on to achieve significant success, including Better Than Ezra, The Verve Pipe, Vertical Horizon, Hootie & the Blowfish, and the Edwin McCain Band. Latterman became known for his ability to find and develop unsigned bands; within the music industry, an appearance on an Aware compilation was a "seal of approval, signifying an act worth pursuing."

A passionate music fan, Latterman put together a compilation CD of his favorite unsigned bands in 1993. He released it on his own label, and quit his job as a CPA on the day it came out. The label, Aware, became "one of the most durable and influential independent forces in music," with Latterman helping to launch the careers of artists including John Mayer, Train, Mat Kearney, Hootie & The Blowfish, and Five For Fighting.

After receiving his accounting degree, Latterman moved to Boston. He worked as a CPA at Coopers & Lybrand, a job he actively disliked, leading him to apply to MBA programs. He made mixtapes of unsigned bands who had developed a local following, selecting his favorite songs, and in early 1993 decided to produce a compilation album. Based on his own experience, he thought people from one city or state would buy a record to hear bands they already knew, and would be introduced to bands from other areas. Latterman learned the mechanics of making a CD and took out a $10,000 loan, and in 1993, working out of his apartment, he founded Madaket Records and put together Aware 1, a compilation CD of unsigned artists. On the day the album was released, he quit his job and moved to Vail, Colorado, where he coached the Vail Mountain ski team and developed strategies to promote the CD. Peter Margasak of the Chicago Reader later wrote that Latterman "knew little about the music industry when he came to it, but instead of dutifully learning and following its protocols, he developed his own."

Latterman attended Northern Michigan University on a partial athletic scholarship. He transferred to Michigan State in 1987 and graduated in 1990 with a degree in accounting. In 1996, Latterman received an MBA in marketing from the Kellogg School of Management at Northwestern University, and in 2013 earned a master's degree in Positive Psychology from the University of Pennsylvania.