While at West Point, he served as class president before transferring to UC Berkeley, where he studied political economics.

[9] Painter left UC Berkeley before graduating to sell his first auto-related startup company, AUTOAccess, an electronic database listing used cars for sale.

[citation needed] In late 2011, TrueCar raised significant debt and equity capital (>$200m) which enabled it to advertise nationally on television.

[19] Consumer usage increased in response to the television campaign that was developed in conjunction with TrueCar investor Guthy-Renker, but dealer and industry criticism was significant and well documented in a series of Automotive News articles.

[20][22][23] As a result, Painter and TrueCar underwent a nine-month regulatory compliance overhaul and initiated industry outreach programs.

TrueCar went through a business turnaround in 2012 that resulted in the company reporting in its S-1 filing that it had generated positive adjusted EBITDA in 2013 after having lost over $40 million in 2012.

[25][26] In 2011 and 2014, he was named a finalist for the Ernst and Young Entrepreneur of the Year Award for the Greater Los Angeles Area.