[2] In 1995, he dropped out of West Point and enlisted in the United States Marine Corps with his time in the Marines strongly influencing the development of his '33 principles for investment'[3] He got his undergraduate in Information Technology from the University of Maryland, later earning an M.B.A from National University.
[5] After the Invasion of Iraq in 2003, he created the Lincoln Group and started winning Pentagon contracts to assist with "psychological operations".
From 2010 to 2012, he was the CEO and cofounder of BetterWorks, whose mission was to help smaller companies create office cultures of offering abundant perks.
[2][5] In May 2012, in what he described as the "lowest point of his professional career", he shut down the company and returned the remaining capital to his investor.
He acquired an early-stage portfolio that included Airbnb, Lyft, AngelList, Postmates, and Klout.