Growing up in Queens, Mark Mason carried a Samsonite briefcase with him to school. It was filled with bubblegum, baseball cards, and he sold them to other students at lunch. Mason claims that his grandmother wanted Mason to be a doctor to treat her arthritis. However, Mason said that he was aware from an early age that he had a natural talent for business. His decision to study finance at Howard University was a pivotal moment. Mason, a 156-year old, private university, says that it was a chance to learn from and with Black people all over the globe. Howard's case study approach prepared him for Harvard MBA. Mason was a key strategist at Marakon Associates, Lucent and Citi before moving to Citi in 2001. Mason has played key roles in critical moments over the past 20 years, starting with the joint venture between Smith Barney & Morgan Stanley and ending with the running of Citi Holdings, the unit that was created after the financial crisis to house high-risk assets. Mason's first reaction was: "You want me running the bad bank?" Mason began his career in consulting following business school. He then moved to Lucent to study technology. One of the lessons Mason learned was that you can't be one person. If that person was let go, then I was let go too. The bigger question these days is how to keep Mason, given Mason's track record at Citi. Mason discusses his pivotal moves at Citi, the reason he lies on the ground and the strategic way that he uses a plaque to place on his desk that reads: "What would you do if it was certain you couldn't fail?"