"It was remarkable to me how he never wanted to get into trouble," Grant says. "We don’t have any incriminating evidence [against him]."LOFTY AMBITIONS

Grayson first told his future roommates about his passion for politics when he wrote them during the summer before their freshman year, according to Wood.

"He quickly announced his intention to become president," Wood says.

When Grayson later found out he was living in John F. Kennedy’s room in Weld, he put up a poster of the former U.S. president on his wall.

As an undergraduate, Grayson also cross-enrolled at the Harvard Kennedy School, where he took classes on financial regulations and health policy.

His interest for politics led him to attend his first forum at the IOP in 1990. The event—titled "Personal Perspectives in Politics"—raised his interest in the institute.

Grayson quickly got involved with the IOP and eventually became the Vice Chair of the Student Advisory Committee.

He says the IOP helped him develop the bipartisan approach to politics he became known for as a politician. He identified as a Democrat during his undergraduate years, yet his experience at the IOP exposed him to a wide range of political views.

"Almost everyone here has a [specific] point of view, but we [all] care about politics for its own sake," Grayson says.

THE ROAD TO THE STATE CAPITAL

Although Grayson had always had an interest in politics, the final impetus to begin his political career came over a burrito. He was working as an attorney at the time and had gotten involved in local politics while organizing an event during President George W. Bush’s 2000 presidential campaign. During the event, he became close with a group of local political organizers, who would be instrumental in his later political career. And it was a lunch invitation from one of these friends that began his career as an elected politician.

"One day I get this email. The subject is ‘Lunch at Joe’s?’ and the body of the email said ‘Topic: Grayson for [Secretary of State]. Time: 11:30’ and I replied ‘Time: good, Location: good, Topic: not so good," said Grayson. "But we went anyway and ... that was sort of where it was hatched."

Typically someone without political experience cannot decide to run for a state-wide office and win on their first try. But Grayson benefited from the Republican party’s unfortunate luck in the state of Kentucky. For decades before Grayson ran for office, Democrats had consistently won all of Kentucky’s constitutional offices, from Governor to Secretary of State. Because of the Democratic party’s near monopoly on state power at the time, few career Republicans wanted to dedicate their time running for office, leaving a void for a 31-year-old with no past political experience.

Grayson was sworn in as Secretary of State of Kentucky in 2003 and was the youngest Secretary of State in the nation at that time. During his time in the position, Grayson focused on moving many of the state’s services online.

Although Grayson says that he enjoyed his time in office, he acknowledged that the job is not necessarily as advertised.