On Day 1, four coaches entered into the game to coach the houseguests. Ian was placed on Mike "Boogie" 's team. On Day 48, Ian won his first HoH competition. After that initial victory, he went on to win the rest of his eligible HoH competitions. With his win on finale night, he tied the record of the most HoHs in a season: four. On September 19, 2012, Terry won Big Brother 14 and the $500,000 prize after defeating Dan Gheesling, who was the winner of Big Brother 10 and one of the four returning coaches, by a vote of 6–1. Terry is one of nine HouseGuests, including Drew Daniel, Janelle Pierzina, Rachel Reilly, Aaryn Gries, Hayden Moss, Caleb Reynolds, Vanessa Rousso, and Steve Moses in the show's history to win Head of Household four times in one season, and managed to avoid being nominated until Day 62, much to the collective chagrin of the house. Ian also holds the record for most consecutive HoH wins at 4. At 21 years and 6 months old at the time of his win, Terry became the youngest winner in American Big Brother history.