Conlon was raised in Rathangan, County Kildare, Ireland, in a modest home; his parents struggled financially, with the bank at one point trying to repossess their house.
[1][5] Before emigrating to America in 1990, Conlon attended the College of Marketing and Design, Dublin and worked in London as a credit analyst, a job he disliked, and living in a "hovel that sat near the railroad tracks", with ten other men.
In 2004, in partnership with others,[clarification needed] he acquired Near North National Title, which was established in 1988 and processes billions of dollars in US real estate transactions each year.
[16] A "short marriage" was amicably dissolved early in Conlon's business career due to his "100-hour work weeks" and lack of time for a relationship.
[17] The engagement of Conlon and Imogen Hervey-Bathurst- great-granddaughter of Sir Frederick Hervey-Bathurst, 5th Baronet and maternal granddaughter of the businessman Martin Peake, 2nd Viscount Ingleby was announced in The Times and the Daily Telegraph on 16 March 2022.