The series revolves around a trio of estranged siblings—Henry, an overachieving surgeon, Chloe, a former child prodigy with a smart streak who became the popular girl working at a bar, and Jimmy, an ex-con guitarist with a daughter (and who is in trouble with a loan shark over a debt)—who return home after their father's death. However, prior to his death, their father made a unique arrangement with his will: the siblings will inherit $23 million if they can follow his trivial wishes (through the use of the game Trivial Pursuit, customized with questions about their lives), which means that they have to rediscover their lives and hopefully be the people he wanted his children to be. But they are going to have to deal with competition from another person who was picked by their father and the appointed executor with whom Chloe is a former friend.

The series is created, written and executive-produced by Carter Bays ("How I Met Your Mother"), Craig Thomas ("How I Met Your Mother") and Chris Harris ("How I Met Your Mother"). Peyton Reed ("The Break-Up") also serves as an executive producer and director of the pilot.