====Father: Jack Calloway====

Nickname: “Jack of Jacksonville”

Occupation: Commercial Real Estate Mogul

Description: Charismatic, driven, and sharply dressed, Jack built his brand around high-end beachfront developments and lucrative urban flips. His face is a local fixture on billboards and bus benches across Jacksonville. A classic businessman through and through, he hoped all his kids would follow in his footsteps. Jack helped broker the redevelopment deal for his property deal that would eventually become Jessie’s domain. Though initially skeptical, he’s proud of Jessie’s success—especially since it finally aligns with something tangible and profitable.