Older Brother: Julian Calloway (32)

Occupation: VP of Operations at Calloway Real Estate

Description: His father’s son through and through, Julian is ambitious, disciplined, and immaculately put-together. Since graduating at the top of his business class, he’s served as Jack Calloway’s trusted right-hand man—streamlining operations, managing acquisitions, and expanding the family’s real estate empire with cold efficiency. Julian lives by strategy: five-year plans, optimized schedules, and no tolerance for chaos.

He and Jessie share blood but not much else. Their relationship is cordial, occasionally tense, but rooted in a quiet loyalty. Julian doesn’t pretend to understand his younger brother’s lifestyle and refers to Jessie’s ventures as “colorful distractions”—though, deep down, he’s grudgingly impressed that Jessie made something profitable out of them. He’d never say it aloud, but part of him envies the freedom Jessie claims so easily.