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.
Occupation: Event Planner turned Social Organizer
Description: Elegant and effortlessly charming, Ellen Calloway built her reputation hosting charity galas and high-society fundraisers, often knowing how to get people in a room before they even knew they wanted to be there. She’s tactful, graceful, and carries herself with the poise expected of a Jacksonville power couple’s matriarch.
But beneath that well-maintained exterior is a kindred spirit to her youngest son. Ellen shares Jessie’s appetite for beauty, mystery, and experience—she just learned early how to channel it within the expectations placed on her. In another life, she might’ve been a dancer, a mystic, or an artist traveling the world barefoot. She sometimes looks at Jessie with a mix of admiration and wistfulness, proud of him for walking a path she once dreamed of, even if it unsettles her husband and older children.
She doesn’t always understand Jessie’s world, but she supports him quietly and fiercely, and she’s the only one who never calls his pursuits “a phase.”
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.
Background: Boutique consultant
Description: Elegant and composed, Lottie has a keen eye for luxury markets and trend forecasting. She and Julian are a power couple in every sense—publicly flawless, privately pragmatic. Lottie admires Julian’s drive but sometimes rolls her eyes at his rigidity. She has a dry wit and occasionally checks in on Jessie out of genuine curiosity (and mild concern).
Description: Xan is bright, well-mannered, and already fluent in “dinner table diplomacy.” Enrolled in a prestigious prep school with a structured schedule full of piano lessons, chess club, and junior coding classes, he’s clearly being groomed to follow in his father’s polished footsteps.
But at 8, the cracks of curiosity are already showing. He doodles in the margins of his business ethics homework, daydreams during Mandarin class, and quietly idolizes his Uncle Jessie, who once told him that “coloring outside the lines is where all the good magic happens.” Xan keeps a secret notebook of stories and dreams, hidden behind the books in his meticulously curated shelf.
Description: Where his older brother Xan is thoughtful and serious, Bennett is all energy and mischief. He’s a blur of grass-stained knees, endless questions, and unapologetic joy. He once tried to “surf” down the stairs on a hotel brochure and insisted Uncle Jessie had given him the idea. Bennett laughs loudly, hugs hard, and somehow wins over even the sternest adults. His mother Lottie says he’s “going to be either a CEO or a cult leader.”
Occupation: Attorney specializing in Property Law
Description: Smart, sleek, and unflinchingly direct, Rebecca married young to another rising legal star and now works high-end real estate contracts in Miami. She’s fiercely intelligent and loyal to her family but often critiques Jessie’s “artsy, offbeat nonsense.” Still, she has secretly helped him with zoning hurdles and liquor licenses more than once—discreetly, of course. She refers to Jessie as “our family's spirit animal,” usually with affectionate sarcasm.
Occupation: Corporate Counsel for a major tech firm
Description: Calm, analytical, and razor-sharp, Adam is the steadying influence in Rebecca’s life. He doesn’t need to be the center of attention—he prefers to win arguments with quiet logic. While Rebecca’s intensity can overwhelm others, Adam meets her fire with calm water. He gets along with Julian. With Jessie? Let’s say the jury’s still out, but he’s polite.
Description: Bright, observant, and already arguing like a junior lawyer, Sophie is precocious but not obnoxious. She adores her Aunt Ellen and has a secret fondness for her Uncle Jessie, who tells her stories no one else will. She once tried to convince her mom to let her visit the Dolphin “just to see the secret room.” Jessie calls her the spy in ruffled socks.
Description: Clara is quiet, observant, and fiercely attached to her big sister Sophie. She rarely speaks in groups but will whisper bold ideas when she trusts someone. She likes books, flowers, and being near grown-ups when they’re talking—as long as no one tries to make her the center of attention.
She calls Jessie “Uncle Sunshine” and is completely convinced he can talk to animals.
Description: A tornado in toddler form, Theo is a clingy chaos goblin with sticky hands and an intense dislike of bedtime. He is either absolutely silent or yelling. His favorite word is “mine,” and his favorite person is whichever adult picks him up and lets him ride on their shoulders. He has no idea who Jessie is but once bit him on the leg.