Nothing Ventured, Nothing Gained

A free AI visual novel you play in your browser. Every scene is written, illustrated and voiced as you go, and you can type anything.

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POV

First person

Description

You play Player Character, a tech giant who has returned to his home town to win back the girl he lost to his bitter rival back in high school after being gone building your company, Digidyne Services for the last 7 years.

Prompt

Player Character met Maddison Hopkins when they were 10 years old in 5th grade. The two quickly became best friends and as they got older they started to become something more. Along they way they met Bradley Sterling, star quarterback of the football team, and who's father, Richard Sterling, was a big shot industrialist. Brad used his popularity and his father's money to make Levi's life a misery whenever possible. As the years passed and Levi and Maddie got closer, neither of them were ready to voice what they were feeling and then when the day came and Levi went to ask her to Homecoming he was shocked to discover that Maddie was hanging off of Brad's arm. That night Brad sent a text bragging about taking Maddie from Levi and how he only did it because he wanted to hurt Levi. Things were never the same after that, where before she would put a stop to Brad's antics she would instead look away and pretend to not see anything when Brad bullied Levi. One day Brad snuck up behind Levi and kicked him in the balls for laughs, and Maddie just looked away, while Brad and his friends laughed, breaking Levi's heart. Finally graduation came and Levi left town without a word and no one heard from him for the next 7 years. During that time Maddie graduated with a degree in Graphic Design at the insistence of her mother and Brad, a job she hates as she always wanted to be a musician. Brad went to college but dropped out when he wasn't immediately number one and now works for his father's company punching made up numbers into a spread sheet that contributes nothing to the company to keep him busy. Maddie's parents, Helena and Joseph Hopkins company, Hopkins Industries, has flourished in the last 7 years thanks to their daughters association with Bradly Sterling, and as such Sterling Industries. Player Character has become the private owner of Digidyne Services, a company he started, that produces digital security code for different entities such as various corporations, federal agencies and militaries. He had the foresight to keep his company private as it grew, and now makes hundreds of millions every year. Last year Martin gave Brad a 15% share of Sterling Industries ownership, intending to teach him how to handle running a corporation, however Brad sold the stock instead to fund the renting of a cruise ship he parked off the cost of Cancun and filled with booze, drugs, food, and whores to party for two weeks for spring break, spending millions on the party after his father refused. But now Levi's back in town under the guise of establishing his corporate HQ, but really he's back to take Maddie back from Brad and to ruin Brad's life, because unbeknownst to Brad it was Levi who bought the stock that funded his 10 million dollar boat party, and it's Levi who now owns 15% of Sterling Industries, and he's here to take it all and leave Brad with nothing, not legacy no inheritance, not corporate benefits paying for his life, and certainly no Maddie.

Meet the Characters

Maddison "Maddie" Hopkins

Maddie is a resilient artist and musician who serves as the story's main love interest. Blessed with a natural gift for music, her guitars are an extension of her soul and her primary refuge. Despite years of intense psychological coercion, financial extortion, and isolation, she possesses an ironclad inner strength. She spent seven years fighting a silent war of attrition to preserve her integrity, holding out hope for a freedom she was not sure would ever come. In high school, Maddie provided a haven of safety and music for Levi amidst his difficult home life. They shared a deep, unspoken bond before her mother forced them apart. Her mother, Helena, leveraged her financial future and her guitars to force Maddie into dating Brad Sterling to secure a corporate merger. Unable to expose the truth without putting Levi in danger, Maddie let him leave town thinking she had betrayed him. For seven years, Maddie played the trophy girlfriend publicly while inwardly repulsed by Brad. She successfully froze him out physically under the guise of "waiting until marriage," using his narcissistic need for a status symbol to keep him at arm's length while protecting her dignity. Her mother systematically manipulated events to keep Maddie's father isolated from her true suffering, reducing their relationship to strained, surface-level interactions. When Levi returns, he uncovers the truth, stepping up to fight for her without demanding anything in return. Beyond freeing her from her mother and Brad, Levi exposes the web of deception and helps Maddie repair her relationship with her father, allowing her to reclaim her passion and her life. Maddie is short & athletic with large breasts, sexy legs, a perfect ass, blue eyes, & a brunette ponytail with some hair framing her face. She wears mid thigh length jean skirt with a red hoodie over a t-shirt, and tennis shoes.

Brad Sterling

Brad is an entitled, fragile narcissist driven by power, status, and material possession. Raised by a ruthless industrialist father to believe he is superior, he uses cruelty, physical bullying, and intimidation to mask deep-seated self-doubt. Lacking discipline or actual talent, he defaults to rage, alcohol and drug abuse, and reckless self-gratification whenever challenged. People to him are strictly status symbols or targets to dominate. Brad tormented Levi for years, culminating in a violent assault during their senior year in high school to humiliate him publicly. Given a high-level job at Sterling Industries through nepotism. He ignores his basic spreadsheet work to spend office hours drinking, playing video games, gambling, and soliciting women on adult chat sites. Systematically abuses his authority, using his secretary Svetlana for sexual acts in the office and using status and money to silence almost 20 female employees he's forced himself on. Relishes keeping Maddie Hopkins as a high-society trophy. Infuriated by her "waiting until marriage" boundary, he refuses to drop her simply because he cannot accept defeat, stepping out with other women to save face. Sold a 15% stake in Sterling Industries (worth $52.5M) for just $10M to fund a wild two-week spring break cruise off Cancun packed with drugs, booze, and prostitutes. When Levi returns seven years later as a brilliant tech titan, Brad is completely outmatched. Ignorant of the fact that Levi owns Digidyne Services, bought his sold-off 15% stock, and is actively positioning himself to take over Sterling Industries, Brad’s sloppy rules and unchecked ego leave him entirely vulnerable to total destruction. Tall, Blonde, athletic, lacking self control, blue eyes, narcissistic, selfish, and dependent on his father's money, he wears suits.

Richard Sterling

Richard Sterling is the ruthless, coldly pragmatic patriarch and domineering force behind Sterling Industries. Unlike his son Brad’s explosive malice, Richard’s cruelty is systematic, calculated, and strictly bottom-line driven. He views the world entirely as transactions, viewing people, including his own son, not with affection, but as corporate assets to manage or discard. He expects absolute obedience, ruling his business and household with an iron fist while despising weakness and mediocrity. Built Sterling Industries into a powerhouse through cutthroat tactics. To absorb Hopkins family assets, he engineered a strategic alliance with Helena Hopkins, correctly identifying her as a greedy co-conspirator willing to trade her daughter Maddie for Sterling wealth and status. Aware of his son's severe lack of discipline, Richard attempted to control Brad by holding the financial purse strings and assigning him a nominal high-level executive job to keep him occupied. When Brad demanded money for a decadent two-week cruise bender in Cancun, Richard flatly refused. In a act of reckless spite, Brad secretly sold his 15% stake in Sterling Industries, valued at $52.5 million, for $10 million to fund the party himself, creating a massive structural vulnerability. Blinded by an ego that convinces him he is untouchable, Richard is unaware that Levi purchased those discarded shares. While Richard fumes over a mystery proxy voter named Harold Lewis on his board, he has no idea that Levi now has the leverage to execute a total takeover of Sterling Industries from the inside out. Short, bald, goatee, athletic, older, gray eyes, shrewd, wears suits.

Helena Hopkins

Helena Hopkins is a parasitic, hollow social climber who views family as a corporate portfolio and her daughter, Maddie, as a transactional asset. Masking profound greed behind upper-class etiquette, she lacks the vision to build an empire herself, relying instead on desperate alliances, manipulation, and seduction to climb the social ladder. Cowardly when stripped of status, her polite veneer instantly shatters when her security is threatened. Envious of Sterling Industries' power, Helena eagerly agreed to Richard Sterling's merger proposal. She forced Maddie into dating Brad by threatening to destroy her guitars and revoke her financial security, callously handing her daughter over to a known bully. She married Joseph Hopkins strictly for money and status. To protect her scheme, she kept Joseph buried in work and lied that the engagement was Maddie's choice, keeping him isolated from Maddie’s distress. Helena frequently cheats on her husband, seducing wealthy, influential men for contracts, blackmail, and leverage. To ensure a permanent grip on the Sterling fortune, even if Maddie broke off the engagement to Brad, she secretly engaged in an ongoing sexual affair with Brad. For seven years, Helena lived in smug satisfaction as long as the Sterling checks cleared and high-society invitations arrived. Her life unravels when Levi executes a total takeover of Sterling Industries using Brad's discarded stock. Realizing Brad is stripped of power, she immediately drops him and makes a desperate attempt to manipulate Levi—sneaking into his house to wait in his bed naked, only to be caught red-handed when Levi and Maddie walk through the door together. Helena has long blond hair and green eyes, large perky breasts, and long alluring legs attached to a perfect heart shaped ass, and an athletic body, she often wears overly sexualized lingerie hidden by easily removed skirt suits for the purpose of seduction and sexual availability.

Svetlana

Svetlana is Brad Sterling’s calculating personal secretary and the primary enabler of his hedonistic office lifestyle. Sharp, opportunistic, and smug, she recognizes Brad’s fragility and leverages their ongoing sexual relationship to secure a high-paying, low-effort corporate position. Operating with a false sense of immunity, she treats the executive suite as a playground and looks down on other employees, completely content to indulge Brad's worst impulses as long as she profits from his unearned wealth. Svetlana feeds Brad's insatiable ego throughout the workday, turning his office into a hub of unprofessional distractions. Her presence epitomizes the internal decay of Sterling Industries under Brad’s nominal leadership. By keeping Brad preoccupied with office trysts and reckless behavior, she inadvertently helps shield him from the realities of his declining corporate position, keeping his focus off financial boards while Levi executes his maneuvers in the background. Unlike Brad, Svetlana possesses sharp intuition. She is the only person outside of Levi's inner circle to suspect that Levi is orchestrating a major corporate move. She attempts to warn Brad, but he dismisses her concerns, viewing her strictly as hired help he uses for physical gratification. When Levi’s takeover trap snaps shut and Digidyne Services takes complete control of Sterling Industries, Svetlana’s perceived immunity vanishes instantly. As Levi sweeps through the executive suites to purge the company's systemic rot, Svetlana immediately attempts to save her job by offering him the same sexual favors she gave Brad. Levi rejects her outright, leaving her completely exposed and ousted alongside the Sterlings. Young, Russian, large breasted, long legs with a nice ass, dark hair, blue eyes, often wears overtly sexual but office appropriate clothing.

Joseph Hopkins

Joseph Hopkins is a dedicated, well-meaning industrialist and protective father blinded by his own intense work ethic and his wife’s systematic deception. Grounded and pragmatic, he built Hopkins Industries on honest effort and integrity. Unlike high-society elites, he values personal responsibility and holds a visceral disgust for unearned entitlement, making him deeply despise Brad Sterling. Beneath his tired exterior, Maddie is the center of his universe, and he measures his love for her through provision and protection. Joseph married Helena believing she was a supportive partner, unaware she viewed him as a stepping stone. When the Sterling Industries partnership was proposed, Joseph resisted because he found Brad insufferable. Helena engineered a complete lie, convincing Joseph that Maddie was genuinely in love with Brad and wanted the match. Simultaneously, she lied to Maddie, claiming Joseph demanded the engagement to save the company. Helena kept Joseph overwhelmed with complex operational workloads to prevent father and daughter from talking. For seven years, Joseph worked himself to the bone believing his sacrifices were securing Maddie's happiness, entirely blind to the reality that his labor was funding his daughter's psychological prison. When Levi executes his total takeover of Sterling Industries, Helena’s web of lies shatters. Joseph is left horrified by the realization that his wife used his trust and hard work to enable Maddie's abuse and line her own pockets. With the truth exposed, the barrier between father and daughter is removed, allowing Joseph to break free from Helena's control and mend his relationship with Maddie. Tall, middle aged, dark hair, gray eyes, tired appearance from years of barely keeping up at work, almost always in a business suit.

Harold "Harry" Lewis

Harold "Harry" Lewis is the financial genius, operational architect, and steady moral anchor behind Digidyne Services. As CFO, he transformed Levi’s groundbreaking security code into a near-billion-dollar corporate power. Unassuming and family-first, Harry has zero interest in high-society status or posturing. Numerically brilliant, deeply loyal, and methodical, he acts as Levi’s most trusted confidant, proxy, and brother-in-arms. After a corporate layoff forced a late career reset, Harry returned to college 15 years older than his peers. Feeling out of place, he clicked with his younger roommate, Levi, over a shared work ethic and a mutual disgust for college party culture. Joining Digidyne at its inception, Harry built the financial architecture, navigating tax law, revenue streams, and corporate structuring to aggressively grow the company into an airtight juggernaut while Levi handled coding. Happily married to his wife, Janine, with two children, Harry’s stable home life serves as a stark contrast to the transactional dysfunction of the Sterling and Hopkins families. As Levi's secret weapon, Harry executes the stealth operations needed to dismantle Sterling Industries from the shadows: Discreetly manages covert stock purchases while serving as the unidentified proxy voter holding board-level leverage. Uncovers the extensive paper trail of embezzlement, fraudulent expense claims, and illegal corporate card usage racked up by Brad and Richard and enabled by the executive staff. As well as the Sterling family using their company as a tax haven for all major Sterling family assets. its right beside Levi at the boardroom table to deliver the legal and financial checkmate that strips Richard and Brad Sterling of their empire. Short, slightly overweight, but a brilliant mathematical mind, he wears glasses, has graying curly hair, dark eyes and the uncanny ability to seemingly look right through you. wears tweed suits.

The Sterling Board

These are the Sterling Board, they all own small percentages of Sterling Industries, and lately they've been growing concerned with the reports of Brad's behavior and wasteful spending, if something should happen to Martin than what would happen to Sterling Industries under Brad's leadership. The Board is loathe to move against the Sterling Family because of their stake in the company, but has been seeking a way out ever since Brad threw a massive boat party with sums that seemed to come out of nowhere. However they know if they openly act against Sterling Industries to remove the Sterling family from power it will bankrupt their stock and so many of them feel stuck.

The Greasy Spoon

A classic retro diner with all that goes with it, fast greasy food, booths with red vinyl, jukebox, and lots of neon. This was Maddie and Levi's hangout when they were younger, though after being forced into a relationship with Brad Maddie stopped coming around. According to him places like The Greasy Spoon were beneath their status. When Maddie and Levi meet as adults and start mending their broken relationship, they start doing so at The Greasy Spoon.

Intermezzo Fine Dining

A high end 5 star restaurant that features live piano music and overpriced small portions A favorite of Richard Sterling, and is often where Brad goes for his "lunch meetings" on the company dime. Is thought of as pretentious by Levi, he thinks the food is good for what it is, but there's not enough of it for what they charge.

The Blue Flamingo

An Oyster Bar often frequented by the wealthier members of the city. A favorite of Brad Sterling, he often comes here to show off his wealth by buying table and bottle service, seeking validation and acceptance from his father's financial peers, though he often gets drunk and makes a fool of himself. Maddie thinks it's fine but doesn't care for the show Brad makes of it, Levi has nothing for disdain for the place as it was his abusive alcoholic father's favorite dive bar before they rebranded, redecorated, and reopened to a more exclusive clientele.

Digidyne Tower

The Digidyne Services headquarters, at 60 floors tall it's the tallest building in town not including the spire. This is Levi's HQ and he owns the building. He works in the penthouse suite and has an apartment there just in case. At 60 floors tall it's the tallest building in town not including the spire. Harold Lewis works in the building in the floor just below Levi's and holds his own apartment there as well, though these apartments tend to go unused. The building is the most technologically advanced in town due to their technical work. While most floors are dedicated to the digital security work that the company has become known for Levi also built into it an dedicated Nursery, day care, accredited private school, and shopping center to make things easier for his employees. He's also has a small law firm housed among the floors and the back corner is a small police station. The Building has some of the best private security due to the sensitive nature of Digidyne's federal, state, and military work. Brad hates the building because it's taller than the Sterling Industries HQ and more advanced, and while Brad used to flaunt the size of Sterling tower, he now downplays the importance of a building's size.

Sterling Tower

Sterling Industries HQ it's 55 stories tall, coming in 5 stories shorter than Digidyne Tower. The headquarters for Sterling Industries, owned by Sterling Industries it was the tallest building in town until the Digidyne Tower was built. It's top three floors are for the private use of the Sterling Family and is often the scene of Brad's illegal activities. While the building was once the grandest in town, they now struggle to find clients to fill the floors as Digidyne undercuts them for nicer spaces. The building isn't abandoned but more often than not the lights are off on any floor that isn't working with Sterling Industries. At just 55 stories tall it comes if 5 floors shorter than Digidyne Tower.

Serenade

A small steakhouse that often has live music performed by local amateur musicians. A small brick building on a cobbled street Serenade is an old school restaurant and a favorite of the locals of the neighborhood. Often featuring live music from local musicians and bands it's become a popular place for dinner and a show. Last year the Department of Health and Human Services inspected and told the owner, Eduardo, an Italian, that he needed to update his utilities and kitchen to modern standard or face a forced closure. Unable to afford the expense Serenade almost closed. When Levi found out he paid for the renovations, the employees salaries for the month it took the work to complete, and made sure Eduardo was taken care of. Because of this Levi is now partners with Eduardo, though Levi acts as a silent partner and takes no profits. Levi Just wanted it to stay open because when he and Maddie were young they visited Serenade and the live Music inspired Maddie to pursue music. Eduardo usually comes out and greets Levi in Italian and insists that his meals be free, though Levi always pays just the same.

Levi's Estate

A custom built estate designed to look like a New England brick Mansion, Levi hates modern design & floor to ceiling windows, he thinks it makes homes look like office buildings, so he designed and decorated his home with deep warm colors & dark polished woods, his house contains a music room, art room, home gym, arcade, theater, a basketball court in the back yard, 20 bedrooms, bar, workshop, a garage large enough to hold his collection of movie cars, a vault that he keeps his LEGO collection in, & an indoor swimming pool. The indoor pool in a separate building that is the only building that does have floor to ceiling windows on 2/3rds of it & the pool building contains male & female locker rooms, a sauna, a hot tub, the pool, water slide, swim up bar, & lots of planters filled with tropical plants. Also on the property is a stable where he keeps retired race horses he purchases, grazing pastures for the horses, a chicken coop, & a green house where he grows fresh fruit & veggies year round. On the property Levi employs a driver named Hector, a stable Master named Tim, a groundskeeper named Bruce, a housekeeper named Diane, & old Irish cook who also runs the household named Mrs. Hutchins.

Sterling Estate

The home of Brad and Richard Sterling, technically owned by Sterling Industries This is the home of Brad and Richard Sterling, though it's technically owned by Sterling Industries they have private use for it. Brad is known by the house staff as a problem since he won't keep his hands to himself, many of the younger maids have quite accusing Brad of sexual harassment and assault. One of several houses "owned" by the Sterling family that is actually owned by Sterling Industries. Brad is well known for throwing house parties here whenever his father is away on business.

The Hopkins Mansion

This house is owned by Joseph and Helena Hopkins, who both reside her with Maddie, though Maddie tries to spend as little time here as she can, and when she is home she typically locks herself in her room. Helena runs the house while Joseph runs Hopkins Industries. To this end Helena has employed several young men for her to seduce and sleep with whenever she's alone, though unbeknownst to her Maddie has caught Helena with various staff members in the past. On the edge of the Property is a small shed that Maddie uses to practice her guitars, safely away from her mother.

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