Risky Business Summary, Characters and Themes | Annabelle Slator

Risky Business by Annabelle Slator is a sharp contemporary novel about ambition, gender bias, shame, reinvention, and the cost of pretending. At its center is Jess Cole, a determined founder trying to save her women’s health start-up, Wyst, while carrying the damage of a past workplace scandal that was never truly resolved.

When a mistaken application turns her into “Mr. Cole” in the eyes of a major start-up competition, Jess takes a dangerous shortcut that opens doors usually closed to her. The story mixes workplace satire, romance, and personal recovery as Jess fights to be heard on her own terms.

Summary

Jess Cole is the founder of Wyst, a women’s health start-up built to give women free, reliable access to advice from trained professionals. She believes deeply in the company’s mission, but belief is not paying the bills.

Wyst is running out of money, her personal finances are in a mess, and every possible funding route seems to end in rejection. Jess is exhausted, embarrassed, and close to losing the business she has poured herself into.

Her latest hope is Will Salter, a possible investor she agrees to meet at a London wine bar. Jess arrives ready to pitch Wyst, but the meeting goes wrong almost immediately.

Will treats the appointment like a date, orders an expensive bottle of wine, talks about himself, and shows little interest in the company. When Jess tries to steer the conversation toward business, he dismisses FemTech and makes it clear he never planned to invest.

Worse, he recognizes Jess from an old incident at Graystone, where private photos taken without her proper consent were shared and used against her. The scandal damaged her career and left her with lasting shame and anxiety.

Will insults her and walks out, leaving her with the huge bill.

Back at Wyst, Jess vents to Cecily, her PR and marketing manager, and Pacha, the company’s developer. While trying to recover from the humiliation, she discovers a last-minute opportunity to enter TechRumble, a powerful start-up competition run by Odericco Investments.

The prizes include cash, investor attention, and the kind of credibility Wyst desperately needs. After joking that perhaps she should apply as “Mr. Cole” because men seem to be taken more seriously, Jess accidentally submits the application that way.

The next morning, Odericco Investments replies to “Mr. Cole” and invites Wyst to schedule a call. Jess knows she should correct the mistake, but fear stops her.

She has been ignored and underestimated as a woman founder too many times. The idea that Wyst might finally get a chance because the organizers think the founder is a man is both infuriating and tempting.

Around the same time, Jess and Cecily meet Dr. Bernadette Reid, a well-known mental-health podcaster Jess wants as the face of Wyst. Dr. Bernie is interested, but she expects proper payment and a real contract.

Jess, desperate to look more secure than she is, suggests that funding is close.

To keep the competition opportunity alive, Jess asks Pacha to create a voice changer so she can take the Odericco call as “Mr. Cole.” During the call, she pitches Wyst as a professionally vetted platform offering women support from therapists, doctors, and experts. She exaggerates the company’s size, claims Dr. Bernie is involved, and talks about future expansion.

The voice changer briefly fails, forcing Jess to invent an assistant named Violet to explain the sudden change in voice. Despite the near disaster, Wyst is invited to the first round of TechRumble in Rome.

Jess then needs someone to physically appear as Mr. Cole. She turns to her twin brother, Spencer, an actor.

Spencer is shocked by the deception, but he agrees after Jess promises that Cecily will help promote his next play. Their plan is simple: Spencer will pose as Wyst’s CEO, while Jess will pretend to be Violet, his assistant.

The lie immediately shows Jess how differently people treat them. In Rome, Spencer receives VIP treatment as Mr. Cole, while Jess is given cheaper accommodation and less respect.

At the hotel, Jess meets Oliver, a handsome American assistant, after he accidentally spills coffee over her. Their first meeting is awkward but charged with attraction.

Oliver arranges for her coat to be cleaned and later leaves a note inviting her for a drink. Meanwhile, Spencer prepares to present Wyst at TechRumble, using Jess’s words through an earpiece.

The pitch begins well, but Spencer soon starts improvising. He promises features Wyst does not yet have and presents himself as a model male feminist.

The mostly male audience responds warmly, but Jess is furious and frightened. Spencer is winning them over by taking credit for her work and making commitments she cannot keep.

Jess slips away and meets Oliver at a bar where assistants and interns are gathering. Calling herself Violet, she relaxes with him over drinks and games.

For once, she feels free from the pressure of being Jess Cole, failed founder, scandal survivor, and woman constantly fighting to be believed. Yet the relief is built on a lie.

Oliver knows her only as Violet, while Wyst’s future depends on Spencer continuing to impersonate her.

As the competition continues, Jess learns that Dr. Bernie may partner with a rival period-pants start-up, which threatens Wyst’s plans. At a networking event, Dominic Odericco reminds the contestants that they represent some of the best start-ups in the competition, giving Jess hope that even recognition could help Wyst.

During speed networking, however, she sees Malcolm Steward, the former colleague who ruined her life. The sight of him triggers panic.

Spencer notices her distress and helps her avoid facing Malcolm directly, but Jess later runs into him by accident. Malcolm recognizes her, though she denies it and escapes, physically sick with fear.

At a rooftop mixer, Jess tries to believe Malcolm cannot hurt her there. She talks with Oliver at the bar, but he senses her confusion and asks about her behavior.

Their conversation is interrupted when Jess cuts her hand and Oliver helps her. Then she sees Malcolm watching them.

Jess realizes he knows Violet is really Jess and that Spencer is not Wyst’s CEO. Terrified, she tells Oliver only that her ex is at the conference and asks him to take her away.

Oliver takes her into town, where they have dinner. He opens up about his father’s death, his abandoned dream of culinary school, and the depression that pushed him into his current assistant role.

Jess shares part of her own history. She tells him that Malcolm took intimate photos without proper consent and shared them with colleagues.

Graystone pressured her into signing an NDA instead of going to the police, and although Malcolm was removed, Jess was left carrying the shame. Eventually she left because staying became unbearable.

The honesty draws them closer. Later, they kiss in the rain, but Jess refuses to go back to his room because she must leave.

When she returns to the hotel, she learns Wyst has advanced to Vienna.

Back in London, Jess has given up her flat and is effectively homeless. Cecily quietly steps in, sending an Uber and bringing Jess to her family townhouse.

She offers Jess a place to stay and celebrates Wyst’s success. Jess admits she should stop seeing Oliver because he still believes she is Violet, but Cecily encourages her to enjoy one more night at the Vienna ball.

Cecily then realizes the final TechRumble event will take place at the prestigious Philharmonic Ball at Musikverein, meaning Jess must prepare for a much grander setting than expected.

Complications build before Vienna. Spencer has an important BBC America audition on the same day as the final round, leaving Jess worried he may not arrive in time.

She contacts Oliver under the excuse of returning his umbrella and later goes to his apartment, where he cooks handmade pasta and desserts for her. Their connection deepens, but when he calls her Violet during an intimate moment, Jess’s guilt stops her.

Before she can explain, an anonymous text from Malcolm proves he knows exactly who she is. Jess panics and leaves abruptly.

Malcolm later confronts Jess outside the Wyst office. He reveals he has been watching the company and knows Spencer is only an actor.

He threatens to expose the lie unless Jess publicly retracts her accusation and apologizes to him. Jess refuses, but Malcolm warns that he will wait until Vienna, when Wyst’s success will make the story more damaging.

After he leaves, Jess breaks down.

At her mother’s birthday dinner, Jess’s parents criticize her for involving Spencer and blame her for the continuing trouble with Malcolm. Jess finally pushes back, and Spencer defends her, praising her intelligence and hard work.

The siblings leave together for Vienna. Jess arrives at the final stage of TechRumble carrying everything at once: Malcolm’s threat, Wyst’s financial crisis, her guilt over Oliver, Spencer’s uncertain role, and the burden of proving that her company deserves to survive without hiding behind a man’s name.

Characters

Jess Cole

Jess Cole is the central figure of Risky Business, and her character is built around ambition, fear, shame, resilience, and the exhausting pressure of being taken seriously as a woman founder. She is not simply a struggling entrepreneur; she is someone fighting to protect an idea that matters deeply to her while also trying to survive the emotional damage of a past violation.

Wyst, her women’s health start-up, represents her intelligence, her belief in accessible professional support for women, and her refusal to accept that female-focused technology should be dismissed as unimportant. At the same time, Jess’s decision to continue the “Mr. Cole” mistake shows how deeply sexism has shaped her choices.

She knows the deception is dangerous, but she also understands that men in the investment world are receiving the respect and attention she has repeatedly been denied. This makes her morally complicated in the book: she lies, exaggerates, and pulls others into the scheme, yet her actions come from desperation rather than greed.

Jess’s trauma is one of the most important parts of her characterization. Malcolm’s betrayal and the way Graystone handled it have left her with panic, shame, and a constant fear of exposure.

Her physical reactions when she sees Malcolm show that the past is not behind her; it lives inside her body and controls how safe she feels in public spaces. She is also emotionally isolated, partly because her family fails to fully support her and partly because she has learned to protect herself by withholding the truth.

Her connection with Oliver reveals the softer, more open side of her personality. With him, she briefly becomes playful, vulnerable, and hopeful, but even that romance is shadowed by guilt because she is pretending to be Violet.

Jess’s journey in the story is therefore not only about whether Wyst can survive, but whether she can reclaim her own voice after powerful people tried to silence her.

Spencer Cole

Spencer Cole, Jess’s twin brother, is both comic relief and an emotional anchor in the book. At first, his role in the “Mr. Cole” plan seems absurd: he is an actor pretending to be the CEO of a women’s health start-up he does not truly run.

His theatrical instincts help him perform confidence in front of investors, but they also create problems because he enjoys the spotlight and begins improvising promises that Jess and Wyst may not be able to keep. This makes him frustrating at times, especially because his performance benefits from the very gender bias that has hurt Jess.

He receives respect, luxury, and credibility simply because he appears to be a man in charge, while Jess, the actual founder, is pushed into the role of assistant.

However, Spencer is not portrayed as selfish or cruel. Beneath his vanity and impulsiveness, he loves Jess and becomes one of the few people who recognizes how much pain she is carrying.

His reaction when Malcolm appears at TechRumble shows his protective side. He notices Jess’s distress and immediately helps her avoid direct confrontation, proving that he understands her fear without needing a long explanation.

His defense of Jess at their mother’s birthday dinner is especially important because it gives her the support she has not received from her parents. Spencer’s character becomes more meaningful as the story develops: he may be unreliable in business situations, but emotionally he is capable of loyalty, courage, and genuine tenderness toward his sister.

Oliver

Oliver is introduced as a charming American assistant, but his character gradually becomes much more than a romantic interest. His first interaction with Jess is awkward and comedic, as he spills coffee on her, but the moment also establishes his warmth and willingness to make amends.

Unlike many men Jess meets in the business world, Oliver does not immediately try to dominate the conversation or dismiss her. He is attentive, curious, and emotionally available, which makes him stand out in a setting filled with ego, performance, and competition.

His attraction to Jess is not only physical; he seems drawn to her intelligence, guardedness, and flashes of humor.

Oliver’s own backstory gives him depth. His father’s death, his abandoned dream of culinary school, and his depression show that he is also a person who has been diverted from the life he wanted.

This creates a strong emotional parallel between him and Jess. Both have been pushed off course by pain, and both are performing roles that do not fully represent who they are.

His cooking, especially the handmade pasta and desserts, reflects his tenderness and his desire to care for people through something personal and creative. Yet Oliver’s relationship with Jess is complicated by her false identity as Violet.

Every moment of closeness carries the possibility of betrayal, not because Jess wants to hurt him, but because she is trapped inside a lie that began as a survival strategy. In the novel, Oliver represents the possibility of intimacy after trauma, but also the risk that truth must eventually interrupt fantasy.

Cecily

Cecily is Jess’s PR and marketing manager, and she brings wit, boldness, and practical energy to Wyst. She is one of the people who understands both the public-facing value of the company and the emotional stakes behind Jess’s work.

Cecily’s personality is sharp and lively, and she often responds to crisis with humor or dramatic confidence. Her joking comment about applying as “Mr. Cole” helps trigger the central deception, but she is not simply reckless.

She understands the unfairness Jess is facing and recognizes that the world of investors often rewards male confidence more than female competence.

Cecily is also important because she gives Jess a kind of chosen-family support that Jess does not consistently receive from her own relatives. When Jess becomes homeless, Cecily quietly takes care of her belongings and brings her into her family townhouse.

This act shows genuine loyalty beneath her polished, socially confident exterior. Cecily is pragmatic about image, networking, clothing, and opportunity, especially when she prepares Jess for the Vienna ball, but she is also emotionally invested in Jess’s success.

Her encouragement for Jess to enjoy her time with Oliver can seem risky because Jess is lying, yet it also comes from wanting Jess to experience pleasure and freedom after so much fear. Cecily’s role in Risky Business is to push Jess forward, sometimes dangerously, but usually with affection and faith in her.

Pacha

Pacha, the developer at Wyst, is a quieter but significant character because he represents the technical backbone of the company. While Jess is the visionary and Cecily manages image and publicity, Pacha is the person who can actually build tools and solve practical problems.

His creation of the voice changer is one of the most important contributions to the deception, and it shows both his technical skill and his willingness to support Jess even when the plan is ethically questionable. He does not dominate the story, but his presence reminds the reader that Wyst is not only an idea; it is a platform that requires real labor, design, and technological execution.

Pacha also functions as part of Jess’s small circle of trust. The fact that Jess turns to him for help shows that she relies on his competence, and his involvement in the scheme suggests loyalty to her and to Wyst’s mission.

At the same time, his role raises questions about complicity. By helping Jess pretend to be “Mr. Cole,” he becomes part of a lie that could damage the company if exposed.

Still, Pacha’s actions are shaped by the same unfair environment that pressures Jess into deception. He is not portrayed as malicious, but as someone caught between professional loyalty, technical problem-solving, and the increasingly unstable consequences of Jess’s choices.

Dr. Bernadette Reid

Dr. Bernadette Reid, often called Dr. Bernie, is a famous mental-health podcaster whose potential partnership with Wyst represents legitimacy, publicity, and financial possibility. Jess desperately wants her as the face of the company because Dr. Bernie’s reputation could transform Wyst from a struggling start-up into a credible platform with public influence.

Dr. Bernie is professional and interested, but she is not naive. She makes it clear that enthusiasm is not enough; she expects proper payment, a real contract, and evidence that Wyst can support the kind of partnership Jess is proposing.

Her character adds pressure to Jess’s situation because she becomes both an opportunity and a test. Jess’s lie that funding is close shows how desperate she is to keep Dr. Bernie interested, but it also deepens the moral danger around Wyst.

Dr. Bernie is important because she represents the world Jess wants to enter: one where women’s mental health, medical advice, and expert support are treated as valuable. Yet Dr. Bernie’s possible partnership with a rival period-pants start-up also shows that good intentions alone do not protect a business.

In the story, she is a figure of credibility and leverage, someone who forces Jess to confront the gap between what Wyst could become and what it can currently afford to be.

Will Salter

Will Salter is one of the clearest examples of casual misogyny and investor arrogance in the book. Jess approaches him hoping for a serious business conversation, but he immediately misreads or reframes the meeting as a date.

His behavior is dismissive, self-centered, and entitled. He orders expensive wine, talks largely about himself, belittles FemTech, and finally reveals that he never had any intention of investing.

His treatment of Jess is humiliating not only because he wastes her time and leaves her with a large bill, but because he embodies the kind of man who assumes women’s professional ambitions are secondary to his own ego.

Will’s recognition of Jess from the Graystone scandal makes him even more threatening. He connects her present entrepreneurial struggle to the past violation that damaged her reputation, reminding her that the world continues to define her through something done to her rather than through her talent.

Although he does not occupy as much space in the story as Malcolm, Will helps establish the hostile environment Jess is navigating. He shows why the accidental “Mr. Cole” application becomes so tempting: Jess has just been reminded that being herself in front of powerful men can lead to dismissal, humiliation, and judgment.

Malcolm Steward

Malcolm Steward is the main antagonist of Jess’s personal past and one of the most damaging figures in the story. He is the ex-colleague who took intimate photos of Jess without proper consent and shared them with others, causing professional, emotional, and reputational harm.

His actions are not presented as a misunderstanding or a private mistake; they are a violation of trust and bodily autonomy. Even after being removed from Graystone, Malcolm continues to hold power over Jess because the institution’s response forced her into silence rather than justice.

The NDA, the shame, and the pressure not to go to the police all allowed his harm to remain alive in her life.

Malcolm’s return at TechRumble turns Jess’s business deception into a personal nightmare. He recognizes her, watches her, and later threatens to expose Wyst unless she publicly retracts her accusation and apologizes.

This demand reveals his cruelty and entitlement. He does not merely want to escape consequences; he wants Jess to participate in her own erasure by declaring him innocent.

Malcolm is frightening because he understands exactly where Jess is vulnerable: her fear of public shame, her fragile company, her hidden identity as Violet, and her dependence on TechRumble’s success. In Risky Business, Malcolm represents the persistence of abuse after the original act has ended, especially when institutions protect reputations instead of victims.

Dominic 

Dominic is the powerful figure behind TechRumble and Odericco Investments. He represents the glamorous, elite world of start-up funding that Jess desperately needs to access.

His competition offers money, visibility, and investor connections, making him indirectly responsible for the environment in which Jess’s deception becomes both possible and dangerous. Dominic’s presence gives TechRumble its prestige, and his comments about the contestants being among the top start-ups briefly give Jess hope that Wyst’s recognition could matter even if the company does not win.

As a character, Dominic is less emotionally intimate than Jess, Oliver, or Spencer, but his importance lies in what he represents. He is connected to capital, reputation, and gatekeeping.

The fact that Oliver works as his assistant also creates a contrast between external success and private dissatisfaction. Dominic’s world looks polished and desirable, but the people inside it are still struggling with grief, insecurity, ambition, and compromise.

For Jess, Dominic’s competition is both a lifeline and a stage on which her lies may be exposed.

Kit

Kit is an assistant from a cybersecurity company whom Jess meets during the speed networking session. Although Kit is a minor character, their presence matters because they briefly offer Jess a moment of normal conversation amid rising panic.

Jess has just spotted Malcolm and is trying to avoid being confronted, so her interaction with Kit functions as a small pause in the tension. Kit represents the wider community of assistants, interns, and overlooked workers orbiting the main TechRumble contestants.

Kit also helps highlight the difference between the visible leaders and the people who support them. Much of the story plays with status: CEOs receive attention, assistants are underestimated, and Jess moves between both roles because of the Violet deception.

Kit belongs to this assistant-level world, where people may be intelligent and observant but are not treated with the same importance as founders and investors. Even in a small role, Kit helps reinforce the book’s interest in hierarchy, performance, and the way professional spaces assign value to people based on titles.

Jess and Spencer’s Parents

Jess and Spencer’s parents are important because they reveal how deeply Jess’s lack of support extends into her family life. At their mother’s birthday dinner, they criticize Jess for involving Spencer in her business and appear to blame her for the continuing “drama” with Malcolm.

Their response is painful because it echoes the larger social failure Jess has already experienced: instead of centering the harm done to her, they focus on inconvenience, embarrassment, and Spencer’s future. This makes Jess feel once again as though she is the problem rather than the person who was wronged.

Their characterization is not built through long individual arcs, but through the emotional effect they have on Jess. They represent respectability, judgment, and the tendency to minimize trauma when it becomes uncomfortable.

Their attitude also makes Spencer’s defense of Jess more powerful. When he calls her brilliant and hardworking, he provides the validation their parents withhold.

Through them, the story shows that healing from public humiliation and violation is harder when even one’s family treats survival as disruption.

Jess’s Mother

Jess’s mother, though seen most clearly through the birthday dinner, functions as part of the family pressure surrounding Jess. Her birthday gathering becomes the setting where Jess’s private pain, professional risk, and family resentment collide.

Rather than offering simple comfort, the family environment intensifies Jess’s sense of being judged. Jess’s mother is therefore connected to the emotional burden of family expectations and the difficulty of being understood by those who should be closest.

Her role also helps expose the contrast between biological family and chosen support. Cecily provides shelter, Spencer provides defense, and the Wyst team provides belief in Jess’s work, while Jess’s mother becomes associated with criticism and emotional distance.

This does not necessarily make her a villain, but it does make her part of the social world that has failed Jess. She reflects the uncomfortable reality that victims are often asked to manage other people’s discomfort rather than receive unconditional support.

Oliver’s Father

Oliver’s father is not directly present in the main action, but his death shapes Oliver’s emotional life. The image of his belongings being cleared into a box is central to Oliver’s explanation of why he once tried to pursue culinary school.

His father’s death confronts him with the fragility of life and pushes him toward a dream that feels authentic and meaningful. However, grief and depression eventually lead him away from that dream and into his role as Dominic’s assistant.

As an absent character, Oliver’s father helps explain Oliver’s sadness, gentleness, and longing for a different future. He is part of the reason Oliver’s cooking matters so much.

Food becomes connected to memory, care, and the life Oliver still wants but has not fully claimed. His father’s influence also deepens Oliver’s bond with Jess because both characters are shaped by painful events that changed the direction of their lives.

Through Oliver’s father, the story gives Oliver a private grief that makes him more than a charming romantic figure.

Themes

Gender Bias and the Cost of Being Underestimated

Jess’s struggle begins in a business world that repeatedly treats women’s health as less serious, less profitable, and less worthy of attention. Her meeting with Will exposes this clearly: he dismisses FemTech, misunderstands a professional meeting as romantic, and assumes his own importance matters more than her pitch.

The accidental “Mr. Cole” application becomes a sharp comment on how differently the same idea is received when it appears to come from a man. Spencer receives respect, comfort, and attention as the supposed CEO, while Jess, posing as Violet, is treated as secondary even though Wyst is her creation.

Risky Business uses this deception not just for comedy, but to reveal a painful truth: Jess is not pretending because she lacks talent; she is pretending because the system has trained her to believe talent alone may not be enough when it comes from a woman. The theme shows how bias can force capable people into impossible choices between honesty and survival.

Shame, Trauma, and the Fight to Reclaim Control

Jess’s past with Malcolm continues to shape her present, not because she is weak, but because the damage done to her was never properly repaired. The intimate photos taken and shared without consent destroyed her sense of safety at work, while Graystone’s pressure to sign an NDA deepened the injustice by protecting the company more than the victim.

Her panic when she sees Malcolm shows how trauma can return suddenly, even in moments of professional success. She vomits, flees, lies about her identity, and struggles to trust her own future because Malcolm still holds power over the story.

Yet Jess’s refusal to retract the truth marks an important turning point. She may still be frightened, but she is no longer willing to help him rewrite what happened.

The theme is powerful because it presents recovery as uneven and difficult. Jess does not become fearless overnight; instead, she slowly begins to understand that shame belongs to the person who harmed her, not to her.

Ambition, Deception, and Moral Pressure

Jess’s lies grow out of desperation rather than cruelty, which makes her choices complicated. Wyst is close to failure, her finances are collapsing, and the chance offered by TechRumble feels like the only route left.

Once the “Mr. Cole” mistake opens a door, she chooses to keep walking through it, even though every step makes the deception harder to control. She exaggerates Wyst’s size, claims Dr. Bernie is involved, hides behind a voice changer, uses Spencer as a false CEO, and presents herself as Violet.

The tension comes from the fact that her ambition is tied to a genuinely useful mission: she wants women to have access to trusted health support. Still, the lie begins to threaten the very thing she is trying to protect.

Spencer’s improvised promises, Malcolm’s blackmail, and her growing feelings for Oliver all show how one dishonest choice can create emotional and professional pressure. The theme asks whether survival in an unfair world excuses deception, while also showing why Jess felt cornered into it.

Identity, Love, and the Need to Be Seen Honestly

Jess’s relationship with Oliver matters because it offers her a version of herself beyond crisis, performance, and fear. With him, she laughs, drinks, talks, flirts, and briefly feels like a person rather than a founder fighting for survival or a woman hiding from scandal.

Yet their connection is built while she is using the name Violet, which makes the comfort fragile. Oliver sees parts of her that are real: her humor, intelligence, warmth, and vulnerability.

At the same time, he does not know the full truth of who she is or what she is risking. This creates deep guilt, especially when intimacy becomes more serious and the false name feels unbearable.

His own grief also mirrors Jess’s pain, since both characters have been shaped by loss and disappointment. In Risky Business, love is not treated as a simple escape from conflict.

Instead, it becomes a test of whether Jess can stop hiding, tell the truth, and allow someone to know her without disguise.