Set against Silicon Valley's dot-com boom and bust from 1999 to 2002, the novel follows two sisters whose contrasting temperaments lead them through love, ambition, and loss during one of the most volatile periods in recent American history.
Emily Bach, a disciplined 28-year-old, is the CEO of Veritech, a data-storage start-up in Mountain View, California, preparing for its initial public offering (IPO). Her younger sister Jess, 23, is an idealistic philosophy graduate student at UC Berkeley who works part-time at Yorick's, a rare-book store run by George Friedman, a reclusive Microsoft millionaire in his late thirties. Where Emily is pragmatic and driven, Jess is whimsical and antimaterialistic. Their mother, Gillian, died of breast cancer when Emily was 10 and Jess was 5, leaving behind sealed birthday letters that the sisters open each year, urging them toward independence and purpose.
Emily offers Jess the chance to buy 100 shares of Veritech at $18 each through a Friends and Family offering, but Jess lacks the $1,800. Unable to ask their father, Richard, a computer scientist at MIT with whom she has a strained relationship, Jess borrows the money from Rabbi Nachum Helfgott, the gregarious Hasidic rabbi of the Bialystok Center of Berkeley, a congregation with roots in the Polish city of Białystok. The rabbi, who is also an enthusiastic day trader, asks only that Jess repay the loan when she can.
At Veritech, Emily manages Alex Zaslovsky, her brilliant 22-year-old chief technology officer, who has developed a concept called electronic fingerprinting: a covert surveillance tool that tracks every user's interaction with stored data. Emily sees ethical problems with the concept and plans to redirect Alex's work toward a less invasive password-authentication system. When Veritech goes public in November 1999, the stock soars past $100 a share, making Emily a paper multimillionaire.
Emily's boyfriend, Jonathan Tilghman, is the co-founder of ISIS, an Internet security company in Cambridge, Massachusetts. A former Marine from Nebraska, Jonathan is fiercely competitive. Over Thanksgiving, Emily visits him in Cambridge, where they dine with Orion Steiner, another ISIS co-founder and Emily's childhood friend. Orion reveals he has broken Lockbox, ISIS's flagship security product, exposing structural flaws that Jonathan dismisses. That night, in a moment of vulnerability, Emily whispers the details of Veritech's secret fingerprinting project to Jonathan, asking him to confide something in return. He lies about Lockbox's problems.
Meanwhile, Jess becomes romantically involved with Leon, the charismatic older founder of Save the Trees, an environmental activist group in Berkeley. She moves into the group's communal house, donates her Veritech shares to the cause, and splits her time between activism, graduate school, and the bookstore.
George begins courting a remarkable find: an extensive collection of rare cookbooks inherited by Sandra McClintock from her uncle Tom McClintock, a retired lichenologist who stored the volumes in his kitchen cabinets and oven. The books are interleaved with the collector's erotic drawings, literary quotations, and imaginary menus devoted to a mysterious unnamed woman. When Sandra, guilt-ridden about breaking a deathbed promise to keep the collection together, retreats in distress during the appraisal, Jess connects with her through shared experience of maternal loss and learns Sandra needs money for her daughter's custody battle. Sandra agrees to sell to George for just under half a million dollars.
As the market declines, Jonathan proposes to Emily, and the couple becomes engaged. Alex confronts Emily after she rejects his surveillance project and leaves Veritech. Emily calls Jonathan, who is secretly delighted, seeing an opportunity to develop the concept himself. Months later, at an ISIS executive meeting, Jonathan presents electronic fingerprinting as his own invention, rebranding it as Fast-Tracking. Orion, unaware of the idea's origins, volunteers to lead the new team.
George installs the collection in his home and hires Jess as its curator. Working alone each afternoon, Jess becomes absorbed in the cookbooks and the collector's notes. George, long infatuated with Jess, leaves a ripe peach on the kitchen table for her. Over three days she watches it ripen, and when she finally eats it, George comes home to find her. Wine and dinner lead to their first kiss, and a secret affair begins.
Jess decodes an acrostic menu in the collection that spells the name Janet, confirming that Tom McClintock was in love with his sister-in-law. George later doubles his payment for the collection based on the discovery's significance.
The contradictions in Jess's life reach a breaking point. She feels ashamed of her dependence on George's wealth, and Leon accuses her of being seduced by his patronage. When George excludes her from a dinner party and tries to prevent her from joining a tree-sitting expedition, Jess accuses him of treating her as a possession and storms out. She climbs Galadriel, a 2,000-year-old redwood, to overcome her fear of heights. After two days on a platform 150 feet up, a massive branch crashes during a storm, triggering a panic attack. George, who has driven up from Berkeley, is waiting at the base when she descends. Furious, Jess drives away, but George follows her for hours to a redwood park called Fern Hollow, where he proposes on a fallen tree bridging a stream. After resistance, Jess says yes. They camp that night in the forest. It is September 10, 2001.
The next morning, Jonathan and Mel Millstein, ISIS's HR director who lives near the Bach family in Canaan, Massachusetts, are both aboard American Airlines Flight 11, which crashes into the World Trade Center. Jonathan had been flying to a job fair; Mel had reluctantly agreed to attend at Jonathan's insistence. Emily hears the news on the radio and retreats to bed for days. Jess rushes to her side, arriving at Emily's condo wearing the Vivienne Tam suit Emily gave her years ago, signaling that she has come to take care of her sister.
At Jonathan's memorial service at MIT, Dave, the CEO of ISIS, eulogizes Jonathan and reveals that Fast-Tracking is being developed as a surveillance system. Emily realizes Jonathan stole her confidence about electronic fingerprinting and built ISIS's new product from it. At the same service, Chaya Zylberfenig, a member of the Bialystok community, approaches Jess with a revelation: Their mother Gillian was actually Gittel Gould, the oldest of nine children in a Bialystoker Hasidic family in London who ran away from home. Gillian was declared dead by her parents when she married the non-Jewish Richard. Jess confronts her father, who confirms Gillian asked him never to reveal her origins.
In the aftermath, Emily resigns from Veritech, recognizing that she herself betrayed Alex by sharing his idea with Jonathan. She travels to London to meet her mother's Hasidic relatives and returns to launch Geno.type, a social-networking start-up designed to reconnect lost families. She donates Jonathan's engagement ring to establish a breast cancer research fund in her mother's birth name. Orion leaves ISIS after the company pivots to government surveillance contracts and goes to Sorel Fisher, an English programmer with whom he has shared a deepening connection.
Jess returns to George and resumes her scholarly work on the cookbook collection. In May 2002, George and Jess marry in the Berkeley Rose Garden under a white canopy, with Rabbi Helfgott officiating and Emily and Richard giving Jess away. The novel closes with the newlyweds lying together in a hammock in the garden, floating between joy and the knowledge that nothing lasts, holding each other all the same.