San Francisco | April 9, 2025 — What began as a love story between two brilliant minds from India has now devolved into a bitter transcontinental legal battle, loaded with serious allegations, emotional trauma, and intense public scrutiny.
Prasanna Sankar, a Chennai-born tech entrepreneur and co-founder of the $13 billion U.S.-based startup Rippling, and his wife, Dhivya Shashidhar, are at the heart of a deeply personal crisis that has gone public—with damning accusations on both sides and a child caught in the middle.
A Promising Beginning, A Sudden Descent
Their journey began in 2007 at NIT Trichy, where Dhivya stood out as a top student and Prasanna was already making waves in the programming world. From young love in India to ambitious careers abroad—Dhivya at University of Cambridge, Prasanna in Silicon Valley—their lives seemed like a modern fairytale.
In 2013, the couple tied the knot, seemingly ready to take on the world together. Prasanna joined Zenefits, which quickly became a Silicon Valley darling before facing major regulatory setbacks. Undeterred, the duo founded Rippling in 2017, which soared to unicorn status. But behind the scenes, cracks were forming.
Allegations of Control, Abuse, and Isolation
In a tell-all interview with The San Francisco Standard, Dhivya painted a picture of life behind closed doors—describing her marriage as “the worst nightmare of my life.”
She alleged that Sankar emotionally abused her, coerced her into an open marriage, and frequented escorts, all while pushing her to relocate from one country to another to serve his financial interests—primarily tax avoidance, she claims.
Their frequent relocations—from California to Washington, and later to Singapore—left Dhivya feeling trapped. She had renounced her Indian citizenship to become a U.S. citizen, banking on building a future there with their son, born in 2016.
Life in Singapore: Dependency and Despair
The shift to Singapore marked a turning point. Dhivya lost her job at Microsoft and, bound by a dependent visa, couldn’t work again. With no financial autonomy, she testified that Sankar told her she had “no right to his wealth.”
Emotionally and economically isolated, she claimed Prasanna embraced a lifestyle of “frivolous sexual behaviors,” allegedly pressuring her to engage in intimacy with his acquaintances—a claim she described as deeply traumatic and violating.
Affair or Fabrication? Both Sides Speak Out
In a retaliatory move, Prasanna took to social media, accusing Dhivya of having an extramarital affair with a man named Anoop Kuttysankaran. He posted what he claimed were screenshots of intimate messages, including one referencing extra-large condoms.
Dhivya, however, vehemently denied the authenticity of the messages, calling them fabricated and accusing Prasanna of digital manipulation to discredit her.
The Legal Storm
Amid the personal chaos, the legal battle now centers on custody of their child. Reports indicate that the couple signed a Memorandum of Understanding, where Prasanna agreed to:
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Pay ₹9 crore as a settlement,
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Provide ₹4.3 lakh per month in child support,
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Share 50-50 custody of their son.
But the courtroom drama is far from over.
Sankar has alleged that law enforcement is illegally surveilling him—tracking his phone, car, UPI transactions, and IP logs—despite no official FIR being filed. He attributes this to false cases filed during the custody conflict.
Who Is Prasanna Sankar?
Prasanna Sankaranarayanan, widely known as Prasanna Sankar, is a trailblazing entrepreneur from Chennai. A graduate of NIT Trichy, he quickly rose in the tech ranks, first with a short-lived startup called Likealittle, then through his tenure at Zenefits, and finally with Rippling, his most successful venture to date.
Today, Rippling is valued at approximately $13 billion, offering a unified platform for managing HR, IT, and finance functions for businesses. But despite his business triumphs, Sankar now finds his reputation tested like never before.
A Cautionary Tale Behind Silicon Valley’s Success Stories
This unfolding saga serves as a sobering reminder that even the most celebrated startup founders can be embroiled in intense personal crises. The tech world often celebrates innovation, grit, and scale—but rarely the human cost that lies beneath.
For Dhivya Shashidhar, the journey from Cambridge scholar to stay-at-home mother in a foreign country ended in a very public fight for dignity and justice. For Prasanna Sankar, the brilliant coder who once dreamt of reshaping workplace software, the challenge ahead may no longer be technological—but deeply personal.
