Indian tech billionaire's wife alleges husband forced her to open marriage amid custody battle

In an explosive interview, NIT graduate-turned-tech-tycoon Prasanna Sankar’s wife, Dhivya Shasidhar, spilled the beans on her estranged husband. In a dramatic tale unfolding across borders and legal systems, the cofounder of Rippling—a San Francisco-based workforce management company valued at $13 billion—has alleged that his wife not only had an affair but also kidnapped their only child.

In a tell-all interview with The San Francisco Standard, Dhivya alleged that her husband subjected her to mental abuse, visited several escorts, and forced her into an open marriage. She also claimed he dragged her and their son from country to country to evade taxes.

She described her marriage to Sankar as the “worst nightmare of my life.”

A Promising Beginning

Sashidhar and Sankar first crossed paths in 2007. Two years later, their friendship blossomed into a romantic relationship. At their university in Tiruchirappalli, India, Sashidhar stood out as the top academic performer, while Sankar made a name for himself in the tech world, earning the number one spot in a national programming competition at just 18.

Ambition on Different Continents

Despite the distance, the couple kept their relationship alive. Sankar moved to Silicon Valley to pursue his entrepreneurial dreams, while Sashidhar was awarded a prestigious scholarship to study at the University of Cambridge. During this period, Sankar launched Likealittle, a social platform encouraging anonymous flirting among college students. He raised $7 million in funding, but the venture failed to take off.

Marriage and New Chapters

In 2013, after years of balancing long-distance love and demanding careers, the couple tied the knot. Two years later, Sankar returned to San Francisco to join Zenefits, a fast-rising healthcare software startup founded by Parker Conrad. He was hired as director of engineering. The company soared to a $4.5 billion valuation—until scandal struck.

Corporate Collapse and Reinvention

Zenefits was soon embroiled in controversy. In 2017, the Securities and Exchange Commission found that the company had misled investors. Prior to that, media reports exposed a chaotic and inappropriate office environment, including accounts of employees engaging in sexual activity in stairwells. Amid the fallout, Conrad stepped down. Sankar also left the company.

Undeterred, Sankar and Sashidhar partnered on a new venture. In early 2017, they entered Y Combinator with their startup, Rippling—an all-in-one platform designed to manage HR, devices, and finances for businesses. While Sankar would later describe building Rippling as a “magical” experience, the personal story behind the scenes was far more complicated.

A Troubled Home Life

Their son was born in 2016, marking a major life change for both. But according to court documents, Sashidhar felt isolated and unsupported in the United States. She testified that Sankar was emotionally distant and inattentive, both as a husband and as a father.

“He would come back home and sit with his laptop,” she recalled. “We had very limited time together.”

Intimacy and Allegations

In her testimony, Sashidhar also made disturbing allegations about Sankar’s behavior behind closed doors. Despite her ongoing pain from childbirth complications, she claimed that he persistently pressured her for sex, showing little regard for her physical condition or emotional well-being.

In 2020, Sankar proposed relocating to Washington state. According to Sashidhar’s court testimony, his motivation was financial—he anticipated his significant equity in Rippling would soon vest and wanted to avoid paying California’s high income taxes.

Although Sashidhar was reluctant to leave, she felt pressured and ultimately went along with the move, believing she had little say in the decision.

As their two-year stint in Washington drew to a close, Sankar introduced yet another major change—this time suggesting they relocate to Singapore.

A Reluctant Departure

Sashidhar was strongly opposed to another move—especially overseas. She had already made a profound sacrifice by renouncing her Indian citizenship to pursue U.S. citizenship, a step necessary since India does not permit dual nationality. Her decision was rooted in a shared vision: settling in the United States for good and raising their son there, with hopes of one day seeing him attend an elite university like Stanford or Harvard.

Despite her objections, Sankar reassured her that the relocation to Singapore would be temporary and motivated solely by his desire to reduce their U.S. tax obligations.

Life in Singapore: Isolation and Dependency

The reality of life in Singapore quickly unraveled for Sashidhar. Shortly after the move, she was laid off from her role at Microsoft. Due to her dependent visa status—tied to Sankar’s tech worker visa—she was legally barred from seeking new employment.

Meanwhile, Sankar testified that he was involved with a crypto startup, officially registered in the Cayman Islands and operationally linked to India. This setup further complicated their financial situation—and their marriage.

Financial Disputes and Emotional Strain

According to Sashidhar’s testimony, Sankar’s attitude toward her shifted sharply. Despite earlier discussions that had led her to believe they shared financial security, he began telling her she was entitled to none of his wealth. As she cared for their son full-time, she found herself increasingly shut out—emotionally, financially, and legally vulnerable in a foreign country.

A Descent into Darkness

Sashidhar claimed that during this period, Sankar immersed himself in a social circle that embraced excess and indulgence. In court, she described his lifestyle as one steeped in “frivolous sexual behaviors with many partners/prostitutes.” She further alleged that he pressured her to sleep with some of his acquaintances—a suggestion she found deeply traumatic.

Her rejection of these advances, she testified, left her feeling “scared,” “violated,” and “destroyed.”

In a series of posts on X (formerly Twitter), Sankar claimed that during this turbulent period, he discovered that Sashidhar was having an affair with a man named Anoop Kuttysankaran. To support his allegation, he shared screenshots of what he said were text messages exchanged between Sashidhar and Kuttysankaran—one of which appeared to show her requesting extra-large condoms.

Sashidhar, however, strongly denied the authenticity of the messages. In an interview with The Standard, she stated her belief that the screenshots were fabricated.

Amid the accusations, emotional fallout, and public scrutiny, the couple is now locked in a legal battle over the custody of their son. What began as a partnership marked by shared ambitions has devolved into a deeply contentious and high-stakes courtroom fight for parental rights.

As per reports, and Dhivya Shashidhar signed an MoU, with Prasanna agreeing to pay ?9 crore and ?4.3 lakh monthly in support. They agreed on 50-50 custody of their son. Sankar alleged police have been illegally tracking his phone, car, UPI, and IP data despite no FIR, due to false cases.

Who Is Prasanna Sankar?

Prasanna Sankaranarayanan, popularly known as Prasanna Sankar, is a Singapore-based entrepreneur of Indian origin. He hails from Chennai, Tamil Nadu, and pursued his undergraduate studies in computer science at the prestigious National Institute of Technology (NIT) Trichy. It was during his time there that he met his future wife.

Sankar has made a significant mark in the global tech ecosystem as the co-founder of Rippling, a leading workforce management platform. The company, which streamlines HR and IT operations for businesses, has reached an impressive valuation of around $10 billion. Before co-founding Rippling, Sankar held key roles in several tech ventures, building a reputation for innovation and leadership in the startup world.