As of March 25, 2025, Prasanna Shankar, co-founder of the $10 billion HR-tech giant Rippling, finds himself at the center of a dramatic personal and legal storm. The Chennai-born tech entrepreneur has taken to social media to allege harassment by his estranged wife, Dhivya Sashidhar, and the Chennai police amid a bitter divorce and child custody dispute over their nine-year-old son. In a series of explosive posts on X starting March 23, Sankar claims he is “on the run” from authorities, accusing them of extortion and illegal tracking, while countering his wife’s allegations with evidence of her infidelity. This unfolding saga has captivated the internet, raising questions about his illustrious career, personal life, and the messy clash now playing out in public.
Prasanna Shankar (full name Prasanna Shankara narayanan) is an Indian-origin entrepreneur whose journey from Chennai to Silicon Valley epitomizes tech-world success. Born and raised in Tamil Nadu, Shankar graduated with a Bachelor’s degree in Computer Science from the National Institute of Technology (NIT) Trichy, where he met Dhivya, his wife of 10 years. A prodigious coder, he earned the rank of India’s #1 programmer on TopCoder and was a two-time finalist in Google Code Jam and ACM ICPC, per his LinkedIn profile. After stints at Google (2006 internship) and Microsoft Canada, Sankar co-founded Rippling in 2016 with Parker Conrad.
Rippling, a workforce management platform integrating HR, IT, and finance, skyrocketed to a $10 billion valuation, cementing Sankar’s status as a tech titan. He served as CTO until 2020, leaving to launch 0xPPL, a Singapore-based crypto social network, in 2023. Now based in Singapore, his net worth is estimated at $1 billion (Forbes), bolstered by Rippling’s success and real estate holdings in Chennai.
Shankar’s personal life took a tumultuous turn when, in late 2024, he discovered Dhivya’s alleged six-month affair with Anoop Kuttysankaran, a claim backed by screenshots from Anoop’s wife shared on X on March 23. Their 10-year marriage, which produced a son, Amar, crumbled as divorce proceedings ensued—Shankar filing in India, Dhivya in the U.S., allegedly for a larger settlement. The dispute escalated when Shankar accused Dhivya of abducting Amar to the U.S., prompting him to file an international child abduction case. A U.S. court ruled in his favor, ordering Amar’s return to India, per Shankar’s posts.
The couple signed a Memorandum of Understanding (MoU) in Chennai, agreeing to a ₹9 crore settlement, ₹4.3 lakh monthly child support, and 50-50 custody, with Amar’s passport to be held in a shared locker. But tensions flared when Dhivya allegedly reneged, claiming the MoU was invalid and threatening to refile in the U.S. Shankar sought court enforcement, only for Dhivya to file a kidnapping complaint against him in Chennai on March 9, after his assistant Gokul took Amar from her on March 11.
Shankar’s narrative took a darker turn on March 23, when he posted on X that Chennai police were harassing him and his associates. He claims officers raided his hotel on March 11, forcing him to flee with Amar, and later targeted his mother’s home and friend Gokul, detaining the latter without an FIR. Shankar alleges the Thirumangalam police demanded ₹25 lakh to release Gokul, tracked his phone, UPI payments, and IP address illegally, and raided an Airbnb he’d vacated. “The AC and SI have asked me for 25L to release my friend,” he tweeted, tagging Tamil Nadu’s CM and PMO.
He insists Amar was handed over voluntarily—sharing WhatsApp messages from Dhivya agreeing to a pickup on March 11—and provided police with proof of his son’s safety via video call. Yet, he alleges authorities persisted, pressuring Gokul to discredit his social media claims. On March 25, Shankar updated X, stating the Chennai Police Commissioner assured no arrests, allowing Gokul’s release and his father’s return home, though investigations into the kidnapping claim continue.
Dhivya Sashidhar paints a starkly different picture. In a video statement on March 23, reported by News18, she accused Shankar of luring her and Amar (both U.S. citizens) to India three weeks prior under a property dispute pretext, only for Gokul to forcibly take Amar. “I don’t know the whereabouts of my son,” she said, filing her complaint at Thirumangalam station. She brands Shankar a “sexual predator,” alleging he secretly recorded women and assaulted her in Singapore—charges he says were dismissed by Singapore police. Dhivya further claims Shankar transferred matrimonial assets to his father and brother in Thailand to evade taxes, pressuring her to sign away her rights to report it.
Chennai police have denied Shankar’s allegations of bribery and harassment, calling them “baseless” and asserting they’re investigating her legitimate complaint, per DT Next on March 23. The dispute’s public airing has sparked a polarized X response, with some decrying alleged police overreach and others questioning Sankar’s narrative.
Shankar’s saga, amassing over 8.6 million X views by March 25, blends personal vendetta with systemic critique. His March 24 pledge to file a “don’t harass” petition reflects defiance: “I built an empire from nothing. I can handle this,” he wrote on X. The case spotlights India’s legal and police dynamics in high-profile disputes, echoing broader debates on custody laws and gender bias—some X users lament “men’s rights” erosion, per India Today.
For Rippling, the controversy casts a shadow over its brand, though Shankar’s 2020 exit limits direct impact. His pivot to 0xPPL and the crypto space ties this drama to Web3’s ethos of autonomy, contrasting with the state pursuit he describes. As courts take up custody, the March 25 resolution with police offers temporary peace, but the legal war with Dhivya looms large.