In the world of billion-dollar startups, competition is expected. But what happened between Rippling and Deel isn’t just a rivalry—it’s one of the most explosive scandals Silicon Valley has ever seen.
It starts with a spy. A mid-level employee inside Rippling who—according to a sworn affidavit—ran over 6,500 secret Slack searches, funneled confidential data to a competitor, and got paid just $6,000 in crypto to do it. But that’s only the beginning.
As the case unfolded, Deel’s top executives vanished to Dubai. Rippling’s co-founder became entangled in a very public custody battle filled with allegations of surveillance and abuse. And suddenly, a lawsuit that started as corporate espionage morphed into something bigger: a full-blown indictment of how Silicon Valley operates behind closed doors.
This is the story of how two of the fastest-growing startups in tech turned to spying, secrecy, and scandal to win. But it’s also a story about power—how we idolize founders, excuse bad behavior, and fund myth over merit.
Welcome back to Tech Unmasked, a series where I dig into the biggest stories in tech and expose what’s really happening behind the scenes.
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Timestamps:
00:00 – Intro
01:58 – Chapter 1 : The Spy Speaks
05:18 – Chapter 2 : The Dubai Escape
07:28 – Sponsor Shoutout (ad)
08:30 – Chapter 3 : The Divorce Goes Public
10:38 – Chapter 4 : What All It Means For Tech
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Resources:
https://techcrunch.com/2025/04/15/deels-ceo-is-now-in-dubai-complicating-ripplings-lawsuit/
https://techcrunch.com/2025/03/17/rippling-sues-deel-deel-denies-all-legal-wrongdoing-and-slack-is-the-main-witness/
https://techcrunch.com/2025/04/14/rippling-is-trying-to-serve-deels-ceo-but-bailiffs-cant-find-him/
https://techcrunch.com/2025/04/02/the-affidavit-of-a-rippling-employee-caught-spying-for-deel-reads-like-a-movie/
https://www.documentcloud.org/documents/25877605-stamped-affidavit-of-keith-obrien-1-april-2025-redacted/?mode=document#document/p1
https://www.irishtimes.com/crime-law/courts/2025/04/10/rippling-spy-who-destroyed-phone-with-axe-avoids-court-sanction/
https://sfstandard.com/2025/04/04/rippling-prasanna-sankar-wife-viral-custody-battle/
https://x.com/myprasanna/status/1903808742866763904
https://x.com/myprasanna/status/1903808742866763904
https://www.barandbench.com/news/litigation/prasanna-case-madras-high-court-issues-guidelines-to-curb-police-harassment-during-probe
https://timesofindia.indiatimes.com/technology/tech-news/wife-of-ripplings-billionaire-co-founder-prasanna-sankar-hits-back-accuses-him-of-forcing-open-marriage-/articleshow/120061703.cms
https://news.ycombinator.com/item?id=43388133
https://news.bloomberglaw.com/litigation/rippling-sues-hr-software-rival-deel-for-trade-secret-theft
https://x.com/jsawadd/status/1901627992700264527
https://www.inc.com/jennifer-conrad/payroll-startup-deel-files-to-dismiss-baseless-rico-suit/91136751
https://rippling2.imgix.net/Complaint.pdf
https://www.semafor.com/article/01/24/2025/payroll-platform-deel-denies-charges-that-it-enabled-money-laundering-blames-competitor-for-lawsuit
https://techcrunch.com/2025/03/17/rippling-sues-deel-deel-denies-all-legal-wrongdoing-and-slack-is-the-main-witness/
Disclosure:
Some of the above links are affiliate links. Using these links is one of the best ways to support me at no cost to you! All views expressed in this video are entirely my own and do not represent the opinions of my employer or any associated organization.
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