Inside Rippling vs. Deel’s Billion-Dollar Espionage War

What happens when a unicorn startup hires a spy to infiltrate its
biggest rival? Welcome to the $28 billion battle between Rippling
and Deel—where encrypted messages, crypto payments, burner phones,
and a secret escape to Dubai are all part of the plot. Today, Sammi
unpacks the real-life espionage scandal playing out in Silicon
Valley. At the center: two HR tech giants locked in a legal death
match. One allegedly planted a spy inside the other. And not just
any spy—a payroll exec turned corporate James Bond, allegedly paid
thousands a month to leak sensitive data from Slack, Salesforce,
and more. This story has everything: honeypots, family
conspiracies, a phone destroyed with an axe, and RICO charges
straight out of a mob movie. And it’s all unfolding right now.
Whether you’re a founder, a tech worker, or just here for the
tea—this episode is a front-row seat to the dark side of startup
competition. Follow Sammi on Instagram  Subscribe to the
Social Currency newsletter  Here’s what Sammi covers today:
00:00 The Spy Thriller Silicon Valley Didn’t See Coming 00:48 Meet
the Rivals: Rippling vs. Deel 02:16 The “Snake Oil” Feud Gets
Personal 04:13 Enter the Spy: Keith O’Brien’s Double Life 06:20
Crypto, Code Names, and the Watchman 08:31 How the Spy Got Caught
(and Things Hit the Fan) 11:06 The Honeypot Trap and a Shocking
Confession 13:45 Destroyed Phones and Dubai Getaways 15:52 The
Lawsuit: RICO, Racketeering, and Corporate Crime 18:33 Deal Fires
Back and the Legal War Escalates 20:10 Why the Market Doesn’t Seem
to Care 22:05 What This Means for Startup Culture All investing
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