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.

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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

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