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 involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC. *APY as of 6/30/25, offered by Public Investing, member FINRA/SIPC. Rate subject to change. See terms of IRA Match Program here: public.com/disclosures/ira-match. Learn more about your ad choices. Visit megaphone.fm/adchoices