This Is The Most Exciting Drama in HR SaaS History | Rippling vs. Deel

About this video

Sam and Shaan explore corporate espionage through the lens of a lawsuit where Rippling alleges that their competitor Deal stole trade secrets using an insider. They discuss Rippling’s clever honeypot trap and then dive into historical and modern examples of corporate espionage, including the British East India Company’s theft of tea production secrets from China, Oracle’s dumpster-diving investigation of Microsoft, and the Uber-Waymo case. They also examine the exceptional growth story of cybersecurity company Wiz, which sold for $32 billion in 5 years by leveraging a powerful network of CISOs and a proven playbook for building enterprise software companies.

Key takeaways

• Rippling allegedly caught a Deal insider snooping by creating a fake Slack channel as a honeypot; the accused allegedly flushed his phone down a bathroom toilet when confronted—illustrating both the lengths companies go to catch espionage and the legal jeopardy of destroying evidence.
• Historical corporate espionage often had nation-state consequences: Robert Fortune disguised himself as a Chinese merchant to steal tea seeds and knowhow from China for the British East India Company, breaking China’s monopoly and preventing further Opium Wars.
• Gilly’s Cyber Starts fund achieves 100%+ IRR and five unicorns out of 22 companies by leveraging a closed network of CISOs at Fortune 500 companies who identify problems, invest in solutions, and become first customers—demonstrating the power of insular, trust-based networks to compound returns.
• Wiz grew from zero to $32 billion valuation in 5 years by raising aggressively upfront, hiring top talent, and using calendar density of sales reps as the only reliable leading indicator for headcount growth—showing that venture-backed scale and bootstrap stress are roughly equal despite vastly different outcomes.
• The stress and time commitment of building a business is roughly constant (10-12 hours daily) regardless of revenue or valuation; the real choice is whether to tackle a $1M ARR problem or a $500M+ ARR problem with the same effort.

Episode details: published March 21, 2025 · 27K views · 58:59 long. Summary written by Self Growth Videos from the episode itself. The business ideas, figures and results discussed are the hosts’ and guests’ own claims, shared as brainstorming and entertainment — not verified facts and not investment advice.

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