Long Strange Trip: CEO to CEO with Brian Halligan Parker Conrad’s Revenge Fantasy
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Nov 13, 2025 
Parker Conrad, founder and CEO of Rippling and former Zenefits leader, shares his journey from a public ousting to building a $17 billion enterprise. He discusses how revenge fueled his motivation and offers candid advice for founders, emphasizing the importance of operational speed and hiring mentality. Parker reflects on navigating capital raising after criticism and delves into a dramatic dispute with competitor Deel, revealing their investigative tactics. With insights on leadership and hiring philosophies, he tears up traditional CEO playbooks.
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Revenge Fueled The Startup's Early Years
- Rippling began as Parker Conrad's "revenge fantasy" after his exit from Zenefits and that drive fueled the early years.
- Over time the motivation softened into excitement about product, people, and customer impact.
Think Twice Before Starting A Company
- Don't start a startup lightly; Parker warns it's soul-crushing and far harder than people expect.
- He recommends avoiding entrepreneurship if you have other viable options because of the human cost.
CEO Should Go See The Coalface
- Parker rejects the top-down CEO-as-delegator model and practices hands-on problem solving himself.
- He calls this leadership principle "go and see" to stay grounded in operational reality.