As a three-time founder, Parker Conrad has one piece of advice for aspiring entrepreneurs—don’t do it. The Rippling co-founder and CEO joins Sarah Guo to talk about what he learned from the crash at Zenefits, why most advice to founders is wrong, and how building a real platform—not a point solution—is the only way to win in SaaS. The two get into founder psychology, the myth of learning from failure, and what true ownership looks like inside a company. He also shares why AI won’t shrink teams anytime soon, what people misunderstand about vertical software, and why ambition trumps efficiency with long-lasting companies.

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Chapters:

00:00 Introduction to Parker Conrad

00:33 Lessons from Zenefits to Rippling

01:54 The Psychology of Founding a Company

07:56 Rippling's Ambitious Vision

10:41 Building a Platform Company

15:05 Challenges and Strategies in Scaling

30:36 AI's Impact on Software Development

42:06 Public vs. Private: Rippling's Future

44:19 Conclusion