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
