#43: Success Won’t Fix You (What a $4B CEO Learned Too Late)

#43: Success Won’t Fix You (What a $4B CEO Learned Too Late)

From Divot by Derek Andersen

April 1, 2026 · 1h 8m · Season 2 · Episode 27

About this episode

Adam Edmunds shares his journey to becoming a CEO and the lessons learned about success and self-worth.

Before leading a $4B company, Adam Edmunds spent years trying to prove he was good enough. From cold emailing CEOs as a student to building his first company, his journey started with uncertainty and a relentless need for validation. In this conversation with Derek Andersen, Adam shares how he became CEO of Entrata, a platform powering over 20,000 apartment communities worldwide, raising $700M+ and reaching a $4B+ valuation. He breaks down what it really takes to scale a company at that level. Adam explains why relationships are the most valuable currency in business, how great leaders recruit over years, not weeks, and why reputation determines the ceiling of your success. He also shares hard lessons on hiring, culture, and long-term thinking. The episode goes deeper into identity, failure, and self-worth, why success doesn’t fix how you feel about yourself, and how learning to stop seeking external validation changed everything about how he leads and lives. Follow Adam - X (Twitter): https://x.com/adamedmunds Follow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners: Google for Startups Everything you need to build and scale AI agents, from tools to expert…

People in this episode

Host: Derek Andersen

Guest: Adam Edmunds

Topics covered

Sponsors

Google for Startups, Pulley

Mentioned in this episode

Organizations: Entrata

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