In this episode, Justin Bauer, former Chief Product Officer at Amplitude and now one of the most sought-after product advisors in AI, talks about the pivotal career moments that shaped his leadership style. From betting everything on a tiny startup with 13 people to navigating layoffs and leveling conversations, Justin shares how he learned to lead with clarity, humility, and courage.

He also reflects on what it takes to thrive in a high-growth environment — and how to reinvent yourself every 18 months to stay relevant. This is a conversation about ambition, emotional resilience, and how to earn trust when the stakes are high.

In this conversation, you’ll learn:

• Why preparation and self-reflection are Justin’s keys to confident leadership
• How to navigate the emotional toll of layoffs, leveling, and managing up
• Why clarity of expectations keeps your career evolving

Things to listen for:

(00:00 ) Intro

(01:44 ) Justin's early life in Iowa

(04:33 ) First jobs and early ambitions

(07:39 ) Thanks to our sponsor, Navattic & ThriveStack

(10:47 ) A high-stakes decision to join Amplitude

(14:00 ) The reality of startup life

(16:00 ) Advice for aspiring startup employees

(18:55 ) Feedback and career growth

(26:41 ) Overcoming imposter syndrome

(27:11 ) Navigating leadership challenges

(29:16 ) Seeking clarity in a growing company

(30:52 ) Managing up and building relationships

(37:50 ) Handling layoffs and difficult conversations

(43:06 ) The importance of preparation and role-playing

(56:05 ) The value of deep thinking time

This episode is presented by:

Navattic: Interactive Product Demo Software - https://navattic.com/value

ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/

Resources:

Connect with Justin:

LinkedIn: https://www.linkedin.com/in/jjbauer/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching