Winning the Founder Mental Game with Pilot’s Waseem Daher

Being small isn't a disadvantage—it's your superpower. 

Just one provocative sentiment from this episode that challenges conventional startup wisdom and delves into the mindset behind entrepreneurial success.

Waseem Daher brings insights from his journey across three successful startups—KSplice (acquired by Oracle), Zulip (acquired by Dropbox), and now Pilot, where he recently transitioned from CEO to executive chair. Host Raj Suri, himself a multi-time founder, creates an environment where honest founder-to-founder exchange flourishes beyond the typical success narratives.

The conversation unpacks frameworks such as the "David vs. Goliath" approach to competition, why unpopular decisions often signal good leadership, and how to maintain the delicate balance of the Stockdale paradox—confronting brutal facts while maintaining unwavering faith in eventual success. 

This episode offers rare insights into the psychological tools that sustain founders through years of uncertainty and challenge. The mental models discussed here apply beyond startups to any leadership position where resilience, decision-making, and maintaining perspective are crucial to success.