In this episode, Aakash Gupta shares his journey from a tech-savvy kid in Kalamazoo, Michigan, to a successful product manager and creator in the Product Growth space.

He shares his tough feedback experiences, how he’s been able to overcome imposter syndrome, and how building a failed startup impacted his career. Aakash emphasizes the importance of self-care, emotional intelligence, and supportive mentorship in navigating corporate roles and leadership challenges.

Aakash opens up about:

How the collapse of a startup with 350k users reshaped his career and mindset

Getting specific feedback from a CMO that rattled his confidence

Navigating a sticky situation when a team member on a PIP attempted to turn the entire company against him

Things to listen for:

(00:00) Intro

(01:03) Aakash’s journey: From VP to Creator

(03:08) Debate skills shaping his product career

(05:29) First SaaS job building sports tools

(08:07) Lessons from his failed startup

(12:26) How mentorship changed his mindset

(14:17) Tough feedback from a CMO at Threadup

(16:33) The role of emotional intelligence in leadership

(28:08) Handling a difficult pip situation

(37:01) Dealing with imposter syndrome

(44:06) Personal habits for productivity