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
Delivering Value: Tough Career Moments - Lessons from Growth, Marketing & Product Leaders