S2:E18 - Making Pigs Fly: Turn early career lessons, empathy, and curiosity into product success.

In this episode of Practical Product Management, we sit down with Ali Rakhimov, Senior Product Leader, fintech founder, and author of Make Pigs Fly. We didn’t know Ali before this conversation, but we quickly found ourselves deep in stories about his unconventional path into product management as a self-taught immigrant, the lessons he learned building fintech for underserved schools, and how he went on to lead $10M+ initiatives at Macy’s and T-Mobile.

We talked about why asking so-called “stupid” questions is actually one of the smartest things a PM can do, how empathy for real users translates into stable and trustworthy systems, and what Ali has learned about communication and adaptability—whether in a boardroom, a classroom, or at home raising four kids. This was a conversation full of practical wisdom, honesty about mistakes, and reminders that product management isn’t about fluff, it’s about building things that work and staying human while you do it.

Key Takeaways

1. Curiosity over credibility: Asking the “stupid” questions is often how you uncover blind spots, learn fast, and earn trust.

2. Empathy into action: Observing real users and solving their core problems matters more than shipping flashy features.

3. Adaptability is leadership: Whether managing teams or parenting, effective product leaders flex their style to the audience and context.

Questions for PMs

1. When was the last time you asked a “stupid” question—and what did it unlock for you or your team?

2. How do you make sure user empathy shows up in the systems and features you build, not just in documents?

3. In your own leadership style, how do you flex and adapt to different people and situations?