The narrative we tell about career transition usually goes linear: you climb a ladder until you jump to a different ladder. But what happens when two people move in opposite directions and end up solving identical problems?
Drew Feldman spent years in film and theater before launching a financial advisory practice. Jason Friedman spent years as a financial advisor before building Advisor Finder, a platform designed to solve the advisor-client matchmaking problem that frustrated him from the inside. On the surface, they're moving in opposite directions. But the real story is underneath: both discovered that authenticity, genuine networks, and refusing to perform becomes your actual competitive advantage, whether you're pitching projects or pitching yourself as trustworthy with someone's money.
This episode cuts through the noise of personal branding to ask what actually builds trust across industries and transitions. It's about staying genuine when everyone's telling you to optimize, building networks that aren't transactional, and recognizing that the skills you learned in one world translate everywhere. The stories they tell about Shabbat as a reset, about texting a private equity CEO like he's a friend, and about why "workarounds" are more honest than solutions reveal something most conversations miss: how we actually move through the world matters more than where we're moving toward.
