Most founders spend years asking the wrong questions. “How fast can this grow? How big could this be? What’s the smartest next move?”

But the questions that actually shape your life usually come much later… often after you’re already exhausted, anxious, or stuck on a path that doesn’t feel right anymore.

In this episode of Not Another Podcast, Brennan sits down with Evan Walden, CEO and co-founder of Getro (recently acquired by Findem), for a grounded, deeply human conversation about what it really means to build something over the long term.

Evan has spent nearly a decade building companies, mentoring founders, and watching smart, capable people quietly struggle. This isn’t because they weren’t talented, but because they never stopped to ask what they were actually trying to build for themselves.

This episode explores:

• Why companies don’t really die when they run out of money
• The difference between keeping something alive through force and building something sustainable
• How self-doubt shows up uniquely for entrepreneurs who are creating something from nothing
• Why people-pleasing and external validation quietly sabotage founders
• The hidden cost of hustle culture and seven-days-a-week thinking
• Why taking time off is a signal of strength, not weakness
• How values act as a decision-making system when everything feels ambiguous
• The idea that every business starts as an art project and the moment when you have to decide what it’s becoming
• How to zoom out and ask: Is this still the right thing for me to be working on?

They also talk openly about mental health, therapy, leadership, culture, and the fear many founders carry that if they step away, everything will fall apart. This conversation isn’t about one “right” way to build.

It’s about choosing a game you actually want to play and building something that fits who you are, not just who you think you’re supposed to be.

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