EPISODE · Sep 14, 2026 · 50 MIN
Fail Cheap While You're Still Young┃Joe Tomco: Entrepreneur and Family Man
from Chasing Glass
Hey! I'd love to hear your thoughts, send me a voice note.This is part two of my conversation with Joe Tomco, and it goes even deeper than part one. Joe tells me about the weekend he closed a massive deal with General Electric Latin America before his product was even finished. He was up almost 20 hours a day for four days straight, running the whole thing by hand behind the scenes, because he had already promised his customer something automated. That story alone says everything about what building a business actually looks like behind closed doors. We also get into venture capital and what he calls the golden handcuffs, the pressure to grow faster and faster until you feel more like an employee of your investors than the owner of your own company. Joe opens up about the exact moment 50 million users stopped feeling like the win he thought it would be, and why he eventually walked away from tech to run a pool store instead. Joe is also a bishop, and he talks honestly about mental health, empathy, and the idea that almost everyone you pass on the street is carrying something you can't see. He shares the line that changed how he thinks about work and family, that nobody lies on their deathbed wishing they had worked more. If you're a student, a founder, or anyone who feels stuck on a path that doesn't feel like yours, this episode is for you. If this conversation brings something up for you, Clearapy is a warmline for anyone who needs to talk it out. Call 863-334-2447. Catch part one if you haven't yet, and new episodes drop every week on Chasing Glass.
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Fail Cheap While You're Still Young┃Joe Tomco: Entrepreneur and Family Man
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