EPISODE · Feb 22, 2025 · 8 MIN
Will It Work?
from Working Dads · host Dear Media
This isn’t just a podcast, a business experiment, or a creative outlet—it’s the beginning of something bigger than just numbers, profits, or views. It’s about exploring ideas without limits, testing what works (and what doesn’t), and sharing the raw, unfiltered process of building something from the ground up. In this episode, I dive deeper into: - The lessons learned from growing Penji - The first steps toward launching new ventures - Conversations that challenge the status quo of business and creativity - Why sometimes not knowing is the best way to start I don’t have all the answers. I don’t even have all the questions yet. But if there’s one thing I’ve learned from this journey, it’s that every great idea starts with action—and this is mine. If you’re here for the real, unpolished truth about entrepreneurship, creativity, and pushing past doubt, hit Subscribe and join me on this unpredictable journey. For dads figuring out work, family, and everything in between. Nobody prepares you for this. Not the guilt of leaving for work when your kid is still asleep. Not the pressure of providing for a family while trying to build something that actually matters. Not the identity crisis that hits when you realize you're not just the guy who grinds anymore — you're somebody's dad. And that changes everything. I started Working Dads because I lived that. I'm co-founder of Penji, husband to Emily, and dad to a two-year-old who already has more energy than I do. I've been bootstrapping a company for over a decade and I still don't have it all figured out. But I've learned that the most dangerous thing a working dad can do is try to figure it out alone. So every week I sit down with founders, executives, investors, and everyday dads who are in the thick of it. We talk about the real stuff. The marriage conversations you keep avoiding. The financial pressure nobody admits to. The moment your kid looks up at you and you realize you've been somewhere else even though you've been standing right there. We've also got Built During Bedtime — my weekly newsletter for working dads. The one thing I write after my daughter goes to sleep. Straight to your inbox. No fluff. And we've got a community. Slack channel and Facebook group full of dads who get it. The kind of guys you can be honest with. The kind of friendships that actually go somewhere. Come find your people. Working Dads. For dads figuring out work, family, and everything in between.
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What this episode covers
To be honest, I don’t know where this will lead—and maybe I don’t even care. What I do know is that I need to do this. Welcome to Episode 2 of Free Ideas.
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Will It Work?
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