dylan’s Podcast explores entrepreneurship through the lenses of finance, faith, and the future. Drawing on real-world experience, he blends economic insight, personal stories, and quiet spiritual themes to challenge how we think about work and wealth. With a thoughtful, sometimes contrarian tone, each episode offers clarity and reflection—less about hustle, more about what’s worth building and why.
Episodes
Saturday May 03, 2025
Saturday May 03, 2025
Today, I share the conversation that shifted everything.
For months, I’ve been wrestling with the idea of uprooting how our family lives and works — spending six months in the U.S., 90 days in Spain, and 90 days in Canada. This morning, Lisa finally said the words every entrepreneur longs to hear: “You know what, I’ve been thinking... I think you’re right.”
In this episode, I reflect on what it’s like to think like a founder, why this decision isn’t about the math, and how most business owners eventually face the same hard question: Is this still worth it?
In this episode:
- The quiet breaking point many entrepreneurs reach
- The diminishing return on effort in Canada
- Conversations with business owners juggling 8-figure risks
- Why staying might be logical… but going might be necessary
Blog:
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