Eps 3 - You Know What, Dylan? I’ve Been Thinking…

2025-05-03

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 th...

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

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-245

YouTube Episode:

https://youtu.be/2MVc0m0eWiM

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