Eps 5 - Canada, You’re Making It Too Easy to Leave

2025-05-10

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In today’s episode, I break down why—after comparing taxes, cost of living, and opportunity—I’m leaning toward building the next chapter of my life and business in the U.S. It’s not just about money. It’s about motivation. - Why does it feel like ambition is slowly dying in Canada? - Why does it seem harder to dream big here than it used to? - What would it take to split life between Canada and the U.S. under an E-2 visa? I dive into comparisons between Calgary, Austin, and Nashville, and unpack how politics, policy, and...

In today’s episode, I break down why—after comparing taxes, cost of living, and opportunity—I’m leaning toward building the next chapter of my life and business in the U.S.

It’s not just about money. It’s about motivation.

- Why does it feel like ambition is slowly dying in Canada?

- Why does it seem harder to dream big here than it used to?

- What would it take to split life between Canada and the U.S. under an E-2 visa?

I dive into comparisons between Calgary, Austin, and Nashville, and unpack how politics, policy, and personal legacy are shaping the biggest decision I’ve made in years. If you’ve ever thought about moving for more than just money—this episode is for you.

http://x.com/dylangallagher

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YouTube:

https://youtu.be/INlHtAPU1zg

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