This week, I unpack the deeper reason we’re leaving Canada—and it has nothing to do with taxes or policy (okay, maybe a little). I share a conversation with another dad, another entrepreneur, who’s staying and building wealth so his kids can survive. Meanwhile, we’re going—trusting that faith, not finance, is the future. If you’re wrestling with where to go, why to stay, or what really matters, this episode is for you.

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-24W

YouTube:

https://youtu.be/C4zVRy675qk

Canada’s new “budget” isn’t a budget at all—it’s a recycled framework propping up broken incentives and punishing value creators.

In this episode, I break down why capital gains tax hikes, hollow housing promises, and performative social programs signal the end of Canada as a builder’s paradise.

If you're an entrepreneur, investor, or parent trying to plan for the future, this one might sting—but it might also give you clarity.

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-24R

YouTube:

https://youtu.be/cWCeZu6UP7A

Today’s episode is a gut check.

I onboarded a new team member—an overqualified accountant from Mexico who moved to Canada with his family seeking a better future. And here I am, doing everything I can to leave the very country he moved to.

So… what gives?

I unpack:

- Why I feel conflicted but clear

- Why I believe my highest and best use is investing in people, not scaling for the sake of it

- How faith, family, and service now shape every business decision I make

- And why leaving Canada is not about running away, but about building something worth running toward

If you’ve ever wrestled with what success actually looks like, or wondered if it’s time to go where the wave is rising—this one’s for you.

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-24O

YouTube:

https://youtu.be/ZuvnbbykuCI

In today’s episode, I talk about:

- Why internal promotions are harder than you'd think

- The frustrating reality of team members who don’t want to grow

- How I used ChatGPT and Google’s NotebookLM to review my website, generate a podcast, and create social content—all powered by AI

- The difference between having data and owning it

- And why I'm laser-focused on building web traffic before expanding OndeWork further into the U.S.

This one’s about ownership, marketing, AI, and the subtle heartbreak of realizing some people on your team just don’t want what you hoped they would.

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-24L

YouTube:

https://youtu.be/oHjKfUh7bPI

In today’s episode, I talk about:

- How I used AI to build our own project management system

- Why I replaced Buildertrend with a custom platform tailored to our business

- What it means to stop “hiring” and start investing in people

- Why our accounting is going back onshore—and why that’s a good thing

- The true role of a business owner in 2025: get out of the way

If you’re an entrepreneur, founder, or builder trying to grow something that doesn’t collapse under your weight—this episode is for you.

I also unpack what value creation actually means, and why I’m doubling down on Canada (for now), while gearing up to replicate this entire playbook in the U.S.

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-24H

YouTube:

https://youtu.be/hX1lApT6P1Q

In this Saturday wrap-up, I reflect on the week’s big moves and bigger questions:

✅ Incorporating a U.S. company and opening a U.S. bank account

🌀 Battling bureaucracy for a U.S. tax ID

💥 Generational friction, value creation, and why Canada feels like it’s slipping

💡 Why Spain offers hope, and the U.S. still offers upside

I share the philosophy behind everything we’re doing—why we see our family’s resources as something we steward for the next generation, not something to hoard or spend for comfort.

This isn’t just about leaving Canada. It’s about building something that will matter after we’re gone.

If you’re a builder, a parent, or someone trying to make sense of where the world is headed—this episode is for you.

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-24w

YouTube:

https://youtu.be/lCdFTuqkqbQ

I break down why I’ve decided to shift my life and business outside of Canada—and why some boomers (and even family) think I’ve completely lost the plot.

But this isn’t about opinions.

It’s about:

📉 The shrinking private sector in Canada

🛠️ The collapse of productivity

💸 The skyrocketing cost of living—and how it compares to the U.S. and Spain

If you’re wondering why I’ve incorporated in the U.S., opened a bank account, and started down the path of an E-2 visa (and even looking at Spain’s digital nomad option), this episode is the clearest explanation yet.

It’s not about politics.

It’s not about outrage.

It’s about making decisions with the clearest data I’ve got.

So, if you’re in the private sector… if you’re feeling the squeeze… if you’re wondering whether it’s time to go—this one’s for you.

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-24t

YouTube:

https://youtu.be/Fse5QfPgAaw

On May 7, I did two things that pushed my life into a whole new gear:

I incorporated a U.S. company through Stripe Atlas to begin the E-2 visa journey. I handed over our house to another family—meaning come December, we’re technically homeless.

This episode is about momentum.

- What it means to go from idea to action.

- Why I’m re-architecting my life and business.

- And how I’m setting up my team in Canada so I can start laying the foundation in the U.S.

We’re growing fast. I’ve got a new bookkeeper coming in. I’m working to remove myself from the day-to-day financial choke points so I can focus on scaling OndeWork—and possibly launching a U.S.-based construction company too.

If you’ve ever been on the edge of something big—and scary—this episode is for you.

http://x.com/dylangallagher

Blog:

https://wp.me/p2Ckbx-24p

YouTube:

https://youtu.be/KvuIOUzb1OU