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 24, 2025
Saturday May 24, 2025
Today I unpack what it really looks like to integrate my faith into my business—not with Bible verses in boardrooms, but by taking ownership, creating culture, and serving others daily. Whether you’re a Christian in business or just wondering how faith and entrepreneurship collide, this episode lays out how I live it, lead it, and rely on it—every single day.
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Saturday May 24, 2025
Saturday May 24, 2025
Today I share what it’s really like to grow a company that’s doubling in size. From letting go of control to fixing broken processes and leading stressed-out managers—this is what scaling actually looks like. Plus, an update on our Spanish visa, and a reminder that no matter where we build, we have to do it from a place of service—not fear. If you’re growing something and it’s breaking, this one’s for you.
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Saturday May 24, 2025
Saturday May 24, 2025
Today, I share how we’ve started the process of applying for Spain’s Digital Nomad Visa. I also break down a hard leadership lesson: resetting expectations and owning mistakes. As I remove myself from day-to-day operations, our team is rising. And our family? We’re moving toward something generational—with purpose. If you’ve ever felt torn between staying and going, this episode might give you clarity.
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Sunday May 18, 2025
Sunday May 18, 2025
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.
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Sunday May 18, 2025
Sunday May 18, 2025
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.
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Sunday May 18, 2025
Sunday May 18, 2025
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.
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Sunday May 18, 2025
Sunday May 18, 2025
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.
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Sunday May 18, 2025
Sunday May 18, 2025
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.
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Saturday May 10, 2025
Saturday May 10, 2025
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.
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Saturday May 10, 2025
Saturday May 10, 2025
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.
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