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 10, 2025
Saturday May 10, 2025
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.
Blog:
YouTube:
Saturday May 10, 2025
Saturday May 10, 2025
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.
Blog:
YouTube:
Saturday May 03, 2025
Saturday May 03, 2025
In today’s weekly wrap-up, I reflect on what I thought was a financial decision — leaving Canada — and how it’s turned into something much deeper.
After running the numbers, I realized this isn’t about tax. It’s about energy, ambition, and playing the game as it actually is, not as we wish it were. I talk about growth inside my Calgary business, what I’m planning for the U.S., and why the desire to “go” is only getting stronger.
Topics in this episode:
- Why it’s not about the money anymore
- Building systems to double in size without burnout
- Lessons from other entrepreneurs facing uncertainty
- What “play the ball where it lies” means as a founder
Blog:
YouTube Episode:
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:
YouTube Episode:
Saturday May 03, 2025
Saturday May 03, 2025
On paper, moving to Texas, Spain, or staying in Canada all come out about the same from a tax perspective. So why am I still drawn to go? In this episode, I walk through the math behind different business income and personal tax scenarios across Texas, Calgary, and Spain. But what I ultimately realized is that this isn’t a tax decision — it’s a life decision.
If you’re a founder, entrepreneur, or creator trying to figure out where your next chapter should be — this episode might be the gut check you need.
Highlights:
- Tax comparison: Texas vs. Canada vs. Spain
- The real cost of staying in a place that’s lost its edge
- Why “a different shade of green” might be the answer
- Building across borders: balancing ambition and meaning
Blog:
YouTube Episode:
https://youtu.be/jrMT1zLcP8U
Saturday May 03, 2025
Saturday May 03, 2025
In this episode, I reflect on a difficult but honest realization: something once great — Alberta, Canada — has slowly become... average. I share what it’s been like to watch a thriving province lose its ambition, and how that’s shaped my thinking about relocating part of my life and business to the U.S. or Spain.
If you're a business owner wrestling with purpose, place, and what's next, this might resonate with you. I'm not just chasing lower taxes — I'm chasing the right environment for building something meaningful.
Topics covered:
- Leaving Canada: Emotional and economic reflections
- Comparing Alberta, Texas, and Spain
- Why building in a hopeful place matters
- Personal growth, family goals, and business direction
Blog:
YouTube Episode:
https://youtu.be/-9k4dS8MAWE
Saturday May 03, 2025
Saturday May 03, 2025
After the Canadian election, I’m asking tough questions: is Canada still the best place to build a future as a business owner? In this new series, I’ll document my real-time journey as a 47-year-old entrepreneur, husband, and father of five, wrestling with where to live, work, and thrive — Canada, the U.S., or even Europe. If you're a Canadian entrepreneur, business owner, or someone questioning what’s next after these election results, this series is for you.
Follow along for honest conversations about faith, family, business, and the pursuit of a better future.
Blog Post:
YouTube Episode:
Sunday Mar 19, 2023
Sunday Mar 19, 2023
Growing your business doesn't happen for free. Dylan shares some thoughts about how to pay for the cost of growth using debt and equity.
Watch this episode on YouTube:
https://youtube.com/live/YxIAUN0i_yg
Cash Flow Quadrant for Business Owners
Want to chat? Book a time: http://bit.ly/2rdDto2
Connect with dylan on LinkedIn at:
Saturday Mar 11, 2023
Saturday Mar 11, 2023
A black swan is an unpredictable event that is beyond what is normally expected of a situation and has potentially severe consequences. Dylan shares some thoughts about the collapse of Silicon Valley Bank (SVB) and what the average business owner should be thinking about as a result of it.
Watch this episode on YouTube:
https://youtube.com/live/xFnf6VF8DT4
Cash Flow Quadrant for Business Owners
Want to chat? Book a time: http://bit.ly/2rdDto2
Connect with dylan on LinkedIn at:
Tuesday Aug 16, 2022
Tuesday Aug 16, 2022
It was once said: "When life gives you lemons, plant its seeds, grow yourself an orchard, sell it to Sunkist. Carry on." Negative reviews can be a blessing in disguise for any business owner or entrepreneur who is serious about building a profitable and valuable company. There are two types of negative reviews - negative reviews for your company and negative reviews for your competitors. What many people overlook is that negative reviews can often hold the secret to making your business better. Once you move past the spam reviews and reviews from customers that will never be pleased, you are left with some ideas on how to improve your results. The negative reviews for your company and your competitors reveal what people are expecting and what they are happy to pay for. Whatever problems customers are experiencing and writing about are opportunities to provide solutions and make your business stand out. Lean into negative reviews and add money to your bottom line by exceeding your customers' expectations.
Watch this episode on YouTube:
Cash Flow Quadrant for Business Owners
Want to chat? Book a time: http://bit.ly/2rdDto2
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at: