Claim Ownershipdylan’s Podcast
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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.
232 Episodes
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*** Guest on Business as Mission (BAM) Canada ***
What makes someone an entrepreneur? Is it a lengthy resume, a heavy academic record, a successful business? Or does being an entrepreneur mean something else entirely...
Dylan Gallagher, Founder of OndeWork, has been exploring what it means to be an entrepreneur ever since he was a kid. With years of youthful exploration and practical experience in the business world, Gallagher has developed a successful people-driven company that is built on a foundation of trust in God. Through this business, God has shown him what it means to be an entrepreneur and a Kingdom-seeker.
Resources from this episode:
Dylan's LinkedIn
OndeWork's Website
STAY CONNECTED WITH US:
WEBSITE: www.businessasmission.ca
LINKEDIN: @ Business As Mission (BAM) Canada
OUR PRIVATE COMMUNITY: www.businessasmission.ca/network
Are you working harder every year but still feel like you’re building into the void? This episode breaks down what to do when your business feels aimless—even if it’s profitable.
You’ll discover:
- Why most entrepreneurs burn out after growth, not before
- A simple way to reclaim direction using your balance sheet
- How to move from “job” to “asset” through 3 clear financial stages
- A back-of-napkin method to value your business—even if you're not selling
If you’re stuck scaling your business without a clear win, this episode is for you. It’s time to stop working into the void—and start building something that pays you back.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25F
YouTube:
https://youtu.be/O5sCH3Tssko
What happens when you stop being the operator and start being the owner—but your systems haven’t caught up? This episode gets brutally honest about the emotional weight of building a business that actually works without you.
I share:
What the E-Myth got right (and what it means today)
Why relying on “good people” is a leadership failure
The danger of letting memory replace systems
Why we’re rebuilding our entire field mobilization process from scratch
If you're trying to build something bigger than yourself—something sustainable, repeatable, and people-first—this one is for you.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25C
YouTube:
https://youtu.be/64mYmA_WOdg
If Canada were a business, half the team would be fired. In this episode, I unpack the June wage and productivity report — and what it reveals about the economy, leadership, and how business owners like us can (and must) respond differently. I share what I’m doing inside my company to avoid the same traps and why capital allocation — not more hiring — might be your most important decision right now.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25z
YouTube:
https://youtu.be/IgwYyAa0t6c
Debt doesn’t just limit your cash—it limits your leadership. In today’s episode, I unpack why the wrong kind of debt is a silent killer in your business. From biblical wisdom to practical business strategy, I explore what it means to borrow like a steward, not a slave. If you’re carrying debt that isn’t creating value, it’s costing more than you think. Here’s how to change that—so you can lead in freedom again.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25x
YouTube:
https://youtu.be/kZJpGVipju0
The U.S. won’t cut its debt. Your business shouldn’t either. In this episode, I explain why “cutting your way to profitability” is a lie—and how real entrepreneurs grow their way out of financial stress. From replacing overpriced software to flipping payroll into performance pay, I share what worked for us—and what scripture says about stewardship, cash flow, and choosing which master you serve. If you’ve hit the edge, this one’s for you.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25u
YouTube:
https://youtu.be/gav0vDgr0pc
In today’s episode, I explain why I’ve stopped trying to escape Canada—and started building better within it. I explore what it means to personify countries, what Elon Musk’s resignation from public influence really teaches us, and why I’m choosing to double down on people when the economy feels like it’s failing. I’m still going to the U.S. and Spain. But Canada? Maybe it’s not a lost cause—if we build the future ourselves.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25r
YouTube:
https://youtu.be/kPm6-75GzLM
In today’s episode, I break down why Canada’s economy mirrors a badly run business—low productivity, no vision, and zero incentive to improve. From falling capital investment to a government acting more like a goalie than a leader, it’s clear why entrepreneurs are hesitant to grow here. I unpack the numbers, the missed opportunities, and the real-world options forward—including what we’re doing in the U.S. and Spain instead. If you're a builder, this one’s for you.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25n
YouTube:
https://youtu.be/2u2FrarRSqg
Hiring has stalled. Capital investment is frozen. Inflation is looming. So what now? In this episode, I share how we’re responding inside our company—using AI, doubling down on partnerships, and locking in cost controls. I explain why waiting is the worst strategy during uncertainty, and how to take the punch, make the pivot, and keep building when others freeze. This is what real leadership looks like when the economy shifts.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25k
YouTube:
https://youtu.be/WvtFVecIH4k
This week, I explore a question every entrepreneur must face: what is your highest and best use? Inspired by Elon Musk’s pivot back to the private sector, I reflect on how changing environments—from Canada to Spain to the U.S.—are shaping where and how I want to lead. If your margins are tight, the stress is mounting, and you feel the pull toward purpose, this episode is for you. It’s not about leaving—it’s about building where you’re most needed.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25h
YouTube:
https://youtu.be/2Zn_s6rPVHk
In this episode, I talk about what happens after you build something successful. Inspired by Elon Musk’s recent shift, I reflect on the bigger question entrepreneurs face: what’s next when your business isn’t the only thing you’re meant to build? I share how I’m investing in purpose beyond profit—and what it might look like for you to find fulfillment after the exit, even if you never sell.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-25c
YouTube:
https://youtu.be/clDqKD6GAhQ
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.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-257
YouTube:
https://youtu.be/TK5ytUDnF9Y
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.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-253
YouTube:
https://youtu.be/-bNis68exWA
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.
http://x.com/dylangallagher
Blog:
https://wp.me/p2Ckbx-250
YouTube:
https://youtu.be/4dGgghzxfxA
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
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Thank you Dylan for this excellent podcast. I for one would like to see more information on sales, as we know any business of any size that without sales we don't exist, it's should be,. for any size business the number one priority in growing our business.
Brilliant insights. love your podcasts Dylan, keep them coming.
Great advice Dylan. I'm choosing also to look, seek the positive opportunities in these uncertain times. And I've been blessed because I believe looking where others are not, I'm doing well. Zig while others zag. Keep it up Dylan. Your insights are much appreciated.