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
2 hours ago
2 hours ago
12 min
The 2026 U.S. midterms gave me something to think about. Not just politics, but leadership, promises, expectations, and what it actually takes to earn people's trust.
My son recently asked me what I thought about the election results, the big tech sell-off, and Anthropic's anticipated IPO. I decided to record a few thoughts about where things might be heading.
I actually think the election results could be a good thing. With divided government, political leaders are going to have to work together if they want to accomplish anything. I see something similar happening with technology companies investing billions into AI infrastructure and data centres.
But the bigger lesson for me is about leadership.
This week, I spent some time with a business leader who invited me to observe one of his team meetings. Afterward, he asked whether he should make a big announcement about the changes he intended to make.
My advice was simple: just start doing things differently.
You don't always need to announce that you're making improvements. Sometimes the most effective thing you can do is make the change, consistently deliver, and let people see the results.
Every announcement creates an expectation. And when leaders don't deliver on those expectations, trust begins to disappear.
In this episode, I explore:
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Why the midterm election results could be a positive development
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What divided government might mean for businesses and the economy
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My thoughts on AI investments, data centres, and Anthropic
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Why people judge leaders by their everyday experiences
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The danger of overpromising and underdelivering
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A recent conversation about improving team meetings without making big announcements
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Why serving people and creating stability matter more than constantly projecting confidence
I think our responsibility as business owners is pretty straightforward: serve our people, build stable businesses, and deliver on what we commit to.
Give your team something worth working toward. Then do the work.
Let the results speak for themselves.
About Dylan Gallagher
I write and talk about business, entrepreneurship, ownership, leadership, and the responsibilities that come with building something of value.
Read more at https://dylangallagher.ca
If you're working through a challenge in your business and would benefit from another perspective, feel free to reach out through my website.
Aug 1, 2025
Aug 1, 2025
36 min
*** 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:
STAY CONNECTED WITH US:
WEBSITE: www.businessasmission.ca
LINKEDIN: @ Business As Mission (BAM) Canada
OUR PRIVATE COMMUNITY: www.businessasmission.ca/network
Jun 23, 2025
Jun 23, 2025
13 min
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
Jun 17, 2025
Jun 17, 2025
11 min
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:
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What the E-Myth got right (and what it means today)
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Why relying on “good people” is a leadership failure
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The danger of letting memory replace systems
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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.
YouTube:
https://youtu.be/64mYmA_WOdg
Jun 15, 2025
Jun 15, 2025
10 min
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.
Blog:
https://wp.me/p2Ckbx-25z
YouTube:
https://youtu.be/IgwYyAa0t6c
Jun 9, 2025
Jun 9, 2025
11 min
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.
Blog:
YouTube:
Jun 7, 2025
Jun 7, 2025
12 min
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.
Blog:
YouTube:
Jun 1, 2025
Jun 1, 2025
11 min
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.
Blog:
YouTube:
Jun 1, 2025
Jun 1, 2025
14 min
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.
Blog:
YouTube:
Jun 1, 2025
Jun 1, 2025
11 min
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.
Blog:
YouTube: