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
Monday Jun 23, 2025
Monday Jun 23, 2025
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
Tuesday Jun 17, 2025
Tuesday Jun 17, 2025
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
Sunday Jun 15, 2025
Sunday Jun 15, 2025
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
Monday Jun 09, 2025
Monday Jun 09, 2025
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:
Saturday Jun 07, 2025
Saturday Jun 07, 2025
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.
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YouTube:
Sunday Jun 01, 2025
Sunday Jun 01, 2025
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:
Sunday Jun 01, 2025
Sunday Jun 01, 2025
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:
Sunday Jun 01, 2025
Sunday Jun 01, 2025
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:
Saturday May 24, 2025
Saturday May 24, 2025
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.
Blog:
YouTube:
Saturday May 24, 2025
Saturday May 24, 2025
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.
Blog:
YouTube: