PODCAST · business
dylan’s podcast
by Dylan Gallagher
Want to hear simple and practical business talk? After 20 years of working with entrepreneurs and business owners Dylan has lots to share. As the founder of Bridge Capital with a background in finance and technology he has made his own mistakes and doesn’t pull any punches when it comes to sharing his thoughts and opinions. This podcast is meant to inspire and encourage entrepreneurs.
Episodes
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When Success Isn't Enough, with Dylan Gallagher (Guest on Business as Mission (BAM) Canada)
*** 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…
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Eps 26 - How to Find Purpose as a Business Owner
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...
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Eps 25 - Why Your Team Fails—and Why It’s Your Fault
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...
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Eps 24 - Stop Paying People to Lose
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...
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Eps 23 - The Hidden Costs of Business Debt
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…
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Eps 22 - Why Cutting Costs Won’t Save You
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...
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Eps 21 - Canada’s Economy Needs a Therapist
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...
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Eps 20 - Canada Runs Like a Bad Business
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...
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Eps 19 - Take the Punch. Build Anyway.
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...
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Eps 18 - Rethinking My Highest and Best Use
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…
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Eps 17 - What If Your Business Sells—and You Have Nothing Left?
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...
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Eps 16 - Faith Isn’t a Bible Study—It’s How I Run My Company
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...
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Eps 15 - My Company’s Doubling—and I Can’t Be in the Way
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…
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Eps 14 - I’m Not Leaving Canada—But I’m Building Life Somewhere Else
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...
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Eps 13 - Why We're Choosing to Spend Less Time in Canada
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…
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Eps 12 - Canada’s Budget Is a Joke
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.…
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Eps 11 - A Mexican Moved to Canada for a Better Life. I’m Leaving Canada for the Same Reason.
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…
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Eps 10 - AI Agents, Emotional Letdowns, and the Reluctant March Toward the Exit
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...
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Eps 9 - Built My Own Software, Rebuilt My Team, and Canada’s Still a Mess
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…
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Eps 8 - My Legs Hurt, Boomers Are Hoarding Wealth, and Canada Is Tipping Into Irrelevance
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…
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Eps 7 - Boomers Think I’ve Lost My Mind — I Think They Wrecked the Country
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…
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Eps 6 - I Just Incorporated in the U.S. — and Gave Away My House
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…
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Eps 5 - Canada, You’re Making It Too Easy to Leave
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...
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Eps 4 - Play The Game On The Field
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…
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Eps 3 - You Know What, Dylan? I’ve Been Thinking…
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…
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Eps 2 - Maybe It's Not About The Math
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...
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Eps 1 - Watching a Great Place Become ...Less Great
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…
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Eps 0 - Canadian Election Results: What They Mean for My Business and Maybe Yours Too
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 —…
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Growing your business? What you need to know about debt and equity
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 https://wp.me/p2Ckbx-1BD Want to chat? Book a time:...
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What does the collapse of Silicon Valley Bank (SVB) mean for business owners?
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...
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Use negative review to get positive results
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...
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How to find new revenue streams
Finding new revenue streams can be as easy as solving unsolved problems for your existing customers. What does this mean? It means looking at the product or service your company offers the market and examining the process your customers go through to get it. As they make their way through your...
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How to get new clients and grow revenue
Need new clients? Need to grow revenue? The easiest way to do this is to determine which clients your business enjoys serving and which clients enjoy interacting with your company and then build a plan around finding more of them. A business that focuses on swapping out imperfect clients for...
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Why should employees be shareholders in your business
When does it make sense to have employees become shareholders in your business? Many business owners will offer shares to their team as a way to recognize their contribution and as a way to retain them. Many employees want to become shareholders to earn more money and participate in the value…
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Some thoughts on buying out a business partner
If you are in business with a partner, the day may come when you need to discuss how to exit the business. Conversations like this can go in many different directions. Generally speaking, the work completed (or lack thereof) when the company was created will directly impact the amount of work…
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How to get 100% out of your business
Doing ten things at 10% does not equal 100% - it equals 10%. Doing one thing at 100% that doesn't need to be done does not equal 100% - it equals 0%. Many business owners fall somewhere along the spectrum of being partially involved in many things or wholly involved in unimportant things. The...
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Grow a business that can run without you - Part 3
The most rewarding part of growing a business that can run without you is being able to invest your time and money into projects, causes, companies and opportunities that you find interesting. Time is the only asset anyone has; making the most of it can be an exciting and rewarding adventure.…
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Grow a business that can run without you - Part 2
It's hard to do, but it is necessary if you want to grow a business that can run without you you need to do it. You need to hire the right people to do the right jobs and empower them to make the right decisions. Many business owners believe they are the best people who know their business the…
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Grow a business that can run without you - Part 1
What is the next hardest thing a business owner learns to do after figuring out how to be profitable? Learning how to replace themselves. Business owners generally fill many different roles in their company, and often, no single role merits hiring a full-time (or even part-time) person. If you…
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How business owners create value
A business exists to create value by providing a solution to a problem that people have. There are a few reasons why people pay for products and services to solve their problems, including: 1. They don't want to solve their problem on their own. 2. They can't afford to solve their problem on…
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How to use a recession to improve your business
When times get tough - some people lean out, and some people lean in. Running a business during a recession is not easy, but if you can do it, you might find yourself reaping significant rewards when times get better. Getting through a recession is easier when you pay attention to what is…
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How to sell faster
There is a direct relationship between how well your business can market its products and services and how quickly your sales team can convert prospects into customers. Poorly thought-out marketing will produce a poor sales process for your team and a poor experience for your prospects. A...
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How to market your business faster
Do you wish your business could generate results faster from its marketing efforts? We all want results more quickly, but by its very nature, marketing is a long cycle process. If you have to get in front of your potential customer ten times before they decide to engage with you, a certain amount...
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Why do business owners struggle?
The struggle is real. Running a business is hard and making money is even more challenging. There is a moment many business owners have when they are unsure of their company's future. Understanding the next step in achieving a better outcome can be a struggle. There are three reasons a business...
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How to set prices in your business
Have you ever considered the prices your business charges for its products and services? How does it compare to the market? Is your business closer to the lowest or highest cost provider? Taking time to understand your competitors can go a long way in understanding where your business fits in the...
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1 easy way to boost sales
Is there an easy way to boost sales? Many business owners overlook the easiest and cheapest way to generate more sales even though they probably have all the pieces they need at their fingertips. A business expends a lot of time, money and effort acquiring a customer and their first sale. Some...
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How to buy a business - Part 3 of 3
Buying a business is exciting, and watching your ideas take shape can be very rewarding. Once you have found a business and structured a deal, you need a plan to get involved and make it your own. You can start by observing the culture, evaluating the people and resources, then deciding where you...
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How to buy a business - Part 2 of 3
Buying a business is exciting, especially if you don't need to write a check for it upfront. Many small business owners are more concerned about how they will untangle themselves from their business than how much money they will make from a sale. Using sweat equity and your knowledge and...
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How to buy a business - Part 1 of 3
Buying a business is an exciting opportunity. Many small business owners (baby boomers in particular) do not have an exit plan for how they will sell, wind down or walk away from their business. If you want to take the first step towards business ownership or want to grow your existing business,...
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Growing a business for the sake of growing a business
Grow. Grow. Grow. If you aren't growing your business, then your business is most probably shrinking. These are common statements many business owners hear - but are they correct? Are there reasons not to grow a business? Some of the questions you should ask yourself as a business owner include...
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ABOUT THIS SHOW
Want to hear simple and practical business talk? After 20 years of working with entrepreneurs and business owners Dylan has lots to share. As the founder of Bridge Capital with a background in finance and technology he has made his own mistakes and doesn’t pull any punches when it comes to sharing his thoughts and opinions. This podcast is meant to inspire and encourage entrepreneurs.
HOSTED BY
Dylan Gallagher
CATEGORIES
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Frequently Asked Questions
How many episodes does dylan’s podcast have?
dylan’s podcast currently has 150 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is dylan’s podcast about?
Want to hear simple and practical business talk? After 20 years of working with entrepreneurs and business owners Dylan has lots to share. As the founder of Bridge Capital with a background in finance and technology he has made his own mistakes and doesn’t pull any punches when it comes to sharing...
How often does dylan’s podcast release new episodes?
dylan’s podcast publishes regularly with 150 episodes available. Check the episode list for the typical release schedule.
Where can I listen to dylan’s podcast?
You can listen to dylan’s podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts dylan’s podcast?
dylan’s podcast is created and hosted by Dylan Gallagher.
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