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 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:
Monday Aug 08, 2022
Monday Aug 08, 2022
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 customer experience, there are probably opportunities to help them solve other challenges. Finding new revenue streams depends upon your ability to remove yourself from your business, place yourself in your customers' place and examine what they go through in the course of using your products or services. What problems do your customers have that are currently unsolved? Answering this question takes effort, but your bottom line will reward you if you can.
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:
Friday Aug 05, 2022
Friday Aug 05, 2022
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 perfect clients is a business that is maximizing its resources and is efficiently maximizing its profit. It is challenging for a company to serve different types of customers. Each type of customer a business helps interrupts its ability to run efficiently, effectively and profitably. Adjusting to the needs of different types of customers means a company has to change how it delivers its products and services. The adjustments reduce profitability and limit revenue. The goal is to reduce the variety of customers your business serves and focus on a few that are highly profitable, easy to work with and who enjoy interacting with your company. Growing revenue doesn't mean expanding your customer base as much as swapping out imperfect clients for perfect ones.
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:
Thursday Aug 04, 2022
Thursday Aug 04, 2022
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 they are creating. Giving employees shares in your business will only be meaningful if you have determined what you believe the business's value will be and how their efforts will help ensure it materializes. In the absence of concrete goals, offering shares to employees is, at best, a token exercise that will not produce the intended effect. If you want to provide employees with shares in your business, spend time and effort to put a plan together that shows them where the company is going and what it will be worth once it gets there. Doing this will make the exercise meaningful and worthwhile.
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:
Wednesday Aug 03, 2022
Wednesday Aug 03, 2022
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 that must be completed when the company dissolves or its structure changes. Many small businesses are formed informally without shareholder agreements, exit strategies or written expectations of each participant's responsibilities. The lack of structure and planning at the onset of a company will result in business partners having to work through details when they decide to buy each other out. Because expectations are often unclear, valuation methods used to determine payout amounts can be biased, and communication can become cordial and frustrating. One of the easiest ways to buy out a business partner is to look back at the history of the business, how the partners were each participating and then have a frank conversation about what is reasonable and fair for everyone involved. This approach doesn't mean everyone gets what they want, but common sense might enable a speedier outcome than what might have been realized otherwise. Getting caught up in details that were not part of how a company was formed or managed can be challenging to impose when the company needs to change. History can be a good reference point for setting a future course of action.
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:
Wednesday Aug 03, 2022
Wednesday Aug 03, 2022
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 quality of a business owner's goals will determine their effectiveness in meeting them. A business owner will get under-involved in many things or over-involved in a few things because they do not have well-defined goals or do not have a good understanding of where their business needs to focus. The very nature of business is change, and a business owner needs to focus on the tasks and opportunities that will significantly impact their company. Business owners get pulled in many different directions daily, and there is no shortage of activities to spend time on. The key to getting 100% out of your business is to focus on activities that will make the most considerable difference in your company.
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: