Financial Flight Plans + Everyday Change Makers: Mike Reilly on Wealth, Legacy and Community

Hi there, and welcome back to another episode of The Eloquent Entrepreneur—the blog edition.

In today’s episode, I had the privilege of sitting down with Mike Reilly, financial advisor, founder of Gaining Altitude Financial, community leader, and all-around everyday changemaker.

What I love about speaking with Mike is hearing how he blends empathy, education, and practicality in everything he does. It’s incredible how some people land in entrepreneurship not by choice but by accident. The result?

For Mike, it’s given him a new perspective on what he wants out of life and business. Today, he’s helping clients understand not just their finances, but their values, their goals, and the legacy they want to leave behind.

https://www.youtube.com/watch?v=n1aTwatTHgA

The Origin of Gaining Altitude Financial

Mike didn’t begin his career in finance. In fact, money was something he actively avoided growing up. “The only time I ever really heard my parents talk about money was when they fought about the bills,” said Mike. “To me, money was a source of conflict.”

He studied biology and project management at university. It wasn’t until a mentor spoke to him and recommended a career in finance that things shifted. Fast-forward to today, and he owns and operates his company, Gaining Altitude Financial, based in the West Shore near Victoria, BC. Mike works with clients across Canada, focusing not just on wealth but on financial literacy.

“The real value in what I can bring is to people who are just starting out,” he told me. “Did you just buy a house? Get married? Have a child? Those are the people who really need advice before it’s too late.”

When he meets clients, his first goal isn’t to sell products; it’s to help people understand how to use money as a tool for clarity, stability, and confidence. Anyone can sell you products, but to make it his end goal to help a client better understand their finances is a much more important goal in my books (and his).

Breaking the Taboo Around Money

Like many of us, money wasn’t openly discussed in Mike’s childhood, and that silence followed him into adulthood.

But he wants to change all of that for his clients.

That’s why so much of his work today focuses on financial literacy and the conversations families often avoid:

• wills

• probate

• estate planning

• disability coverage

• risk management

• generational wealth transfer.

  
  

He also teaches financial literacy in high schools through Junior Achievement, ensuring students hear—maybe for the first time—how credit works, why savings matter, and how debt accumulates.

The Financial Flight Plan

Mike speaks about his frameworks, and one of them in the Financial Flight Plan is: “Your financial life follows a flight plan—from taking on fuel early in your career to cruising speed and, eventually, a landing pattern,” explained Mike. “There are different requirements at each stage, and you have to course-correct as life happens.”

It removes the pressure to “get everything right” and instead focuses on steady steps forward.

I like the analogy, and it helps with big-picture thinking. It focuses on the journey and not the destination.

Working With Mike Reilly on Change

I've actually started a project with Mike. It all came out of a discussion where I asked him, “Why are there no outdoor pools in Victoria?”

Mike explained that when I asked him that, my question hit him hard. “Your statement hit me like a two-by-four,” said Mike.

He hadn’t really thought about it, and it set a course for a new project for the two of us. We have made it our mission to work with a variety of different stakeholders to bring an outdoor pool to the West Shore.

It’s going to take time to get the support, signatures, plans, and then eventually build it—but we’re determined. We’ve formed a new committee, we’re working with municipalities, and we’re committed to seeing this project through.

“Outdoor pools are a great social leveller. It is something that everyone has access to,” said Mike.

That’s exactly what we want: a space that welcomes families, seniors, kids, and teens—people across all different socio-economic backgrounds. A place that strengthens community connection and creates opportunities for recreation, wellness, and belonging.

Legacy, Literacy, and Lifting Others Up

Mike is passionate about helping women over 60 understand their financial landscape—especially those who may not have managed the family finances. Too many women, he says, don’t know the details of their estate or financial accounts until it’s too late.

His Family Legacy events create space for those conversations, bringing women, spouses, and adult children together to talk openly about inheritance, planning, and legacy. He also leads cross-generational workshops because, as he told me, financial literacy “is beneficial for everybody”—and the more the community understands, the stronger we all are.

Looking Ahead

As for the next five years, Mike hopes to keep his practice small, personal, and meaningful—focused on relationships, not volume. He wants to support his associate advisor, grow his team thoughtfully, and continue giving back to the community in ways that matter.

And his advice for anyone wanting to make a difference?

“If you’re asked to do something, say yes,” said Mike. “Action leads to motivation. Not the other way around.”

It’s simple, practical, and true. Everyday change doesn’t come from waiting for inspiration—it comes from taking one small, steady step.

Listen to the Episode

Hear the full conversation with Mike Reilly on The Eloquent Entrepreneur. We explore money, legacy, community, confidence, and what it means to build a life—and a neighbourhood—intentionally.

Listen now on YouTube, Apple, or Spotify Podcasts.

Connect with Mike Reilly

To learn more about Mike and the services he offers, visit him at Gaining Altitude Financial or on Instagram.

The Importance of Financial Literacy

Financial literacy is more than just understanding numbers. It’s about feeling empowered. It’s about knowing that you can make informed decisions. This knowledge can transform lives.

When we talk about money openly, we break down barriers. We create a culture where questions are welcomed. This is crucial for personal growth and community development.

Creating a Supportive Environment

In our journey with Mike, we’ve learned the value of creating a supportive environment. It’s essential to surround ourselves with people who encourage us. When we share our goals, we invite collaboration.

This is especially true in financial discussions. When we share our experiences, we help others feel less alone. It’s a beautiful cycle of support and encouragement.

Taking Action Together

As we move forward, let’s remember the power of taking action together. Each small step contributes to a larger vision. Whether it’s starting a new project or simply having a conversation, every effort counts.

Together, we can create a community that thrives on understanding and support. Let’s continue to lift each other up. After all, we’re all in this together.

Embracing Change

Change can be daunting, but it’s also an opportunity. Embracing change means welcoming growth. It’s about stepping outside our comfort zones.

When we face challenges, we learn more about ourselves. We discover our strengths and resilience. This journey of self-discovery is invaluable.

The Path to Financial Freedom

Financial freedom is a journey, not a destination. It’s about making choices that align with our values and dreams. Each decision we make shapes our future.

By understanding our finances, we can create a life that reflects our true selves. This journey is not just about money; it’s about living authentically.

The Ripple Effect of Financial Literacy

When we invest in our financial education, we create a ripple effect. Our knowledge can inspire others. It can spark conversations and lead to collective growth.

Imagine a community where everyone feels confident discussing money. This is the future we can create together.

Conclusion: A Call to Action

In closing, let’s keep the conversation going. Let’s continue to explore the world of finance, community, and personal growth. Together, we can create a brighter future.

Remember, the journey of a thousand miles begins with a single step. Let’s take that step together.