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.

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’d gone to university and studied biology and project management. 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 (and this is the important part), 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 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’d not really thought about it, and it set a course for a new project for the two of us where 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, 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

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