In August of 2023, a few months after Insight Mortgage became a real company instead of a name I kept saying out loud to see if it fit, I was invited on the I Love Kelowna podcast. We were supposed to talk about mortgages. We ended up talking about debt, coaching, accountability, and what honesty costs in a sales industry. When the episode went live that September, it carried a title I’ve been trying to live up to ever since: “Empathy, Leadership and Love.”
Love. On a mortgage podcast. I’ve made my peace with it.
I’m bringing this up now because if you’ve visited the site lately, you’ll have noticed everything looks different. New brand, new focus, considerably more of my face than I’m entirely comfortable with. I know how rebrands read from the outside. They usually mean a pivot, a shake-up, some consultant’s idea of a fresh start. So let me say it plainly: nothing about the strategy has changed. The last three years just convinced me to stop being quiet about it.
Some background, for anyone new here.
I didn’t grow up in this industry. I spent years in the corporate world before getting licensed in 2019, and I arrived carrying something most brokers would never put on a website: at twenty-one, I was $180,000 in debt. That’s not a typo. I’m forty-one now, which puts that hole exactly half a lifetime behind me, and I still tell the story every chance I get, because it’s the reason empathy isn’t a poster in my office. When someone sits across from me embarrassed about where their finances have ended up, they’re not confessing to a judge. They’re talking to a guy who’s been further down that hole than they are.
And what changed my direction back then wasn’t a windfall. It was a person. Early on, someone in this business looked at my mess and had every professional reason to pass. Instead, what I got was, more or less word for word, “okay, no, sit down, let’s go over it, let’s run credit, let’s figure this out.” I’ve built an entire company on that one sentence. Education first, judgment never. I didn’t invent the approach. I received it.
Teaching turned out to be the thread running through everything I do when nobody’s paying me. I coach with BC Youth Football. I sit on mentor teams for early-stage founders through the UBC Venture Mentoring Service at UBC Okanagan, a program whose stated philosophy is building the person, not the business, which should tell you exactly why I signed up. Add in, as I put it on that podcast, “a lot of young business professionals that are kind of coming up in the world,” and the pattern gets hard to miss. When CBC Radio calls asking if I can explain a rate announcement in plain English, I say yes. In 2021, this way of working won me the Canadian Mortgage Professionals’ Rising Star award, which was a nice thing to receive and, in fairness, easier to earn in a market where money was nearly free and every deal closed.
Then the market turned, and the award stopped mattering.
You know this part even if you’ve never worked in finance. Between March 2022 and July 2023, the Bank of Canada raised rates ten times. Files that should have been celebrations became phone calls nobody wanted to make. People renewed out of mortgages under two percent into payments that frightened them, and my job became sitting in that fear with them, one kitchen table at a time. Some of my best work in those years earned me nothing on paper. There were clients I told not to buy. There were commissions the honest answer cost me.
And then there’s the part I’ve rewritten a dozen times and nearly cut.
That episode, the one titled “Empathy, Leadership and Love,” was recorded in August of 2023. Six months later, my relationship of nineteen years ended. I’m not going to write about the separation itself. It involves people I care about, and they didn’t sign up to appear on a mortgage website. But I can’t write honestly about these years and leave it out. I sat in front of a microphone and talked about love while standing, without knowing it, six months from my world coming completely apart. For a long stretch afterward, I was walking clients through the worst financial season of their lives while privately living through the worst personal season of mine.
I’m telling you this because it’s where the rebrand actually comes from. When your life gets stress-tested, you find out quickly which of your values were decoration. I had been saying those three words for years. In 2024, I had to live on them, and they held. The business, strangely, came out stronger too. The clients stayed. Then they sent me their parents, their kids, their coworkers. Nothing markets a broker like being told the truth in a bad year. And nothing teaches you how to sit with someone else’s fear like carrying some of your own.
I’ll be honest about the timeline, too. All of this, the site, the visibility, articles with my name on them, is recent. For a stretch I kept my head down and just worked. Quiet files, quiet referrals, trying to win while staying invisible. It doesn’t work. Not for long, anyway. This year I found my way back into the fold, and the difference is that this time it isn’t only about me. There’s a team at Insight Mortgage now that needs the best version of me showing up, and an industry that, frankly, needs more people willing to lead from somewhere visible. On that podcast I said, “if we can see it like it’s a team game, it changes the dynamic immediately.” I meant real estate deals at the time. It turns out to be true of everything.
Which brings me to the industry, and why the new site looks the way it does.
The mortgage business I joined still ran, mostly, on information asymmetry. The broker held the rate sheets and the lender relationships, and the client’s job was to trust the process. That era is ending. Your clients have asked an AI three questions before they’ve asked you one. Every advertised rate is on their phone. None of this worries me, because information was never actually the product. Honest advice is. Context for your specific situation, a straight read of your options, and a person accountable to you instead of to a sales target. I said a version of this back in 2023: “I don’t hide anything… there’s a leadership component to it too.” Transparency was never a marketing angle for me. It’s what leadership looks like when you apply it to money.
There’s a changing of the guard happening in mortgage brokering, from gatekeepers to educators, and honestly, I find it energizing. The industry is drifting toward the way some of us already work. The rebrand is me saying so out loud.
So, what’s actually different? The education was always part of the job; what’s new is that it’s finally getting built out properly: plain-language guides, real numbers, straight answers to the questions banks make people feel dumb for asking, landing on the site piece by piece whether you ever call me or not. The focus is sharper, leaning toward the clients the system treats as inconvenient: first-time buyers, self-employed people whose income is real but doesn’t fit a bank’s template, anyone rebuilding credit. And I’m at the front of it now, name and face and stories like this one. On that same 2023 episode, I said I wanted to build a brokerage where people could “be their authentic selves and still find success.” It took me three years to take my own advice.
People call this approach servant leadership. I’ll accept the term as long as it stays practical. My job is to teach you about your mortgage until you understand it well enough to challenge me on it. Done right, you’ll need me less, and you’ll come back anyway. That’s how trust works. Inside the team, the same idea shows up as a rule I’ve carried since long before mortgages: the wins are shared, and the losses always have to be mine.
So look around as the site fills in. Read the guides as they land. Bring me the questions a bank once made you feel dumb for asking, whether you’re in Kelowna, somewhere else in the Okanagan, or anywhere in BC and Alberta. If we never work together, fine. You’ll still leave knowing more than you arrived with.
The look changed. The words didn’t.
A footnote, on purpose: I’m in this industry because somebody sat me down and taught me instead of judging me. Passing that along, whether it’s to the founders I mentor at UBCO, to kids on a football field, or to newer brokers trying to build something in a hard market, isn’t a side project. It’s the same job. If you’re one of those brokers, my door is open.
And if you want to hear the 2023 version of me, the episode is still up: “Empathy, Leadership and Love with Ash Simpson,” I Love Kelowna, Ep. 242.