With more Canadians reconsidering their U.S. vacation homes and accountants looking for smarter ways to manage complex portfolios, tech-driven financial tools are becoming more important than ever. I recently sat down with Brian McGlynn, CEO of Wealth Write.Up, to talk about some of the trends he’s seeing — from real estate exits to AI-powered accounting.

Why Are Canadians Selling Their U.S. Properties?

Let’s start with a trend that’s been gaining traction: Canadians offloading real estate in the U.S.

“People are rethinking their ties to the U.S.,” Brian said. “There’s the political tension, tariffs, and a growing sense of nationalism — plus the dollar exchange makes maintaining a U.S. property much more expensive.”

For snowbirds or real estate investors, the lower loonie means every cost — from mortgage payments to maintenance — hits harder. And for those with properties that aren’t generating income, the pressure to sell can be even higher.

But it’s not as simple as just listing and selling.

“There are serious tax implications,” Brian explained. “Especially when you’re dealing with foreign property sales, capital gains, trusts, and repatriating funds back to Canada. That’s where our software helps. It gives accountants the tools to model different scenarios and help clients decide the best time and method to sell.”

What Exactly Is Wealth Write.Up?

Wealth Write.Up is the cloud-based evolution of TJPS — software that’s been helping Canadian accountants manage complex investment accounting for over 25 years. The “Write.Up” part refers to both increasing value and the detailed reporting of yearly transactions like buying or selling stocks, real estate, crypto, or other investments.

“We help with the ‘what-if’ scenarios,” Brian said. “Let’s say someone sells a U.S. rental. Our tools help accountants figure out the tax impact — not just now, but also what happens if that money gets reinvested or passed down to the next generation.”

Enter AI: The Future of Smart Accounting

Everyone’s talking about AI, and Wealth Write.Up is no exception. But Brian is careful not to treat it like a magic button.

“A lot of companies think of AI as just a feature,” he said. “We think of it as a platform. It’s not about replacing accountants — it’s about empowering them.”

Currently, they’re using AI for things like data migration, pattern recognition, and even cleaning up messy spreadsheets. Down the line, they’re looking at more advanced uses, like offering predictive insights or flagging things accountants might want to take a closer look at.

“Think of AI as a really smart assistant,” Brian said. “It handles the repetitive stuff so professionals can focus on strategy and advice. That’s what clients really value — not the hours spent formatting data, but the answers and insights.”

The Rise of Family Offices in Canada

Another trend Brian pointed out? The growth of family offices — especially multi-family ones — as generational wealth continues to rise in Canada.

“With more households approaching the million-dollar mark in assets — and many with much more — people are grouping together to get expert guidance on how to manage, protect, and pass down their wealth,” he said.

Younger generations, especially digital natives, are demanding more tech-savvy service. They expect answers fast. They expect tools that work. And they’re looking for professionals who understand both the numbers and the software behind them.

Final Thoughts

As Canadians rethink their investments and real estate holdings, and as wealth grows more complex, it’s clear that technology will play a key role in how we manage it all. Whether it’s AI speeding up the accounting process or tools like Wealth Write.Up offering deeper insights, one thing is certain: the firms that modernize are the ones that will thrive.

As Brian put it best, “You want to be Netflix, not Blockbuster.”

Sean Cooper is the bestselling author of the book, Burn Your Mortgage: The Simple, Powerful Path to Financial Freedom for Canadians, available now on Amazon and at Chapters, Indigo and major bookstores, and as an Audiobook on Amazon, Audible and iTunes.