Author: Caliya Connor

  • Emotions and Investing: What’s More Important: How You Feel or What You Earn?

    Emotions and Investing: What’s More Important: How You Feel or What You Earn?

    Many novice investors assume the goal is simple: “make the most money”. But things rarely turn out this way. Even though we want the best outcomes, we often make decisions that that prioritize emotional comfort instead. Whether it’s the desire for peace of mind, fear of loss, or a need for control, emotions can be

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  • Income That’s Built to Last

    Income That’s Built to Last

    Step 4 – Why Selling Assets Shouldn’t Be Your Income Plan When a portfolio needs to fund a lifestyle, many investors fall into a quiet trap: generating cash by selling off assets. On the surface, it seems harmless. And, it might even align with “total return investing”. But over time, drawing on your capital base can

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  • Restructuring Fees and Aligning Incentives

    Restructuring Fees and Aligning Incentives

    Step 3 – The Real Cost of Complexity When we conducted a full audit of the family’s portfolio, the most jaw-dropping figure wasn’t performance-related. It was the fees: $330,000 per year. And they weren’t even getting full value for it—until we began restructuring fees to reflect the actual value being delivered. That amount was spread

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  • Bringing the Portfolio Into Focus

    Bringing the Portfolio Into Focus

    Step 2 – If You Can’t See It, You Can’t Manage It After setting a clear investment strategy with the family, the next question was straightforward, but daunting: What exactly are we working with? The family’s assets were spread across three different investment advisors, each using their own custodians, platforms, and reporting systems. There was

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  • When Wealth Grows, Strategy Matters Even More

    When Wealth Grows, Strategy Matters Even More

    Step 1 – Creating a Strategy That Reflects the Family’s Goals When this family approached us, they weren’t in crisis. Their $110 million portfolio was diversified. On paper, it seemed like they were doing most things well. However, despite having three investment advisors at wealth management firms, they lacked one essential thing, a unified strategy.

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  • Step 3: Involve the Next Generation

    Step 3: Involve the Next Generation

    Once systems are in place and the portfolio is clearly understood, the next natural step is often the hardest to approach: preparing the next generation. In many families we work with, adult children and spouses are kept at arm’s length from the finances—not out of secrecy, but out of habit. The older generation may have

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  • Step 2: Evaluate the Portfolio and Create Clarity

    Step 2: Evaluate the Portfolio and Create Clarity

    Once a family’s financial records are organized and flowing smoothly, we shift our focus to what matters most: to evaluate the portfolio and ensure the investments are doing their job. Often, the issue isn’t a lack of effort—it’s a lack of visibility. Holdings are spread across institutions, account types, and asset classes, with no unified

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  • Step 1: Build the Digital Foundation

    Step 1: Build the Digital Foundation

    When we meet a new family, we often find decades of wealth management held together by habit: statements in a filing cabinet, handwritten notes on envelopes, maybe a few spreadsheets passed between generations. These systems worked—until they didn’t. As families grow more complex, the need for a digital foundation becomes clear, as paper-based approaches start

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  • Behind the Reports: How We Set Up Addepar

    Behind the Reports: How We Set Up Addepar

    At Markdale, we believe in meeting you where you are—and organizing your financial life so it’s easy to understand and manage. That’s why we use Addepar as the foundation for our reporting. But before we can generate beautiful reports and dashboards, there’s some behind-the-scenes work that happens first. Here’s how it works: 1. We start

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  • When Diversification Backfires, Streamlined Stewardship Steps In

    When Diversification Backfires, Streamlined Stewardship Steps In

    Case Study: How One Family Reclaimed Control of Their $30M Portfolio A client came to us with a $30 million portfolio spread across three investment advisors. On the surface, everything seemed in order—diversified across Canadian and U.S. equities, fixed income, real estate, alternatives, and cash. A textbook case of manager diversification. But beneath the surface,

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