Author: Caliya Connor

  • 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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  • A Modern Family Office Transformation

    A Modern Family Office Transformation

    Case Study: From Paper Trails to Peace of Mind When we meet families like this one, we often find a familiar story. Wealth built over time through hard work and intuition, now managed with the same habits that once served well—but are beginning to show their limits. It’s at this crossroads that family office transformation…

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  • A Personal CFO is Like a Personal Chef

    A Personal CFO is Like a Personal Chef

    Imagine walking into your kitchen each evening to find your dinner already prepared—tailored to your tastes, diet, and health goals. Everything is ready: the ingredients sourced, the appliances maintained, and the table set with care. All you have to do is sit down and enjoy. That’s what it feels like to have a personal chef—and…

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  • How Our Family Office Helps Wealth Stewards Transition with Peace of Mind

    How Our Family Office Helps Wealth Stewards Transition with Peace of Mind

    As families grow in both size and wealth, the systems that once supported their financial lives often start to show strain. This is especially true for baby boomers who have spent decades managing their estates using familiar—but increasingly outdated—approaches. In some cases, families with significant wealth are still relying on paper files, with long-time administrators…

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  • Effortless Financial Management: Simplify with Automation

    Effortless Financial Management: Simplify with Automation

    Wealthy investors often have complex financial lives, with multiple bank accounts, brokerage accounts, and credit card statements that need to be carefully documented and reconciled. Our bookkeeping and record-keeping service is designed to bring clarity and efficiency to this process. We ensure that all financial statements are saved in an organized digital system, accessible to…

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