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 to crack under pressure.
At Markdale, the first thing we do is help the family build a solid digital foundation. This isn’t about tech for tech’s sake—it’s about creating clarity, consistency, and access for everyone involved.
Turning Paper Into Process
We begin by gathering all sources of financial data:
- Bank, brokerage, and credit card statements
- Tax returns, historical financial reports, legal documents
- Investment confirmations, account agreements, and more
Instead of letting these pile up in physical folders or scattered inboxes, we move them into a structured, cloud-based document system, typically organized by entity and year. Google Drive works well because it’s shareable, searchable, and easy for everyone to navigate.
We take care of coordinating with financial institutions to switch statement delivery to digital. If needed, we’ll fill out paperwork, make the calls, or provide templates for authorizations. The goal is to stop paper at the source and make sure that moving forward, everything flows into a centralized digital archive automatically.
Upgrading the Bookkeeping System
Most families rely on an informal system—an Excel spreadsheet, maybe a desktop accounting file. We migrate these into QuickBooks Online, a cloud-based bookkeeping platform that’s easy to use and built for collaboration. This allows us to:
- Reconcile bank and credit card accounts automatically
- Categorize expenses and income consistently
- Maintain books that are always current and tax-ready
We then collaborate with the family’s accountant to tailor a workflow that works for everyone. This might include setting up monthly reviews, shared access to ledgers, or custom reports for specific entities like holding companies or trusts.
Laying the Groundwork for Reporting
Once the raw data is organized, we build a workflow that keeps every part of the financial picture up to date. We use a dedicated reporting platform—Addepar—to track investments, monitor performance, and create detailed or high-level reports tailored to each family member’s needs.
We ensure that all relevant data, from banking to brokerage activity, is reflected accurately in the reports. This allows us to produce:
- Monthly or quarterly cash flow snapshots
- Real-time investment dashboards
- Custom views for specific entities, portfolios, or individuals
With consistent, reliable inputs, reporting becomes not just a formality—but a powerful tool for decision-making.
Why This Step Matters
Too often, families avoid tackling the administrative side of wealth because it feels messy or overwhelming. That’s completely understandable. But the longer disorganization goes unchecked, the harder it becomes to see the full picture—or hand things off to the next generation.
By investing in a digital foundation, families gain:
- Transparency: Everyone sees the same data, structured the same way
- Accountability: It’s easy to check what’s missing or out of date
- Peace of mind: Documents are protected, searchable, and centralized
It’s the first step in moving from reactive to proactive. And once the systems are in place, everything else—portfolio evaluation, next-gen involvement, tax prep—gets easier.
Next up: Step 2 – how we evaluate the portfolio and create clarity.
For a full look at the transformation, see our case study: From Paper Trails to Peace of Mind.
