For Families
September 30, 2025

More Complex By the Decade: Why Wealthy Families Are Drowning in Data (and What to Do About It)

Matt Bennetter

Family offices are swimming in data, historical records, alternative investments, PDFs from every corner of the globe, and it’s making life harder, not easier.

A recent article in FO Pro by Margaret Steen highlights this perfectly. As Matthew Espinosa, senior investment operations manager at Ford Estates, describes a common challenge:

As families grow and technology evolves, the complexity of managing a family office increases exponentially... By elevating data stewardship and making it a shared responsibility, we’re better equipped to manage the growing complexity of the family office and unlock long-term efficiencies

leafplanner founder, Josh Kanter, and his perspective:

Without a doubt, technology helps, but so does reviewing and revising that technology over time, as new solutions unwind what prior solutions did to ultimately create inadvertent complexity

Here’s the issue:

Every new tool or system is supposed to simplify operations. But in practice, it often creates new silos, workflow gaps, and integrations to manage. Cloud-based document management solved problems for a while, then added new complexity. Complexity swings like a pendulum, and family offices need strategies to stay ahead.

Alternative investments add another layer of headaches. K1s, capital calls, and unstructured data make consolidated reporting a nightmare. Espinosa calls the solution “elevating data stewardship” assigning leads to critical data points, auditing systems frequently, and revisiting workflows. Simple in concept, but it’s what keeps a family office running smoothly.

At leafplanner, we help families and family offices take control of this complexity:

  • Centralize critical information to avoid ghost trusts and lost records
  • Track responsibilities across family members and advisors
  • Streamline workflows to turn data into actionable insights

Complexity isn’t going away. But with strategy, accountability, and the right tools, you can make the pendulum swing in your favor.

Read the full article by Margaret Steen here and see how you can help your family office stay organized, efficient, and prepared for the next decade of growth.


Running a family enterprise, or managing significant wealth, can be great. However, it can also feel complex, stressful, and, at times, overwhelming.

Because if you’re the kind of family that’s managing multiple entities, investments, and advisors, everyone expects you to have all the answers. always.

And that’s okay. Navigating complexity is part of the role.

But what about the questions you don’t have an immediate answer for? For governance, you have your advisors. For investments, your wealth manager. For tech, your team.

This is where leafplanner comes in.

leafplanner is a secure, private platform built for families like yours. It’s designed to give you clarity, control, and continuity across every part of your family enterprise.

See if leafplanner is a fit for your family… Request a demo.

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