CWM Blog

How Can Matt Help Even the Most Complicated Families with Financial Planning?

Written by Tracy Siri | Jan 14, 2026 7:49:10 PM

Ever look at your family and think, “How would anyone map out this tree?” Maybe yours is a tangled forest, roots growing in all directions, grafted branches, wild offshoots, and leaves from many seasons. And when the topic of financial planning comes up, it’s easy to wonder: Can anyone help with this much… life?

At Concierge Wealth Management, we say: Bring us your beautiful complexity! Matt’s specialty? Turning even the gnarliest family story into a legacy that thrives, supports, and celebrates every branch.

Myth-Busting: There’s No Such Thing as “Too Complicated”

First things first, so many families think their situation is the “weird one.” The truth? There is no standard-issue family, and there’s absolutely no such thing as “too complicated for planning.” Consider these common (but rarely talked about) scenarios:

  • Blended families with kids from previous marriages, all carrying their own memories… and sometimes a little baggage.
  • Siblings who haven’t shared a table in years, now suddenly facing a big inheritance decision.
  • Adult children with wildly different financial philosophies, one saving every penny, another embracing a bit of YOLO.
  • Remarried couples unsure how to honor everyone’s legacy, or parents raising kids for a relative who’s no longer in the picture.
  • Guardianship questions, step-grandparents, and “chosen family” members who provide love that’s just as strong as blood.

These stories aren’t outliers, they’re the real shape of modern family life.

 

Matt’s Approach: Grafting, Healing, and Helping Every Root Take Hold

Matt does financial planning the way a master gardener tends an heirloom orchard: gently, with curiosity, and absolutely no judgment about a little wildness. Let’s peel back the bark (metaphorically speaking) on how Matt helps:

1. Grafting New Branches

When two families blend, tension can grow where roots once ran separately. Matt’s gift is helping everyone feel connected, finding shared values, establishing family “traditions” around money, and honoring the different soils each person came from.

Example Story: A family came in after their wedding, worried about keeping everything “fair” between two sets of kids. Matt helps them design a legacy plan that values each child’s milestones, sets up a family giving day, and even starts the habit of holding big-money talks over backyard cookouts. Now, every branch feels attached to the trunk.

2. Healing Pruned Limbs and Old Wounds

Not every branch grows in harmony. Sometimes relatives are distant (emotionally or geographically), and wounds linger from past misunderstandings or decisions. Matt acts as a gentle mediator, helping everyone feel heard, translating hard legal phrasing into genuine conversation and addressing pain points directly, at a comfortable pace.

Example Story: Two brothers who haven't spoken in years inherit the family cabin. Through Matt’s patient, neutral guidance, they find a fair approach, giving one sibling summer access and the other winter, with shared upkeep. It isn't just about “splitting the property”; it's about mending old roots so future generations can make new memories.

3. Embracing Surprising Offshoots

Families grow in unexpected ways, adopted members, late-in-life marriages, bonus aunts who are family in every way but name. Matt invites everyone (not just those sharing DNA) to the planning process, so legacy reflects who you actually love and support.

Example Story: "Jessica", who calls her best friend her “sister,” wants her included as a guardian for her kids. Matt ensures their wishes are protected by drafting a plan that gets everyone up to speed, even drafting emergency instructions with a treehouse-worth of backup plans!

4. Navigating Generational Gaps and Philosophies

It’s not uncommon for older and younger branches to dream differently. Maybe one generation prioritizes tradition, another wants flexibility or philanthropy. Matt becomes translator and peacemaker, smoothing out misunderstandings and showing how one strong trunk can support many visions.

Example Story: The family spans four generations, from a WWII veteran to a college freshman. Matt facilitates open “legacy workshops,” where everyone voices their hopes and together build a plan that respects both the past and dreams for the future. The result: less argument, more laughter, and a sense that everyone’s voice matters.

The Comfort of an Advocate (Not Just an Advisor)

Matt isn’t just a number-cruncher. He’s an advocate for your values, a gentle guide for awkward conversations, and a secret superpower for any family worried they’re “too much.” Matt’s magic isn’t just in what he knows about trusts and tax rules (though he’s got that covered!); it’s how he helps every person at the table breathe a sigh of relief.

When families realize it’s not about “fitting in,” but about celebrating what makes them special, the relief is real. They leave with more confidence, and often, a few new family traditions in tow. Clarity. Understanding. Roots reconnected, branches thriving.

Ready to Let Your Family’s Roots Show?

Whether your family photo looks like a perfect redwood or more like a large shrub with ivy growing on one side, your legacy matters. At CWM, we believe complicated is just another word for “deeply human.” Matt is ready to meet you where you are, messy, wild, and absolutely welcome.

Reach out anytime. No need to prune your story to fit; we’ve got tools (and plenty of coffee) to help every branch grow just as it was meant to.

Ready to see what your family tree could look like, with every branch honored, roots healed, and your unique story thriving for generations? Matt’s at your side, rooting for you.

Let’s get growing! 🌱

 

FAQ: Financial Planning for Complicated Families at CWM