FairSplit: The Tech Tool That Stops Estate Fights Before They Start

Sebastian Frey

December 17, 2025
Downsizing, Technology

Why the $25 lamp your mother loved might destroy your family—and how to prevent it

Here’s a number that should make every family sit up and pay attention: 80% of families believe they won’t have conflict when dividing personal property after a death. And 80% of that 80% end up fighting—sometimes to the point of never speaking again.

Those aren’t my numbers. That’s Julie Hall, “The Estate Lady,” one of the nation’s foremost estate experts. Think about what that means: nearly two-thirds of all families end up in conflict over grandma’s china or dad’s old tools. Not the house. Not the investment accounts. Not the retirement funds that took decades to build. The stuff.

After more than 20 years helping families navigate housing transitions in the Bay Area—downsizing, estate sales, moves to be closer to kids, relocations to senior living communities—I’ve seen this play out hundreds of times. The home sells smoothly. The investment accounts get divided by formula. Then everyone stands in the living room, looking at mom’s rocking chair, and suddenly siblings who’ve loved each other for 50 years are ready to throw punches.

That’s why I want to tell you about FairSplit—a tool I genuinely wish had existed 15 years ago when I started specializing in helping seniors and their families with these transitions.

What Is FairSplit and Why Should You Care?

FairSplit is an online platform designed to help families catalog, organize, and fairly divide personal property during estates, downsizing, or divorce. Their tagline—”Divide Things, Not Families”—is a registered trademark for a reason. They mean it, and they’ve built an entire system around making it happen.

Founded by David MacMahan, who created the system after losing his father and watching family members struggle to fairly divide sentimental items, FairSplit addresses a problem that most estate attorneys, financial advisors, and even real estate agents dance around: the emotional minefield of personal property. David didn’t just identify the problem—he’s now widely recognized as the leading industry expert on estate division of personal property, having personally helped navigate family dynamics in hundreds of these situations over the past fourteen years.

The platform has been featured in The New York Times, Trust & Estates magazine, and WealthCounsel. Matt Paxton—the guy from “Hoarders” and host of “Legacy List with Matt Paxton” on PBS—sits on their board of advisors. Estate planning attorney Klea Harris, founder of the Utah Valley Women and Leadership Collaborative, is also on the board. This isn’t some fly-by-night app created by tech bros who’ve never dealt with grieving families. They hold a US patent on their division methodology and have helped thousands of families avoid the kind of conflicts that end relationships.

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The Real Problem: It’s Not About the Money

Here’s what most people don’t understand until they’re in the middle of it: estate conflicts over personal property almost never come down to monetary value. The fights aren’t about the $3,000 dining set. They’re about who gets to keep the emotional connection to mom’s Sunday dinners.

I had clients last year—let’s call them the Hendersons—who sold a $2.8 million home in Palo Alto without a single hiccup. Four siblings, all on the same page about the sale price, the listing strategy, everything. Textbook transaction. The kind of sale that makes a real estate agent sleep well at night.

Then came time to divide their mother’s personal belongings. Within three weeks, two of the siblings weren’t speaking. The issue? A set of hand-painted Christmas ornaments worth maybe $200 at an estate sale. Each sibling had memories of making those ornaments with their mother as children. Each one felt they deserved them more than the others.

This is what behavioral economists call “the endowment effect” on steroids. We don’t just value things more when we own them—we value them exponentially more when they carry emotional weight. A $25 lamp that sat on your father’s desk while he worked late to provide for the family? That lamp is priceless. And two siblings who both have those memories will both feel equally entitled to it. Neither is wrong. But only one can have it.

FairSplit’s genius is recognizing that you can’t solve emotional conflicts with purely monetary solutions. Their system separates “Emotional Value” from “Market Value”—and addresses both through different mechanisms.

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How FairSplit Actually Works: A Deep Dive

Let me walk you through the process step by step, because understanding the mechanics reveals why it’s so effective at preventing family conflict:

Step 1: AI-Powered Home Inventory

Remember when creating a home inventory meant spending 30-40 hours photographing every item, writing descriptions, and researching values? Those days are over. FairSplit launched AI-powered tools in 2024 that compress that entire process into a fraction of the time. You photograph items room by room, upload the photos, and the AI identifies items, suggests descriptions, categorizes everything, and estimates values automatically.

One user described the reaction as “Wow! We are blown away! This saved us tens of hours we expected to spend.” Having helped families navigate this process the old way—clipboards, spreadsheets, arguments about whether something counts as “furniture” or “collectibles”—I can tell you that time savings alone is worth the subscription price several times over.

The system organizes everything by property, room, category, and value. You can assign different roles to family members: administrator, lister, valuator, or observer—each with appropriate permissions. Full reporting is available in Excel, CSV, and PDF formats with photos included.

Step 2: Transparent Sharing

Here’s where family dynamics get interesting. Everyone involved gets access to view the inventory online through a private, secure account. No more “I didn’t know that was in the house” or “Why wasn’t I told about mom’s jewelry?” Everything is visible to everyone, organized by room, category, or value.

This transparency alone defuses a huge amount of conflict. Human psychology is predictable: when people feel excluded from information, they assume the worst. They imagine hidden valuables being divided in secret deals. FairSplit eliminates that suspicion by making the process radically transparent from day one.

The platform also allows you to attach files to any item—appraisals, receipts, provenance documentation, or even video recordings explaining the history and significance of sentimental pieces. Because sometimes what makes something valuable isn’t its price tag, it’s the story behind it.

Step 3: The Division Rounds

This is the patented part—the actual mechanism for fair division. FairSplit uses multiple rounds to determine who gets what, and each round serves a specific purpose:

Asset Review Round: Every participant marks items as “Yes” (interested) or “No” (not interested). This serves two purposes: it quickly identifies items that nobody wants (straight to the “sell or donate” pile without wasting time), and it flags items where multiple people have interest (requiring the next round).

Emotional Value Bidding: Here’s where FairSplit’s understanding of human psychology really shines. Each participant gets a fixed number of “emotional value points” to bid on items that matter most to them. This works like a blind auction—highest bidder wins, but nobody knows what others bid until it’s over. That $25 lamp that meant the world to dad? If you really want it, you bid high. If your sister wants it more, she’ll outbid you. The system is blind and impartial—no arguments, no accusations.

Selection Rounds: Remaining items get divided through alternating selection rounds—similar to a sports draft. The order rotates using a “snake” system (1-2-3-3-2-1) so no one has a permanent advantage. Each person ranks items in order of preference, and the algorithm assigns items based on availability and priority.

The beauty of this system is that it’s blind and mechanical. No one can accuse the executor of playing favorites. No one can claim they got cheated because someone else had inside information. The system made the decisions according to rules everyone agreed to in advance.

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Real Families, Real Results

Don’t just take my word for it. The reviews from actual FairSplit users tell the story better than I can:

One family with six siblings spread across the country and 1,000+ items to divide wrote: “The division of our mother’s estate could have been extremely contentious, divisive and protracted. It did remain inherently painful for most of us, but we had a great experience with FairSplit. The rounds went smoothly with great technical support and provided a fair, transparent process we could all trust.”

Another user with four siblings remarked that the process was “brilliant” and “there were absolutely no complaints about what each person got.” A family of twelve siblings—twelve!—successfully divided their parents’ estate using the platform. Think about the logistics of getting twelve adults to agree on anything, let alone emotionally charged personal property.

Perhaps most tellingly, one reviewer wrote: “I found it to be a Godsend. Our six siblings had been split down the middle… FairSplit made our life so much easier.” When families describe a software platform as a “Godsend,” you know it’s solving a real problem.

Why This Matters for Seniors and Their Families

In my work with seniors navigating housing transitions, I see three scenarios where FairSplit becomes invaluable:

Scenario 1: Downsizing While Still Living

Mom is moving from a 3,000 square foot house to a 1,200 square foot apartment—maybe a senior living community, maybe a smaller home closer to grandkids. She can’t take everything. Adult children have opinions about what she should keep, what they want to inherit now, and what should be sold.

FairSplit lets families make these decisions together—even when children live in different states or countries. The parent can see what items children are interested in, which helps guide decisions about what to keep, what to pass along now, and what to sell. No more flying everyone in for a weekend of arguments. No more last-minute phone calls about who gets the china.

Scenario 2: Estate Settlement After Death

The executor role is thankless. You’re grieving, you’re handling mountains of logistics, and you’re trying to keep everyone happy while making decisions that will inevitably disappoint someone. FairSplit takes the “who gets what” question off your plate and puts it into a neutral system that nobody can accuse of bias.

You can even hire FairSplit’s founder to serve as a third-party administrator, removing any potential conflict of interest if the executor is also an heir. One user specifically praised this: “Having David as the independent third party I am recusing myself as Administrator to ensure there is no real or perceived advantage.”

Scenario 3: Pre-Planning Your Own Estate

Here’s what I tell clients who are getting their affairs in order: Don’t just think about the house and the accounts. Think about the stuff. Your kids might fight over it more than anything else.

FairSplit lets you inventory everything now, attach notes about the history and significance of items, and even run the division process while you’re still alive to see the results. Want to know if your kids are going to fight over the dining room table? Find out now, while you can mediate and explain your wishes.

The platform even lets you attach videos or notes to items—preserving the stories that make things meaningful. Because honestly, the china pattern doesn’t matter by itself. What matters is that grandma served Thanksgiving dinner on it for 40 years, and there’s a chip on one plate from when you dropped it as a kid and she forgave you instantly.

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The Hidden Cost of NOT Using a System Like This

Let me be blunt: the cost of family conflict vastly exceeds the cost of any software subscription.

I’ve seen estate disputes that ended up in probate court, racking up attorney fees that exceeded the value of everything being fought over. I’ve seen siblings who stopped talking over items worth less than a nice dinner out. I’ve seen holiday gatherings ruined for years—sometimes permanently—over perceived unfairness in how mom’s jewelry was divided.

The financial cost is real, but the emotional cost is worse. Nobody lies on their deathbed saying “I’m glad I fought with my brother over mom’s vintage record collection.” But plenty of people carry regrets about relationships that fractured over things that, in hindsight, didn’t really matter.

FairSplit’s estate division plans are affordable—far less than a single hour of attorney time in most markets. Their AI home inventory subscription runs under $100 for a year. Even their premium services with a third-party administrator cost less than a few hours of legal consultation.

And they offer a 100% satisfaction guarantee—if you don’t feel it helped make your division more organized and peaceful than what you would have done otherwise, they’ll refund your money. That’s confidence in a product that comes from seeing it work thousands of times.

What FairSplit Gets Right

Having watched families navigate personal property division the old-fashioned way—spreadsheets, group texts, heated family meetings, silent treatment lasting years—I can identify exactly why FairSplit works where other approaches fail:

Neutrality: The system is blind and impartial. No one can accuse anyone of favoritism because the algorithm doesn’t play favorites. It doesn’t care who was mom’s favorite or who visited more often.

Transparency: Everyone sees the same information at the same time. No more whispered accusations about hidden items, secret deals, or unfair access.

Emotional acknowledgment: By separating emotional value from monetary value, the system honors the reality that a $50 item might mean infinitely more than a $5,000 item to the right person.

Geographic flexibility: Siblings in different time zones, different states, different countries can all participate equally. No advantage to whoever lives closest to the family home.

Documentation: Everything is recorded. The entire process creates a paper trail that can satisfy executors, attorneys, courts, and suspicious family members alike.

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When Should You Consider FairSplit?

Not every family needs FairSplit. If you have two siblings who communicate beautifully, agree on everything, and have no items with significant emotional value contested, you might be fine with a simple conversation over coffee.

But here’s my rule of thumb based on decades of experience: if any of the following apply, seriously consider using a system like this:

  • More than two heirs
  • Any history of family conflict or estrangement
  • Heirs live in different locations
  • Significant sentimental items that multiple people might want
  • An executor who is also an heir (conflict of interest concerns)
  • Previous bad experiences with family property division
  • Anyone in the family who tends toward suspicion or conflict
  • A large estate with many items to catalog and divide

If you checked even one of those boxes, the investment in a fair, neutral system will pay for itself many times over—in preserved relationships if nothing else. And relationships, unlike furniture, can’t be replaced at any price.

Bottom Line

I’ve spent two decades helping families through housing transitions. The house sale is almost never the hard part. The hard part is the human stuff—the memories, the meaning, the “who gets what.”

FairSplit solves a problem that most families don’t realize they have until they’re in the middle of it—and by then, feelings are hurt and relationships are strained. It’s one of those tools I recommend proactively, before the conflict starts, because preventing the fight is infinitely easier than resolving it.

If you’re downsizing, settling an estate, or just thinking ahead about your own affairs, take an hour and explore what FairSplit offers. Watch their tutorial videos. Read through their FAQ. See if it might work for your family.

Because at the end of the day, the stuff is just stuff. A rocking chair is wood and fabric. A set of ornaments is paint and glass. But family? Family is supposed to last forever. And any tool that helps keep families together through one of life’s hardest transitions is worth knowing about.

Learn more at www.fairsplit.com

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