In this episode of Not Ready Yet: Curating Conversations for the Aging Journey, Lisa Harper speaks with David MacMahan, founder of FairSplit.com, about the emotional complexities of dividing personal belongings during estate settlements. David shares his personal experiences that led him to create FairSplit, a platform designed to help families navigate the often difficult process of estate division with transparency and fairness. The conversation covers the importance of estate planning, the emotional attachments to belongings, and how AI technology can streamline the inventory process. David explains the FairSplit system, which allows families to list items, express their preferences, and ultimately divide belongings in a way that minimizes conflict. The episode emphasizes the need for open conversations about aging and estate planning, providing listeners with valuable insights and resources to prepare for these challenging discussions.

Takeaways

• David MacMahan founded FairSplit to help families divide belongings peacefully.
• Personal experiences with loss inspired David to create a better system for estate division.
• Transparency in estate planning can prevent conflicts among heirs.
• AI technology significantly reduces the time needed to inventory belongings.
• Emotional attachments to items can complicate the division process.
• Families often underestimate the overwhelm of estate division without a system.
• FairSplit allows for a structured and fair way to divide personal property.
• The emotional value of items often outweighs their monetary value.
• Open conversations about aging and estate planning are crucial for families.
• Utilizing technology can ease the burden of estate management.

Chapters

00:00 Introduction to FairSplit and David MacMahan
01:43 The Emotional Dynamics of Estate Division
04:50 Personal Stories Behind the Passion
06:16 The Importance of Estate Planning
08:45 Utilizing AI for Home Inventory
10:22 Legal Considerations in Estate Division
11:29 The Value of Sentimental Items
14:24 Understanding True Value in Estates
19:19 How FairSplit Works
23:56 Navigating Family Divisions and Fairness
25:17 The Role of AI in Estate Management
26:51 Overcoming the Overwhelm of Moving
27:34 Engaging Family in the Process
29:19 Utilizing Technology for Inventory Management
30:48 Setting Expectations and Responsibilities
32:56 Avoiding Conflicts in Estate Division
33:51 Resources for Executors and Families
38:10 Promoting Transparency and Fairness
42:44 Proactive Planning for Family Assets

Resources

PROMO Code NRYTRYAI for the Starter Inventory ($79.99 value) found here: https://www.fairsplit.com/plans/home-inventory/

Resources Page for Sample Letter of Instruction and 5 Tips to avoid conflict in estates: https://www.fairsplit.com/helpful-tips-and-videos/

YouTube Channel for Dividing Things with David and other tips: https://www.youtube.com/@DivvyMaster

Printable flyers on this page: https://www.fairsplit.com/resources/printables/


Keywords

FairSplit, estate planning, emotional attachments, AI inventory, family conflict, personal belongings, estate division, downsizing, family resources, transparency

© 2025 Lisa M. Harper. All rights reserved. “Not Ready Yet: Curating Conversations for the Aging Journey” is a trademark of Lisa M. Harper.