Heirloom's Origin Story: Davis Wilkinson on The Wantrepreneur to Entrepreneur Podcast

Last Friday, Heirloom Co-founder and CEO Davis Wilkinson joined host Brian Lofrumento on The Wantrepreneur to Entrepreneur Podcast to share the personal story behind Heirloom and why estate settlement is long overdue for a modern, compassionate solution. In episode 1409, “Solving a Broken System: The Origin Story of Heirloom, the ‘TurboTax for Probate’,” Davis walks through the family experience that inspired Heirloom, the unconventional steps he took to understand the problem, and how his team is building tools that truly serve grieving families.

You can listen to the full episode on the Wantrepreneur to Entrepreneur website or watch it on YouTube.

The personal story behind Heirloom

Heirloom began with a painful, deeply personal experience. After the loss of his brother, Davis watched his mother struggle through a maze of paperwork, court requirements, and asset searches while grieving. The process was confusing, fragmented, and emotionally draining—yet it’s one that millions of families are asked to navigate every year.

Instead of assuming he understood the problem from the outside, Davis made a deliberate choice to get as close to it as possible. He took a job as a funeral home receptionist, answering calls from families in crisis and seeing firsthand how overwhelming the logistics of death can be. That experience, combined with his background in product, venture capital, and data privacy, led to a simple but powerful question: What if there were a “TurboTax for probate” that helped ordinary families settle estates with clarity, confidence, and care?

Heirloom is the answer to that question—a self-help platform for estate executors that combines step-by-step guidance with powerful asset discovery tools.

Key themes from the conversation

Founder–market fit through empathy

In the episode, Davis talks about the importance of immersion over assumptions. Rather than starting with a pitch deck, he started by listening—sitting with families, talking to funeral directors, and observing the day-to-day friction in estate settlement.

That empathy-first approach is now baked into Heirloom’s product. From the initial intake questionnaire to the personalized executor roadmap, every feature is designed to reduce cognitive load at a time when most people are already overwhelmed.

Being a scientist, not just a visionary

Davis also shares why he sees himself less as a visionary and more as a scientist. Vision is important, but the real progress comes from running experiments, gathering data, and being willing to be wrong quickly.

On the podcast, he emphasizes that building a company is a process of constant learning. At Heirloom, that mindset shows up in how the team iterates on onboarding flows, tests new asset discovery methods, and refines guidance based on real executor outcomes—not just intuition.

Managing the emotional weight of entrepreneurship

The conversation also touches on the emotional side of building a mission-driven company. Working in the world of death, grief, and estates can be heavy—and so can the uncertainty of entrepreneurship.

Davis shares how practices like meditation, mindfulness, and focusing on what can be controlled help him navigate that weight:

“Am I worrying about the future too much? Am I worrying about the past too much? And instead, should I just be in the present and think about what I can do today, this hour, this moment to try and move the needle for my team?”

That same mindset informs how Heirloom supports executors: break the process into clear, manageable steps and focus on what needs to happen in the now.

How this ties back to Heirloom’s mission

For many families, settling a loved one’s estate is the most complex financial and legal process they will ever face—and they’re asked to do it while grieving. Heirloom was built to change that.

Today, Heirloom helps executors:

• Discover hidden assets with search tools that scan more than 120 billion records across 6,000+ databases to find property, accounts, life insurance, and other assets that might otherwise be missed.
• Follow a personalized executor roadmap that adapts to the estate’s details and jurisdiction, so executors always know what to do next.
• Stay organized and accountable with a work log, document storage, and clear records of communications and decisions.
• Reduce conflict and confusion by giving beneficiaries a transparent way to see what’s happening and why.

The podcast episode is, at its core, a story about why this work matters—and how technology, used thoughtfully, can make one of life’s hardest chapters a little easier.

Listen to the episode and learn more

If you’d like to hear the full conversation, you can:

• Listen on the Wantrepreneur to Entrepreneur episode page
• Watch on YouTube
• Read the Wantrepreneur to Entrepreneur spotlight on Davis and Heirloom

To learn more about Heirloom or share it with someone settling a loved one’s estate:

• Visit the Heirloom website
• Explore more articles on the Heirloom blog
• Connect with Davis on LinkedIn

We’re grateful to Brian and The Wantrepreneur to Entrepreneur Podcast community for shining a light on the broken parts of the estate system—and on the founders, families, and builders working to fix it.