Discovering Hidden Assets: The TurboTax-Inspired Tool Simplifying Estate Settlements

Davis Wilkinson transformed his camping trip reflections into a groundbreaking venture with Heirloom, a self-help software for estate executors. This Wantrepreneur to Entrepreneur Spotlight highlights how Davis turned inspiration from the book "Designing Your Life" into a tool that eases the probate process by maximizing inheritances and minimizing stress. His journey was validated when his first customer, his aunt, experienced firsthand the relief Heirloom provides. Davis's story is a testament to the power of nature, resilience, and the drive to offer real value, turning a personal insight into a solution that supports families during challenging times.

Hi, Davis Wilkinson! Thanks for joining us today. Tell us about your business. Who do you serve, how do you serve them, and what's the impact that your business and work makes?

Heirloom is self-help software for estate executors, like the "TurboTax of probate." We help families maximize their inheritance, save time, and reduce stress. Heirloom's asset discovery tools search 120 billion records, 6,000+ databases, and other sources to find property, accounts, life insurance, and other assets that loved ones left behind. Heirloom also curates a personalized executor guide for estate settlement, tailored to the details and jurisdiction of a loved one’s estate. A beneficiary portal, work log, and other features simplify communication with family members and generally help executors manage the probate process.

Tell us about the moment you finally felt like you went from wantrepreneur to entrepreneur.

Heirloom's first paying customer was my aunt. Hearing how she described Heirloom's impact on her life was such a meaningful milestone, validating my entrepreneurial journey: "Heirloom makes all the difference. In the midst of everything going on, it's a relief to know I have a plan and tools to help me."

Describe the moment or period in your life/career that motivated you to make the entrepreneurial leap.

It may sound a little dramatic, but I went on a camping trip with my dog to Central Oregon and read the book, "Designing Your Life." Working through the book's exercises clarified my desire to take the entrepreneurial leap and helped me identify the problem spaces I would be passionate about solving. I personally have found power in "unplugging" and getting out in nature when looking for direction in my life. 

Describe a tool, service, or software that has been a game-changer for your business. How does it contribute to your success?

It's trite, but Cursor + Claude for software development. It has magnified our team's velocity by multiples and helped us build products more efficiently.

We know that success is very often a non-linear path. Tell us about a failure, pivot point, or lesson that changed your course or direction and helped to get you where you are today.

My first job out of college required lots of hours. I got sucked into the grind and didn't take care of my physical or mental health, which meaningfully impacted my performance for a time. I had to learn the hard way (lots of failures) that if I don't take care of my health, I simply can't perform well. This lesson has been a gift throughout my career since, and helps me to consistently be productive at Heirloom. And even if there weren't productivity gains to happiness, what would be the point of work if it didn't foster joy, meaning, and health?

What unconventional strategy did you employ that significantly impacted your business?

I like this question since it embodies the entrepreneurial ethos of thinking differently. Unfortunately, I'm not sure if I have an interesting answer at this point. The truth is we've tried to follow the innovation playbook pretty closely at Heirloom. It seems to me that sometimes the same old answers exist for a reason - they work. So, we experiment quickly, listen to our customers, and concern ourselves more with providing value to our users than competing with our peers. These tried-and-true principles have served us well thus far. 

What’s something you wish you knew sooner that you’d give as advice for aspiring or newer entrepreneurs?

This may sound disappointingly simple, but I just wish my younger self knew that the learning really begins when you ask people to buy your product. It's easy to get lost in hypothetical product discovery techniques, concept comparison exercises, and other high-minded methods for finding product-market fit. But in my experience, the rubber hits the road when you show people what you've got and see if they'll pay for it. The sooner you can get to that moment, the faster you'll get to the cold hard truth. 

Want to dive deeper into Davis's work? Check out the links below!

• Visit Heirloom's website: heirloom.care