
Jermaine Ee used ChatGPT to help his mother create a will months before she died. He launched HeirLight to bring that same clarity to other families, targeting a sector ripe for digital disruption.
Jermaine Ee spent years flying between New York and Los Angeles to see his family. When the pandemic made travel harder, he decided to move home and start a logistics company with his mother, MC. She was a vice president at a logistics firm but was underpaid, he said. Working together gave her the title and pay she deserved, and it meant more time together.
In February 2025, over lunch with his parents, Ee asked about their Roth IRA contributions. That led to a bigger conversation. His mother feared running out of money before she died. She had no will and no clear picture of her assets. Ee used ChatGPT to build a bot that asked her about accounts, belongings, and people she cared about. From that, she created a will.
Those conversations continued. Ee learned more about his mother's life. In May, the family traveled to Oklahoma City, where his parents first landed after immigrating from Malaysia 40 years ago. They visited the Burger King where she ate her first US sandwich. She only ate half because it was too expensive, Ee said. In June, they went to Salzburg, Austria – his mother's dream trip because of The Sound of Music. At the Von Trapp family home, she said she could never have imagined standing there when she watched the movie as a girl in Malaysia.
Two weeks later, she had a stroke. She and her husband were in Malaysia visiting family. She was in a coma for eight days before dying at 61.
"Losing her so unexpectedly was incredibly difficult. But it was just slightly easier because of the conversations we'd been having," Ee said. "We knew she didn't like pain and wouldn't want to be kept alive by machines."
Ee launched HeirLight on what would have been his mother's 62nd birthday last October. The company helps families have the same conversations – about assets, wishes, and end-of-life planning – using AI to guide the process.
HeirLight sits at the intersection of legal tech, fintech, and AI-assisted planning. The estate planning industry has long relied on lawyers and paperwork, but startups like HeirLight are pushing digital tools into a space that affects nearly every family. The market for online will-making and estate planning software has grown as more people seek simple, affordable alternatives to traditional legal services.
AI tools that ask questions and generate documents are not new, but applying them to sensitive, personal conversations is a newer angle. Ee's approach – using a chatbot to help his mother inventory her assets – shows how large language models can handle tasks that once required a lawyer's guidance.
For the broader sector, the readthrough is about distribution. The bottleneck is not technology, Ee said. It's getting families to start the conversation. "Clarity is love in practical form," he said.
The company is private, so no public market data is available. But the trend is visible in the broader legal tech space, where companies like LegalZoom and Trust & Will have raised venture capital and built consumer brands. HeirLight's model – combining AI with a personal story – could accelerate adoption among younger generations who are comfortable with digital tools but may not have thought about end-of-life planning.
Ee's father, now 63, has a burial plot next to his wife. Ee jokes with him about what happens if he gets a new girlfriend. The conversations continue. They are serious, Ee said, but they do not have to be heavy.
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