What AI Changed—and What It Didn’t—for Founders (feat. Jermaine Ee)
The conversation highlights how modern software building is shifting from pure technical execution to clarity, trust, and resourcefulness.
When I sat down to speak with Jermaine Ee from HeirLight, I expected a conversation about software, startups, and maybe a bit about AI. What I didn’t expect was how much it would challenge the way I think about why we build things in the first place.
Jermaine is a non-technical founder by background, but that label almost feels misleading. He understands systems, architecture, and product trade-offs deeply—just without writing code himself. What stood out to me immediately was that he didn’t arrive at software because he wanted to build software. He arrived there because he wanted to solve a human problem.
That distinction matters more now than it ever has.
Podcast
What Jermaine Taught Me About Clarity, Software, and the Future of Work - on Apple and Spotify.
Following Curiosity Instead of a Playbook
Jermaine’s career doesn’t follow a neat arc. He’s worked in toys, logistics, political finance, and now legal tech. At first glance, it looks scattered. But as he explained it, the common thread is curiosity. Every time he noticed something broken or unclear, he followed that thread until it turned into a business.
HeirLight came from a conversation with his parents—immigrants who carried a quiet, persistent anxiety about money, aging, and what happens when clarity runs out before life does. Jermaine didn’t start with a legal tech roadmap. He started by trying to preserve stories and meaning through a chatbot. Only later did he realize that, with the right information, he could help people create wills, health directives, and powers of attorney in a way that felt humane instead of intimidating .
That evolution stuck with me. Too often, founders go looking for problems that fit technology. Jermaine did the opposite.
AI Didn’t Replace Engineers—It Changed What Matters
One of the most honest moments in our conversation came when I asked whether AI made it possible for a non-technical founder to build a software company alone.
His answer was simple: no.
AI didn’t remove the need for engineers—it changed the definition of a good one. Code generation tools have dramatically reduced the need for junior developers whose primary value is output volume. What matters now is resourcefulness: the ability to evaluate trade-offs, architect systems, understand constraints, and decide what not to build.
When Jermaine hires engineers, he’s not looking for perfect résumés or conventional career paths. He’s looking for people who took risks, deviated from expectations, and can reason creatively under uncertainty. That mindset shows up in how they design systems, not just how they write code.
As someone who has spent years around engineers, that resonated deeply with me.
Product Decisions Should Follow Trust, Not Taste
One of my favorite insights from Jermaine was how HeirLight approaches its tech stack. The choices weren’t driven by personal preference or what’s trendy. They were driven by trust.
When you’re asking users to share their most private information, security and data integrity aren’t features—they’re the product. Even design decisions followed that logic. The team removed beautiful animations from their landing page when heatmaps showed users weren’t reading critical explanations about security and intent. Conversion and clarity mattered more than aesthetics.
That’s a lesson I wish more founders—technical and non-technical—took to heart.
Selling Is About Patterns, Not Playbooks
Sales turned out to be just as thoughtful as the product.
Jermaine doesn’t believe in repeating last quarter’s “best practices.” Attention shifts too quickly. Instead, his team looks for underpriced attention—places where trust can be built before the channel becomes crowded or expensive.
Right now, that means organic content and podcasts. Long-form conversations, like the one we had, allow founders to build credibility with people who are already going through life transitions—career changes, parenthood, loss, or financial responsibility. Those are the moments when clarity actually matters.
What struck me most is that Jermaine isn’t trying to convince people they need a will. They already know. He’s speaking to the real blocker: procrastination driven by fear, complexity, and cost.
That’s not marketing. That’s empathy.
A Broader Reflection on Work and Identity
Toward the end of our conversation, we moved away from startups and into something more personal: identity, immigration, and gratitude.
Jermaine talked about growing up Malaysian-Chinese in the U.S., learning to assimilate early, and only later rediscovering the value of cultural hybridity. Malaysia, as he described it, is a place where diversity isn’t a slogan—it’s daily life. Different religions, languages, and histories coexist without constant friction.
Listening to him, I was reminded how easy it is—especially in tech—to reduce people to roles, résumés, or outputs. But the most interesting builders I’ve met are shaped by their lived experiences far outside work.
What I’m Taking With Me
This conversation reinforced something I’ve been feeling for a while:
Software is becoming cheaper to build, but harder to build well.
Technical skill is table stakes; judgment and resourcefulness are differentiators.
Trust, not technology, is the real moat.
And clarity—whether in code, products, or life—is one of the most undervalued forms of care.
Jermaine didn’t just talk about building a company. He talked about building something that helps people face the uncomfortable parts of life with a little more confidence.
That’s the kind of software future I want to be part of.