Jermaine Ee on Scaling an AI-Powered Startup, Designing for the 70%, and Not Getting to Choose Your Founder Story
In Brief: Jermaine Ee, founder of Heirlight (heirlight.com), an AI-powered estate planning app, joins host Dan Freehling to discuss what it takes to make one of life's most avoided conversations easier. Jermaine shares how a dinner with his parents about retirement planted the seed for Heirlight (02:37) and how the app uses guided AI conversation rather than a laundry list of assets to build an estate plan around the user (04:53). He also describes his deliberate choice to stay bootstrapped and away from the venture treadmill (15:35), the mentality required to run a product-driven startup (21:38), and how losing his mother gave his mission a clarity he didn't ask for but can't ignore (22:56).
Recommended reading: “Essentialism” by Greg McKeown, “Die with Zero” by Bill Perkins, and “Predictably Irrational” by Dan Ariely.
Transcript
Dan Freehling (00:05):
Hey everyone, Dan here. Welcome to another episode of Forward-Looking Leadership. Today I'm honored to be joined by Jermaine Ee. Jermaine is a tech entrepreneur building Heirlight, an AI-powered app designed to make estate planning faster and more accessible. Jermaine, thanks so much for joining me.
Jermaine Ee (00:23):
Glad to be here, Dan.
Dan Freehling (00:25):
Thanks for taking the time. You say that clarity is love in practical form, and I think that's a beautiful sentiment. I'd love for you to explain how that led to the founding of Heirlight.
Jermaine Ee (00:38):
Clarity is something I think we can all use a little more of, because a lot of us live life on autopilot. We inherit the values, the cultural norms, the societal acceptance of everything around us — from money to health, to how we eat, how we dress. "Clarity is love in practical form" stems from the idea that if we question ourselves a little more about why we do what we do, and get clearer on what matters and whose validation we're seeking, we're able to live a life that's more grounded and more true to who we are.
Dan Freehling (01:27):
How did this come about for you personally, in your journey as an entrepreneur?
Jermaine Ee (01:33):
It's a newer thing for me. All through my 20s — I'm in my mid-30s now — I chased the headlines. I wanted to be in a TechCrunch or Business Insider article that said "Jermaine, founder of X, raised X amount at X valuation." That's the dream of this Silicon Valley life, even when you're not physically in Silicon Valley.
(02:37) As I got a little older and traveled more, I started noticing things. When I first started learning Spanish in Mexico, I learned there are two ways to say "happy." There's feliz, as in Feliz Navidad, and then there's contento, which translates to content. In our culture, we don't think about contentment much. We treat happiness as a pursuit, an act. That clicked for me during a conversation with my parents over Thai food near my office. I asked them why they weren't thinking more about retirement — not telling them to stop working, because it's fulfilling for them, but what about everything else? What I realized was that they had no clear sense of how their 401k translated into the rest of their lives. And for most people, that's true. And underneath that is a real uneasiness: what if I run out of money before I die? That uneasiness is at the core of what Heirlight started as.
(03:34) Heirlight was built initially as a chatbot to take life's inventory — to help my mother have a conversation with an ego-free, unbiased, judgment-free AI agent about the things she cared about: her relationships, her assets, her bucket list. Things we don't normally talk about over lunch. A few months in, I realized that if I had your assets and your relationships, I could create an estate plan for you. So we started working on the legal side, making sure we'd guardrailed our AI. It doesn't just say yes to everything or do whatever you ask — it pushes back and asks clarifying questions. The product today is live in California. Depending on when you're listening, we may be expanding to the rest of the country. Each state has different laws governing the probate code and health directives, so we're working through those legal hurdles now.
Dan Freehling (04:47):
Walk me as a layperson through how you built this and what it entails technologically.
Jermaine Ee (04:53):
It's a mobile app. When you log in, you're greeted by Faye, a firefly character we designed as the app's agent. You talk to Faye, and as you do, she picks up on things. There's a concept in probate law called the gift of residue — in plain terms, it means "everything else." When you write a will, you list your things and who gets what. But we approach it in reverse. Instead of hammering you with "You have a watch, who gets the watch? You have a car, who gets the car?" we ask you first: who are the most important people in your life? Who can make decisions for you? As you answer those questions conversationally, the app is building a picture of your world. So when you then ask "What is an executor?", the app can answer you in the context of everything it already knows about you.
Dan Freehling (06:39):
I can see the utility of this. How did you go about building it — the code, the chatbot, the legal knowledge?
Jermaine Ee (06:55):
On the coding side, I have two incredible co-founders. Mikey handles the AI, and ZJ builds everything we want to visualize. On top of that, we have a design advisor who works at Spotify and a design team for UI/UX. It's now a seven-person operation.
(07:20) On the legal side, the probate code is publicly published for every state — it governs what happens to everything in your life when someone passes. What varies by state is the interpretation and the specific language your will needs in order to be legally valid. There are plenty of companies already doing parts of this: you can download a template, or use LegalZoom, or an excellent company called Trust & Will. I consider them competitors, but I genuinely believe rising tides raise all boats. Seventy percent of Americans don't have an estate plan — there's plenty to go around.
(08:30) What we've done is work with local attorneys to build a sophisticated template. When our AI chats with users, we're filling in that template as clearly as possible so that the person's intentions are fully reflected in the document. Like all apps in this space, we're not permitted to give legal advice. We give users the best practices available based on their context, and they make the choices.
Dan Freehling (09:03):
And this produces a will they can actually put into practice?
Jermaine Ee (09:11):
Yes. Every state is a little different, but typically if you print a will and sign it in front of two witnesses, it's valid. Some states — California, I believe — require everyone to be in the same room looking at each other directly. Not legal advice; if you have questions, consult an attorney. But we'll give you instructions specific to your state on what makes it legally valid.
(09:46) A will is simply a document the court uses after someone passes to determine who gets what and who's appointed executor — the person who carries out the wishes. Many people actually need a trust, which is a legal entity that holds your assets and allows them to pass without going through probate court. If you already know the difference between a will and a trust, you probably need a trust. But I built Heirlight for the average person who has no idea about any of this. That person was me just a year ago.
Dan Freehling (10:32):
What did you do to get up to speed on wills, trusts, and estate law?
Jermaine Ee (10:39):
A lot of conversations with attorneys. They typically spend the first 20 minutes telling me this is too complicated, that AI can't do it, that an app can't do it. After I explain what lane we're actually playing in, some come around and some never do. I've had some uncomfortable conversations where I felt like a punching bag for 30 minutes about how technology is destroying legal drafting — and honestly, I understand where they're coming from. What I've learned is to quickly gauge whether an attorney is open to an alternative solution for people who simply cannot afford them. We now have 22 attorneys we bounce ideas off, send template drafts to, and consult on specific questions. I also have one attorney dedicated to making sure I'm not accidentally giving legal advice.
Dan Freehling (12:00):
Why should people trust your service with something this important?
Jermaine Ee (12:08):
Honestly, I think they should evaluate it. Look at my track record. Do the research. My bigger concern isn't the user who's already doing their homework. I'm trying to get people from zero to one.
(12:30) A lot of young people say, "I don't have much — why do I need a will?" But there's another document called the healthcare directive. It governs what happens to your body when you can't make decisions but you're not yet dead — you're unconscious, in a coma, unable to speak for yourself. Who makes decisions for your body? Without this document, you leave it to medical professionals or, worse, you leave it to your family to fight over. There was an actress a few years ago whose husband knew she would want to be let go if she were in a vegetative state, but it wasn't in writing. Her parents disagreed. They fought her husband for six years. Six years of emotional, legal, and financial stress — for a document that, through Heirlight, takes about 10 minutes to complete. The AI doesn't judge. It has no bias. It's likely the easiest way to get it done.
(14:13) One of our biggest current challenges: we promise users they'll leave with an estate plan, but I'd love to also be able to refer them to an attorney when they need one. There are ethical and regulatory complications around referrals and fee-splitting, so even setting those aside, the price jump is stark — we charge $179, while a trust done by an attorney in Los Angeles or Boston can run $1,500 or more. For users who genuinely need a trust, I don't yet have a good solution, because getting a trust funded involves a lot of work outside the app.
Dan Freehling (15:20):
You've founded other startups and projects before this. What have you most drastically changed your mind on between your first time founding and founding Heirlight?
Jermaine Ee (15:35):
The most drastic shift is how I handle external perception of my business. A younger version of me spent a lot of energy making the business look bigger than it was — because there's a real case to be made that success attracts success. When you look successful, more things come your way. But at this stage, I've turned down investors because I understand that if I start raising and play the venture capital game, I'm on an 18-month fundraising treadmill, constantly hitting metrics. And worst of all, I'd lose some mental autonomy. I'd care what the people I took money from thought about my direction, and being a non-confrontational person, I know that would affect me. Getting more self-aware as a founder has shaped the kind of business I want to run.
Dan Freehling (17:00):
Have you taken venture money for previous projects?
Jermaine Ee (17:04):
I have, mostly at the pre-seed stage — very early, before a strong product. Back then, pre-seed rounds were $50,000 to $75,000. These days they can go up to $2 million. If I were to raise $2 million for Heirlight, I'd give up roughly 18% of the company. I'm not sure I want that dilution in exchange for capital I honestly don't know what I'd use for right now. I have what I need to build.
Dan Freehling (17:57):
What would you say to aspiring founders thinking through whether to pursue VC or bootstrap?
Jermaine Ee (18:11):
First question: why are you building this? Is it a passion project? Are you chasing something? Then understand what different funding types actually require. A lot of businesses could be funded with an SBA loan at low interest rather than venture capital. To play the VC game, you need to be building something that can scale to hundreds of millions. I think there's a real lack of understanding of how venture firms actually work. The power law says that in a typical 10-year fund, maybe two to five out of a hundred investments generate returns that cover all the others. A good venture firm will only bet on companies that have a shot at being in that five percent. If you're building a services business, venture is almost certainly not the right fit. Heirlight itself may end up being more of a private equity story — a fund for performance marketing to amplify growth, maybe a strategic roll-up with a life insurance or money management company. I'm not sure we'll ever reach a billion-dollar valuation, and I'm not sure I want to.
Dan Freehling (20:07):
When would private equity get interesting to you?
Jermaine Ee (20:17):
If it's strategic. A roll-up that pairs Heirlight with a life insurance company or a wealth management firm would make sense — there's real synergy there. Short of a strategic play, though, I think we can grow well just by maintaining a healthy ratio of customer acquisition cost to lifetime value.
Dan Freehling (21:13):
How do you think about managing differently across your different ventures? You're running Heirlight, which is a product-driven company, but you're also running your mother's logistics company. How do you shift gears as a leader between those two very different entities?
Jermaine Ee (21:38):
For context, my mom passed away exactly five months ago today, and she and I had a small business together. In a business like that, free cash flow is everything — how much comes in and out, and what that allows you to grow or take home. Tight bookkeeping, accounts payable and receivable under control, clear SOPs. It's operationally heavy. Heirlight is product-driven: build the best product, focus on design, get more attention. Very different gears, very different kinds of motivation. When I wake up and think about both, sometimes I have to check in with myself — which mode am I in today?
Dan Freehling (22:46):
Do you mind sharing a bit about your personal journey with losing your mother, and what that experience was like for you?
Jermaine Ee (22:56):
I think this process has been extremely rewarding already, because building Heirlight meant I was having real conversations with my mom — about the things she cared about, the relationships she valued. Because of those conversations, I got to know her more. That is ultimately the goal of Heirlight: helping people have those conversations. It circles back to where we started — clarity is love in practical form. If you love someone, you can cook for them, hug them, tell them. But you can also help them gain clarity about their life.
(23:30) With her passing, I never asked for this founder story or this mission. But in some ways, it's what she left me. I don't really get to choose. I'm building this in her honor, and she keeps me focused. When a decision is unclear, I can always go back to why we started, and that mission is very clear to me.
Dan Freehling (24:24):
Thank you for sharing that. And it really does bring tremendous clarity into business decisions — having such a real and visceral reason for starting something cuts through a lot of the noise.
Jermaine Ee (24:43):
That's what I challenge most people to do, even if they just have a job. One simple exercise: look at your calendar or your bank account from the last 30 days. Highlight the things that added energy to you. Circle the ones that took energy away. Do more of the former. It's subjective to everyone, but it's never not useful.
Dan Freehling (25:15):
What have you personally started doing more or less of?
Jermaine Ee (25:22):
I've started slowing down a lot more. I'm a workaholic — I genuinely love being in the office on a Saturday night because it's quiet. But I've started catching myself when I feel irritable. I was just in Seattle for five days. The first three days I was totally present, just being a tourist. Day four, I was already feeling the pull back to my emails. Day five, I was that guy — "Okay, vacation's over, I have payroll." So I've started catching that feeling earlier and reminding myself that this is life, and we need to enjoy it. When I work, I go all in. Which means when I rest, I should probably go all in on resting too. Which sounds counterintuitive, but I think it's right.
Dan Freehling (26:34):
Taking rest as seriously as work. Can I ask how you got into tech in the first place? What draws you to the startup life?
Jermaine Ee (26:44):
When I graduated from USC, it was the peak of the tech boom. I couldn't land a job — either I was underqualified for things I wanted or the recruiters thought I was overqualified and wouldn't stay long. They were probably right. So I just started building things, trying to make money. For a few years I drove Uber during peak hours — this was around 2012, when it was effectively guaranteed $45 an hour. Good money. I'd drive four or five hours a day and spend the rest of the time at Starbucks working on whatever I was building. What has changed is that now when I have a vision, I can execute it a lot faster. I know myself better. Things move faster when you have clarity about who you are.
Dan Freehling (28:22):
What was the most surprising thing you took away from driving Uber?
Jermaine Ee (28:29):
The people who seemed to have less treated me the best. I'm not sure that's actually surprising — I think we all kind of know that. I remember one passenger who's a pretty well-known public figure, and he was just dismissive and unpleasant. It was disappointing given the public persona. On the other end, I ended up becoming friends with multiple passengers because I talked with everyone. I turned off the app more than once just to go hang out with them.
(29:45) I also used to film these little selfie videos for my future self at 4 AM in the car — "It's 4 AM, I need to hit 20 rides today to hit my bonus, and then I'm going to go work on the thing I actually care about." I need to find those videos. They're out there somewhere.
Dan Freehling (30:07):
It feels like the right time to look back on them. How do you keep up with everything moving so fast in tech right now?
Jermaine Ee (30:21):
I've stopped trying to keep up with everything. You can get completely overwhelmed, and the truth is you don't need to know most of it. I follow at most four newsletters — pretty tech-heavy ones — and that's how I get my information. For specific questions, I call a smart friend. That's been more valuable than any feed.
Dan Freehling (30:52):
Same here. I was telling you earlier that it's rare to find a third-degree LinkedIn connection these days where we have no one in common. There's real value in conversations that pull you out of your immediate bubble.
Jermaine Ee (31:25):
Last night I went to a FinTech meetup — Heirlight is adjacent, not quite FinTech, but close enough. I go to every event with the same goal: one interesting conversation. If I walk away with one real connection, that's a win. Most days we have zero. I don't go in thinking about maximizing. When you try to maximize, you end up scanning name tags and qualifying people. I used to do that when I was younger — doing research before meetings, being diligent. Now I just try to go deeper with whoever I'm talking to.
Dan Freehling (32:21):
Any books or resources you find yourself recommending most often?
Jermaine Ee (32:28):
The book I've recommended most over the years is Essentialism by Greg McKeown. I actually met him once, about ten years ago — great guy, great storytelling. The book that most directly inspired Heirlight is Die with Zero by Bill Perkins. A lot of the concepts there affected how I think about living, spending, and the role of memory. And I really love Predictably Irrational by Dan Ariely — it's about how humans are reliably irrational in ways we can understand and plan for.
Dan Freehling (33:14):
What's the core reason you keep recommending Essentialism?
Jermaine Ee (33:18):
It ties directly into everything I've been saying about clarity. Having the clarity to know what is essential, what matters most, and doing more of that and less of everything else.
Dan Freehling (33:33):
And how is Die with Zero actually affecting how you're choosing to live right now?
Jermaine Ee (33:44):
One of the concepts I keep coming back to is the seasons of life. In my 20s, I didn't go backpacking through Europe or sleep in hostels. I wouldn't do that now in my 30s either — it would feel different, strange. There are things I'll do in my 30s that I probably won't do in my 40s or 50s. So the idea is: before you leave the season you're currently in, be intentional about what belongs to it. For me right now that means going to places that are genuinely hard to travel with kids. Last year I went to Delhi, Agra to see the Taj Mahal, Jaipur during Holi, then Kathmandu and the birthplace of Buddha in Nepal. Not places you'd do easily with a stroller.
Dan Freehling (35:29):
What a trip. So how can listeners find Heirlight and follow along with your journey?
Jermaine Ee (35:40):
I'm Jermaine Ee everywhere — pretty easily searchable with a unique name. Heirlight is at heirlight.com. Right now we're live in California, but depending on when you're listening, we may be in more states. If you're not in California yet, you can still download and try the app — just know the documents will be tailored to California law. It's free to download and free to use. You only pay when you export your document.
Dan Freehling (36:14):
Definitely encourage everyone to check out Heirlight and follow along with Jermaine. Jermaine, thank you so much for joining me. It's been a real pleasure.
Jermaine Ee (36:21):
Thanks for having me, Dan.
