How to Sell Something People Want to Avoid with Jermaine Ee

In this episode, I talk with Jermaine Ee, founder of Heirlight, about how to market products and services people actively avoid, using will creation and estate planning as the clearest example. 

We dig into trust, storytelling, and small first steps that help customers move from “I’ll do it later” to real action. We also cover:

• problem aware versus solution aware buyers and why education alone fails
• the real reasons people avoid wills beyond money, including beliefs and past experiences
• life-change moments that make people receptive, like moving, kids, job changes, and loss
• using stories to reduce fear and help people see the benefit on the other side
• trust as the main metric and how early drop-off signals a broken journey
• using AI tools to prioritize tasks, reduce clutter, and create momentum
• choosing the “entry price” tasks that come with building the life and business you want
• growth tradeoffs between B2B partnerships and direct-to-consumer marketing, including CAC to LTV math

Transcript

#164, How to Sell Something People Want to Avoid with Jermaine Ee

[00:00:00] 

As a business owner, you know the things that your client needs the most, but they're the ones that they keep putting off or changing the subject about or swearing that they'll deal with the issues next month or next quarter. Well, it turns out that selling something people are actively avoiding is its own kind of art, and my guest today talks about it on a regular basis.

Jermaine Ee built a business helping people face one of the most avoidable topics out there: creating a will. And what he's learned about getting people to say yes works whether you're selling gym memberships, nutrition, bookkeeping, or anything else that people would rather not think about doing. So grab your coffee as we talk about marketing and avoidance and all things business.

Here's my chat with Jermaine

Janice Hostager: Hey, Jermaine. Welcome to My Weekly Marketing

Jermaine @ HeirLight: Thanks for having me

Janice Hostager: So your business started from a conversation with your mom, right? About her retirement. What was the moment in that conversation where you thought, is a business, not just a family talk"?

Jermaine @ HeirLight: Well, the conversation happened about two months before that realization. So if I had to take us back a little bit, uh, it was over lunch at a place that we go to often, so it feels like a routine. But on this particular lunch, we talked about retirement, and I realized there's a indication in her voice that her fear of retirement isn't so much of anything to do with money, but rather the lack of certainty as to how much she has right now.

So this lack of clarity was the insight that got me building this AI tool for her. Essentially, this was 2024, so-- or 2025. So this was just a simple, uh, ChatGPT that asked her questions about, you know, what she had and the memories and the people she had in her life. And it wasn't until a few months later that I [00:02:00] realized if I had this information, I can actually organize that into a legal document, a will, and that's where the business idea started..

Janice Hostager: Okay. how do you market to somebody who knows that need to address something, but they don't wanna face it?

Jermaine @ HeirLight: Yeah. You know, I study a lot of what the life insurance companies does and a lot of the other estate planning, uh, companies they do. And the truth is, is like it's a lot of education. I think if you kind of break it down back into the marketing terms, there's people who are aware of their problem, and then people who are problem aware versus solution aware.

And I think there's certainly out of the 360 or so million Americans, you know, 70% of people don't have a will. And I'm gonna go ahead and guess that out of that 70%, probably about half of them could benefit from one, and maybe a chunk of them are aware that they need one, but they don't know what the solutions, solutions are because it feels expensive, it feels heavy, it feels like going to attorney cost a lot.

And so there's all this preconceived notion about what it means to have a legal document, a will, an estate plan. And our challenge really is to educate and simplify and really meet people where they're at when they think about these things.

Janice Hostager: Hmm. I mean, we actually, we moved to Texas about six years ago, and we did not update our will or any of our legal documents, and it's something that we just are putting off because it's so uncomfortable. I think it's called cognitive dissonance, right? Something we don't wanna deal with. , What's the difference between, like, not ready to do it, 'cause we can always find excuses, right?

Like, yeah, yeah, yeah, it's on the list. I've had it on my list for six years, right? But, what's the difference between, not ready and [00:04:00] being scared?

Jermaine @ HeirLight: Yeah. You know, this is a topic that is deeply human. You know, when we started this, I thought not having an estate plan was a socioeconomic thing. Rich people had wills, people who didn't have money didn't have wills. But what I come to realize, you know, in talking to our users, is that it isn't pure-- I think socioeconomics may be 10% of it, maybe 20.

The other factors are, what do you believe about death your entire life? What do you believe about attorneys your entire life? Or what have, what experiences around you shaped how you thought about this topic? And it's so complex, right? It's like if someone who's recently been to a funeral and had heard about a, a probate challenge, an estate infighting of families, they have a completely different, um, assumptions about this topic.

And the way we've been-- The way we've learned to introduce this topic into more people's life is try to meet them where they're at. And what we realize is that people who are going through life changes, so moving, having a new home, new kids, loss of someone near them, even new job, right? 'Cause when you sign up for a new job, you enroll into insurance, and it's the first time in a year that someone's asked you, "Who is your beneficiary?"

It's something we don't think about,

Janice Hostager: Mm-hmm.

Jermaine @ HeirLight: we try to meet them where they're at and try to lower the barrier of, uh, the l- the, the lingo. No legal jargons.

Janice Hostager: Mm. Yeah, that's interesting because I feel like in our case it's more it's 100% guarantee that my husband and I are going to die. I mean, we know that that's gonna happen. We know that, Texas is a different state. We moved from Minnesota where the laws are different and, and prior to that we were in Wisconsin where the laws are different.

So it's really a matter of updating it every time we make a move across state lines. but [00:06:00] I think it's really interesting because, I think we have to do some soul searching to really understand what's holding us back sometimes. So what messaging d- have you found that really makes people lean in and start listening?

Jermaine @ HeirLight: Yeah. I, I'm actually curious if, if you want to go there to try to diagnose, you know, what is it that is putting, , making you put this off, you and your husband. And, and you know, it, it's, it's actually as simple as it's just not top of mind, right? It's like I go through my day, things get really busy, and the feel- the thought of picking up the phone and calling an attorney, um, or even an app, right, just like just on my phone, just feels like, "Oh gosh, I got-- I, I'm gonna go do laundry first."

You know? I'm gonna go do something, really anything else first. Yeah.

Janice Hostager: It's that urgency plus it, you know, is it urgent? Is it important? It's important, yes, but it's not urgent because neither of us are sick or, you know, not that we're getting younger, but yeah, I think what you were saying is true. We put it off.

Jermaine @ HeirLight: I mean, in, in some ways you're confirming something that we believe, uh, when we think about marketing. We think that the way we're, we're doing this is to just tell stories. You know, part of my s- my strategy, my go-to-market, is to go on podcasts, is to, go on, places where people talk about stories of their lives.

I don't know if this podcast is out yet, but, you know, I did a interview recently with the National Museum of Funerals. It's, it's in Houston. It's kind of a-- I, I, I never, I've never heard of it. But the, the entire museum essentially documents and shares how people approach end of life and the stories of, you know, how our perspective of end of life shifts.

You know, there's one thing that's very interesting to me w- when I started this journey is [00:08:00] I, I am Asian American. I'm Chinese American. In my culture, we tend to live in multi-generation household, so it's very common for me to have my kids and my parents in the same house. But what I realized in the American society, which I am equally a part of,, born and raised in LA, people are dying alone.

People are spending more and more time into their old age being alone. And I realize when I surface these stories, it helps people question some of the assumptions that they have. Why do we want a picket fence house, when we're older? Why shouldn't we be closer to the people we love if that means giving up a, you know, a front yard and backyard, right?

So I think it's these stories about how humanity is shifting, and maybe we'll take it a, a step down from humanity. Let's keep it simple. How we as people, individuals, are learning more about what we love and what we don't love. I think these stories are what, uh, will get people out of their chair and do something.

Janice Hostager: Hmm. Yeah, I agree. I agree. So what, what role do you think trust plays in all of this when you're selling something difficult or just having an uncomfortable conversation?

Jermaine @ HeirLight: I think it's the only thing - a company like mine has. You know, we, we look at our data, , of, of the people that come into our app, 30% of them, if they make it through the first two questions, which is what is your name and what state do you live in, they tend to make it through all the way. And if they drop off at the first two questions, the 70% of them, uh, most of the time it's an indication of the lack of trust or the lack of desire.

It depends on, you know, how they come into the flow. But what we realize is that if at the point where we ask them for their name and their state, we haven't done enough to gain their trust, whether by design, [00:10:00] copy, or the journey that they've been on from a meta ad to our landing page or a podcast to our landing page, then we lose them.

And so trust really is the only thing that we're measuring

Janice Hostager: Interesting. So there are certain professions, a will obviously, things related to death, life insurance, these are all that category of things that we want to avoid. There's other things, of course, too. There are a lot of things that we avoid without even realizing it. Hard conversations with people, anything that involves a hard conversation. For some people, it's visiting a doctor. I see it in people who don't wanna deal with their marketing issues. Can you, out logic avoidance is really what I'm trying to get to. Is there something that actually moves someone from, "I'm not ready," to, "Okay, let's do this"?

Jermaine @ HeirLight: It's interesting where my brain went with this question. , I thought of this, you know how for the past 10 years we talked about social media, how it's, uh, it's pulling us to the left and to the right. It's making us all more extreme. I actually think of AI as the opposite of it. I know there's a lot of negativity around AI right now, but if you really think about what AI is doing, it's giving you-- It's a predictive tool, right?

It's like you tell it A, B, and it's predicting that you want to say A, B, C, D.

Janice Hostager: Hmm.

Jermaine @ HeirLight: So what that, what that does is instead of giving you the extremes of the edge cases, it's pulling us back to the center, and I think that is so helpful when we're trying to think and brainstorm and gain more clarity, right? So one of the things that I like to do is I have, uh, an AI project set up.

The instruction that I gave it is, "Every time I give you a list of tasks that I have today, help me prioritize based on the ones with the highest impact and based on the things that I feel [00:12:00] good doing." So then I can immediately take the-- take a look at this list and visually tell myself, "Okay, if I'm feeling a little lazy right now after lunch, I'm having food coma, maybe I want to tackle the task that is making me feel good," right?

So, so then I'll look at that list and I'll do that first because I know self-awareness that that's gonna help me kickstart this gear of wanting to do things. So I think similarly to marketing, you know, I, I have probably 20 posts that I should be making. I probably have a few articles I should finalize and start posting on LinkedIn.

And one thing I found really helpful is just to use a tool like, like a simple AI, whether it's Claude or Gemini or ChatGPT, to help us sort out the thoughts in our head, to simplify them so that it allows us to move forward without so much clutter.

Janice Hostager: Hmm. You said something really interesting there. It, it's like taking that first step. I think that's huge because, I notice just even myself and other people, for example, if I go to a conference or an event of some sort, whatever the topic was at that time, it brings momentum to it, right? So those baby steps like, "Oh, he was talking about this, and he's right.

You know, I should really do more of that." Or, maybe if I took one step in the right direction, easy step, something that you like, that would move people further along. I'm just thinking in terms of like marketing. Social media is, is a tough one for me. I hate getting in front of the camera.

I hate recording. I hate doing it. I really do. But, you know, being in marketing, I realize it has its value, right? So how do I get, for example, myself to say, "Okay, h-here's what I should do." What, what first step can somebody... I communicate to clients when they feel the same way to say, "Okay, this isn't [00:14:00] gonna be your favorite thing, but let's start here.

Just do this baby step"?

Jermaine @ HeirLight: Yeah. You know, I think about this all the time. You know, my, my girlfriend, she asked me, "Why do you choose to do something that you know it's so difficult and you have to motivate yourself to do it, and most of the days you don't see the results?" You know, you're, you're really s- you're posting something, it doesn't gain a lot of traction or it doesn't gain any traction, and you put all this hard work into it, and how do you motivate yourself to do the same?

Um, I think I have a very, very good situation, which is I'm building something that is true to my heart. You know, I'm building Aerolite. It's kind of ex- an extension of who I am as a person. I care about these topics. I love talking about these topics. But I also started a YouTube channel, and I am still in the, the process of being very cringe at myself, right?

I'm looking at these videos of me and I'm like, "What? Who cares?" You know, "Why,

Janice Hostager: Right

Jermaine @ HeirLight: even making these?" Um, but once in a while I have to remind myself that, you know, doing all these tasks is the entry price to wanting to live the life that I want, right? If I am so bold as to wanting to have my own company that affects millions of people, hopefully soon, that these tasks that I so dread to do, this cringiness of my videos, it's just the entry price to this ambition that I have, right?

And of course I can just stop all of this, give up, and go get a job. But then I'd probably be thinking about what if when I'm in this job. I'd probably be thinking about all the freedoms that I, that I lost while I'm working at a job that I don't enjoy. And I think it's kind of a-- back to the question of like, which kind of, uh, which kind of difficult tasks do you want to do?

What kind of difficult are you choosing?

Janice Hostager: Right. And the interesting thing is, and I say this to my kids all the time, it takes that [00:16:00] courage to get through something difficult, to do something you don't wanna do, but the rewards on, are on the other side of that. And I think that's what you're saying too, is like the rewards of having , a business that you love, that you are passionate about, that you know helps people, is worth the cringe factor of in front of a camera and doing the thing. I've heard this phrase, I don't know where I heard it, but, if you're joining a gym, right? 'Cause we all know we need to exercise. Most of us need to exercise more than we do. I heard the phrase the heaviest thing at the gym is the front door. And I just thought, yeah, that's right. If you can take that first step, do something toward your goal, the rest of it comes so much easier. If I'm gonna get changed, get to the gym, get in the gym, I'm probably not just gonna turn around and leave, right?

Jermaine @ HeirLight: Yeah, My entire mindset around how I look at my life and how I spend my time has shifted a lot. So something we didn't touch on yet in this, uh, short podcast that we have is, you know, I started HeirLight-- I started this idea of HeirLight about a year and a half ago, and four or five months into building this, my mom suddenly died.

She had a stroke,

Janice Hostager: I'm so sorry

Jermaine @ HeirLight: And I'm coming from a place now with HeirLight of gratitude because, because of HeirLight... At the time, it wasn't even called HeirLight. We didn't even have a name for it. Because of this project that I was doing to get to know my mom better, to get to know her life better, I was able to get all these conversations with her, her dreams, the things that she missed the most, the people that she wished she talked to more, and of course, where, where's her 401and all these things, um, as a part of the will.

But because I had this conversation, I was able to see my mom more clearly. I was able to have a relationship with her even deeper than what I had before.

Right when my [00:18:00] mom passed, I remember saying to her that, "Hey, maybe you should work less now because I think you have made the last dollar that you need to live. And every dollar that you make from this point forward, you're basically working for me because when you leave, you're just gonna leave it behind for my siblings and I.

And I really want you to enjoy the time that you have left," right? Not knowing that she was gonna get a stroke in a few months. And, and when she passed, I remember thinking to myself, "Gosh, she's gonna be dead for a very long time," but she didn't really squeeze the most out of the life that she had when she was still here.

And, and this is not coming out of regret because we did do a lot. This is just, like, such a reminder to me that, yes, I can get a job, yes, I can do anything else that I wanna do, but in this very moment, I feel most passionate about this business that I'm doing, right? That I'm building in some ways in honor of my mom to spread this message, to get people to think about having more clarity in their life and also make a will.

But at the end of it, this is the path that I've chosen, and so I will not complain about the cringe. Some days it's hard,

Janice Hostager: Hmm.

Jermaine @ HeirLight: I try to look at it with gratitude that, you know, I'm gonna just try to squeeze the most out of the life that I have right now.

Janice Hostager: Oh, I love that. Yeah, I know people that have a thankfulness journal that they do every morning. They just write down a few things that they're thankful for every day, and it... How that changes their perspective on things.

I think a lot of us as business owners, whether we sell coaching or consulting or some kind of service, people want to avoid purchasing something or pursuing something because they just see that immediate hurdle in front of [00:20:00] them. They see "Oh, I'd have to pick up a... I'd have to research and find an attorney who deals with wills in my area," or they'll have to, find somebody that does the thing, or get in front of the camera, or go to the gym or whatever it is. You have to focus on that light at the end. Like, here's just what it looks like on the other side.

And I think the people that... You mentioned stories. I think the really good storytellers are gonna be able to communicate that. Would you agree with that?

Jermaine @ HeirLight: Yeah. Um, I was talking to a pastor yesterday morning, uh, about Aerolite and, you know, he, he told me something that really caught my attention. He said, you know, in, in his church, he's a pastor who also works for a hospital, end of life care and things like that. And he said, you know, even people who want to go to heaven refuse to think about death.

And they know to go to heaven, the path is through death, right? You, you need to confront it, and yet they avoid it, right? Even with that amount of conviction in their faith. It's very interesting to me. It's, it stuck with me the, the past 24 hours since I talked to him. Um, but, you know, being, being a business owner, I think it's a very unique type of mindset and a very unique lifestyle.

This is my sixth business, seventh, depends on how you count the projects. And, uh, I, I completely understand this, you know, there's this tension between resources and time and headspace and context switching, right, to do all these tasks in, in marketing. Um, but yeah, if, if anybody ever wants to try, you know, just have to-- have a, have a ChatGPT help prioritize some tasks.

Um, one thing that I find really interesting, I'm not sure if this has come up in the podcast a lot, is I don't think we talk enough about the input that we give our AI, right? We, we often think about AI as like what outputs are we getting? But it's equally important if you [00:22:00] want your AI to be very specific to your needs, to ask it, "What information can I give you to help me be more efficient in planning my to-do list?"

For example, right? So... And I can simulate that really quickly. So if you go to, your ChatGPT or Claude or Gemini and you say, "I would like you to be very good at helping me prioritize tasks. I want to give you my to-do list and for you to tell me which are the things that I should be doing at any given time of the day.

Ask me some questions to help you help me so that we can clarify, you know, your job as my assistant." And then the AI will then spit some question out to you, and it's probably gonna ask you a few things such as, um, are you someone who plans by task or are you someone who plans by goals, outcomes, right?

That's a very-- two very different kind of way of doing things. It w- it may also ask you a question, for example, when you lose momentum, is it because of a lack of, , interest or roadblock friction? You know, like it's trying to understand you as a person so that it can help you plan out what you have to do.

So I think there's, there's a lot of tools now that helps us do that, and I'm, I'm very grateful for the technology that's out there. Uh, and I definitely use that to help me move through all the tasks that I have to do

Janice Hostager: Yeah. I actually just did that the other day. Being an ADHDer, you get to a point where you're just, like, paralyzed because you have so much, you don't know what's more important, or you can't, at that moment, figure out what's more important. You're trying to reach a goal by a certain date, things keep popping in your head, and you don't know what to focus on, right?

You don't know how to prioritize, or I don't. This is my [00:24:00] problem, and same thing. I went to Claude, and it's very helpful. It will ask you questions even if you don't ask it to ask you questions, which is nice. But yeah, I think that it's really helpful, and I think that that can help you get past the difficult things that you have to do in your business, and also kinda help you think of ways if you have clients or people that you work with that with the service that you provide, right?

So once you really understand your ideal customer, AI can be really helpful in, some, ways to communicate, ways to connect with them, I would say, so that you can get to that point which they are ready to hear it and ready to act on whatever it is you're selling.

Jermaine @ HeirLight: Yeah, I, I find it super cool if I ask my AI, "Based on everything you know about my business, give me a report." Right? So, so then it gives me a report of everything it knows. And oftentimes there's some mistakes because the memory isn't perfect. And I w- I love doing that because it helps me, one, zoom out a little bit and see the big picture, but also sometimes it also helps me pr- think clearly to prioritize what is actually needed.

Uh, I think it's such a, it's such a blessing to have that.

Janice Hostager: Yeah. It's definitely changed my business. So, Tell me more about how people can connect with you. Tell me more about your business

Jermaine @ HeirLight: Yeah. So we are now live in 12 states out of the 50. You know, we are doing estate planning, right? So probate codes in all states are different, and it, it's very expensive to work with attorneys because we gotta make sure our, our output's legally valid and, and very good, for all our users. You can-- I, I have a one of one name in this world, so my name is Jermaine Ee.

I'm pretty easily Googled or, or ChatGPT or, or AI asked. Um, but Aerolite is, you know, live on the App Store and, and I'm always looking for partners. If you, you know, if you are listening to [00:26:00] this and you have a wealth management practice or a adult daycare, you know, like these are folks that I would love to get in touch with.

You know, I, I'm actually in this juncture right now. You know, talk about marketing. I am-- I know I can grow through B2B as a business. I know I can partner with credit unions, I can partner with HR service providers, insurance. Um, there's, there's a few more. Adult daycares, hospice cares, and things like that, funeral homes.

That's the B2B route. But I am so maybe romantic about this idea that I can figure out my CAC to LTV and play that game and not have to do B2B sales. And, and that's the juncture I'm in, I'm at right now. We've almost figured out our meta ads. You know, we're, we're getting a new customer at about $200 per sign-up, but our subscription fee's only 149, and there's a, a few things there that I'm working through.

Janice Hostager: Yeah

Jermaine @ HeirLight: it's, it's very fun. I'm, I'm finding a lot of joy in the process of optimizing things. Um, yeah. I hope this, this message kind of resonates with business owners out there. You know, this is such a core tension of like what path to go in marketing.

Janice Hostager: Right, one to many versus one to one. But , I see your point. You wanna be able to stay connected with the end user, right?

Jermaine @ HeirLight: I think it's n-not even that. I think it's even the fact that I know if I partner with a financial services firm, what they want out of me is the relationship I have with my user. And for me, the relationship and trust that I have with my user is the ultimate prize, right? It's, it's the prize that if I have that, if I own that fully and not sell it to a financial services company, um, and that's not necessarily a bad thing, but, but I get to decide then what direction I take my product after, right?

If I wanted to [00:28:00] build, a phone scam detection company, right? If... You know, I have this crazy idea that I wanna be able to catch every time a scam call comes through. I wanna track them. I wanna log them down through my users. Because one of the texts that I get in my family group chat often was my mom would always say, "Hey kids, is this real?"

And for us it looks like a scam, but you know, my mom, she's not as tech-savvy and she would ask us. I wanna do that for everybody. I wanna do that for every family out there. So if I own the relationship and the trust with my users, I get to go play in these directions that I want to. Whereas if I, if I had to deliver a service to a hospice care, I'm a little bit more restricted.

Janice Hostager: Yeah, that makes sense. whatever way you decide, I think you're gonna have, a bright future. So, thanks so much for being here today, and I will put all the links that we talked about in the show notes for today. So thank you

Jermaine @ HeirLight: Thanks for having me.

Speaker 3: I hope you have a better idea about what motivates people to take action after our conversation today. For more information about anything we talked about, visit myweeklymarketing.com/164 Thanks so much for listening.

I'll see you next time. Bye for now.