Jermaine Ee - Building A Legacy Through Estate Planning

Want the courage to leap into entrepreneurship and a practical way to protect your family’s future? We sit down with Jermaine—an entrepreneur shaped by immigrant grit and cross‑cultural identity—who’s building HeirLight, a modern estate planning app that uses AI to make wills and trusts accessible, private, and easy to start. The conversation moves beyond hustle culture to the deeper question: who are you as a builder, and what pressures do you actually want?

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http://www.heirlight.com/en/podcast

Transcript

SPEAKER_00 0:17

Hi, my name is Nick Ford, and I'm the host of the Transparent Podcast, where we believe in bringing transparency to the world of small business. And this week I'm joined by a guest, Jermaine. I will let you introduce yourself.

SPEAKER_01 0:30

Thanks, Nick. Hey, I'm Jermaine. I was born in Los Angeles. And as I've grown older, I've been discovering what it means to be American, Chinese, Malaysian. That's who I am. Growing up between cultures shaped how I think about identity, responsibility, and legacy. I came from a family of entrepreneurs, both sides of my families. Each generation took a risk to build something that lasted beyond themselves, beyond their lifetime. And even though they would never admit that, we're all business people. Today I am building Airlight, a modern will-making company and app that grew out of a personal loss and a realization that most people avoid the conversations that matter the most until it's too late. And that's me in a nutshell.

Why Share Entrepreneur Journeys

SPEAKER_00 1:18

That's great. Yeah. Well, thank you for being on the podcast. And, you know, part of the idea behind the podcast was to hear from people like you. You know, you've had a family of entrepreneurs. Um, but the the idea was that if we could get people on the podcast to share kind of how they got into entrepreneurship, what their journey was, the highs and the lows, um, hopefully that would inspire people who are, you know, I call it entrepreneurs, maybe sitting on the fence on an idea but haven't taken the leap yet. Hopefully encourage them and um, you know, inspire them. That was something important for me. My grandfather was an entrepreneur. And I'm sure for you, seeing your family do it, it makes it more real to you. And you're like, oh yeah, I can do that. I know how that works. So that was kind of the idea but behind the podcast. And um, you know, I started transparent staffing four years ago now, come up on five years, which is crazy. That uh um had a similar purpose to bring transparency to to staffing. But uh, you know, when I think about entrepreneurship, I think another, you know, a TV show that really got people their eyes open to entrepreneurship was Shark Tank. And, you know, there's these entrepreneurs that go on there and they pitch their their businesses and sometimes they have a job still, or sometimes they're in the business full time. Um, but what are your kind of thoughts on you know the side hustle culture where you can have like these multiple streams of income or you know, business that is a side hustle versus you know, no, you you really need to go all in? Like the sharks would tell you, no, you gotta go all in. You can't you can't have a job still, go all into your business.

Side Hustle Vs Going All In

SPEAKER_01 2:54

Yeah, I mean, going all in makes for better TV, right? So they will always encourage people to go all go all in. I think for me personally, it's it wasn't really a choice. I was just never good at doing a job. And I was never good on application, even though I went to a very good university and I did the whole thing, you know, I studied, I interviewed, I interned, but I was never a very good employee. And so I think my path was written for me. But I think what I tell others is that being an entrepreneur is is really fun to think about, but you got to be self-aware, right? You gotta know are you the kind of entrepreneur that wants to build a venture backed company, for example? So you raise a lot of money and the pressure's on you to grow really quickly, or are you someone who wants to build a service business where managing the cash flow is the key? Or in your line of work, an agency business where you know scaling up hit count, managing your clients, a client services business takes a unique personality. And I think knowing yourself is probably the first place that I would start it. And uh yeah, for me, it's always about going all in. I like to just put all my chips in in one place. But as I get a little bit older, I realize that it's difficult to stay focused, actually. Because especially now with AI, there's ideas that come to us all the time, and you you read about things all the time and you feel like you can do more. And so as I get older, I think the more difficult thing is to say no to things, is to say no to side projects.

SPEAKER_00 4:33

Yeah. That was that's conversations that me and my wife have had regularly where I'll have these other ideas about, you know, I've really had it on my mind to start a coffee shop and wanted to do this like co-working slash coffee shop concept. And uh my wife's like, no, you need to focus on your business, you don't need another side project. Um, because I've done I have done that before. And you're right, it's it's very hard to stay focused. And um, you know, one of the pieces of advice my grandfather gave me when I had I took one of those side hustle ideas to him, and he was like, Well, if you want to make more money and you're so good at what you're doing now, why don't you just spend more time on your business? Wouldn't you make more money if you just focused more on your business rather than getting distracted by another thing? That's those good advice, you know, to stay focused and you know, um, like you said, put all your eggs in one basket, so to say. But I think also like the reason on Shark Tank, they want them to be all in the business because they want them focused on it, but they're also taking on capital. So I think anytime you're taking on capital, the way that you look at that's gonna be totally different, um, especially the investor, the bank, or whoever's giving you money. Um, so well, tell us a little bit about how you got into entrepreneurship and you know your your family background with that.

Self‑Awareness In Business Models

SPEAKER_01 5:52

Yeah, so I think for me, actually, I'll back up a little bit. So I I kind of grew up watching my parents starting businesses and many times failing at it. And I think the most interesting thing to me is that they always got back up and they kept trying. And you know, I I always wonder how does it feel like to not have a foundation, a base, uh, something, a safe space to go back to. And, you know, I I got really lucky because both my parents moved to Oklahoma in the 80s, and you know, they did barely spoke English and they moved to Oklahoma. And I always think to myself, like, in my 30s, would I have done that? Would I would I have packed up my bags and and went somewhere just to take a chance and um bet on yourself and without a safety net, really, because what I realized after is they they could barely afford university, so they had to work uh illegally and you know, undocumented, or they were students, so they were not supposed to work, but you know, of course, people do that, they do what it takes to get by, and so so they're working multiple jobs and oftentimes getting bullied in some ways because it was all uh the way it is, and so yeah, so it's it's super inspiring and it gives me a lot of courage to understand that my baseline is not that bad. I can always fall back to uh you know, happily go back to driving an Uber. I drove an Uber during my first startup, and granted, this were like good years of Uber. This is like 2011, where they guaranteed your hourly wage. So I would drive an Uber from 5 a.m. to 10, go work in a startup, and then go back to drive during peak traffic. So I would only drive search hours, and in LA at the time, that was great money.

SPEAKER_00 7:41

Oh yeah. Yeah, yeah, I've heard that's changed a good bit.

SPEAKER_01 7:45

Yeah, and so to me, you know, my baseline has always been if I had to, I'll go back to do whatever it takes, you know. So so having that baseline made it easy for me to take chances. But to go to go back to your questions, I've always just followed my curiosity. Um, admittedly, when I was a little bit younger in my 20s, I followed the money, you know, whatever was trending. Uh, I started an AR company to try to sell Snapchat AR filters that was trendy, you know. So I think now what I want to really focus on is to not take investor money so I can focus on what I want to build. And it's also a place of privilege, right? To be able to burn my own savings to do that. But more importantly, is just to be able to choose the path of uh the kind of people I want to work with and spend my time with. I think that's what I realized that's uh probably the most important to me. It's what I who I want to talk to every day. And I love my team. So that's great.

Focus, Distraction, And Saying No

SPEAKER_00 8:43

That's awesome. Yeah. You know, when you that brings up a uh, you know, another question that I had for you. There's something to think about with you know, taking on investor money. That's a good thing for people to think about without or thinking about getting into entrepreneurship. That just changed the way that you can approach the business, and you now have someone that is going to have control over what you're doing, or at least have a say in it. And so um, you know, thinking about who you take money from and and how you go about financing your business, especially if it's a capital intensive, you know, type company. Um, another thing, you know, with your with your family and with your businesses, have you have have have you typically had your own company started from the ground up, or have you, you know, been in the situation where you're doing like a franchise or buying a business?

SPEAKER_01 9:29

Yeah, so I've raised money before. I've raised uh during COVID, I was running actually, this is all in one. So during COVID, I was running an education business. We had a similar franchise model as Kumon and Magnesium and all these companies. So, but we were trying to be uh the the HQ, the company that was providing the franchise. And so it was a brain training company based out of New York City. And our goal was to I raised money on the promise that I would scale it to 10 locations, I would standardize our SOP, figure out the economics of it, and then we would start scaling up by opening franchises. I think franchising is a very interesting way to become an entrepreneur because if you know yourself, if you are good at following rules, franchising is great. But if you want to break out of the let's say traditional marketing, when you think of oh instead of selling it this way, I want to sell a different way. Well, if you have a franchise, you're a little bit bounded by the rules of you know the game. And if you break those rules, the penalties are are pretty hefty and it will actually take you out. And so so at the risk of sounding like a uh record, uh, I'm gonna repeat myself and say, you know, you have to know who you are, you really gotta know who you are because even taking on investors, uh, I've at this point turned down investors who are friends because I told them, like, hey, I I want you to be on my cap table. I want you to get this win with me. But if I take your money today and my product isn't making money yet, I'm gonna feel obligated to take your phone call. And as a friend, I don't want to feel that way. You know, and even for my even for my parents, yeah, I told them I'd love to take more, but or or take any money, but it's gonna change a little bit of the dynamics because I would start maybe avoiding certain conversations in stressful times. Um and so I think you gotta really understand the different types of investors that can come into your life. And I think there's uh a lot of information out there, and you know, sometimes when I talk to aspiring entrepreneurs, they don't seem to really understand when is the time to take angel investors or venture capital or private equity. Um, because the ideas all sound really cool. Like I want to raise a series A, but what does that really mean? And so I I would say like 99, maybe not 99, 90% of businesses in the United States don't require venture capital money. It requires probably a loan from the bank, uh, in fancy terms is raising debt because that makes more sense.

SPEAKER_00 12:18

Yeah, exactly.

SPEAKER_01 12:19

Yeah, um, but yeah, I I think at the end of the day, different money brings different pressure.

unknown 12:25

Yeah.

SPEAKER_01 12:25

The the debt that you yeah, the debt that you take from a bank doesn't change the relationship, it just adds interest rates.

Immigrant Roots And Resilience

SPEAKER_00 12:33

Yeah, right. You still pay it back and pay it back to interest. Yeah. Um, they don't really have it's not the same as taking on venture capital or an angel investor or something like that. Yeah. You know, I the franchising model is interesting. Um, there's pros and cons to it. Like you said, you're bound by the rules of their game. Um, the pro is you you kind of get their playbook and you get access to their marketing arm and that kind of stuff, but then you gotta go buy their playbook. You gotta play by their their rules. And you know, like you said, if you take you take things outside of that, then you're gonna start they could kill you. Um and that's what I found when I was I really wanted to do a coffee shop, and there was uh this Hawaiian coffee shop franchise that I really wanted to bring into Atlanta, but then as I got deeper into the conversations and started reading what the guidelines were and started you know, got to the point where I signed an NDA and stuff, and so I got access to like a lot of what you I was really gonna be committing to by going with them. I was like, okay, wait, now this is starting to feel like I'm gonna be working for someone again rather than having my own business like I I do with transparent staffing where I can run it however I want to. Um, so that's you know, you just get like you said, you gotta know who you are and how you how your mind works and how you want to run the business.

SPEAKER_01 13:49

So yeah, I think franchise franchise businesses are really good for people who are process driven. You know, they they have a process, they're really good at executing the process. I think that's incredible. And I think it would be really helpful if you're slightly passionate about the line of work too. You know, for example, if you if you started running hotels and hotels are really like real estate place, but you know, if you start taking uh a a Hilton franchise, uh a licensing deal, I mean these are fairly difficult things to run. And so yeah, you would really just be buying yourself a really expensive job.

SPEAKER_00 14:27

And a high risk job, too. Yeah, pretty high risk job. Yeah, yeah. Um, yeah, I yeah, I don't definitely agree with that. Um, well, so you know, you've you've talked about you know the different businesses you've been a part of. Uh with the day and age we're in now, with like AI changing a lot of the ways things are done. What's what do you see as the biggest scaling challenges you're gonna have or that you've kind of seen, and how have you worked through those?

SPEAKER_01 14:55

So for my app, apps are apps have always been difficult. To get someone to download an app onto your phone requires you know a lot of education, a lot of awareness. And then you layer it on that my app is about estate planning, it requires trust, it requires uh data protection, and we have to communicate all of that in a fairly fickle attention economy. So for us, it I will focus more on thought leadership, you know, we'll focus on getting content out there, inspire people to take action. The truth is like for me, it's a little bit different because 70% of Americans don't have a will. Out of those 70%, probably half of them really need one, you know, and out of those half, a lot of people need a trust. But the challenge is that a lot of people cannot afford to go to a lawyer. And and that's the kind of economy we live in where a lot of people put this off and it it comes back to hurt them in the future. And so the rich keeps getting richer and the poor stays poorer, right? So I I just saw that you know, with AI, this is one of those applications that uh can really help people. Just the fact is the law is black and white, AI can understand it black and white, and so you know, this is what I I'm trying to build, and you know, we're we're trying to make a meaningful impact in people's life down generations. And coming from an immigrant family, no one has ever taught me how to do estate planning, and and so I think this is really important. And so, my marketing, the challenges of scaling, it's a very human one. How do you get people to do something that is not top of mind and not urgent? Yeah, I think this is beyond AI.

SPEAKER_00 16:45

Yeah, it's hard. I mean, getting people to realize what uh they're gonna go through if they don't have it set up, you know. Um I we had family, um well, they were a friend of ours that were like family to us, but he owned a state farm like life insurance company, and so he sold life insurance for a living. And he was probably when he passed away unexpectedly, he was probably in his mid-50s, and um his wife realized after he had passed that he didn't have a will. So she ended up having to go to like probate and had to go to all these financial institutions, and he owned a business, and so um all the stuff that he you have to do, like you think that it's all you know, when it's simple, it's gonna be easy. It's not like there's so much work that has to be done if you don't have a will. Um, and if you have, you know, depending on I'm sure you have recommendations on what level of wealth you need to have to, you know, now you really need to have a trust set up. Um, but uh I laugh because I I think about have you ever watched the show Parks and Recreation? Enough. Yeah. Well, there's a part where the one of the main characters he doesn't have a will. I guess he has one, but it's like a sh a scrap piece of paper that says, you know, what he wants. And uh the lawyer was like talking to him and he's like, You really need to have a will. And uh he the character was pretty anti-government. And uh the lawyer was like, Well, you realize that if you don't have a will, then the then the government gets to decide what happens to your wealth. And he was like, All right, what do we need to do?

SPEAKER_01 18:19

Yeah, I I should, you know, I should really look it up because that's gonna help my marketing to have a pop culture reference. And oh yeah, uh Parks and Rec is based in Pawnee, right? Pawnee, India, and that's Pasadena. That's where I'm that's where I live. So it's literally the town that I live in.

SPEAKER_00 18:37

So yeah, that's funny. Yeah, it's a I'll have to try to find the clip later, but it's yeah, it's funny.

Franchising Pros And Cons

SPEAKER_01 18:43

Um but but back to you know, like this this person with a state farm business, like it's not a resource problem, right? It's like he he probably knew he needed to have a trust, and yet it's and it's not done. And so it always blows my mind. So uh the question is like what kind of conversation do we need to have to get people to take action? And one of my theories is that some people do not want to have a conversation with another human because of ego. And so maybe just maybe a AI agent is better at doing this job because there's no judgment, and they can ask them any dumb questions they want in any language in any way they want. So yeah, yeah.

SPEAKER_00 19:32

We uh my parents they have a will, but their will is was written in Texas, and so they and my aunt was a lawyer and did their will for them, and she's been begging them for like 20 years to get it updated and get her name off of it. Wow, um, and so we have a there's a there's a friend of ours through our church that's a lawyer and he's retired now, but he still has his license and stuff, and he's offered to do it for them for free. And but it's exactly what you just said, they don't want to have a conversation with a person, they they don't want to talk about their finances with somebody, they don't want to like go behind that curtain. And I don't know if it's also like people don't want to deal with death, like they don't want to think about that. Um, and maybe family members, you know, like me talking to my parents, like that can be a tough conversation. Like, hey, what are we gonna do when you pass? Like, you need to be ready for that. Um there is an awkward, there's an awkwardness to it that maybe having a technology solution that people can just go in and you know answer questions and have AI kind of solve that for them. That could be that could be interesting.

SPEAKER_01 20:38

Yeah, yeah. I think my my goal now is to just give it away to as many people as possible. And I'm really focusing on families that don't speak English as their first language because I know for certain that most of these families don't have anything set up. Yeah. Yeah. And so yeah, it's pretty exciting. But you know, talk about scaling, talk about AI. Like I I was thinking for two years basically, you know, what can AI do now that it that we couldn't have done before? And this is one of those things. So I think it's really changed the game with uh how we could live and how we could be doing estate planning. But we're still super early, and I think with all these news about AI disrupting and taking jobs away, you know, I'm trying to just find the the light here. So that's what I'm building.

SPEAKER_00 21:30

Yeah, that's a fitting name, then air light, right? Yeah. Very cool. Uh yeah, I think that's a great idea. I think, you know, yeah, AI is definitely changing things, and there's gonna be so much that is done with it that, like you said, you know, finding those things that couldn't be done before that can now. Um, you know, hopefully uh I know that there's gonna be jobs, obviously, that get eliminated, continue to be eliminated, but I think it's really gonna be a matter of the the people who you learn how to use the technology, it's gonna it's gonna just supplement them. And it's like when the internet became so big, like people who learn how to use computers and learn how to use the internet, um, they just became more efficient. And hopefully that's you know, it's another tool that's you know gonna be an important one, but that will just you. know supplement the work that we're already doing and make it you know more streamlined and people will be able to do more you know yeah how are you seeing AI affecting your industry yeah it's interesting um you know with I think the biggest way that it's it's affecting is just being able to eliminate a lot of redundant tasks you know um being able to screen candidates better being being able to find the right candidates and screen candidates is the biggest way I've seen um I haven't you know there's these AI agents that you can implement where you know I'm sure you've seen some of this but you know it'll do all my outreach for me it'll go like find prospective clients like I could go in and say like I want to fill a therapist position and it'll go like scrape LinkedIn and indeed for every therapist job scrape the you know data banks like Zoom info and stuff and find the contact information for people and send out emails like all automatically like I just click a button and do all that you know to me that's not super transparent when it's doing it all all that for me. I know my competitors are using it so I haven't done that too much where that level of AI for the like business development side because that's where I get hit a lot with you know companies wanting to offer that solution for me. So I haven't gotten into it that much maybe I should but uh on the recruiting side I have started to use it more just with trying to find candidates and trying to eliminate some of that redundant data entry and other things like that.

Funding Choices And Their Tradeoffs

SPEAKER_01 23:48

So yeah yeah I met this guy he dropped out of Harvard I met him in 2022 summer uh in New York and he was building a essentially a super smart recruiting tool and and he's been very successful uh I I remember using the first version of it and you know putting on my executive search hat I was like this is really good it saves me a lot of time but then there's like the art and the science like he's really good at the science like he's good at figure out data and and demographics and job history and things like that. But the art of like understanding why is someone going to leave their job or get a new job or be available affordable you know that's the art of it and I think the art is where recruiter still comes in.

SPEAKER_00 24:41

Yeah but there's definitely but a lot of the science is is being done really really well now so yeah yeah there's still I I don't think it's gonna replace recruiting and like recruiters there's a people element to that too um and just being able to understand personality and and things like that. But uh definitely you know it's gonna be continued to be implemented and uh utilized and advanced you know so the science behind it though is definitely there and being used. So I think that'll continue to grow.

SPEAKER_01 25:14

But yeah I'm just curious when we have enough data to train on the personality stuff. Like if let's have our entire company take a personality test and figure out what kind of personality matches this. What is our culture indexed? I think when we get to that point, which we will uh it's gonna be super interesting to see how recruiting goes.

SPEAKER_00 25:38

Yeah I've I've done that we went when I was uh at another company they brought in one of those it was like a personality assessment guru type person and we all did I can't remember which one we did it was something similar to like the Enneagram but on a it was not the Enneagram but as a work related one and so we all took the test like it was like an all day seminar. We all took the test all got our personality indexes and then talked about like how we would interact with each other in the workplace based on our personality types and uh on our teams and things and that was super valuable and to use AI to start doing that kind of thing there's just so much more intensive data you could get from that um I'm a big fan of the personality stuff. I I use it in my business and encourage clients to to use it and it's not so much of a like um yes no thing on like the hiring side like oh you're this personality like you're not a good fit. It just is a really good way I think is you best utilized in the interview process to talk to the you know candidates through like how they're going to interact in the workplace and how they'll interact with their team and things like that.

SPEAKER_01 26:46

So yeah. Yeah and I think what was missing with the personality test for me is they're not really purpose built. They're kind of generalist in some ways. And so I think once we start having data I think there's one there's a company out there that was doing a personality test for startup like how to find the kind of work that you like. And so I think it's called Pigment. So yeah they they're pretty it's pretty interesting because that's the only one that I've seen that's like built for people finding jobs or finding like the kind of career that they want to go into. But once we have big enough data set of what works uh yeah I'm I'm really excited to see yeah the way I the way I searched for my co-founders for my company on the top of my list was high agency I needed them to be resourceful like I needed them to you know when I tell them hey we we want to do this thing solve this problem instead of coming back to me with uh five reasons why we cannot and can I want them to be like here's what we can do and here's the trade-offs you know like if we do this here's the trade-off and and here's the tech stack that we have right now here's the cost I want them to just like be able to think like very resourceful and that was not easy to find I think I went through about 400 people and then I narrowed it down to maybe like 30 and and landed with two and so yeah it was a it was like a whole two months of doing this like interviewing people.

SPEAKER_00 28:24

That's an intense interview process yeah but it's so important and you know I think that you approached it the right way yeah even for me you know I don't have a I don't have partners but you know when I hire somebody um you have to find the right person that's willing to go figure things out on their own. Like you can't have someone that's for me like I don't have time to be like answering every question you have or walking you walking you through every process like being able to go and do things on your own and um just figure things out was super important and self-starter mentality you know um so that was what was important for me.

SPEAKER_01 29:02

But the question then is like where do you find people like that? What are what are some indicators? And in some ways it's like how do you raise kids like that? Because because if you're really thinking about you know where do you find people like that? It used to be like Boy Scouts, right? You can say like if someone who's done scouts uh or they've like sold cookies or have had a lemonade stand for example. So I I just wonder what are the modern equivalents of those.

Scaling An Estate Planning App

SPEAKER_00 29:29

Yeah well that's something that we're really working on with our with our two older our boys we we have two boys that are eight and six two year old girl but our uh our eight and six year old are doing something similar to scouts it's called trail life and it's more of a um like a Christian based Boy Scouts and so they do a lot of the same things as as scouts do and stuff but uh my older son is very entrepreneurial and he's you know since he was like six he's wanted to start his own business and um so this last year he did we did this uh entrepreneurial market and um he set up his own booth he created his own product he sold and collected the money um I helped him set some stuff up but it was all his idea and he did most of all of the work and uh the day that he had the actual market I wasn't allowed to help him at all like there the market was set up where like no they have to run the business like you can't help them take money you can't help them talk to customers so um I think for me too like I think what encouraged that in him is actually explaining things to him and walking him through how things worked um like my like my business explaining him what I did as a business and how it worked and what I did for companies and things like that. He was and maybe that is partly his personality he wanted to know that kind of stuff because my six year old's not as much like that. He's much more uh creative thinking and you know uh a rough play you know play type of boy whereas my older son's very analytical and wants to understand things so uh but I think just exposing them to things and and talking explaining things to them and giving them those opportunities um has been helpful for us with with young with young kids from early age you know so yeah I think what I really like about that is is that he you know a lot of times when I talk to at least younger people now they they don't know what it feels like to fully stand up for an opinion that they care about so like to sell something um I'm I'm getting this feeling the first time in a long time now where I'm putting a product out there to be judged and I think like being an entrepreneur that's what you do right you you put yourself out there and say here's my work and let the market judge you and I think I think maybe some indicators is like can they stand up for something that they believe in and defend it and have ownership to it. So yeah I I'm I'm finally after years of just like consulting and and wandering around and now having a business again uh yeah getting feedback sometimes can be pretty rough so especially in my space where you know we're we're estate planning app so we talk to lawyers and and my lawyer friends are calling me up and say hey yeah that's that's this is not good enough you know like AI can't take over this thing and I'm like yeah I know but but you're charging a thousand dollars an hour and there's a lot of people out there who can't afford that so yeah yeah yeah well I'm sure everyone is feeling that like law your law I imagine like you said is pretty black and white so how much stuff can AI start doing for for that legal space um but yeah I mean having accessibility to it for people that like you said especially that can't afford it but I think a lot of it is also just like people just haven't done it like they just haven't taken the time to sit down and do it. And you know it's it's super important especially as you look at your the next generation after you like my kids and um yeah but you know one uh one thing I really like to do I love studying successful people and I I listen to a lot of like motivational type podcasts with people you know like Tony Robbins type people or um art Williams is another one that I've listened to he has this uh just do it speech it's actually I have it on my podcast too but um you know I love studying successful people and you've had the benefit of seeing success and failure from your your family and how to handle that but what do you think separates people that are ultimately have success in business versus those who don't I think it's two things.

SPEAKER_01 33:49

So I'm gonna go with luck first I know it's not a popular answer but it is a truth. I think a lot of success is timing a lot of success is you know being born into the right place at the right time but that's not a really good answer because we can't really control a lot of that so the second one is I think what you're setting up your son to have which is grit and this concept of grit is you know how do you train it and that's that's what we're all looking for, right? We want to look for partners and and employees and investors with grit so that when the things get tough they don't just fold. And so I think seeing for me it's just having examples of people with grit all around me and then having people with humility. So I'm gonna sound super name droppy.

Death, Denial, And Trust Barriers

SPEAKER_00 34:41

I know we we chat about uh Shark Tank a little bit i i've met Mark Cuban and he's probably the most humble and interesting and curious person that that I've met probably very briefly I spent maybe like 30 minutes with him and and he I think the time that we had together we dug into questions uh about you know raising kids and I don't have kids but you know one of the things he told me about is that you know he was trying to raise kids who are responsible for themselves and and I think a lot about that you know just having grit uh and anyone who's successful their biggest nightmare is that their kids are too entitled right and and the the way to uh instill that and so yeah I I guess a long-winded answer to your question is is luck and grit yeah um but how do you get those things there is no yeah yeah there's no formula yeah I think there's definitely an aspect of luck to some to some people but then you also see people who didn't have luck or created their own luck that were successful or some people who were handed everything and wasted it. So I think that you know for me I'm very lucky I had uh the benefit of you know a two parent household that were had a strong relationship and raised me to um be responsible and to you know my my dad used to tell me my brother um when we were growing up he's like my goal in life with the two of you is to get you out of my house at 18 and able to be on your own um and he helped us through college some you know with with tuition and and stuff like that. But after that me and our brother both were out on our own and that's that's something that's very hard now there's so many kids that are going back to living at home after they you know get done even with college just because of the economy and other things. But um for me the grit thing what helped me a lot with the grit was athletics. You know I I played my jerseys up on the wall over here I played baseball through college. One of the things that's interesting for me to think about if you think about you know a major league baseball hitter they fail seven out of ten times. If you're hitting 300 you're doing really well that's a great batting average for the for the mate for the major leagues and they're they're failing seven out of ten times so I think athletics did a really good job of teaching me how to deal with failure and you know you're gonna fail every day. There's gonna you know not every message I send out to a potential client or every candidate I talk to is not going to always go my way. But if I let that just beat me down and you know okay I failed today because I got one rejection or whatever you know that would be crippling. You know you can never be successful that way. So I think sports help me a lot. There's other things that that can achieve the same same purpose but for me one of the things that I I've seen that separate successful people is they have goals. You know they have they have things that they're working toward that they're consistently focused on um you know if you don't have goals you're like a ship without a plan you know you're how can you reach a destination that you haven't set for yourself. So I think goals um is is really a big a big one for me that I try to to keep focused on you know I have a an index card I keep on my desk with a with an annual goal each year and so I'm looking at that every day. So you know I think goals and then you persistence with another word for grit but just being able to be persistent and continue to to work toward that and you've like the most successful founders you know like the Steve Jobs of the world they had an envisioned future that other people didn't see and they folks stay focused on it and could guide other people to it.

SPEAKER_01 38:38

So yeah yeah I think what you say there it's it's definitely something that I've been trying to do more myself which is just having clarity of my goals. Because I used to think that like okay I'm just gonna brute force work super hard push through every single day and wake up caffeinate work you know and repeat um and I think that that's really good for building skills and building stamina and I think at some point uh you got to be focused right having clarity of like what are your goals and and things like that. And so yeah um and the the whole luck thing you know I totally get that like the harder you work you create your luck you know you create your surface level your your surface area of like potential to be lucky and so but I I think like the more successful people that I met uh that I meet the more I realize that yeah people do the most successful people recognize that they're lucky it's not just being humble I think it's also recognizing that maybe there's a lot of things in the world that you cannot control but what you can control um you know is is how hard you work and also whose opinions matter at the end of the day. And this is a big shift for me where I think maybe 10 years ago I heard this Brene Brown thing where she said for her to battle uh this noise that you know people's opinion she had to write down in a very small piece of paper the five names uh that matters the five names whose opinion matters to her and keep that very close. And and anytime you get distracted just take a look at that and remember actually most things don't matter and most people's opinion don't matter and in fact most people don't matter. And I think that level of clarity really helped me.

AI’s Role In Recruiting And Culture Fit

SPEAKER_00 40:33

Yeah and I think too another thing that uh that stuck out to me is like we tend to care a lot more about what people think about us than what they actually care. Like we care so much more about what they think and we think they care so much more than they really do and let that bog us down, you know?

SPEAKER_01 40:51

Yeah actually this quote uh really stuck with me I heard it like a few weeks ago which is we suffer much more in imagination than in reality.

SPEAKER_00 41:01

Yeah. I there's a there's a Mark Twain quote that's similar and he was he said that uh he's failed so much more often in his mind than he than in reality. Yeah something like that. Um he's he's worried about so many things that never came to be um you know the that kind of thing but um well so with you being a founder and you have a team it sounds like now around you where where do you find the most value in your time? Like where do you where do you say focus now with with having a team around you and and being a founder.

SPEAKER_01 41:34

Yeah so I built the company in a way that complimented me. So everything that I did not like to do it is outsourced and everything I like to do or at least I'm remotely good at is uh kept on my plate. So my focus has been just go to market. So I'm getting on more podcasts just practicing and understanding what kind of stories I want to tell. And that's the whole purpose of getting on you know more YouTube and podcasts now. So yeah I'm just really spending all my time on going to market getting the users talking to users understanding what works what doesn't for them and then eventually when we have more users I want to be able to tell user stories because I think those stories can inspire others to take action and so in some ways I'm like a chief storyteller of the company.

SPEAKER_00 42:23

Yeah that's great. That's really that's really good. Yeah for me um with my business it's tough because it is a service based business so um I'm still in the in the weeds of things still um but I I don't want to fully be out of you know client interaction or recruit or recruiting um but yeah fight figuring out what I can you know outsource and you know I have some 1099 people who work with me and um you know uh it's tough to figure out what what to outsource and what to take off my own plate. There's a lot of stuff that like I know I don't want to do like a finance and accounting and and stuff like that that is easy to outsource and that I do do that. And uh my time's just not spent valuably doing that.

SPEAKER_01 43:08

So yeah it's like it's like being a bookkeeper is the most important and the most boring job sometimes but it is the most important job. And so yeah now I'm I'm helping uh my parents out with closing books for the year for a logistics business and it's like it's dry it's transaction by transaction it's it's like every APAR but it's necessary. It's it's what cash flow you know counts on to to just have good books.

SPEAKER_00 43:39

So yeah. I I had someone gave me a good piece of advice about that like the outsourcing and and stuff you know to if you try to think about like what you want to earn in a year and and so calculate that out to what would you make hourly and then could you pay someone else less than what you would pay yourself to do that same job. Much less like accounting I would pay someone else probably less than what I want to pay myself to do that and they would do it better than I would do it and more efficiently. So um that that was good advice.

SPEAKER_01 44:12

The this book really changed a way Looked at money. Um, it's from Remit Seti. It's called I Will Teach You to Be Rich. Okay. Yeah, it's uh it's a the title itself doesn't do the book justice, but it is a good book. And part of it talks about um how do you turn up your money doll on the things that you enjoy? So if you enjoyed going on going to nice restaurants, what would 10x of that look like? And so if you what kind of task do you enjoy that provides the most output in your in your company? What would like 10x of that look like? And then how do you like get rid of all the things that you don't really enjoy to do? And of course, you know, business is business, and being the owner, you gotta probably do a lot of things you may not love to do. But I think it's it's a fun little practice, I think, in your mind to do that. And then the other thing that really got to me um is totally off topic from being a business owner. I think more of so being a father is like this this concept of memory dividend. It's from this book called Die With Zero. And and in many ways, this book inspired my business as well. Uh, it's it's that you know, sometimes you enjoy, you want to spend the money and the time early on in your life to enjoy the things that you want to keep a memory because you get to enjoy that memory for longer if you have it earlier. And so, like as a business owner, your time you have 24 hours in a day. So the the more ability you're you can outsource things, the more time you have to spend with your kids. And now that they're young, you get to enjoy the memory much longer. And so that's something I think about a lot with what I'm doing now. It's like with every startup that I've had before, I've just worked all the time, like 80-hour weeks. You know, I'm just like always glued to my computer doing something. But this time around, I'm trying to be more intentional about how I spend my time so that I don't do that again and take away all my time from the people I love.

Finding Co‑Founders With High Agency

SPEAKER_00 46:15

Yeah, that was a tough dynamic when we, you know, before we had our first uh child, I was probably working 70, 80 hours a week. And so trying to figure out how to have that work-life balance and have time with, you know, especially at firstborn, um, was a definitely a shift because you know you're responsible for someone else. And you know, I had my wife, obviously, but um now you have this little person that needs your attention. And um, at that time I I'd for a while I tried to tell myself, like, hey, here are my set hours that I'm gonna work, and then after that I'm cutting off. And I that scared me to do that, and I didn't really want to, but after I did that, I it I tended to find a way to get things done. I became more efficient, like I was able to get what I needed to and prioritize what I needed to in that time. Of course, there were some outliers where there's be a phone call I had to take or whatever, but I that really helped me a lot with the work-life balance and not getting burned out too.

SPEAKER_01 47:17

So yeah, and that's when you realize the greatest blessing of starting your own business is the freedom of time, right? Yeah, yeah. It's uh it's worth all the stress and everything to to be able to just hang out with your kids whenever you want to.

SPEAKER_00 47:31

Yeah, exactly. Well, so what would you um as we kind of close here, what what advice would you give to people on the fence about getting an entrepreneurship? What would you kind of tell them?

SPEAKER_01 47:44

Oh, general advices are really tough. I I think it is tough. If you uh, you know, one framework you can try to lean into is what would you regret more looking back five years from now? Yeah. I think sometimes when I don't know what to do, I I think about that. Or in a more positive note, what would make a better story when when you're when you're all said and done? What would make a better story? But I think for most people, having a safety net is always you know the thing that helps them take the leap. Just like, yeah, what kind of safety net can you provide yourself before taking that leap? Uh for some people it's like a verbal offer of a job that you know to do something they're really good at, or to start doing some site hustles where they can make more money per hour than they do at their job right now, doing the same thing, maybe, and that frees them up sometime to do something else to start a business. Yeah. But I don't think I've met anyone who's regret taking a leap even if they failed. Yeah. Um times may be tough, but uh who is it that say this? I think it's Alex Hermozzi on YouTube that say that uh you only you only fail if you quit.

SPEAKER_00 48:56

Yeah. Yeah. Yeah, or if you don't ever try, you know. I mean, that that would be the advice I would give is just try. Like, you know, if you have an idea, test it, you know, test the market, um, even give it away for free and see, you know, what the response you get from the market is, if it's if it's a you know a viable uh idea. But just take the first step. Like you know, sitting around thinking about it is gonna be harder than just taking that first step. Um, and like you said, are you what would you regret more, you know, in five years or however long? Um, so that would be the advice I would give is just take that first step and and you know, test the market and see see what you know comes back to you.

SPEAKER_01 49:38

So yeah, I think my my suspicion is that a lot of people don't take the first step because of the fear of judgment of the people closest to them. You know, the what what would some person think if I failed? I think that's that's a pretty big block. And I think that's just human, right? We care about the people we socialize with. Yeah. And to not care that means you're a sociopath, probably. So it's good, it's good that we care. Uh and I and to that, I would say that Teddy Roosevelt quote about the man in the arena. I love that. It's that most yeah, people's opinion don't always weigh the same. You know, someone's I I always respect someone who tries.

SPEAKER_00 50:24

Yeah. And I agree. Yeah. Yeah. You know, and I remember when I when I started transparent staffing, I'd wanted to get into entrepreneurship since like high school and wanted to work for myself. And um, so my wife knew that. I we talked about it, and I talked about wanting to quit my job and start a business, and she was always very hesitant about it. And um, she came from a background where they always struggled with finances and um not struggled, but just it was something that they had to worry about. And um, so that idea of like taking that kind of risk was like very scary to her. And so I just started the company and got my first contract, and that was the first thing that she saw. I I printed out my first contract with a client that I got and went and showed it to her, and she was just like, Oh, this is real, like you're like this that just made her more comfortable, like, okay, you've done it, like versus like this, you know, most people the biggest fear they have is of the unknown, you know, that they fear the unknown, and so that helped with her comfort comfortability, I guess.

SPEAKER_01 51:28

So, yeah, and good on you for having empathy, you know, for her for the way she grew up or or her background, you know, to to kind of calm those nerves a little bit.

SPEAKER_00 51:39

Yeah, yeah, yeah. Well, um, well, tell us a little bit, uh, you know, kinda kind of as we wrap up here, where where can we find airlight and where can we find you and connect with you?

SPEAKER_01 51:49

Yeah, I'm at E E Jermaine, E E J E R M A I N E, everywhere on social media. And airlight is airlight.com, H E I R L I G H T.com. So depending on when you're watching this or listening to this, we may or may not be live in your state, but uh keep following along.

SPEAKER_00 52:07

Yeah, well, I'll I'll leave I can leave links in the show notes as well so they can find you. And uh yeah, thank you so much for for being on the podcast. I appreciate it. It's been it's been a great conversation. Thanks, Nick.