Jermaine Ee

Bio

Short Bio: Jermaine Ee is a founder and storyteller obsessed with how we spend our time, the work we do, and what we leave behind. He’s currently building HeirLight, a simple & smart will maker that turns avoided conversations about family, money, and legacy into a calm, 30‑minute guided experience.

Longer Bio: Jermaine Ee is a founder and storyteller interested in three things: how we spend our time, the work we do, and what we leave behind. His career has zigzagged across ed‑tech, logistics, toys, political campaigns, executive search, and impact projects, but the through‑line has always been the same: helping people make better decisions about their money, careers, and futures. He’s run financial aid workshops in low‑income high schools, built a startup to help kids confront their fear of math, and worked inside the VC/PE ecosystem studying how talent shapes enduring companies. Through Rotary and other efforts, he has helped lead humanitarian projects from Los Angeles to Colombia, Mexico, and Ukraine, where he worked on refugee housing, medical transport, and frontline logistics. Today Jermaine spends most of his time on HeirLight, a simple & smart will maker designed to turn one of adulthood’s most avoided tasks into a fast, modern, emotionally intelligent experience. Born in Los Angeles and raised between LA and Malaysia, he thinks a lot about belonging, identity, and the quiet instructions we leave behind for the people we love. With HeirLight, he’s on a mission to help more families move from fear and procrastination to clarity and calm, starting with a 30‑minute guided conversation that ends with a legally binding will and a little more peace of mind.

Intro

Jermaine Ee's journey as an entrepreneur is marked by a profound understanding of the significance of clarity in planning for the future. During a pivotal lunch conversation with his mother, he discovered that her greatest apprehension was not financial insecurity, but rather the uncertainty surrounding her retirement and estate planning. This revelation propelled him to create Air Light, an innovative platform aimed at simplifying the will-making process through AI technology, thereby alleviating the confusion that often accompanies estate planning. Throughout our dialogue, Jermaine candidly reflects on his diverse entrepreneurial experiences, from launching a toy company at the age of 17 to navigating the complexities of augmented reality and political campaigns. His commitment to fostering understanding and clarity in an often daunting landscape serves as a testament to his resilience and adaptability in the face of challenges.

Conversation

The discussion with Jermaine Ee, a serial entrepreneur with a diverse background, reveals the profound insights he has gained from his extensive entrepreneurial journey. Jermaine's narrative begins with his early ventures, including a toy company he launched at the age of seventeen, which provided him with foundational skills in product placement and retail strategy. His experiences span various industries, from augmented reality to education, each shaped by pivotal moments that tested his resolve and adaptability. A key theme emerges as Jermaine recounts a lunch conversation with his mother, which exposed a deeper fear of clarity rather than financial insecurity. This realization propelled him to develop Air Light, an innovative platform focused on estate planning and personal asset management, addressing a significant gap in the market where a staggering 70% of Americans lack a will. Jermaine's candid reflections on his past mistakes, particularly his conflict avoidance, underscore the importance of communication in leadership. He emphasizes that real success lies not in chasing accolades, but in creating meaningful impact and nurturing relationships, a sentiment that resonates deeply in today's fast-paced entrepreneurial landscape.

Takeaways

• Jermaine Ee's journey reflects the importance of learning from mistakes, emphasizing the necessity of confronting issues promptly to foster growth.
• The concept of grit is central to entrepreneurship, where resilience and the ability to show up daily are crucial for overcoming challenges.
• Jermaine's perspective on cultural influences highlights how diverse backgrounds shape entrepreneurial mindsets and approaches to business.
• Air Light, Jermaine's startup, addresses the critical need for clarity in estate planning, particularly emphasizing the emotional aspects of financial security.
• Conflict avoidance can be detrimental to business success, as it often leads to unresolved issues that can accumulate over time, causing greater harm.
• The practice of maintaining a gratitude journal can help entrepreneurs manage uncertainty and align their expectations with reality.

• LinkedIn
• Facebook
• Instagram
• X
• Who Says You Can't Startup | Full Bundle | Incorrigible Entrepreneur - The online course for startup founders
• Our YouTube channel
• Designing Successful Startups — Jothy Rosenberg | Author | Speaker | Podcaster - Site with all podcasts
• Tech Startup Toolkit book
• Please leave us a review

Hello. Please meet today's guest, Jermaine E. In.

What would you do if a simple lunch conversation with your mom revealed that her biggest fear wasn't running out of money, it was running out of clarity? That's exactly what happened to today's guest, Jermaine E. And it sparked his latest venture, Air Light.

Jermaine is a serial entrepreneur who started his first company at 17, a toy brand selling to Walmart and Target.

Since then, he's built augmented reality filters for Snapchat, worked on a California gubernatorial campaign where he got a behind the scenes look at how power really works, scaled an education franchise to five locations before COVID hit, and now he's tackling estate planning with AI. But here's what makes Jermaine different. He's brutally honest about his mistakes, like how being conflict avoidant nearly sank one of his businesses.

And he's figured out that the game isn't about chasing TechCrunch headlines anymore. It's about building something that actually matters.

This conversation is packed with hard won wisdom about grit, the courage to challenge assumptions, and why showing up one day at a time might be the most powerful strategy of all. Hello, Jermaine, and welcome to the podcast.

Thank you. Thanks for having me.

I am very happy to have you here. Hey, I always start with a context setting question, which is where are you originally from and where do you live now?

Well, I currently live in a city called Alhambra. It's next to Pasadena. And I always have to qualify that because sometimes I say Los Angeles. That's what most people would know.

But Alhambra and Pasadena both have a very cool story. My family is Chinese Malaysian. And so when, when I was growing up, I wanted to be as American as I can be.

So I will never say that, but as I get older, I got reconnected from my roots a little bit more. I'm pretty proud to say that I am a American. Malaysian Chinese.

Excellent. Were you actually born in. In the US or were you born in Malaysia?

Yeah, I was born in the U.S. in fact, just a mile away from here. Okay, yeah.

And have you gone back to visit where your roots are?

Yes, often, in fact.

And I do speak all the languages too, so English is actually my third language, so I learned Mandarin first and then I learned Malay and then I mostly speak English these days, but then, yeah, English is my third language. I've gone on to pick up some Spanish and I'm currently learning Ukrainian. So it's a whole host of languages.

Well, that is a skill to speak many languages.

I, I think the words in languages kind of shapes the worldview that we have. So I'll give, I'll tell you a short story of when I started learning Spanish that I, I learned of Spanish. There's two words to describe happiness.

One is feliz, which is like an active role of happiness, active feeling of happiness. And the second one is contento, which is content and that is equally happiness.

And if you kind of think about the way a lot of Spanish speaking countries are, people are more content than they are feliz and active happiness.

And I learned that during COVID when, you know, the world was shut down and I was picking up a new language and I was always wondering why are people so happy in Spanish speaking countries? Mostly that's a, that's a huge generalization.

But, but I think, yeah, languages really shape the way we look at the world and, and I've really had a lot of fun learning.

Well, speaking of worldview, how would you say your cultural background has affected your worldview and your or. And does it affect the way your an entrepreneur, the way you practice your entrepreneurship?

I think it's shifting constantly. You know, maybe when I was younger, I think my cultural background, which is Los Angeles, I went to usc.

It's like a very American productivity driven culture. It's like we measure our self worth based on our productivity, our ability to do things in this marketplace.

And we measure by GDP, by AUM, by 401ks, you know, just a 401A. Sorry, just by valuations and things like that.

And as I get reconnected with my roots a little bit, I just started to see the alternative ways of living life, of thinking about what makes a meaningful life. And so it certainly has changed a lot of what I've been doing. So I think all throughout my 20s I chased what was fun.

Maybe it was fun, but certainly there was a huge aspect of it, of chasing the TechCrunch headline or the Business Insider X or Jermaine raised X amount of money on X valuation. And I've, I did a lot of that in my 20s and I think now in my mid-30s, I am more in touch with what is important to me.

And so that's what I, I think that's the biggest change that I've had since, you know, growing up the last decade or so.

So your current startup, which we're going to talk about in a few minutes, is called Air Light, where it's spelled H E I R. So as in, you know, your heirs in, in a estate planning sense. We're going to come back to that in a minute.

But prior to, to this startup, what other startups, what other companies had you worked at or created yourself along the way?

Yeah, so I started when I was 17 at a toy company, so a classic CPG brand and we sold to Walmart, Target, I think Walgreens. So that's where we're distributed. So the big players.

And to give you a context of the size though, Mattel is, let's say Mattel is 100 and we're probably around 20 in terms of percentage of size of company. So it's not a small company, it's global distribution.

So that's where I first started learning about, you know, how do you set, how do you pitch a product to get into retail packaging that matters, putting things on the shelf, eye level, font size, color psychology around things like that and what it's place next to and all these factors in retail. It was super fun. That was my first job. And then I started a company, as I mentioned earlier, to do AR filters.

This was when Snapchat was just taking off. And so we helped companies learn how to geofence and put branding on Snapchat basically and a bunch of things happened.

But I thought I didn't want to spend the rest of my time selling augmented reality filters on a social media app. I wanted to do a little bit more and understand how the world worked a little bit more.

And so I cold emailed the then treasurer of California, the state treasurer and I got a job on his campaign. And so I worked for 18 months as his finance deputy to just understand how this world worked.

And being the treasurer is fascinating because the treasurer is essentially the banker of the state and being at the time the sixth largest economy in the world.

I got to sit in conversations that really showed me how the world works and sit in conversations with labor unions, with in his case, the Democrat party, to understand who in this world makes the decisions and how are House power brokered, how does funds affect elections and things like that, and really shaped a lot of how I look at the world moving forward. And then later on I moved to New York when the campaign ended.

We had lost the campaign to now the current governor of California, Gavin Newsom, and started a education company. So I had raised money on the idea that I would build a franchisable model. So we had the goal of raising Money to do 10 locations.

We got to location five and we were ramping up six and seven. We were negotiating leases and things like that. And that's when Covid hit.

And so, you know, it's, it was kind of a, it was probably one of the most difficult time to run a physical education business during a pandemic and all that to say the business is still going in a new form in a completely different shell. And then I moved on to do a lot of projects on the side.

I had a Instagram company doing dog products that we sold off to someone in Japan actually of all places. And I did executive search for a while for PE and VC backed companies and that was very fascinating as well.

And in my journey of just zigzagging through all these things, I ended up doing something that speaks to who I am as a person. I think Airlight is a reflection of who I am as a person now, which we can talk about later.

I probably missed out a bunch of things in between, but I've got a few investments here and there that I advise and spend a lot of time on. And yeah, that's, I think I missed a few in there.

Well, that's, that's okay.

But, but before we leave the, the sort of journey part of this conversation, were there any, well, shall we call them mistakes or learning experiences in any of those that kind of shaped how you're doing things with this current startup?

There isn't a specific mistake that I can tie to at the current startup just because it's so new. However, I've always thought of the world of startups in kind of a three prong.

And this was put clearly in a framework for me by someone that I really admire that I learned a lot from. His name is Todd Gitlin, probably one of the best growth stage VC recruiters that I know.

And that's why I went to work with him and learn from him, I should say. I work for him.

So, you know, he explained to me about three years ago now that there's ideas are everywhere, capital is everywhere, and the one thing that really changes is your ability to know how to put the right talent in the right time and place to form this team. And the reason why this resonated with me a lot is because when I was building my education startup, I am conflict avoidant.

And so I had a center manager for one of the locations. I had hired her.

I knew, I knew she wasn't doing everything to the SOP that we had set, but because I was putting it off for so long that things got really out of hand maybe a year down the road. And I was just very, very bad at confronting this conversation.

And so at some point, things got so bad that accounting was completely off and cash flow projections were completely off. Sign up rates are off, churn rates were off. And I had to own up to it. I just had to talk to her and essentially fire her.

And I think the thing that was so difficult there was that because I was so conflict avoidant, I never gave her the chance to improve because I never gave her the feedback that she needed to make sure that all the systems were working properly or I never inquired why were things not working properly. And so I think that was a huge lesson for me. I think it was completely my fault.

It was my lack of ability to be candid and to have these difficult conversations that set up the business to take a big hit on that location. And so I think moving forward, I've tried and this is still something I'm working on.

I'm still not great at it, but now I understand more the urgency of this.

It's always hard, it's for everybody to deal with those blunt conversations that you have to have. Sometimes I can do them, but they're never, they're never easy.

I think it's like sometimes if I think of it as my fault is an I take the responsibility fold aside, it is easier because at the end of the day, I could have let her go, fired her based on, you know, her lack of performance. But if I'm being honest with myself, I knew this probably months ago. I think I want to say 8 to 10 months ago until the day.

I think the hardest firing, though, that I've ever done is that when we ran out of money at some point and having to let people go. This is right before the PPP kicked in back in Covid days. I think that was probably the hardest.

I think it was in some ways an admission of my inability to execute and to manage our financials to the Point where I made a promise to someone to bring them on and I had to backtrack on that promise. That's how I looked at it.

And of course, business is business, but I think there is such a human side of it that really took me down for a few days, maybe a few weeks. I still think about it sometimes.

Sorry for the interruption, but in addition to the podcast, you might also be interested in the online program I've created for startup founders called who says you can't start up in it, I have tried to capture everything I've learned in the course of founding and running nine startups over 37 years. It's four courses, each one about 15 video lessons, plus over 130 downloadable resources across all four courses.

Each course individually is only $375. The QR code will take you where you can learn more. Now back to the podcast.

As a founder of a startup, one of the challenges we all face is that you can't make decisions. You can't wait to make decisions on all the information being laid out. There's always a lot of uncertainty.

It's hard for some founders to deal with that and others are very, are very comfortable with it. What is your relationship with that inherent uncertainty that you're faced with in a startup?

I think for me there's a few layers. If the uncertainty is a, a decision, a business decision that does not affect personnel life, I generally am not too concerned about it.

I have a baseline that I always go back to for, actually for everything in my life. You know, I've, I always, I'm very lucky that I have a very strong support system.

So I know that my worst case scenario is I'll start another startup that's the absolute worst case scenario. But in between the absolute worst case scenario to whatever the decision's worst case scenario is, the entire gap is typically very clear to me.

And so I have a journaling practice that I do. And so I, I try to stick onto my schedule on Sundays. And it's simple. I ask myself what I'm grateful for in detail.

So not health, weather and things like that. So I try to be really, really clear. What am I grateful for in that moment?

And then I try to write down also things that I'm looking forward to and also things that I'm frustrated by. And what I realized that when I start writing down the things that I am frustrated by, it typically traces back to very simple things.

Things like perhaps my expectation is misaligned with the reality. And so sometimes it's just Understanding that adjusting the expectation of the outcome and just let it be because the market is not controllable.

And so I am in love with the game of building businesses. And so with that, I fully understand that risk and uncertainty is part of it.

And perhaps this is a little bit of a stoic mindset or a Buddhist mindset, which is things happen and how we react to it and how we do or do not assign a suffering or painful feeling to it helps us move on and react, you know, keep going. And so, yeah, I think that's generally how I look at it. Let me think about what a younger me would do, though.

I think a younger me would put my head down and just grind it out and blame myself for it. I've been very bad at taking up. Actually, I'm still pretty bad at this. I'm pretty bad at taking it too personally.

And I think that's something I got to work on.

Well, so now tell us what Air Light does and what drove you to create it.

Airlight is a simple will maker.

And what drove me to it wasn't will or estate planning, because one day my parents and I, we had a lunch at a Thai restaurant down the street from this co working space that we have. And my mom was 61. She has passed away since, but she was 61 at the time.

And, you know, I asked her, how, how long do you want to keep working hard for?

Because I'd like to travel with you before you can no longer climb the steps of the Great Wall or, you know, go down to the beach down on a cliff somewhere in Portugal. And so this conversation unveiled something that made me realize that her anxiety and uncertainty around retirement wasn't a lack of resources.

It was a lack of clarity. It's a lack of clarity of how does her 401k translate into the rest of her life? What does it look like?

And underneath of all of that, it's a quiet fear of running out of money before you die. I think this is a phenomenon that we're seeing all over the country, especially in the US where it's a very individualistic country.

So places, for example, like Malaysia, where my family is from, it's much more communal. So people live in generational household where they support each other. And so that fear is different.

So with that, I set out to build a GPT to an AI agent, essentially to chat with my mom in the language that she prefers, which could be English today and Mandarin tomorrow, and whatever she chooses to write down and save the inventory of her life. So the people that she cares about, the stories of her friendship from 40 years ago that suddenly came back up and she just wanted to write it down.

The things that she owned, like a china that maybe she got long time ago that she forgot about and she has a story attached to it.

So I started building on this, this vertical and what I realized is if I have your assets and your relationships, I'm actually able to make a will for you. And since 70% Americans don't have a will, this could be an interesting business.

What we ended up doing though is that we, we set up a trust for my parents because a lot of people should have a trust but due to inaction, due to the lack of information, due to just procrastination, a lot of people don't do it.

And then there's also a lot of people with just the fear of like taking up this conversation, seemingly serious and huge conversation with a total stranger and attorney and it feels like a daunting task and so they just don't do it.

And so we built an app that essentially has a conversation with you and we cannot give you legal advice, but what we can is to as quick as possible understand what we're working with and present you with the best practices.

And our goal is just to help you translate your wishes in plain English or Spanish eventually into a legally valid document that is specific to your state. And so that's what we're building.

And how's it going?

Well, we over engineered it. We, the three of us, my two engineers and I, two co founders and I, we started building out everything we thought was needed.

And what we realized was that we had missed out on a key factor which is someone who is using our app requires a little bit more handholding, a little bit more guidance in the sense of language as well as design.

So we are now in a process of refining our UI UX to make it much easier and a little bit more intuitive for someone who's never thought of what is a executor. What is a guardian in relates to estate planning. So that's what we're up to right now.

Well, you've really jumped to a, from a lot of different markets and products. Politics, executive search, education, logistics.

I'm going to leave something out and now estate planning, which says to me first of all that you, you don't have much fear about jumping into something new if you think that it's needed and you have the passion to, to push it. And you know, I love hearing this the kind of story you just Told where it's something about your mother's situation, financial situation, that.

That drove you. That's the kind of, you know, root of a very strong passion for something. But my question here is a little bit different. It's about the mindset of.

Of learning something new and just diving in with both feet. Talk a little bit about your mindset around learning something new.

Yeah. In the beginning, right out of college, it wasn't a choice because I was someone who was unhirable.

I feel like I had a great college degree, but I didn't have great work experience. And I just didn't fit into the mold of someone who would go. Actually, I did have a job offer from Oracle.

As a salesperson, I think I probably would have done okay doing software sales and seeing the trajectory of my friends who did that. They have a very comfortable life. And so that could have been. That could have been a play for me.

But aside from selling, I think I was forced into an entrepreneur role because I just could not sit still when I see that something can be done better or something can be done differently. And I give my dad a lot of credit. You know, my dad is someone who. Both my parents came to the US with nothing. And my dad, he.

He was a janitor at a funeral home in Oklahoma when he was 25 years old. And while he. He probably will not be out there talking about this, but he is comfortably a millionaire.

And so for me, the ability for him to jump from where he was, where he started in his journey in this country to. He's now 62, I think. Yeah, 62. It just gives me so much strength because I watch him fall down and get back up and fall down and try something new.

And this relentlessness, this grit, I think, is what kept me going. But the ability to learn, I believe that just came from my curiosity.

I think it's just like I. I thought, you know, the world is, as Steve Jobs say, made up by people who are no smarter than you and I.

And watching my former boss, the state treasurer of California, who also had a similar story of working at a restaurant in Georgetown, I believe, in Washington, D.C. into becoming the treasurer of California. I think these were all examples in my life that I sought out, you know, to. I sought out the treasurer because he had a.

A life that I wanted to understand. How can someone start from where they are and jump in one generation to achieve such excellence?

And so I think I learned a lot from how they function, which is to always challenge assumptions and sometimes to never take no for an Answer.

There's one thing that I've been working on and I heard this concept, I'm not sure I think from Steven Bartlett actually, of the paper walls, of pushing the walls around you to see if it can be moved or if you can poke a hole through it or just run through it.

And so oftentimes when I speak with my co founders, my two engineers who are building the app, you know, we would have conversations about timelines and I would ask him, hey, how long, how long would it take for us to download and index the entire probate code of California and make sure AI is guardrailed in the right places so that we don't give bad advice or we don't draft a bad will for our clients? Then they'll give me a date and I'll say, well, what about the other 49 states? Can we do that in a record time? What can we learn?

What processes can we put in to take our learnings from the first one and scale it up? And I think this is a mindset that I've adopted in the past few years of talking to really smart people while doing executive search.

And so curiosity has always been my driver. And I think I just, along the way picked up more confidence along and started applying it to more intensely.

Hi. The podcast you are listening to is a companion to my recent book, Tech startup Toolkit, how to Launch Strong and Exit Big.

This is the book I wish I'd had as I was founding and running eight startups over 35 years. I tell the unvarnished truth about what went right and especially about what went wrong. You could get it from all the usual booksellers.

I hope you like it. It's a true labor of love. Now back to the show. Well, you, you mentioned a few minutes ago, you mentioned grit.

And grit is a concept I like to talk to every guest about. The concept of grit is kind of described by words like resilience and fortitude, drive, determination, stick to it, I ness, and most of all, courage.

It is a true statement that I've now had interviewed 106 people on this podcast and besides them, every founder I've ever known has grit in large measure. It doesn't take long talking to you to realize what you have a lot of grit.

And it's, I'm sure it's helped you immeasurably as you've gone through all these stages of your life. Where do you think your grit comes from?

You.

You obviously tied it to your father already. But is there, you know, is there More to the, to the grit story for you.

I think selfishly, I just wanted to be successful.

I think in, probably in my 20s, it was driven by the need for admiration, the need for validation of, you know, the people's opinion, who I cared about. I think as I gone through a few more iterations of businesses and kept showing up to do the work, sometimes it's a necessity.

And that was great money and the flexibility it afforded me to, to keep building my startup and to drive only during peak hours and then go back to a Starbucks somewhere or a McDonald's somewhere to get a cup of coffee and keep working on it.

I think sometimes it's out of necessity, but I think these days I do believe that there is a era of my life where I want to keep pushing because I'm probably three to four years away from having kids. And I know when I do, I want to be someone who stays home and hangs out a lot and be very present.

And prior to doing that, this current season of my life that I'm in, I'd like to live in my office. I would like to just put everything that I have into the basket and try to give it the best shot that I have.

And so how it evolved is, you know, watching my parents, watching my friends, and I'm very lucky to have older friends. I joined the Rotary Club when I was 23, a move that is strange to a lot of people.

But the benefit of having that is that I was, I had access to a lot of people who were, you know, successful in their career or retiring or retired.

And the stories that they told me, you know, sometimes ends up being something like, you know, I wish I did something not because I couldn't, I can't do it now, but because it doesn't make sense. So for example, now I'm, I'm 34 now. I wouldn't like to stay in hostels and backpack through Europe as 34 year old.

And I'm really glad I did that at 25, because that was the prime time to do it. Perhaps 25, you know, could be also a little late.

Maybe 18 was the right time to do it because the experience Just would be different right at 20, 34 versus at 18.

Um, so I'm trying to remind myself now every day that, you know, sometime in the future I'll look back at 34 and be grateful that I went all up for my startup because maybe at 44, all I want to do is just hang around and maybe play basketball with my kid or something like that, and that will be a different season of my life. And grit shows up differently, Dan.

Prof. Well, it's going to be important that you teach or convey your concepts of grit to your kids. I mean, you're going to want them to have grit too. Not necessarily for startups.

They don't need to do startups if they don't want to, but we, we all can use some grit in life.

So school smart and now street smart. But at the time he was school smart.

He got most of his validation from studying and he is, you know, he went to a top 10 chemical engineering program in the country and now he is a chemical engineer working in a lab right now.

The market slowed down a little bit and people were not hiring as much. And around the same time, the Ukraine war started.

And so I had made a deal with him on his graduation that I would buy him a flight to anywhere in the world as long as he did something for someone without getting anything in return. To his credit, he decided to go volunteer at a refugee center in Warsaw, in Poland. And when he arrived, he bought a one way ticket.

And when he arrived, the first week was brutal. I think it broke him because for the first time in his life, he was in a situation where nobody looked like him.

People barely spoke his language, English, and he didn't know how to use a laundry machine. He didn't know how to get change to buy food for himself. And we were on the phone and we had this conversation.

I remember so clearly that I told him that you can't come back now because you can or you can take it one day at a time.

Just decide tomorrow to show up back at the center and just do one thing and then spend the rest of your day sitting in a cafe watching YouTube or whatever you want or walk around the city. But if you just keep showing up one day at a time, it's going to get easier. And he ended up staying there for three months.

And the relationships that he built with not only the Ukrainians at the center, but also the organizer helping her put on a fundraiser to raise money and to then travel around Europe completely changed him. It gave him the confidence to now move to a new city to try. He's now ballroom dancing.

He's learning all these new skills because now he has the confidence to do so. And so I think a lot about that.

And I think every time I talk to a younger person, I would always advise them to do something completely out of your comfort zone and know that of course you can always come home, but just to show up every day. And also I try to push them to stand for something.

Because when my little brother, the Same brother was 15, I think, or 16, that's when I was working on the political campaign and I had him go stand on the street to gather signatures. And that was the first time in his life that he had to face rejection at like a 95% rate as well as to stand up for something.

Because when you're asking for signature, you have to defend what you believe in and choose a side. And I think this is a skill that we don't practice too often these days.

Well, you're right to focus on his self confidence or lack of it. And now he has a lot more of it.

I, I actually gave a TED talk on this subject because when someone at almost any age, through whatever might happen to them, but if you become disabled, you tend to lose your self esteem and that brings down your self confidence as well. And that's a bad state to be in. But a lot of disabled people, most, I would say, and I've known quite a few, fight back in a very constructive way.

And they do it by finding something they want to do. But, but right now it seems too hard to do because of their disability.

And I'm mostly thinking about sports because sports turns out to be something where if you put your heart into it and you work hard at it, you can get good at a sport. I don't mean Olympics good, but good better than the average person in the population.

And as soon as that starts to happen and you exceed your expectations, and more importantly everyone else's expectations of you, you start to build your self Confidence up and you can do it a little tiny step at a time and it's, it's just amazing to watch.

And, and I help and I have a foundation where I help kids who've become disabled get into a sport they want to by us getting them adaptive equipment that makes that sport possible.

Like for example, they lose a leg and we get them a running leg which has one of those blade feet on it and it's hard to learn how to use that and it takes a lot of falling, a lot of work, a lot of time. But they have, they're so motivated and they succeed. And then oh my God, the looks on their faces.

These kids I focus on, only on kids and they succeed and it's now their self esteem is up, their self confidence is up and it affects in a positive way, affects everything else in their life. When they start doing better at school, they start having, have more and better friendships and it's amazing.

So you know, kudos to you for helping your brother build such an important aspect of one's personality.

Yeah, that was actually the focus of my startup in New York. It was to help kids gain the confidence to learn. And I had met this woman, her name was Zhang He Li and she was the record holder of mental math.

And so what ended up happening is we, we hooked up her brain to this machine in Stanford to read the neural waves that she, she had during, when she's doing this mental calculations and created a curriculum to help kids build their frontal cortex.

So kids four to six, when you're doing tactile audio visual exercises, you end up building your frontal cortex which in turn informs your executive function, your ability to focus and at the end of it, your confidence to learn.

And we watch so many kids, we actually did this, this little documentary where we sent her to a school, underperforming school in somewhere in New Jersey and to watch the kids light up when they realize that they're smart, they can do something. That's a feeling that's, I mean it's so, so much, it brings so much joy to me and so much fulfillment to me.

And that was the startup that we tried to scale up for an franchising model. And I realized at that point because we studied the economics of franchising so much that you know, franchising works for some people.

It's just like, it's like assisted entrepreneurship in some way, but it works. But for someone like me, it would probably destroy me because the lack of flexibility. But that's a whole nother topic.

Well, the stories you've told have been phenomenal and I really appreciate you coming on to this podcast of mine and sharing them. It's been eye opening. So thank you.

Thank you for having me and here.

Are your toolkit takeaways. Toolkit Number one Conflict avoidance is a slow poison for your startup Jermaine learned this the hard way.

He avoided a difficult conversation with a manager for 10 months, never giving her the feedback she needed to improve. By the time he finally acted, the damage was done. If you know something needs to be said, say it now.

Every day you wait makes it harder and more costly. Toolkit 2 push on the paper walls Germaine talks about testing every boundary to see if it moves. Can you poke a hole through it?

Or maybe just run right through it? When his engineers gave him a timeline, he asked, what about scaling that to all 50 states? What would it take?

Most limitations are assumptions, not facts. Challenge them. Toolkit number grit isn't about grinding forever. It's about showing up one day at a time.

When Jermaine's brother was struggling in Warsaw, feeling completely overwhelmed, Jermaine told him, just decide tomorrow to show up and do one thing. That's it. The rest will follow. Sustainable grit comes from taking it one day at a time. Now go have that difficult conversation you've been avoiding.

Your startup will thank you for that is our show with Jermaine. The show notes contain useful resources and links.

Please follow and rate us@podchaser.com DesigningSuccessful startups also, please share and like us on your social media channels. This is Jothy Rosenberg saying TTFN Tata for now.