How to Raise Entrepreneurial Kids

Episode 17 May 25, 2026 00:32:38
How to Raise Entrepreneurial Kids
Rich and Remote with Alex and Karla Booth
How to Raise Entrepreneurial Kids

May 25 2026 | 00:32:38

/

Show Notes

Mother’s Day, Father’s Day, family, freedom, business, and childhood all collided into one deeply personal conversation on Rich and Remote.

In this episode, Karla reflects on the childhood experiences, parenting dynamics, and life lessons that quietly shaped her entrepreneurial mindset long before business was ever part of the conversation.

This is not parenting advice from a parenting expert. It is insight from the perspective of an entrepreneurial child looking back and recognizing what actually mattered.

The episode explores independence, responsibility, curiosity, trust, resilience, freedom, and why some environments naturally create entrepreneurial thinking while others unintentionally suppress it.

For founders building families alongside businesses, this conversation will probably hit closer to home than expected.

In this episode:


Connect with Karla

Instagram: @karlastefan

Explore more from Rich and Remote

Website: https://richandremote.com/ 

Learn more about Yap Socials

Website: https://yapsocials.com 

Produced by

Proximity Outsourcing

View Full Transcript

Episode Transcript

[00:00:00] Entrepreneurship didn't begin when I started making money. It actually began when I was taught by my parents, when I was encouraged to think independently, to compete bravely, to give it my all, to create constantly, and to fully believe that my ideas had value. [00:00:20] You weren't born to sit in traffic, work for approval, or wait for Fridays. You were built to be free. [00:00:28] Welcome to Rich and Remote, the show for the ones who dare to do life differently. Here we talk about building businesses that give you choices where you work, how you live, and what you create. [00:00:42] This is for the entrepreneurs who crave freedom, financial freedom, location freedom, and freedom from everyone else's expectations. If you're ready to design a life on your own terms, you're in the right place. [00:00:56] Rich and Remote, hosted by Alex and Carla Booth. [00:01:00] Good morning, and welcome to another episode of Rich and Remote. This is Karla Singh, Son Booth. And today I'm going to talk about something that is very timely because it had just been Mother's Day, so belated, happy Mother's Day to all the moms out there. And Father's Day is coming up as well. That will be the first Sunday of June, if I'm not mistaken. Let me quickly Google it. [00:01:25] Father's Day this year will be on June 21st. So I'm wrong. It's not the first Sunday. But yeah, June 21st will be Father's Day for most of the people in the world. That will be for the US and the Philippines as well, and finally here in Mexico. [00:01:43] So thinking about these celebrations, it definitely made me think about my parents. And so I want to honor my parents by recording this podcast and talking about how to raise entrepreneurial children. [00:01:57] So obviously, I'm not a mom or I'm not a mom yet. My husband and I are not parents yet. But we are excited for that to happen. And we are also excited if it doesn't happen. You know, we're totally chill. We're totally trusting God to just give us this gift and in whatever form it can reach us. And we're just excited for the rest of our lives, whatever that looks like, really living each day intentionally. We are working on our business. We're working on ourselves. We're working on our health. And of course, Rich and Remote is a huge part of our mission and our advocacy in inspiring people to build location, independent businesses and a life that they love to live. And so I am recording this podcast and teaching these lessons from the perspective of the child, the entrepreneurial child. I've always been entrepreneurial. I'll definitely tell you A few stories that will make you believe one 100% that hey, this girl can't be employed. This girl is just destined to be an entrepreneur. So I think that this perspective works because it's not technically parenting advice from a parent. It's insight from the child who can now look back and identify what actually mattered. What mattered in my childhood, what were the things that really made a huge difference in the way that I looked at life and how my viewpoints were shaped by my experiences. [00:03:30] I think that this perspective is powerful for entrepreneur listeners who either want kids someday or are already raising children are thinking about this conversation of whether they want to have children or not. And they are also realizing how their own upbringing shaped their ambition. I think this fits our rich and remote ethos perfectly because entrepreneurship here isn't just about money. It's about freedom, confidence, adaptability and self trust. These are the things that I do definitely saw as a repetitive theme in my childhood. So let me tell you a little bit about my story. So my dad had a job. All throughout his life he had worked for a company. It's one of the biggest gas companies in the world. I think it's now called the Linde Group. It used to be called BOC or British Oxygen Company. They supply oxygen and gases to hospitals, to companies like Pepsi, Coca Cola and Refrigerant. And I don't know the other technicalities, but those are kind of like the words that I kept hearing from my dad growing up. [00:04:38] He was doing sales. I think he was a sales engineer or something like that. And you know, he was my idol. I idolized my dad. My dad was a great leader, a great salesman. He's very talented and intelligent. He actually had two engineering degrees. And my mom was also a very skilled salesperson. [00:04:59] She started, I think, by selling actually how they met. How my parents met is my mom was a sales lady at a bookstore, at an office supply store, kind of like Home Depot in Davao City, Philippines. It was called Bookstar in Legazpi street in Davao City. And they met there. I think my dad was buying, I don't know, paper notebooks and my mom was selling it. And then after that gig, I think she started selling appliances. I used to go to the appliance store, hang out with my mom after school. And then after that she sold, I think, Avon Tupperware, a lot of like similar businesses. [00:05:38] And eventually she moved to real estate on the later parts of her life. So all throughout my life I watched my parents sell stuff all the time. And because we Grew up kind of like lower middle class. I also saw them sell, like, just different, various stuff. I'm not kidding. Like, just like different stuff. Anything that they could sell just to earn extra money. I remembered my dad would even sell meatloaf, like embotido. We call it embotido in the Philippines during Christmas just to make extra money. My mom would sell like pirated CDs and like stuffed toys and touch lamps and. Oh my God, I can't even like remember everything that I watched them sell. And I used to go to their supplier's store and I watch them negotiate and make friends with these people. I watch them network. It was really fun. It was such a good memory of my parents and watching them hustle. And so my mind was open to hustle. I think that was the main thing on how I grew up. Entrepreneurial. I watch my parents sell stuff all the time. And so when did my entrepreneurial journey start? And so I think growing up and watching them sell stuff, I realized that, hey, money is an important thing. You know, money is something that we need to earn. And if you have it, if you earn it, then life will be better and we will be happier. You know, something like that. Obviously, it wasn't everything. My parents were very loving and kind. Honestly, they were just simply perfect people. And I had the privilege of growing up in a very functional and very ideal household. And I loved. That was my. I loved it. I loved my childhood. And so I didn't have like a high allowance and I wanted to make more money. You know, I had like a teeny, teeny allowance and in school, and I just wanted more money. And so I think in fourth grade, I realized that my classroom was in, I think, or on the fifth floor or fourth floor, but it was a pretty high floor for a kid to climb. Our recess was only 20 minutes. And I realized that because of our little legs as kids, we would have to go to the cafeteria, four floors and then buy our snacks. And then because almost everyone in the same grade had the exact time for recess, which was only 20 minutes, you know, the bell rang and that was it. [00:08:04] So to go down four flights of stairs, go to the cafeteria, line up for your snacks, get your snacks, get your change, climb up another four flights of stairs. That took a lot of time and it was very tiring. And I noticed that sometimes we don't even enjoy our snacks or we just forego having snacks altogether. And so I thought, huh, if I could just sell snacks here in the fourth floor in my classroom, then my classmates Wouldn't have to go downstairs to do it. And I can even price it a little bit more because I'm saving them that hassle. And so I started doing that. And you know what? My business was pretty successful. So that was a very, very good business. [00:08:48] My success rate was high and I was very proud of myself. I remember riding the public transport with my mom in the afternoon, and my mom was going to pay, the jeepney driver was going to give the money. And I literally told her mom, and I like, I like, swift her hand away. And I said, don't worry about it. I got it. That was one of the proudest moments that I had in my life. And she was like, what your little snack business making that much money? But it just made me feel so good that I could help my parents. [00:09:20] And so that business evolved. Actually, I had to close that business because I literally got a letter from the principal that I can't do that anymore and that kids should be in school to learn and not to start businesses. I think she's wrong. So I had to stop doing that. But I tried to make money in other ways. I think I started selling Avon or something else, like bracelets. And then I also started selling homework. I started to take money from my classmates and I would just, like, make their homework. And honestly, this, like, hustle continued on until college. I even learned that from if someone was failing and I have to write their paper for them, and if it was a critical paper, like, if they were failing, that I could charge like twice or three times the regular price because it was more critical. And so I learned all these upsell strategies just from, I don't know, opening my eyes. And I remember when I was 17, I also had my first, like, in office side Hustle, which, where I would go into this office at like 10pm, I think, or 9pm and it was a Korean English tutoring business. [00:10:24] I would go online and get on a webcam and teach English to Koreans. [00:10:29] And my dad would pick me up because I would end this job at like midnight. And it was downtown. It was kind of a seedy part of the town as well. I also did SEO writing as early as 17 years old. And I even got a lot of projects that I actually outsourced some of the work to my dad's coworker's wife. And it was so funny because one time the payment was late and I had to pay her from my own allowance because I was so embarrassed and my dad was like, pressuring me. And so, yeah, I think I was outsourcing, I don't know, almost 20 years ago. Right. So I've been in this business for a long time. And then aside from that, in college as well, I did some kiddie party hosting and emceeing on the side, which is like hosting parties. I wasn't expecting experienced public speaker and a competitive debater and had a lot of confidence on stage. And so I actually learned how to twist balloons into, like, animals, and I learned how to entertain kids. [00:11:26] And so I had a lot of side hustles. So I could say I was fully, fully entrepreneurial growing up and nothing could stop me, basically. And so that's my story, and these are my lessons. I think these are the parts of my childhood that really contributed to my growth as an entrepreneur and in having the right mindset and perspective coming into business. I know not everyone will start their business early, and not everyone may start their business at all. Because let me tell you, entrepreneurship is one of the most difficult things in the world. There is a reason why most people are not entrepreneurs. It is not easy. The emotional labor that comes with it, the mental roller coaster, the financial hardship that can come. You know, obviously there's some highs and there's a lot of benefits, and you can have freedom and have a hashtag rich and remote life, but it's not easy to get there. And so here are the six lessons that I learned on how to raise entrepreneurial children. These are the things that my parents did that probably they did not know, that, you know, that they were doing this and that my parents have passed in my 20s. Both of them have passed my 20s. My dad passed away when I was 22, and my mom passed away when I was 28. And so I'm sad that they can't see who I am now, but I hope they're watching from heaven. And I always think about them and I always work hard to make them proud and take care of my sisters, because that's what. That's the job I'm honored to do. So, okay, so number one, my parents encouraged creation and not consumption. A lot of kids today are just consumers. They just consume a lot of content. They just consume food, and they are not creating so much. A few are thought to become creators, to create something with their hands and to have unique ideas. And so I think a lot of entrepreneurial traits start with, like, arts, music, sports, any activity that encourages you to build things. Things like writing, storytelling, like making up stories in your mind, games, performing, and problem solving. I think these are the activities that teach Initiative. These are the activities that teach self expression, resilience, if your first idea did not work, pattern recognition as well, and confidence. [00:13:54] And I think that if you encourage your kid to create things, to create unique things, help them think out of the box, encourage them to know that there's something more than what is given to them, I think that is a very, very good ground to, like, plant those entrepreneurial seeds. And, you know, every entrepreneurial skill that I use today exist first in play, in creation, in art. I used to write a lot of poetry, and poetry is my favorite type of art. I still read a lot of poetry. I used to perform poetry. I would still perform if given the chance. Creative kids, I think, eventually become adults who believe they can make something out of nothing. And I think this is really number one, this is the number one perspective in raising entrepreneurial children, making kids believe that they can make something out of nothing. Number two, and I'm so gung ho on this, let your kids compete. Make them join competitions. Teach them about winning, about losing, about perseverance. Teach them emotional regulation in a way comfort never can, in my opinion. I think that kids need to experience losing, embarrassment, pressure, preparation, and the importance thereof. Discipline, delayed gratification, and how to get up and try again after failing. All of these things may sound difficult and ugly, but trust me, it builds grit like no other. So whether it's like, sports or it's a speech competition, a dance competition, chess or any contest, I think that if you're. If you let your kids compete and you help them build that mental and ideally physical endurance to go through a competition and what it's like to prepare for, like, a competition season, I think that it's so worth it because that taught me a lot. And I learned. I joined a lot of competitions, so I joined journalistic competitions, public speaking, science bees, spelling bees, dance contests. What else did I join? Math bees. And I loved it. I felt that the pressure was a different kind of high because I did lose most of them, but I also won some of them. And let me tell you, that feeling of winning something and fully knowing that I deserved it and I worked hard for it was nothing, like nothing. No other feeling even came close to that feeling. And it taught me that I am a winner. And. And winning only needs to happen once for someone to believe that they are a winner, for someone to really put that in their identity to someone to fully embody that. And I love that. And I know that everyone will lose. You know, no one wins the first time. You will lose. You Will experience losing over and over. And the goal here is not to create like hyper pressure. It is to normalize effort. It is to normalize hardship with the promise of a win or with the promise of a lesson, even if you don't win. And that both of those things are rewards. I think that entrepreneurs, entrepreneurs unusual but predictable relationship with failure. And that relationship can 100% start in their childhood. I personally think that kids who never lose often or never experience a win become adults who cannot handle risk properly. So let your kids compete. It's not too late. Even if they're in high school or college now, encourage this from them, listen to them and what they like and encourage them to go and be the best at that thing. And you know how they can do that? By competing. [00:17:54] My number three tip is reward intelligence openly. One of the best things that you can do for your kids, especially now in the age of AI or artificial intelligence, is to make them nurture their natural intelligence and to make them feel valuable because they have that they have natural intelligence. This is not just grades or memorization. This is actual intelligence in terms of curiosity, being able to articulate yourself, problem solving, wit, adaptability, communication, clarity and strategic thinking. How many kids hide their intelligence because being smart is treated as uncool socially? I would even say that you should encourage them to do these nerdy things. Actually, that will be my next point, But I want to drive this point home. So I want you to celebrate reading, celebrate habits that encourage natural intelligence. Learning, asking questions, intellectual hobbies, being articulate and being informed. [00:19:00] So I think children always will move toward what gets rewarded. And so if you reward them for reading, learning, asking questions, all of those things, I think that they will continue doing it. I remember when I was a kid, there was no Internet and my parents bought this expensive set of encyclopedia and this was the altar of our house. [00:19:24] Basically this was the thing. And my parents emphasized that they spent I think, two years paying off this set of encyclopedia. And I just remember to this encyclopedia set and thinking, oh my God, this is the best thing that ever happened to me. It was colored, it was glossy, it had all of this information and at the tip of my, you know, of my fingers. And it was so reachable, it was just there in our shelf. Whenever I was curious about something, I could just find it and learn about it. And my dad taught me that that is an absolute gift to be able to do that. And even when we had Internet, I always used like ass Jeeves because it was the encyclopedia, the Internet version of an encyclopedia. Right. And so because of that experience, this memory is still so vivid in my head. I learned that intelligence and learning about things is one of the best experiences that you can have in your life. [00:20:23] So my parents emphasized that. [00:20:26] They didn't ask who my friends were in school, as in, like, was I popular? They didn't emphasize about looks or being thin, and they did not ask about other things that are basically not important or that seem shallow. That's what I was trying to say. They always told me that intelligence will be rewarded, and intelligence is also attractive. [00:20:52] So don't be surprised when kids optimize for popularity in school, but always tell them that intelligence is a much more rewarding journey and encourage that. And so my next point will be I want to encourage parents to rebrand nerdy hobbits as elite training grounds. So I want to emphasize this because I think that this is such a strong point of my childhood. I had a lot of nerdy and uncool hobbies, like debate, being in the school paper, and, you know, participating in, like, speech competitions and math competitions and quiz bees. But I also realized that these are some of the activities that people mock in high school, like, you know, playing chess, being in theater, a cappella, Model un, coding, robotics, math competitions. Like, a lot of people call these kids as, like, nerdy, and they don't have a lot of friends. [00:21:56] And even, like, movies would depict these kids as, like, thin and lanky and pimply. And they're not, like, jocks or, you know, it's not a very desirable social life. And you know how kids are, especially teenagers, they do care about their social life. But I want you to remember as a parent that these things make for a lot of, like, advantages for how your kids will learn how to think. And in my opinion, that is what school is for. [00:22:25] I don't think that school is just there for kids to learn some stuff. I think they're there to learn how to learn and to learn how to think, and these activities are so worth it. [00:22:36] What do these activities actually teach? I think they teach persuasion, which is very important, very useful for life. Strategic thinking, confidence, how to perform properly, leadership, clear communication, and systems thinking. Actually, my training and debate is one of the best things that ever happened to me in college. [00:22:59] It was actually the highlight of my college life. And I was a competitive debater, and I won a major competition. And debate was such a great experience for me because I learned how to think fast. I learned how to look for what was wrong and what someone was saying. I learned how to cross Examine properly. I learned how to rebut. I learned how to analyze politics and pop culture and religion and socioeconomics and a lot of things. And it was such a good time for me to meet other equally nerdy, quote unquote people. But they are actually, they turn out to be super cool right now. Like, trust me, my peers in debate are now super cool people. They are top, top managers in huge behemoth multinational corporations. They travel a lot. They are actual millionaires. One person is in Forbes 30 under 30 and like, oh my God, my peers are so cool. I can only wish I could be half as cool as them. I'm just someone who yaps on social media. But yeah, they are so cool. And if I was a kid, I would be like, hey, I want to be like these people. And these people were debaters. They were the kids that other kids made fun of. So I know that cool kids or other, like, cool hobbies that we think are like super rewarded in high school, like, socially. [00:24:32] But it is the curious kids with compounding benefits in intelligence that really shine later in life. And so, yeah, remember those hobbies. And they're not nerdy. They're actually super cool. And these hobbies definitely pay off. [00:24:50] And so tip number five. I think that there's a moment when kids realize that money matters. Like my story earlier, I was in fourth grade when I realized that and I realized, hey, I need to start a business. And what, it's a business. Basically, you put $1 in and hopefully you take $2 out. And you have to do some work in between to make that happen. And there would be a time where a child would notice who has freedom, who is stressed, who gets to have options and who doesn't. And that kid will realize that these things are related to money or can be hugely influenced by who has money. This is a huge shaping moment. Instead of hiding financial realities completely, I would encourage parents to teach value creation, delayed gratification, leverage, ownership, negotiation, the value of saving, the value of investing. What is investment? What is an investment versus pure gambling? How can you earn clean money and the value of that? You want your kids to have a good relationship with money. Don't make them anxious about money. Don't tell them that, oh, money doesn't grow on trees. And you have to work hard and only work hard. And you don't do that because you're going to limit their beliefs and you're going to give them a ceiling that they don't deserve. They have to believe that they can break that ceiling and they can be the person in the family who can possibly change the future of the whole family. [00:26:24] Let me tell you, one of the most inspiring things that my husband has done is to be the first person in his family to go to college and finish college. And I'm, you know, when I learned that about him, when I first met him, when we were just getting to know each other, I thought that that was one of the most attractive things that was like about him because it showed grit, it showed perseverance. And when I learned about his hobbies, he used to be a competitive snowboarder. He was the president of the advertising committee or club in their college. I just thought, oh my God, it was so cute. It was so attract attractive. And the traits that he has right now, I'm probably biased because he's my husband, but I can't imagine him failing honestly. Like, I have a lot of trust in him and I have built a lot of safety and peace in my life because largely of the decisions that he has made for me and our little family. And once again, you know, it is what I also realized about my childhood, like looking back. [00:27:27] So the first time that you notice that your kid realizes the value of money, also remember that the earlier someone understands that money is tied to value creation, the more intentional they become. So that's really what you want to do. You want your child to be fully intentional about how they make money and what that means to them. So be open about this to them and have a positive and optimistic viewpoint about money. And don't try not to give them limiting beliefs. And if your parents didn't do that, realize that you can always do better and you can change the future of literally your generations if you do this. [00:28:06] So last point is build openness so you can actually guide them. So I might have told you to do this, do this, do that, make your kid do this, make your kid think that in my past five tips. But the most important thing is that you don't force them into this life that you had in your mind and that they don't build resentment. So entrepreneurial kids are or could become incredibly curious or incredibly independent, or they could be intense, emotional, secretive, highly experimental, and you have to nurture a relationship of openness with them so that you can be in that journey with them as an adult and you can guide them. So if your communication breaks down, then your guidance will not be possible. [00:28:52] So build openness, build honesty, reward for that, and create a home where honesty isn't punished. Immediately understand them and come with a approach of curiosity. If they approach their own entrepreneurial journey or their own money journey in the wrong way, like in your opinion, if they approach something in a wrong way, ask them questions and be curious about their journey. Tell them that emotions are definitely discussable, everything is figureoutable, curiosity is safe and mistakes can be admitted because eventually your child will struggle. Your child may be embarrassed about something, they may fail at something very likely, they may become insecure, they may compare themselves to others and maybe even feel lost. So if openness exists, then you could actually help them. Control creates secrecy, but safety creates honesty. So create an emotionally safe household and that openness in communication so that they know that you're there for them whether they fail or they succeed. Right? [00:30:03] So looking back, I realized that entrepreneurship didn't begin when I started making money, like when I was in fourth grade and doing my little snack business. It actually began when I was taught by my parents and when I was encouraged by my parents to think independently, to compete bravely, to give it my all, to create constantly, and to fully believe that my ideas had value. So the goal here is to learn that we're not here just to raise kids who will become entrepreneurs. Our goal is to raise kids who believe that they can shape their own lives. And I think that itself is one of the best, best gifts that we can give ourselves and we can give the generations to come. [00:30:51] So wow, I just felt like I gave a very Miss Universe ending to this podcast. So oh my God, this was so fun for me to record and it was really fun to celebrate my parents and of course Alex's parents in a certain way. To all the parents listening, feel free to reach out to me if you want to have a conversation about this. My heart is open and my inbox is open and having conversations like this remind me that there are unlimited ways to celebrate my parents lives. So reach out to me. You can find me on Instagram or LinkedIn. I will share the links in the show notes and if you want to chat about it, drop a comment in the comment section if you're on Spotify or Apple or slide in my DMs and let's chat. Also, don't forget to sign up for our newsletter so you can get the first dibs on our podcast promos and all of the amazing resources we have to live your ultimate Rich and Remote life. Thank you so much. This is Karla Singh Booth and I'll see you next Monday for another episode of Rich and Remote. Have a great week ahead. [00:32:03] Thanks for listening to Rich and remote, where freedom isn't a dream, it's a decision. [00:32:09] This is Carla, this is Alex Booth, and this is our journey to our dream rich and remote life. If this episode inspired you, share with a friend who's ready to live life differently, too. This is perfect for entrepreneurs who crave financial freedom, location freedom, and freedom from the opinions of others. And don't forget to leave a quick review. It helps more freedom seekers find this show. Big thanks to our sponsors, Huckleberry Consulting, getcsm and Proximity Outsourcing. [00:32:42] See you in the next episode and check out our online hangout spot, richandremote.com.

Other Episodes

Episode 8

March 09, 2026 00:37:37
Episode Cover

How to Build a Viral Personal Brand Without Losing Yourself

A lot of Founders don’t lose themselves in relationships or bad jobs. They lose themselves in their brand. The internet rewards exaggeration. Algorithms reward...

Listen

Episode 14

May 04, 2026 00:20:38
Episode Cover

5 Unconventional Sales Tactics that Got Us To $1M in One Year

When we rebuilt the business, we made one thing non-negotiable. We always had sales calls on the calendar. No fancy funnels. No ad spend....

Listen

Episode 16

May 18, 2026 01:01:50
Episode Cover

Scaling Agencies from 0 to $1M to Exit with John Doherty

Most agency founders think scaling means more clients, more hires, and more revenue. John Doherty thinks that mindset is exactly why so many agency...

Listen