Blog/The Jeff Heggie Show/Maddie Cawley - Division One Athlete to Entrepreneur

Maddie Cawley - Division One Athlete to Entrepreneur

Wednesday, December 21, 2022

The Jeff Heggie Show #32
Maddie Cawley
Division One Athlete to Entrepreneur 


Listen to the Full Interview on The Jeff Heggie Show HERE!

Maddie Cawley is a Division One college athlete turned entrepreneur. She is passionate about empowering today's young adults, the Gen Z entrepreneurs. When she went to college to play basketball, she went for a semester, ended up dropping out to lead her dream life and live life on her terms. And with a laptop and a dream, she launched her first e-commerce business, which she made six figures in the first year. And then in 2022, she co-founded the Young Entrepreneur School, and she hasn't looked back since. This is Maddie Cawley's story...

I'm Maddie Cawley, a college athlete turned entrepreneur. I'm passionate about empowering today's young adults, the Gen Z entrepreneurs. When I went to college to play basketball, I went for a semester, ended up dropping out to lead my dream life and live life on my terms. And with a laptop and a dream, I launched my first e commerce business, which I made six figures in the first year. In 2022, I co-founded the Young Entrepreneur School, and I haven't looked back since.

The biggest lessons I've learned as an entrepreneur are consistency is key, and don't get complacent. I've also learned that networking is key in this business.

The Young Entrepreneur School is a digital educational course where we teach high school kids, college.

In this episode, you will learn the following:

  • ​What it means to have a good mentor and someone to help you along the way.
  • ​How consistency is key when running a business.
  • ​What some of the biggest lessons are that Maddie has learned as a young entrepreneur.

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Podcast Show Transcript with Madison Cawley:

Hey, welcome to The Jeff Heggie Show, where you will develop a powerful mindset and unlock your full potential. Let’s do this. Hey. Welcome to the Jeff Heggie show. I’m excited today to have Maddie collie with me. She is a college athlete, a basketball player, turned on entrepreneur. She’s passionate about empowering today’s young adults, the gen z entrepreneurs. When she went to college to play basketball, she went for a semester, ended up dropping out to lead her dream life and live life on her terms. And with a laptop and a dream, she launched her first e commerce business, which she made six figures in the first year. And then in 2022, she co founded the Young Entrepreneur School, and she hasn’t looked back since. So I’m excited to have this conversation with Maddie. Share some more with us. Maddie, tell me a little bit more about yourself. Absolutely. Thank you so much, Jeff, for having me on here. It’s such a cool opportunity and I’m just super grateful. But yeah, anyway, so how I kind of got started, you kind of said it. I went to college for a semester. I played college ball. Did not love it. It just wasn’t for me. So I moved back home and kind of didn’t really know what I was doing. So I dropped out of college. I had originally majored in physical therapy. Wasn’t for me. And so I moved home. I was like, oh, I don’t really know what I’m going to do. I actually applied for a job at a golf course. Like, all right, I’m just going to do this for the summer. But yeah. So then my little sister’s birthday came up, and my mom was trying to find these yard signs like, happy birthday, congrats, happy anniversary, those kind of cool signs. But anyway, so she talked to a few companies. Neither they had terrible customer service or they were answering or the availability was like a few months in advance. So my mom was like, if someone were to do this well and they would crush it. And I was in the room and I said, you know what? What if we did it? And so we did it. Letter my landscape is what the company was called. It was born and that was our first company. And we ended up doing just over $160,000 in our first year. So it was awesome, super cool. It was a blessing. Fast forward, it’s been two years now. We started a few other ecommerce brands, and then a lot of our friends, family, parents are saying, how are you guys doing this? And how can we do the same? And so my sister and I talked about it. We were like, you know what? We want to create an educational course to help teach people exactly what we did so that they can get the same results. So the Young Entrepreneurs School was born, and it’s basically just a digital educational course where we teach high school kids, college kids how to start, run, and scale their own online businesses and make money online. Are you an entrepreneur who wants to discover the breakthrough secrets that will produce the results you’ve been searching for, but you just can’t seem to figure out why you keep working harder and harder and you’re just not getting those results? I want to tell you about a new challenge that I’ve created just for you the Business Domination Challenge. If you want to create the entrepreneurial lifestyle and the business you dream of, then this is exactly what you’re looking for. I created the Business Domination Challenge to show you how to grow your business exponentially and to become an optimal performing entrepreneur. What’s an optimal performing entrepreneur? It’s an entrepreneur who’s succeeding in all areas of their life. If I show you how to build a successful business, but your relationships, your health, and everything else is falling apart, that’s not a success. It’s not about working harder. It’s about implementing the correct principles and becoming the person who can do the things that produce the results. Hurry and go to and secure your spot today. That’s awesome. And I love that you followed it up with the school because it’s really easy to say, oh, yeah, Maddie just got lucky. She got lucky with getting in the right time or something like that. And she said, well, there’s obviously some things that you did right, and so that’s really cool that you’re able to take that experience and pass it on and help others to be able to get on that route. Absolutely. And funny enough, we’re actually selling a few of our ecommerce stores because I’ve discovered that this is what I’m passionate about. I’ve done it, and I’m still doing it, but I want to help people and serve others and show them the opportunities that lie with an entrepreneurship and show them that they can do it. It’s possible for them, as well. And so it’s been a blast. It’s been a great journey. So it’s been two months since we launched, but it’s been fun. That’s very cool. So with that first business, assigned business, what were some of the biggest lessons you learned right out the gate? Absolutely. Yeah. So consistency is key. So, obviously, our first month, we did over $11,000, I believe, and I was just like, okay, my goal was maybe $502,000. It was just kind of like a little side hustle, right? But it was a business in a month. And so, honestly, over that course of a year or two years, now, consistency is key, and so don’t get complacent. And, okay, this is awesome, so ride that way, but keep trying to get better and grow the business rather than getting complacent and still and just kind of letting it go in the background, because it will bite you in the butt if you do that. Now, one of the good things and it’s really cool about having the entrepreneur school is having some mentors, having some guidance now? Absolutely. I don’t know your dad, but I know your mom, and you’re fortunate to have a great mentor there. Share a little bit about that, what it means to have a good mentor and someone to help you along the way. It’s so important and it’s honestly the only way, I think, that you can really become successful because you need someone to push you to be your best at all times. Like you said, I was born in an entrepreneurial home. My mom’s, serial entrepreneur. She’s amazing. Has a few six, seven figure companies. She’s crushing it. My dad is a retired sportscaster and now he helps her with her businesses. But yeah, so it’s the greatest blessing, especially living in a home with an entrepreneur. It’s amazing. But see, I realized that opportunity that I have and that not many kids get that opportunity. And so that’s kind of, again, another reason why we started the Young Entrepreneur School, because I was blessed with the opportunity to be raised in an entrepreneurial home and in that environment. But not many kids get that opportunity, unfortunately. So we want to help kids that are in that environment and show them what’s possible. What are some of the things that you talk to them about? If you’ve got a kid that’s not in an environment like that and they don’t have resources that they can do a big investment, but they want to get started, what are some of the things that you tell them? Absolutely. So what we’re trying to do at the Young Entrepreneur School is build that community. That’s what I kind of thought was missing in our society today. Well, overall, it’s just kids believing that there’s these opportunities out there, but this community of high school, college kids, young adults who are trying to find this entrepreneurial community, it’s just not out there or it’s super hard to find. And so that’s kind of one of our main things, is, yes, you’re getting our course, yes, you’re getting all of our resources and all that stuff. But networking is key in this business. Again, we networked at this event, and now I’m on your podcast, like, the coolest thing ever. And so networking with other like minded people will help you grow whatever you want to do in life. Honestly, it just enhances your life and it’s the greatest thing. Networking is one of the key things when it comes to in life and when it comes to running a business. So that’s probably the main thing. That’s one of our main selling points is, like, you’re going to have access to these other, likeminded, entrepreneurs who are going to push you to be your best and keep you accountable. Let’s go a little deeper into that. I didn’t intend to get into this so quick, but you got me curious on some of these things. I want you just to share more about the school and how it works so they have the opportunity to get into the course. And obviously, like, you talk there’s some networking opportunity, but to share more about this course, because where you and I met, it was a really cool situation because it was an event full of young entrepreneurs, and it was inspiring to see that. So are you creating that environment for these others? Absolutely, yes. So we have tons of different platforms that we’re trying to communicate on. I’m trying to learn discord. Apparently, that’s like, the big thing with kids nowadays. So I’m trying to learn that because, again, that’s what kids are familiar with. But yeah, so we have multiple channels of communication. We have weekly Q and A calls where we keep them accountable. We answer your questions pretty soon here, we’re going to launch accountability coaching, because I know that’s so huge, one on one coaching. So we’re going to launch that within our program. But yeah. So young entrepreneur school, basically, digital educational course. We have multiple paths to wealth. So right now we have two, where it’s either ecommerce or expert. Ecommerce, you learn how to sell physical products, expert, you learn how to sell digital products. But eventually, my big goal is to scale this to the moon, have tons of members come in and have multiple paths to wealth. So whether that be real estate, airbnb sales, marketing, anything, we want to let kids choose what path will suits them or interest in the most and learn how to make money with it. That’s awesome. That’s one that I’m having a hard time getting my head wrapped around. I’ve got a group that uses it, and I’m not a big fan yet. Right now, we have a Facebook group, and then obviously they have my email and all that, my phone number and all that stuff. But I literally texted all my guy friends today, like, hey, teach me discord, because I have no clue what I’m doing. That’s what I’m trying to learn at the moment. But I know it’ll be a powerful tool once I use it to its full potential. Right. Awesome. There’s a few directions I want to go in our conversation. Sure. So let’s take a little bit of a step back. Okay. You’re an athlete. You want to play division one basketball. And one of the things I’ve got a program called the Confident Athlete Program. I work with a lot of athletes. I’ve coached for 20 years. One of the things I’m always talking to athletes about is there’s so much you learn as an athlete through discipline, hard work, all of those things that are far beyond sport, they’re going to help you throughout your life. In the Confident Athlete Program, the things we teach, we’re focused on their sport, but if you took the sport out of it, they’re the same things I would teach them for life lessons. Tell me some of the things you’ve learned and acquired as an athlete growing up that has helped you today as an entrepreneur? Absolutely. I’d say there’s three main things. I was a very shy and introverted kid growing up in high school. I’m still kind of integrated, but I would say basketball. My sophomore, junior, senior year really brought out some leadership qualities, kind of pushed me into uncomfortable situations. But I grew through those situations, and I kind of built some leadership qualities out of that. So I think that’s one of the main things. It built my mental toughness. And so, again, I was a shy kid, middle school, early high school, my mental toughness, I was pretty weak mentally, to be honest. But it really built my mental toughness, having a tough coach, but I would have run through a wall for that coach. Your coaches really have a huge impact on your life, and I applaud coaches, and I’m so grateful for the coaches I had. But I would say mental toughness is another one. And then learning that it’s okay to fail because there’s so many things nowadays where it’s like, oh, I don’t know, like you can’t lose games or yes, ultimate goal is to win a championship game or whatever, but I would say it’s okay to fail. It’s another main thing I learned, because without those failures, you wouldn’t be where you are today. And so, like, my sophomore year, we got upset in the playoffs, and I was like, oh, my gosh, it was the end of the world right at that time in high school. But had that not happened, we would have gone on to winning state my junior year. It was basically the fuel to push us to be great and helped us grow. So I would say those three things leadership, mental toughness, and it’s okay to fail. Use the failures as learn from those failures and use the failures as stepping stones rather than anchors that weigh you down. That’s awesome. Every single one of those is such a powerful life lesson, and especially as an entrepreneur, that is going to be very valuable. So let’s talk more and more about that third one. Sure. So far in your young entrepreneurial life, what do you feel has been your biggest failure and how did you cope with it and what have you learned from it? Absolutely. Oh, man. Well, one of our ecommerce stores that we tried to launch, what was it, six months ago, totally flopped. We have a couple of successful ones, but this when we started, we did all the same things that we’ve done with our other stores, and I got comfortable and it just totally flopped. So it’s been two years now in my entrepreneurial journey. But that and then also, like I said earlier, getting comfortable. So you get to this point where, okay, I’m making a couple of grand a month or however much it is, and then you get comfortable and you stop putting in the work. And so I think that’s one of the main things that a lot of kids may get stuck with, or even adults, even adult entrepreneurs to get comfortable and then it can come back and hurt them in the end. So I would say that was the main thing, having that failed business. But with that being said, I’m glad it happened because had it not, I wouldn’t have learned from that situation and grown a couple of other businesses and now the young entrepreneur school. Awesome. Yeah. I mean, none of us want to go through failure, none of us enjoy it, but it is some of the most valuable lessons we can learn, for sure. It’s needed. I think it’s needed. Failure is needed. Yes, absolutely. Yeah. So going with what you’re saying, what do you do? What are some of your success habits or whatever you want to call them that help you from being complacent, to help you from getting too comfortable? Sure. So honestly, again, it’s a big blessing. But having my mom to constantly encourage me, keep me accountable and stuff, like in the mornings, I journal every morning, kind of debrief everything that went off the previous day, kind of see where I need to go, write my daily goals, and then I have my monthly goals. I have daily affirmations that I will be my goal is to be a millionaire by 23. So I will be a millionaire by 23. I will impact thousands upon thousands of people. I’m good at what I do and what I offer transforms lives. Like, those are just a few of the things I tell myself every day. Because one of the main things I like to preach is you want to train and sustain a positive mindset because your mindset is half the battle. If you can grow and train and sustain that positive mind, I promise you it’s going to be a lot easier than telling yourself, oh, I can’t do this. Oh, this is terrible, it’s never going to work. But what if it does? You want to try to flip it around and see and just develop that positive mind. So that’s one of the main things that I work on on a daily basis. And yeah, just setting goals is so important nowadays and I feel like a lot of kids just kind of coast through life or have this idea of, oh, I’m just going to follow the crowd. It’s because it’s what’s comfortable. And so anyone, kids, adults, people don’t like feeling uncomfortable, but in those situations, that’s when we grow. And so I’ve come to realize that and I’m constantly trying to find new things to push myself out of that comfort zone. And yes, I read some books, I listen to podcasts, just constantly trying to develop my mind and learn new skills that are going to help me generate and build wealth. That’s great. That was actually going to be one of my next questions on the whole self education side. I’ve already mentioned that, that you read, that you listen to podcasts and stuff. Sure. What has been the most impactful or influential book that you’ve read? I mean, your mom being a publisher, I guess you’ve got access to, oh my gosh, our Office right now and all of these. But she has two huge bookshelves. But anyway, I would say one of the main ones, it’s a classic and everyone has probably heard of it. But to get started, I would say Rich Dabboard, just because you see the different sides of it and it’s a total mindset shift. That was one of the main ones winning. The Word in Your Mind by Craig Groschel Groschel, he’s a pastor. I always say his last name wrong. But that’s a really cool one as well because I’m a huge Christian faith, total faith based stuff. And so it wraps in spirituality with having a positive mindset and brings Jesus into it. So it’s a great buck as well. But I would say those two obviously bank and grow. Rich is another one. But yeah, so those are probably three of my top bucks. That’s really cool. So looking at these younger entrepreneurs that you work with, right? If we’ve got someone that is just listening right now, obviously we’re going to share how to get hold of you, how to stay in touch, all those things. But someone that is an aspiring entrepreneur, they’re young. What are some of the things besides going into the school? What are some of the advice that you would share with them? Absolutely, I would say be open to advice. It’s okay. It’s okay to listen, to have mentors and to be curious and to take risks and stuff. So another thing would be it’s okay to fail again, like I said earlier, use failure as learn from failure and then use that failure as stepping stones rather than the anchor. So what I mean by that is grow from those situations and take those situations and obviously learn from them. So grow from those situations and kind of twist my words here anyway. But yeah, so use failure as a stepping stone rather than an anchor. And then another one I would say would be here, mindset is everything. And so that was one of the main things for me was like surrounding yourself with people who are super negative all the time is not going to help you achieve your end goal or where you want to be in life. And so that was kind of hard for me because I had some really great friends from high school. But they just have super negative mindsets and they’re complacent in life. And so you want to surround yourself with super positive people who are going to push you to be your best and keep you accountable and realize your goals and realize what your goals are and accept that and say, you know what? You can do this, you can achieve that, rather than saying, that’s a stupid goal, that’s a dumb goal, that’s never going to happen. So just surround yourself with people who believe in you and push you to be your best and keep you accountable, who are like minded. That is some great advice and I really appreciate you sharing that because I think a lot of that thing, those naysayers, those small minded people and all that, there’s always going to be the sideline critics, the armchair athletes, those sort of things that they know better than you, that they think you’re crazy, whatever it is. Right. But if you let them keep you out of the game, you’re just setting yourself up for failure. Absolutely. You’re letting them hold you back. You have control over your own future and over your own destiny. Don’t let their thoughts hold you back and honestly not let you reach your full potential and do what you want to do and achieve your dream life. Right. And now we’ve talked about the importance of learning from failures and all of those things. What about what are some of the things you learned from some of your successes? I would say some of the things I’ve learned from my success is oh man, that’s a good question. I’ve seen what’s possible now. So once we’ve done really well over the last few years and now I really know it’s possible. And again, I surrounded myself with like minded entrepreneurs and it’s pretty cool to see them I mean, their goal. My mom for one of our goals, I said, okay, I want to have 150 members when the young entrepreneurs go by December. But my mom was like, why not have like 500 to 1000? And so that’s like one of the cool things that I’ve kind of seen and grown from. When you really do surround yourself with the right people, they open your mind to so much more opportunity. And then another thing I’ve learned is just how much opportunity there is out there, especially with the online world and social media and stuff. I mean, social media is so powerful. Yes, it can be awful at times. There are some terrible people on social media and people can use it as a sword rather than a helpful tool. But I think social media is an amazing tool, especially when you’re starting out in business. And it’s what we’ve used to just grow without even having to really spend money on paid ads and all this stuff. So it’s a powerful tool where you can reach a lot of people. And people are funny because people are looking for help. They may not seem like it, but they really are. So I think that’s one of the main things that I’ve learned is it’s okay to put yourself out there and to take that jump and take that risk. Because again, my sister was a social media person. I never put my face on the screen. I had like an Instagram and stuff, but I rarely posted. But now I’m hosting a few times a day. But it’s been awesome. I mean, doors have been open and opportunities have come and it’s a huge blessing. So once you take that risk, you’ll see the rewards start coming your way. So now that you’ve exposed yourself like that and you’re becoming that charismatic character and the face of the company and stuff, what has your experience been dealing with the trolls and the haters and those sort of things? Yeah. How do you deal with that? Funny enough, I posted a video today and it’s already gotten a few negatives. Like there’s people that go on and say, oh yeah, I’m going to keep scrolling, whatever, it’s going to happen. I mean, when it first started happening, I was like, oh gosh, that kind of hurt. Like that was not very nice. But honestly, I see it as kind of funny and not even yes, funny to some point with some people, but honestly, I kind of feel bad because these people have developed this feeling of like, oh, it could never happen for me. And then they come on saying stuff like, oh, this is stupid, this is dumb, it would never work. But they aren’t even open to the belief that it could happen for them. And so I just see it as I mean, now I don’t even respond. I may respond to a few of them just be funny and just kind of be like, okay dude, but honestly, you just use that. You don’t even acknowledge it. You focus on the people that are willing to listen to you and serve them the best way that you can. I think you said that really well because I was actually talking with someone about it yesterday that was dealing with it, getting some negativity and stuff. And I said feel sorry for them that they have a desire to waste their time and energy to try making you feel bad. Right. And they’re obviously not your target market, so move on. Exactly. But it’s still hard. I mean, even on my podcast and stuff, I get a thumbs down or something. I’m like, what the heck? Move on. Seriously. Well, share with us. I mean, I love what you’ve been doing and I love your mindset and your enthusiasm, passion, all those things. And with the network you have around you and everything, your future is so bright and I’m so excited for you and I love that you’re passing that on to others and tell us what your big vision is. What are you going to do? Yeah, so I want to build a family empire. I want to have multiple. I mean, I want to scale young entrepreneurs, go to the boon, have thousands of members, be able to help and serve thousands of people. And again, just help them realize the opportunity and help them develop this belief that, okay, maybe it can happen for me, and then obviously help them build successful businesses at the end of the day. But I want to scale that. Build this multi million dollar empire with my family. I’m a huge family girl, so, like, bring my mom in, dad work together. But yeah, and then that’s basically it. It’s the big goal. But we want to scale quick. I mean, we launched two months ago, and we’re ready again, like I said, by December, we want to have 500 members in and keep impacting people and showing them what’s possible. Well, you’re doing some amazing work, and I love what you’re doing. So share with our audience where people can find you, where they can find the young entrepreneur school, all those things. Sure. Yeah, absolutely. So on Instagram, we have just young entrepreneur school. And then my personal is Maddie, M-A-D-D-I-E cally, C-A-W-L-E-Y. I’m on Facebook. I’m on YouTube now with the young entrepreneur school. I never would have thought I had a YouTube channel, but now I do. But, yeah, that’s just a few of the places you can find me. All right. And I’ll make sure that we have all the links and everything in the show notes so that people can just quickly find you there. Awesome. But I’m grateful for the opportunity to meet you and your mom when we did. Absolutely. Because I’m excited to watch your journey because you’re doing some great things, and I’m really excited about that. So thank you. Thank you for joining me here. Of course. Good luck with everything you’re doing. It’s going to be awesome. Awesome. Thank you again, Jeff. I really appreciate it. Why do some people succeed at levels beyond their imagination while others struggle? The mind is the key to your success. Even the best strategies won’t matter without the right mindset to implement. It. For those who desire to be great, to do amazing things and have an impact on the world, the Bigger Future coaching program is designed to take your life and your business to another level. If you’re ready to make big commitments, be held accountable, and develop the success mindset that’ll take you beyond your wildest dreams, join us today. Go to to find out more. Athletes put a ton of time and effort into the physical aspect of the sport. It’s something they have to do to be great. But one thing that’s often neglected is the mental game. And the mental game, it’s just as important as the physical. And that’s why I developed the confident athlete program. In the confident athlete program, I work with athletes at all levels, and we work to develop their confidence, their mindset, and really tap into their potential. So if you want to really take your game to the next level, you want to develop to your full. Potential. Check it out at

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Jeff Heggie

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