17 Year Old Investor With Jack Rosenthal

Episode 349: 17 Year Old Investor With Jack Rosenthal

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REIS 349 | Young Investor


Not everyone is born to be entrepreneurs, but those who are, start their entrepreneurial wonders the moment they learn how to speak. Here to amaze us with his business success is young investor Jack Rosenthal. Mitch Stephen interviews this seventeen-year-old powerhouse who is the founder of Young Investors Club, LLC and author of The Ultimate Guide to Teenage Investing. Jack is still in high school, and he will already teach us how we too, regardless of how old we are, can ignite our passion towards earning and succeeding in life. He also shows us how he manages his time between school and running his business.

I’m here with Jack Rosenthal. This guy is special and unique. It’s my pleasure and my honor, to have him on this podcast because this guy is seventeen years old and he started business at the age of six. He’s out of Armonk, New York, which is in Westchester County. I’m going to let him tell you how he started. It’s an amazing interview. I wanted to interview this guy for a while. We can only do it at this time because he’s still in school and has some things that we can’t work around. I decided I would fit into his schedule. I’m happy to be at this time that he could do it at my ranch down in South Texas. Jack, how are you doing?

I’m great. Thanks for having me on. I’m glad that we were able to make this work. I’m sorry, we weren’t able to do it earlier in the day. I have school and it would’ve been a little more difficult to conduct this interview from school, but I’m glad we were able to make it work anyway.

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I’ve been an entrepreneur all my life. I started selling things online at the age of six years old. That’s when I put up my first website, CoolPaperPlanes.com. You could still check it out. The website has 60,000 hits as of now because we were able to get the domain name, Cool Paper Planes, which back then was it much easier to get. Nowadays, there’s still a lot of traffic that comes to that website. At the age of eight years old, I started doing peer-to-peer loans on sites like Prosper and Lending Club. The way that this worked and I’m sure a lot of the real estate investors out there could appreciate this maybe if they want to do with their children. My dad lent me $1,000 that I had to pay him back at a 1% interest rate like he was getting in the bank. It was no different from whether he lend me the money or the money he was staying in the bank.

I would go re-lend out these loans on sites like Prosper and Lending Club, which is where you could do group funding of loans. When someone wanted to borrow $25,000 to remodel their kitchen or whatever the case may be, I would make a $25 loan to that person and alongside with a thousand other people, we would all make that $25 loan to that person times a thousand and then that would fund a $25,000 loan and that we were paying let’s say an 8% to 9% interest rate on something like that. As an eight-year-old investor at the time, I was able to keep that spread. It worked successfully with $1,000. We did it again with $5,000, maybe even more spread. That was my first introduction into lending money.

At the age of thirteen years old, I started what is now considered the largest key investment group in the country or one of the largest, there’s no exact list, so I always call it the largest. I started the club my freshman year of high school. I started recruiting basically a whole bunch of kids from at first a local area and then we started expanding to the East Coast. The idea behind the club was, “Instead of me investing my $1,000 in the stock market on my own, wouldn’t it be so much better if I could invest that $1,000 alongside ten other kids? We could all learn from each other, learn from each other’s investments and talk about stock market investing together. We also grouped together all our money in one portfolio.” In the first year, we had twenty members and around $20,000 and the investment account. Fast forward a couple more years after a lot of recruiting, a lot of expansion all across the East Coast, we have close to 100 members in over $115,000 under management in our portfolio for the Young Investors Club, LLC. That’s what I did freshman year up until a senior year.

How did it work out for you? Were you able to make money through that?

The way that worked it wasn’t so much of a business venture, it was more of like running an organization. I wasn’t so much given a financial reward from running that. I was more given 100 other connections with other teenagers that all wanted to invest in the stock market. I was given a lot of credibility because I was able to put together such a large group and with such a large amount of money for teenagers, which is to my knowledge, never been done before. One, it gave me authority and two, it also gave me a lot of other connections with teenagers who will one day hopefully become future business partners. It gets to the point, do you want to know about the money? Do you want to know about the rewards? Why did I start making money?

I was 50% expecting you to say it was to get a following or something other than money.

The more you collaborate with others, the bigger your audiences grow. Click To Tweet

It was because the truth is, running one of these investment clubs. Even if I tried to monetize it, there wouldn’t be a lot of money there in the first place. You could try and take a management fee, but ultimately I feel like that degraded the integrity of the group. I would have wanted to be in this like everyone else and make it an equal.

Teenagers don’t have a ton of money.

That’s not where you make the money. You don’t make the money off managing other teenagers’ money.

I didn’t want to make money when I started my show. I ended up making money from it because you see the opportunities and then you take advantage of them. That’s where you were leading to.

Finally, the money part. I had realized that although these things that I’ve achieved up until this point or impressive, I hadn’t been financially rewarded for some of my business comps. Other ones, I had been but not the levels that I desired to. Although other teenagers weren’t being rewarded financially at the time, they were more focused on school. I was always interested in, “How can I go out there and make money?” At the end of my junior year, after I’d finished all my major exams for the year, the SAT, the big important test to take for college, junior grades are important grades that colleges look at. At the end of that year, after I was finishing up what was the end of my school career and what was going to determine what colleges I got into. After I was done with that, I said, “It’s time for me to focus on business and come up with a vehicle and then execute on that vehicle of a way in which I can produce income for myself.” I started a social media marketing agency. I had tried to start a similar one of these around a year or so before with a partner. I’m not sure if you’ve ever had any experience with partners. However, my experience didn’t turn out to be very positive. It was me and a good friend of mine.

That was your first problem. 

Don’t go into business with friends, which is something, believe it or not, my dad told me and I did not listen to him just like many kids out there.

I’m not saying you can’t go to business with your friends, but you need to pick a partner because of their acumen, because of their experience. Let’s take it a different direction. If you’re great at finding deals but you don’t have money, then your partner should probably be a guy who has a lot of money or has access to money because you need a different piece of the puzzle than what you have.

That was the biggest thing. The piece of the puzzle of it providing was that we weren’t exactly so different. We were the same piece of the puzzle. We didn’t provide the same amount of value and we’d have to split it down to half, which ultimately made it an unsuccessful partnership. It’s hard to be friends and then you don’t know when your friends and when your partners and it was always running and you never had time to take a break. For numerous reasons, the business ended up failing because of the partnership and not because the business was such a bad idea. A year later, I decided to try the business again, however this time, do it completely on my own. I manage everything on my own, get clients on my own, maintain the business on my own and do everything by myself.

REIS 349 | Young Investor

Young Investor: Don’t go into business with friends.


That’s where I started to see success. At the end of eleventh-grade, I went out to go pitch clients. Let me get into what exactly is social media marketing and what I was pitching. I’m not sure if you’re aware, but there’s been a whole new industry that’s emerged of social media marketing as opposed to traditional marketing. Digital marketing has been around for a little while, but social media is even more recent than that. There are a lot of other young entrepreneurs out there not much older than me that are looking to help and show businesses how they can use social media to ultimately generate more business and gain more attention on these platforms.

I looked at that and I said, “I think that’s something I could do.” I’ve been on social media all my life. I understand it. I understand it way better than a 50-year-old business owner who’s never been on social media day in their life. I said, “Let me go ahead and give this a try.” My first client that I got on my own was a restaurant. I pitched the restaurant, I said, “You pay me whatever in a way. It’s anywhere from $500 to $1,500 a month. You pay me that much and I’m going to manage your social media pages.” The first one I started managing it on my own and then I started getting a couple more and then I started building out a team to help me manage these pages.

I had to hire a photographer to go in and take pictures of these different restaurants of the different food being made. Then I’d have my content designer execute all the content across the various social media platforms. I and the business owner would manage all the business, keep everything together, get new clients and make sure that all the gears are working. I’ve been doing that up until May or so. Up until now, I’ve been running that business and it’s been going quite successfully. This is the first serious monetary success that I’ve had in the business world. As I said, I’ve been an entrepreneur all my life, but this has been the first thing that has been straight in money form.

I have a question for you and I’m not trying to steer you one way or the other. I’m just asking a question. Why aren’t you going to college?

It’s a good question. You’re not the first person that asked me or the second person after that question.

I should have rephrased it but here’s the thing. I don’t believe college is for everybody and there’s a whole lot that is not for it. Whether you go to college or not, this is an encouragement to people who either are never going to be able to afford to, don’t want to or they’re not cut out for it. I wasn’t cut out for it. I didn’t go to college. I like to tell everyone I went to La Calle U that Spanish for the street. I was educated by the street. I got a doctorate from the school of hard knocks or the street. What are your thoughts still?

My thoughts about college, pretty much one, if it would have been a financial burden, it would have been a different situation for sure. I come from a family which my parents can afford to pay for college for me, which I know is not like most. Maybe perhaps if I had been in a situation where my parents couldn’t afford to pay for my college, I would say that the cost of going to college would be way too high or that I’d be responsible for the cost. It would be way too high a cost to incur. The second reason why I’m going to college is that for many people who do okay in school, I don’t know exactly how much it makes sense to do okay in school and go to an okay college and then get an okay job. I don’t know if the cost of giving up those four years of your life plus the cost of college, all of that is worth getting like an okay job at the end of it.

However, I’m not an average student. I’m not ashamed to admit it. I’m a good student. With the same disciplines that I’m able to take to the business world, I was also able to take it to the school world. Although you’re not nearly as passionate about sending for a history test, if you have the willpower to do it and if you get a good grade on this test, it can incorrect you grade for the trimester and that’s going to impact your grade for the year. You’ve got to do that times five classes and that’ll impact what college you end up too. If you’re able to use that to go to a good college, it can be rewarding in the end. I’m in complete agreement with you.

I do not think that most Americans should go to college. In fact, I was talking to my dad, “What would the ideal education world look like?” We both agreed that four years is way too long. The cost of it is way too high. They come out of college with $200,000 in debt. That’s four years of their business life that they could have spent in the business world. They’ve given up. The opportunity cost is high. Let’s say that we are at $50,000 a year at that job. They haven’t given up $200,000. They give out $400,000 and all the stuff that they would have learned because let’s face it, 90% of the time you learn everything on the job. You don’t learn the skills and acumens that you need to succeed in most businesses in college.

You got to do ten times or 100 times more action than you think is required in order to actually end up with those end results. Click To Tweet

Not only you missed out on the education, you missed out on the opportunity cost of earning your job and not only that, but you paid money to go there. For all three of those reasons, I don’t think it makes sense for the vast majority of Americans and the future idealistic world. I’d like to see one-year college training programs or less, where you choose what specific business you want to go into, whether it be real estate, finance, being a doctor, being a lawyer or whatever the case would be. Go there for one year. You must learn all the material that they spread out over four years, but you could all learn in one year and then you go into the business world at the age of twenty. That’s what I think that the world should evolve to. We’re heading to a point that I see much fewer graduation rates in graduate school. You see a lot of talks now online if entrepreneurs should go to college. I hope that because of how inefficient the system is, it’ll evolve into a system like that one day.

I haven’t known very long Jack, but I said whichever path you take, I’m sure you’ll find some great advantages to it. I was curious about what your thoughts were. Does your family want you to go to college? Are they leaving it to you?

No, they want me to go. There is no doubt.

If I look back, if I had gone to college, I would have studied finance and how to read spreadsheets and how to set up a business. That’s one of the hardest things for them to do is learn how to keep track of their business and keep in good standing and have financial so that when it’s time to get bank loans and stuff, you’re in order in such that you can get those great, fantastic loans and stuff. If you’re out of order, you can’t. Are you primarily working on the social media marketing company?

I have a couple of things I’m working on. One, I still run the group, however, we’re transitioning that. The group was meant for high school students. I’m a senior so next year I’m going to college. I’ll no longer be a high school student next year. I’m transitioning to have someone else manage the club. As of now, I still manage the club. I also maintain my stock portfolio. All the money that I’ve earned over the years. I invest in the stock market and that doesn’t take my daily attention, but I’d still invest it. My main daily attentions meant my social media marketing agency. I always have fires and tons of people I’m dealing with putting out stuff, calling people during school. During my one-hour break at school, I’m sitting there, working on my business. I was thinking like, “It’s tough running a business while going to school.”

Do your friends think you’re nuts or are you an outcast? 

Ever since I’ve been young, they’ve always known me as a business kid. I was always the kid out there hustling. Back in ninth grade, I was selling fidget spinners, putting together websites and selling things online. Ask any one of my old friends, they’ll always tell you, “Jack’s been an entrepreneur from day one.” They’ve accepted it at this point. There’s no doubt it’s been challenging going to school and being an entrepreneur. Fortunately, I will outlive that problem quickly. As of the moment, it’s a lot to manage between going to school, sending emails right before and in between classes, making calls in between classes, getting everything all scheduled and figured out.

That’s the third thing. Finally, I started a YouTube channel, which I’m excited about, like your podcast. You took it out. It’s a passion project. It’s a similar thing to me. Whenever you’re starting something new, it’s fun. I would say that’s the best way I’d describe it. You get to experiment. You get to learn. I’ve already learned so much about YouTube in the last two months than I knew before. I’m up to 93 subscribers on YouTube and that’s as of a month and a half starting the channel. I’m pretty happy about that.

Putting out YouTube videos, putting out free content for basically other teenagers to try and impact other teenagers and young adults. It’s been so rewarding. I get comments on the videos like, “Jack, I’m another eighteen-year-old teenager out there. I got selling too. I live in New York too. I love what you’re doing. I’m also passionate and interested in all those things.” They’ve sent me emails. It’s cool to connect with all these people online that I wouldn’t otherwise get to connect with in a world twenty years before without YouTube.

REIS 349 | Young Investor

Young Investor: 90% of the time you learn everything on the job. You don’t learn the skills and acumens that you need to succeed in most businesses in college.


What college do you go into?

I’m going to go to a college called Babson. Not sure if you’re familiar with that. Babson is the number one entrepreneurship college. Somehow, there are rankings for entrepreneurship colleges and perhaps, it has a strong program in entrepreneurship. You could see why I picked that one. That’s the college that I’m going to next year.

That makes more sense to me, but I’m not up on colleges. Have you ever thought about doing social media marketing for a company for a piece of it?

Do you mean getting an equity share?


I have thought about those things. It was offered to me once. I would consider it.

You might be getting another offer sometimes I predict. What’s your advice to young entrepreneurs out there?

I get asked this question on every single show or whatever the case I may be on. One thing, I’m very transparent about my strategies. For example, why am I in this show? Some people may be wondering. As much as I love me and you, it was great to talk to you and everything on this. I’m sure why do you do podcasts and have you ever been on podcasts with other people? Probably all the time. Why am I doing this episode? It’s because I know that to grow my YouTube channel or grow my social media presence, you’ve got to collaborate with others. The more people I can collaborate with, the bigger my audiences grow. It also brings content to other people’s audiences. A lot of times, you don’t get to hear from a seventeen-year-old entrepreneur to be a unique perspective to hear from. There is no doubt. That’s the reason I’m on your show.

It’s like a little piece of wisdom out there for any entrepreneur that wants to start a following of any kind on Instagram, YouTube or whatever the case may be, you should collaborate with as many people as possible. Maybe you think this way as well and you have to think this way to take on as many houses as you get. You said you’ve you owned indirectly or directly 1,000 plus houses. That means you’re thinking at a different level than most people. You may not be aware of it or other people don’t understand exactly the level that you’re thinking about, but to take on 1,000 houses, that means you’ve probably made 20,000 offers.

Most people that are entrepreneurs were born to be entrepreneurs. Click To Tweet

You’ve probably sent over 100,000 emails. You made thousands and thousands of phone calls and other people they don’t understand exactly what goes into taking on and creating that much in business. Whatever results they see, there’s ten times that much of action that was put out into the world. I’m sure you remember it back then, but I’m sure a lot of the audience isn’t familiar with how much effort it takes. To give you an idea, go back to the interviews, why am I on this show or how did I get in this show? I’ll tell you how. I had one of my VAs, my virtual assistant. I said, “Make a list of the top 1,000 financial YouTube channels that I can collaborate with and we’ll send emails to all of them.” That’s exactly what we did. Other people would say, “I’m going to message ten guys, I’m going to go research, find ten guys that I want a message to and I’m going to try and reach out to those people and see what happens.”

If you do that, you might be lucky to get one or maybe you’ll get nothing, however entrepreneurs are thinking about bigger levels. They think, “Why would you go for ten if you could go for 1,000?” I can’t sit there and do all the manual labor of typing out emails and everything, but I can pay someone else up. I’m fortunate enough where I have a business that I can afford to outsource stuff to other people. That would be my first tip. You got to think at a different level. Whether you’re trying to pick up social media marketing clients, whether you’re trying to pick up real estate investment properties and you’re trying to make wholesale deals however much you want to get out of it, you’ve got to do 10 times or 100 times more action than you think is required in order to end up with those end results. It’s an easy concept to understand, but few people execute it. That’d be my biggest advice to any entrepreneurs out there if they want to get successful young or late age.

I was told I was going to interview a sixteen-year-old. You got old on me. You turned seventeen. I had my preconception of like, “Who was I going to be talking to?” I knew that you’d be exceptional or different, but I had no idea that you would be at the level that you’re at. If you don’t mind me saying, you’re impressive if you ask me. When I was not even six, when I was 21, I had my head so far up. I shudder to think. Did you come up with this stuff on your own or do you come from an entrepreneurial family that helped guide you in this direction? My family was not entrepreneurial. We didn’t talk about business at the table. They might not even have been on any business to talk about. I’m curious, are you spawning this or did someone help spawn this?

99 out of 100 kids, if they’re born to the same family, the same conditions, they would not become entrepreneurs like me. I have a little brother. He’s interested in playing football. All he wants to do is play him as much football as possible. You couldn’t give less about entrepreneurship than any other kid out there. I would not say it was so unique to my family. It happens that my dad did start his own business as a financial company, but financial is a little difficult of a concept for a kid to understand. You can’t exactly go visit a factory or anything in finance. It’s starting your own finance business and working in a finance company or not so far. They’re more closely related than other businesses.

Whereas working in a shoe factory and owning a shoe factory, there’s a huge difference between the employee and the business owner. Working in finance and owning a finance business, there’s not as much of a difference. That’s why I say it’s not so related to my background. I was fortunate that as a person and my dad is an entrepreneur, I was able to balance a lot of stuff off of him and say, “I’m thinking about doing this or whatever the case would be.” Ultimately, I was born with it. I don’t think there’s anything that I saw at a young age that inspired me to go into this. As I said, I have a little brother and I’m sure if I had other family members, they wouldn’t be interested in that at all.

It was something that was in me since as early as I can remember. What person creates things to start making money and the age of six years old, unless it’s born into their blood? That’s how I think about it. Unlike you, because you’re not in the entrepreneurship world, you don’t see a lot of the younger entrepreneurs. I met some of the few younger entrepreneurs that are out there, which thanks to social media, I would have never been able to meet years ago. I was talking virtually through Zoom to a kid in England and he’s the same thing. He is a seventeen-year-old entrepreneur who runs a marketing company. He is doing well in the marketing company. We had such a similar story. With different situations on different sides of the world. We were born into the world the same way. Entrepreneurship a lot of the times the greatest ones are born with it.

Do you think entrepreneurship can be learned?

It’s a difficult question to answer because of the practices, yes. What I do daily could be learned like how to answer emails, how to talk to people or whatever the case would be, how to do marketing. All that stuff could be learned but the spirit that takes you forward and the thing that makes you think differently, makes you think in a creative way and makes you think differently than other people. You can’t follow a script all the time. Average people are very good at following scripts. Entrepreneurs make the scripts, they write the sales scripts like the guy’s on the phone. There are 100 guys in the room that are calling up on the phone with that script, but the entrepreneur is the one who writes that script. I don’t want to put anyone’s dreams out of the way, but you are born being an entrepreneur. You may not realize it as early as an age as I did, but most people that are entrepreneurs were born to be entrepreneurs.

You’re describing passion. You have a passion for it, for whatever reason. I have a passion besides an investment passion. I like to write songs. I know I have no rhyme or reason why I want to do it. I’ve done it for 40 years. I don’t know why I keep going. I don’t even make money writing songs particularly because compared to what I do, it’s not worth diverting my attention from. Still, when I’m in my low spot, I write songs. I’m passionate about it.

REIS 349 | Young Investor

The Ultimate Guide To Teenage Investing

That’s a good way to put it.

You’ve got a book out. You’re an author.

I wrote the book. The book is called The Ultimate Guide to Teenage Investing. In my opinion, it is the number one teenage investing book. It’s for sale on Amazon. We’re trying to get it at some of the local bookstores as well. It is a guide that I’ve written that’s why hence The Ultimate Teen Investing Guide for any young investors out there, from I’d say anywhere ages 10 to 21. It’s a big age group of young people, but they’re looking to start investing. I’ve dealt with over 100 teenage investors either through running the club or through YouTube social media followings. I’ve had a lot of experience in teaching kids how to invest in the stock market. How to get them interested in it? How to get a passion for it? Where to invest their money?

In the book, I walk through how I make my stock investment decisions. When I’m looking at everything from the top of what stock screener I’m going to use, where I’m going to look for all the stocks and then what kind of different metrics I’m going to use to decipher which stocks I’m going to make investments in and which ones I’m not going to. When I did the book, I only know what works for me. I write in the book, “Here’s what worked for me. Here’s how I was able to build my portfolio. Here’s how we can get good returns in the Young Investors Club as well as my portfolio. Here are the same methods that you can use, which if they’ve worked for me over these last five years, there’s a good chance to work over the next 5, 10, 15 years for young investors.” That’s what I talk about in the book.

What are your average returns?

I believe, we had a 15% return for the Young Investors Club. It was a very good year. The stock market was up a lot. That helped honest about, but a 15% return. In my own investment portfolio, it is something around a 12% return. It’s good returns in both

I want everyone to go to 1000houses.com/YoungJack. Get over there. He’s going to be having things come out as we go. I’ve explained to Jack that the show notes are evergreen. If he ever has some other stuff come up or offering or if you are speaking or anything, to go ahead and put it in there. We’ll give you his contact information. Maybe you want to interview him yourself for a podcast. If you’re some podcasters out there, you’ll have his contact information out there to talk to him. I like to promote this guy as much as I could. Jack, I’d like to thank you for taking the time to come on.

Thanks so much for having me on. It was a pleasure to meet you. I look forward to talking a little more afterward about your real estate career. All the real estate investors, young investors and old investors out there, I would say, I’m looking forward to entering the business world. I haven’t had the time to start entering the business world until the end of 2019. I’m looking forward to 2020 and there’s so much opportunity out there. The one last piece of advice that I’d give to all, I’ll speak to my own, the teen entrepreneurs out there are you guys got to start young. You guys got to find something you’re passionate about or whatever. If it’s business, great.

Find some business vehicles you’re passionate about, whether it be marketing or investing or lawn mowing. There are tons of different businesses that kids could do out there. Find something you’re passionate about, save them money, don’t spend it. Save the money and invest it and build a long-term portfolio that you’ll benefit from for many years. The last thing I’d say is the best ways to find me is my YouTube channel, which ironically it’s under my name, Jimmy Duke, which is because my parents won’t let me put my real name online until I turn eighteen. I want to address that little discrepancy there, but that’s the best way to find me online.

That brings me to a question. How are you able to do this stuff under age? Did you have a corporation formed?

Social media marketing is done through sole proprietorship. There is no LLC created yet. However, one of my clients is recommending that I get an LLC for legal protection. I’m looking into that. As far as investing, it’s done through a custodial account. My grandfather set up the custodial account for me. My dad’s in finance, there are a lot of laws and regulations if he sets it up under his name. That’s when my grandfather doesn’t enter his name. That’s pretty much how the legality structure works.

There are ways to do business if you’re underage. You’ve got to talk to people that know how to do it and do it legally and do it right upfront onboard. It’s my pleasure to talk to you. I appreciate you being on. I will do want to talk to you more. Go over to 1000houses.com/YoungJack. Thank you very much, Jack, for taking the time. You’ve been a pleasure to talk to. My hat is off to you. We’re going to go out and hung down some hogs or some pigs here. I’d like to thank TaxFreeFuture.com for sponsoring this episode. Please go to their website and find out what your financial advisors are not telling you and why they’re not telling you. We’ll give you our opinion on it. You can make your own decision, but it’s pretty crystal clear. Take control of your financial future. We all got to trust some people and get some advice somewhere, but at the end of the day, take that bull by the horns and be a bigger piece of your destiny. Thank you for stopping by to get you some Jack Rosenthal. We’ll see you on the next episode.


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About Jack Rosenthal

REIS 349 | Young InvestorJack Rosenthal is a 17/year old teenage entrepreneur. He’s the founder of StarSocial Media (A full service Digital Marketing agency) and the president of the World’s Largest teenage investment Club




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