Who wants to be a millionaire? I’ve had this dream ever since I was 8 years old. I used to write papers and draw pictures of what I'd do with the money. At the age of 24 I had successfully become a millionaire. By the age of 25 I had already lost it.

Much like myself, Timothy Sykes managed to turn $12,415 that his parents gave him for his bar mitzvah into $1.65 million in four years--all before graduating college. I reached out to Tim for an interview, because I love connecting with like-minded individuals as well as learning from the best out there.

Sykes, now 34, has $15 million in the bank, struggles with mastering the ins and outs of his orange Lamborghini, and is currently scouting European locations for his tentatively planned 2016 nuptials (possibly to be held on the Amalfi coast). He has been known to trade stocks or teach a master class in trading from trains racing through Portugal, huts in Kenya, or presidential suites in Rome. Many may refer to him as a "douchebag stock trader", but it's a moniker that he proudly wears. Sykes has been featured on many outlets like CNN and Larry King Live.

Recently, I chatted with him to learn more about what he does and his philosophy for trading and teaching. His unfiltered, brash, and rather refreshing candid style shines through in our discussion.

Tell me about what you do and why.

For me, I'm a stock trader but I'm also a teacher and I just want to show people about the power of the internet, and that it can be all done online. I'm working here from Amsterdam, and I made $8,000 on a trade this morning. I want to show them that you don't have to be confined to your little desk and that the internet changes everything. Basically, making money is f’ing cool and there's not enough rich people out there that are showing off the glamour of the lifestyle. I just posted a video of a presidential suite that we had in Madrid showing that off. I just want to inspire people to show them what's possible.

How is this part of your goal?

My goal is to create more millionaire students. My job is to get them to watch more video lessons and study. I'm like this drill sergeant reminding them about what they could have if they really wanted to really work harder than they ever have. That's something that every millionaire or self-made millionaire has worked harder than they ever thought possible to get where they are.

How many hours a day do you work?

It's more like how many hours a day do I not work. I work 17 to 18 hours a day.

What happens in that 18-hour work day?

Because I'm a stock trader, about four to five hours of that is just straight up trading. Then an hour or two a day I spend doing video lessons, two to three hours responding to emails, an hour or two doing tweets and blog posts and Instagram posts. Then it's dealing with my sales teams and then I might do an hour or two webinar with my students and my customers. Somewhere in there I try to get to the gym but the past few years have been crazy.

Tell me your story.

I grew up in a small town of Orange, Connecticut, with a population of 12,000. My parents invested all of their money into getting me into a good college. I was a tennis player in high school. I over trained so I got injured my senior year and had two casts on my arms, couldn't do anything, but I was already into a pretty good university, Tufts University. My parents gave me control of my bar mitzvah money, which was roughly $12,000. I couldn't really play tennis, I didn't have to study, and I couldn't really move, but I could type. It was 1999 and the stock market was going crazy but I thought I would lose all the money and it would be a good lesson. Instead, by the end of the year, I was obsessive with how to trade stocks and I became a stock trader. I skipped classes and traded stocks from my high school library and the $12,000 grew to over $100,000, which was kind of insane and by the end of freshman year it was over $800,000, which was totally insane for a middle-class kid like me.

What happened after college and the start of your stock-trading career?

I've made six figures each year in stock trading but a key moment in my life came when in 2007 I agreed to be on this show called Wall Street Warriors, a reality show. I can always make six figures trading stocks but I'm ambitious, greedy, and living in New York City. I had a hedge fund but it wasn't going anywhere because I was trading penny stocks and low-priced stocks like the Wolf of Wall Street. I bet against scams. I exposed scams. Sometimes I would buy small companies that had decent technology but long story short it wasn't a scalable strategy. I could never run a billion-dollar hedge fund. I thought then let me become a reality star. At the time, Puck [from The Real World] was the biggest reality star, so let me become Puck for finance. I was drunk on every show, kicking over fans and telling everyone my story of how I took this $12,000 and turned it into $2 million so I was wide open about the money that I had made. Most people aren't like that in finance because they are tight lipped. But I was drunk and the show became a hit and my plan worked perfectly. It wasn't on regular channels but it was on Mojo and it became the number-one selling iTunes reality show of 2008.

What happened after being on the reality show?

On the show, I was just trying to do things that were entertaining. I was trading but my fund wasn't growing so fortunately the television show interested people who wanted to turn their money from thousands into millions and I started getting 10, 20, 50, 100 emails per day. This is where there is growth because everyone that teaches in the stock market is pretty much a fraud. If you know how to make all this money, why would you teach others how to do it? But I had the perfect excuse. I could make decent money but my strategy would never be huge so it would be more profitable to teach it. I got an offer of $35,000 to write a book and I said I can do better on my own so I read up on all these books about self publishing and I created my own publishing company and then started blogging at TimothySykes.com only to promote my book. I thought I'd sell like a million copies but I only sold about 20,000 copies, which is pretty good for a self-published book.

How did social media change things for you?

My blog at TimothySykes.com started to take off and I got people saying they wanted to see these trades in real time so I started a newsletter and then I wanted to talk about it with other people and then I started a chat room. Then I did DVDs and thanks to the blog and promoting the book on social media I really did realize that social media was the future so my business grew like crazy not from the TV show but from me evolving and showing my trades on Twitter and Facebook and YouTube. The Daily Mail has called me the Wolf of Instagram because I'm showing off all these presidential suites and my orange Lamborghini, which makes me nauseous when I drive too fast because I don't know how to drive it. I basically do the same thing I did for the reality show but now through social media and all along I have 500 video lessons on YouTube and 300 premium lessons. People pay me to teach them the basics of the stock market and somewhere along the line my lessons get through to people.

Tell me about your success stories.

Well, there's the story of my top student, Tim Grittani, who turned $1,500 into $1 million in three years, which went viral on CNN. Now he is up to $2.7 million and he has his own DVD out too.

What else do you do?

I have the Timothy Sykes Foundation, which has raised over $600,000, and my latest DVD all goes to charity. Basically, I love making money, I love teaching, and I love trying to get the word out there about how to trade stocks in a very safe way. I call myself the castrated choir boy because I trade conservatively and now I teach other people to trade carefully because most everyone loses everything in stock trading.

Teach me a little bit of your strategy.

My number-one rule is cut your losses quickly. It doesn't matter if you have 15 years of experience or you are just starting, you can be wrong about any stock at any time. If you buy a stock or short a stock and it starts going against you by more than 5 percent, then cut it so that way you don't let it blow up. It only takes one bad trade to wipe you out, so think about that in the back of your mind, that fun little thought. Rule number two is there are good companies and bad companies and just because a company is bad doesn't mean you can't make money off of it.

When you are investing in stocks, how long do you typically hold it for and what type of volume are you buying in?

I hold anywhere from a few hours to a few days. My goal is to make between 20 and 40 percent on my money. This morning, I made 50 percent on my money holding it over night. Usually, the volume I buy into is about two and 10 million shares per day. I trade with a very small account in order to teach because I don't want to be too big for the market. I am trading as though I am one of my students. I go back to $12,000 every year and I try and grow it. This year, I started with $100,000 and I'm basically up to $220,000 so I've shown the students how to double their money in seven months even though the overall stock market is flat. Last year, I made $800,000 so I trade with a small amount in order to teach but I also want to show how to grow an account.

What tips would you give newbies out there?

You don't have to be a rocket scientist or be great at math. You just have to understand a few key indicators and that is namely price action and chart patterns. You don't have to even understand the technology or the biotechnology. When you are buying a stock, you are buying an asset that is moving up and down in price. You are not actually investing in the actual product that company makes or even the company itself. It's only about the stock.

You have been known to be a little bit douche-y and you've even referred to yourself as a douchebag, so is that what you are going for?

Yes. I'm not necessarily proud of it, but I also know what inspires people. I don't choose my orange Lamborghini but that is what inspires. I've posted pictures of these amazing paintings in Italy and no one gives a shit. I don't think you can prioritize your values over what others value when you are trying to be a teacher or an inspirer. You have to sort of give into the crowd. Let me give you an example. I've posted two 45-minute video lessons. One is a video that explains the ins and outs with the upsides and risks and on the little jpg thumbnail of that video and I post a stock chart and then I post another of the exact same video but with a picture of my orange Lamborghini. The orange Lamborghini thumbnails got four times as many views. I want to teach and I want my people to actually study so by showing the rewards at the end with the pot of gold it gets them to study harder. I pretty much do anything I can to get my students to study harder. In fact, if that makes me look like a douchebag or an asshole, it's fine. My ego can take it.

How do you deal with family and friends begging you for family?

I created a charity to give to the less fortunate where we partner with Make-a-Wish and the Boys and Girls Club. The other day I filmed a $20,000 giveaway and I went to a random bar in L.A. and gave away $20,000. I also gave this lady $2,000 and she started a daycare. However, with family and friends, I insist on giving them DVDs or video lessons because I say, aside from just money, I can give you knowledge and then you can create your own which is infinitely better and more important.

What makes you different than other stock market teachers out there?

The main differentiator is that this is all about education and I think that by far I am the most out-there teacher. Like I've done eight-hour-straight webinars, answering every single question, going over every single stock. I'm at the point where I'm outside my own brain. I've gone to places that teachers have not gone and I think more teachers should. The car becomes a catalyst to getting more people to pay attention. Our culture loves fame, wealth, and signs of it. I'm not that smart, but what I teach includes lessons from both my success and failures. From my hedge fund, I did lose 35 percent because I invested in a family friend's company. When I tried getting away from my strategy, I lost. I share my losses. We need to be more open with the losses. I wish more millionaires would talk about their losses and successes and just be more open about their entire journey. I would love to learn about every single millionaire's journey. I think it would be incredible. It would even be great to hear from those that have built amazing businesses but that maybe are now not worth a dime or they went bankrupt. There are still so many lessons. I'm kind of an over-sharer and wish more people were like that.

What are your financial goals for the next 10 years?

My goal is to create more millionaires. If I get up and the morning and say, "Oh look, I made another $10,000, that's cool." Or, if one of my students made his first 10,000, that's even cooler. I love it when people experience it for the first time. My first $100,000 profit was when I was a freshman in college in. I didn't even understand that you could do that in one day let alone as a freshman in college. I took my whole dorm out to dinner and it was one of the most incredible days of my life. I want that aha! moment from more people.

If you were to lose it all today one bet and go bankrupt that day, what would you do?

That would violate my rule number one about never risking it all, but if that happened I would probably write a bad-ass blog post about it and everybody would learn from it and just try to be open about it. I would have to change my blog from TimothySykes.com to MillionaireToZero.com and talk about it and try to build a business around it. You don't need to be afraid of it. You've heard the saying fail forward, fail fast, fail often and then you get better and I think that is what most entrepreneurs -- if not, all entrepreneurs -- should do. Never be afraid of failure and if you do have failure, look at it as a sign and look at how you can adapt it. There are opportunities in everything you do and you just have to have a positive outlook on it and be willing to accept it. In today's world and thanks to new technology, you can always reinvent yourself and you can always come back better, smarter, stronger, and wiser than before.

What is the most you have lost in one day? Is $100,000 the most you made in one day?

One day, I lost $180,000. I was shorting a stock and it kept going higher and higher and I had to cut losses. The very next day, I re-shorted the stock because I was like this stock has to crash and I got back on the horse and I made $220,000 so overall I made $40,000. It was the worst $40,000 that I've made but it happens sometimes with trading. Now I trade with a smaller account. Last year, I had two $70,000 profit days. It all varies.

Do you allow people to piggyback on your trades?

No. While there is software and others that do allow that, it's not part of my plan. For me, it's about having independent thoughts and learning the framework for yourself and using my trades as a guide to create your own framework. The best thing about my millionaire students is that I didn't give them a million dollars and I didn't tell them which stocks to buy. They took from what I have shown with my own trades and created their own strategies, which are actually slightly different than mine. We may trade similar stocks and similar patterns, but we all have our own different strengths and weaknesses. Some of my students have much more patience than I do and they hold stocks for weeks. I love education because there are endless variations so you never have to learn from someone or consider this is an exact science. Variation is a beautiful thing and it's what makes entrepreneurship and the stock market great.

Should I buy a Lamborghini?

I actually wrote an article with some of the reasons why entrepreneurs should have Lamborghinis for their businesses. That car has paid for itself 10 times over. I know I can barely drive it, it sucks to park, and it's uncomfortable for road trips, but, from a business standpoint, it is the single best investment I made. It takes you from six figures to seven or eight figures. You don't even have to buy a brand new one. It's amazing how much our society values cars. My friend has a Jeep Grand Cherokee, which is so much more comfortable but it doesn't play well for what I'm trying to do. I suck it up and drive a Lamborghini.

One last question. How old are you?

I'm 34 years young right now.

Okay, so I have two years to put a couple more million in the bank.

Time to catch up!

I think that is exactly what I will do. I just need to stop by the Lamborghini dealer first. If everyone could be this open and honest, imagine what business--and maybe even politics--might be like. I'd like to see him in a debate with Donald Trump.

Published on: Sep 2, 2015