Roland has been an athlete his entire life. He started playing soccer at the age of four and developed a strong passion for it. This eventually earned him a full-ride scholarship to Boston University.

While there, he helped lead the team to a conference championship and an NCAA tournament title. But he would eventually quit school and chase his dreams of playing professional soccer. 

He joined the professional league in Croatia, which allowed him to play all around the world. These were some of his best times. But unfortunately, a serious ankle injury ended his career.

Roland was left with nothing to do but head home. He didn’t get a degree, and he couldn’t possibly continue playing soccer. It was around this time that his life would temporarily go back to ‘normal.’

Roland married his high school sweetheart. They have three children together: two boys and one girl. He’s a devoted family man driven by a desire to provide for his family — in fact, his family is one of the main reasons why he started trading. 

In the years leading up to his day trading career, Roland worked a typical 9-to-5 job that he dreaded. He was making about $50,000 a year, which was barely enough to get by. He never got handouts in life but was still convinced he deserved more. 

Before trading, he tried playing blackjack. He was inspired mostly by the movie “21.” He learned to count cards, but casinos constantly take measures to prevent it from working. Without a team like in the movie, he’d be outgunned almost anywhere, regardless of his counting skills. 

His next option was the stock market. 

Trading on the Side

Roland’s trading journey started as a side hustle. He needed a way to potentially earn some extra cash for bills. He never knew that he’d end up finding his next passion and becoming a pro-level day trader.

When he first started trading, he didn’t tell his friends or family about it. He didn’t want to hear them say things like, “the stock market is a scam.” Instead, he was determined to find out for himself.

Money was tight at the time. Roland only had about $800 to trade with. He wasn’t doing any effective research — just looking for a few reliable companies that make for good buys. 

His first trades ended up being $400 worth of Barrick Gold Corporation (TSE: ABX) and $400 of Bank of America Corporation (NYSE: BAC). He had no strategy and therefore wasn’t sure what to expect. 

After a few months, BAC didn’t do anything … but ABX doubled! This profit hooked Roland. If there was a way to find these moves before they happened, he wanted to learn how. 

He started considering that day trading as a career might be possible, but not without a legitimate strategy. So it was time to find one. 

First Encounter

Roland started searching “penny stocks” and “how to trade stocks” on Google, but most of the results seemed like a scam. But then he found one trading mentor who stood out from the other gurus — Tim Sykes.  

For one, Tim’s testimonials seemed authentic. It appeared he had successfully taught many students the fundamentals of day trading. Also, there were some traders with insane profit curves at the time. Many of them claimed to only trade a handful of trading patterns.

He saw that Tim had a mentor program called The Millionaire Challenge (since rebranded as the Trading Challenge). Students who applied and got accepted had instant access to a ton of exclusive learning material. 

Not being entirely sold, Roland waited on joining the Trading Challenge, instead opting to join Pennystocking Silver to see how things went. 

It was around this time that he decided to increase his account size. He had about $1,200 from his first two trades, but also added three paychecks on top. 

This put his account right around $4,000. 

A Chaser’s Dilemma

Roland didn’t immediately grasp any single trading strategy. 

He was just trying to be at the computer and follow Tim’s alerts in the chat room. But as he quickly learned, this was not a winning strategy. 

Roland found that he was always late to the moves, and would usually end up chasing. The impulse buy would often lead to a panic sell because he didn’t have a plan. 

He tried chasing the alerts over 10 times in a row, losing money on every trade. He realized that if he kept it up, he would never become a self-sufficient trader.  

He wasn’t making use of the material in Pennystocking Silver. He wasn’t creating watchlists to narrow down good setups. And most days, he was rolling out of bed a few minutes before the market opened.

If Roland wanted any shot at making this a career, he’d have to break all of these bad habits. It was time to buckle down. 

Roland’s Study Grind Begins

Roland decided that education was now his top priority. 

All of Tim’s self-sufficient students had one thing in common: they studied trading material for hours and hours each day until it all started to click. He knew he wasn’t special, and that this would be his only option. 

The Pennystocking Silver subscription included all the educational content he needed. But a select few DVDs were a staple for him in the beginning:

He started watching every video available, soaking up all the crucial information in the process. The lessons started to fill in the knowledge gaps. They were pointing him in the right direction.

Roland was particularly interested in one trader … Tim Grittani.  

After studying Grittani’s style, he started to realize that he was buying where Gritanni was shorting. This led him to make a promise to himself: “I’m not going to buy Gritanni’s shorts anymore.”

Another big influence on Roland was the legend LX21 (who has been inactive for a few years as of 5/2021). He taught Roland to treat trading with respect, like any other real profession.

Roland had experience as a professional athlete. He knew how hard it was to play at those elite levels. He decided to put the same effort into trading as he once put into soccer. This meant working harder than anyone else. 

So that’s exactly what he did. Roland began studying the markets for 17 hours a day.

At this point, he decided it was time to upgrade from Silver to the official Trading Challenge. He knew it was a major step, but he was ready to start learning from Grittani and Mark Croock.

He was obsessed. He was willing to make sacrifices to make it work.

Photo courtesy of Roland

A New Dawn

The market opens at 6:30 a.m. in Arizona. This meant Roland had to be up extra early to trade the open before going to work at his 9-to-5. 

He’d also come back to markets on his lunch break to find potential afternoon setups. While he was working, he’d listen to trading lessons. 

Then he was driving home, more trading lessons. Sometimes he would even make a few extra laps around the block to squeeze out all the knowledge he could. 

One time, his wife caught him driving right by the house. She was understandably confused. 

Even throughout the process of studying and building his education, he never failed to spend time with his family. No career in the world could make him forget about that. But when they went to bed, Roland got right back to studying.

For a long time, his life revolved strictly around trading and family. There wasn’t time for anything else. But that’s the level of dedication Roland needed to become self-sufficient. 

His knowledge kept growing and growing. One of his main patterns was the multi-day breakout, and he constantly tracked his trades to find ways to improve. 

After what felt like a lifetime of studying, the money finally started to come. He realized that in the world of day trading, you only get out what you put in. 

He continued to follow a strict plan and only traded when he had an edge. This process allowed him to eventually grow his account to over $200,000 — four times his annual salary!

At this point, he felt in his heart that he was ready to start trading full time. He quit his 9-to-5 desk job and became a full-time trader.

Ever since then, he’s stuck to a well-defined process for finding penny stock runners. To this day, he still pretty much uses the same strategy. 

Now, as of May 2021, Roland’s profits are over $1.2 million.*

Photo courtesy Roland Wolf

New Mentor on the Block

Roland’s not a young gun anymore. These days, he spends the majority of the time juggling daily life as a father of three. As you can imagine, finding extra screen time can be tricky. 

You’ll find Roland on the front lines when the setups are abundant. When the action fades, he adopts a “sit on your hands” mentality. He’ll lock in singles and avoid overtrading. 

Roland created $1K Paydays (currently being rebranded Wolf Alerts as of May 2021), where traders of all experience levels can learn directly from him. There are daily watchlists and frequent webinars discussing the markets. 

He also offers a masterclass for highly dedicated students. You’ll see him break down his strategies step by step, including all of the fine details. 

Roland is just getting started in his work as a trading mentor. He loves helping new traders find their niche in the markets.

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