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Roland Wolf: 7 Tips From a Pro Athlete Turned Trader

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Written by Timothy Sykes
Updated 4/18/2022 10 min read

Roland Wolf’s Top 7 Trading Tips: Key Takeaways

  • See where Roland was just four years ago in 2017 and where he is now — what an incredible journey!
  • From skeptic to student — see why Roland ultimately chose me to be his mentor…
  • Take in Roland’s top trading lessons and how they can help you!

Apply for the program where Roland Wolf honed his trading strategies!

Roland Wolf: My Student Turned Mentor

roland wolf standing and smiling
© Millionaire Media, LLC

Hey, Tim Sykes here.

I’m SO excited for this update on one of my top students and how you can learn from him…

Roland Wolf joined my Trading Challenge about five years ago. Like many traders, he didn’t study much at first. He tried to follow alerts and chased stocks…

No big surprise it didn’t work for him.

After learning a few lessons the hard way he realized something … The only way he’d improve at day trading penny stocks was by studying his butt off. So that’s what he did.

Back then, Roland kept his 9-to-5 job and would squeeze in studying into every spare minute. He got up early, maximized his breaks at work, and stayed up late to study more. I was concerned for his health at one point…

Sometimes he’d take the long way home from work just to finish listening to one of my DVDs.

Hard work wasn’t new to him. When he was little, his soccer coach made him run suicides in his backyard before school. I know what that’s like. Back when I was training to be a tennis champ I ate codfish every morning for breakfast.

We both get the athlete mindset and how that can help us in our trading and education.

And in 2020, Roland’s hard work paid off for him — he reached the $1 million milestone.* But for Roland, it’s not about the money. He just wants to provide for his family.

Learn more about Roland and how he trades in this video:

Now, I’ll hand it over to Roland so he can share his top lessons. Take notes!

Roland Wolf’s Top Penny Stock Trading Tips

© Millionaire Media, LLC

Roland here. First off, I want to thank Tim for that awesome intro AND everything I’ve learned from him.

I’m happy to help traders, especially those just getting started. As Tim mentioned, I had to learn some of these lessons the hard way. And some I thankfully learned from my mentor, Sykes.

You can either learn them here and now … or wait until you take a big loss. Your choice.

Lesson 1: Follow Rule #1

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Lesson 1 is also Tim’s #1 rule: cut losses quickly.

This is the biggest lesson I learned from Sykes and how I stayed in the game at the beginning. It kept me safe and protected my small account so I could focus on the process.

As a newbie, I didn’t know what I didn’t know.

But I knew I couldn’t afford to blow up my account.

I had a wife and kids to look after. Safety was the name of the game. It still is.

This rule will serve you throughout your trading journey.

Lesson 2: Build Your Knowledge Account

Learn as much as you can and find a good mentor.

Before you even make a trade…

Do your due diligence on your mentors. There are a lot of fakes out there, so be careful.

When I found Skyes, I was skeptical at first. But after spending time in Pennystocking Silver, I was ready to join the Trading Challenge.

Make sure your mentor is the real deal. For example, Sykes shows all his trades on Profit.ly. I know he’s legit because he’s transparent.

Here are a few videos that helped me the most early on…

Lesson 3: Practice

Once you have a basic understanding of the market, you have to get a feel for it.

Trading can be stressful. Things move fast and there’s a lot of volatility in penny stocks. Not to mention the emotions that come with risking money.

Try taking the money out of the equation. Paper trading can be a great way to do that.

As Tim says, this is a marathon, not a sprint. Don’t waste your hard-earned cash taking big positions in the beginning. You’ll regret it. I know because I’ve been there.

When you do start, trade small. You can scale up once you can better handle your emotions.

Lesson 4: Prepare Ahead of Time

roland wolf in italy on boat
© Millionaire Media, LLC

I learned this the hard way. When I started, I’d roll out of bed 30 minutes before the market open and peer at my screen through sleepy eyes.

I didn’t have a plan and I wasn’t prepared. Now, all that’s changed.

I run my scans the night before and plan for the next trading day. And I wake up two hours before the market open so I’m wide awake for the starting bell.

Preparation is everything. That’s something I learned from my pro soccer days. If you want to perform well you must come prepared. The stock market is the same.

So I keep detailed watchlists and refresh them every morning. If you want to get ahead you need to do everything you can to prepare. Get into the right mindset.

Lesson 5: One Trade at a Time

Trading can be overwhelming at first. Even now, if I get undisciplined I may slip up.

The market always changes. So you have to constantly adjust your trading to adapt.

Take it one trade at a time.

If you think about the end goal of making $1 million, you could get discouraged. You might jump into bad trades to try to reach the finish line faster.

Trust in the process and wake up every day ready to do your best. The only trade that matters is your next one. Then it’s the one after that.

Remember the marathon analogy? Take it one step at a time.

Lesson 6: Take What the Market Gives You

Roland Wolf on plane and looking at charts
© Millionaire Media, LLC

This is a tough lesson. A lot of people get into the stock market looking for a big paycheck. They want that one trade that makes them a millionaire.

That’s called gambling.

Consistent profits aren’t easy. Sometimes there are trades and sometimes there aren’t.

You can’t take more than what the market gives you.

Sometimes that means a quick profit or cutting your losses quickly. Stay humble or risk the market humbling you.

What’s your plan? Buy a random penny stock with $10 and then hold it until you can buy a Lambo? That’s not realistic.

This is a slow process. And you must learn the right lessons to reach your goals. Stop trying to squeeze out profits that don’t exist.

Lesson 7: Work for Your Goals

Here’s my final trading tip: Don’t give up.

The road to self-sufficient trading is long and hard. Remember, 90% of traders lose. The odds are against you. But know that anyone can learn to do this.

It’s not rocket science, but it does take a lot of time and effort. I studied every day for years. And I don’t mean for an hour or two a day. More like 15–17 hours.

I’m still learning every day.

Remember how difficult this task is and focus on the process.


When people first started telling me I inspired them to trade, it was a little weird. To me, I was the same person. I didn’t think of myself as anyone extraordinary.

Now I see that I can help new traders. I like being able to give back to the community that helped me get to where I am today.*

Are you ready to work your tail off for what you want? Apply for Tim’s Trading Challenge. But only if you have discipline and commitment. I think it’s worth the effort. Then again, to me, there’s no such thing as studying too much.

Leave a comment and share your thoughts. Which trading lesson speaks to you the most? We love to hear from you!


*Results are not typical and will vary from person to person. Making money trading stocks takes time, dedication, and hard work. Most who receive free or paid content will make little or no money because they will not apply the skills being taught. Any results displayed are exceptional. We do not guarantee any outcome regarding your earnings or income as the factors that impact such results are numerous and uncontrollable. Tim has also hired Roland to assist in his education business.

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Timothy Sykes

Tim Sykes is a penny stock trader and teacher who became a self-made millionaire by the age of 22 by trading $12,415 of bar mitzvah money. After becoming disenchanted with the hedge fund world, he established the Tim Sykes Trading Challenge to teach aspiring traders how to follow his trading strategies. He’s been featured in a variety of media outlets including CNN, Larry King, Steve Harvey, Forbes, Men’s Journal, and more. He’s also an active philanthropist and environmental activist, a co-founder of Karmagawa, and has donated millions of dollars to charity. Read More

* Results are not typical and will vary from person to person. Making money trading stocks takes time, dedication, and hard work. There are inherent risks involved with investing in the stock market, including the loss of your investment. Past performance in the market is not indicative of future results. Any investment is at your own risk. See Terms of Service here

The available research on day trading suggests that most active traders lose money. Fees and overtrading are major contributors to these losses.

A 2000 study called “Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors” evaluated 66,465 U.S. households that held stocks from 1991 to 1996. The households that traded most averaged an 11.4% annual return during a period where the overall market gained 17.9%. These lower returns were attributed to overconfidence.

A 2014 paper (revised 2019) titled “Learning Fast or Slow?” analyzed the complete transaction history of the Taiwan Stock Exchange between 1992 and 2006. It looked at the ongoing performance of day traders in this sample, and found that 97% of day traders can expect to lose money from trading, and more than 90% of all day trading volume can be traced to investors who predictably lose money. Additionally, it tied the behavior of gamblers and drivers who get more speeding tickets to overtrading, and cited studies showing that legalized gambling has an inverse effect on trading volume.

A 2019 research study (revised 2020) called “Day Trading for a Living?” observed 19,646 Brazilian futures contract traders who started day trading from 2013 to 2015, and recorded two years of their trading activity. The study authors found that 97% of traders with more than 300 days actively trading lost money, and only 1.1% earned more than the Brazilian minimum wage ($16 USD per day). They hypothesized that the greater returns shown in previous studies did not differentiate between frequent day traders and those who traded rarely, and that more frequent trading activity decreases the chance of profitability.

These studies show the wide variance of the available data on day trading profitability. One thing that seems clear from the research is that most day traders lose money .

Millionaire Media 66 W Flagler St. Ste. 900 Miami, FL 33130 United States (888) 878-3621 This is for information purposes only as Millionaire Media LLC nor Timothy Sykes is registered as a securities broker-dealer or an investment adviser. No information herein is intended as securities brokerage, investment, tax, accounting or legal advice, as an offer or solicitation of an offer to sell or buy, or as an endorsement, recommendation or sponsorship of any company, security or fund. Millionaire Media LLC and Timothy Sykes cannot and does not assess, verify or guarantee the adequacy, accuracy or completeness of any information, the suitability or profitability of any particular investment, or the potential value of any investment or informational source. The reader bears responsibility for his/her own investment research and decisions, should seek the advice of a qualified securities professional before making any investment, and investigate and fully understand any and all risks before investing. Millionaire Media LLC and Timothy Sykes in no way warrants the solvency, financial condition, or investment advisability of any of the securities mentioned in communications or websites. In addition, Millionaire Media LLC and Timothy Sykes accepts no liability whatsoever for any direct or consequential loss arising from any use of this information. This information is not intended to be used as the sole basis of any investment decision, nor should it be construed as advice designed to meet the investment needs of any particular investor. Past performance is not necessarily indicative of future returns.

Citations for Disclaimer

Barber, Brad M. and Odean, Terrance, Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors. Available at SSRN: “Day Trading for a Living?”

Barber, Brad M. and Lee, Yi-Tsung and Liu, Yu-Jane and Odean, Terrance and Zhang, Ke, Learning Fast or Slow? (May 28, 2019). Forthcoming: Review of Asset Pricing Studies, Available at SSRN: “https://ssrn.com/abstract=2535636”

Chague, Fernando and De-Losso, Rodrigo and Giovannetti, Bruno, Day Trading for a Living? (June 11, 2020). Available at SSRN: “https://ssrn.com/abstract=3423101”