Roland Wolf: 7 Tips From a Pro Athlete Turned Trader

By Updated on April 18, 2022

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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

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 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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Comments (1)
Author imageTimothy Sykes
Hey Everyone,

As many of you already know I grew up in a middle class family and didn't have many luxuries. But through trading I was able to change my circumstances --not just for me -- but for my parents as well. I now want to help you and thousands of other people from all around the world achieve similar results!

Which is why I've launched my Trading Challenge. I’m extremely determined to create a millionaire trader out of one my students and hopefully it will be you.

So when you get a chance make sure you check it out.

PS: Don’t forget to check out my 30 Day Bootcamp, it will teach you everything you need to know about trading.

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