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Success Stories

10 Lessons From 10 Top Traders

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Written by Timothy Sykes
Updated 3/5/2021 21 min read

The 10 top traders featured in this post all have similarities. But they’re also all different. Everyone in this post developed their own style. They all have different strengths and weaknesses.

As you learn to trade, your job is to find what works best for you. So learn something from each of these traders and make it your own.

The top earner on this list, Tim Grittani, has made $12.7 million in a little under a decade.* That’s the best-case scenario for anyone starting with a small account. Believe me when I say the odds of you becoming the next Grittani are small. But his approach is repeatable. And that’s the lesson I hope you’ll take away.

When you see how they’ve all progressed from small accounts to top traders, it will start to make sense. And I hope it will inspire you to learn as much as you can from all the content my team and I create.

(*Please note: My results, along with the results of my top students, are far from typical. Individual results will vary. Most traders lose money. My top students and I have the benefit of many years of hard work and dedication. Trading is inherently risky. Do your due diligence and never risk more than you can afford to lose.)

Get Inspired by 10 Top Traders

tim sykes challenge students
Pictured Left to Right: John Papa, Jack Kellogg, Dominic Mastromatteo, Timothy Sykes, Don Mastromatteo, Matthew Monaco, Kyle Williams

What are you capable of when you have access to all this content and the right tools?

I’m proud of these 10 students — they longer need me, my video lessons, watchlists, or trade alerts. They don’t need my webinars because they’ve been studying with me for years.

You might think each of these top traders has one big lesson to share. Not true. Each of these traders is successful because they learned several, if not all, of these lessons.*

So take what they give as a gift, but NEVER take it for granted. Use it as inspiration to study.

Top Traders Come From the Trading Challenge

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Not everyone knows this, so I need to emphasize it. All my top students come from the Trading Challenge. When you join the Trading Challenge…

You get video lessons, daily watchlists, and commentary. And you get trade alerts, the Challenge chat room, and two to four live webinars per week. Plus, you get access to all the archived webinars.

Grittani — the first top trader on this list — has given 69 webinars. That includes Q&A and live trading where you see his screen.

So if you’re serious about gaining freedom: Apply for the Trading Challenge today.

(If you’re new to penny stocks, start with the FREE penny stock guide.)

Let’s start with…

Four Millionaire Students

Each of these four top traders has made over $1 million in trading profits. They’ve changed not only their lives but the lives of their families.

Tim Grittani

Grittani is one of the best penny stock traders in the world. He’s reported over $3.6 million in 2020 alone.* But it wasn’t always that way. Grittani lost his first $1,500 and had to start over. He didn’t make anything for his first nine months.

Tim takes big position sizes now, and that’s key to his big gains in 2020.* But in the beginning, his focus was on testing…

Lesson 1: Test Now, Size Up Later

If you look at his early trades, he had small wins — rarely over $100 for several months. You’ll laugh when you look at his early losses. He describes them as ‘trading implosion trades while learning.” 

Those ‘trading implosions’ were tiny compared to what he does today. But his focus was on testing and tweaking, NOT the dollar win or loss.

Now, Tim Grittani takes what he calls paper cuts while testing. His paper cuts are $10K or even $20K. Read this key post to see what I mean: “15 Lessons from an Amazing Tim Grittani Webinar.”

The lesson is to take small losses. Test. Take paper cuts and learn about the price action. Learn how the stock trades. 

As you grow your knowledge account gain experience, you can size up.

Michael Goode

Michael Goode was my first millionaire student. The funny thing is, Michael wrote a post back in 2008 called “Timothy Sykes is full of bullship.”

Read it and check out my comments below it. Here’s what’s great … Michael gave my teachings a try and completely changed his view. Now he’s made $2,602,169 in trading profits.* If my strategies can turn haters into millionaires, there must be something to them, right?

Lesson 2: Conservative Trading Pays Off Over Time

Michael Goode is more of a conservative trader than Tim Grittani. His profit chart shows how slow and steady wins the race. He’s a perfect example of what I say so often: it’s a marathon and not a sprint.

Michael joined with me to create the “Read SEC Filings“ DVD. If you want to learn the parts of SEC filings that matter, watch it and take notes.

The next top trader is…

Mark Croock

Mark Croock watched all my video lessons three times. He asked me if he could categorize and tag the video lessons on Profit.ly. Of course, I said, “Yes, that would be amazing.”

Now he’s made over $2.1 million in trading profits. In 2020 alone, Mark has made $792,848.* Check out Mark’s profit chart here.

This post has a few bonus lessons as a thank you for continuing to read. Here’s the first…

Bonus Lesson: Apply My Patterns to Different Market Niches

What I find amazing about Mark is that he’s taken my patterns and applied them to different market niches. He uses my patterns and framework to trade options on higher-priced stocks. If you want to learn how Mark does it, check out this interview I did with him.

Back to the main lesson…

Lesson 3: Get Inside the Mind of Successful Traders

Mark spent so much time studying, it’s almost like he’s inside my head. When he gives Challenge webinars, I like to listen while trading. Check this out…

Sometimes in his webinars, Mark will say something like, “Sykes is probably about to sell.” And he says it just as I’m about to type my alert! I’m thinking … get out of my head. But it shows you how much he’s studied.

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The lesson is that you have to study so much that you can almost predict what these traders will do on a given trade. Again, learn something from each. Do it to figure out what works best for you. But if you hone in on one strategy, go deep with it. Figure out what top traders do on the kinds of plays you like.

Ready for the next top trader? Let’s do this…

Roland Wolf

Roland started with $4,000 of his own money four years ago. He likes to dip buy and my morning panic pattern. He also does a little short seller. SureTrader was good at finding shares to short. But when they stopped being good for short selling. Earlier this year, Roland passed $1 million in trading profits.* See his profit chart here.

I love the next lesson and Roland’s the perfect example…

Lesson 4: Find Your Reason Why and Go For It

Roland trades conservatively because he has a family. For Roland, his family is his reason why. His whole motivation for learning to trade was to give his family a better life. That’s what got him into stock trading.

Roland studied up to 17 hours per day his first year and still puts in five or six hours per day preparing to trade. He found his reason why, then put everything into making it happen. He didn’t let anything get in his way.

Fun fact: I happened to be in Arizona when Roland’s wife was giving birth to their third child. I called to ask if he wanted to meet up and he said, “Not right now, I’m at the hospital. We’re having a baby!” Then he invited me to come and meet the baby. So there I was at the hospital thinking, “This is crazy, I’m holding my student’s baby.”

Now you know something about these four millionaire students, you might be thinking…

Come On … These Guys Got Lucky

The reality is, they all figured out how to make small gains over time. They have different strategies, but each gained financial freedom one trade at a time.*

To prove my point, check out these…

Lessons From Three Up-and-Coming Six-Figure Traders

midwest meetup
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These three top traders are all under 25 years old. Two of them, Matt Monaco and Kyle Williams, just graduated from college. The third, Jack Kellogg, didn’t even go to college and he’s made the most of all three.* At least so far. Now that Matt and Kyle graduated from college, I’m excited to see what they can do.

Let’s start with…

Jack Kellogg

Based on his profit chart, I’m guessing Jack Kellogg will be my next millionaire student. In three years as a Trading Challenge student, he’s made $916,267 in trading profits. Over $750,000 of that has come in 2020.*

Of the three top traders in this section, Jack’s the most aggressive. Maybe that’s because he wears his chain on the outside of his shirt. (Fun fact: Jack had never watched “A Night at the Roxbury” before I started giving him a hard time about his chain. That’s how young these guys are!)

Lesson 5: It’s a Marathon and Not a Sprint

Jack is in year four as a Trading Challenge student. Like every one of the top traders featured in this post, it took time. Now, Jack often makes a solid yearly salary in one month. For example, Jack has already made over $57,000 in October. Even in September, which was by far Jack’s worst month this year, he made $8,278 in trading profits.*

The lesson is, be willing to put in the time and effort to build your knowledge account. One way Jack did that was by becoming a master of my seven-step framework…

Bonus Lesson: Master the “Pennystocking Framework”

Jack follows the rules in my “Pennystocking Framework” to a T. He knows it inside out. For those of you who know it, Jack loves numbers 4, 5, and 6 from the framework. In other words, he shorts the crash, longs the bounce, and shorts the crash again.

If you’re not familiar with my “Pennystocking Framework,” do yourself a BIG favor and start learning it. More on how to do that in a moment, so keep reading…

Kyle Williams

Kyle Williams is one of the most meticulous traders I know. He’s made $510,599 in trading profits. Like Jack Kellogg, 2020 is a breakout year for Kyle. He’s made over $384,000 this year alone.* Check out Kyle’s profit chart here.

Lesson 6: Be Meticulous

Kyle found what works best for him — he’s primarily a short seller. The lesson is in how Kyle figured it out, and how he continues to grow as a trader.

Kyle tracks everything. He’s been doing monthly recap videos and posting them on Profit.ly and YouTube since June 2019. Watching his recaps reveals just how meticulous he is with every aspect of trading. He shows spreadsheets, talks through trades, and explains his thought process.

I often tell students to be meticulous. Kyle is a standout example of what can happen when you do it.

Matthew Monaco

Matt Monaco is another example of a young top trader on the rise. He’s coming on strong. He’s also responsible for organizing the 30-Day Bootcamp we released earlier this year.

After a few years of studying, Matt started to see more success. So he asked me if we could do a short guide sharing everything he’d learned in three years. Of course, I was ecstatic.

The 30-Day Bootcamp is a must-watch guide. For answers to the most frequently asked questions about the 30-Day, read this post.

But the smart move is to just get it now: Access the 30-Day Bootcamp today

I also mentioned my “Pennystocking Framework” above. When you get the Bootcamp, you get my “Pennystocking Framework” DVD as a BONUS. It’s crazy. For less than $100 you get an incredible amount of educational content. Get it. Watch it. Study it.

The cool thing is, when we recorded the Bootcamp, Matt quickly became a near-perfect example of…

Lesson 7: Preparation Meets Opportunity

The month we recorded the lessons, Matt made $15,710.* Not bad, right? Most people would LOVE to make that kind of money. (Not to mention he was still in college at the time.)

But here’s where it gets good…

The month after we recorded the Bootcamp lessons, Matt made $47,010. Then, in June, he made $93,741 in trading profits!* That’s HUGE!

Understand Matt is in his fourth year as a Trading Challenge student. And this year has been exceptional for penny stock traders as long as they were prepared.

All the top traders mentioned in this post are profiting big during the pandemic. Why? Because they’ve been studying for years.

Jack, Kyle, and Matt are co-hosts on the TWIST podcast. They share so much information that I’m surprised it’s free.

Three Six-Figure Students With Powerful Lessons

tim sykes grand canyon
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Too many people see opportunities but don’t know what to do. If that sounds like you, you need to do everything in your power to learn and then take action. Some of you will need to focus on the first step: learning. You might need to just watch.

Then, you need to experience what it’s like to miss a trade or get a partial position. Maybe you need to be completely wrong and learn to cut losses quickly. Wherever you are in the process, there’s always room for improvement.

Keep that in mind as you learn lessons from these three six-figure traders…

Mike “Huddie” Hudson

Huddie is the smartest non-millionaire I know. He’s in year four as a Trading Challenge student. And he knows a lot more than he trades. In other words, I think Huddie should size up. He has enough knowledge, but he plays it very cautiously.

Keep in mind that Huddie’s made $574,176 in trading profits and over $291,000 in 2020.* So even though I’m telling him to size up, he’s doing an amazing job. See Huddie’s profit chart here.

Now for the lesson…

Lesson 8: Know When You Know What You Need to Know

The vast majority of people reading this should trade much more conservatively. You should trade small, stick with it, and stay in the game. Only size up later.

For Huddie, the time has come to size up during this crazy market. But only because of all the studying and preparation he’s done. And he has sized up, but sometimes I think he could size up more. In any case, Huddie’s on his way to being one of my next millionaire students.

The next top trader is…

Tim Lento

Tim Lento has been part of the Trading Challenge from the beginning. Not only is he a top trader, but he’s also a chat room moderator and Trading Challenge mentor. He gives weekly trading challenge webinars. (Hint: Lento’s first 20 webinars cover everything he learned in his first 10 years of trading. Watch them.)

Tim’s primary strategy is to short sell pumps for several weeks or even months. He follows the promoters as well as anyone I’ve seen.

Which brings me to the next lesson…

Lesson 9: Don’t Trust the Company, Trust the Price Action

Lento spots the pumps long before most people. He sees stocks going up too much to make sense and tries to find shares to borrow. Then he’s patient. He’s averaging roughly $140,000 per year in trading profits since 2015.*

The key lesson is that Tim doesn’t trust company press releases. He doesn’t buy the hype. And he definitely doesn’t trust the promoters. Instead, he trusts the chart and the price action.

That’s exactly why one recent loss, although big for him, didn’t turn into something much worse…

Bonus Lesson: Markets Can Stay Irrational Longer Than You Can Stay Solvent

Tim Lento was ahead of the game on the CytoDyn Inc. (OTCQB: CYDY) pump and short squeeze earlier this year. WAY ahead.

You might know that my favorite trading pattern is the morning panic. And on June 30, CYDY had one of the best morning panics of the year. SO many students banked — both shorting the crash and longing the bounce.

But Tim Lento missed it. I’m grateful to Lento for being transparent and sharing why. Again, he knew this was a big promotion. And he was so sure it would eventually tank that he took a solid short position back in March.

As he notes in his comments about the trade

“I could’ve locked in a nice profit [in April] but fell in love with the blatant scam story.”

The lesson: Markets can stay irrational longer than you can stay solvent. Had Tim Lento stayed in the trade as CYDY got squeezed all the way to $10 per share, he would’ve blown up his account.

Instead, he took his loss and moved on. He didn’t even try to trade it on June 30 because, as he put it…

“I was so mind****ed due to the loss, I didn’t reassess at $10.00 and crush the trade.”

While I feel bad that Lento missed that one, he did the right thing.

It’s time for the final top trader to highlight in this post…

John Papa

John Papa is also in his fourth year as a Trading Challenge student. Everyone goes at their own pace, but it seems like three or four years is a common time frame to find consistency. Keep that in mind as you continue your journey.

PapaJohn, as he’s known on Profit.ly, has made $227,534 in trading profits. In 2020 he’s made over $196,000.* Looking at his profit chart, it’s clear he’s another example of preparation meets opportunity.

But the lesson I want you to take away is…

Lesson 10: Take It One Trade at a Time

The market doesn’t owe you anything, and the money isn’t just there for you. When most traders lose, you have to figure out what YOU can do to separate yourself from the majority.

John Papa is a perfect example of a top trader testing different strategies and taking it one trade at a time. He often adds #OneGoodTrade to his tweets. As he likes to say, “On to the next.” I can’t wait to see how John grows over the next few years. It’s exciting times in our niche.

John Papa teams up with Matt Monaco and Tim Bohen for Small Cap Rockets alerts.

Top Trader Takeaways

You can learn SO MUCH from following all 10 of these top traders. I suggest you do so and learn something from each.

For now, here are more keys to their success…

  • Preparation: there’s no way around it. Get after it today.
  • Study the past. (Without complaining or wondering why. Just do it already.)
  • Tinker and experiment. Do I really need to explain this?
  • Get — and keep — the right mindset.
  • Use the right tools. (Use StocksToTrade and STT Breaking News Chat to find all the best plays.)
  • Learn from other successful traders. (Yep, all these guys learned from others. Including each other.)
  • NEVER follow alerts or picks from anyone else. These top traders focused on becoming self-sufficient.

(I helped develop StocksToTrade and I’m a major investor.)

Remember, all these students are now top traders. And they ALL put in anywhere from one to 17 hours per day while learning. Do you want their success? Yes? Good!

There’s no shortcut. Build your own dreams, use your own mind, earn your own money, and become self-sufficient. Do it!

What do you think of these lessons from top traders? Comment below, I love to hear from all my readers!

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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”