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3 Trading Lessons From 3 of My Top Students

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Written by Timothy Sykes
Updated 1/4/2023 11 min read

The 3 trading lessons you’ll find in this post apply not only to trading but to living a powerful life. In other words, they’re not technical trading lessons. They’re big-picture lessons. And they’re important if you want to become a self-sufficient trader.

I often talk about the nuances of trading and being meticulous. And being meticulous is crucial. But these 3 trading lessons are meta.

I’m SO proud of top students Matthew Monaco, Kyle Williams, and Jack Kellogg. These guys have worked their butts off to become self-sufficient. And they’ve done it by applying these lessons to trading…

3 Life Lessons Applied to Trading

top penny stocks list Tim Sykes on a cliff in Italy with a laptop
© Millionaire Media, LLC

In many ways, trading is a microcosm of life. There’s an old adage …

“How you do one thing is how you do everything.”

If you think about it, that’s pretty accurate. So if you’re a truly dedicated trader, pay attention to these 3 trading lessons. Matt, Kyle, and Jack did…

Trading Lesson #1: Get On the Right Path

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All three of these young traders are on the right path. They’re focused on, and immersed in, the process. Look at their profit charts on Profit.ly:

They’re all perfectly uptrending. All three of these guys are passing milestones. But most importantly, they have the right mindset…

It’s Not About Luck

I get DMs and emails from people saying, “If you’re such a good teacher, why do you have so few millionaire students? Your millionaire students just got lucky.”

No. These guys are proof that trading success is the result of thousands of trades added up. The harder they work, it seems like the luckier they get, right? But they wait for the best patterns. They put themselves in the best trades with the best odds for their strategies … and then let the odds play out.

Sometimes they’re right, and sometimes they’re wrong. But they’re right more often than wrong. And they know to cut losses when they’re wrong. That’s how their dollar wins are bigger than their dollar losses.*

(*Trading is not an exact science and students’ results aren’t typical. These students put in the time and dedication and have exceptional skills and knowledge. Most traders lose money. Always remember trading is risky … never risk more than you can afford.)

Need proof these traders are on the right path? Jack Kellogg hit $1 million in trading profits on November 5.* It’s pretty crazy. He joined the Trading Challenge in January of 2017.

Kyle Williams and Matt Monaco aren’t millionaires yet. But they’ve both made multiple six figures in 2020.

The Statistics of Trading Success

This is simple … but not easy.

If you win more often than you lose, and your average loss is smaller than your average win, it is statistically impossible not to grow your account.

Assuming you stay on that path.

All three of these traders are on that path. They’re at different places because everyone has their own path. For example, Jack likes to get a little more aggressive. That’s why he’s my newest millionaire Trading Challenge student.*

But all three are on the right path.

Trading Lesson #2: Rewards Come With Hard Work

I love to reward my top-earning students. And that was their first private jet ride. (Videos coming soon, we had a great time.)

Use this as inspiration: I like to reward millionaire Trading Challenge students.

For example, when Tim Grittani first passed $100,000 early on, I took him to the Maldives. I didn’t have any millionaire students back then — at $100K he was one of my top students.* But that was his first overseas trip…

The Ultimate Maldives Private Beach Dinner

I hope that inspires you to work hard.

Another example is Roland Wolf. When Roland first passed $100,000, I took him to Italy. We made this video — which has at least 3 trading lessons. One of the most important trading lessons is at the 3:10 mark…

My Student Roland Who Turned $4,000 Into $170,000 in 7 Months

Roland passed the $1 million milestone this year. Tim Grittani has made over $13 million in total profits and roughly $3.4 million this year.* We’ll see how far these guys go. The lesson is…

Once you get on the right path and learn to grow your account one trade at a time, you can crush big profit milestones. Then — and only then — do you get the rewards.

Trading Lesson #3: Be Mindful of Losses

Kyle, Matt, and Jack are all on the right path with the right mindset. But one of the big reasons for their success is they’re all very mindful of losses. 

This is the most important of the three lessons specific to trading.

Read my recent post “The 2 Biggest Trading Risks Right Now.” It explains how these guys manage risk.

One of the biggest risks as a trader is not taking small losses. So Matt, Kyle, and Jack don’t feel like they have to be right. They don’t have that ego.

They’ve all learned, through their own experiences and studies, that it’s not about ego. They’ve learned it’s OK to be wrong if you limit your losses. What’s the best way to limit your losses? Follow rule #1: cut losses quickly.

If you lose $100 or $200, who cares? Especially if you’re learning the right lessons. The problem comes when you lose $5,000, or $10,000. Or even $50K. Or, for example, my biggest loss of $500,000…

Not only does a big loss set you back in terms of wealth, but it also plays mind games with your confidence. See how I overcame my biggest ever loss in my best selling book “An American Hedge Fund.”

When you lose confidence it spells trouble because…

Trading Is a Very Fragile Thing

If you take a big loss like that, you can start seeing patterns that aren’t there. You can be tempted to try to get back to where you were before. If you lose the ability to say, “I don’t need to trade, I’m going to wait for my patterns…”

That’s a slippery slope.

But it happens. Once you start losing you say, “I gotta get it back!” And then you start trying to cheat the system. So you take subpar setups on subpar patterns. You think you can get back.

Sadly, sometimes you do get back … but you learn the wrong lesson.

You don’t want to fall down that slope. It’s almost like you have to remember ahead of time. Learn these 3 trading lessons from these 3 top traders. You can be wrong on any trade. Small losses are fine.

But don’t go down the slope of losses combined with a lack of discipline. It gets ugly.

So, how are these three top students all on their way to becoming millionaires? First, they study their butts off. They don’t need me any longer.

Follow the Recipe

I can’t wait to see where Jack, Matt, and Kyle go in the future. Yes, that was their first private jet ride — and we had an amazing time. My question is … who’s next? Who wants it the most? And who wants to get on the right path — not just the millionaire train.

The recipe is NOT zero to $1 million.

First, you gotta find consistency. Then you need to pass $300,000 … $500,000 … and $900,000 on the way to $1 million. 

It might not seem like it matters. But that kind of nuance is really important. Some people reading this will think, “OK, Tim, I get it. You gotta make six figures before you make seven figures.”

But you need to get on the right path. You must learn to be mindful of losses. And it’s key to focus on the process and work hard to get the rewards later. Delayed gratification is essential.

For all those asking about how many millionaire students I have…

This is a process I’ve taught many times before. I don’t just have one or two millionaire students anymore. I have half a dozen. In a year or two, I could have a dozen — it’s growing very fast. Yes, it’s partly because of the hot market. But it’s also because I’ve gotten better as a teacher and I have a specific recipe for students to learn the process.

It’s not an exact science. But we know the process. We’ve seen it enough times now. We’ve watched where students do well and where they go wrong. But we can’t make the students do the work.

You have to figure out what patterns work best for you. You have to gain experience.

Trading Education Resources

Learning to trade penny stocks isn’t rocket science. But fair warning: the stock market is a battlefield. Ask any of the traders mentioned in this post and they’ll tell you. We all have stories of licking our wounds after trades gone bad. It’s part of the game.

That means you MUST have the best tools, the most knowledge, and as much experience as possible. There’s only one way to get experience — stay in the game long enough to find consistency.

But to do that … you need to start with your education and trade small. With that in mind, the information in these resources is essential.

  • If you’re brand new to penny stocks, start with my FREE penny stock guide.
  • Read “The Complete Penny Stock Course” by my student Jamil.
  • Go through the 30-Day Bootcamp. Hint: You get lifetime access, so 30 days is just the suggested time to complete it. And… Jamil’s book is one bonus that comes with the 30-Day Bootcamp. Learn more about the 30-Day Bootcamp here.

If you’re ready to immerse yourself, apply for the…

Trading Challenge

Every student mentioned in this post is a member of the Trading Challenge. They’re also moderators in the Trading Challenge chat room. In other words, as a Trading Challenge student, you can interact with them — live — every day. (Please follow the chat room rules.)

The Trading Challenge is like the complete cookbook. It’s everything I’ve learned in 20+ years as a trader and 12+ years as a teacher. From video lessons to webinars, watchlists, trade commentary — it’s all there. Could you be the next millionaire student? Apply for the Trading Challenge today.

Give Matt, Kyle, and Jack some love in the comments below. They’re perfect examples of the 3 trading lessons in this post. 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”