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Challenge Webinar Top Penny Stock Trading Lessons: 3 Top Traders Talk Rule #1

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Written by Timothy Sykes
Updated 4/19/2022 7 min read

When it comes to trading penny stocks, there’s not an infinite number of lessons to learn. The knowledge you need is finite.

But one thing you REALLY have to learn: patterns.

Like this pattern Tim Bohen discovered that happens at exactly 2 pm, several times a week…

Click Here to Join Tim Bohen’s 2 PM Cash Appointments Summit on April 21, 8 pm ET

Then there are trading rules

There’s not an infinite number. It’s about having the discipline to follow them.

Don’t get me wrong — it’s not easy. For example, you need to learn to adapt to changing markets. But at some point, it will all make sense.

And it shouldn’t take the rest of your life to learn the most important trading rules.

That’s especially true of rule #1.

It’s a simple rule.

But for many traders, it’s difficult to follow.

I say Cut losses quickly so often that I might sound like a broken record.

That’s why, when a Trading Challenge student asked us about it during last week’s webinar, I made sure we all answered.

My hope is that by understanding why it’s so important…

The MOST important rule for me and ALL my top students…

It will finally sink in. Check it out…

The #1 Penny Stock Trading Lesson EVERY Trader Should Know…

Rule #1 is so important that I want you to know the pain we felt NOT following it. Let’s do this…

3 Top Traders Talk Rule #1: Cut Losses Quickly

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Thanks to Trading Challenge student SuzyQ, who asked…

“Question for all three of you: Did you ever have trouble cutting losses quickly, and how did you overcome it?”

Penny Stock Trading Lesson 1: Matt Monaco’s Take On Rule #1

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Matt’s experience reflects a lot of top traders. Here’s what he had to say…

“Eventually, you’re gonna take a loss that’s so bad that you’ll never want it to happen again. Pain is the best teacher.

“Back in 2020 … I think it was late February or early March when I took a big smack … it was something like a $6,000 loss. It put me back below PDT, and it was my low point. 

“But it forced me to be disciplined. And by April, I had my first-ever five-figure month.” 

I remember when Matt took that loss. The most important thing was getting himself back on trade and vowing to be more disciplined.

Penny Stock Trading Lesson 2: Bryce’s Near-Disaster Shorting a First Green Day

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For Bryce, it wasn’t even taking the loss so much as experiencing that sickening feeling. He went from up big in a trade to nearly blowing up. Check it out…

“I never had an ego, but there was a time I tried shorting a first green day,” Bryce says. “At one point, I was up something like $100K unrealized. I kept adding and adding. All of a sudden, it started to squeeze. I found myself down $11,000. 

“Again, I was shorting a first green day that was on the verge of a breakout. That scared me into respecting my trading plan.”

A good lesson and a bullet dodged. I wasn’t as lucky as Bryce…

Penny Stock Trading Lesson 3: Why Cutting Losses Quickly Is Rule #1

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Matt was right about the pain of a big loss. And I’m sure he heard it from me at least 50 times…

If you have trouble cutting losses, eventually you’ll take a loss that’s SO bad you’ll never want to feel that way again.

For me, it was a $500K loss on Cygnus e-Transactions. It’s a long story…

Download my book “An American Hedge Fund” here at no-cost.

It’s the least I can do to try to drive home the point. In the book, I wrote about the entire painful experience of being stuck in an illiquid penny stock.

For the purpose of this post, let’s just say that single trade made me want to teach people how this industry really works. It was painful, but it was my best teacher and changed my life for the better.

More Top Penny Stock Trading Lessons

Tim Sykes tosses his book An American Hedge Fund in the Alps
© Millionaire Media, LLC

Every week I give a Trading Challenge webinar. They alternate between Q&A sessions and live-trading webinars.

Over time, lessons from webinars compound to grow your knowledge account. Come with questions and work to get better at trading penny stocks under $1.

5 More Penny Stock Trading Lessons

Miss the webinar? Trading Challenge students can watch part 1 here and part 2 here. Here’s a taste of what you’ll learn when you watch the replay…

  • Why Bryce FORCED himself to trade his way over the PDT even though he had enough cash. (Shocking but true and SO important if you want lasting success.)  
  • Why YOU must make the decision to study. (Seriously, if I have to convince you to study, there’s not much hope.)
  • Why it’s true that money changes you, but not in the ways you think.   
  • How the Tim Sykes NFT Club is designed to weed out undedicated traders. Not everyone agrees, but I’m sticking to my decision.
  • PLUS: Why I have so many movie references — and what, exactly, it has to do with trading. (And the weird reason it has served me well…)

There were dozens more lessons during the all-day webinar. I can’t encourage you enough to show up every week with solid questions.

Ready to take your trading to the next level? To access the live webinars and hundreds of archived webinars…

Take the Trading Challenge

Live webinars separate the Trading Challenge from our stand-alone products and newsletters. Every week there are two to four live webinars from mentors like Tim Lento, Mark Croock, Matt Monaco, and me.

Want more penny stock lessons from Trading Challenge webinars? 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

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* 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 (205) 851-0506 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”