My Greatest Trading Challenge Student Roundtable to Date

By Timothy Sykes

Last updated on April 18, 2022
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The timing couldn’t have been more perfect for my recent Trading Challenge student roundtable.

This live Q&A session was a collaboration with TWIST (“This Week in SteadyTrade”), a podcast hosted by Trading Challenge moderators Jack Kellogg, Matthew Monaco, and Kyle Williams. We also invited Mike ‘Huddie’ Hudson and Dominic Mastromatteo along for the ride.

I knew it was gonna be a great webinar … I had no way of knowing just how perfect the timing would be.

We recorded during the week of January 25, 2021 — the height of the GameStop Corp. (NYSE: GME) madness. Plus, more than one of these students reported a big milestone the same week!* (You can check that out in a bit.)

Seriously, I couldn’t have planned it better. It was the perfect time to both celebrate these traders’ achievements and offer important lessons about this insane market…

But I need to make this very clear … These students are having their moment after YEARS of hard work.* 

They’ve all had the experience of watching a hot market from the sidelines while learning and taking small positions. They spent years investing in their knowledge accounts. When the market started to heat up in 2020, they were ready.

They were patient and they persevered and now their hard work is paying off for them.

There’s a LOT to learn from this Challenge student roundtable. All of these traders have different stories. None of their strategies are exactly the same. Learn something from all of them…

(*Note that these results aren’t typical. These top traders and I 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.)

A Live TWIST/Trading Challenge Student Roundtable for the Ages

On January 27, 2021, I was joined by a star-studded cast of Challenge students turned top traders to record an epic TWIST/Trading Challenge student roundtable.

You can check out the full recording here:

But don’t stop there. Be sure to check out the other episodes of TWIST, too. They do interviews with other upcoming traders and discuss specific trading strategies. It’s an incredible NO-COST resource.

While they’re not TWIST hosts, both Dominic and Huddie have been featured on previous episodes. Check out Dominic’s episode here and Huddie’s episode here.

If you’re not already following the crew on social media, take a break to add us all to your feed right now:

The Week of January 25, 2021: An Epic Trading Week

I had no way of knowing what kind of trading week of January 25, 2021, would be. Nobody did.

We recorded this Challenge student roundtable at the height of the epic GameStop short squeeze. It’s over now, but there are still important lessons to learn from it … Check out my full blog post on it.

At the time we were recording, several brokers had put buy restrictions on GME and other hyped-up stocks like and other stocks like AMC Entertainment Holdings Inc. (NYSE: AMC).

It was NOT a normal trading week. Unprecedented events were happening left and right.

That particular craziness may be over, but the current market is definitely not what I’d call ‘normal.’

It’s a crazy bubble market right now. There are opportunities, yes. But it’s also more important than ever to be responsible, play by the rules, and CUT LOSSES QUICKLY.

Five Traders, Five Insane Trading Weeks

All the traders in this Challenge student roundtable have spent years studying and preparing for a market like we’re in right now. Here’s what was going on with each of them at the time we recorded…

Mike ‘Huddie’ Hudson

For a long time, Huddie was mainly a short seller. But when crazy OTC trading opportunities came along, he decided to adjust his strategy.

He hit up Dom for some advice about going long on OTCs. He adapted and refined his new strategy — and he’s mainly been going long in 2021.

It’s been working for him. If you look at Huddie’s chart, you’ll see that he’s had impressive exponential growth* recently. I think a big part of that is his willingness to adapt.

Jack Kellogg

There’s no other way to put it — Jack Kellogg is killing it. He’s up nearly $5 million in total trading profits as of February 10, 2021.*

Compare that to a year ago. As of February 8, 2020, he was up about $188K in profits.*

It just goes to show what happens when you focus on studying and refining your process and then finally, the right market conditions come. As he says in the webinar, “We wanted this market and we finally got it.”

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He recognizes that his preparedness is what has led to his growth. A year ago, the idea of a six-figure week was like some sort of dream to him. Now, as of early February 2021, he’s already up nearly $3 million in profits for the year.*

That’s insane. That is NOT a common story for any trader. But you know what I love about Jack? He stays humble. He talks about how his mission every day is to show up and do his best.

Dominic Mastromatteo

Ever since Thanksgiving 2020, Dominic has been focusing on sizing up.

Previously, he was comfortable risking “$200 to $300.” But seeing Jack’s growth, he got inspired to size up and start taking some calculated risks.

He’s also making an effort to focus on three to four plays per day versus getting “scalpy.” That way, Dom says, he can take a bigger size on a few plays versus trying to chase everything.

It’s tempting to chase. But don’t underestimate the value of being calculated in this market and capturing the meat of the move…

Matthew Monaco

What a difference a year makes! In January 2020, Matthew actually lost money. Just look at his profit chart. On the day we recorded, he reports he passed the million-dollar profit mark.* He’s come a long way since we collaborated on my 30-Day Trading Bootcamp!


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Like many of the others in this Challenge student roundtable, Matthew’s been trading OTCs lately, too. He’s mainly focusing on breakouts and dip buys. But when he sees an opportunity with a listed stock, he doesn’t avoid it.

No matter what he’s trading, he says that his plays are “straight out of ‘PennyStocking Framework.’” Lately, there have been multiple trades a day and singles add up

Kyle Williams

Kyle also passed the million-dollar profit mark the week we recorded!*

Like Huddie, Kyle has traditionally identified as a short seller. But that’s been changing recently. Why adapt? “Short selling this month has been quite painful,” he says in the webinar … That trend doesn’t appear to be changing now that it’s February.

Don’t miss this video I made about the dangers of short selling right now…

As I wrote in a recent post about Kyle’s crossing the million-dollar mark, he’s primarily focusing on going long in 2021.* Mostly OTCs, but the week we filmed, he was going for some listed stocks too.

His ever-adapting strategy is paying off for him — as of February 10, 2021, he’s up over $214K in profits for the year.*

How Years of Study Can Pay Off

Before you start getting visions of millions dancing in your head reading about these traders … you must know something important.

They’ve all been trading, practicing, studying, and refining their strategies for YEARS.

People get excited by the dollar amounts, but too many fail to understand that these impressive stats did NOT come overnight.

Stories like this are NOT common.

For instance, people love hearing how I turned roughly $12K into $6 million and counting as of February 2021.* But that didn’t happen right away. I’ve been in the penny stock game for 20+ years.

Don’t know my story? Check out my autobiography “An American Hedge Fund” for no cost. You’ll see just how hard-earned my millions truly are*…

All of the traders I talked with in this Challenge student roundtable have had exceptional results with their trading.

But all of them have also put in exceptional effort to get to where they are now. And it did NOT happen overnight:

  • Mike ‘Huddie’ Hudson started trading in 2015.
  • Jack Kellogg started trading in 2017.
  • Dominic Mastromatteo joined my Trading Challenge in 2016 but didn’t place his first order until 2017.
  • Matthew Monaco started trading in 2017.
  • Kyle Williams started trading in 2016.

They’re benefitting from the craziness of the market now … But that’s in a large part thanks to all of the behind-the-scenes hard work they put in during the weeks, months, and years since they all started.

Trading Challenge Student Webinar: Top Lessons

Tim Sykes studying and trading
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Here are some of the most important takeaways from this Challenge student roundtable…

Becoming a Millionaire Isn’t the End Goal

In the webinar, all of my Trading Challenge students reflect on how, a few years ago at my conference, they were all wishing they could become millionaires.

But once traders cross that milestone, they tend to realize it’s not the be-all, end-all.

By the point they’ve made a million dollars, they’ve been in the game long enough to prove that they have a passion for the process.*

Money isn’t their primary motivation anymore — it’s a love of trading and a desire to keep learning and getting better.

Don’t get me wrong, I love that several of my students have become millionaires.* But at the same time, it’s important to emphasize that it shouldn’t be any trader’s primary motivation!

Level Up Your Friend Group

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

I’m constantly talking about how trading is a bloody battlefield.

It’s much easier to survive if you have some good soldiers on your side.

This whole crew came up together. They’re all friends. We’re all friends. We hang out.

We talk about trading and share information. I share everything about my trading publicly … So do many of my students.

Just about all of the traders in this webinar help with my trading education business in some way — whether it’s hosting webinars, moderating the chat room, or taking part in a live trading event…

Learn from all of us. Trading is better with a community.

Learning from a variety of traders helps you build a strategy. For instance, I don’t trade options, but my student Mark Croock does. Since he’s adapted his options strategy from my penny stock trading strategy, you can potentially expand your trading knowledge by learning from him.

Remember: you’re the average of the five people you hang out with the most.

As Matthew says in the Challenge student roundtable, “I’m with five incredible people right here, and it’s a huge reason why I’m so successful. I’ve taken everything from everyone on this call and I’ve just put it all together. So level up your friend group.”

Good Habits Matter

I need to give a warning to all of those gunslingers out there in today’s hot market…

It’s not gonna last forever.

Unfortunately, I see a lot of people making money with the wrong attitude and mindset right now. I see traders:

  • Going all in.
  • Using leverage.
  • Betting on parabolic moves.
  • Not selling.

Right now, I see people being rewarded for a lack of discipline. I appreciate that they’re making money, but it’s more important to stay disciplined.

It will end. I don’t know when. But when it does, I’m gonna stay safe. They’re gonna get annihilated.

It’s not about making as much bank as possible in a short period. It’s about doing it in the most disciplined, sustainable way.

Good habits are boring but they can help keep you in the game for the long haul.

You Must Adapt

I talked earlier about how Huddie and Kyle adapted from mainly short selling to going long because that’s what’s working in the market right now.

Things change in the stock market. Sometimes the changes are gradual. Sometimes they’re fast.

Either way, you’ve gotta adapt if you want to survive. 

The good news here is that what you’ve learned in the past still matters. It can still inform your trading decisions. For example, a lot of traders continue to use the lessons I teach in my DVDs

When asked about tips for new traders, Huddie didn’t hesitate: “Watch ‘Trading Tickers.’ Watch ‘How to Make Millions.’ Watch ‘PennyStocking Framework’. Watch those three DVDs like they’re your bible, like they’re your textbook. It took me like a year to watch ‘Trading Tickers’ and that was a big mistake.”

Don’t make Huddie’s mistake — check out ALL of those DVDs! And check out top trader Tim Grittani’s long-awaited follow-up DVD, “Trading Tickers 2.”

Learn more about the original “Trading Tickers” in this video:

Are You Ready?

In addition to my vast library of DVDs, I’ve got thousands of video lessons — many are available at NO COST on YouTube.

There’s no excuse for being uneducated in the stock market…

This Trading Challenge student roundtable seriously cannot be missed.

These traders have been in the game for a while now. They’ve gained a lot of knowledge the hard way — take advantage of it! Learn from them. Who knows, it could speed up your learning curve.

Listen and learn from these students. Discover their strategies and when and how they started scaling up … Find out how they’ve changed over time.

It just goes to show that EVERY trader is different! I want this Challenge student roundtable to show traders that there are SO many different paths you can take in the stock market.

Finally, heed my warning … Take this market seriously. Not in terms of how much money you can make but in terms of how many lessons you can learn.

Every trade is a lesson — wins, losses, selling too early, even holding and hoping. It all can help you adjust and do better.

Ready to study and learn? Consider applying for my Trading Challenge.

What was your favorite lesson learned from this webinar? Leave a comment below.


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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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