timothy sykes logo

Success Stories

Meet My Newest Six-Figure Trading Students

Timothy SykesAvatar
Written by Timothy Sykes
Updated 4/17/2022 11 min read

Dominic, Jack, and Kyle all presented at this year’s annual conference. And they were all once my trading students (You can watch their conference presentations here: TISummit 2019 DVD presale.)



Jack Kellogg, Dominic Mastromatteo, Kyle Williams, Timothy Sykes photo courtesy of Don Mash
left to right: Jack Kellogg, Dominic Mastromatteo, Kyle Williams, Timothy Sykes – photo courtesy of Don Mash

Keep in mind these guys worked their asses off to get where they are. Their results are not typical. Read on to find out how they became self-sufficient traders.

Jackaroo Wears His Chain Outside His Shirt

So I posted a video on Twitter with these three guys. I asked them if they had anything to say about their success. When I got to Jack and how much he’d made, I asked him why he wears his chain on the outside. (I was ribbing him about it all weekend.)

So I asked Jack if he was a fan of the movie A Night at the Roxburystarring Will Ferrell and Chris Kattan.

What happened next blew my mind…

These Three Traders Are So Young

Post image

Get my weekly watchlist, free

Sign up to jump start your trading education!

NOT ONE of them knew the movie. Seriously.  Dom didn’t recognize the reference. And Kyle and Jack hadn’t seen it either.

I love it!

The movie came out in 1998. So I’m like, “What! Really?”

Check out the tweet:

Even though we all look alike, they’re benefitting from my 20 years of experience. Thanks to the Challenge, they’re skipping a ton of frustration and confusion. And that’s what it’s all about.

How Dom, Jack, and Kyle Became Self-Sufficient Trading Students

Self-sufficiency. It might be one of the most important differences between what I teach and what the fakes teach.

All three of these young traders are self-sufficient now. That doesn’t mean they’ve stopped learning. By my standards, they’re all still newbies. But they know when they’ve made a mistake. They understand my basic rules. They each have a pattern or setup they know is their bread and butter. They’ve learned to cut losses quickly.

Dom and the OTSwizzle

Dom gave an in-depth presentation covering everything from risk management to building the story of a stock chart. He talked about what he wished he’d known from day one. And he spent time on the quickest way to profitability.

Here are some key points from Dom’s presentation:

  • Begin by studying the Trading Challenge materials. Make sure you understand all trading vernacular. Spend at least two months on this.
  • Watch every DVD and video lesson. Pay attention to the patterns that make the most sense to you.
  • Trade for one to three months using the setups that make the most sense. Track every trade.
  • Figure out what setups work for you — based on the actual numbers.

That’s just one small part of Dom’s killer presentation. He also explained his favorite setup which he calls the OTSwizzle. (Dom, are you sure you haven’t watched that movie? Because OTSwizzle sounds like something the Butabi brothers would say…)

Check out this tweet of Dom’s closing remarks posted by his dad, Don:

I suggest you get the DVD and watch it several times. Also, join the Trading Challenge. Or if you’re not ready for the Challenge, subscribe to Penny Stocking Silver.

When you get the DVD, be sure to take notes when you watch…

From “The Big Short” to the Orlando Stage — All While Still in College

Kyle talked about the difference between trading OTCs and listed stocks. He said that even though he’s learning about listed stocks, a majority of his gains are from OTCs. He talked about working on the risk vs. reward with listed stocks.

Take a look at Kyle’s profit chart here. It’s impressive. Kyle lost consistently for nearly a year from when he started in July 2016. And from his low in May 2017, it took another six months to get back to break even. From break even to getting over the PDT was another 10 months! 


Kyle first got interested in trading penny stocks after watching The Big Short.” So at least I know he watches movies…

Jack, on the other hand, just likes to wear his chain on the outside of his shirt and play video games when he’s not trading. But he’s a badass young trader so I’ll forgive him…

“Please, NO!” Jack’s Turtle Beach Confession

Jack had one of the best receptions of the entire weekend. And I think it’s because he told all about his worst ever loss on Turtle Beach (NASDAQ: HEAR). He went deep into the feelings he experienced during the trade. And how he managed to cut losses intelligently on advice from Tim Grittani.

Jack also talked about his favorite setups, like first green days and panic dip buys. And, he also covered trader mindset tips. It was especially cool — and gratifying — to hear him talk about transparency.

Check out this recent interview I did with Jack and Dom. Their insight at such a young age is inspirational. Learn it, live it, love it:

When They Were Busy Being Born, I Was Making My First Million

That’s so weird — but I love it.

I’m so proud of these guys. Not just for the money they’ve made, but for the incredible focus and dedication they’ve put into the process. They all talked about spending hours immersed in studying. And each of them had to learn to lose well before they became consistent.

Trading Students: The Challenge

All three of these guys are members of the Trading Challenge. All three talked about the importance of the community, of networking with other traders, and soaking up EVERY SINGLE DVD … VIDEO LESSON … AND WEBINAR!

They didn’t try to cut corners. They all got where they are by working their asses off. When you make the decision right now to join the Trading Challenge, you’re one step closer. If you’re accepted, you’ll get access to EVERYTHING Dom, Jack, and Kyle used to become self-sufficient. Plus, you’ll see them in the Challenge chat room every day.

You want this? Go for it. Even if you’re too young to know A Night at the Roxbury.”

© 2018 Millionaire Media, LLC

What TISummit Attendees and Students Are Saying

More from TISummit attendees and students:

From @SublimeTrades (another up and coming badass trader):

And @NeilSaintJean1:

Or this from @RouxBourbon:

And this tweet yesterday from @TraderTrav81:

Recent Comments From the Trading Challenge Chat Room

Crypto_M → timothysykes: “I joined the challenge the day after the conference. I studied the first 2 dvds last week. This week I have been studying and watching the markets on TOS all this week. I was BLOWN away at how fast things move. I played college football and understand the speed difference from high school to college and then to the pro’s. I am excited to study more to get my mind right for the speed of this PRO market. Thanks for cataloging your trading for guys like me to learn.”

Just to show how hard Crypto_M is working … check this out:

Crypto_M → timothysykes: I know that some of you will think this doesn’t matter but I have only been in the challenge for 2 weeks and have studied about 10 dvds. Today was my first paper trade. I took 1000 of $TTNP at .41 when it broke the HOD. My RR was.03 and Return .08. Needless to say the trade worked out just as Tim teaches. In at .41 out at .48”

Crypto_M, it does matter. Keep studying and practicing. And remember, it’s a marathon and not a sprint.

How about this recent win from Kyle…

Kylecw2: “all covered $CVSI for $800 not enough range.”

More Challenge Chat Room Comments

the_tipsy_nomad: “Quick 5% gain on $SPNV for $300 profit. Not bad for a 10min hold. Not getting greedy, taking my single for the day.”

somsakun555: “Yeh!! sold $SPNV almost 20% gain from dip buying, 0.38 to 0.448. Give me some more hope of a day trader career after many losses. Thank you everybody for all your guidance.”

jvjtrading: sold .47 $TTNP from .37. 25% win. to bad it was only partial fill.”

SatelliteIncomeUnlimited: “$ADXS 217.00 profit.. sold at the break out, bought around .388 sold in to .4099.”

scottsaylor11: “Very nice on $clsi. I couldn’t help but lock it all in .077 from .0675. +240.”

Plus This Awesome Comment From the TimAlerts Chat Room

vnickn: “$SRNE short at 2.77, covered 1.87… good thing I decided to check my E*TRADE app at a red light. Had to pull over to close that trade… +2700.”

What’s your take on Jack, Kyle, and Dom’s success? What inspiration can you get from their stories to help you become a better trader? Comment below, I love to hear from all my readers! 

How much has this post helped you?

Leave a reply

Author card Timothy Sykes picture

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”