timothy sykes logo

Trading Tips-Tim Sykes Penny Stock

5 Lessons With $8 Million Trader Jack Kellogg

Timothy SykesAvatar
Written by Timothy Sykes
Updated 10/12/2021 10 min read

5 Lessons With $8 Million Trader Jack Kellogg: Key Takeaways

  • Jack pushed himself to the max — he couldn’t have done better the past year.* Read on to find out how he did it.
  • Every setup has its limits. Know when to push it, and when to cut and walk away.
  • PLUS: Jack’s BIG tip for how he plans to trade the next hot market. (Hint: watch the video…)

Trade with Jack, Kyle, and Mari

In August, I met up with six millionaire students in Italy. During the week I caught up with Jack Kellogg. In the eight months since we’d last talked, Jack had made an almost unheard-of (for penny stocks) $6 million in profits.*

Check out the video below. Then keep reading, because Jack also shared five lessons he thinks every new trader should learn…

Jack Kellogg’s Tips to Over $8 Million in Profits In 4 Years

jack kellogg and sykes in italy
© Millionaire Media, LLC

In this video, you’ll learn…

  • How Jack maximized during the hot market — including the strategies he used.
  • The strategy Jack used to make over $1.3 million in one week.* (And how he took his biggest ever loss the same week by breaking one of his own rules.)
  • What Jack learned from video games that helps him manage dozens of trades at once.
  • Jack had to relearn THIS after pushing it harder than any trader I’ve ever seen. (And the price he paid for it.)
  • How much Jack made on his biggest trade. Most people don’t make this much in a year.
  • The story behind Jack’s first visit to an AMC theater. (Bet you can’t guess what he bought…)

Hopefully, that inspired you to study. Let’s do this…

5 Lessons With $8 Million Trader Jack Kellogg

I teach students to start small and focus on the process. When I asked Jack if he had five lessons to pass on to new traders, he didn’t hesitate. His first lesson is…

Risk What You’re Willing to Lose

Post image

Get my weekly watchlist, free

Sign up to jump start your trading education!

In Jack’s words…

“For people starting out, I think that’s a big thing. A lot of people go into the markets and they go too big without enough knowledge. They just take themselves out of the game. It’s such a common error I see over and over again. 

“People don’t really start small unless it’s pushed into their heads. Too many people see trading, open an account with $3,000, put it into a few stocks, and that’s it. 

“If you took that $3,000, bought yourself some trading education, and started with $10 risk … you’d have a much greater chance of being successful.”

I agree with Jack 100%…

Jack’s next lesson is about something I think would change the entire industry if everyone did it. Here’s Jack’s take…

Be Transparent

jack kellogg on farm
Photo courtesy of Jack Kellogg

“Being transparent is very important. It can help you keep from making the same mistake again. 

“For instance, I know someone who made $100,000 in the hot market from a $10,000 account. Then he put his entire account into Tilray Inc. (NASDAQ: TLRY) when it dipped from $70 to $30. He bought the first green day at $32 with his whole account. 


  • He didn’t tell anybody he was doing it. 
  • He didn’t have a plan.
  • And he wasn’t transparent about it. 

“He ended up holding it. He’s still holding it now. (Tim here. As I write, TLRY is in the $10s.) He doesn’t tell anybody how much he’s down. And that means he’s doing it in the dark. Being transparent keeps you honest with yourself. 

“If you’re honest with others, you’ll be honest with yourself. Personally, if I mess something up and tell somebody, it’s embarrassing. But I won’t make the same mistake again because I don’t want that feeling.

“If I made a mistake in the dark, and didn’t tell anyone, I’d probably make that mistake again. So, for me, I like to be transparent. I think if this kid was transparent, he wouldn’t have made that trade.”

The story didn’t have to end that way. There were multiple opportunities to get out of the trade for a small win or loss.

If the trader Jack is talking about got out today, his account would still be up roughly 200% from where he started. As it is, he’s waiting for TLRY to bounce. That’s just crazy. He’s missing SO much opportunity — not least of which is the opportunity to learn and refine his skills. Hold and hope is not a strategy.

Here’s Jack’s next lesson…

Don’t Add to Losers

Like all top traders, Jack takes losses. Sometimes it takes a big loss to learn a big lesson. I remember watching Jack on stage at my 2019 conference, and one of his rules was never add to a loser.

Jack’s biggest loss ever was on Medmen Enterprises Inc. (OTCQX: MMNFF). On that loss, he broke his own rule…

“On MMNFF, the problem was that I just went too big on it. I was making too much money and winning too much. I had something like two million shares and it was over a million-dollar position in an OTC

“When it didn’t bounce right away, I averaged down. It ended up being a situation where I had to take a loss. So it was a matter of trying to cut intelligently. 

“I wanted to get out at 60 cents a share, but there just wasn’t any liquidity. So I lost something like $200,000 in slippage, just trying to get out.” 

I want to thank Jack for being so open about his loss. His transparency means everyone can learn from the trade. It also highlights one of three common mistakes traders make when dip buying too early.

Here’s Jack’s fourth lesson…

Long Is Better Than Short

Again, I couldn’t agree more. Short selling is a flawed strategy right now. For newbies and anyone with a small account, it’s dangerous. Here’s what Jack says about it…

“Longing is superior because you can only lose 100% of your money. With short selling, you could lose 500%. 

“And there are a lot more fees involved with short selling. With longing, it’s commission-free on Nasdaqs now. 

“Plus the SPY (S&P 500) is on a massive tear, so short selling is very difficult. For example, all the short sellers on Tesla (NASDAQ: TSLA) keep saying it’s a short. But it just keeps going up. 

“With longing, you have the chance to make so much more without as much risk.”

Here’s Jack’s fifth lesson…

Start With OTCs

Again, I couldn’t agree more. Personally, I find OTCs easier to trade for a couple of reasons. First, they don’t trade after hours and any premarket trading is very small.

Second, with OTCs you can read Level 2. Listed stocks are usually a lot more choppy, so you have to focus on the chart more than Level 2. Here’s what Jack had to say…

“I’m focused on OTCs because Nasdaqs have been giving me a headache. They’re just harder for me personally. Kyle is very into them right now and doing very well with them. I’d just rather focus on OTCs.”

Tim here. I get that some traders prefer listed stocks. And that’s one of the advantages of Jack’s chat room…

Breakouts & Breakdowns

jack kellogg and tim sykes
© Millionaire Media, LLC

It’s very satisfying having so many millionaire students now. And one of the best things is watching them give back to the community.*

Jack, Mari, and Kyle moderate the Breakouts & Breakdowns chat room on StocksToTrade.

Jack says Breakouts & Breakdowns is special because they focus on the entire 7-step framework…

“We trade the entire framework of hype. A lot of other chat rooms focus on one thing. Breakouts & Breakdowns tries to capture the full supernova. From the first breakouts, all the way to the top, and then shorting all the way down. And buying the dip, buying the first green day.”

He also gave props to his partner, Mari.

“Not many chat rooms have a female millionaire trader as a moderator. That separates us.”

Breakouts & Breakdowns is an add-on subscription for StocksToTrade. I can’t recommend it enough. Learn more about Breakouts & Breakdowns here.

Which of Jack’s 5 lessons helps you the most today? Comment below — and congratulate Jack on his massive year! 


*Results are not typical. Results are not typical. Always do your own research as trading is inherently risky. You should not mirror the trades or alerts of the instructors and attempts to do so may result in substantial financial loss. Past performance is not an indicator of future results. I’ve also hired Jack Kellogg, Kyle Williams, and Mariana Hincapie to help in my education business.

**Tim Sykes has a minority ownership stake in StocksToTrade.com.

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”