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Trading Lessons

How An 8-Figure Trader Bounced Back From Losses

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Written by Timothy Sykes
Updated 4/20/2023 6 min read

Jack Kellogg has made over $10.5 million in trading profits over the last two and half years.

However, it wasn’t always smooth sailing.

In fact, Jack lost $2600 his first year trading. And it took him twenty months before he had his first solid green month.

Of course, he’s had some massive wins…but it’s the losses that have given him the most valuable lessons.

I had a chance to sit down and talk with him about some of those devastating losses and he used them to improve holes in his trading and take it to the next level.

Here are five invaluable lessons he learned after taking some of his worst hits.


#1 Admit When You’re Wrong And Bail

jack kellogg and tim sykes
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Jack was having some incredible success in 2021 swing trading OTC stocks. He funded an account just to do that style of trading.

In most of these plays he was putting in $10K and getting back $100K or more…

Before he knew it that $100K he funded was up to $1M.

Naturally, Jack thought if it worked so well…why not do it again…but this time with more size.

He got into junk marijuana stocks…

Instead of cutting losses he held on to them because thought that pot stocks would eventually have their moment and he would get a chance to sell at a pop…

After nearly two years of holding he bailed out on his positions and took a massive drawdown.

#2 It’s Better To Miss A Trade Than To Be Too Early

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One of the strategies that Jack likes trading is short-selling high flying pumps.

Unfortunately, he got caught in shorting the ticker symbol HKD in 2022, in one of the sickest Supernovas we’ll ever see

The stock went from $13 to $2,555 in a few short weeks.

Jack was relatively early in his short position…and he got tattooed.

It’s a lot harder to trade when you’re trying to climb out of a hole.

#3 Diversify Your Accounts

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Jack likes to keep several brokerage accounts. Some of them he has just to trade specific strategies.

But the big lesson is that he doesn’t want all his money in one trading account.

We’ve all heard horror stories of traders keeping all their money in one brokerage account, getting involved in one bad trade and getting wiped out.

That’s why he believes that you should have your capital spread out.

Many of the new accounts he opens are $100K or under. He prefers to build his accounts up vs. funding them with millions of dollars.

#4 Profit and Loss Does Not Define You?

students kyle mari and jack
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Jack didn’t have his first good month of trading until he was 20 months in.

In his first year he lost $2,600.

Does that mean he was a loser?

No…because he was gaining knowledge, experience, and developing skills.

You see, it was a slow build up for Jack.

You shouldn’t base your first few years on how much money you’ve made or lost. Instead, judge it on how much you’re studying, and improving from your earlier mistakes.

#5 Don’t Chase Euphoria

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A new group of traders made money in 2020 and 2021 but then began to lose it all in 2022 and 2023.

Having a high appetite for risk paid off in 2020, but if you didn’t adjust then your flaws were quickly exposed.

Jack doesn’t believe that luck has a role in long term success.

He’s not trying to get lucky with one stock, options play, or YOLO idea.

That’s why he believes in locking gains early and often to build confidence and consistency up.

He studies his best patterns and focuses on scaling up on his top ideas.

Final Note

jack kellogg and sykes in italy
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If you’d like to learn more about my mentoring program, the same one Jack was in, then click here for the details.  

Also, if you’d like to watch the video of this discussion with Jack and I, you can watch it below…

And don’t forget to comment…

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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”