Jack Kellogg Retirement Trader Masterclass
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Jack Kellogg’s story is often cited as a modern-day trading success built on discipline, obsession-level focus, and a willingness to sacrifice comfort for long-term goals.
Raised in a small town in Connecticut, he didn’t come from money or have any financial background to give him a head start.
In fact, he’s spoken openly about growing up with dyslexia and struggling academically, which meant he had to develop an alternative route to success. That route ended up being the stock market.
His introduction to trading came through watching videos online and eventually discovering Timothy Sykes, a prominent penny stock trader known for turning a few thousand dollars into millions.
Intrigued by the potential and motivated by the idea of financial freedom, Kellogg enrolled in Sykes’ Trading Challenge. Unlike many others who passively consume trading education, Kellogg went all in.
He treated it like a full-time job — waking up before the market opened, studying charts late into the night, and journaling his trades meticulously.
In the early years, he didn’t see immediate success. He made many small mistakes, blew up small accounts, and often felt discouraged. But instead of quitting, he used those losses as fuel.
He continued refining his edge and became incredibly focused on pattern recognition — especially in low-float stocks, OTC breakouts, and momentum-based strategies. He learned to capitalize on “FOMO” plays, where retail traders chase price action, and he developed an eye for when the hype was real and when it was time to exit.
Eventually, his dedication started to pay off. He grew his personal accounts dramatically, and one of his most impressive achievements was growing a Roth IRA account from around $10,600 to over $3 million in roughly a year.
This caught the attention of the trading world not only because of the magnitude of the gain but because Roth IRAs have strict contribution limits — so the only way to achieve that kind of growth is through performance, not deposits.
Kellogg’s style involves a mix of long and short strategies, with a heavy emphasis on reading price action. He is especially skilled at identifying “hot sectors” — areas of the market experiencing speculative interest, like EV stocks, biotech, or crypto-related plays — and then focusing on the most volatile and liquid tickers within those sectors.
As of recent years, Kellogg has been featured on several trading podcasts, webinars, and live events.
He’s appeared on the SteadyTrade Podcast, been interviewed by Sykes’ team, and spoken at Traders For a Cause, an annual charity trading conference.
His transparency about both his successes and his mistakes has earned him respect in the trading community.
What sets him apart is not just his profits, but his mentality.
He talks frequently about how he had to detach from money emotionally in order to trade well — understanding that losses are part of the game and that fear and greed are the two emotions that destroy most traders.
He’s also emphasized the importance of stepping away during cold streaks to reset mentally, and he doesn’t shy away from the fact that trading can be mentally grueling and isolating.
Despite having made tens of millions, Kellogg continues to trade and improve.
He also uses his platform to give back to newer traders, often sharing lessons on Twitter, Discord groups, and in interviews.
His core message remains the same: trading success isn’t about luck — it’s about putting in thousands of hours, being patient, and developing the emotional discipline to stick to your plan when everyone else is panicking.
Jack Kellogg Retirement Trader Program: What Do You Get?
The main meat of this program is of course the Jack’s ROTH IRA Video Masterclass. This is an hour long video from a guy that went from $10k to $1.8MM.
The first 5 minutes is Jack explaining his story, his accomplishments and why he decided to start trading primarily in a ROTH IRA. The program discusses the following….
I love the transparency where he shows his brokerage account.
About 10 minutes in he starts a section all about what patterns he actually uses. He learned these from Tim Sykes and they are proven over time. He talks about how he handles drawdowns.
- Good section mistakes he learned along the way.
- Decent section about what he does when the market is strong and how he does MORE to really take advantage and grow his account
- He seems to be good at taking advantage of the market and eases off when it’s weak and turning up the gas when it’s strong.
- Half-way through there is a discussion about his Power Signals which costs $2495…..
- He has a decent section demonstrating real-life examples of a few of his key patterns. Some of these are pretty simple strategies to implement. However, this section is lacking on how to scan for these opportunities. Although this wouldn’t be too hard with some simple filters set in ThinkorSwim for example or using something like Tim Bohens Money Bar Indicator.
- Gives kind of an overview of what charts to look for and what charts to avoid.
Overall, I wasn’t overwhelmed by the main course. I felt there were a few nuggets but it didn’t leave me filling fulfilled.
However, this changed a bit when I started looking at the bonus materials which filled some of the gaps I felt were missing in the main video course!
Bonus: Masterclass Reports
These did help me understand his mindset and patterns a lot better. He gives his favorite indicators etc.
Bonus: Tim Sykes Mindset Module
Bonus: Tim Sykes Trading Tax Strategy Consultation. This is a pretty good bonus as you get a free call with an affiliated service that advises you on using an LLC to trade with etc. and the tax advantages of doing so. I get a few questions about this so it’s nice to see it included a a bonus.
There is a lot packed into this course for $97 in terms of mindset, ideas for patterns and plenty of interviews with millionaire traders that could help you avoid their mistakes and learn what they did right.
There aren’t any alerts, and you won’t learn a secret strategy that takes you to the next level though as the information is quite general.
If you are looking for a packed course that helps your overall trading though this might well be for you at the price (plus if you don’t like it they are known to give you your money back!).
Check it out here for just $97.
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