Last week I did a webinar with Jack Kellogg.
Jack dropped SO many nuggets of gold…
I’m sure you know about Jack’s success.
But what many people don’t know (or forget) is just how hard Jack worked to get where he is.
And he’s STILL working hard to become an even better trader.
Buckle up while I share 5 lessons from master trader Jack Kellogg.
Table of Contents
- 1 The Setup
- 2 5 Lessons From Jack Kellogg
- 2.1 What was your biggest loss this year? How did it feel?
- 2.2 What do you think about fake out breakouts, especially with biotechs?
- 2.3 “I’m going through the Challenge course for the first time. Is Jack’s strategy outlined in the course?”
- 2.4 How important is it to take a step back and NOT trade sometimes?
- 2.5 What do you think of people comparing themselves to Twitter Traders?
- 3 Millionaire Moves
- 4 Study HARD!
The Setup
This might sound odd if you don’t know all the ins and outs.
Jack is up roughly $700,000 this year (his estimate) but he’s taking some time away from trading.
If you’re an experienced trader or already part of the community you might know why.
But if you’re new to this game you might wonder…
“Why take time off if you’re up so much?”
Let’s dig right in…
5 Lessons From Jack Kellogg
Jack answered my questions and those from Trading Challenge students during the webinar.
The first question came from me…
What was your biggest loss this year? How did it feel?
Jack Kellogg: My biggest loss this year is silver for sure. I went from being up over $500,000 to red almost a million dollars on silver.
That felt [terrible] because it didn’t make sense to me. I hadn’t seen these kinds of supernovas before.
Then, unfortunately, it gapped down and cracked massively and I missed the trade.
Silver was down 35%+ in one day and I didn’t make $1 shorting it.
My take: You cannot outrun your risk management. I see some people saying “who cares what the risk is if you make money?”
You have to care, because on any play, especially when you’re betting big, it’s a very slippery slope.
What do you think about fake out breakouts, especially with biotechs?
Jack Kellogg: Biotechs have always been super choppy. I might be overall red on biotech throughout my entire trading career.
A lot of these biotechs, you can’t trade the price action that well. It’s more in the fundamentals.
So, if you’re a great fundamental analyst and you know what these companies’ agenda is, you’re able to trade with that agenda.
But in terms of buying breakouts, price action, using VWAP, support and resistance, volume…
These things are just choppy.
My Take: Specifically with biotech, you get these nasty candles. It looks like it’s breaking out, and that is the beginning of the end because these companies need cash.
So, any strength is sold into.
The next question came from a Trading Challenge student…
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“I’m going through the Challenge course for the first time. Is Jack’s strategy outlined in the course?”
Jack Kellogg: I have probably a hundred webinars. So, my strategy is definitely outlined in the course.
If you do want more of the tools that I use and more of my strategy, you can look at classes I have on JackKelloggTrading.com.
But the webinars are sufficient to learn a lot about what I do.
There are so many tools and options to learn in this community.
As a beginner you should try to soak everything up and learn as much as you can.
It’s going to save you money rather than wasting money donating to the market.
If you invest in yourself and in education, it’s going to pay dividends in the future.
My Take: Remember, you have to grow your knowledge account before you grow your trading account.
How important is it to take a step back and NOT trade sometimes?
Jack Kellogg: No matter how good you are at trading, the market will always humble you. Or the market will change. Or you’ll go through some type of rough period.
I don’t know anyone who’s just breezing every single day.
Eduardo has done nicely because he does the most controlled risk control with scalping. But also, he’s not going to have huge upside potential on massive winners. So, it comes with pros and cons.
Everybody needs to adapt and do stuff differently. A lot of people think that once they gain success, they’re never going to lose. That’s not the truth.
I’m having a choppy six months and I have to make adjustments.
My Take: Jack has made $25 million, but every now and then he has to step back (and every now and then I have to take a step back).
So, no matter where you are in your journey, don’t feel bad if you have to take a step back.
It’s far worse NOT to take a step back and think you have to size in.
Finally, I asked Jack to share his perspective on comparing yourself to others…
What do you think of people comparing themselves to Twitter Traders?
Jack Kellogg: It’s very hard to compare yourself to Twitter traders or people who aren’t showing their full track record.
A lot of these people hide their biggest losses. Or they hide their trades.
If someone says they never go through a bad period, they’re probably lying. You cannot learn from people who aren’t sharing.
My Take: Jack is one of the most successful traders in the world. He sees what’s good and what’s bad. He has perspective.
A lot of people think that traders on Twitter are making so much money that it’s easy. They feel like they’re doing something wrong if they’re not making money.
Millionaire Moves
My friend (and trading legend) Ben Sturgill is a highly regarded options trader and mentor with 20 years of market experience.
Like me, Ben started his trading career as a teenager. Now, he’s one of the best options traders and teachers I know.
Ben is running a two-day options bootcamp starting tomorrow, May 12. I HIGHLY recommend you join Ben’s Simpler Options bootcamp to learn his strategy.
On My Radar
I’m SO proud of Mari and happy she’s back making videos and inspiring other traders. We need more traders with her wisdom.
Success in trading has nothing to do with gender and everything to do with discipline, preparation, and confidence. @Mari_trades, a million-dollar trader inside the @timothysykes Inner Circle, is inspiring more women to step into the markets and realize what’s possible 📈🔥 pic.twitter.com/96oakra79Q
— StocksToTrade (@StocksToTrade) May 8, 2026
Study HARD!
Jack, Mari, and Ben are all inspirational traders. And you should learn as much as you can from them and their journeys.
Just remember that every minute you put into studying is one minute closer to freedom.
Have a great week!
Cheers,
– Tim Sykes
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