A Real Trader’s Journey with TradeWins (Month 8 and Counting)

I almost didn’t write this review. After blowing money on countless trading courses over the years, I’m pretty cynical about the whole “trading education” industry. But something about TradeWins has been different enough that I figured it was worth sharing my experience.

Finding TradeWins (Or How Reddit Actually Helped for Once)

I stumbled across TradeWins in the most 2024 way possible – doom-scrolling Reddit at 2 AM after a rough trading day. Someone was complaining about their prices, but what caught my eye was this detailed comment about gamma exposure. As someone who’d recently blown up a few positions by mismanaging gamma (hello, Tesla options), I was intrigued enough to look deeper.

The Options Education That Actually Clicked

Chuck Hughes surprised me. Instead of the usual trading guru nonsense about “guaranteed wins” and “secret strategies,” he spends time breaking down real trades – including the ones that failed spectacularly. Last month he spent an entire session analyzing a butterfly spread gone wrong, and I had flashbacks to three nearly identical trades I’d messed up last year.

The way they teach options just makes sense to my engineering brain. It’s not about rigid rules or “perfect” setups. Instead, they break down how different strategies actually work, when they tend to fail, and why. Their module on earnings volatility completely changed how I handle earnings season. I used to get destroyed by vega shifts I never saw coming – now I at least know why I’m losing money (kidding, mostly).

The Teaching Style – Mixed But Mostly Good

Don Fishback’s volatility course nearly broke my brain, but in a good way. Took me three passes through the material before it really clicked. Now I finally understand why some of my calendar spreads were basically doomed from the start.

Wendy Kirkland’s technical analysis stuff isn’t really my thing. I tend to zone out during pattern discussions – give me volatility stats and probability calculations any day. That’s just my style though; plenty of folks in the chat rooms swear by her methods.

Let’s Talk Money (Because Everyone’s Thinking It)

TradeWins isn’t cheap. When I first saw the pricing, I laughed. Then I added up my trading losses from last year and suddenly it didn’t seem so outrageous. Still, they could be clearer about what you’re getting. The advanced options courses aren’t included in the basic subscription – took me multiple emails to support to figure that out.

Their volatility training helped me dodge a bullet with a RUT iron condor setup last month though. That one avoided loss more than paid for the course. Funny how expensive education seems cheap compared to expensive mistakes.

The Daily Reality of Using TradeWins

The Greeks deep-dive course was a game-changer for me. I had this SPY position last week that looked fine on paper – delta neutral and everything – but something felt off. The course helped me spot my gamma exposure problem before it turned into a real headache. That’s the kind of practical stuff I wish I’d known years ago.

Their weekly market analysis is decent, though sometimes it hits my inbox a bit late to be super useful. Pro tip if you watch the recordings: Chuck talks like he’s getting paid by the word. 1.5x speed is your friend.

When I can catch Chuck’s live sessions (seriously, who schedules these things for 2 PM Eastern?), they’re pure gold. His breakdown of adjusting broken iron condors last month basically saved my monthly P&L. Though I still have the recording bookmarked somewhere in their platform… if I could only find it again.

The Stuff Nobody Talks About

Not everything is perfect. Their forex content feels like an afterthought, and I haven’t even looked at their crypto section – pretty sure it’s from the era when Bitcoin was still the new kid on the block. Some of the basic options content would bore anyone who’s been trading for more than a few months.

The trade alerts section… well, let’s just say by the time you see them, the ship has usually sailed. Though I appreciate that they constantly warn against blindly following alerts. They’re pretty adamant about understanding why a trade works before putting money on it.

Real Results (The Part You Actually Care About)

I could make up some exact win rate percentages, but let’s be real – trading isn’t that clean. What I can tell you is that my trading has fundamentally changed. Before TradeWins, I was basically gambling with a fancy vocabulary. Now, I actually understand why trades work or fail.

Last week, I caught myself analyzing an earnings play using concepts I didn’t even know existed eight months ago. Still made a small loss, but it was a planned, controlled loss instead of a “oh god why is theta crushing me” kind of loss.

How It Compares to Other Stuff I’ve Tried

I’ve probably spent enough on trading education to buy a small car. TastyTrade has great free content, but it can feel like drinking from a fire hose. OptionAlpha does basics well, but TradeWins goes deeper into the concepts I actually needed. And don’t get me started on random YouTube gurus – though their “shocked face” thumbnails are always good for a laugh.

Should You Try It?

Here’s the thing – if you’re looking for hot stock tips or someone to tell you exactly what to trade, save your money. If you’re just starting out, honestly, hit up TastyTrade’s free content first.

But if you want to really understand options, have some trading experience already, and can afford the premium pricing (seriously, their prices aren’t a typo), then yeah, it might be worth checking out. Just start with the Greeks course. Trust me on this one.

Eight Months Later…

Would I sign up again? Yeah, probably, but I’d skip some of the advanced courses I never use and just focus on the options and volatility stuff. The education has definitely improved my trading, even if my wife still rolls her eyes when I start talking about gamma scalping at dinner.

Trading is hard enough without making it harder by being undereducated. TradeWins helped fill in gaps I didn’t even know I had. Just maybe don’t ask me about that Tesla strangle I put on last month. Still a bit salty about that one.

P.S. – If you end up joining and see someone in the chat obsessing over volatility surface charts, that’s probably me. Say hi. We can complain about gamma exposure together.

P.P.S. If you want a sneakpeak into their training, check out the Tradewins Youtube Channel

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Editorial Team