Some context – I mostly trade options, mainly on index ETFs and tech stocks. Been trading for about 4 years, and honestly, the first 3 were pretty rough. Still working a day job in software engineering, which actually matters for how I view TradeWins’ stuff. Quick backstory: blew up my first account with Tesla options (who hasn’t?), built the second one back slowly, then discovered iron condors and thought I was a genius until volatility expansion taught me otherwise.
How I Found Them
Found them through a Reddit thread of all places. Someone was ranting about their prices (they’re not wrong – more on that later). Almost scrolled past, but there was this detailed comment about their gamma exposure course that caught my eye. I’d blown up enough positions mismanaging gamma to be interested.
Also, I was frankly tired of the usual trading education garbage. You know the type – “Make $10k a day with this one simple strategy!” Yeah, right. At least TradeWins looked… boring? In a good way?
The Options Education (The Real Meat)
Chuck Hughes is the real deal. Not in that fake guru way – in the “oh crap, that’s why my iron condors keep blowing up” way. He has this thing where he walks through actual trades, including the disasters. Last week he spent like 30 minutes breaking down a failed butterfly spread that looked eerily similar to one I’d messed up in July.
The biggest surprise? They don’t push some rigid system. It’s more like “here’s how these strategies work, here’s when they tend to blow up in your face, now figure out what works for you.” As a programmer, I appreciate that kind of systematic but flexible approach.
Let me break down one example that actually saved my butt: They have this module on earnings volatility that completely changed how I trade around earnings seasons. Used to get crushed by vega shifts I didn’t see coming. Now I actually understand why my positions move the way they do.
The Other Instructors (Mixed Bag)
Don Fishback‘s volatility trading course is solid gold. Dense as hell, but worth it. Took me three passes to really get it, but now I actually understand why some of my calendar spreads were basically guaranteed to fail.
Wendy Kirkland – honestly, I skip most of her stuff. Not because it’s bad, just doesn’t fit my trading style. She’s big on technical patterns, and I’m more of a volatility and probabilities guy.
About Those Prices… (The Painful Part)
Let’s talk about the elephant in the room – TradeWins isn’t cheap. Like, really not cheap. When I first saw the prices, I actually laughed. Then I thought about how much I’d lost on bad trades last year and suddenly it didn’t seem so crazy.
That said, they could be way more transparent about what you’re actually getting. Took me three emails to support to figure out if the advanced options courses were included in the main subscription (they’re not).
Break it down this way:
- Basic membership: Expensive
- Advanced courses: Very expensive
- Full package: “Maybe I should sell a kidney” expensive
But here’s the thing – one prevented loss can pay for the whole thing. Last month their volatility training helped me spot a problem with an RUT iron condor setup I was planning. Avoiding that one trade saved me more than the course cost.
After 8 months, here’s what’s actually worth your time:
The Really Good Stuff
Their Greeks deep-dive course – finally understand why vega matters so much in iron condors. This isn’t your basic “delta means directional exposure” stuff. They get into real-world applications. Like last week, I had this SPY position that was technically “delta-neutral” but was bleeding money. Turns out my gamma exposure was way higher than I thought. The course helped me spot that before it became a real problem.
The weekly market analysis is decent, though sometimes it comes too late to be super useful. Pro tip: watch the recordings at 1.5x speed. Chuck talks slowly.
Chuck’s live sessions are gold when I can catch them (they’re at weird times for my timezone). Last month he did this deep dive on adjusting broken iron condors that basically saved my monthly P&L.
The Not-So-Great Stuff
Haven’t even touched their forex stuff. Or the cryptocurrency section, which honestly looks kind of outdated. Some of the basic options content is pretty elementary if you’ve been trading a while.
The “trade alerts” section feels tacked on. By the time you see them, the setup is usually gone. Plus, blindly following alerts is a great way to blow up your account, which they actually tell you themselves.
Real Trading Results (No Marketing BS)
Not gonna throw out exact percentages because honestly, who keeps perfect track? But here’s the real deal:
Before TradeWins:
- Basically gambling with options
- No real plan for position sizing
- Panicked adjustments when trades went bad
After (8 months in):
- Actually understand why my trades work or fail
- Have a concrete plan for position management
- Know when to take the L instead of hoping for a miracle
Example: Last month I avoided a nasty loss on a SPY iron condor because I actually understood how earnings volatility compression would affect the position. A year ago I would’ve just seen the “perfect setup” and jumped in.
Comparison with Other Services
I’ve tried way too many trading services (my credit card company loves me). Quick rundown:
TastyTrade: Great free content, but can be overwhelming. TradeWins is more structured.
OptionAlpha: Good basic stuff, but TradeWins goes deeper into advanced concepts.
Random YouTube Gurus: LOL. No.
Who Should (and Shouldn’t) Use TradeWins
This is for you if:
- You actually want to understand options deeply
- Have some trading experience already
- Can afford the premium pricing
- Don’t need a lot of hand-holding
Not for you if:
- You’re looking for hot stock tips
- Want someone to tell you exactly what trades to make
- Need a super polished, modern platform
- Are just starting out (try TastyTrade’s free content first)
Bottom Line
If you:
- Actually want to understand options (not just follow alerts)
- Have the cash to spare (seriously, it’s pricey)
- Are willing to dig through a messy platform for good content
Then yeah, check out TradeWins. Just don’t expect perfection, and maybe send them some strongly worded feedback about their website. I do, at least once a month.
Start with the Greeks course. Trust me on this one. That butterfly spread isn’t going to trade itself (well, actually, it might trade itself right into a loss if you don’t understand gamma, but that’s a story for another day).
Personal Take After 8 Months
Would I sign up again knowing what I know now? Yeah, probably. The education has definitely improved my trading. But I’d skip some of the advanced courses that I never use and just focus on the options and volatility stuff.
Also, for the love of all things holy, please fix your search function, TradeWins. I’m tired of spending 20 minutes looking for that one video about calendar spread adjustments that I know exists somewhere in your platform.
Also Read: Unlocking the Power of Advanced Trading Platforms
