Hands down one of the BEST communities for learning to buy and sell options! The support here is unreal—questions get answered almost instantly, and the depth of knowledge is absolutely top-notch. Wha... See more
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Trading with Ashley is an educational company that teaches investors, from beginners to advanced, how to trade options. Ashley's approach focuses on selling options rather than buying, with the goal of generating consistent returns while minimizing risk.
601 Kingston RD STE 300/1002, 71006, Benton, United States
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Joined TWA Inner Circle in August 2025. Took a leap of faith and re-couped the IC investment in the first full month of trading. Ashley, her amazing Team, and the Community are the Best!

Reply from Tradingwithashley
Ashley and her coaches provide daily hands-on support to help us be successful traders and investors. The community is also great at supporting each other, bringing fresh ideas and help each other learn. It has been well worth the investment.

Reply from Tradingwithashley
I joined the community in January 2026. I have no regrets in this investment. My realized gains more than covered the cost of this investment in a couple of weeks. The community has been extremely helpful to properly structure option trades to reduce likelihood of getting assigned, but if assigned strategies to mitigate.

Reply from Tradingwithashley
The sincerity expressed by the entire team. Not a negative vibe to be found. Everyone is truly concerned with personal growth for all

Reply from Tradingwithashley
Ashley’s Discord is truly on another level. The learning experience is exceptional, and it has become a constant source of knowledge and growth for me. Every day there is valuable analysis about the market, companies, ETFs, and trading strategies that help you better understand how the market really works.
What makes this community even more special is Ashley and the Coaches. They are always present, guiding and supporting everyone, making sure no one feels lost in the process. They genuinely care about helping people grow and showing that profitability in the market is possible when you have the right strategy, discipline, and mindset.
I’m extremely grateful to be part of a community that not only teaches trading, but also builds confidence and consistency. Highly recommended for anyone who truly wants to learn and improve in the market.

Reply from Tradingwithashley
Ashley is the real deal. With a heart to serve and a deep desire to see her students succeed, along with the amazing team of coaches and community...well, it's a no brainer. I'm thrilled to be a part of this community and learning so much every single day.

Reply from Tradingwithashley
Ashley and the team of coaches are awesome and very responsive. The community is also very collaborative and share trade ideas. More importantly the trade doctor advice we get to keep each other accountable and salvage bad trades is cool.

Reply from Tradingwithashley
I want to start by saying I have mixed feelings about this investment group. I have been a member for 8 months and at times found value in the group. In a bull market, the gamified strategy on selling puts and calls and buying leaps and skips feels like you are outsmarting the masses. In a few cases, this is true. There are some incredible traders in the group who have made excellent decisions and been rewarded handsomely.
In addition, the coaches and Ashely are incredibly responsible and take the time to answer every members question thoughtfully. There are many talented coaches who provide logical advice to many happy traders in this group. For some, this may be worth the hefty price tag.
Although I do not have access to every members financials I would suspect that the average person that joins the group doesn’t even come close to beating the average return of the SNP 500.
In my personal scenario, I had some early success selling puts and earning close to 2000 per month realized gains for the first few months. Unfortunately, when the market enters a pullback traders in the group are often assigned positions far under cost basis. That means although I earned over 10K during my time in the group, I also picked up over 15K unrealized losses. Although I did not sell all these positions, it is a very frustrating position to pay taxes on realized gains while being weighed down with heavy unrealized losses. As a caveat, I did not take every trade Ashely recommended. She recently recommended a QQQ skip near the recent Iran lows (an incredible play). Even so after being burned by Hood, sofi, TTD, and countless others I didn’t have the confidence to continue filling the recommendations.
Overall I am about even since joining the group. In contrast, the snp 500 returned 15.5% since June 30th 2025 to today. Obviously I would have been better off throwing my cash into VOO.
I think the challenging part about these groups is the underlying business model. The success of the business depends on keeping people engaged and trading actively. Calm, boring, long term investing doesn’t generate Discord activity or keep subscriptions feeling valuable. So there’s a structural incentive to always have a new trade idea even when the right answer is to do nothing.

Reply from Tradingwithashley
Ashley's practical and no-nonsense approach to trading options is inspiring.
Her ability to simplify, communicate, teach and share options strategies in any market condition is unmatched.
Her team of coaches are very helpful and all are willing to share their trades but also their wisdom in trading in the market.
I'm putting into practice what I've been exposed to and what Ashley taught in class.
Looking forward to a blessed and fruitful 2026!

Reply from Tradingwithashley
Trading with Ashley has totally transformed my trading .Her knowledge and way of teaching is like none other ! She uses real life analogies to make it fun and easy to comprehend, and retain. I wish I had joined the community long ago. Not only is she amazing, the community is fantastic. We’re like one big family.

Reply from Tradingwithashley
I waited a year before I decided to make the jump, and I’m so happy I did. Ashley’s teachings, her devotion, the wonderful coaches, and the community, she built, are nothing but amazing. I’m grateful to be able to learn and grow with everyone and feel 100% supported.
Thank you Ashley.

Reply from Tradingwithashley
Joining Trading with Ashley and completing her bootcamp has been one of the best decisions I have ever made in my trading journey. I came in with limited confidence in options trading, and I am leaving with real knowledge, structure, and actual results.
Ashley is an incredible teacher—clear, patient, and genuinely invested in helping her students succeed. What truly sets this community apart is Ashley’s Inner Circle on Discord. The amount of daily education, real-time trade ideas, market breakdowns, and support from both Ashley and the coaches is absolutely unmatched. weekly zoom calls, 2 of which Ashley hosts. You are never left feeling alone in a trade or confused about the market.
The coaches are phenomenal—each bringing their own strengths, experience, and teaching style, but all sharing the same goal of helping members grow and win consistently. And the community itself is full of supportive, knowledgeable traders who share ideas daily.
This is not a “get rich quick” group. This is real education, real discipline, real strategy, and real growth. I now trade with confidence instead of fear, and my results prove it.
If you are serious about learning options trading the right way, I cannot recommend Trading with Ashley enough. This group truly changes lives—mine included.

Reply from Tradingwithashley
TWA provides regular trade ideas, plenty of knowledge transfer, and constant positive feedback, providing me the know how and support I was looking for in my trading experience! I am extremely happy I chose to join Ashley's inner circle.

Reply from Tradingwithashley
I followed her on YT for months. I really appreciate her folksy teaching style, and she is a gracious and patient teacher. I actually was a skeptic for a while, but I saw her opinions / market predictions consistently came to pass. Yes, it was pricey to join the community, but I'm so glad I did! I made my membership fee back in short order. I went "from Red to Green"! TWA is a great community and I am no longer on this path all alone. Worth it!

Reply from Tradingwithashley
I started following TWA after seeing Ashley on a master class with Kenan Grace. She started a new trader challenge a few weeks later using the PCS strategy she taught sitting the masterclass with Kenan. I joined the challenge and made the membership fee in the first week. Actually double. I caught on to the strategy by the end of the second week. I want a complete beginner. But I had never heard of this strategy as I was only into trading just at a year approaching this challenge. The first month my total gains were over $2k and the second month over $4k. I had zero losses in total weekly profit in the month of October. In September only one week with negative P/L and that was -$55.00 This group has been amazing and extremely helping to my teaching journey. I’ve decided to use my profit to upgrade to a bigger challenge!

Reply from Tradingwithashley
Ashley is such a caring person. She is as she appears in her Youtube channel. She is a great teacher and after a while you gain the confidence to trade on your own, but if you just follow her trades on her Discord, you will make money.

Reply from Tradingwithashley
Ashley, thank you for your full dedication to this community. I have been part of 3 other discords but yours surpasses every expectation. In your community, there is no stupid question, I feel like I can ask anything, even if it’s the simplest question. That’s huge for me, especially when you are new to option trading. I knew I had found something special when I joined your PCS challenge and I ten fold the cost to enter the challenge in one month. So from the bottom of my heart, thank you for giving me hope to retire early and for opening the possibility to change my family legacy.

Reply from Tradingwithashley
I’ve been a TWA discord community member for a little over one month. Her community is an active, dynamic group of traders that are welcoming, helpful and generous with sharing their knowledge and experience.

Reply from Tradingwithashley
Ashley is absolutely awesome — incredibly caring and genuinely focused on helping us achieve great returns. She makes every trading strategy feel simple and easy to understand, and she’s truly an amazing teacher.
I’ve been following her for two years and thought I could trade on my own just by watching her videos. But I found myself taking risky trades and often giving back what I made. Finally, I decided to join her community, and it has far exceeded my expectations.
Ashley is so supportive and ensures that everyone feels guided and encouraged. The community itself is incredible — every time I have a question, it’s answered right away. I’m so happy I finally joined!

Reply from Tradingwithashley
I am so glad I found Ashley’s channel! iv been with the community for a while now ,after trading multiple styles over the years, I think iv found the one Ashley & her coaches teaching style are fun passionate patient & considerate,,all of the coaches trade in different ways so you will bound to find someone that suits your trading style ,the team she has with her really are amazing !! & you will learn a lot & you will make money as a byproduct ,,the recordings library are worth it in themselves,im not into shilling anything but I do believe Ashley & her team of coaches deserve it ,& are great people to look up to ,thank you team ⭐️, ps the community is also a great well mannered bunch who are happy to share , if your like that also ,just join 😉

Reply from Tradingwithashley
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