Is Trading with Ashley Legit? Review & $300k MSTR Loss (2026 Update)
Last Updated on April 25, 2026 by David Jaffee
Quick Verdict: Is Trading with Ashley Legit?
In my opinion, no — Trading with Ashley is not legitimate. While Ashley Wade is a popular influencer with polished branding, my research suggests Trading with Ashley poses significant risks for retail traders.
The evidence includes unverified trading results, a documented $300,000+ paper loss on a single MSTR trade, predatory sales tactics charging different prices based on account size, and a strategy (the “Wheel Strategy”) that historically underperforms a simple buy-and-hold approach to the S&P 500.
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Key Takeaways
- In my opinion, Ashley Wade lacks verifiable trading history or performance records — and her Discord trades cannot be independently confirmed
- Her flagship MSTR trade reportedly showed a $300,000+ loss at one point, demonstrating a fundamental misunderstanding of risk/reward asymmetry
- Predatory sales tactics: her closers charge different prices based on account size — signaling pricing manipulation rather than transparent pricing
- No trial offer: entry costs ~$1,800-$2,500, with the wheel strategy being the primary teaching despite multiple covered call ETFs (JEPI, QYLD, NUSI, XYLD) underperforming the S&P 500
- Educational content errors: Ashley reportedly does not understand basic options terminology (specific examples around the 3-minute mark of the embedded video below)
- Background: former member of Invest with Henry — uses similar simple LEAPS / wheel strategies you can learn for free elsewhere
- Estimated net worth ~$3 million — derived almost entirely from subscription fees and course sales, not from trading profits
- Trading with Ashley is NOT the worst options “guru” I’ve reviewed — that distinction goes to Invest with Corey, Felix Prehn (GOAT Academy), or Chris Sain
- My approach is fundamentally different: the Financed Bull Strategy uncaps upside potential while collecting premium, with verified multi-year returns of approximately +78% and +63%
- If you’ve already paid Trading with Ashley and feel misled: consumer resources at the bottom of this article explain how to file complaints with the FTC, SEC, your State Attorney General, and the BBB
Trading with Ashley & Ashley Wade: 2026 Status Update
As of April 2026, Ashley Wade and Trading with Ashley are still actively marketing through TikTok, YouTube Shorts, Instagram, and Facebook. Recent observations:
- Trading with Ashley continues to charge approximately $1,800-$2,500 for one-month Discord access — among the highest entry pricing in the industry
- The MSTR trade losses are still a recurring topic on r/options and Reddit threads about Ashley
- Multiple new complaints have surfaced on Trustpilot regarding refund difficulties
- Ashley continues to promote the Wheel Strategy despite multiple covered call ETFs underperforming over rolling 5-year periods
See recent discussions on r/options and Trustpilot for the latest student experiences.
8 Reasons Why Trading with Ashley May Not Be Legitimate
In my opinion, Trading with Ashley is not the worst educator I’ve reviewed (that would be Invest with Corey, Felix Prehn from GOAT Academy, or Chris Sain). However, Ashley Wade is probably not someone I’d want to follow or subscribe to. Here are eight specific concerns:
1. No Verifiable Trading History
Ashley Wade has no verifiable trading history or independently verified performance records. The trades shown in her Discord cannot be independently confirmed, lack real-world execution proof, and tend to be high-risk.
Trading with Ashley fails to provide transparency or proof that real trades are placed. In my opinion, some posted trades may be fabricated or misrepresented. She has also reportedly demonstrated unfamiliarity with basic options terminology in publicly available content (refer to the 3-minute mark of the embedded video above).
2. You Can Learn Everything Ashley Teaches for Free
Similar to Invest with Henry (her former mentor), Trading with Ashley teaches simple, common strategies — buying LEAPS, the wheel strategy, and basic covered calls. None of these are proprietary. None require payment to learn.
There is nothing in Trading with Ashley’s curriculum that’s unique enough to justify $1,800-$2,500 monthly Discord access.
3. Unrealistic Profit Claims
Ashley promotes profit expectations that often exceed 30% annual returns through simple options strategies. In my opinion, these claims are exaggerated and fail to account for market volatility, drawdowns, and the structural underperformance of covered call strategies during bull markets.
Her educational content reportedly contains fundamental errors and misconceptions about options mechanics. Strategies like indiscriminate covered call selling and buying LEAPS without proper hedging carry substantial risk that may not be obvious to inexperienced traders.
4. Predatory Sales Tactics
Her sales team reportedly employs high-pressure tactics, including aggressive upselling, manipulative emotional appeals, and personal-story-driven persuasion.
Trading with Ashley asks prospects to book phone calls with “closers” who reportedly charge different prices for the same product. If you tell them you have a larger account, you may be quoted a higher price than someone with a smaller account. This is pricing manipulation, not transparent pricing.
If you feel you’ve been a victim of predatory sales tactics, file a complaint with your State Attorney General or the Federal Trade Commission — see the Consumer Resources section at the bottom of this article.
5. Failure to Understand Basic Trading Principles
Ashley reportedly makes mistakes that even beginner traders would not make. Examples include calculating expected profit using the maximum loss number rather than the premium collected, and misunderstanding the risk profile of common options structures.
In my opinion, Ashley primarily engages in hypothetical trading rather than real trading. She does not share verified brokerage statements showing actual P&L.
6. The $300,000+ MicroStrategy (MSTR) Disaster
This is the single most damaging episode in Trading with Ashley’s public record.
Ashley placed risky trades on MSTR that, at one point, reportedly showed a paper loss exceeding $300,000. The trade structure had approximately $1,100 in potential upside versus enormous downside exposure — a textbook example of inverted risk/reward geometry.
By making this trade, Ashley demonstrated either inexperience with risk management or a willingness to place trades with mathematically unfavorable odds. Either is disqualifying for someone charging $1,800+ monthly to teach options.
While Ashley can compensate for personal trading losses with her subscription income, her members who follow her into similar trades cannot afford that cushion.
7. High-Cost, Low-Value Programs
Similar to Options with Ryan and Chris Sain, in my opinion Ashley’s programs are overpriced and fail to deliver proportional value.
The lack of a trial offer (you cannot test the service for less than $1,800-$2,500) creates a significant financial barrier. By the time members realize the strategy doesn’t suit their account size or risk tolerance, they have already paid.
I also believe her members will face substantial drawdowns during the next bear market — which is the test that exposes most “wheel strategy” influencers as marketing-first, trading-second.
8. The Strategy Flaw: Why the Wheel Underperforms
Ashley Wade primarily teaches the Wheel Strategy: sell puts → get assigned shares → sell covered calls → repeat.
The fundamental problem with this approach:
- Capped winners: As demonstrated by her MSTR trade, when a stock rallies, your shares get called away at the covered call strike. You collect a small premium and miss the bulk of the gain. The most profitable trades in any portfolio are the ones the wheel strategy systematically caps
- Tax inefficiency: Constant generation of short-term capital gains taxes (taxed at ordinary income rates, up to 37% for high earners) versus longer-term holdings or Section 1256 contracts which enjoy a 60/40 long-term/short-term blend
- Real-world ETF data: Every major covered call ETF — JEPI, QYLD, XYLD, NUSI — has dramatically underperformed the S&P 500 over multi-year periods. If institutional traders running this strategy with professional risk management can’t beat the market, retail traders with less infrastructure won’t either
For the complete data-driven breakdown, see Why the Wheel Strategy Underperforms.
See the Strategy That Actually Beats the Wheel Real-time options alerts from a verified Wall Street trader with multi-year +78% returns. 14-day trial available — no long-term commitment.
Ashley Wade Net Worth: Trading Profits or Marketing Funnels?
I estimate Ashley Wade’s net worth at approximately $3 million. However, in my opinion, this wealth is almost entirely derived from subscription fees, course sales, and affiliate marketing — not from trading profits.
In fact, given the structural underperformance of the wheel strategy and her demonstrated risk management issues (the MSTR trade), I believe it’s unlikely her trading methodology beats the market over the long term.
Ultimately, virtually all of Ashley Wade’s wealth appears to be tied to her highly optimized sales funnels and her ability to convince beginners to pay premium pricing for membership programs — rather than a verified, profitable trading track record.
A Better Way: The Financed Bull Strategy
You don’t need to pay $1,800-$2,500 for basic wheel strategy theory that historically caps your upside.
At BestStockStrategy, I use a fundamentally different approach: the Financed Bull Strategy. Here’s how it differs from Ashley’s wheel:
| Factor | Ashley’s Wheel | Financed Bull |
|---|---|---|
| Upside capture | Capped at covered call strike | Captures full upside via call spread |
| Downside protection | Full stock ownership risk | Defined risk on the call side |
| Capital required | 100% of share value when assigned | Often near-zero net cost |
| Tax treatment (single stocks) | Constant short-term gains | Same, but smaller positions = less drag |
| Works in bull markets | ❌ Underperforms (caps gains) | ✅ Outperforms |
| Works in flat markets | ✅ | ✅ |
| Works in bear markets | ❌ Fully exposed | ✅ Hedged via call spread structure |
The Financed Bull works by buying a call debit spread (to capture upside) and financing it by selling a naked put at a strike where you’d genuinely want to own the stock. The result: you can often enter the trade for zero net cost or a net credit, with defined risk, and significantly higher upside than a wheel position.
My verified 2025 results were generated using this approach. My two real E*TRADE trading accounts returned approximately +78% and +63% over 11-12 months, with the complete monthly breakdowns published in Can You Make a Living Selling Options?.
For the complete framework, see Most Successful Options Trading Strategies (2026 Guide).
Conclusion: Is Trading with Ashley Worth It?
In my opinion, Ashley Wade’s strategy may produce reasonable returns during a sustained bull market. However, she takes excessive risk relative to the available premium, and her program requires approximately $1,800-$2,500 just to test — with no trial offer that I’m aware of.
Her teachings are simple and freely available from many other YouTubers. Her sales team uses high-pressure tactics. The MSTR trade demonstrated either a lack of risk management or a willingness to place trades with unfavorable risk/reward.
That said, Trading with Ashley is not the worst YouTube educator I’ve reviewed. That distinction belongs to Invest with Corey, Felix Prehn, or Chris Sain.
If you’re considering joining Trading with Ashley, I’d recommend exploring my free training first — see whether you can achieve your trading goals without paying $1,800-$2,500.
If you’ve already paid Trading with Ashley and feel misled, see the Consumer Resources section below.
Consumer Resources & Protection
If you feel you have been misled by Trading with Ashley, Ashley Wade, or any other high-priced trading course, you have the right to report deceptive marketing practices, predatory sales tactics, or unhonored refund policies.
Recommended government and consumer protection agencies:
- Federal Trade Commission (FTC): Report Fraud & Deceptive Advertising
- Securities and Exchange Commission (SEC): Submit an Investment Fraud Tip
- Find Your State Attorney General: State AG Directory
- Better Business Bureau (BBB): File a Complaint
For additional information on options risks and investor protection, see the SEC’s investor bulletin on options and the Cboe Options Institute.
Ready to See Verified Trades and Disciplined Risk Management? Join the 127+ five-star verified members already following the Financed Bull Strategy. Real-time alerts from a verified Wall Street trader with multi-year +78% returns.
Frequently Asked Questions: Trading with Ashley Review
What is Trading with Ashley’s real name?
Trading with Ashley is run by Ashley Wade.
Is Trading with Ashley a scam?
In my opinion, while Ashley Wade is not the worst options educator I’ve reviewed, Trading with Ashley relies on unverified trading results, predatory sales tactics, and a flawed strategy (the wheel) that historically underperforms a simple buy-and-hold approach. I don’t believe the program offers value commensurate with its $1,800-$2,500 entry pricing.
Who taught Trading with Ashley how to trade?
Ashley Wade was a former member of Invest with Henry. The strategies she teaches (LEAPS buying, wheel strategy) are similar to Henry’s curriculum.
What is Ashley Wade’s net worth?
I estimate Ashley Wade’s net worth at approximately $3 million — almost entirely derived from membership fees, course sales, and affiliate marketing rather than trading profits.
Is Trading with Ashley’s strategy risky?
Yes, in my opinion. Ashley has placed high-risk, low-reward trades — most notably an MSTR position that reportedly showed a $300,000+ loss at one point. Members who followed her into similar trades may have faced significant losses.
The Wheel Strategy itself caps upside potential while leaving full downside exposure during market crashes. Every covered call ETF (JEPI, QYLD, NUSI, XYLD) has dramatically underperformed the S&P 500 — institutional evidence that this strategy structurally underperforms.
What happened with the MSTR trade?
Ashley placed a trade on MicroStrategy (MSTR) that, at one point, reportedly showed a paper loss exceeding $300,000. The trade structure had approximately $1,100 in potential upside versus enormous downside exposure — an inverted risk/reward profile.
Does Trading with Ashley offer a free trial?
Not that I’m aware of. The cost to test the service is approximately $1,800-$2,500 for one month of Discord access — among the highest entry pricing in the options education industry.
Are Trading with Ashley reviews authentic?
Many positive reviews appear to come from members who have not yet experienced a sustained drawdown. Negative reviews on Trustpilot and r/options describe refund difficulties, predatory upselling, and trade losses. Always verify reviewers’ actual trading account performance, not just their testimonials.
What’s a better alternative to Trading with Ashley?
The Financed Bull Strategy. Instead of capping upside with covered calls (the wheel approach), buy call debit spreads and finance them by selling naked puts at strikes where you’d genuinely want to own the stock. This combination uncaps upside while collecting premium. See Most Successful Options Trading Strategies for the complete framework.
Where can I see verified trading results?
I publish my real E*TRADE statements with month-by-month performance data. Verified results from two trading accounts (~$600K and ~$1.85M) over 11-12 months show approximately +78% and +63% returns respectively. Full monthly screenshots will be published at beststockstrategy.com/results in May 2026.
Should I file a complaint about Trading with Ashley?
If you’ve been misled by Trading with Ashley’s marketing, denied a refund despite legitimate cause, or feel you’ve experienced predatory sales tactics, you have the right to file complaints with the FTC, SEC, your State Attorney General, and the Better Business Bureau. See the Consumer Resources section above.
What is the best free options trading education?
If you’re looking for a starting point, see my $400+ free options trading training at beststockstrategy.com/stock-market-secrets. It includes the Trader’s Edge cheat sheet and the foundational framework for the Financed Bull Strategy.
This review reflects my personal opinion based on publicly available information. It is not financial advice. Options trading involves significant risk. Past performance does not guarantee future results. Always consult a qualified financial advisor before making investment decisions. David Jaffee and BestStockStrategy are not registered investment advisors.
About the Author David Jaffee
David Jaffee is the founder of BestStockStrategy.com and creator of the "Financed Bull" Strategy. He graduated from an Ivy League university and worked at Wall Street's most successful investment banks before becoming a full-time options trader and educator. David has taught over 2,500 students in 70+ countries, and his strategy has achieved a win rate approaching 98%. He specializes in selling options for premium income and buying call spreads for long-term wealth building. Verified Trading Results | Student Reviews | Trading Course & Trade Alerts | Watch on YouTube | Personal Website
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