Investor Round-Up With Dream.Trade.Retire
Matthew, a Master Sushi Chef and U.S. Army veteran, shares his journey from trading options to creating Dream.Trade.Retire, a platform focused on teaching trading strategies and mindset shifts.
I am interviewing Matthew from Dream.Trade.Retire.
Every investor has their own way to build their wealth by investing.
The goal for this interview series is to share lessons from investors so you can build an investment style that works best for you.
We are going to learn from Matthew’s journey.
Let’s get started.
Matthew, can you tell us a little about yourself?
I started my career as a sushi chef, spending seven years mastering the craft and achieving the title of Master Sushi Chef in just seven years—a milestone that typically takes a decade. That experience taught me discipline, precision, and the importance of continuous learning.
In 2023, I transitioned into the military, enlisting as a 25B Information Technology Specialist in the U.S. Army. I also volunteered for airborne training and was assigned to the prestigious 82nd Airborne Division. During Advanced Individual Training (AIT), I developed a strong foundation in networking, configuring routers, switches, and firewalls. Seizing the opportunity to enhance my skill set, I earned my Security+ certification and graduated with honors. From there, I attended airborne school—one of the most exhilarating experiences of my life—where I had the opportunity to jump out of planes for three weeks.
Upon joining my first unit, I continued my professional development by obtaining my CCNA (Cisco Certified Network Associate) certification. Later, at my second unit, I earned the CYSA+ (Cybersecurity Analyst) certification, further strengthening my expertise in cybersecurity.
Outside of my military career, I have been trading options since 2020. Unlike many traders who start with paper trading, I learned through real experience—facing setbacks, refining my strategy, and ultimately achieving success. Now, while continuing my role in the 82nd Airborne Division and working in cybersecurity, I also trade options and share my insights on Substack. Through my platform, I educate others by sharing lessons learned, strategies, and ideas to help them navigate the world of options trading.
My journey has been defined by adaptability, resilience, and an eagerness to learn—qualities I bring to every challenge I take on.
The PIMM Trader is packed with stock ideas and charts to help you plan your next trade and grow your wealth!
Tell us about your publication?
My publication, Dream.Trade.Retire, is all about teaching people how to trade, shift their mindset, and explore new ideas and strategies. I don’t just share trade ideas—I also document my wins, losses, and break-even trades to provide real, transparent insights. My goal is to help others avoid the same mistakes I made when I first started trading.
What makes Dream.Trade.Retire unique is that I focus on using free platforms and indicators, proving that profitability doesn’t require expensive, advanced tools. I’ve learned to trade successfully without them, and I want to show others that they can do the same.
The publication is still in its early stages, but I have big plans for it. I understand that most people, like myself, have jobs and responsibilities outside of trading, so I’ll be adding a swing trade section soon to accommodate those who can’t monitor the market all day. The chat feature is dedicated to morning watchlists and intraday plays, while the main posts focus on education, strategies, and overall market knowledge.
Ultimately, Dream.Trade.Retire is about empowering traders with the tools, mindset, and insights they need to become successful—without unnecessary complexity or expensive resources.
Can you describe your investment style?
My investment style is a mix of strategic planning, risk management, and adaptability. I primarily trade options, focusing on high-probability setups while keeping risk tightly controlled. I believe in letting the market show me opportunities rather than forcing trades.
I don’t rely on paid indicators or expensive tools—I’ve learned to trade profitably using only free resources and a deep understanding of price action, technical analysis, and market psychology. I analyze trends, momentum, and key levels to structure my trades, and I always have a clear entry, exit, and risk plan before executing.
Risk management is a huge part of my strategy. I accept that losses are part of the game, but I minimize them by sticking to a disciplined approach—cutting losers early and letting winners run when the opportunity presents itself.
Since I know many traders have full-time jobs, I trade in a way that aligns with different lifestyles. I mix short-term intraday trades with swing trades, allowing flexibility for those who can’t be glued to the screen all day.
At the core, my investment style is well-rounded but focused on consistency, patience, and always learning. I share this mindset in my publication, Dream.Trade.Retire, to help others develop a sustainable, profitable approach to trading.
The PIMM Trader is packed with stock ideas and charts to help you plan your next trade and grow your wealth!
How do you find the investments you want to invest in?
I start by analyzing a company's financials, primarily using Yahoo Finance. Profitability is a key factor for me, but I also look at unprofitable companies if I see strong future potential. In those cases, I want to see them losing less money year over year or quarter over quarter, showing signs of improvement. While I do invest in these types of companies, I only allocate a small portion of my portfolio to them since they carry higher risk—but if my analysis is correct, they can yield significant returns.
My main focus, however, is on already profitable companies. Once I’ve identified a solid investment, I move to technical analysis. I look for my specific setup on the charts, create a plan and a backup plan, and evaluate potential outcomes for both the upside and downside. Risk management is crucial, so I always measure the risk-to-reward ratio before entering a trade.
One of the biggest lessons I’ve learned is to avoid FOMO (fear of missing out). Instead of chasing a trade, I wait for my setup, set alerts, and look for put opportunities or pullback entries if I miss the initial move. This disciplined approach helps me stay patient, manage risk effectively, and take trades that align with my strategy rather than emotions.
How do you reduce your risk?
Easy—have a stop loss. Risk management is everything in trading. I keep it simple: I buy calls at the lows and puts at the highs, always making sure I have a well-defined exit strategy before entering a trade. I also follow a strict rule: I take up to five trades in a day. If I lose two of them, I close my laptop and walk away—no revenge trading, no forcing setups. On the flip side, if I hit a home run on one of those trades, that’s it for the day. I might come back later to analyze charts and prepare for tomorrow, but I won’t take any more trades.
This disciplined approach keeps me from overtrading, helps me protect my capital, and ensures that I stay in control of my emotions rather than letting the market dictate my actions.
The PIMM Trader is packed with stock ideas and charts to help you plan your next trade and grow your wealth!
When do you sell?
Generally, a 15%-30% gain is good enough for me. With options contracts, that’s relatively easy to achieve. Think about it—if a high-yield savings account gives you 4% in a year, why wouldn’t you lock in a 15%-30% gain in a day?
I also look at it from a time perspective. Some people work eight hours to make $200, yet I see traders hesitate to lock in that same $200 in under 30 minutes. That mindset can be dangerous. Taking profits is just as important as entering a trade. If I’m holding multiple contracts, I like to shave off some profits along the way and let the runners go. That way, I’m securing gains while still giving my trade room to maximize potential.
What is your most memorable investment whether good or bad?
Woah! This takes me back—to my very first day trading a penny stock. Looking back, I highly recommend not doing what I did, but here’s what happened:
I full-ported my entire account into a penny stock that was going parabolic. This thing was halting multiple times, and I had no idea what was going on or even what the company did. I just saw it ripping up, and I yeeted everything into it. That was the first time I ever made a 140% gain in minutes, and it completely changed my mindset on life. I had just made my salary in a few moments, and I couldn’t believe this was real. I lowkey got upset because I had a real job at the time and it was like the computer just said "Fuck you, I’ve been here the whole time."
Sorry PIMM =)
But then reality hit—massive losses followed. I didn’t know what I was doing. That experience taught me one of the biggest lessons in trading: fast gains can disappear just as quickly if you don’t have a strategy. That moment made me want to become a serious trader, but it also humbled me.
The PIMM Trader is packed with stock ideas and charts to help you plan your next trade and grow your wealth!
What advice would you give your younger self?
Start early. The sooner you begin, the more time you have to fail, learn, and grow. Every mistake is a lesson, and every lesson brings you closer to success. There will be ups and downs, but one day, you’ll look back and realize you’ve been on one hell of a journey—and every step was worth it.
Before You Go
Thanks to
doing the interview. If you liked the interview, please consider giving the post a like and subscribing to Dream.Trade.Retire.I’d love to have you as a guest on the Investor Round-Up! Just send me a message and I’ll be happy to feature you.
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Disclaimer: The author of this post is not a financial advisor. The views of the guest do not represent the views of The PIMM Trader or its affiliates. The information provided herein is not financial advice and should not be construed as such. This content is intended solely for educational purposes and should not be used as a basis for any financial decision-making. Investing involves risk, including the potential loss of your invested capital. Only invest what you are willing and able to lose.