Long Time Trader: Richard Weissman
A Conversation with a Market Veteran
On this episode of the Market Mamas podcast, I had the pleasure of chatting with Richard Weissman, a professional trader who's been in the game since 1987 — long before most of us knew what a candlestick chart was.
Starting just before the infamous Black Monday crash, Richard's journey has been anything but smooth — and that's what makes his story so valuable for new and growing traders.
Lesson #1: Risk Management is Everything
Richard learned early that surviving bad trades is more important than chasing great ones. He uses a risk-tier system that caps losses per trade (typically 2%) and across correlated positions (like equity indices or forex pairs).
For traders who think multiple positions = diversification, he offers a key reminder:
If they move together, you're not really diversified.
Lesson #2: Build Systems You Can Trust
Rather than guess or gamble, Richard treats trading like running a business — with models, structure, and logic. His focus is on:
Positive expectancy strategies
Strict risk limits
Backtesting to build confidence in the system
He compares it to how casinos work: edge + control + scale = long-term profits.
Lesson #3: Scaling In ≠ Averaging Down
One debatable misconception many traders have is that adding to a losing position is always bad. Richard clarified that intentional scaling into a trade — within your risk rules — is a strategic way to build a position during market pullbacks.
The key? Plan your full position size before you enter, and stick to your stop-loss.
Lesson #4: It’s a Long Game — Keep Showing Up
Richard didn’t make money right away. He taught, studied charts, and worked in commodities before becoming consistently profitable. His advice to new traders:
Learn from your losses
Respect the learning curve
Stay in the game long enough to improve
Every great trader started with red days and doubt. The ones who make it? They don’t quit.
"You’re paying the ante to see the next hand. Don’t stress about it — that’s just the price of admission."
~ Richard Weissman, author of Trade Like a Casino
Two Core Beliefs That Shape His Strategy
When asked what helped him early on, Richard shared two foundational beliefs that still drive his trading today:
1. Markets Trend — and That’s Where the Edge Is
Not always, but when they do trend, they often offer the best risk-reward opportunities.
You don’t have to guess when a market’s trending — you can usually see it. Nasdaq, gold, and silver in October 2025? Obvious uptrends.
The key?
Don’t fear missing the early move. Risk small (e.g. 2%) and accept that if the trend continues, your upside is much greater than your downside.
2. Low Volatility = Future Breakout
Consolidation phases can feel like nothing’s happening — but that calm often comes right before the storm.
When markets get too quiet, with everyone agreeing on “fair value,” it creates an unstable equilibrium. One unexpected event can trigger a sharp move — and if you're ready, that breakout can be your edge.
Weissman's entire trading approach boils down to this:
Ride trends when they’re happening
Trade breakouts from long consolidations
If it’s a false breakout? Risk is limited.
If it’s real? The payoff can be massive.
Know When Not to Trade
Richard also distinguishes between short-term vs. long-term consolidations:
Long-term consolidation? He waits patiently for a breakout.
Short-term consolidation within a bigger trend? He might trade with or against the move, depending on the setup.
The idea is to trade in context, not in isolation.
The Biggest Reasons Traders Fail
Weissman broke it down clearly:
❌ 1. Ignoring Risk Limits
Many traders act like gamblers — telling themselves they’ll break their rules “just this once.”
But once you start doing that, your system (and your account) is already breaking down.
❌ 2. System Hopping
You create a working system, hit a cold streak, and then abandon it — only to watch it work again later.
Sticking with a solid, backtested model through ups and downs is key. As Richard says:
“There are a thousand ways to trade — just pick one and master it.”
Build a System That Fits You
Instead of trying to copy others, Weissman encourages traders to:
Define your time horizon
Know your personality and lifestyle needs
Build a model that aligns with both
You don’t have to be a scalper if you prefer longer holds. The market rewards consistency and self-awareness, not mimicry.
Keep Learning — Just Like a Casino Would
In his book Trade Like a Casino, Weissman lays out a repeatable framework:
Look for asymmetric trades (small risk, large reward)
Accept losses as the cost of playing
Build models with a positive edge — and stick to them
Markets are inefficient more often than people think — the edge is real if you’re looking for it.
*** Get your copy of Trade Like a Casino today: https://amzn.to/4oha4TI
Psychological Tip: Think Like a Professional
Weissman shared a great mental reframe for dealing with losses which I loved so much:
“You’re paying the ante to see the next hand. Don’t stress about it — that’s just the price of admission.”
You can’t trade without risk. Accept it. Manage it. Respect it. And keep showing up.
Final Thought: Stay Curious, Stay Sharp
Complacency is dangerous in trading. Even small refinements — like improving your exits or sizing more efficiently — can make a big impact over time.
“If I can go from 18.35% to 18.65% annually without compromising my system, why wouldn’t I?”
That mindset — consistent, curious, and calculated — is what separates a trader who survives from one who thrives.
🔗 Connect with Richard:
👉 LinkedIn: https://www.linkedin.com/in/richard-weissman/
👉 Email: richard@weissmanconsulting.com
Conversations with other traders are so valuable for me to have, and hence are such a gift for me to be able to bring to the public in this way. I really enjoy learning together from like-minded professionals and helping each other with tactics and tips that can help us all level up maybe just a bit quicker! Thank you Richard for being my awesome guest!!
If you find value too, please do like and subscribe to the podcast on whatever platform you caught this conversation on and let’s evolve together into the highest profitability!! And if you are considering being a guest on my podcast we well, reach out and let’s talk!! https://www.market-mamas.com/contact Take care and happy trading!