Podcast – Episode 201 – 50 Years of Lessons

Reaching age 50 is a humbling milestone. It’s a time to look back at the “front nine” and realize that while the past is written, the “back nine” is where the most strategic plays happen. On a recent episode of the Option Genius Podcast, our own Coach Matt sat down with Alan Sama to discuss a vital question: What are the biggest lessons from 50 years of life and 10 years of trading?

The journey from a “blackout period” at a retail job to the freedom of the laptop lifestyle isn’t just about learning a strategy; it’s about learning yourself.

Finding Your Trading Lane

One of the most common mistakes new traders make is trying to learn every strategy at once. Matt suggests that the secret to longevity is matching your trading “lane” to your personal temperament.

If you are a naturally laid-back person, why are you stressing yourself out with high-frequency 0DTE spreads? Matt’s preference for Oil Futures stems from its passive nature—it allows him to live his life without being tethered to a monitor. Conversely, if you crave action, a slower strategy might lead to boredom and “tinkering” with your rules.

The Golden Rule: “Don’t Be Cute”

In the Option Genius community, we have a saying: Don’t be cute. > “Being ‘cute’ is code for deviating from the rules you have in place. It’s saying, ‘I think I’m smarter than the market.’ You have your rules, but you think you can edge out a little more or bend them. It pretty much never ends well.” — Matt, Option Genius Coach

Whether you are trading a small personal account or managing a fund, the market rewards discipline and punishes “creativity” that lacks statistical backing.

The Costco Connection: Why Financial Power Matters

Matt spent 14 years at Costco, eventually driving a forklift and helping coworkers set up their 401(k) plans. He witnessed firsthand the struggle of older workers standing on their feet for eight hours a day because they felt they had no other choice.

This is why we trade. Wealth isn’t about the number in the bank; it’s about domain over your time. If you can learn a skill that generates even a few hundred dollars a month, you have more leverage than the person working 40 hours of overtime just to keep up with inflation.

Shortening the Learning Curve

If Matt could go back 10 years, he would have skipped the traditional financial advisor. Why? Because giving your financial power to someone else often means you stop “peeling back the onion.” By the time you realize an advisor isn’t acting in your best interest, you’ve lost years of compounding.

To get started properly, Matt recommends focusing on foundational resources:

• The Automatic Millionaire by David Bach: For understanding the power of automated compounding.

• The Intelligent Investor by Benjamin Graham: For a conservative (though sometimes dry) look at value.

• Passive Trading: Alan Sama’s roadmap for generating income without the Wall Street “rigged” system.

Conclusion: If Not Now, When?

Whether you are 20 or 50, the biggest risk is staying exactly where you are. If you aren’t happy with your financial trajectory, you must change the input to change the output. Give yourself three to six months of dedicated study. Paper trade. Learn the mechanics. Most importantly, stop making excuses.

Podcast Episode Transcript

50 Years of Lessons: A Special Birthday Interview with Coach Matt

Allen Sama: Today we have a very special show. We are celebrating a major milestone—I wanted to wish Coach Matt a very, very happy 50th birthday!

Matt: Thank you. I didn’t tell anybody on the coaching calls, but yes, hitting that 50 mark is very humbling.

Allen: So, you’re 50. How long have you been trading now?

Matt: About 10 years. And I’ve been with Option Genius for about four.

Allen: What would you tell our audience? What are some of the biggest things you’ve learned over this time?

Finding Your Lane and Your Temperament

Matt: The first thing I would say is: don’t be in a rush to learn everything all at once. You are learning wonderful skills that can change your life, but you really need to take the time to find out what kind of trader you are.

Try to match your temperament to your strategy. It’s a new world when you get into it—you want to do every trade you hear about—but you have to find your lane. Are you the type of person who should be trading Oil futures, or 0DTE, or 30-day trades? Be forthright with yourself about who you are. Take the risk assessments. Sometimes you think you are a certain way, but trading reveals who you really are over time.

Allen: How do we figure that out?

Matt: Pay attention to which strategies come easier to you. I see people get into an oil program, for example, and it’s wonderful, but it’s too slow for them. They gravitate toward “Market Power” or credit spread weeklies. Specifically, pay attention to whether a strategy matches your temperament or if it’s just being difficult for you.

Allen: What type of trader are you?

Matt: I’m geared toward Oil futures. It epitomizes passive trading. It’s a trade where you know your parameters, and you can go on with your life without checking the trade constantly. It matches my temperament because I’m a very laid-back person. Sometimes I wish I were more boisterous, but I have to be true to who I am.

Learning from the “Big Loss”

Allen: What about your biggest loss?

Matt: That was in “Market Power.” It was in the fund, so in dollar terms, it was the biggest because it was the biggest account.

Allen: Was that the one where you went on vacation and left me to deal with it?

Matt: My biggest loss was your loss? Is that what you’re saying? We have this thing at Option Genius where whenever I go on vacation and hand it off to Allen, the market goes crazy.

Allen: What did you learn from that big loss?

Matt: That it is okay. Nothing is the end of the world. We dream up worst-case scenarios in our minds; we feel like the world is going to end. That is not true. Our minds can play tricks on us, making us wish we could go back in time. That doesn’t serve you.

It’s good to reflect on where you went wrong, but do it positively. Don’t beat yourself up. I’m very hard on myself, but I’ve learned that doesn’t serve where I’m going. You gain from your losses. That is how you grow. We learn from our failures.

Allen: That’s huge. I like to tell people: think about the issue you are dealing with now—even a big loss. Five or ten years from now, is it going to make a difference in your life? Most likely not. You recover.

Matt: Exactly. Even at the fund, we had that loss and we recovered. We had other strategies that were working. It’s a team effort. Every strategy is a team member. “Market Power” was pulling its weight, then it had a loss, and the other team members pulled through. Trading teaches you everything about yourself—your risk level, your state of mind, and how you react to loss.

The Golden Rule: Don’t Be Cute

Allen: What was that other one-liner you came up with?

Matt: “Don’t be cute.” That became one of our rules. “Being cute” is code for deviating from the rules you have in place because you think you’re smarter than the market. You have your rules, but you think you can edge out more or bend them. It pretty much never ends well. Don’t throw in a new strategy you just heard about on YouTube in the middle of a trade you’ve never tried before.

Biggest Win and Explaining the Job

Allen: Biggest win?

Matt: The compounding of wins. Getting consistent is the real big win. Looking at a series of six months or a year and seeing that I’ve proven to myself that I can do this.

Allen: When people ask what you do for a living, what do you say?

Matt: I tell them I teach everyday people how to make money in the stock market. If you get too specific too fast, people zone out. But if you say you teach people how to make money, they get interested and ask, “How do you do that?” Then the conversation takes care of itself.

Starting Over: Shortening the Road

Allen: If you could go back 10 years and start over, knowing what you know now, what would you do?

Matt: I would skip the financial advisor. I would have cut that whole part out. I was young and I gave my power away to someone else because I thought they were smarter than me.

If I went back, I would go deeper. Trading is like an onion; you have to peel it back. I would have looked at more ways people were actually trading and made decisions quicker rather than spending so much time in one area. I wouldn’t rely on just one person; I’d take in the totality of many smart people.

The Books That Matter

Allen: You have a lot of books behind you. Which ones helped you?

Matt: The Automatic Millionaire by David Bach. That started my whole path. Before that, I didn’t even care about my finances. My sister gave me that book. It made sense to me—the miracle of compound interest. It taught me that I could save a few dollars a day, put it in an account, and it would grow over time.

I also look at Ray Dalio’s Big Debt Crisis for the macro view. I like to take at least one good thing from every book I read.

The Costco Journey: From Forklifts to Freedom

Allen: You worked at Costco for 14 years. What did you do there?

Matt: I was a property manager in Boston before that—a high-pressure, stressful job dealing with boilers breaking and fire escapes. That experience is why I’m so calm today. I’ve seen it all.

When I moved to Atlanta, I didn’t have a job yet, but I had a buffer. I was shopping at Costco and noticed everyone seemed so happy. I got a part-time job that turned full-time, and I eventually started driving a forklift. I loved it.

I realized that hourly workers often made more than managers and had more control over their time. I saw upper-level managers who made a lot of money but had no life outside of Costco.

Allen: And you left because of trading?

Matt: I did. While I was there, I was obsessive about learning. I’d use my 15-minute breaks to study trades. I wouldn’t even eat lunch; I’d just focus on how a trade worked.

I eventually became the “unofficial” 401(k) guy. Representatives from the investment companies would come to the break room, and word got around that I knew more than they did. Coworkers would find me in the building and ask, “Matt, how do I set up my 401(k)?” I loved helping the young kids because they were just given a pamphlet and had no idea where to start.

Why Trading Is Different from Gambling

Matt: Even if someone gave me $5 million today, I’d still trade. If I had zero dollars, I’d find a way to make $50 and trade.

Once you learn to trade consistently, there is no going back. It even ruins gambling for you! I used to love Las Vegas, but now I can’t even put a bet down. I know the odds. I look at people throwing money away at a casino and think, “Why would I do this? I’ll just go trade where the odds are better.”

The “If Not Now, When?” Philosophy

Allen: What advice would you give to someone following in your footsteps?

Matt: I’d ask: “Are you okay with things being the same?” Look at where you are right now. If you don’t see a way to be better in the next few years, give trading a shot.

Give yourself three to six months. Put in the effort. Your mind will tell you “Yeah, but…”—push that aside. It will open up a whole new world. I think back to the people I saw at Costco who were 70 or 80 years old, struggling to get through a shift on their feet all day. If they just knew a skill to make a couple hundred extra dollars, it would change their lives.

Allen: My wife told me once: “If you fast forward five or ten years and you still have this issue, how are you going to feel?” That’s when I realized I had to fix things now.

Matt: Exactly. If not now, when? We’re past the halfway mark. There’s more behind us than in front. If you don’t like your future, you need to change it now, otherwise, it will look the same or worse as you get older. Give yourself a chance.

Allen: Happy birthday, Matt. Thank you for everything you do at Option Genius.