Most Traders Watch Price. I Spent 28 Years Watching One Thing They Never See.

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Sixteen years ago, I lost my job.

For decades, I had helped the biggest hedge funds and investment banks in the world profit from the most lucrative options flow trading hands in the markets.

And then in one fell swoop, it all nearly ended.

Let me back up and tell you the whole story…

Back in 1997, I got my break on the Chicago Mercantile Exchange (CME) floor – that’s the world’s largest options and futures exchange.

It was the early days of Globex. The pits were still packed, but the future was moving to digital screens and high-speed internet.

Speed became everything. If you couldn’t execute trades faster than the next guy, you were toast.

But by 2003, volatility dried up. I knew the easy money was gone. So I made my move…

That’s when I got recruited to a bond prop firm. That simply meant we used our own money instead of managing client funds. It was high risk/high reward.

The Fed was gearing up to move rates. I could see what was coming – bond volatility was about to explode.

So I positioned myself right in the middle of the wildest bond markets we’d seen in decades.

In 2008 alone, I made over $4 million trading volatility. I was riding high during one of the biggest bull markets in a generation.

But then the Financial Crisis happened – and disaster struck.

That bond prop firm I mentioned? We faced a potential catastrophe with just one trade.

Our firm had $32 million in capital, and a single oil trade put $15 million at risk.

Worse still, I couldn’t do much about it. The trader was the majority owner. And he didn’t want advice from someone he considered less experienced.

That trade went bad. In fact, our capital dropped from $32 million to $18 million overnight.

It was a huge loss… And it wasn’t just the firm that was doing badly.

The stress of my job was overwhelming me. I’d developed constant headaches and even ended up in the hospital a few times.

It seemed clear that I wouldn’t last too long with the way things were going.

And then a few years later, another big change happened.

In 2011, the proprietary options trading firm I’d been a partner at for seven years was sold to a billion-dollar hedge fund. And I found myself suddenly out of a job for the first time in years.

Now don’t get me wrong – I wasn’t hurting financially.

I’d certainly built up enough capital to retire comfortably.

But the uncertainty of what comes next was eating at me. I’m someone who thrives on hard work and being where the action is.

Instead of jumping back into another trading firm, I decided to take it easy. I spent more time with my family.

And I decided to pursue some dreams I’d put on hold. I even trained for and completed the Wisconsin Iron Man 140-mile triathlon.

It all felt great.

But I knew I still wanted to be where the action was. Now, I wasn’t interested in going back to the 18-hour days and mind-numbing calculations of my old job. That’s not what I loved most about trading.

My true passion was using my knowledge to help others get ahead in the markets.

I missed the daily learning and the insights I could share with friends and family. I wanted to take that next step beyond just helping institutional traders fatten their wallets.

Just when I was at my most uncertain, an opportunity came along that changed everything for me…

How I Got Back in the Game

My friend Bob was one of the best option traders in Chicago. In fact, he was one of the most successful option traders in the history of the Chicago Board Options Exchange (CBOE).  

Now keep in mind: The CBOE is the world’s biggest options market. He wasn’t playing with Monopoly money here. He was making markets with the biggest players in the game.

So one day, I got up the courage to make a bold proposition to my old friend:

Hey, let’s make a deal. 

You show me your options-trading system.   

And I’ll agree to become your student.  

I really wanted that knowledge. But I didn’t want to work for another firm for years. I didn’t need the stress.   

So for the next six months, we played golf together, and he taught me his system on the side.  

I essentially worked for him for free.     

And after learning my mentor’s time-tested options strategy, we went after those big, consistent winners together.

But this time, things were different…

I ponied up about $250,000 of my own money. That’s no small feat… And believe me, I was sweating bullets. After all, I had a quarter of a million at stake in an extremely unpredictable market.

But I wasn’t worried for long…

Every day, we executed dozens of trades on the CBOE floor.

We were winning against some of Wall Street’s biggest firms – Goldman Sachs, Bank of America, Citigroup.

Just two regular guys going head-to-head with major institutions.

We made markets on about a hundred stocks. It was intense, profitable, and exactly what I’d been missing.

After all was said and done, we cashed out with a pretty sizable bank balance after a few years.   

And I retired – again. But this time, it was on my own terms.

Now I could play sports, trade my own money – literally do whatever I wanted.  

But you know what they say… Once a trader, always a trader.

Even after the big wins we scored together, I couldn’t stop myself.

After years of making money for the biggest players in the financial world, I’d found a new purpose in life.

I learned so much trading with my friend. And even more important, I got a crash course in how the markets could work for the little guy.

It seemed like a waste to keep all that valuable information to myself.

How You Can Trade Like the “Smart Money”

And that got me thinking…

What if regular traders had access to the kind of intel Bob and I used to make markets?

Now I’m not talking about your basic technical indicators or some time-worn market truisms.

That’s all noise…

If you want to know what real market makers – the smart money – are looking at, you need to track where institutional traders are placing their biggest bets.

It’s the same intel I used to leverage at the CME and that bond prop firm.

And it’s exactly what I highlight every day I go live on Masters in Trading. Because when you know the exact timing of massive options trades, you have the beat on where capital is really moving in the market.

That knowledge is exactly what can help us capitalize on big moves that most traders never see coming.

And for anyone looking to dive deeper into the signals and setups we discover every day…

 That’s exactly what the Masters in Trading Options Challenge is designed to teach.

I’ll take you step by step through the same process I use every day—finding opportunities, structuring trades with defined risk, managing winners, and protecting your capital along the way. No hype. No guesswork. Just a practical framework you can apply to every trade you make.

If you’re serious about becoming a better options trader, join me inside the Masters in Trading Options Challenge.  I think you’ll be surprised how quickly these concepts begin to click—and how much more confident you’ll feel every time you place a trade.

Remember, the creative trader wins,

Jonathan Rose

Founder, Masters in Trading

P.S. Most people think the biggest fortunes in technology are made after a company goes public. My InvestorPlace colleague Luke Lango thinks that assumption is becoming dangerously outdated — and the numbers back him up.

Luke has been tracing the playbook that’s been running Silicon Valley for nearly 70 years. It’s the same one that turned eight frustrated engineers and a $1.5 million bet into Fairchild Semiconductor — and eventually Intel. The same one that had a young Sun Microsystems co-founder write a $100,000 check to two Stanford grad students before Google had a single dollar of revenue. And the same one that turned a $75 million stake in a little-known AI startup called Anthropic into a position now estimated near $7 billion.

The pattern is accelerating. AI’s biggest players have decided it’s faster — and cheaper — to buy breakthrough technology than build it themselves. That shift is changing where the real money gets made. And Luke has spent years building a framework to spot the companies caught up in it before the rest of the market catches on.

Next Thursday, July 30 at 1 p.m. ET, Luke is going live to walk through that framework in full — including the one company he believes best represents this opportunity today.

Seats are limited. Register now and you’ll also get access to Luke’s VIP text list, where he’s sending a bonus report — “The AI Collectors’ Portfolio: 7 Stocks to Buy for the Biggest Tech Spending Boom of All Time” — free to anyone who signs up before Thursday.