Listen to the audio version of this article (generated by AI).
On November 19, 1999, a 31-year-old from Hampden, Connecticut, named John Carpenter sat in the hot seat in a New York TV studio and used his “phone-a-friend” lifeline on the final question of Who Wants to Be a Millionaire?
He didn’t need help. He just called his father to tell him he was about to win.
Carpenter became the first contestant to walk away with the $1 million prize.
The show was built around the simple idea of a money ladder. Start with a small stake, and climb one rung at a time until you reach $1 million.
Each correct answer doubles your money… but you only move up if you got the previous answer right. Miss one, and you fall back down a rung – or to the bottom – and the game is over.
There have been roughly 10,000 contestants on the U.S. version of Who Wants to Be a Millionaire? Only 12 individual winners and three teams have ever claimed the $1 million prize.
The odds of success were low – less than 0.2%. But, it was possible. Some people became millionaires by climbing that ladder all the way.
This idea of a money ladder got me thinking… What if I created a trading challenge built around the same idea?
And yesterday, several thousand folks joined me to check out my 12 Trades to $1 Million Challenge. I explained that, instead of contestants answering questions, participants would climb the ladder using option trades.
They’d start with a small stake. Then they’d roll the proceeds into each next trade until that small stake became $1 million.
If we hit the mark, great. If we don’t, we still have the chance of turning a small stake into a meaningful amount. And challenge participants would learn a ton about options trading along the way.
I explained that this kind of challenge isn’t for everyone. But, for someone who can follow a defined sequence of trades, it’s a chance to turn a small stake into a meaningful part of your nest egg between now and the end of the year.
If you couldn’t join me yesterday, you can check out the replay right here.
Conservative by Nature
It’s important to note that this is not how I typically trade.
I’m a conservative, low-risk trader by nature.
I like to use options to generate income and make low-risk trades. I always take my initial investment off the table if my trade sees 100% (or more) gains. That approach has kept me active as a trader for more than 42 years – and there aren’t many who can say that.
This kind of rollover strategy is NOT what I’d recommend in a normal market.
But, today’s market is anything but normal…
Earlier this year, Anthropic – the company behind the Claude AI model – announced a new security tool that could automatically scan code for vulnerabilities and suggest fixes.
Within days, three of the most respected cybersecurity companies – CrowdStrike (CRWD), Cloudflare (NET), and Okta (OKTA) – each lost close to a tenth of their value in a single session.
A few weeks later, a research firm called Citrini Research published a viral note about what AI was doing to the software industry. It argued that AI coding agents had erased a moat that protected enterprise software for two decades. What used to take a team of engineers and months of work could now be done by one person, in a weekend, for almost nothing.
Rare Market Disruption
Within 48 hours, roughly $285 billion was wiped from the value of seven popular software stocks.
Software-as-a-service giant Salesforce (CRM) lost as much as 30% of its value in 2026. Atlassian (TEAM), another enterprise software firm, is down nearly 58% in a single quarter. Even Palantir (PLTR) – a company so deeply embedded in the U.S. military that the Pentagon made its software an official long-term program – lost 15% in a week.
It’s not just AI. Last year, a single tariff announcement triggered an 11% drop in the S&P 500 in a matter of days – one of the sharpest declines in decades.
And we’ve seen stocks go on a rollercoaster as a result of the war with Iran.
We’re in a moment when the normal rules of the market temporarily break down. Stocks move 20% or 30% in a single session. Sectors reprice overnight. Blue-chip companies that should be steady start acting like speculative small caps, and companies that should be punished start ripping higher.
These windows are rare. And when they appear, they don’t stay open long. But they’re the exact conditions a rollover strategy is built for. That extra volatility is the “fuel” that options traders need to make meaningful gains.
Trading through one of these disruption windows doesn’t guarantee success. But it gives us the best shot possible at achieving our goal.
That makes now the perfect time for my Challenge.
Turning a small stake into a million will be tough. And we may not get there. But my track record shows it’s entirely possible.
We’ll start with a small stake and see if we can roll it into $1 million in no more than 12 trades, in six months or less.
Three things matter before you decide whether this is for you:
- The odds of hitting the full $1 million are low – I want to say that plainly. Even in the best conditions I’ve seen in 42 years of trading, this requires favorable markets, disciplined execution, and some luck.
- The Challenge is designed to cap your downside at the starting stake – you commit $5,000, and that’s your maximum loss. The whole structure is built so that even if every trade goes wrong, you don’t get pulled deeper.
- Even if we don’t hit $1 million, the trades along the way are designed to produce real gains – Stopping halfway with $50,000 or $100,000 from a $5,000 starting stake isn’t a failure. It’s a result almost no buy-and-hold strategy could match over the same window.
If you haven’t joined yet, there’s still time to check it out right here.
I can’t wait to show you more about how it all works.
Best regards and good trading,
Jeff Clark
Editor, Market Minute