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Around the turn of the millennium, Who Wants to Be a Millionaire was the most popular show on TV. At its peak, it ran four nights a week – drawing more than 35 million viewers an episode.
Contestants sat in a “hot seat” across from the host and worked through 15 multiple-choice questions of increasing difficulty to win a top cash prize of $1 million.
The stakes started out small, and you climbed the money-ladder with each correct answer. Get all 15 trivia questions right in a row, and win $1 million. Miss one along the way, and the winnings fall back to a stepped-up safety net – or to zero.
Roughly 10,000 people have been contestants on Who Wants to Be a Millionaire. Of those, only 12 individual winners and three teams have ever claimed the $1 million prize. So, the odds of success were low – less than 0.2%. But, it was possible. Some people did indeed become millionaires on that show.
And, it got me thinking…
What if I created a trading version of that same challenge?
So I did. Back in May, I launched my first-ever trading challenge. And it’s been a hit with participants…
Take it from Andrew C., who wrote to tell me: “Very good outcome … Followed the position size recommended…. about 150% gain. … A few more trades like this will soon see us into serious profits, so many thanks and please keep it going.”
And Warren, who said: “All told, we’re loving this! And, you are certainly dispelling the myths and fear mongering, while teaching a confident, conservative, and safer approach to Options Trading!”
So, I’m opening up access to this challenge again for a short time, by popular request…
A Better Way to Climb the Money Ladder
Instead of contestants answering questions, we’re climbing the money ladder using option trades. We start with a small stake, then roll the proceeds of each successful position into the next trade until that “small stake” became one million dollars.
And the results so far have been telling. At writing, here’s where the challenge trades stand:
We’ve closed three winners, one loser, and our last is still open (we didn’t post that trade to protect our participants’ investment, but at writing, it’s a winner).
To be clear, this isn’t how I typically trade.
I’m a conservative, low-risk trader. I use options to generate income and to make low-risk speculations. I like to take my profits off the table rather than letting them ride. This strategy has kept me in the options game for more than four decades.
There aren’t many options traders who can claim that sort of longevity. And, it is mostly due to my conservative style of trading.
But, one of my team members went through the track record of my newsletter recommendations. And across nine years and nearly 400 closed trades, there were 36 separate streaks of three or more winning trades in a row. Twenty-one of those streaks ran five trades or longer. Eight ran for eight trades or more.
And on two occasions, the streaks were long enough that – if you’d rolled a $5,000 stake from one trade into the next – you would have crossed the $1 million mark.
The first was during the 2023 banking crisis. Nine trades that could have turned $5,000 to $1.3 million with a rollover strategy.
The second was during the AI repricing of 2025. Twelve trades that could have $5,000 to $2.6 million.
The timing of those two streaks wasn’t coincidence. On both occasions, market conditions looked a lot like what we’re seeing right now: high volatility, broken assumptions, stocks moving 20% or 30% in a single session, sectors getting repriced overnight as the rules of normal investing temporarily stopped applying.
I call those moments disruptions. They’re rare, they don’t last long, and they’re the only environment where a roll-over strategy like this has any realistic chance of working.
And we’re in one now.
So, I figured: Why not? If there was ever a good time to take a shot at turning a small amount of money into a $1 million nest egg, this is it.
I Hope You’ll Join Me
The odds of hitting $1 million are low. I want to be clear about that.
Even in the best conditions I’ve seen in four decades, this requires favorable markets, disciplined execution, and some luck. Any trading carries real risk of loss. The money you use for the challenge should not be money you rely on to put food on the table.
But for the right reader – someone who can afford to put $5,000 at risk and follow a defined sequence of trades – it’s a chance to turn a small stake into a meaningful part of your nest egg.
And even if we don’t hit the full $1 million, the trades themselves are designed to produce gains along the way. A participant who follows the sequence and stops halfway through with $50,000 or $100,000 from a $5,000 starting stake hasn’t failed.
They’ve still done what almost no buy-and-hold strategy could have done over the same window.
That’s why I created the 12 Trades to $1 Million Challenge. We start off with a small stake and try to turn it into $1 million in no more than 12 trades, all while learning about the power of trading.
The Challenge is open to everyone. Though, you’ll have to decide for yourself if it’s appropriate for you.
I’ll walk through both of the prior $1 million rollover streaks trade by trade. I’ll show you why buy-and-hold is finished as a strategy for the next decade.
And if you decide to join the challenge, know it’s not too late. You can start at our next trade on the ladder, and you’ll get your full 12 trades, so you can have your shot at making it to $1 Million.
I look forward to continuing this challenge with you. Check it out right here.
Best regards and good trading,
Jeff Clark
Editor, Market Minute
P.S. This challenge is the perfect way to dip your toes into options trading, too. Take it from Hannah, who wrote in to tell me: “This was my first options trade ever and I made $1600 in profit! Which is a ton of money for me to make extra in a week. … I’m so excited to see how the rest of this challenge goes and to learn so much. Thank you!”
You can get started with the challenge by going right here.