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This will be the first-ever trading challenge of my 42-year career.
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 over the next six months.
So I want to make sure the right people see this and join me before it’s too late.
This new trading challenge is inspired by the hit game show Who Wants to Be a Millionaire?
Around the turn of the millennium, it 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?
Instead of contestants answering questions, we’d climb the money ladder using option trades. We’d start with a small stake. Then, we’d roll the proceeds of each successful position into the next trade until that “small stake” became one million dollars.
A Better Way to Climb the Money Ladder
As longtime readers will know, 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 recently went through the track record of my newsletter recommendations. And across nine years and 381 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 are still low of hitting $1 million. 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 person with a few thousand dollars they can afford to lose, it’s worth a real attempt.
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’ll start off with a small stake and try to turn it into $1 million in no more than 12 trades.
The Challenge is open to everyone. Though, you’ll have to decide for yourself if it’s appropriate for you.
I’ll unveil everything about how it works at the event next Thursday, May 14 at 10 am ET.
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 I’ll get into the specific guardrails I’m building into this Challenge to limit downside at every rung of the ladder.
You can reserve your seat here, free of charge.
And if you sign up to be a VIP, you’ll get free access to my convergence and divergence tool, as well as access to my exclusive Delta Direct blog until the day of the event.
I look forward to seeing you there.
Best regards and good trading,
Jeff Clark
Editor, Market Minute
P.S. Windows like the one we’re in don’t stay open. The 2019 setup lasted a few weeks. The 2021 window closed in less than six. By the time most folks are sure the conditions are right, they usually aren’t anymore. That’s why I’m doing this now. Reserve your seat here.