Are You Up for This “Money Ladder” Challenge?
Michael’s note: We got a fantastic response yesterday to the launch of Jeff Clark’s first-ever trading challenge.
Jeff is one of our in-house options trading experts. And he’s aiming to harness the big moves we’re seeing in stocks this year – and turn a $5,000 stake into $1 million in 12 trades or fewer.
Think of it like a money ladder. Each rung is a single trade, and the winnings from one trade become the stake for the next – climbing higher with each rung.
More than 3,000 folks tuned in to Jeff’s launch. But there are still slots available to join Jeff and the other Challenge participants.
The odds of hitting $1 million are still low, as Jeff is quick to admit. But as he gets into below, in his 43 years as a trader, he’s seen only a handful of markets this favorable for an attempt like this.
Over to you, Jeff…
BY JEFF CLARK, EDITOR, MARKET MINUTE
The press dubbed it Software-Mageddon.
In January, the AI company Anthropic released a product called Claude Cowork.
It can create software on demand. A small business owner can describe what he wants in plain English and have a working program built for him in minutes.
Wall Street did the math fast. If businesses can create their own software for a couple of hundred dollars of AI subscription fees, why keep paying hundreds of thousands of dollars to the software companies?
The selling was brutal. Over $1 trillion in software market value was wiped out in a matter of weeks. Salesforce (CRM) – which makes the software companies use to keep track of sales – fell 45% from its high.
And it wasn’t alone. The iShares Expanded Tech-Software ETF (IGV)– which tracks dozens of America’s biggest software names – plunged 35% from its September high in just five months.
That’s a faster collapse than most investors will live through more than two or three times in a career.
Every pundit on every financial network was saying the same thing: AI is going to destroy the software industry.
I disagreed.
Not because I’m an expert on the software industry or AI. But because of what the IGV stock chart was telling me.
By Feb. 24, IGV was trading more than 20% below a key trendline called the 50-day moving average. In my 40-plus years of trading, this fund had almost never strayed more than 12% from that line before snapping back.
That morning, I told my Jeff Clark Trader subscribers to buy a call option on IGV. We paid $2.50 a contract.
Seven days later, we sold it for $5.50.
A 120% gain – in one week – on a sector everyone else had given up for dead.
And over the last year, I’ve given my subscribers the chance to make 13 other triple-digit wins and 51 double-digit wins.
Those are the kinds of gains you can make as an options trader during the disruptions we’re seeing in today’s market.
It’s why I’m so excited about that 12 Trades to $1 Million trading challenge I launched yesterday. These are ideal conditions for an options trader like me.
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This Is Not a Normal Market
The kind of move we saw in IGV doesn’t happen in a normal market.
In a normal market, a sector ETF doesn’t fall 35% in five months on the back of a single product announcement. Stocks don’t reprice 20% or 30% in a single session. Companies that should be steady don’t start moving like speculative small caps.
But this isn’t a normal market.
In a slow, grinding bull market, the kind of mean-reversion trade I took on IGV is hard to find. Stocks drift higher in a steady line. The rubber band never stretches far enough to snap. Most of my trades, in those years, are quiet doubles on quiet setups.
But in a disruption window – when stocks are moving 20% in a session and sectors are repricing overnight – the rubber band stretches far. And when it snaps back, it snaps back hard and fast.
That’s why I’ve issued the first-ever trading challenge of my career.
It’s built around the idea of a “money ladder.” We’ll start with a $5,000 stake. Then we’ll try to turn it into $1 million in 12 trades or fewer.
Low Odds, But Not Impossible
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 turned $5,000 into $2.6 million.
The timing of those two streaks wasn’t a 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.
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.
Here’s How We’ll Scale the Money Ladder
Like I said, I’m recommending challenge participants start with $5,000. But if $5,000 feels too steep, you can do this challenge with $500 or even $200.
Here’s how it works. Whatever you put into the first trade, we attempt to double it. We’re aiming for a 100% gain on each option trade.
So if you start with $500, it becomes $1,000. Then we exit that trade and move to the next one. The downside is that if we lose 50% on any given option position, we exit the trade as well.
We never want the entire account exposed to one position, and we never want to hit zero. So if we put $5,000 into the first trade and it gets cut in half, we’re down to $2,500 and we exit immediately.
Then we move to the sidelines and look for another opportunity.
Yes, there will be times when we cut a loss at 50% and the trade later reverses in our favor. That’s going to happen. But we can’t focus on hindsight.
The rules are simple – we enter an option trade, and if it doubles, we exit. If it gets cut in half, we exit.
If we’re correct and the trade doubles, that means we can lose two trades for every one winner and still break even. That’s a 33% win rate. Historically, we’ve done much better than that in my services over time, so I like the odds of this working in our favor.
I expect we’ll have the first trade recommendation out within the next few days. I’m waiting for a setup that I believe is a no-brainer before we jump in.
I’m not going to force these recommendations. If we sit in cash for a while, I’m perfectly okay with that because I want this challenge to be something we can look back on six months from now and say, “What a fantastic run that was.” Not only because we made money, but because we learned a lot, too.
I’m excited about what’s ahead over coming weeks and months as these disruptions roll on.
You can check out the full details of my challenge and how you can participate here.
Best regards and good trading,
Jeff Clark
Editor, Market Minute
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