How My Wife Turned Her Luxury Handbags Into a $75,000 Investment: Our Step-by-Step Playbook

It all started with a simple question.

My wife, who has a wonderful appreciation for luxury bags—the LVs, the Pradas, the ones that are as much art as they are accessories—saw me glued to my computer screen day after day. At the time, I was deep into my own investing journey, constantly talking her ear off about new strategies, my wins, and even my screw-ups.

One day, she turned to me and asked, "So, all that learning and experimenting… is it actually working? Are you seeing real money from it?"

I was always transparent, showing her the wins, the losses, and the whole messy truth. Slowly but surely, as I refined my approach, she began to see consistent, real money coming in from the stock market. She got curious.

Then came the conversation that changed everything. "You know," she said, "I've been thinking. What if I sold some of my bags? I want to put that money into the market, like you do."

So she did. She took about $14,000 from the sales of a few bags and we put it to work. Fast forward just a couple of years, and by using the specific strategy I'm about to share with you, that initial $14,000 has grown to over $75,000.

That's a life-changing return. It's the kind of result that makes people ask, "How is that even possible?"

In this article, I’m going to pull back the curtain and show you the entire playbook, step-by-step. We're going to break down the foundational belief, the essential ground rules, the exact strategy we used, and the critical mindset needed to achieve a result like that.

The Core Belief: Riding on the Shoulders of Giants

Before we touch a single dollar, we need to understand the fundamental belief that underpins this entire strategy. It’s a powerful idea that investing legend Warren Buffett has shared for decades: bet on the overall success of the best American companies.

The easiest way to see this is by looking at the S&P 500. If you’re new to this, don't worry—all the S&P 500 is is a single number that tracks the performance of the 500 largest companies in the US. Look at a chart of it over the last 50 years. You’ll notice an undeniable trend: despite all the wars, crashes, and recessions, it is always up in the long term.

Why?

Because when you invest in the broad market, you are riding on the shoulders of giants. You are betting on the collective brainpower of the world's brightest and most ambitious people—the scientists, engineers, and entrepreneurs inside these great companies. As they innovate, the entire market rises with them.

This leads to a simple choice:

1. Pick Individual Stocks: You can try to find the next superstar company. This offers huge rewards but comes with massive risk and requires endless research. It’s a high-stress game of finding a needle in a haystack.

2. Buy the Whole Haystack: You can invest in the market as a whole through something called an ETF (Exchange-Traded Fund). Think of an ETF like a single stock you can buy that holds all 500 of those top companies inside it.

For this strategy, we choose the second option. We use ETFs like SPY (which tracks the S&P 500) to simply buy the entire haystack. This allows us to focus on the market's powerful upward trend without the risk of a single company failing.

Step 1: The Three Golden Rules of Investing

With that $14,000 ready to go, the first thing we did was review the three non-negotiable rules for building wealth safely.

• Golden Rule #1: You Must Have Positive Cash Flow.

  • What it is: You must have more money coming in each month than going out.

  • Why it matters: If you're spending more than you earn, you're on a financial treadmill heading backwards. Trying to invest without fixing this is like trying to fill a bucket with a hole in it. It creates constant stress and can force you to sell your investments at the worst possible time.

• Golden Rule #2: You Must Have a Rock-Solid Emergency Fund.

  • What it is: 3 to 6 months of essential living expenses, sitting in an easy-to-access savings account.

  • Why it matters: Life happens. Your car breaks down, you get an unexpected medical bill. Your emergency fund is the financial firewall that protects your long-term investments from short-term problems.

• Golden Rule #3: You Must Be Free From High-Interest Debt.

  • What it is: Specifically, credit card debt.

  • Why it matters: This is pure math. Traditional stock investing might give you a 10% or 15% return in a good year. But your credit card is guaranteeing you a 20%+ loss every single year. It’s financial quicksand. Paying off high-interest debt is the highest, safest return on your money you will ever get.

Step 2: The Strategy—DCA on Steroids

With the foundation set, we moved to the strategy itself. It starts with a classic idea that Warren Buffett recommends to almost everyone: Dollar-Cost Averaging (DCA).

The biggest mistake investors make is trying to time the market—waiting for the "perfect" moment to buy. This is a losing game. Nobody can predict market tops and bottoms, and the bottom of the next crash could easily be higher than today’s prices.

DCA solves this. You simply invest a fixed amount of money at regular intervals, no matter what. This removes guesswork and ensures you consistently participate in the market's long-term growth.

But then, we give this simple idea a powerful twist. We supercharge it using a financial tool called an option.

Now, don't let that word scare you. Think of an option like putting a deposit down on a house. You pay a small fee today to get the right, but not the obligation, to buy the house at a locked-in price later on.

We do the exact same thing with stocks, using a special type of option called a LEAPS. It’s simply an option contract with a very long shelf life—typically more than a year.

Here’s an example of its power:

• Traditional Way: You invest $1,000 in a $100 stock, buying 10 shares. The stock rises to $120. Your investment is now worth $1,200. You made $200 (a 20% return).

• The LEAPS Way: You use that same $1,000 to buy one LEAPS call option. When the stock rises to $120, the value of your option contract itself is now worth roughly $2,000. You made $1,000 (a 100% return).

That is the power of leverage.

The Million-Dollar Question: What About a Crash?

This is where the real playbook begins. What do you do when the market plummets? Here’s the simulation I walked my wife through.

Imagine a portion of her money went into a LEAPS position that cost $1,800. The stock is at $100, so we buy an option with a $100 strike price (our locked-in purchase price).

A year goes by, and the market crashes. The stock plummets to $70. That $1,800 position is now only worth $300. This is where most people panic and quit. But a professional sees opportunity and goes on offense.

• Move 1: Manage the Position (aka "Holding On") If you owned a stock that crashed, you wouldn't sell for a loss; you'd hold on for the recovery. We do the same with options, but since they have an expiration date, we must actively buy more time. We do this by "rolling" the option: we sell our damaged contract for its remaining $300 and use that money (plus a net cost of $500) to buy a new one expiring two years further in the future. That $500 is the price we pay to keep the position alive.

• Move 2: Go on the Attack (DCA on Steroids) This is where we apply Dollar-Cost Averaging. With the stock on sale, we buy a new LEAPS contract, this time with a strike price at the crashed price of $70. Because it’s so close to the current price, this new option is incredibly powerful. A realistic cost is $1,600.

Now, let's fast forward 18 months. The market roars back, and the stock hits $130.

• The first contract we "rolled" is now worth $3,200.

• The second, aggressive contract we bought is now worth a massive $6,050.

The total value is $9,250. From a total investment of $3,900, the net profit is $5,350—a stunning 137% return. By going on offense during a crash, you don't just survive—you come out far ahead.

The Payoff: A Battle-Tested Plan

So there you have it. That is the entire playbook. The foundation, the strategy, and the mindset. It’s not a one-time trick; it’s a simple process we just repeat over and over again.

And it works. It’s how my wife turned that initial $14,000 into over $75,000. And she did it through real market turbulence—weathering significant pullbacks in 2023, international volatility in 2024, and even the ‘Trump crash’ of early 2025.

It’s the same approach that has allowed me to more than double my own net worth, and the same strategy that got me through the brutal, 8-month bear market of 2022. This is what’s possible when you stop guessing and start following a clear plan.

Now, my personal strategy is a bit more complex. I also actively sell options to generate consistent income, which is a powerful way to make money even when the market is flat. That’s a topic for another day (and another article).

But for most people, the LEAPS strategy discussed here is the most efficient path to significant growth. The most important thing is to simply get started. Because if no action is taken, none of this knowledge matters.