James and the Giant Debt

Jason Williams

Posted October 6, 2023

The past few weeks, I’ve taken a break from writing about specific companies or economic trends to give you a little more background about the journey that led me from the back rooms of Wall Street to the front yards of Main Street.

We’ve talked about my education and some of the illustrious professionals who mentored me as I completed my degrees in finance and economics.

We’ve strolled down Wall Street as I worked my way up the ladder at one of the world’s biggest institutional investors, Morgan Stanley.

We’ve even taken some detours down the dark alleys where I learned about the collusion rampant among the financial, political, and journalistic elite.

But I often find that the most compelling stories are those rooted in adversity, resilience, and transformation.

And today, in a continuation of that “series” on what led me to become Main Street’s biggest advocate, I wanted to share a truly remarkable story of just such adversity, resilience, and transformation.

It’s about one of my early clients and how together we transformed his financial situation, allowing him to move past prior mistakes and carve out a brighter future.

In order to “protect the innocent,” let’s call my friend James (which is not his name but lends itself to that incredible title I used today).

His journey, filled with ups and downs, might echo the experiences of many. So I'm sharing it not just as a testament to his determination but also to highlight the transformative power of sound financial guidance.

I also want to tell it because, since James' story might resonate with many currently facing financial uncertainties (which seems to be most of us in these trying economic times), I believe it can bring hope, as well.

Slowly at First, Then All at Once

You see, at a young age, James was drawn to the allure of the stock market.

James' early endeavors in the markets were much like a roller coaster — thrilling highs but equally devastating lows.

Like many investors, he was drawn to the allure of high returns and started placing bigger and bigger bets on risky assets…

But, also like many investors, he didn't have a strategy at all and was investing based on his emotions — a recipe for almost certain disaster.

But he was doing OK, and the thrill of those wins was enough to keep his account flush and his adrenaline pumping for a few years…

Until a series of ill-informed trades brought him to a financial abyss. He lost everything he’d made plus most of his principal, too.

Then the great financial crisis of 2008/2009 hit and James thought he’d found his redemption…

As markets plummeted, he used what little money he had left to take on short positions and bet against the stock markets.

And he made significant gains by shorting the market through 2009. In fact, he almost got himself back to even.

But as all investors know, timing the market's peaks and troughs can be a treacherous game.

And as bullish sentiment returned, James continued to bet against the market, ultimately leading him to a devastating loss.

You see, when you buy a stock, you can only lose 100% of your investment, but when you short a stock, your potential losses are infinite.

And James found that out the hard way. By the time he was able to close out his last ill-timed short trade, he’d incurred a massive loss and was looking at a margin debt owed to the bank of more than $100,000.

Now, I probably don’t have to tell you this, but to a twenty-something, that’s insurmountable and feels like it’s going to burden you forever.

And that’s pretty much how James seemed to feel when he first approached me to talk about his dilemma.

He was laden with heavy margin debt to the bank and burdened with regret. He said he worried that he’d never really be able to recover from it.

But that’s not the whole of it. Not even in the least…

The Sins of My Father Son

There's an old adage that says, "It takes a village."

And in the world of finance, sometimes it's not just an individual's journey but an entire family's.

That’s where James’ story takes a poignant turn…

The weight of his financial decisions wasn't solely his to bear.

His parents, who believed in his vision and potential, had co-signed his investment account so that he could take on those margin trades.

This meant that not only was James' financial future at risk, but his mistakes also threatened to derail his parents' retirement dreams, too.

And the guilt of potentially ruining his parents' golden years was a burden even heavier than the financial debt.

I’m serious when I say that when James first walked into my office, the weight of his financial mistakes was palpable.

But despite all the doom and despair I saw in his face when we first talked about his situation, what struck me most was his determination to change his financial future.

And when he approached me, it was with dual objectives: to salvage his financial position and to ensure his parents' retirement wasn't compromised.

A New Game Plan

So together, we took a long, hard look at his current financial situation. And we crafted a multi-pronged strategy…

Recognizing the need for a change, I designed an investment strategy for James that would help him pay off his debt, recover his losses, and remain well within his risk tolerance. 

Here's the approach we took:

  1. Holistic Financial Analysis: We started by dissecting his entire financial landscape — his assets, liabilities, income streams, and expenditures.
  2. Diversification: I emphasized the importance of not putting all eggs in one basket. We allocated his investments across various asset classes, ensuring stability and growth potential.
  3. Income-Driven Assets: Recognizing the urgency to clear his debt, we targeted assets that promised consistent returns and dividends. This not only provided a steady cash inflow but also bolstered his portfolio's overall health.
  4. Strategic Market Plays: Leveraging insights from my years in the industry, we took calculated risks, investing in sectors and industries poised for growth, always keeping his risk tolerance at the forefront.

A Future So Bright You’ve Got to Wear Shades

Fast-forward to today and the results are nothing short of miraculous…

Within a few years, James not only cleared his enormous debt but also rebuilt his portfolio, surpassing its previous peak.

And the cherry on top? James finally opened the doors to his very own restaurant — a lifelong dream he once considered unattainable.

At that “grand opening,” James pulled me aside to thank me (again) for helping him.

And he told me something that’s stuck with me all these years later and still brings a tear to my eye and a smile to my face when I think about it. He said:

Jason, I was drowning, and you threw me a lifeline when nobody else would. I was on the brink of losing everything — both my future and my parents' future. The guidance you provided didn't just save me; it saved my whole family. I honestly never imagined being free from that debt, let alone achieving what I have today. And I feel like I owe it all to you.

But here's the thing: James doesn’t owe it all to me…

I can only give suggestions and help create a strategy for success; he was the one who had to implement everything in his own life.

It was his determination to stick with those strategies that really led to that success.

And financial redemption isn't exclusive to James, either. It's not magic — it's simply about having the right strategies in place and sticking to them.

With the right guidance, strategy, and mindset, it's attainable for everyone.

So if James' story touches a chord…

If you're navigating through your own financial challenges…

Or if you're striving for a brighter financial future…

I warmly invite you to join me and the tens of thousands of investors already taking the reins of their own financial future in our flagship investment community, The Wealth Advisory.

Here, we don't manage funds…

We transform financial destinies, whether you're at the beginning of your investment journey, navigating through debts, or looking to optimize and grow your wealth.

Just remember, your past doesn't define your financial future and it’s never too late to redefine your financial narrative.

With the right strategies, guidance, and determination, the road ahead can be brighter than you ever imagined.

And together, we can chart a path filled with prosperity and financial peace.

So I encourage you to join The Wealth Advisory today and discover a community ready to support you every step of the way as you rewrite your financial story, too.

To your wealth,


Jason Williams

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After graduating Cum Laude in finance and economics, Jason designed and analyzed complex projects for the U.S. Army. He made the jump to the private sector as an investment banking analyst at Morgan Stanley, where he eventually led his own team responsible for billions of dollars in daily trading. Jason left Wall Street to found his own investment office and now shares the strategies he used and the network he built with you. Jason is the founder of Main Street Ventures, a pre-IPO investment newsletter; the founder of Future Giants, a nano cap investing service; and authors The Wealth Advisory income stock newsletter. He is also the managing editor of Wealth Daily. To learn more about Jason, click here.

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