The Biggest Mistake of My Career

Jason Williams

Posted February 15, 2024

Dear Friends on the Financial Journey,

My copy editor, the person who usually makes sure I don’t look silly by misspelling simple words or misusing a semicolon when a comma would do the trick, is on a well-deserved vacation.

So in order to cut down on the potential spelling errors, formatting mistakes, and grammatical faux pas, I’ve got a somewhat shorter missive for you today.

But what it lacks in wordiness I’m convinced it makes up for in gravity.

Because it’s a story about the biggest mistake I ever made in my career as a professional investor…

A Walk Down Memory Misstep Lane

And the thing is, while I’m not up on the rooftops shouting about it, I’m not immune to errors.

In fact, I’ve made quite a few throughout the course of my handful of decades on this planet.

And three relatively recent cases spring pretty quickly to mind…

Picture this: It’s 2012, and I’m sitting at my desk confirming some trades with PIMCO Asset Management over the Bloomberg Terminal.

That’s when I overhear a couple of my fellow analysts debating this new digital asset that one had been trading and the other had been accumulating.

It was all centered on this new concept called cryptocurrency and the asset in question was none other than Bitcoin.

Back then, it cost a few bucks a coin (that’s not a typo — it closed 2011 at $4.70).

And it would have made me a tidy profit had I bought and held, but I shrugged it off and the rest is history…

BTC 2011 to Peak

But that wasn’t the first time I missed the boat on a great investment I had the early inside scoop on…

There was also that day in 2009…

I’m sitting alone in my studio apartment microwaving a Stouffer’s lasagna for dinner (depressing, I know).

But I was also unwrapping a DVD from Netflix, thinking about what a cool way it was to watch movies…

And not even giving a second thought to the company behind it or the stock that represented it.

NFLX 2009 to Peak

But again, that wasn’t the first time I made an investing mistake…

Let’s not forget that prime deal I snagged on Amazon Prime when I got that discounted student membership during my college days in the very early 2000s.

AMZN Prime Launch to Peak

Unfortunately, I was more focused on the discounts and the free shipping than the stock potential staring me right in the face.

The Giant Shadow of a Tiny Thought

But here’s the twist, my friends.

Those “oops” moments, while they might seem pretty big…

They’re just pebbles on a path.

They’re nothing compared with the boulder I was about to trip over.

But this wasn’t about missing out on a stock; it was about missing out on a mindset.

Ego Has Entered the Chat

Coming from the high-speed, high-stakes world of Wall Street, I had a bit of a chip on my shoulder.

I thought I had the golden playbook.

And if the market was a game, I believed I was always one move ahead.

But boy, was I wrong.

This wasn’t a game I could master and move on with…

It was a never-ending classroom, and I was skipping lessons.

The Lightbulb Moment

The real game-changer wasn’t a hot stock tip; it was a cold splash of humility.

lightbulb moment

It dawned on me that the market is the world’s most dynamic classroom, and I was playing hooky.

I was so caught up in what I thought I knew, I missed out on what I could learn from others, even those just starting out or coming from completely different walks of life.

Turning Pages and Profits

This realization didn’t just open my eyes, however; it also opened doors…

Doors to new strategies, new perspectives, and, yes, new profits.

opening doors

I started listening more than I spoke, learning more than I lectured. And guess what?

The market rewarded me for it. And I didn’t pass on stocks like Nvidia or Super Micro Computer because someone lese told me about them…

And my subscribers benefitted too as I recommended investments in the two companies at $39 and $32, respectively:

NVDA from TWA Rec

SMCI from TWA Rec

As you can see, my investments started doing MUCH better, not because I was smarter, but because I was wiser.

Join the Club of Curious Minds

So here’s my call to you: Let’s be students of the market together.

Whether you’re a Wall Street veteran like me or a Main Street newcomer, I’ve made sure there’s a seat for you at this table

A table where we’re building a community in which curiosity leads and egos take the back seat.

It’s not just about beating the market; it’s about beating our yesterday selves, growing our knowledge, and, of course, growing our portfolios along the way.

Let’s Make Those Mistakes Count

Every misstep is a lesson, and every lesson is a step toward success.

As a young man with a big ego, I learned that the hard way, but you don’t have to.

Join me, and together let’s turn those “what ifs” into “what’s next.”

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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