This is the story of a tremendous win or a colossal mistake, depending on your perspective.

It begins in the mid-2000s. Cell phones were exciting and surf cams were becoming a thing.

I was still young, but I had been through a few heavy years.

After finishing a master’s in HR and Organizational Development, I landed a job I thought would launch my career. Then a health issue sidelined me and I missed a lot of work.

When I returned, I wasn’t fully myself. Eventually, I was let go.

After a few discouraging months, Prudential California Realty took a chance on me. I was hired as an administrative assistant at a branch near my apartment. It wasn’t a dream job, but I was grateful and unexpectedly intrigued by real estate.

That role eventually evolved into copywriting with the company’s corporate marketing department. The firm is now Berkshire Hathaway HomeServices California Properties, and I still work with many of the same people today. But that’s another story.

At the time, part of my job included covering the front desk for Annette, the receptionist, when she stepped out for a smoke.

I had just quit because of my health issue. I was irritable. I had gained weight and I was constantly craving nicotine.

Watching Annette head outside for a cigarette while I sat there chewing nicotine gum was truly painful.

To put it simply, I was jealous.

Meanwhile, she seemed completely unbothered by life and kept encouraging me to invest in the stock market.

“If you’re sitting here anyway,” she’d say, “you might as well learn how money works.”

Annette, if you’re somehow reading this, thank you.

I opened a brokerage account and signed up for a trial of The Motley Fool. Today I use platforms like Schwab, Interactive Brokers, and others (linked below if you’re curious).

One of The Motley Fool’s top picks at the time was Netflix.

I could never make it to Blockbuster to avoid their late fee so I was already a customer.

Having DVDs delivered to my tiny apartment felt revolutionary, and it was always a nice surprise to see the red envelope in the mailbox.

So I scraped $190 together and bought 10 shares of NFLX at $19.

It was a huge move for me. Not because $190 is small today, but at the time it felt especially significant.

I clearly remember the sense of anxiety and excitement when I was sitting at the front desk at Prudential and clicking the “Buy” button.

Incidentally, buying shares of companies you personally use and understand is an idea popularized by Peter Lynch in One Up On Wall Street.

I didn’t have a clue about that when I bought the stock, but the Motley Fool research seemed well-reasoned and I liked Netflix.

Here’s a link to the Peter Lynch book and a few others:

Anyway, back to the story…which is, of course, an “exciting” tale of research and waiting.

Trades cost $7 back then (at Scottrade). It wasn’t (mostly free) like it is today. I didn’t fully understand exit strategies or position sizing. I just knew I didn’t want to pay commissions unless it was absolutely necessary.

The stock hit $44 and I couldn’t believe it. I was such a genius!

I had more than doubled my money in a short period of time, so I sold. I was afraid the stock would fall and my gains would disappear.

What I didn’t understand is that volatility can feel dangerous in the short term, but it is often the price of admission for extraordinary long-term returns.

If I had just had the courage to hold those 10 shares, they would be worth a staggering amount today.

That’s the difference between being right and being patient.

It’s been 20 years, and I still think about that trade.

Not because I regret the lesson.

But because I now understand what I was missing: conviction.

This story aligns with others, like XPO Logistics, that can either be framed as incredible wins or painful missteps, depending on your time horizon.

I’m not here to pretend I’ve never made mistakes.

I’m here to show what the mistakes teach. The market can be humbling and I have often thought about what could have been.

The idea that $190 can turn into $444 remains intriguing. Losing out on $190K? Really sad, however, it’s kept me motivated to think that $190 could turn into nearly $108,000.

Anyone who has spent time in the markets understands the emotional tension:

It can feel personal.

It isn’t.

The market doesn’t reward comfort.
It rewards conviction and time.

I had one.

I lacked the other.

Here are platforms I’ve used over the years in case this story resonates:

• Charles Schwab - My go-to for comprehensive research and the powerful thinkorswim trading platform. Great for a "do-it-all" primary account.

• Wealthfront - Perfect for automated, hands-off investing. I love their "Path" tool for long-term planning and their high-yield cash account.

• Interactive Brokers - Great for active traders. They offer access to nearly every global market you can think of and stop-limit orders outside of regular hours!

• Robinhood - The best mobile experience for beginners. They’ve also added a great 3% match for Gold members on IRAs, which is hard to beat for retirement savings.

Disclaimer: This post is for informational purposes only and does not constitute financial advice. Some links above are referral links; I may receive a bonus if you sign up, at no extra cost to you. Always do your own research.

P.S. For those wondering about the $108,000 math: Between 2004 and 2025, Netflix had three stock splits (2-for-1, 7-for-1, and 10-for-1). Those original 10 shares would have multiplied into 1,400 shares today. It's a staggering reminder of the power of compounding.