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$200 In My Mom’s Brokerage → $1mm Portfolio

Posted September 07, 2026

Davis Wilson

By Davis Wilson

$200 In My Mom’s Brokerage → $1mm Portfolio

When I was in grade school, my stepdad used to call me almost every afternoon during summer break.

The conversations were always the same.

"Davis, turn on CNBC."

I'd grab the remote, flip through the channels, and find the business news.

Across the bottom of the screen, stock prices scrolled by with little arrows next to them.

"What color are the arrows?" he'd ask.

"Red."

I paused for a second before asking, "Is that good or bad?"

"Bad."

Click.

That was it.

No explanation.

No lesson.

Just a one-word answer before he hung up.

This became our routine most summers.

Some days the arrows were green. Some days they were red.

I didn't understand why those colors mattered or what the ticker symbols represented.

I had never bought a stock in my life.

All I knew was that when the arrows were red, my stepdad wasn't in a particularly good mood.

Looking back, those calls made perfect sense.

This was all happening in the late 90s to early 2000s.

He was heavily invested in stocks like Lucent Technologies and Global Crossing – companies that became symbols of the dot-com bust.

Like millions of investors, he watched years of gains evaporate as the bubble burst.

At the time, I couldn't appreciate what he was going through.

I was just a kid answering the phone.

Ironically, those simple phone calls sparked a fascination that would completely change the direction of my life.

Shortly afterward I started investing myself.

I wasn't old enough to open a brokerage account, so I convinced my mom to use hers.

I funded the account the only way a teenager could – with birthday money, Christmas money, and eventually the paychecks from my first job making sandwiches at Subway.

Somehow, I actually made money trading stocks that I was familiar with – Nike, Microsoft, and the first stock I ever bought, Berkshire Hathaway.

It wasn't much – maybe a few hundred dollars.

But when you're a teenager, making $200 without leaving your bedroom feels like hitting the lottery.

Of course, I lost money too.

And that's probably the more important part of this story.

I got to experience the excitement of watching a stock I owned shoot higher, but I also experienced the gut punch of watching one collapse.

I learned what it felt like to get greedy.

I learned what it felt like to panic.

I learned how quickly a stock can move in either direction and how easily you can convince yourself that a bad investment will eventually come back.

Most importantly, I started learning these lessons when the stakes were incredibly small.

Losing $100 when you're 13 feels terrible.

Losing $100,000 when you're 40 because you never learned those lessons is a much bigger problem.

And somewhere along the way, my fascination with getting rich quickly turned into a fascination with figuring out how the stock market actually works.

I started reading more.

I started paying attention to earnings.

I started trying to understand why some companies became enormously valuable while others disappeared.

Eventually, that curiosity turned into a career.

I've now spent the majority of my adult life studying companies and investing.

I've worked in equity research, valuation, venture capital, and today I make my living writing about the stock market.

And when I look back at where all of this started, I go back to the phone ringing on those summer afternoons.

CNBC playing on the television.

And my stepdad asking me what color the arrows were.

Those calls gave me something incredibly valuable at a very young age:

A head start.

I think this is something more parents and grandparents should be doing today.

I regularly talk to people of all age groups who have no idea how to invest.

Some have spent 30 or 40 years earning a good living without ever really understanding what happens to a dollar after they save it.

Meanwhile, someone who starts investing at 13 has decades for both their money and their knowledge to compound.

You don't need to turn your kid into the next Warren Buffett.

You just need to get them started.

And today, it's dramatically easier than it was when I was growing up.

There are brokerage accounts and investing apps built specifically for families and teenagers.

Parents can oversee the account, control what their children can do, and use real money to teach them how investing actually works.

  • Give them $100.
  • Let them pick a company they know.
  • Let them watch it move.
  • Talk about why the stock went up or down.
  • Show them an earnings report.
  • Explain what owning a stock actually means.
  • Let them make a mistake while the mistake costs $20 instead of $20,000.

This is what my stepdad accidentally did for me all those years ago.

Those short phone calls ultimately gave me a massive financial head start over many of my peers.

They introduced me to investing early enough that I had years to make mistakes, learn from them, and understand the incredible power of compounding.

I have no idea whether he realized what he was starting.

He was probably just worried about his tanking Lucent shares.

But I'm thankful he called.

If you’re hanging around your children, grandchildren, nieces, nephews, or any other young people you care about this Labor Day, introduce them to investing.

Turn on the news.

Show them your brokerage account.

Send them this newsletter.

Buy a stock together.

And when they ask what the red arrows mean, tell them.

You never know where that question might lead.

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