The Summer My Family Ditched Monopoly and Went Full Wall Street
One summer, when the Texas sun was blazing, my parents did something... unexpected. They flipped our summer upside down with a stock trading challenge that made Monopoly look like preschool.
I wasn't sure if they were brave, crazy, or just hoping to make dinnertime conversations a little more exciting. Maybe all three. But I do know this — what started as a family challenge quickly became one of the most memorable, thrilling, and yes, financially educational summers of our lives.
The rules were simple: We each got our own paper trading account with $100,000. Real stocks, but fake money. The prize? A cool $1,000 to invest however the winner saw fit. And let me tell you, when you're 16 and see four digits hanging in the air like that, it's practically a million bucks.
And just like that — we were hooked.
Welcome to the Trading Floor... AKA Our Kitchen Table
So, why did my parents do this?
Well, it was less about raising the next Warren Buffett and more about encouraging us to think, to analyze, and maybe, just maybe, to fall in love with the stock market. It was their way of teaching us an important life lesson — if you don't let your money work for you, you'll end up working for money your whole life.
And what better way to learn that than to throw your kids into the middle of a trading floor, aka our kitchen?
Let me set the scene: I was 16, teetering between teenage recklessness and blossoming journalist. Andrew, my little brother, was 10 — young but sharp enough to be dangerous. My mom? She wasn't playing around either. She stuck with value investing like it was an old friend, staying true to it through market highs and lows. And then there was Dad, who took the challenge as an opportunity to go after some high-risk moonshots, the exact kind of thing he generally avoided in his real-life portfolio.
Me? I wanted action. I wanted returns. Big, juicy, fast returns. You know the type that makes your heart race and your hands a little shaky? That's where the thrill is! Jim Cramer and I? Besties. The "buy, buy, buy" and "sell, sell, sell" practically echoed in my head as I ran on the treadmill, plotting my next move like I was some Wall Street prodigy in the making.
Andrew? Let's just say he wasn't running on any treadmills. Instead, he was hitting the books and diving into agriculture tech.
Yep, you read that right.
While I was frantically trying to learn chart patterns and shipping metrics, my 10-year-old brother was doing a deep dive into Raven Industries — a company I didn't even know existed until he explained it to me. Something about precision agriculture and feeding the world?
I'll be honest: I was too busy trying to daytrade to really listen.
Move Over Monopoly, We're All About Stocks Now
It's funny how something as abstract as the stock market can turn into daily conversation. Before long, it seemed like every breakfast and dinner became a family debrief.
"Any big moves today?" Dad would ask casually, as if he wasn't waiting for me to declare victory over my latest micro-cap stock.
"Oh, you know," I'd shrug, trying to sound aloof. "Just made a quick 3% on that energy stock." Inside, though? I was buzzing. Every trade felt like a personal victory, even if some of them...well...weren't.
Meanwhile, Andrew was calm, focused. He wasn't chasing returns like I was. No, he was all about playing the long game. He'd sit at the table, quietly researching the tech behind Raven Industries, while I sat there wondering how many candlesticks a chart needed to complete a cup-and-handle pattern. His patience? Annoying. But also... impressive.
And Dad? He watched his moonshots fail to launch with an amused attitude about the whole thing. They say you miss 100% of the shots you don’t take… but I think that summer, Dad missed 100% of the shots he did take.
Of course, Mom just played the whole thing cool as a cucumber. She wasn't moved by the daily fluctuations, the panic, the excitement. "I'm in it for the long haul," she'd remind us, smiling to herself as if she already knew how this whole thing would end.
Spoiler: She did.
The Rollercoaster and the Steady Climb
My first move? Small, international energy stocks. They were hot, unpredictable, and volatile — the perfect storm for my burgeoning trading addiction. I'd make a trade in the morning and spend the rest of the day checking my account. Did I nail it? Did I lose it all?
And oh, the excitement when a trade went my way! For a few glorious hours, I was untouchable. Then, of course, there were the other trades — the ones I'd rather forget. Let's just say that not every bet paid off, but the adrenaline? That was always there.
Andrew? He sat quietly, watching his shares of Raven Industries float along. While I was riding the rollercoaster, he was cruising in a reliable old pickup truck. But then, Andrew's patience started paying off. His ag-tech stock was slowly creeping up, day after day, while my quick gains often fizzled out just as fast as they appeared.
And the Winner Is...
In the end, it wasn't even close. Mom won. No flashy trades, no wild risks — just good old-fashioned value investing. She outperformed all of us, grinning like she'd known it all along.
But you know what? It didn't feel like a loss. Not really. Because that summer? That competition? It was so much more than the numbers on a paper trading account.
We all learned something.
Andrew learned the power of patience. I learned the limits of chasing returns. And we both learned that the stock market is not just about money — it's about growth, resilience, and understanding how the pieces of the financial world fit together. Anyone willing to learn can take knowledge and turn it into something real.
Years later, we're all still in the game. I made a career out of it — analyzing stocks, writing about personal finance, and yes, still keeping one eye on chart patterns as I make my moves. Andrew? He's still a long-term guy, researching companies and thinking about the bigger picture.
And my parents? They're probably proudest of all. Not because Mom won that summer, but because they managed to do something that stuck. They didn't just teach us to invest — they taught us to love it.
Now, as an adult, I've noticed something else: People are often blown away by how early my family started teaching us about investing. Friends and colleagues will tell me, "I wish my family had done that when I was younger." It's true — those early lessons didn't just give us a head start, they gave us confidence and comfort with something that seems intimidating to so many.
Now, as I sit here and think about it, I can't wait for the day when I can throw my own kids into the fire. Let them compete, learn, and discover the thrill of the market.
They're still only two, so maybe we'll wait a few years. But one day? Oh, it's happening.
How to Bring the Thrill of the Stock Market to Your Family
If you're thinking about how to make investing fun for your family, take a page out of my parents' playbook. Start a competition. Make it a game. Let your kids feel the thrill, the wins, the losses, and everything in between.
Because it's not just about the money — it's about the lessons, the conversations, and the memories that stick with you long after the competition ends.
Want to start your own family investing competition? Here's how to get it going:
1) Set the Rules:Decide how long the competition will run and what the prize will be. It doesn't have to be $1,000 — maybe it's something smaller like $100 or a special family treat. Keep it fun and lighthearted!
2) Choose Your Platform:Use a free paper trading platform, like those offered by brokerage firms or financial apps. This keeps the stakes low while still letting everyone experience real-time market changes.
3) Make It a Learning Experience:Provide resources for everyone involved. Whether it's articles, podcasts, or even YouTube videos, give each participant access to the information they need to succeed. Encourage questions and discussions.
4) Encourage Different Strategies:Let everyone find their own investing style. Whether it's day trading, long-term investing, or something in between, the goal is to experiment and learn.
5) Track Progress Together:Make it a family affair by checking in regularly. Share wins, losses, and thoughts. This keeps the competition lively and opens the door to valuable conversations about money and investing.
6) Celebrate the Journey, Not Just the Results: At the end of the competition, celebrate everyone's efforts — regardless of who comes out on top. Discuss the lessons learned, the surprises, and the strategies that worked (or didn't).
Turning investing into a fun competition can be the perfect way to ignite financial curiosity, build lifelong habits, and maybe even create some unforgettable family memories along the way. It could even be the start of something big — it was for me.