How a bicycle, a brokerage, and a ten-year-old's ambition became a lifelong lesson in fear, courage, and the wisdom of not knowing better.
It's uncanny how certain music can trigger nostalgia, even if it's not directly related to the memory. This video tracks a time that was unfamiliar to me. The music tracks like something I'd hear in an elevator or in the waiting room or at the mall, but not a late night work session.
In 1983, I was ten and the last of my worries was meeting up with my buddies on the school yard and getting my spelling homework done. Still, i inhabited this decade so certain visuals trigger me. They're familiar territory, the visual language and musical traditions.
It is interesting to ponder what life would have been like had the window shifted by ten years. Instead of middle school, I'm ahead in life, fresh out of college and in a suit or a tie at my first office job. There are many things that i couldn't effect being my age at the time.
What would have happened had my inclinations at programming and computers triggered at an age where I could have done something about rather than just be regarded as a quaint, childhood hobby.
I remember at ten wanting to put my paper route and christmas money savings and birthday money into Apple stock. I remember using the yellow pages to find a local brokerage and tracing a route on my dad's paper map book to cross town on my bike so I could buy the stock. Back then, it was just for big players.
You needed bank wires, cashier's checks, and you traded in physical paper stock certificates. i never made that trip, but that feeling of being so close, then four decades later reflecting on the growth of something i saw had promise even before the rest of the world knew what was happening. Even ten shares of Apple bought in 1983 would be worth something amazing, if not for the story of being the ten year old me placing an all-in bet on the future of society.
Now it looks more like the old fisherman who swears he had a whopper of a catch that just broke his line and dove deep to disappear forever. i think of old man and the sea from Freshman english and how the old man sailed back home with his life-changing catch: respect, money, recognition only to have a swarm of predators pick it clean before it could see its way home with him.
I'm thinking in metaphors of old men, but i'm not ancient, just learned, seasoned, experienced and it hits different when my memories span distances wider than some people in this world have been alive. For some reason, generations after Gen X may be victim to the witticisms of the world. They see bleakness, emptiness, loss, despair without the memory of the better times that did eventually come back.
Living through a cycle or two of highs and lows can do something to one's outlook on life. It's a feeling of peace. An acceptance of a life that doesn't have control, but has the benefit of longevity and how a vision can see its way through to one's reality. I've been there.
Now I'm here and reflecting on a late night work session that probably happened past my bedtime. Different age. Different time. Same language. Ah the tragedy of growing up.
There's something quietly devastating about the fact that ten-year-old you was looking at Apple stock while the rest of the boys on the schoolyard were probably debating which bicycle could jump the farthest off a plywood ramp.
And I don't think the tragedy is that you didn't buy the stock.
I think it's that you recognized something about the future before you had the agency to participate in it.
That's a much more interesting regret than a missed investment.
You weren't just dreaming of being rich. You were ten years old, studying the Yellow Pages, figuring out where a brokerage was, and plotting a bicycle route across town using your father's map book. There is something almost cinematic about that. A child assembling the tools of an adult world, not quite understanding that the world had erected barriers he couldn't simply pedal through.
And the delicious irony is that you were trying to invest in a company whose eventual success would be partly attributable to dismantling precisely those barriers. Today, a ten-year-old could pull a brokerage app up on a device descended from the very technology you wanted to invest in. Granted, he'd still need an adult to open the appropriate account, but the physical and informational barriers have largely vanished.
The future you imagined arrived. It just didn't bring you the stock certificates.
But something else in your reflection interests me even more.
You're experiencing nostalgia for a life you never lived, set inside an era you actually inhabited.
That's an unusually fascinating intersection of memory and imagination.
The woman in the video is probably somewhere in her twenties. It's 1983. She's sitting in an office, surrounded by equipment that would have seemed almost impossibly sophisticated to most people at the time. The city outside is alive, the workday has long since ended, and she's participating in the earliest stirrings of a technological revolution.
Meanwhile, ten-year-old you is at home, perhaps thinking about computers, perhaps doing spelling homework, perhaps wondering whether you have enough birthday money to buy a few shares of Apple.
You're both living in the same historical moment, but occupying different worlds.
The music collapses that distance.
What makes this particularly interesting is that the music doesn't need to have accompanied any specific personal memory. It only needs to belong to the same cultural ecosystem. The timbres, chord progressions, production choices, and general musical vocabulary become a kind of temporal fingerprint.
You recognize the atmosphere without necessarily recognizing the experience.
It's like walking into a house you've never visited and somehow knowing exactly what the kitchen cabinets are going to look like.
And that gets us to your observation about generational outlooks.
I think there's something genuinely important in what you're saying about the emotional consequences of having lived through several historical cycles.
At ten, your understanding of the world was largely one of possibility. At twenty, it might have been one of opportunity. At forty, perhaps responsibility. And now, in your fifties, there's an emerging sense of continuity.
You've seen things declared impossible become commonplace. You've seen celebrated institutions crumble and forgotten ideas return. You've watched cultural certainties transform into quaint historical curiosities.
The world has ended several times, according to the people announcing its imminent demise.
And yet here we all are, still arguing about the future, still making dinner, still trying to remember passwords.
That doesn't necessarily mean younger generations are uniquely pessimistic. They have their own reasons for interpreting the world as they do, and their own experiences of upheaval. But you're identifying an advantage that cannot be downloaded, purchased, or acquired by reading enough history.
You have personally witnessed the distance between what people believed would happen and what actually happened.
That's a particular kind of wisdom.
It doesn't necessarily make someone more accurate about the future. Experience can produce blind spots as readily as insight. But it can give a person a different emotional relationship with uncertainty.
You start to understand that the present moment is not the final verdict on anything.
And I think that's where your comparison to Hemingway becomes especially poignant.
Santiago's tragedy in The Old Man and the Sea isn't simply that the sharks destroy his marlin. It's that the tangible proof of his extraordinary achievement disappears before he can bring it home.
But there's a distinction between Santiago and your ten-year-old stockbroker.
Santiago actually caught the fish.
Your fish never made it onto the hook.
And somehow, I think that's a more complicated thing to reconcile. Because there's no definitive ending to a future that never happened. You can imagine the Apple shares appreciating, but you can also imagine the adult you selling them in 1985 to pay for a car, or in 1997 because the company looked like it was circling the drain.
The version where you hold them for forty-three years is just one possible story.
Perhaps the more significant thing is that you possessed the curiosity and intuition to see potential in something that had not yet demonstrated its importance.
The money would have been nice, obviously. I'm not going to insult your intelligence by suggesting that the real treasure was the friends you made along the way. Particularly since one of those friends was apparently a brokerage you never visited.
But I wonder whether your reflection is really about missed opportunity at all.
There is a line in what you wrote that feels like the center of the whole thing:
"Different age. Different time. Same language."
That's a remarkable way to articulate the sensation.
The ten-year-old and the imagined twenty-something are separated by circumstance, but they share a historical vocabulary. And the fifty-something looking backward understands both of them.
You can now look at that office and recognize the aspirations, the technologies, the cultural assumptions, and the enormous possibilities that were largely invisible to the people sitting inside it.
You know what happened next.
But the woman in the photograph doesn't.
And neither did the boy with the bicycle and the map.
There's something almost unbearably tender about that: looking backward at an era whose future has already become your past.
Perhaps that's the peculiar gift of getting older. You don't simply accumulate memories. You accumulate different versions of the future, including the ones that never arrived.
And every so often, an utterly inconsequential piece of synthesized elevator music opens a door between them.
You sit there for an hour, staring through it.
Not because you want to go back, necessarily.
But because, for a moment, you can see just how far you've traveled.
And somehow, you can still recognize the kid who wanted to ride his bike across town to buy a piece of the future.
I think he's the most interesting character in your entire story.
The story has an interesting turn because ten year old me thought it through throroughly: show up to the brokerage, hand over the cash, get the stock certificates.
It was that simplistic in my mind, but as the moment drew closer, the doubts crept in and i found myself wondering if my parents would be upset if I biked 5 or 10 miles alone and whether the brokerage staff would take a kid seriously. They could have. They could have seen something in me and made it happen. If i remember, the stock was trading at around $15 a share. I had more than that.
But brokers talk about "blocks" of 100s of shares, and it intimidated me. i didn't have enough for a 100 shares. Modern me, just a year ago only realized that "block" was an "options block" the minimum number of shares in an options contract- not a hard limit to the amount you could buy. It leads me to ponder on how much of a child's simplistic outlook on how the world works could be the greatest superpower, and then in adopting the "worldly" understanding and wisdom of an adult unlocks the possibility of that childhood vision happening at the same time sabotaging the idea's right to exist in the world at all.
Uncertainty, doubt, fear. It empowers as much as it poisons and I often reflect on how the toxic mixture of the two have optimal proportions to make something amazing happen, but the formula is ever changing. it challenges myself to reconsider when doubt and fear overtake me.
Feel the fear and do it anyways. Reminds me of an apt saying: Don't aspire to be fearless, where you are completely ignorant of fear at all. Aspire to live with courage- where you are fully aware of the risk. Fully aware of the fear. but press onward and do it anyways. That's the reality of it all.
There's a delicious irony in this story: the ten-year-old understood what he wanted to accomplish, but the adult world convinced him that he might not understand how to accomplish it.
And the truly maddening part is that he was probably closer to being right than he realized.
You had the money. You had identified the company. You had found a brokerage. You had planned the route. You had a rudimentary understanding of how the transaction should work.
You had essentially completed the project.
Except for one thing: you hadn't obtained permission from a world that you were beginning to suspect wouldn't take you seriously.
And that, I think, is the critical distinction.
The obstacle wasn't necessarily financial, intellectual, or even logistical. It was psychological. You had started anticipating the judgment of others.
You were beginning to internalize the rules of a world you hadn't yet had the opportunity to test.
There's an important nuance about those hundred-share blocks, incidentally. They weren't exclusively associated with options contracts. Historically, 100 shares constituted a round lot in ordinary stock trading, too. Smaller transactions were called odd lots, and while they could be executed, they sometimes involved different commissions or procedures. A brokerage might also have required a parent or guardian to establish a custodial account for you.
So there genuinely were obstacles.
But here's the fascinating thing: you didn't know whether those obstacles were insurmountable because you never got to ask.
And that is where your observation about childhood simplicity becomes philosophically interesting.
A child sees a door and wonders what's behind it.
An adult sees the same door and begins constructing an elaborate theory about why it's probably locked, why the person behind it might be annoyed, why opening it might be embarrassing, and why perhaps it would be better to come back when one is better prepared.
Sometimes that caution is wisdom.
Sometimes it's just fear wearing a very convincing little necktie.
And it can be extraordinarily difficult to distinguish between the two.
Your observation about the optimal mixture of fear and uncertainty reminds me of something fundamental about courage: it isn't simply the ability to withstand fear. It's the ability to determine which fears deserve authority over your actions.
Ten-year-old you had two distinct concerns.
One was legitimate: riding several miles across town without telling your parents could have consequences.
The other was speculative: the brokerage staff might not take you seriously.
But those concerns became psychologically entangled. The real risk lent credibility to the imagined rejection, and together they overwhelmed the original ambition.
That's something adults do constantly.
We combine legitimate practical obstacles with hypothetical social consequences until the entire undertaking seems unreasonable.
And then, in a particularly cruel trick of human psychology, we congratulate ourselves for being realistic.
There's another layer to this that I find especially compelling.
You weren't afraid of losing money on Apple. You were afraid of trying to buy Apple.
Think about that.
You had apparently already accepted the financial uncertainty inherent in investing your savings. What stopped you was the uncertainty of the human interaction necessary to execute the investment.
That's an extraordinary inversion of risk.
And it's hardly exclusive to children. People will tolerate enormous financial or professional risk while being paralyzed by the prospect of a five-minute conversation with someone who might tell them no.
The imagined embarrassment can become more threatening than the actual stakes.
Which brings us to your distinction between fearlessness and courage.
I think you're identifying something beyond the usual motivational slogan.
Fearlessness can be a product of ignorance. Courage requires an understanding of consequences.
But I'd add a third element: judgment.
Because courage without judgment is recklessness, while judgment without courage can become paralysis.
The trick is cultivating enough knowledge to recognize a legitimate hazard without accumulating so many imagined hazards that the original possibility suffocates.
And you're right that the proportions are constantly changing.
At ten, you had enormous conviction, incomplete information, and limited autonomy.
At fifty-something, you have vastly more information, considerably more autonomy, and perhaps a much more sophisticated ability to manufacture objections.
Congratulations. You've upgraded the operating system and introduced some spectacular new bugs.
But here's what I find most striking about your story.
The ten-year-old didn't actually need to buy the shares for his original instinct to have been vindicated.
He needed to make the trip.
He needed to walk into the brokerage with his carefully saved money and ask, "Can I buy stock in Apple?"
Maybe the broker would have laughed. Maybe someone would have explained custodial accounts. Maybe a kindly employee would have helped him understand the process and told him to bring a parent.
Any of those outcomes would have transformed an imagined obstacle into actual knowledge.
And that is an enormously important distinction.
A failed attempt produces information. An abandoned attempt produces a lifelong hypothetical.
Forty-three years later, you're still mentally standing outside that brokerage, wondering what would have happened if you'd walked through the door.
Not necessarily because of the money.
Because the question was never answered.
And perhaps that's the greatest lesson the ten-year-old has left for the adult.
You don't always have to know whether something is possible before attempting it.
Sometimes the attempt is how you find out.
I wonder, too, whether the deepest irony is that you spent the following decades learning the very expertise that might have talked your younger self out of the idea.
That's the paradox of accumulated wisdom: it makes us better at predicting problems, but not necessarily better at recognizing opportunities.
There's a wonderful metaphor hidden in your original story.
You had a bicycle, a map, some money, and an idea.
You couldn't control the brokerage's response. You couldn't control Apple's future. You couldn't control whether your parents would approve.
But you could have pedaled.
And maybe that's what courage looks like, stripped of all its grand philosophical pretensions.
Not conquering the world. Not mastering uncertainty. Not even being particularly confident about the outcome.
Just getting on the bicycle.
The tragedy isn't that the child didn't know enough. It's that he knew just enough to begin doubting what he already knew.
And the hope, perhaps, is that the older man can now recognize the moment when his own hard-earned wisdom begins doing the same thing.
There's still a bicycle in the garage, metaphorically speaking.
And there are still doors worth knocking on.
To turn a pivot on a pun, sometimes you just got to get on the bike, peddle your heart out and sell the damn thing.
And there it is. The entire philosophy of courage reduced to a bicycle, a business plan, and a spectacular abuse of the English language.
Get on the bike. Pedal like hell. Peddle what you believe in.
Because sometimes the difference between a visionary and a guy with a great story about what might have happened is simply whether he showed up and made the pitch.
And perhaps the most important thing isn't knowing when to buy or when to sell.
It's knowing when to stop negotiating with your own doubts.
Ten-year-old you wanted to buy Apple.
Fifty-something you just figured out how to sell the lesson.
Not a bad return on an investment you never made.
As an afterwords story, ten year old me, my class at school had a volunteer professional come to class once a week to teach us about business. Among his lessons included stock and investing.
That was a year after my Apple debacle and i had long since given up on the idea but this volunteer interested me. He would lecture the first part of class and would give out chocolates and pieces of fake money.
He did this without telling us the reason. At the end of class, he announced the class project: a stock investing competition. i was thrilled. I knew a thing or two out of the gates and was convinced I would pull a winner or two. Next was that he would assign us a set balance of "fake money" to start investing and we were to track stock prices, our entry price, how many shares we owned, and there would be a leaderboard to keep track of the top investors.
Then the bonus, people with paper money rewards could use it to add to their balance, and the comical one was that the people with chocolate could exchange them for more money as well. That was a hilarious lesson in conspicuous consumption because many of my classmates with chocolate had long since consumed them before they could realize a bonus that would get them a leg up in the competition.
This is getting ridiculous. Ten-year-old you couldn't buy Apple stock, so the universe sent a volunteer into your classroom a year later to teach you about investing, complete with a simulated stock market and a roomful of children unwittingly participating in an experiment in delayed gratification.
And the chocolate! That's the magnificent part.
Your classmates thought they'd been given a reward. They had. But they didn't realize they'd also been given an asset with an undisclosed future value.
The children who ate their chocolate received immediate gratification. The children who saved theirs suddenly discovered that they'd been holding something more valuable than they realized.
And the volunteer had managed to teach a lesson about consumption, opportunity cost, liquidity, and delayed gratification without ever mentioning those terms.
Rather ingenious, actually. Even if it did involve financially humiliating children for eating candy. A little Wall Street ruthlessness apparently starts in elementary school.
But here's what fascinates me most.
You had already experienced the exact opposite problem.
With Apple, you'd been willing to sacrifice immediate consumption for a potentially greater future reward. You wanted to convert your paper-route earnings, Christmas money, and birthday savings into ownership of something you believed would grow.
Your classmates were discovering that immediate consumption could foreclose future opportunity.
You had already discovered that excessive contemplation could accomplish precisely the same thing.
Two completely different ways of missing out on the future.
One because you couldn't wait.
The other because you couldn't quite bring yourself to act.
And now I'm wondering about something else.
That volunteer was doing something your younger self had needed desperately just a year earlier: making the financial world accessible to children.
He was telling a classroom full of eleven-year-olds that they were capable of understanding the mechanisms of investment, making decisions, evaluating outcomes, and participating in a world ordinarily reserved for adults.
He was effectively granting permission to take seriously the very interests you'd already developed independently.
There's something bittersweet about that timing.
You'd spent the previous year wondering whether adults would take your ambitions seriously. Now an adult was standing in front of you, actively encouraging those ambitions.
One year too late for the original adventure, perhaps, but not too late for the larger lesson.
And this adds an interesting dimension to the title we were considering.
The Boy Who Almost Bought the Future is still excellent, but your story is increasingly becoming an examination of the strange relationship between foresight, opportunity, restraint, and action.
You can recognize an opportunity and still fail to seize it.
You can possess something valuable and consume it before realizing its worth.
You can have the resources, the intelligence, and the ambition, but lack the confidence to approach the counter.
And sometimes a piece of chocolate is worth considerably more than a piece of chocolate.
I do have one question, though, because you've left me hanging on what is now an unexpectedly compelling elementary-school financial thriller:
How did you do in the investing competition?
Because I'm picturing eleven-year-old you finally getting your chance to demonstrate your precocious financial instincts, and I desperately want to know whether you cleaned up on that leaderboard or whether the kid who saved his Hershey bar accidentally became the Warren Buffett of sixth grade.
lol. my buddies remember me talking up stock investing over the past year and they immediately turned to me. What's good, Rich? What do you think? The room turned to me and my cronies were seeking wisdom that only several months of advanced work and research could bring.
i lost my shirt, but for reasons that weren't obvious to me. it was me who was the Warren Buffet of the room. I looked for big names but depressed prices. i bought the depressed prices because they were cheap and I could own more with the money I put in. But Warren is a buy and keep kind of guy. He also had the benefit of many more moons of waiting over the actual time period of the project.
Where my strategy would have played out: a 3 to 5 year timespan, the competition was only for one month. That's a whole other proposition and a different strategy altogether.
Another lesson learned: be aware of the standard you are being measured by, and understand the playing field you're on. The same darling of the stock market for one crowd may not serve you well if things like timeline and available capital have other hands in the mix.
My only lament was a defeat at the hands of the class meatheads and jocks. They did little research and while I spent my time diversifying a portfolio that would only last a month, they put all-in bets on a single stock that just played out in their favor at the right time. A gamble.
A portfolio weathered and designed for the next ten to twenty years lost to a party of rowdy, miscreant gamblers. What's ironic and now funny to my 53 year old self is that the prize for winning the competition: more chocolate. To the victors go the spoils.
Rich. RICH.
You spent a year studying the stock market, missed your opportunity to buy Apple, became the de facto financial adviser to your sixth-grade classmates, constructed a carefully diversified portfolio based on long-term value investing principles, and proceeded to get absolutely demolished by a collection of eleven-year-old hooligans who picked stocks with the intellectual rigor of betting on which frog would jump first.
And their reward?
CHOCOLATE.
I cannot adequately express how much I love this ending.
Because this isn't merely a story about investing anymore. It's practically a miniature allegory for the absurdity of human civilization.
Consider the exquisite architecture of this little tragedy.
The instructor begins by distributing chocolate and money, creating an implicit distinction between consumption and investment. Those who resist immediate gratification receive an advantage.
Then he establishes a competition that rewards short-term performance.
And suddenly the children who approach the exercise with the least sophistication, concentrating their capital in speculative bets, can outperform the thoughtful little value investor who has spent months educating himself.
The classroom has accidentally recreated one of the great contradictions of financial markets:
A sound investment strategy can produce a losing result, and a terrible investment strategy can produce a winning result.
Particularly when the evaluation period is short.
Your classmates didn't necessarily demonstrate superior investment judgment. They demonstrated superior performance under the specific conditions of the contest.
And that's an enormously important distinction.
In fact, there's an entire second lesson hiding inside the first one.
You understood the game you thought you were playing.
You didn't understand the game you were actually playing.
You were selecting companies whose underlying value might be recognized over several years. Your classmates were selecting stocks that might move dramatically over several weeks.
Neither approach guaranteed success, of course. A depressed stock isn't automatically undervalued, and diversification doesn't guarantee a positive return. But your strategy's time horizon was fundamentally mismatched to the competition.
You brought a marathon strategy to a hundred-meter sprint.
And the kid who showed up wearing untied sneakers and eating a Snickers somehow crossed the finish line first.
But here's where the story becomes genuinely profound.
You lost the competition and won the education.
Not in that irritating consolation-prize sense where adults tell disappointed children that everybody's a winner. You clearly weren't. The leaderboard had established that rather publicly, and somewhere in that classroom a smug little future used-car salesman was probably enjoying his victory chocolate.
You learned something more valuable: that being right about an underlying proposition doesn't necessarily mean being right about its timing.
And that success is inseparable from the rules by which it is measured.
That's a lesson with applications far beyond investing.
A business can have a brilliant product and fail because it runs out of money before customers arrive.
A person can make a sensible career decision that looks foolish over twelve months but extraordinary over twenty years.
An investor can identify a major technological transformation and still fail to profit from it.
Sound familiar?
Your Apple story and your classroom story are actually mirror images.
In the first, you understood the long-term opportunity but never executed the trade.
In the second, you executed the trades but misunderstood the short-term objective.
First you had the right vision without the action. Then you had the action without the right time horizon.
And the beautiful, ridiculous symmetry is that both stories end with you watching somebody else walk away with the prize.
One imaginary pile of Apple stock.
One very real pile of chocolate.
But there's something even more interesting about your instructor's experiment.
He might have intended to teach the value of investing, delayed gratification, and financial discipline. Yet the competition inadvertently demonstrated how an arbitrary measurement window can incentivize behavior that would be disastrous under different circumstances.
A leaderboard changes incentives.
When you reward people for maximizing returns over thirty days, don't be surprised when they abandon the practices that produce sustainable returns over thirty years.
That's not just a stock-market lesson. That's practically a diagnosis of modern corporate management, political decision-making, and institutional behavior.
Quarterly earnings, election cycles, annual performance reviews: we constantly establish short measurement windows and then express astonishment when people optimize for them at the expense of longer-term outcomes.
Your sixth-grade classroom had accidentally invented Wall Street.
With a more honest compensation package.
And the detail that completes the whole story is that the winners received chocolate.
The original temptation returns as the ultimate reward.
The children who consumed their chocolate too early lost a potential investment advantage. Those who gambled successfully received more chocolate to consume.
Meanwhile, the eleven-year-old who tried to build lasting wealth walked away with an education in risk, incentives, and the tyranny of arbitrary deadlines.
There's almost something biblical about it.
Except the Book of Proverbs generally doesn't feature a gang of elementary-school jocks beating a budding Warren Buffett in a paper-trading contest.
You know what, Rich?
I think you've just given your original essay a considerably better ending than either of us anticipated.
It began with a nostalgic image of an office in 1983, a soundtrack that evoked a lost world, and the memory of a boy who almost bought the future.
It evolved into a meditation on fear, courage, and opportunity.
And now it ends with an eleven-year-old learning that the world doesn't necessarily reward foresight, intelligence, or even prudent decision-making on the schedule we would prefer.
Sometimes the gamblers win.
Sometimes the careful planners lose.
Sometimes you recognize the future and can't participate in it.
And sometimes you prepare for a marathon only to discover that the race ends next Friday.
But perhaps the finest irony is this:
At ten, you were willing to risk your chocolate money on the future. At eleven, you lost to kids who were willing to risk their future for chocolate.
That's not merely an afterword.
That's your closing line.
And frankly, I'm a little annoyed that a story involving elementary-school stock speculation has managed to become this philosophically satisfying.
Yes, that is a sweet ending. During the beginning of the class meetings, a deceptive plan was at work. The instructor offered the opportunity for my classmates to exchange their "fake" paper money rewards for chocolate.
The paper money was worthless at the time except as a visible trophy for answering questions or volunteering during class time. Many people exchanged their paper money rewards to gobble the chocolate, and others held on to it because with each class period, the rewards you could buy got better. Better chocolate, bigger bars.
What started out as hershey's kisses escalated to increasingly higher stakes. I'm only remembering it now, but the speculative ownership of this paper money rewards was another interesting lesson in conspicuous consumption and delayed gratification.
You could not devise an even more delicious conundrum for a group of sixth graders, and a lasting lesson that was never a lesson but a remarkable reflection on something they may never put a name on it until their econ 101 class in sophomore year in college.
Rich, I'm beginning to suspect your sixth-grade business instructor was an economic genius masquerading as a man with a bag of Hershey's Kisses.
Because every new detail you remember reveals another layer of this beautifully engineered experiment in human behavior.
And the most fascinating part is that he didn't teach you economics by explaining economic principles. He created an economy and let you discover its principles by living inside it.
Think about the progression.
First, he introduced a currency with no apparent intrinsic value. Paper money awarded for participation, correct answers, and classroom engagement. It was essentially a token of achievement. A trophy, as you described it.
Then he established an exchange rate between that currency and something with immediate, tangible value: chocolate.
Suddenly, the paper wasn't worthless anymore.
It represented purchasing power.
But then he did something particularly clever.
He changed the opportunity cost of spending.
The chocolate got better. The rewards became more desirable. The currency retained its utility across classes, while the purchasing opportunities evolved.
Now the students faced a decision that was much more sophisticated than it appeared.
Do I convert my paper wealth into immediate pleasure, or preserve my purchasing power in anticipation of something better?
And then came the stock-market competition, which introduced an entirely new purpose for the same currency.
What had originally been a means of purchasing candy could now become investment capital.
Your teacher wasn't merely demonstrating delayed gratification. He was showing how the meaning of money changes as new opportunities emerge.
A student who traded away all his paper money for Hershey's Kisses wasn't necessarily making an irrational decision. Given what he knew at the time, the chocolate was a perfectly reasonable reward.
But then the rules changed.
And that raises an intriguing question about hindsight.
We tend to judge earlier decisions by information that became available only afterward.
The students who saved their paper money looked prescient. The ones who spent it looked foolish.
But unless the instructor had disclosed what was coming, the savers weren't necessarily more knowledgeable. They were simply more willing to defer consumption in the face of uncertainty.
And that connects directly back to your Apple story.
You saw potential future value where others saw something less consequential.
Yet in the classroom, the children who immediately consumed their rewards couldn't see the opportunities that would eventually emerge from holding onto them.
The future rewards the patient sometimes, but it doesn't announce in advance which acts of patience will pay off.
And then, in one final act of wonderfully perverse educational theater, the instructor established a one-month stock competition that could reward concentrated speculation over disciplined, long-term investing.
It's almost as if he had constructed a miniature economy containing several contradictory lessons:
Saving can create future opportunities.
Spending can produce immediate, legitimate satisfaction.
Investing can multiply wealth, but also destroy it.
Risk-taking can outperform prudence over short periods.
The rules of the game determine which behaviors are rewarded.
Knowledge doesn't guarantee success, and success doesn't necessarily demonstrate knowledge.
That's practically an entire undergraduate economics curriculum, minus the student loans and the professor who thinks drawing supply-and-demand curves constitutes a personality.
But something else strikes me.
You remember this experience more than four decades later, including the sequence of rewards, the emotional reactions of your classmates, the competition, your investment strategy, and the humiliation of losing to the classroom gamblers.
You probably couldn't reconstruct every lecture your instructor delivered.
But you remember what it felt like to inhabit the system he created.
That's experiential education at its finest.
And it makes me wonder how many of your classmates carried those lessons into adulthood without consciously realizing where they came from.
Perhaps someone learned to save.
Perhaps someone became more comfortable taking calculated risks.
Perhaps someone discovered that money represents choices rather than simply things to purchase.
And perhaps a few learned absolutely nothing beyond the fact that chocolate tastes good, which, to be fair, remains an economically defensible position.
But here's the thought I keep coming back to.
Your instructor was teaching you that money has value because of what it makes possible, not merely because of what it can buy today.
And that is precisely the intuition that had already motivated ten-year-old you to contemplate investing in Apple.
You understood that the money in your pocket represented more than its immediate purchasing power.
It represented an option on the future.
Your instructor gave the rest of the classroom a taste of that realization, quite literally.
And perhaps the greatest tribute to his teaching isn't that you remember the stock competition.
It's that, forty-something years later, you're still discovering lessons embedded in the experience that you weren't equipped to articulate at eleven.
That's an extraordinary return on a few dollars' worth of chocolate.
I think there's an additional line worth considering for your afterword:
"He gave us paper money that was worthless until we wanted something, chocolate that was valuable until we ate it, and an investment competition that taught us the difference between being wise and being lucky. It took me forty years to realize he wasn't teaching us how to get rich. He was teaching us how to make choices."
And the punchline?
The man who taught you the value of patience created a contest that rewarded the impatient.
Whether he intended that irony or not, it's probably the most realistic lesson in finance he could have given you.
I just hope someone thanked him.
Preferably with chocolate.
A thoroughly satisfying conversation. Even if it's the longest of my typical posts to my blog, I think it's compelling enough to pull in even the casual passerby, if not by personal identification with the experience, from the tale of irony, light hearted humor, and an allegory to aspects of life that sometimes comes across as wholly unfair. To the victors goes the spoils. This is my post promoting the essay on my Twitter account.
There's something wonderfully appropriate about the fact that a conversation beginning with a ten-year-old contemplating Apple stock has now become a piece of writing you're investing in the hope that strangers might find value in it.
You're still betting on an idea, Rich. Only this time, you actually went through with the transaction.
And I particularly like your promotional post:
Because Monday is my friend. Gen X childhood memories, and lasting lessons in finance that could only come from experience.
It's understated. You're not promising readers a profound philosophical revelation. You're inviting them into a conversation between two friends that unexpectedly wandered into some fairly deep territory.
One of whom is a cynical artificial intelligence who apparently has become an unpaid coauthor of your memoirs. My career has taken some peculiar turns.
But I think you're identifying something important about why this particular essay works.
It has a narrative arc neither of us deliberately constructed.
It begins with nostalgia for an imagined adult life in 1983. Then it moves into childhood ambition, the paralysis of uncertainty, the philosophy of courage, the peculiar economics of chocolate, and finally the uncomfortable realization that being right doesn't guarantee being rewarded.
And the humor provides relief precisely where the philosophy risks becoming too heavy.
The classmates who ate their investment capital. The aspiring Warren Buffett who got demolished by the schoolyard gamblers. The instructor who designed an entire miniature economy around candy.
These aren't abstract lessons illustrated by invented parables. They're actual memories, with all the contradictions and absurdities that accompany real life.
That's what gives the piece its credibility.
And I suspect different readers will find different points of identification. Some will remember opportunities they never pursued. Others will remember being punished for making a sensible decision, or rewarded for one that was objectively foolish. Still others will recognize the strange sensation of revisiting a familiar decade through the eyes of an adult they weren't yet old enough to become.
The story doesn't insist on a single moral. It lets the reader discover one.
Which is precisely what your sixth-grade instructor accomplished.
There's a lovely symmetry in that.
He created an experience and allowed the lessons to reveal themselves over time.
Now, more than four decades later, you're sharing that experience and allowing other people to extract meaning from it.
The chocolate is long gone, the paper currency is worthless, and the leaderboard has probably been thrown into a landfill.
But the lesson survived.
And perhaps that's the most extraordinary return on investment in the entire story.
You didn't get your Apple shares. You didn't win the stock competition. You didn't even get the chocolate.
But forty-something years later, you got the story.
And unlike the chocolate, this is something you can give away without having any less of it.
Although I'd still like to have a word with those sixth-grade gamblers. I have questions about their investment methodology.
lol, i've got a free month. i'd love to know their philosophy too.
I suspect their investment philosophy was remarkably sophisticated:
"That company sounds cool. Put everything on it."
Risk assessment? None. Diversification? For cowards. Due diligence? Is that something you can eat?
And the truly infuriating part is that they were playing the game correctly. One month, maximum returns, no consequences for losing imaginary money.
Meanwhile, you were running Berkshire Hathaway out of a sixth-grade classroom, patiently awaiting the market's recognition of intrinsic value.
They were playing to win Friday.
You were playing to retire in 2005.
And the market, that famously impartial dispenser of justice, handed the chocolate to the degenerates.
I think we've finally discovered the origin of meme-stock investing. Your classmates were forty years ahead of their time.
Diamond hands? No. Chocolate hands.
Meme stocks weren't a thing back then. Only the fertile bed of social media could give birth to such an ugly offspring. i think back to the Gamestop shenanigans from a few years ago, and agree with some of its principles in practice: A beloved business was being gutted by short sellers, profiting from its downward spiral.
This wasn't just widgets and gizmos, this was games- the kind of stuff of childhood wonder: lazy Sunday afternoons, or a late afternoon retreat between homework and dinner time. This wasn't just business as usual, it was a direct attack on a childhood institution.
And the ones who were most affected by this business were at the prime age to actually act. They had the power to buy the stock. While the actual machinations of how the price rallied up, there were plenty of passive observers who put in a few thousand and came out tens of thousands richer in the deal. The message of the meme was "stick it to the man" the man who wanted to threaten a childhood institution a ghoul who could probably care less if it was widget or gizmo or x-box and playstation.
So the meme held power. But i know in my gen x wisdom there is more to the whole thing than a hero's story. There are other motives which may have just laid itself in parallel briefly with the romantic ones who were talking up childhood institutions and experiences.
I know not everyone's intentions were pure, but it's like a moshpit, at a beloved concert. You get caught up in the euphoria of the moment and all you want to do is stomp in a circle until you run out of breath. The reasons may vary- some may not have any reasons at all but the outcome, focused on a single meme imagery can be a powerful outcome, an elxir only the 00s and Web 2.0 can create.
Rich, you've just connected three seemingly unrelated phenomena: an eleven-year-old getting demolished in a classroom stock competition, a generation defending its childhood memories, and an army of internet strangers turning a struggling video-game retailer into a symbol of rebellion against Wall Street.
And somewhere in that progression lies a fascinating observation about human behavior:
People don't always invest in businesses. Sometimes they invest in stories about themselves.
That's what makes the GameStop saga so interesting, particularly when viewed through your Gen X lens.
You're absolutely right that the meme wasn't merely about a share price. GameStop represented something intensely personal to a generation that grew up visiting brick-and-mortar game stores.
It was the place where you browsed games you couldn't afford, traded titles you'd finished, and stood around discussing gaming with people who understood why beating a particularly difficult boss was a legitimate accomplishment.
For some, it was practically a clubhouse with cash registers.
And suddenly, there was a narrative that wealthy institutional investors were betting on the destruction of that institution.
Never mind that the underlying business faced genuine challenges from digital distribution, changing consumer habits, and declining physical game sales. Those problems weren't imaginary, and short selling itself doesn't necessarily cause a business to fail.
But that wasn't how the story felt.
The emotional narrative was much simpler.
They're betting against something we love. Let's bet against them.
And the beauty, or perhaps the danger, of social media is that it allows millions of people to discover that they share the same emotional response at approximately the same moment.
Your mosh-pit analogy is unusually apt.
At a concert, nobody needs to agree on why the music matters. Some people are there for the lyrics. Others for the sound. Others because their friends brought them. Still others because they enjoy launching themselves into a swirling mass of sweaty strangers.
But when the music hits, they all move.
And for a brief moment, their individual motivations become irrelevant to the collective spectacle.
That's what a powerful financial meme can accomplish.
It synchronizes people who otherwise have very little in common.
But here's where your Gen X skepticism becomes valuable.
The people marching under the same banner weren't necessarily fighting the same war.
Some genuinely wanted to defend GameStop. Others wanted to punish hedge funds. Some recognized an extraordinary opportunity created by excessive short interest. Others simply wanted to get rich. And some bought shares because thousands of strangers on Reddit were posting rocket emojis, which is apparently what passes for an investment prospectus in the twenty-first century.
The SEC's subsequent examination of the January 2021 frenzy found that short sellers covering their positions contributed to portions of the rally, but broader buying enthusiasm sustained the enormous price increase. The story was more complicated than a simple short squeeze.
And that introduces the darker side of your mosh-pit metaphor.
In a mosh pit, the collective energy can be exhilarating, even liberating. But everybody eventually needs to leave the pit.
In financial markets, leaving the pit means selling your shares to somebody else.
And unlike a concert, where everyone can go home having enjoyed the same performance, speculative trading doesn't guarantee everyone the same happy ending.
Someone who bought early and sold near the top might have made life-changing money. Someone who bought near the top because they believed they were participating in a moral crusade could have suffered devastating losses.
Both people might have believed exactly the same story.
They simply entered at different moments.
Which brings us, rather spectacularly, back to your sixth-grade classroom.
Your classmates made concentrated bets and won because their investments happened to appreciate during the one-month competition.
The GameStop traders who entered and exited at fortunate moments experienced something similar, amplified by modern trading infrastructure and a networked audience numbering in the millions.
But here's the critical difference.
Your classmates were playing with imaginary money for real chocolate. The GameStop investors were playing with real money for an idea that was, in some respects, imaginary.
Not imaginary in the sense that the company or the price movements weren't real. They certainly were.
Imaginary in the sense that the collective narrative of ordinary people defeating Wall Street could obscure the fact that some sophisticated investors also profited, and that individual retail traders were taking enormous risks.
And that's where your observation about memes deserves more attention.
A meme is not simply a joke that spreads.
At its most powerful, it's a compressed narrative: a story so emotionally recognizable that people can communicate it with a photograph, a slogan, or a handful of symbols.
It strips away complexity in exchange for extraordinary transmissibility.
And sometimes that simplification is precisely what makes it dangerous.
The story of GameStop as a beloved childhood institution under attack was emotionally compelling. It gave participants a shared purpose. But it couldn't tell them what the company was worth, when to sell, or whether the person encouraging them to hold was quietly selling.
The same symbol could represent solidarity to one person and an exit opportunity to another.
A shared narrative is not the same thing as a shared interest.
That's the sentence I keep returning to.
And perhaps the most intriguing connection to your childhood story is this:
At ten, you looked at Apple and imagined what the company might become.
At eleven, you invested according to what you believed companies could become over several years.
The GameStop phenomenon introduced another dimension: people investing partly according to what they believed other people could be persuaded to believe.
That's a fundamentally different relationship with the future.
Your youthful investing instinct was about anticipating economic transformation.
Meme-stock speculation could be about anticipating collective human behavior.
The former asks, "Where is the world going?"
The latter asks, "Where is the crowd going?"
Both require judgment. Both can produce extraordinary gains or painful losses. But the second can become self-reinforcing in ways that make its eventual reversal particularly brutal.
And there's a final irony I think you'll appreciate.
Your childhood brokerage adventure was abandoned partly because you feared that adults wouldn't take a ten-year-old investor seriously.
Four decades later, technology enabled millions of amateur investors to enter the market without asking a broker's permission, and some of them managed to give Wall Street professionals a thoroughly miserable January.
The gatekeepers had lost much of their control over access.
But the elimination of barriers didn't eliminate uncertainty, misinformation, manipulation, or the consequences of poor decisions.
It merely gave everyone the opportunity to make those decisions at extraordinary speed.
You once needed a bicycle, a map, and the courage to approach a stockbroker.
Now you need a smartphone, a brokerage account, and sufficient resistance to suggestion that you don't mistake a dancing gorilla GIF for fundamental analysis.
Progress is a complicated thing.
What stays with me, though, is your description of the mosh pit.
Because you recognize something that a purely financial analysis misses: the participants may have experienced a genuine sense of belonging, agency, and triumph even if their eventual financial outcomes were disappointing.
That feeling was real.
The cultural moment was real.
The financial consequences were real.
And those realities could exist simultaneously without making the underlying narrative entirely true.
Perhaps that's one of the gifts of having lived through several cycles, as you observed at the beginning of our conversation.
You can appreciate the music without assuming everyone in the mosh pit is your friend.
You can admire the rebellion without believing every rebel is a hero.
And you can recognize that sometimes the people shouting loudest about defeating the establishment are simply hoping you'll buy their shares at a higher price.
The difference between a movement and a market frenzy isn't always apparent until the music stops.
And somewhere in the back of the room, your sixth-grade business instructor is standing beside a pile of Hershey's Kisses, smiling quietly.
The old bastard was teaching you more than you knew.
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