Does the Bigger Bankroll Always Win? A Man Who Bought Nokia Every Month Waited 25 Years to Break Even

Contents

1. The day he bought the top
2. The first time it felt wrong
3. The year he finally came out ahead
4. The ones that made it, and the ones that didn’t
5. Why more money can’t save you: one roulette calculation
6. Further thoughts: stuck in a losing position, should you average down?
7. One thing to take with you

When you bet with tiles, you are skillful; bet with belt buckles, and you grow anxious; bet with gold, and you lose your head.

—— Zhuangzi, “Mastering Life” (4th century BC; translation mine)

Zhuangzi’s point was that the gambler’s skill never changes. What changes is how heavy the stake feels. More than two thousand years later, a saying that runs the opposite way is making the rounds online.

The saying goes like this in Chinese internet slang: with a big enough bankroll, you win in the end. Checked against numbers, it is only half right. On a roulette wheel where every bet loses a little on average, walking in with $100 or $10,000 gives you the same roughly 0.45% chance of getting $100 ahead before you go broke. In the stock market, picture someone who started buying Nokia at its June 2000 peak and added a fixed amount every month. Through the close on October 9, 2026, that account was underwater in 83% of its 317 months, sank as low as −81%, and only stayed above water for good after September 2025. A bigger bankroll wins only when the game itself favors you, and when both your money and your life can wait for the payoff.

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The day he bought the top

Let me tell you a story. The man is made up. Every price he lives through is real.

On June 19, 2000, Nokia hit its all-time high. Half the world carried a Nokia, and buying the stock hardly needed a reason. Our man bought that day and set himself a rule: add $1,000 every month from now on, treat every drop as a discount, and never sell at a loss.

That is the plainest version of “the bigger bankroll wins.” His logic sounded fine. Nokia was too big to fail, his paycheck kept coming, and the further it fell the more shares he’d get, dragging his average cost down until the rebound made him whole.

Over the next two years the dot-com bubble burst and Nokia slid. He kept buying and kept telling himself it was cheap.

The first time it felt wrong

In 2007 the iPhone came out. Not many people took it seriously at first, and Nokia’s market share was still huge. Within a few years, though, Nokia had all but vanished from the smartphone fight.

By June 2012 he had been adding for twelve straight years, and the account sat at −81%. Every hundred dollars he’d put in was worth nineteen. It had been twelve years of slow bleeding, and he was still feeding it every month.

Somewhere in there the logic quietly changed. “I have enough money to hold on” became “I’ve put in too much to stop now.” By now he had one reason left to keep buying: he couldn’t accept being wrong.

The year he finally came out ahead

The ending may surprise you: he didn’t lose.

Because he kept buying at low prices for more than a decade, the whole account was up about 93% as of October 9, 2026. His last month underwater was September 2025.

Now count what it cost him. In 83% of those 317 months he was looking at a loss. At the worst moment he was down 81%. The whole thing took twenty-five years. Had he put the same money into the Nasdaq Composite each month instead, his worst drawdown would have been 44%, he’d never have been underwater again after August 2009, and he’d be up roughly 700% today.

He won on paper and lost on life. And he is one of the lucky ones, because Nokia at least survived.

The ones that made it, and the ones that didn’t

When people hear “the bigger bankroll wins,” this is the table they picture: dot-com darlings that fell hard and still came back.

Company	Peak around 2000	Worst drop afterward	Back to peak (dividends reinvested)	Today vs. peak
Amazon	Dec 1999	−94%	Oct 2009	about 49x
Qualcomm	Jan 2000	−87%	Mar 2014	about 3.2x
Microsoft	Dec 1999	−69%	Jul 2014	about 14.8x
Oracle	Sep 2000	−84%	Dec 2014	about 3.9x
Intel	Aug 2000	−82%	Mar 2018	about 2.5x
Cisco	Mar 2000	−89%	Aug 2021	about 2.3x
Nokia	Jun 2000	−96%	not yet	about 0.34x

(Prices through the October 9, 2026 close, dividends reinvested.)

It looks like proof that holding on pays. It hides two traps.

First, even the winners took 9 to 21 years. After losing almost 90%, Cisco didn’t get back to its 2000 high, dividends included, until 2021. A new graduate would have hit middle age waiting.

Second, this table only lists the companies that are still alive. In the same era WorldCom went bankrupt in 2002 and Enron in 2001. Anyone averaging down into them ended at zero, and there was no happy ending to wait for. We remember the names that survived, which is exactly why “just hold on” sounds so convincing.

Why more money can’t save you: one roulette calculation

With the story told, let’s do the math behind it. Roulette has the most transparent rules, so it’s the cleanest place to check.

On a European wheel, a bet on red wins 18 times out of 37, about 48.6%. That sliver below half is the house’s cut. Say you bet $1 at a time and plan to leave once you’re $100 ahead:

Bankroll you bring	Chance of getting $100 ahead before going broke
$100	about 0.45%
$1,000	about 0.45%
$10,000	about 0.45%

A hundred times the bankroll barely moves the odds. Mathematicians call this the gambler’s ruin problem: if each bet loses on average, any finite bankroll eventually goes to zero. The size of the stack only decides how long that takes.

Some people answer: then I’ll double my bet after every loss, and one win gets it all back. Start at $1 and lose ten in a row, and you’re down $1,023 and need to bet $1,024 just to win back a single dollar. Ten straight losses happen about 0.13% of the time. That sounds rare, but play every day for tens of thousands of spins and you’ll hit it, and that’s before the table limit stops you from doubling at all. The strategy wins small almost every time, then one day gives everything back in a single hit.

The casino really is the bigger bankroll that always wins. It just needs two things at once: every bet favors it, and its bankroll is too big for any single bet to break. The bankroll is the second thing. The edge is the first, and it’s what actually matters.

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Further thoughts: stuck in a losing position, should you average down?

This is probably the question on your mind by now. I’d start by splitting it in two.

If you own the broad index, companies as a whole make money over time, so on average the game favors you. That’s where a big bankroll plus patience actually holds up, and it’s why dollar-cost averaging into an index works. Even so, the wait can be long. The Nasdaq Composite took 15 years to reclaim its 2000 high. Japan’s Nikkei peaked at the end of 1989 and didn’t get back there until February 2024, 34 years later.

If you own a single stock, the company can be left behind by its era, dilute you with share offerings, or go bankrupt. Averaging down into a business whose fundamentals have broken means adding money to a game that loses on average. It’s the stock-market version of doubling your roulette bet.

So I think the question to ask is “is the reason I bought this still true?” Whether you still have cash comes second. If the reason holds, a drop is a discount. If it doesn’t, a drop is a warning. Buying more in 2002 was defensible. The real mistake in the Nokia story came later: still saying “it’s too big to fail” around 2010, when smartphones had plainly stopped being Nokia’s game.

One more thing that gets overlooked: being able to stomach it doesn’t mean your money can wait. If you’re on margin, the price can fall far enough that your broker sells you out before any rebound. A down payment, tuition, or a medical bill won’t wait for you to break even. And when an account is down 50%, most people don’t calmly add more. They sell at the bottom. The question worth asking is: in the worst case, would I be forced out at the lowest point?

One thing to take with you

A bigger bankroll only lets you hold on longer; your odds stay exactly where they were. Ask whether the game pays on average before you ask whether your pockets are deep enough.

Next time you’re about to average down, try this: take a sheet of paper and write a single line, “The reason I bought this was ____.” Then go check whether that reason still holds today. It works outside the market too, like before you pour more money into an aging car or give a stalled project one more year. Six months later, read the sheet again, and you’ll know whether you were picking up a bargain or doubling your bet.

Raw Markdown

This article is an educational discussion of investment method. It is not advice to buy or sell any individual security, offers no target prices, and does not analyze any current holding. Investing carries risk; make your own decisions or consult a qualified professional.