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Home » Deep Briefs »  » How to Invest Through a Crash: 3 Rules From the Worst-Timed Investor Alive

How to Invest Through a Crash: 3 Rules From the Worst-Timed Investor Alive

Published: Oct 16, 2026 
Disclosure: Briefs Finance is not a broker-dealer or investment adviser. All content is general information and for educational purposes only, not individualized advice or recommendations to buy or sell any security. Investing involves significant risk, including possible loss of principal, and past performance does not guarantee future results. You are solely responsible for your investment decisions and should consult a licensed financial, legal, or tax professional before acting on any information provided.
Summary:
  • Meet Bunty, a fictional investor with the worst timing in history: he put $100,000 into the market in four chunks right before four crashes, never sold, and by 2025 it had grown to more than $500,000.
  • Investors who jump in and out of the market miss its best days, and missing just a handful of those days can cut your final result roughly in half.
  • The fix is ABB, Always Be Buying: you buy on a schedule through booms, crashes and scary headlines, which matches the market, and beating it takes knowing where the money is moving first.

Investing money is scary. What happens if you pick the wrong stock? What happens if the stock market crashes?

Sorry to be the bearer of bad news, but the market will crash again.

The way you build wealth in the stock market is not by predicting crashes (that's impossible). It's by using market crashes when they are happening.

Just take a look at Bunty.

Bunty is quite possibly the worst investor of all time.

He invested his money four times... each time at the worst possible moment.

And each time, he invested more money than the time before.

Bunty is not a real person. Our founder, Jaspreet Singh, made him up to teach a lesson. He's the "broke cousin" of the family.

Meet the Investor With the World's Worst Timing

It's 1987. Bunty decided to make his first investment and put $10,000 in the stock market.

Then Black Monday hit, the biggest one-day stock market crash in history.

Just like that, Bunty's new investment got crushed.

A lot of people would sell everything and never touch stocks again.

Not Bunty. He didn't sell a single share. He just held on and didn't buy anything new until he felt confident enough to invest again.

It's the year 2000, and he makes his second investment of $20,000, right before the dot-com bubble burst.

It was an exciting time. But immediately after his investment, tech stocks came crashing down.

And Bunty's $20,000 investment went down with them.

In 2008, he made his third investment, this time with $30,000. You can guess what happens next.

He invested right before the financial crisis. It was the worst financial crisis since the Great Depression.

Then in 2020, he makes his fourth investment of $40,000. Weeks later, the pandemic hits, and markets around the world fall off a cliff.

Here's his full track record:

Year What happened right after he bought What Bunty invested
1987 Black Monday $10,000
2000 The dot-com bubble burst $20,000
2008 The financial crisis $30,000
2020 The pandemic crash $40,000

Add it up: Bunty invested $100,000. Every single dollar went in right before a crash. And through all four crashes, he never sold a single share.

So why should you care about Bunty?

Because if timing decided who profits in the stock market, Bunty should have been wiped out four times.

He wasn't. By 2025, the man with the world's worst timing had grown his $100,000 into more than $500,000.

But that's not all. If he had reinvested his dividends, his investment would have grown to $1,000,000.

And that brings us to the three rules of investing.

Rule 1: Don't Panic in a Crash

Bunty had the worst timing possible, but he did one thing right:

He never sold.

A crash only becomes a real loss on the day you sell. Obviously this only holds true if you own good investments that are not on the verge of bankruptcy.

The world's best investors know this, which is why you don't see them running for the exits when the market drops.

The investors who actually lose money in a crash are the ones who sell before it recovers.

Rule 2: Stop Trying to Pick the Perfect Moment

Investors who jump in and out of the market, buying when things look good, then selling as soon as they get scary, aren't investors. They're gamblers.

And most people who gamble lose.

JPMorgan found that if you invested $10,000 into the S&P 500 in 2005, after 20 years it grew to $71,750.

But if you missed just the 10 best days, your money would only grow to $32,871. You would have lost more than half your gains.

If you missed the 60 best days, you'd only have $4,712. You would have lost more than half your money.

And the best days hide right next to the worst ones. Seven of the 10 best days came within about two weeks of the 10 worst.

Rule 3: Always Be Buying

Don't try to time the market by picking the "perfect moment."

Instead, buy on a schedule. Buy through booms, crashes, and every scary headline in between.

At Briefs Finance, we call it ABB: Always Be Buying.

Here's what ABB really does: it takes the emotion out of the choice.

So what do you actually buy?

The simplest starting point is an index fund. That's one fund that buys you a tiny piece of the whole market at once.

An S&P 500 index fund, for example, gives you a small piece of 500 large U.S. companies in one purchase.

Fair warning: ABB is boring. Nobody brags about buying the same fund every month.

But boring is the point. Excitement is what makes investors do expensive things at the worst times.

The Floor and the Ceiling

We covered three general rules of investing so far.

  • Rule 1: Never panic. A crash only becomes a real loss on the day you sell.
  • Rule 2: Don't time the market. Missing a handful of the market's best days can cut your result roughly in half.
  • Rule 3: Always Be Buying. Buy on a schedule, and buy the sale when the market hands you one.

Follow those three rules and you've built the floor.

But notice what the floor gets you: the market's average.

For your parents and grandparents, getting the market's average was enough.

Nowadays with the rising cost of living, the market average might not be enough.

To beat the average, you need something Bunty never had: an edge.

An edge means putting some of your money where the money is moving, before the crowd catches on.

What an Edge Looks Like

Researching a stock is hard. You have to be able to read income statements, listen to earnings calls, and study where the economy is moving.

This research is how we started as a company. Our team of analysts would travel around the world looking for investment opportunities.

Now, we've been able to turn our research into a proprietary stock research platform.

It's called Briefs Investor.

With Briefs Investor you can study thousands of stocks with the click of a button because you get access to two powerful tools.

  1. Briefs Score
  2. Briefs Connector (we call it Supercharging Your AI)

Let's start with the Briefs Score.

Every stock gets a Briefs Score. The Briefs Score gives you an A-F rating on over 2,000 publicly traded stocks.

What makes the Briefs Score so special? Most scoring tools are one-size-fits-all. We grade stocks differently.

Each stock gets a different grade based on its ability to beat the market (growth), pay a strong dividend (income), and protect your wealth during a market crash (wealth preservation).

But that's not all. Our analysts are actually visiting companies in person, seeing how they operate, and looking at market shifts happening right now, then feeding that data you can't get anywhere else into the score on a regular basis.

Doing this research would normally take hours, days, or even weeks to complete.

With the Briefs Score, you can do it in seconds.

Supercharge Your AI

Many people ask ChatGPT or Claude about their investments. The problem is that the AI tools are running based on what's popular on the internet or hitting the headlines.

And AI can only access limited financial data (like what someone could find by Googling a company's financial statements, earnings transcripts, and historical data).

Not anymore.

You can supercharge your favorite AI like ChatGPT or Claude with our Briefs Connector, which includes the Briefs Score and other stock data to get significantly better answers.

We call it supercharging your AI.

And if you don't use an AI platform like ChatGPT or Claude, you're not out of luck. We have our own built-in AI chatbot that you can use too.

Want to learn more about Briefs Investor? You can see all it has to offer here.

The tools you get with Briefs Investor give you an edge to be a smarter and more confident investor.


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