Why You Should Chase Windfalls

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Stolen TikTok slop reupload and passed-off as original Twitter slop.

That’s the catalyst for today’s special report.

One of Twitter’s many viral content mills recently posted a TikTok video where some influencer went around and asked fast food employees if they'd quit their job for $200,000 in cash.

The video itself is unimportant. What is important, however, were the comments.

Almost every reply was someone praising the various employees who turned down the offer. Many commentors said things like “That’s smart because you’d have to pay tax on that $200,000.” Others stated that “It’s better to have a steady job than a one-time payment.”

Which leads to an extremely common personal financial fallacy…

One that hinders many people.

And that’s the inability to sell out.

A one-time payment can absolutely change your life.

The SPDR S&P 500 ETF $SPY ( ▼ 0.03% ) delivered a 10-year average annual total return of 14.65%.

Someone who received a one-time, post-tax, windfall of $100,000 and invested it in a low-cost S&P 500 index fund would now have over $392,000.

And someone who received a post-tax windfall of $10,000 and invested into the S&P 500 would now have a little over $39,255.

Is $392,000 enough to retire on?

Probably not, unless you’re living frugally in Northern Thailand or small town Mexico. But it is enough money to alleviate a lot of financial stress. And, left alone, that one-time windfall can easily compound into the seven figure range.

$392,000 growing at 9% for 15 years is $1,427,853. And that’s assuming the market slowed down and only delivered single-digit annual returns for over a decade. At a 12% average annual total return, your $392,000 balance grows to over $2,000,000 within 15 years.

Of course, past performance doesn’t guarantee future returns.

So, let’s say you received a $100,000 windfall today and over the next 25 years the S&P 500 delivers a 10% average annual total return.

That $100,000 would ultimately grow to over $1,083,470.

Even a $10,000 windfall compounding at 10% per year for 25 years ultimately grows to more than $108,000.

So how do you maximize your chances of receiving a one-time windfall?

There are several options.

You could invent something…

Bill Lear, inventor of the Learjet and 8-track tape, once said that the fastest way to make money was to “invent something that people wanted.” This could be something technological, but it could also be something like a book or song or toy. Kasing Lung is a multibillionaire off his invention of the Labubu plush toy.

You could work in a hot field…

When an industry is red-hot, it’s often impossible to not make money in that field.

People often laugh about random businesses that slap “AI” or “Blockchain” on their name. but companies do this because it works. And sometimes these trends become so ubiquitous that you can capitalize on them from anywhere. In the book Guerrilla Marketing, there’s an anecdote about an entrepreneur who cashed-in on the dot-com bubble by starting a business called “I Will Teach You About Computers” which offered lessons for senior citizens who wanted to send emails or go online.

You could build and sell a business…

Have you ever heard of The Points Guy? It was one of the first credit card review sites. The owner would recommend various credit cards and financial products, while using referral links that earned a commission on each sign-up. Today, this is an extremely common business model. But at the time, this was a largely untapped niche. And The Points Guy founder, Brian Kelly, was able to leverage his website’s success by selling The Points Guy for $20 million to Bankrate, LLC. Even if you don’t build a multimillion dollar business, many YouTube channels and Instagram pages sell for 2-3 times their earnings.

You could buy low and sell high…

In 1984, Paramount Pictures was cleaning out some old storage facilities. One of the cleaners asked filmmaker Joe Dante if Dante would like any of the old movie props that the studio was throwing away. One of these props was the “Rosebud” sled from Citizen Kane. Dante took the sled. And in 2025, Joe Dante sold “Rosebud” at auction for $14.75 million. While you may not get an iconic movie prop for free, you can always keep your eyes open for items that are extremely valuable to the right people.

Windfalls can create life-changing money.

It’s good to keep your eyes open for opportunities where you can earn an extra one-time payout of five, six, or even seven figures. This money, invested wisely, can blossom into a sizable nest egg for the long-term.

7 Ways to Take Control of Your Legacy

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Inside, you’ll find {straightforward advice} on tackling key documents to clearly spell out your wishes.

Plus, there’s help for having those all-important family conversations about your financial legacy to make sure everyone’s on the same page (and avoid negative future surprises).

Why leave things to chance when you can take control? Explore ways to start, review or refine your estate plan today with The Investor’s Guide to Estate Planning.

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Disclaimer: This article is for entertainment purposes only. It is not financial advice, always do your own research.