Homeschooling Mom Stunned by $18M Stock Windfall — What Dave Ramsey Advises Next

Imagine coming across a long-forgotten account and realizing it holds millions of dollars. That’s exactly what happened to Sarah, a 50-year-old mother from Seattle. She had been homeschooling her children for two decades when she checked in on an employee benefits account from her previous job at a tech company. This discovery led her to reach out to The Ramsey Show for guidance.

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Sarah’s account had grown from nearly nothing to about $18 million, according to her conversation with Dave Ramsey. While she didn’t reveal the specific company, some online commenters speculated that it could be Nvidia, a tech giant that has seen significant growth in recent years.

Regardless of the company, Sarah admitted she was unsure how to handle her sudden wealth. Ramsey provided some key advice.

Diversify and Withdraw in a Tax-Conscious Way

Having so much of your net worth tied up in a single stock is “scary and unwise,” Ramsey said. He advised Sarah to sell some shares and invest the money elsewhere. However, given the size of the fortune, selling even a portion would likely push her into the top tax bracket.

According to the Internal Revenue Service, the highest possible federal capital gains tax rate for someone in this bracket is typically 20%. Depending on where you live, you may also face state taxes on your capital gains from selling long-term investments. For Sarah, in Washington state, that’s another 7%.

While Ramsey suggested consulting a financial expert to minimize her tax bill, he emphasized the urgency of the situation. He insisted that Sarah diversify away from a single stock as soon as possible.

“If I’m you, even if it costs me some money, I would rather have the safety than I would the extra 20%,” Ramsey told her.

Read More: 5 essential moves to make once you’ve saved $50,000

Get in Touch with an Expert

Consulting a financial planner, as Ramsey recommended, can help you optimize your portfolio so that your net worth isn’t dependent on just one stock or asset. You can find fiduciary financial advisors near you through Advisor.com. With no fees to get started, Advisor.com matches you with up to three FINRA/SEC registered advisors suited to your needs.

From there, you can book a free, no-obligation consultation with your preferred advisor. They can help you build a diversified portfolio that meets your financial goals without taking on excessive risk. Plus, working with a financial advisor can even result in better returns. According to research from Vanguard, clients who worked with fiduciary experts saw 3% higher net returns on average compared with those who didn’t.

Beyond the Importance of Diversification

Sarah’s story offers another lesson for investors: the value of holding instead of folding. Time in the market is better than timing the market.

An often-repeated tenet of investing is that “time in the market beats timing the market.” This principle was popularized by investing experts such as Warren Buffett and is based on the fact that most investors struggle to find the right stock at the right time and at the right price.

By focusing on a longer timeline, rather than optimizing around short-term gains, investors can take advantage of the market’s tendency to go up in the long-term. When investors try to time the market, they can end up buying at a peak and selling in a valley. Investing consistently can help your portfolio better manage the ebbs and flows of the market over time, delivering compound returns.

Buffett once said in an interview with Public Broadcasting Service (PBS), “I don’t try and guess when to get in and out of the market.”

Rather, Buffett’s investing philosophy is best captured by a quote from his 1989 Letter to Shareholders for Berkshire Hathaway: “It’s far better to buy a wonderful company at a fair price than a fair company at a wonderful price.”

In Sarah’s case, this type of “set and forget” approach seems to have panned out. But in case of a market downturn, she’d risk losing millions. Instead, a safer approach for many could be to invest regularly in an array of stocks or low-cost index funds, which can offer better diversification and wealth preservation.

Focus on Quality, Not Quantity

Another Buffett ethos is that you should invest in stocks that are priced based on solid fundamentals, rather than investing in a stock simply because it’s cheap. But digging through stocks and companies takes time and effort. That’s where platforms like Moby can help you find top-tier stocks, delivered straight to you for review.

The platform offers expert research and recommendations to help you identify strong, long-term investments backed by advice from former hedge fund analysts. In four years, and across almost 400 stock picks, their recommendations have beaten the S&P 500 by almost 12% on average. They also offer a 30-day money-back guarantee.

Moby’s team spends hundreds of hours sifting through financial news and data to provide you with stock and crypto reports delivered straight to you. Their research can keep you up-to-the-minute on market shifts and help you reduce the guesswork behind choosing stocks and ETFs. Plus, their reports are easy to understand for beginners, so you can become a smarter investor in just five minutes.

Build Consistent Investing Habits

According to a Fidelity report using Bloomberg data, trying to buy and sell stocks at just the right moment can cost you — big time. If you invested $10,000 in the S&P 500 in January 1988 and kept your money in for all of the booms and busts, it would be worth $522,576 today. Meanwhile, if you were buying and selling stock during that period of time and inadvertently missed just the best five days in the market, you’d be down a whopping 37%, with $330,060 to your name instead.

It’s a strong example demonstrating the power of compound growth over a long-term investing horizon. You can build consistent, sustainable investing habits with Acorns, an app that automatically invests spare change from everyday purchases into a smart portfolio of ETFs.

Here’s how it works — when you buy a coffee for $4.25, Acorns will automatically round up the purchase to $5 and invest the 75-cent difference into a diversified portfolio. Just $2.75 worth of daily round-ups total over $1,000 in a year — and that’s before it earns money in the market. The S&P 500 index has delivered an average annual return of over 10% since 1957. Although past performance is not an indicator of future returns, if we were to assume a similar rate of return over the next 20 years, your net balance would be around $57,275.

Even better, when you sign up now with Acorns with a recurring deposit, you can get a $20 bonus investment to get you started.

Diversifying Outside the Stock Market

Not only is the bulk of Sarah’s wealth tied up in a single stock, but it’s also stuck in the market itself. She’s not just at the whim of the company performing well. She’s also reliant on the market’s consistency as a whole.

And according to Goldman Sachs CEO David Solomon, “It’s likely there’ll be a 10 to 20% drawdown in equity markets sometime in the next 12 to 24 months.”

If that turns out to be true, diversification isn’t just ‘smart’ — it’s essential. However, there are plenty of different assets worth considering outside of stocks. And they are becoming easier to leverage through new platforms and investing opportunities.

A Finer Alternative Asset

While billionaires like Jeff Bezos and Bill Gates continue to invest heavily in stocks, they also carve out a portion of their portfolios for assets that behave differently from the market. One standout example is a globally recognized asset class that, until recently, was the domain of the ultra-rich. This asset type has even outpaced the S&P 500 by 15% from 1995 to 2025 while showing near-zero correlation to traditional equities.

The investment in question? Art. Until recently, this world was off-limits. Now, with Masterworks, you can buy fractional shares in multimillion-dollar works by icons like Banksy, Picasso and Basquiat. While art can be illiquid and typically requires a long-term hold, it offers unique portfolio diversification.

Masterworks has sold 25 artworks so far, yielding net annualized returns like 14.6%, 17.6% and 17.8% among assets held for longer than a year. Even better, you can get priority access to diversify with art by skipping the waitlist today.

Note that past performance is not indicative of future returns. Investing involves risk. See important Regulation A disclosures at Masterworks.com/cd

Consider Adding Real Estate to Your Portfolio

According to the U.S. Census Bureau, monthly rental costs increased in 20% of American counties between 2020 and 2024, compared to the previous five years. While that might be frustrating news for renters, there are also ways to benefit from this increase — if you see it as an investment opportunity.

For instance, you can access this market by investing in shares of vacation homes or rental properties through Arrived. Backed by world-class investors, including Jeff Bezos, Arrived allows you to invest in shares of vacation and rental properties, earning a passive income stream without the extra work that comes with being a landlord of your own rental property.

To get started, simply browse through their selection of vetted properties, each picked for their potential appreciation and income-generating power. Once you choose a property, you can start investing with as little as $100, potentially earning quarterly dividends.

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