Experts Reveal the Best Investments They Ever Made

©Richard Drew/AP/REX/Shutterstock

©Richard Drew/AP/REX/Shutterstock

The idea of investing your money — and potentially increasing its value — is an attractive one. However, making intelligent investments is easier said than done.

GOBankingRates asked financial experts about the best investments they ever made and looked at other successful individuals to see what they had to say about their smartest financial decisions.

Click through to read their responses, and learn how you can start investing.


Investing With an Index Fund

At first glance, you might not think that mohawk-sporting, smooth-talking J. Money is the type of person to make sound financial decisions. However, this financial rock star and super-blogger got famous by posting his net worth monthly for the world to see. In seven years, his followers watched him save $400,000.

Blogging today at Budgets Are Sexy, Money offers sound financial advice and investing tips. When asked about the best investment he ever made, he recommended against chasing long shots.

“The best thing I’ve ever done with my money is invest it in Vanguard Index Funds. I spent so many years chasing the hottest stock and trying to beat the market when I should have been ignoring it all and just dumping my money right into the market overall. And don’t even get me started on the fees that companies and funds charge,” he said.

Just getting started? Click to see the best online stock brokers for beginners.

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Planning for Retirement

“My best investment decision was investing early and often,” said Wes Moss, a financial whiz and host of “Money Matters,” the nation’s longest-running live investment and personal finance radio show. “Since I started working, I’ve made a point to put money into my retirement savings accounts, and as I’ve gotten older I’ve continued to challenge myself by investing even more towards my future.”

Moss also touts the value of investing in real estate. In fact, his personal real estate investments are among his most lucrative.

“I believe it’s been successful because I enjoy living in more urban areas, which in recent years have been popular, leading to more appreciation. It’s been a wonderful experience enjoying and valuing my homes for their utility, but then having the surprising financial payoff when it was time for us to move,” he said.

Related: The Best Traditional IRA Accounts for Your Retirement Nest Egg


Not Putting Off a Goal

A money expert for millennials, Stefanie O’Connell is an acclaimed professional speaker and author of “The Broke and Beautiful Life.” She’s worked with universities and Fortune 500 companies alike, but her true passion lies in helping people achieve financial greatness.

O’Connell attributes her own success to one simple decision that didn’t seem so obvious at the time: “My best investment decision was getting started. It was 2010, I was two years out of college, and we were all still reeling from the financial crisis. But I had just read my first personal finance book, and it inspired me to open up a Roth IRA,” she said.

“It’s one of the best decisions I ever made; the market gains have been huge, and now I’m in the habit of investing,” she added. With that in mind, O’Connell advises aspiring entrepreneurs to start now.

If you’re looking for an even easier way to get started, you can use a robo-advisor to start investing.

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Investing in Your Children

Business owner, financial guru and mother of four, Lauren Greutman helps women live better lives for less through her website LaurenGreutman.com. When asked about her best investment ever, she didn’t name stocks or bonds.

“My best investment decision is sending my kids to a small, private Christian school,” she said. “We pay more for this school every month than we do for our mortgage, but it is so important. It is a huge investment in the four most important people in our lives: our children.”

Although Greutman and her husband have had to make some sacrifices for their kids’ schooling, she believes they have all been worth it. But if you’re single, there’s no harm in investing in yourself and your future.

Look into some of the best investments you can make no matter how much money you have to invest.


Following a Passion

Kyle Taylor, founder and CEO of the personal finance website The Penny Hoarder, said, “I made an early decision to invest in my passions.” For him, that meant entering the political sphere.

During his first semester of college, he got a call from a political group needing a motorcade driver. Taylor took the job and soon found himself dropping out of college to work for campaigns full time. He refers to this period of his life as a valuable investment.

“I know this experience isn’t for everyone, but my early door-to-door campaigning taught me how to interact with people and sell an idea,” he said. “I learned humor is a great weapon. In fact, I still use that on sales calls at The Penny Hoarder. A joke or two always helps to lighten the mood. I owe a lot of my success today to my early experiences,” he said.

So, look to turn your hobby into a side hustle or business. You might find, over time, you have the opportunity to make a sizable income doing what you love most.

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Choosing the Right Real Estate

Financial expert and best-selling author David Bach knows a thing or two about making money. He’s appeared on NBC’s “Today Show,” “The Oprah Winfrey Show” and numerous other TV shows. When asked about the best investment decision he ever made, he told GOBankingRates, “The best investment decisions I’ve made over my lifetime have been the homes I bought and lived in.

“From my first apartment in San Francisco to the apartments that I’ve lived in in Manhattan, simply owning my apartment and living in them have turned out to be just fantastic multimillion-dollar decisions because the value of my property has gone up so much, which is why I always say one of the most important investment decisions you’ll ever make is the home you buy and live in,” he said.


Investing Time Instead of Spending It

A money expert, blogger and financial consultant, John Rampton got his start the hard way. While working on a construction site to pay for college, he was in an accident that severely injured his left leg. Told he would never walk again, Rampton spent a year in bed.

While no one would wish to endure what Rampton did, he managed to turn this setback into an opportunity by investing in his education. “I could’ve spent that time feeling sorry for myself or watching TV,” said Rampton. “Instead I spent 16 to 20 hours a day teaching myself about online marketing. That was the jump-start to my career.”

Since then, he has started several companies and was named one of the world’s top three most influential marketers by Entrepreneur Magazine. He also defied the odds by learning to walk again.

His advice? “Always invest your time; don’t spend it,” he said.

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Buying a Home Instead of Renting One

Financial expert and author of “How to Be a Financial Grownup,” Bobbi Rebell is an award-winning journalist and advocate for financial literacy. Rebell also hosts her own podcast, “Financial Grownup,” where she interviews other financial experts and asks them to share some of their most notable money stories.

Despite this long list of professional achievements, Rebell reports that her best investment is one a little closer to home.

“My best investment, as I discuss in ‘How to be a Financial Grownup,’ was my decision to buy real estate as a young adult,” said Rebell. “That early decision to pay a mortgage rather than rent has been by far the best financial decision of my life. I have traded up three times now and was fortunate to make a profit each time, giving me significant equity in my home.”

Find Your State: The Cost of Renting vs. Owning a Home in Every State


Attending a Seminar

With a net worth of around $500 million, Tony Robbins certainly knows how to invest his money. But that wasn’t always the case. In fact, the New York Times No. 1 best-selling author said he was directionless in high school.

In an interview with investor and podcaster Tim Ferriss, Robbins said that, when he was 17, he helped his father’s friend move, and everything changed. Robbins’ father told him the friend was now successful but used to be a “loser.” When Robbins asked what happened, the friend said he attended a seminar by author and speaker Jim Rohn. At the time, Robbins earned just $40 a week, and he spent $35 to attend the seminar.

“I wrestled for a week with that decision, because it seemed like such a giant decision,” Robbins told Ferriss. “I look back on it now as one of the most important decisions of my life, because that night stimulated me. Jim Rohn became a model of what was possible to me.”

So, the best investment Robbins ever made cost under $50. As you face financial challenges, he says to focus on what you can control and the results.

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Selling a Company

The owner of the Dallas Mavericks, Mark Cuban, boasts a $3.9 billion fortune and a serious amount of investment expertise. He attributes at least some of his success to smart timing.

Cuban’s first big business move was launching Broadcast.com in the 1990s. That company, which showed sporting events online, grew successful enough that Yahoo bought it for $5.7 billion in 1999. However, Cuban’s investment savvy didn’t stop there.

Foreseeing the dot-com crash, Cuban sold 100 percent of his shares for a cut of $2.5 billion. Shortly after, Yahoo’s stock crashed 95 percent. That’s called good timing, but Cuban also advises you learn to choose solid investments.

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Not Listening to the Naysayers

Some uncertainty exists about President Donald Trump’s true net worth. However, most agree his wealth is substantial. Trump’s most savvy investment was likely his bet on Manhattan real estate in the 1970s. At the time, Manhattan real estate was in free fall.

However, Trump wrote in his book “The Art of the Deal” that he saw the plummeting prices as an opportunity. He invested $200 million in Manhattan real estate — a sum worth about $800 million today — and the decision paid off. Manhattan real estate prices went up 6,000 percent from 1973 to today, according to Business Insider.

Click through to learn how to chose the best investments.

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