Self-Made Millionaires Reveal the Best Investments They’ve Made
Written by
Heather Altamirano
Edited by
Brendan McGinley
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In a time of rapid economic shifts and uncertainty, it can feel like building wealth is impossible, but achieving self-made millionaire status in the U.S. isn’t out of reach or unattainable. In fact, according to a UBS Global Wealth Management study there are over 24 million millionaires in the United States. While the exact number of self-made millionaires is harder to pinpoint, one thing is clear: many followed the same smart habits like living minimally, a strong work ethic, setting financial goals, avoiding debt and taking calculated risks with stocks, which helped accelerate their financial success.
To help others make sound investments, self-made millionaires are opening up about their journeys and sharing what their best stock investments are. Whether you’re just getting started or looking to grow your portfolio, their stories are packed with practical tips, real-world lessons and a dose of inspiration.
Why Holding Microsoft Changed Everything
Peter Diamond is a federally licensed tax, accounting, real estate and structure and certified bankability expert, as well as a self-made millionaire. However, when he was starting out, he made several mistakes with his investments due to a lack of patience.
“What I eventually learned is that time is always your best friend in investing,” he said. “If you can hold on, you’ll win in the end.”
The lesson came from a simple oversight. Diamond had been actively trading through his TD Ameritrade account and didn’t give any time for his investments to compound. But one stock–Microsoft–slipped through the cracks. He unintentionally left it sitting for years and he earned a massive return as a result, teaching him the unexpected value of restraint.
“The moral of the story is to always invest for the long haul, regardless of the asset class and let compounding do its thing,” he said.
Spotting a Tech Innovation Early: The Move That Tripled Returns
Kris Dehnert is the CEO of Dugout Mugs and the first person in his family to reach millionaire status. He made his fortune through his business as well as investing heavily in several start-ups, such as HBAR, the cryptocurrency used by Hedera Hashgraph, a crypto-trading alternative to blockchain-based systems.
“I recognized HBAR as a solid investment as soon as I heard the founder speak at a mastermind event I was attending and understood its utility,” he said.
Hedera’s cryptograph network offers extremely fast, secure transactions with very low transaction fees — often just fractions of a cent. These features make it well-suited for applications needing high throughput, predictable costs and tokenization tools.
“I knew larger groups would see use cases down the road, and they did! Today, companies like Google, Boeing, IBM, Dell, Swift and Nvidia are all utilizing this technology,” Dehnert said. He invested $100,000 in 2021 and has tripled his money.
How Index Fund VTI Was a Game Changer
Steven and Lauren Keys are a millionaire couple who retired at 29 years old and started the blog Trip Of a Lifestyle, which offers financial tips to help others make money and travel more. The pair lived below their means and invested 60 percent to 80 percent of their education salaries in stocks and bond index funds to build wealth. Their focus is on reliable, steady growth rather than riskier opportunities to make life-changing gains.
“The biggest return has been from VTI, which is an exchange-traded index fund that contains virtually every public company in the United States under one ticker symbol,” Steven Keys explained.
“Index funds like VTI are amazing because they capture the average return of the entire stock market in one place, effortlessly,” he said. “Instead of trying to get lucky by picking winning stocks, I simply buy them all, capturing a powerful positive return through a well-diversified portfolio, automatically.”
He added, “I profit from the stock market without ever having to think about it!”
Every millionaire’s path is different, but the right investment can change everything.
