10 Bold Money Moves That Turned Regular People Into Millionaires

​Achieving millionaire status often involves making bold financial decisions that deviate from conventional wisdom. Here are ten daring money moves that transformed ordinary individuals into millionaires:​

1. Investing in Undervalued Stocks During Economic Downturns

An investor analyzing stock charts during a market downturn
Pexels

Sir John Templeton made a fortune by purchasing shares of companies trading below $1 during the Great Depression, demonstrating the potential of investing when others are fearful.​

2. Leveraging Real Estate at a Young Age

Young adults discussing property investments
Pexels

Ruth and Becky Shipley began their property investment journey at age 20, eventually building a portfolio worth over £2 million and achieving financial freedom.

3. Dropping Out of College to Pursue Entrepreneurship

Young entrepreneurs brainstorming in a startup environment
Pexels

Patrick Collison left MIT to co-found Stripe, a fintech company now valued at billions, illustrating the rewards of pursuing entrepreneurial ventures over traditional education paths.

4. Transforming a Modest Gift into a Trading Fortune

A trader monitoring multiple screens with stock data
Pexels

Timothy Sykes turned a $12,415 Bar Mitzvah gift into over $1 million through penny stock trading, highlighting the potential of strategic investing.

5. Capitalizing on Emerging Markets

An investor researching international markets
Pexels

Sir John Templeton pioneered globally diversified mutual funds, investing early in markets like Japan, which contributed significantly to his wealth.

6. Building a Business in a Niche Industry

Entrepreneurs discussing business strategies in a specialized field
Pexels

Shawn Meaike transitioned from social work to founding successful businesses in life insurance and waste management, leading to substantial wealth.

7. Participating in Experimental Investment Programs

People sitting with arms raised in meeting in office
Pexels

Richard Dennis trained novices, known as the “Turtles,” in commodities trading, many of whom became millionaires by following his trend-following strategies.

8. Pursuing Passion Projects with Business Potential

An individual working on a creative project in a home studio
Pexels

David Geffen’s passion for music led him to establish record labels and amass significant wealth by signing major artists.

Read More: 10 Tiny Money Mistakes That Can Ruin Your Retirement Dreams

9. Embracing High-Risk, High-Reward Investment Vehicles

A man holding a paper
Pexels

Chamath Palihapitiya utilized special-purpose acquisition companies (SPACs) to democratize investments in high-growth startups, accruing substantial wealth.

Read More: 10 Signs It’s Time to Change Your Career

10. Prioritizing Financial Education and Strategic Planning

Man sitting on sofa while reading a book
Pexels

Grant Sabatier educated himself on personal finance, leading to financial independence and millionaire status by age 30.​

These examples underscore the importance of bold, informed decisions and the willingness to take calculated risks in the journey toward financial success.

Read More: 10 Retirement Myths That Are Keeping You Broke

About the Writer

Jim Price

Jim Price is a Midwestern husband and father with a passion for helping readers navigate the worlds of finance and career growth. With a practical approach and real-world insights, he breaks down complex topics into actionable advice, empowering others to make informed decisions about their money and professional lives.

The Latest

A couple looking over finances
The 7 Most Overrated Budgeting Hacks That Don’t Actually Work
Sarah Blakely
How Spanx Founder Sara Blakely Became the Youngest Self-Made Female Billionaire in the World
man holding phone white using MacBook
The 10 Most Lucrative Side Hustles That Aren’t Just Another Scam
man kissing woman's forehead white holding ultrasound photo
The 10 Most Common Budget Mistakes New Parents Make
An empty gym with unused equipment
15 Money Traps Hiding in Your Everyday Routine