Save and Invest

8 self-made millionaires reveal the worst money mistakes they made when they were younger

Illustration: The Oracles

Even the world's richest people weren't born with financially savvy skills. That's why, if you aspire to be wealthy, it's important to learn from the mistakes they made on their journey to wealth.

We asked eight self-made millionaires and Advisors in The Oracles to share the worst money mistakes they regret making when they were younger — and how it's changed their financial beliefs today:

1. 'I spent $71,000 on a bad marketing campaign.'

"I believe money is meant to be spent, so I've never been good at saving. But I wish I hadn't spent The Corcoran Group's first big profit on a marketing campaign that flopped.

When I put all our real estate listings on videotapes with their respective agents, I didn't anticipate that none of my agents would want to hand out tapes with competitor agents on them. I was so sure of the idea that I didn't stop to think of the consequences before spending $71,000.

Luckily, I saved face by uploading the videos onto the Internet. All of my best successes happen on the heels of failure."

Barbara Corcoran, founder of The Corcoran Group; podcast host of "Business Unusual"; investor on "Shark Tank."

2. 'I spent too much time and money trying to hire the wrong people.'

"When I was younger, I hesitated to invest in myself and thought I needed the security of a paycheck. When I finally took the leap to start my own beverage company, I spent a lot of time trying to hire people with more experience.

But the 'experts' wanted to compromise on what made our beverages successful: We don't use sweeteners. The lesson? I had to do it myself.

Ultimately, Hint thrived because we defied industry standards and stayed true to our mission — helping people lead healthier lives without compromising on enjoyment." 

—Kara Goldin, founder and CEO of Hint Inc.; creator of The Kara Network, a digital resource for entrepreneurs; host of the "Unstoppable" podcast. Follow her on Twitter and Instagram.

3. 'I maxed out my credit cards living above my means.'

"My first job after college was in commission sales. When I crushed my quota, I spent like a king. When sales were sluggish, I tried to maintain that lifestyle using credit cards. As sales slowed with the recession, I maxed out all my cards and was down to my last $3.73.

When I had to ask my father to give me a loan, I felt like a failure. But he helped me out and ultimately taught me to live beneath my means. That spark helped me get debt-free and showed me the freedom of financial wellness."

Michael O'Brien, executive business coach; author of "Shift: Creating Better Tomorrows"; founder of Peloton Coaching and Consulting and The Pace Line Leadership Academy. Follow him on Facebook and LinkedIn.

4. 'I didn't invest in my physical and mental health.'

"My mistake was thinking short-term instead of planning for the future. For example, I didn't hire a personal trainer because it seemed expensive — but that investment would have paid dividends, and the opportunity costs were huge.

Now I know that when I'm not physically fit and spiritually and emotionally calm, my mind is sluggish. So I judge every decision against whether it will matter in 12 months and double down on what adds value in my life to generate overall wealth instead of immediate income."

—James Mansfield, founder and CEO of JGMansfield and West Village General Contracting. Follow him on LinkedIn and Instagram.

5. 'I overspent without having a financial buffer.'

"When I started making money, I spent it on my passions and helping friends and family before I saved enough, rather than invest it to generate more revenue. I thought the money would keep flowing and didn't prepare for challenges.

When they came, I lost 85% of my income and found myself struggling. Create a financial buffer before anything else — or have a solid plan to generate a return on your passion."

— Craig Handley, co-founder of ListenTrust; author of "Hired to Quit, Inspired to Stay." Follow him on LinkedIn.

6. 'I fell victim to lifestyle inflation.'

"When I started making six figures, I shifted my spending to match my income, rather than save the difference. Living a lavish life was a bad idea because I always had a lingering fear that my money would one day disappear. 

So I set up automatic deposits to invest when money was deposited into my account. Over time, I became more disciplined, and now I invest and save much more than I spend."

Sarah Chrisp, founder of Wholesale Ted, one of the largest online educational resources; started her first online store at 16 years old. Follow her on YouTube.

7. 'I didn't learn the basics of accounting.'

"If someone had told me how important accounting is, my first two businesses wouldn't have failed. I just saw sales and money in the bank, so I thought I was doing great.

But when I suddenly saw the real numbers, the reality of the situation was quite different. I wish I had learned sooner that while you don't have to become an accountant yourself, the basic principles of accounting are critical to success."

—Bill Gerber, co-founder of AccountingDepartment.com, a virtual accounting service for small businesses. Follow him on LinkedIn.

8. 'I took out student loans for the wrong reasons.'

"When I started day trading, I was working for minimum wage and needed money. So I took out $25,000 in student loans to trade with — and I lost it in a month.

I wish someone had told me not to try to move so quickly, but we live in a society that wants immediate results. Sometimes you need to be patient, and other times you should move fast. The key is learning to tell the difference."

—Marcello Arrambide, founder of Day Trading Academy; co-founder of SpeedUpTrader, a funding company for aspiring day traders. Follow him on Instagram and LinkedIn.

The Oracles is a mastermind group of the world's leading entrepreneurs who share their success strategies to help others grow their businesses and build better lives. Follow The Oracles on FacebookTwitter, and LinkedIn.

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This is "Shark Tank" investor Barbara Corcoran's $3,000 regret
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