One money tip that’s usually worth heeding is to get professional assistance in managing your finances. After all, you’ll surely do better if you lean on the wisdom of those who know more, right?
In a lot of cases, yes — popular advice often becomes popular because it works. But self-made millionaires tend to be mavericks who aren’t big on conforming to conventional wisdom, and many of them earn their riches by thinking and operating outside the box.
GOBankingRates spoke with two people who built seven-figure fortunes that surely would have eluded them had they stuck to the script and heeded the prevailing financial orthodoxy. They were only able to succeed in the end because they passed on the well-intentioned but wrongheaded money tips they received on the way up.
Chris Kille is a veteran entrepreneur and the driving force behind two successful startups: Payment Pilot is a payment processing and lending company for businesses and their clients. Elevate Outsourcing matches executives, entrepreneurs and other busy professionals with virtual assistants.
A University of South Florida graduate, Kille’s other ventures include the Physicians Payment Group, which he founded in 2015 and continues presiding over as president, and Bark Central Doggie Daycare and Boarding Resort, where he remains a partner. He was previously a managing partner for a company called South Tampa Party Bus and has volunteered at the YMCA for nine years.
“I’m always looking for ways to innovate and stay ahead of the curve in my industry,” Kille said. “Above all, I believe in a strong work ethic and strive to inspire and excel in business every day.”
What he does not believe in, however, is following the herd and heeding boilerplate money advice designed for the masses.
Kille’s entrepreneurial star rose alongside FIRE and similar movements that advocate for wealth-building through extraordinary financial austerity.
Kille wasn’t buying it.
“While the world was busy preaching about extreme frugality — cutting out lattes and couponing — I swerved the other way,” he said. “I invested in things that upped my earning potential — a career coach, quality work attire and networking events.”
Kille said that looking back, he’s grateful for choosing to spend money on revenue generation instead of pinching pennies to increase savings.
“It fast-tracked my journey to a seven-figure income,” he said.
The term “diversified portfolio” is so commonplace that it’s almost a cliche. While it’s wise to mitigate risk and volatility by spreading out your investments, the standard more-is-better diversification advice ignores a key fact — there is such a thing as over-diversification, which can actually heighten your risk while diminishing returns and increasing transaction costs and tax bills.
Kille saw through the prevailing wisdom and adopted a philosophy of what he calls, “diversify, but not too much.”
“Over-diversifying in the name of ‘safety’ initially diluted my returns,” he said. “Stick to four or five assets you understand deeply. High mastery will yield high returns. Don’t let the fear of loss make you lose out on potential gains.”
Craig Cooke started his journey to a seven-figure net worth as a pioneer in the wild and risky early days of the internet, when he founded a digital marketing agency called Rhythm in 1996.
He spent nearly a quarter-century building and growing the company before selling it to Code and Theory, a world-renowned digital creative agency, in 2019. He stayed on as CEO for three years before moving into the consulting field and launching C-Squared Professional Consulting. He is also releasing a book later this year.
He’s set himself up for a cushy retirement — but he had to buck conventional retirement planning wisdom to do it.
If he had listened to advice, Cooke would have entered adult life in search of a high salary from a company that offered a retirement plan with an employer match to his contributions. But his entrepreneurial spirit gave him other ideas.
“Instead, I started my own business and made investments into stocks and real estate before I ever set up a 401(k) through my own company,” Cooke said. “However, even with my own company’s 401(k), I made minor investments and focused on using my monetary resources on building my real estate portfolio and adding other vehicles such as equity-indexed life insurance.”
Today, Cooke looks back with gratitude that his younger self had the foresight to go against the grain and take calculated risks instead of going with the flow.
“I was able to become a multi-millionaire as my investments into myself, my company and various investments have paid off, creating abundance for me and my family,” he said.
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