I’m a Self-Made Millionaire: 5 Biggest Financial Risks I Took in Order To Become Rich

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In the realm of financial success and building wealth, the journey is often paved with calculated risks and strategic decisions that set the stage for remarkable achievements. The people who challenge conventions and embrace calculated gambles are ultimately the ones who end up with the most money in the bank.

GOBankingRates talked to two exceptional individuals who defied the odds and transformed their financial destinies through a fearless approach to risk-taking. By listening to their stories, you’ll uncover invaluable insights, tips and tricks to help you along in your own financial journey. Prepare to be inspired by these trailblazers as we get a glimpse of the calculated gambles that paved their way to prosperity.

Gene Caballero, co-founder of GreenPal, a website and mobile app-based platform that connects homeowners with local lawn care professionals, says his road to becoming a millionaire was “not without its share of significant risks that shook me to my core but also propelled me toward success.” Here are the three biggest risks he took.

I Quit My Corporate Job

Caballero said walking away from a steady six-figure income and the security of health benefits was a monumental risk. The job provided a financial cushion, but it also sucked away the time and energy he needed to make GreenPal a reality.

“The day I handed in my resignation was fraught with anxiety, but it was the first crucial step in dedicating myself wholly to my own venture,” he shared. Only after doing that could he start building the future he imagined for so long.

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I Sold My House

Caballero emphasizes that selling his house wasn’t just parting with a valuable asset, but also embarking on a phase of life characterized by unpredictability. The funds generated from the sale served as the essential seed capital that powered GreenPal’s operations.

Although it was emotionally and financially taxing, it was an indispensable step in establishing the capital foundation he required. “I loved my house, but I loved the vision of what GreenPal could become even more,” said Caballero.

I Went Into Personal Debt of $200K

Perhaps the most anxiety-inducing risk was going into a staggering amount of personal debt, said Caballero. “This was not just a number on paper; it was a looming obligation that could ruin me financially if GreenPal didn’t work out,” he shared. Caballero leveraged multiple credit lines to provide the business with the resources it needed to scale and grow, even as the weight of potential failure hung over him.

Fortunately, the gamble paid off. “Today, GreenPal has grown into a business generating over $30 million in annual revenue and growing at over 25% year over year,” he shared. “Risk is scary, but it’s often the price of admission for something far greater.”

Likewise, Adam Nager, founder and CEO of Medical Billing Opportunity, took some of the same risks as Caballero, including leaving a six-figure job that included healthcare benefits to focus 100 percent of his time on his new business. He also took a couple more risks. 

I Took Out a Loan

Nager embarked on his entrepreneurial journey with a bold move — securing a business loan tied directly to his personal assets. This decision showcased his unwavering commitment to realizing his vision, yet it came with significant risks.

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By linking his personal assets to the success of his new venture, Nager not only demonstrated his belief in its potential but also shouldered the profound responsibility of making it thrive. Such a financial commitment underscores the sacrifices and dedication often required in entrepreneurship, highlighting the courage it takes to bet on oneself in the world of business.

I Swallowed My Pride

Nager took a big chance by telling people what he was up to and reaching out for help. He even connected with folks he didn’t get along with in the past, putting aside any hard feelings.

Surprisingly, these renewed connections turned out to be incredibly beneficial in his business journey. This shows that making amends and working together with people, even if you didn’t get along before, can lead to big opportunities and success in the business world. Nager’s story teaches us that being open to change and working with others can go a long way in entrepreneurship.

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