5 Self-Made Millionaires Share the Best Ways They Ever Spent a Paycheck
Written by
Marc Guberti
Edited by
Rebekah Evans
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It takes a lot of time and effort to become a self-made millionaire. Many of these people make big investments in themselves that set them up for long-term success. Some of these investments have a different impact on their careers, while other millionaires are happy about personal expenses, which gives them a deeper perspective of the world.
Some self-made millionaires took the time to share the best ways they have ever spent a paycheck — here are the results.
In contrast, here are the best ways to spend your paycheck when your salary barely covers your expenses.
Pursuing a Challenge
Not all investments have a tangible impact on your career or business. Some self-made millionaires make investments in the intangibles that don’t appear to impact the business on the surface. However, accomplishing a big challenge can make business obstacles seem easier to overcome.
Gene Caballero is the co-founder of GreenPal, a platform that connects homeowners with lawn care professionals. He explained why using his earnings to climb Mount Kilimanjaro was the best investment he made.
“Climbing Mount Kilimanjaro was the best way I ever spent a paycheck. My Kilimanjaro adventure pushed me to new physical and mental boundaries which were similar to challenges faced in entrepreneurship. The demanding altitude and the need for endurance during the climb taught me that success requires discipline and resilience in both business and life,” he said.
“Climbing to the top taught me about personal boundaries because I faced discomfort and demonstrated that determination makes all things achievable,” he added. “The value derived from experiences far surpasses that of material possessions because they determine your personal development.”
A Family Vacation
Two self-made millionaires cited a family vacation as the best way they spent their earnings. Dielle Charon is a certified life coach and seven-figure sales expert for WOC coaches. She explains how covering her family’s vacation had a huge impact on her and created a new standard for her family.
“The best way I spent a paycheck was taking my entire family (including mother, aunts, etcetera) on a trip that I paid for. Growing up, we did not have the kind of money for this kind of thing,” she said. “This is why the work that I do is so powerful. I want families of color to have the wealth that they dream of and these opportunities. This was a powerful moment for me to see the change in generations this business is bringing.”
Sophie Musumeci, founder of Real Entrepreneur Women, an organization dedicated to helping women create profitable businesses around their purpose, also mentioned a family vacation as the best money she has spent.
“One of the best ways I’ve ever spent a paycheck was booking a family trip to Europe — without having to check price tags, without hesitation, just saying yes to the experience. Years ago, that would have felt impossible,” she said.
“I remember a time when every dollar had to be stretched, every expense questioned,” she added. “But when I built my coaching business to seven figures, I realized wealth isn’t just about money in the bank — it’s about choice. That paycheck wasn’t just about flights or hotels; it was about giving my family the experience of freedom.”
Business Acquisitions
Two self-made millionaires mentioned business acquisitions as their best investments. These investments align more with generating a direct ROI than intangible benefits.
Harry Morton is the CEO of Lower Street, a podcast production company. The firm recently acquired Canadian-based Pacific Content, which he views as his best investment.
“I always put aside a part of my paycheck for speculative opportunities. This paid off when the opportunity to buy Pacific Content arose. Being financially prepared meant I could act without hesitation,” he said.
“It wasn’t just about growing the business. It was about retaining top talent, building expertise and positioning Lower Street as the number one branded podcast company,” he added. “You can think of savings as just putting money away, but it’s actually buying future opportunities. This is something I’ll continue to do because I can never be prepared enough. While there are other sources of funding, it’s simply better to have your own resources ready. It gives you control, speed and the ability to seize opportunities without hesitation.”
While Morton carefully calculated this acquisition, it was the opposite for the next self-made millionaire on this list. Nikita Khandheria is the owner of ERIA Food, a company that stands at the forefront of innovation in the food industry. She explained how an investment made on a whim resulted in big profits.
“After a few too many drinks, I impulsively bought a few laundromats. I wasn’t entirely sure what I was doing, but I figured, ‘Hey, how bad can a laundromat be?’ Turns out, pretty good. After some strategic TLC and a bit of elbow grease, I sold them for a tidy profit,” Khandheria said.
You don’t have to consume alcohol to come up with a great business idea, but Khandheria’s story demonstrates that sometimes it’s better to jump into the action instead of overthinking it and missing out on the opportunity.
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