2 Self-Made Millionaires Reveal the First Jobs That Paved the Way to Riches
Written by
Cindy Lamothe
Edited by
Amber Barkley
Commitment to Our Readers
GOBankingRates' editorial team is committed to bringing you unbiased reviews and information. We use data-driven methodologies to evaluate financial products and services - our reviews and ratings are not influenced by advertisers. You can read more about our editorial guidelines and our products and services review methodology.
20 Years
Helping You Live Richer
Reviewed
by Experts
Trusted by
Millions of Readers
Ever wonder where today’s self-made millionaires got their start? It’s easy to imagine everyone with wealth was born that way, but sometimes it comes down to raw talent and serious focus.
One surprising fact? A 2022 study published by Wealth-X found that around 68% of those with a net worth of $30 million or more made it themselves.
GOBankingRates spoke with self-made millionaires Justin Crabbe, CEO and founder of BlackJet, and Andrew Lokenauth, money expert and owner of BeFluentInFinance, who shared the first jobs that taught them hustle, grit — and maybe even a thing or two about money.
The Line Technician Who Leveraged Skills and Relationships
“I got my first professional job as a line technician at a small regional airport,” said Crabbe. “I was in charge of basic maintenance duties, directing planes on the tarmac and fueling aircraft.”
Making the Right Connections
He said the exposure was priceless, but the remuneration was meager. He dealt with mechanics, pilots and sometimes aircraft owners on a daily basis. “I listened to their discussions on flight dynamics, weather patterns and engine performance.”
Over time, Crabbe would read the flight manuals and maintenance records of the aircraft he serviced while working night shifts. After hours, the chief mechanic took notice of his curiosity and started teaching him the fundamentals of aircraft repair.
“I gained technical expertise from this unofficial apprenticeship that would later be very helpful to me in assessing aircraft purchases and fleet maintenance procedures,” Crabbe explained.
Taking Opportunities
After three years, Crabbe leveraged this experience to become a dispatcher for a charter service. He said this role taught him the business side of aviation — scheduling, logistics, customer service and profit margins.
He began to see how the industry functioned as a business, not just a passion. “I started noticing inefficiencies in operations that could be improved for better profitability.”
The most valuable skill he developed during these early jobs wasn’t technical knowledge or business acumen — it was relationship building. Crabbe made it his mission to know everyone in the regional aviation community.
Starting a Business
When he eventually secured funding to purchase his first small aircraft for charter services, these relationships provided his initial client base.
“My big break came when I identified a gap in the market for specialized maintenance services for certain aircraft models,” he explained.
He said the technical knowledge from his line technician days, combined with the business understanding from dispatching, allowed him to build a maintenance operation that quickly became the preferred service provider for several regional carriers.
“This profitable maintenance business generated the capital that funded my expansion into aircraft leasing, charter services and eventually manufacturing components,” he said. “Each step built on skills I had developed sweeping hangar floors and answering phones in those first humble jobs.”
The Investment Banker Who Valued Mindset and Networking
On the other hand, Lokenauth started his career on Wall Street, working crazy 100-plus-hour weeks.
Those first few years were brutal, he explained, basically living at the office, surviving on coffee and takeout. “But looking back, that’s where I learned the skills that really set me up to build serious wealth.”
Picking Up Skills
Investment banking taught Lokenauth how to analyze companies and spot opportunities that others missed. He’d spend countless nights building complex financial models and doing deep dives into different industries.
This knowledge, he explained, became absolutely crucial later, when he started making his own investments. “I remember one deal where we valued a mid-sized tech company — the intensive research process I learned there helped me spot similar opportunities years later that generated $500,000 plus in personal returns.”
Building Relationships
Similar to Crabbe, working on Wall Street allowed Lokenauth to build relationships with major institutional investors and learn how the big money really moves in financial markets.
Those connections proved invaluable.
“And the negotiation skills I picked up — you wouldn’t believe how much psychology goes into closing nine-figure deals,” he explained. “I still use those same techniques today in my business ventures.”
His time at JP Morgan Asset Management was where everything clicked. Managing portfolios for high-net-worth clients showed him exactly how wealthy people think about and grow their money.
“I saw firsthand which strategies actually worked versus what was just marketing hype. This knowledge fundamentally shaped my own wealth-building approach,” he said.
High Starting Pay Plus the Right Mindset
The pay was solid, too — starting at $85,000 base plus $30,000 bonus, growing to $200,000-plus total comp within three years.
But he said the real value was the skills and mindset. Learning to work under extreme pressure, think strategically about risk vs. reward and spot opportunities others missed. That foundation made all the difference.
“So even though those early years were intense,” Lokenauth explained, “they gave me the tools to build serious wealth later on. The technical skills, yes, but more importantly the way of thinking about money and business opportunities.”
He even said some of his old colleagues became important business partners down the road. “Your network really is your net worth in finance.”
While the stress and long hours weren’t fun, Lokenauth said they taught him discipline and showed him what he was capable of. “When you’ve survived 100-hour weeks as a 22-year-old analyst, starting your own business doesn’t seem so daunting. Sometimes the hardest experiences end up being the most valuable. That’s definitely true of my early Wall Street days.”
More From GOBankingRates
