I’m a Self-Made Millionaire: The Best $1,000 I Spent Before I Became Rich
Written by
Cindy Lamothe
Edited by
Levi Leidy
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Long before becoming wealthy, one self-made millionaire spent just $1,000 on something that didn’t look impressive at the time — but ended up paying off in ways they never expected.
GOBankingRates spoke with Jon Morgan, co-founder of Venture Smarter, to look back at that early decision and why it mattered more than most people realize.
A $1,000 Legal Decision That Saved Six Figures Later
Morgan advises startups on capital allocation, and his most pivotal $1,000 expense over nine years ago was not on an asset but on specialized legal counsel.
He said investing in the correct business entity structure from day one was critical.
“That single decision prevented what I now estimate would have been over $250,000 in future tax inefficiencies and restructuring costs, directly accelerating my own wealth-building journey by creating a scalable and defensible financial foundation for growth,” he explained.
Wrong Early Structure Can Cost Founders Tens of Thousands
According to Morgan, founders mistakenly prioritize early marketing spend over foundational legal and financial architecture which is a flawed growth model.
“My consulting work confirms that 9 out of 10 early stage companies we analyze have the wrong structure for their long-term goals.”
He explained that correcting this mistake two or three years later costs between $10,000 and $50,000 in legal and accounting fees.
“That initial thousand-dollar investment is not an expense but a direct input into future financial velocity and personal risk mitigation.”
A Flawed Structure Can Kill Funding Before It Starts
“Angel investors and venture capitalists (VCs) will scrutinize your cap table and corporate structure before writing a check, so a flawed setup can terminate a deal instantly,” said Morgan.
Forgoing expert counsel to save money upfront often results in tens of thousands in legal restructuring fees during a first funding round.
He said your first significant investment should be in a structure that protects assets and enables growth, not just in a product that might not even exist in 18 months.
The Bottom Line
For this self-made millionaire, the best $1,000 spent before becoming rich had nothing to do with marketing, scaling or chasing quick wins. It was an early investment in the right legal and financial structure — one that protected assets, reduced risk and positioned the business for long-term growth. That single decision helped avoid costly restructuring, preserved future funding opportunities and saved hundreds of thousands of dollars over time.
The takeaway here is simple: Real wealth is often built by making smart, unglamorous decisions early, long before success becomes visible.
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