Jaina Anne grew up in a Navy family where money was scarce and the wealthy were viewed with suspicion. The 2020 market crash jolted her into seeking financial literacy, leading from Palantir stocks to Ethereum mining to real estate investing. A chance conversation about a $38,000 Indiana house shattered her California assumptions and launched her into building a 10-property portfolio using creative financing. Now she teaches real estate investors how to turn contractor payments into luxury vacations while challenging the millennial fear of taking calculated risks.