With Steve Jobs reinstated as CEO of Apple, the path ahead became smoother. His leadership ensured that Apple's trajectory was secure, and my 5 percent stake now carried not just financial value but strategic influence. Jobs owed me a favor, and I knew that meant I could act decisively behind the scenes while he handled day-to-day innovation. I could be peaceful, focused, and patient, waiting for the right moment to strike.
By early 1999, the dotcom bubble had reached a fever pitch. Stocks of tech companies soared astronomically, fueled by hype rather than fundamentals. My net worth had quietly surpassed $2 billion, but I was far from complacent. I understood the inherent risk — the bubble would eventually burst, and those who failed to act would lose fortunes overnight.
I employed a calculated strategy. To maintain appearances and keep my moves under the radar, I intentionally produced a few mediocre startup projects and sold them at slight losses. It was a small price to pay to preserve anonymity and avoid attracting excessive attention from competitors, regulators, or the media. Meanwhile, I began liquidating the bulk of my stock holdings, retaining Apple only for the long-term. After accounting for taxes, I had roughly $1 billion in cash, a formidable war chest. Though the tax burden stung — a significant slice of my gains was surrendered — I knew that liquidity was power.
With this capital, I acted quickly. About $30 million was used to acquire prime real estate in the Indiana Island region of Florida, a location favored by billionaires for its security and discretion. This became a personal sanctuary, a "billionaire bunker" where I could operate with privacy and focus, waiting for the inevitable market correction.
I also began preparing for personal security. Recognizing the visibility and influence I had accumulated, I hired six bodyguards, structuring a loyalty incentive: if they served faithfully for fifteen years, each would receive $10 million upon departure. This ensured absolute loyalty and discretion, giving me peace of mind as I navigated high-stakes investments.
At the same time, I continued to diversify strategically. With Peter Thiel, I invested in PayPal stock, recognizing the potential of digital payments long before mainstream adoption. I had already established substantial wealth, but building an empire required careful allocation, timing, and foresight. A private jet was next, a practical tool for efficiency and mobility, as well as a symbol of the lifestyle and freedom my strategy had secured.
Then the crash came — inevitable, yet perfectly timed. Wall Street and NASDAQ plunged, sending shockwaves across the market. Many investors panicked, selling at fire-sale prices, their fortunes evaporating overnight. For me, it was opportunity. I quietly acquired Microsoft stock, Wells Fargo shares, and other undervalued assets, taking advantage of the market's fear to strengthen my holdings at a fraction of their intrinsic value. I deliberately avoided becoming an early Google shareholder — my strategy was selective, focused, and precise, prioritizing long-term dominance over short-term hype.
By the end of 1999, I had not only preserved wealth but positioned myself for exponential growth in the 2000s. A billion in cash, Apple for decades, selective acquisitions at market lows, and strategic alliances with innovators like Peter Thiel had solidified my empire. While many wept over losses, I quietly prepared for the next chapter, knowing that patience, planning, and calculated audacity were the true currencies of enduring wealth.