Insiders betting on Musk are reaping "historic returns."

Original丨Li Hailun

The largest initial public offering (IPO) in history has entered the countdown phase. SpaceX, owned by Elon Musk, is expected to price its IPO on June 12 and begin trading the following day.

Investors are anchoring a valuation of about $2 trillion. If calculated this way, Musk himself will directly become the world's first trillionaire. However, the real drama of this deal is that the wealth will not flow solely to Musk. With the disclosure of the prospectus, a group of loyal aides and early allies who have long been in Musk's shadow are seeing the value of their holdings surface for the first time.

Their "loyalty" and patience are yielding the most generous returns in history.

01 Musk's "Shadow Partners"

Among all those who will gain immense wealth from the SpaceX IPO, Antonio Gracias has the most unique identity. He is not a company employee but is more deeply embedded in Musk's business empire than most executives.

The 55-year-old Gracias is the founder of the Chicago investment firm Valor Equity Partners. The two met through a Silicon Valley network formed during the PayPal transactions in the early 21st century. At that time, Musk had just sold the company to eBay, while Gracias was running his own investment firm, Valor Equity Partners.

During Tesla's near bankruptcy from 2008 to early 2009, Gracias personally lent Musk $1 million. Since then, he has become one of Musk's closest private friends. He was also the best man at Kimbal Musk's wedding (Musk's brother), and the two families have even vacationed together.

This two-decade-long friendship is now translating into an astonishing fortune. Gracias holds over 500 million shares of SpaceX Class A stock through investment entities associated with Valor, accounting for about 7.3% of the company's Class A shares, making him the second-largest individual shareholder after Musk.

Based on a conservative valuation of $1.5 trillion, these shares are worth about $91.6 billion. If valued at $2 trillion, they exceed $140 billion. Regardless of where the final pricing lands, he will rank among the 50 richest people in the world.

Gracias appears on the boards of nearly all of Musk's companies. He served as Tesla's chief independent director for eight years and has been a director at SolarCity, Neuralink, and The Boring Company. He even agreed to finance Musk's failed attempt to acquire OpenAI for $97 billion in early 2025.

The financial relationship between Gracias and SpaceX is not limited to equity. The prospectus revealed an unusual arrangement. In October 2025, a subsidiary of xAI named CTC signed a lease agreement for AI infrastructure hardware with Valor. In January and April 2026, the two parties signed a second and third lease agreement, respectively. The three agreements require CTC to pay nearly $20 billion to Valor during the term, with SpaceX itself providing full guarantees for these payments.

This means that if xAI's subsidiary is unable to make payments, SpaceX has a legal obligation to pay on its behalf. Such guarantees signal that xAI may not be able to secure this level of financing on its own credit and requires intervention from the parent company. In fact, documents show that xAI is heavily indebted, including secured senior notes with interest rates as high as 12.5%. This is typically the pricing level for borrowers in financial distress, indicating that the company is struggling to secure typical financing.

The structure of these transactions has raised the attention of auditing firms. SpaceX's auditor, PwC, refused to classify these agreements as ordinary leases and instead characterized them as "failed sale-leasebacks."

In a conventional sale-leaseback, one party sells an asset to another and then leases it back for use, requiring the buyer to actually gain control of the asset. However, PwC believes that the contract terms allow CTC to retain actual control over the GPU, meaning that Valor's role is closer to that of a lender with GPU as collateral. The auditors forced SpaceX to keep this $9 billion debt on its balance sheet, listed as payable to entities where company directors serve.

02 SpaceX President and COO

Among all the soon-to-be billionaires, Gwynne Shotwell's story is the most representative. At 62 years old, she joined the company in 2002, ranking as employee number 11.

Shotwell's initial task was to secure sales orders for the then-obscure Falcon 1 rocket. More than twenty years later, she is the company's president and chief operating officer, frequently attending various industry events while Musk diverts his attention to other companies, becoming the de facto public spokesperson for SpaceX.

According to the prospectus, Shotwell directly or through trust funds holds 12.4 million shares of SpaceX and has 4.7 million stock options. If the company prices at a $2 trillion valuation, the value of her shares alone would reach about $2 billion. Shotwell's total compensation for 2025 was $85.8 million, primarily from substantial restricted stock awards.

Born in Illinois, she studied mechanical engineering and applied mathematics at Northwestern University, starting her career in the airline industry, working on thermal analysis and small spacecraft design.

After meeting Musk in 2002, she quickly joined SpaceX and was promoted to president in 2008. For this engineer, who has bet her entire career on a company once mocked as a "madman's dream," this wealth represents a form of delayed recognition.

03 SpaceX CFO

Compared to the frequently public-facing Shotwell, Brett Johnson is more like the financial steward within SpaceX, responsible for sustaining the capital lifeline of this cash-burning company.

He joined SpaceX in 2011, having spent nearly a decade in finance at Broadcom and semiconductor company Mindspeed. During SpaceX's long years of secretive operations and financial performance, Johnson was the main contact for answering all tricky questions and coordinating stock transactions.

In December 2025, Johnson sent out a memo outlining the reasons for the company's IPO to employees. In it, he wrote, "Our thought is that if we execute very well and the market cooperates, the public offering can raise a lot of money."

Johnson holds about 9.6 million shares of SpaceX stock. Based on a $2 trillion valuation, this portion of shares is worth about $1.4 billion. His total compensation for 2025 was $9.8 million.

04 "PayPal Mafia"

Luke Nosek's connection with Musk dates back to the PayPal era. He is a co-founder of PayPal and served as vice president of marketing and strategy, also being a core member of the so-called "PayPal Mafia."

In 2002, when eBay announced and completed its acquisition of PayPal, Nosek co-founded Founders Fund with Peter Thiel and others, leading the first investment of Founders Fund in SpaceX in 2008. He subsequently obtained a board seat and has held it ever since.

Afterward, Nosek left Founders Fund to establish his own venture capital firm, Gigafund, investing over $1 billion in SpaceX, while also supporting Neuralink and The Boring Company.

Nosek directly holds nearly 25 million shares of SpaceX Class A stock and holds another approximately 8 million shares through Nosek Capital. Based on a $2 trillion valuation, the total value of his holdings is about $5.3 billion. Similar to Musk, Nosek has pledged nearly 2.4 million shares of SpaceX as loan collateral.

05 Institutional Players and University Funds

Beyond the wealth stories of individual shareholders, the shareholder roster of SpaceX prominently features some institutional players.

Donald Harrison, as a Google executive, represents this early institutional investor on the SpaceX board. Steve Jurvetson, co-founder of Founders Fund, has been a long-time ally of Musk, serving as a director since 2009.

Venture capitalist Ira Ehrenpreis joined the board in February 2026, expected to serve as chair of the compensation and nomination committee. Randy Glein, co-founder of DFJ Growth, became a director in 2026 after serving as a board observer for a long time and will chair the audit committee. Ehrenpreis holds about 1.37 million shares of SpaceX, valued at approximately $250 million based on conservative estimates; Glein holds about 278,000 shares, valued at around $50 million.

An even more dramatic story involves higher education institutions. Scott Wilson, the chief investment officer at the University of Washington, invested about $50 million of the school's funds into SpaceX about ten years ago. This bet has now soared to over 10% of the school's $17 billion endowment, primarily through co-investments and later-stage investments involving external private equity and venture capital managers.

Anders Hall, the investment director at Vanderbilt University, estimates the school's position in SpaceX at $171 million, with some investments completed over a decade ago through relationships with general partners. The school's total endowment as of June 2025 was $10.9 billion.

However, the massive IPO payouts are a double-edged sword for endowments. They will receive a large influx of cash, but a few of the wealthiest private schools will need to pay higher net investment income taxes. The U.S. Congress has raised the tax rate from 1.4% to 4% or 8%, depending on the size of the school.

06 AI Racking Up Sky-High Bills

The IPO of SpaceX reveals not only the wealth opportunities for a few but also the company's awkward financial reality.

This rocket and artificial intelligence company has yet to turn a profit and is spending money at a rate far exceeding its revenue generation. In 2025, the company lost $4.9 billion for the year. In just the first three months of 2026, it lost $4.3 billion on revenues of $4.7 billion.

Annual revenue is growing at about 33%, while capital expenditures are doubling each year. In 2025, SpaceX spent $20.7 billion, with about 60% invested in artificial intelligence. In the first three months of 2026, the company has already spent $10.1 billion, with $7.7 billion flowing into the AI sector.

Once listed, all these debt and expenditure pressures will shift to public shareholders. They will also inherit billions of dollars in debt obligations arising from a series of transactions made during SpaceX's private period, including leases with Valor.

In the prospectus, one clause is particularly eye-catching: once 1 million people live on Mars, Musk will receive up to a billion additional shares, which are already included in his large pool of voting rights sufficient to control the company.

For a company that has been losing money for years, investors will have to make their judgments between aggressive spending, massive losses, and a governance structure entirely controlled by insiders.