Insiders who bet on Elon Musk are reaping "historic returns."

Elon Musk and his inner circle. From left to right in the back row are Antonio Gracias, Gwynne Shotwell, Brett Johansen, and Luke Nosek. The picture has been processed by AI.

The largest initial public offering (IPO) in global history has entered the countdown stage. SpaceX, under Elon Musk, is expected to price its IPO on June 12 and start trading the next day.

Investors are targeting a valuation of around $2 trillion. If so, Musk himself will directly become the world's first trillionaire. However, the real drama of this deal lies in the fact that the wealth won't just flow to Musk alone. With the disclosure of the prospectus, the value of the shares held by a group of loyal deputies and early allies who have long hidden behind Musk has surfaced for the first time.

Their "loyalty" and patience are now being rewarded with the most generous returns in history.

01 Musk's "Shadow Partners"

Among all those who will gain huge wealth from SpaceX's IPO, Antonio Gracias has the most special status.

He is not a company employee, but he is more deeply embedded in Musk's business empire than most executives.

Gracias, 55, is the founder of Chicago-based investment firm Valor Equity Partners. The two met through the Silicon Valley network formed after PayPal transactions in the early 2000s. At that time, Musk had just sold his company to eBay, while Gracias was running his own investment firm, Valor Equity Partners.

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

This twenty-year friendship is now turning into an astonishing fortune. Gracias, through investment entities associated with Valor, holds more than 500 million Class A shares of SpaceX, accounting for about 7.3% of the company's Class A shares and 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 are worth more than $140 billion. No matter where the final price falls, he will be among the world's 50 richest people.

Gracias appears on the boards of almost all of Musk's companies. He served as Tesla's chief independent chairman for eight years and is a director at SolarCity, Neuralink, and The Boring Company. He even agreed in early 2025 to finance Musk's unsuccessful $97 billion hostile takeover plan of OpenAI.

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

This means that if xAI's subsidiary is unable to pay, SpaceX has a legal obligation to pay on its behalf. Such a guarantee itself sends a signal that xAI may not be able to obtain financing of this magnitude on its own credit and needs the parent company to intervene. In fact, the documents show that xAI is heavily in debt, including secured senior notes with an interest rate as high as 12.5%. This is usually the pricing level for borrowers in financial distress, indicating that the company has difficulty in typical financing.

The structure of these transactions has alerted the auditing agency. PwC, SpaceX's auditor, refused to treat these agreements as ordinary leases and instead classified them as "failed sale-leasebacks."

In a regular sale-leaseback, one party sells an asset to another and then leases it back for use, and the buyer needs to actually obtain control of the asset. However, PwC believes that the contract terms allow CTC to retain actual control of the GPUs, which means that Valor's role is more like a lender using GPUs as collateral. The auditor forced SpaceX to keep this $9 billion debt on its balance sheet as related-party debt payable to an entity where a company director serves.

02 SpaceX President and COO

Among all the upcoming new billionaires, Gwynne Shotwell's story is the most representative. At 62, she joined the company in 2002 with employee number 11.

Shotwell's initial task was to secure sales orders for the then-unknown Falcon 1 rocket. More than twenty years later, she is now the company's president and chief operating officer. While Musk has been spreading his energy across other companies, she has frequently attended various industry events and has become the de facto public face of SpaceX.

According to the prospectus, Shotwell directly or through a trust fund holds 12.4 million shares of SpaceX and 4.7 million stock options. If the company is priced at a $2 trillion valuation, the value of her shares alone will reach about $2 billion. Shotwell's total compensation in 2025 was $85.8 million, mainly from a large number of restricted stock awards.

Shotwell was born in Illinois. She studied mechanical engineering and applied mathematics at Northwestern University and started her career in the airline industry, engaged in thermal analysis and small spacecraft design.

She met Musk in 2002 and 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 "crazy dream," this wealth represents a long-overdue recognition.

03 SpaceX CFO

Compared with Shotwell, who frequently appears in public, Johansen is more like the financial steward inside SpaceX, responsible for supporting the capital lifeline of this high-burn company.

He joined SpaceX in 2011 after spending nearly a decade in the financial field at Broadcom and semiconductor company Mindspeed. During the long years when SpaceX operated in secrecy and kept its financial performance under wraps, Johansen was the main contact for answering all the tough questions and coordinating stock transactions.

In December 2025, it was Johansen who sent employees a memo outlining the reasons for the company's listing. He wrote in it: "Our thinking is that if we execute very well and the market cooperates, a public offering can raise a large amount of capital."

Johansen holds about 9.6 million shares of SpaceX. Based on a $2 trillion valuation, the value of these shares is about $1.4 billion. His total compensation in 2025 was $9.8 million.

04 "The PayPal Mafia"

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

In 2002, eBay announced and completed the acquisition of PayPal. Nosek co-founded Founders Fund with Peter Thiel and others and led Founders Fund's first investment in SpaceX in 2008. He immediately obtained a seat on the board of directors and has held it ever since.

After that, Nosek left Founders Fund and founded his own venture capital firm, Gigafund, and invested more than $1 billion in SpaceX. He also supported Neuralink and The Boring Company.

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

05 Institutional Players and University Funds

Beyond the wealth stories of individual shareholders, the names of some institutional players are also prominently listed on SpaceX's shareholder roster.

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

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

A more dramatic story involves higher education institutions. Scott Wilson, the chief investment officer of the University of Washington, invested about $50 million of the school's funds in SpaceX about a decade ago. This bet has now soared to more than 10% of the school's $17 billion endowment fund assets, mainly through co-investments and late-round investments through external private equity and venture capital managers.

Anders Hall, the investment director of Vanderbilt University, said that the school's position in SpaceX is estimated to be $171 million, and part of the investment was made more than a decade ago through relationships with general partners. The school's total endowment fund as of June 2025 was $10.9 billion.

However, the huge IPO dividends are a double-edged sword for endowment funds. They will receive a large amount of cash inflow, but a few of the wealthiest private schools will need to pay a higher net investment income tax. 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 Burns Up a Sky-High Bill

What SpaceX's IPO reveals is not only the opportunity for a few people to get rich overnight but also the company's embarrassing financial reality.

This rocket and artificial intelligence company has not yet achieved profitability, and it is spending money much faster than it is making money. In the whole year of 2025, the company lost $4.9 billion. And in just the first three months of 2026, it lost $4.3 billion on the basis of $4.7 billion in revenue.

Its annual revenue is growing at a rate of about 33%, but its capital expenditure is doubling every year. In 2025, SpaceX spent $20.7 billion, about 60% of which was invested in artificial intelligence. In the first three months of 2026, the company had spent $10.1 billion, of which $7.7 billion went to the AI field.

Once listed, all these debt and expenditure pressures will be transferred to public shareholders. They will also inherit billions of dollars in debt obligations arising from a series of transactions SpaceX made during its private period, including the lease with Valor.

In the prospectus, there is a clause that is particularly eye-catching: Once one million people live on Mars, Musk will receive up to one billion additional shares, and these shares are now already included in his large voting rights pool that is sufficient to control the company.

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

Special translator Jin Lu also contributed to this article.

This article is from the WeChat official account "Tencent Technology", author: Helen Li. It is published by 36Kr with authorization.