Prabowo Widodo
Glen Anderson, a veteran broker of private company shares since 2010, has witnessed a monumental transformation in the late-stage private market. What was once a niche domain serviced by a mere handful of institutional investors has burgeoned into a sprawling ecosystem populated by thousands of sophisticated players. As president of Rainmaker Securities, an investment bank specializing in private securities markets and facilitating transactions in approximately 1,000 stocks, Anderson holds a unique vantage point on the current, highly dynamic secondary market. This moment, he suggests, is defined by three colossal characters: Anthropic, OpenAI, and SpaceX, each playing a distinct role in a storyline far more intricate than surface-level headlines might suggest.
The Evolving Landscape of Private Market Investment
The dramatic expansion of the private market secondary sector over the past decade reflects a broader trend of companies staying private longer, raising substantial capital from private sources, and delaying public listings. This shift has created a robust demand for liquidity solutions for early investors, employees, and founders, giving rise to firms like Rainmaker Securities. In 2010, the concept of a "late-stage private market" was nascent, with limited infrastructure and institutional participation. Today, a complex network of venture capital funds, private equity firms, sovereign wealth funds, family offices, and specialized secondary funds actively trades stakes in high-growth, pre-IPO companies. This maturation has also brought increased scrutiny and sophisticated valuation methodologies to assets that were once opaque.
Anthropic’s Meteoric Rise and Unprecedented Demand
Among the trio, Anthropic, the artificial intelligence research company behind the Claude AI model, currently commands almost insatiable demand in the secondary market. Anderson’s observations at Rainmaker Securities mirror recent reports, including one by Bloomberg earlier this week, highlighting a stark contrast in investor appetite compared to its primary competitor. Ken Smythe, founder and CEO of Next Round Capital, was quoted indicating that buyers had pledged an astounding $2 billion in cash ready for deployment into Anthropic shares. Concurrently, approximately $600 million worth of OpenAI shares struggled to find buyers.
"The hardest stock to source in our marketplace is Anthropic," Anderson told TechCrunch from his Miami home yesterday afternoon. "There’s just no sellers." This scarcity underscores an extraordinary investor confidence, a sentiment amplified by recent events. A significant catalyst for this turbocharged demand, Anderson posits, was Anthropic’s highly publicized standoff with the Department of Defense. Initially, the dispute, which involved concerns over data security and national interest regarding AI model deployment, appeared to be a potential setback. However, it unexpectedly transformed into a public relations boon for the company.
"The app got more popular, people rallied around the company as kind of a hero, taking on big government," Anderson elaborated. "I think it amplified the story and made it even more differentiated from OpenAI." This narrative, portraying Anthropic as an independent, principled entity navigating complex ethical and governmental landscapes, resonated deeply with a segment of investors. It fostered a perception of resilience and a distinct brand identity that set it apart in the increasingly crowded AI sector. This distinction is becoming crucial for investors who, for years, adopted a broad-based "bet on everyone" strategy in emerging tech verticals. While many institutional investors still seek exposure to both Anthropic and OpenAI, acknowledging that "the jury’s still out" on the ultimate AI model winner, the momentum in the secondary market has unequivocally shifted in Anthropic’s favor.
OpenAI’s Shifting Dynamics and Valuation Nuances
Despite Anthropic’s current dominance in secondary market demand, Anderson cautions against a binary interpretation of the situation. "I wouldn’t say it’s a one-or-the-other conversation," he asserted, indicating that OpenAI remains a significant player with substantial underlying value. However, the palpable excitement surrounding OpenAI has waned. "It’s not nearly as vibrant a market as Anthropic right now," he acknowledged, reflecting a cooling in the fervor that once characterized its secondary trading.
On the valuation front, Anderson broadly corroborated Bloomberg’s reporting that OpenAI shares in the secondary market are trading at an implied valuation of approximately $765 billion. This figure represents an appreciable discount to the company’s newest primary-round valuation of $852 billion, a testament to the liquidity premium often demanded by secondary market investors. While working from memory, Anderson affirmed the Bloomberg figure was "in the right range." This discount highlights the inherent differences between primary funding rounds, where strategic investors might pay a premium for access and influence, and the secondary market, which is more sensitive to immediate liquidity, perceived risk, and market sentiment.
OpenAI itself has actively sought to exert greater control over secondary trading of its shares. An OpenAI spokesperson reportedly advised caution regarding "any firm that purports to have access to OpenAI equity, including through an SPV," emphasizing the company’s establishment of authorized, fee-free channels through traditional banks. This move aims to counter what OpenAI described as a "high-fee broker model" prevalent in the less regulated secondary market, seeking to provide a more structured and potentially more equitable avenue for shareholders to divest.
Perhaps tellingly, and indicative of the shifting market dynamics, prominent financial institutions like Morgan Stanley and Goldman Sachs have begun offering OpenAI shares to their high-net-worth clients without charging customary carry fees. This move suggests an effort to facilitate trading and maintain investor interest, potentially in response to OpenAI’s expressed desire for more controlled secondary markets. In stark contrast, Goldman Sachs continues to charge its standard carry — typically ranging from 15% to 20% of profits — for clients seeking exposure to Anthropic, underscoring the premium associated with Anthropic’s highly sought-after shares. This differential pricing strategy by major banks provides a clear, tangible illustration of the divergent investor sentiment towards the two AI powerhouses.
SpaceX: The Unwavering Giant and Impending Market Catalyst
Standing apart from the fluctuating sentiments surrounding the AI contenders is SpaceX, Elon Musk’s rocket and satellite behemoth. Anderson characterizes SpaceX as a unique entity within Rainmaker’s extensive universe, one that largely evaded the punishing market correction that impacted much of the private sector between 2022 and 2024. During this period, many private companies witnessed their shares plummet by 60% to 70% from their peak valuations, often after experiencing equally rapid surges. SpaceX, however, "has been pretty much consistently up and to the right," Anderson noted, a testament to its consistent operational achievements, ambitious long-term vision, and disciplined financial management.
Anderson, while naturally having an economic interest in flattering the company and its early backers, credits SpaceX’s management with a shrewd and disciplined approach to pricing its shares. Unlike many companies that succumb to the temptation to maximize the valuation of every funding round or tender offer, SpaceX deliberately left "room for error." "A lot of companies will fall for the temptation to maximize the price of their stock in every round," he observed. "The problem is that that doesn’t leave any room for error."
By contrast, SpaceX "played it conservatively" by "not getting too greedy," a strategy that has yielded enormous payoffs for its earlier investors. The foresight of this approach is underscored by its historical valuation trajectory. In 2015, when Google and Fidelity jointly invested $1 billion, SpaceX was valued at approximately $12 billion. An investor who secured shares at that valuation is now sitting on a gain of more than 100x, with the company currently valued at over $1 trillion in anticipation of its public debut. This extraordinary return illustrates the power of long-term vision combined with strategic capital management.
The Imminent IPO Race: A Zero-Sum Game for Liquidity
The long-anticipated public offering of SpaceX now appears imminent. The company confidentially filed this week for an initial public offering, setting the stage for what could be one of the largest market debuts in history. Reports suggest Elon Musk aims to raise between $50 billion and $75 billion, potentially as early as June. Such a colossal listing would rival only Saudi Aramco’s 2019 debut, which valued the energy giant at $1.7 trillion.
Unsurprisingly, the rumored filing has already dramatically altered the dynamics of the secondary market for SpaceX shares. "Today, I saw a flood of SpaceX investors coming to me saying, ‘Can you give me SpaceX?’" Anderson recounted, highlighting a sudden surge in buy-side activity. However, this demand is quickly outpacing supply. As a company draws closer to its IPO, existing shareholders typically have less incentive to sell their private shares, preferring to wait for the liquidity event and potential upside of the public market. This natural drying up of supply amplifies the urgency for late-stage investors to gain exposure.
This impending IPO has broader implications, particularly for OpenAI and Anthropic, both of which are reportedly exploring public offerings of their own and have signaled potential moves this year. Anderson suggests that SpaceX, by being the first to file, is poised to test the market’s appetite in a major way, potentially disadvantaging those who follow. "SpaceX is going to soak up a lot of liquidity," he stated flatly. "There’s only so much money out there allocated to IPOs."
This "first-mover advantage" in the IPO market is a critical dynamic. The initial company to go public within a specific sector or during a particular market cycle often captures the lion’s share of available institutional and retail capital. Subsequent entrants, while still potentially attractive, may face increased scrutiny, a more saturated investor base, and, crucially, less capital available for allocation. This scenario plays out across various industry verticals, and despite the intense attention currently showered on AI companies, they are not entirely immune to these market forces. Timing an IPO too early carries the risk of being the sole tester of market receptivity, while waiting for others to go first might mean finding that the biggest checks have already been written.
Broader Market Implications and Future Outlook
The unfolding narrative of Anthropic, OpenAI, and SpaceX underscores the evolving maturity and complexity of the private secondary market. It highlights the power of narrative, the impact of strategic corporate decisions, and the enduring allure of transformative technologies. The divergent investor sentiments toward Anthropic and OpenAI, juxtaposed with SpaceX’s consistent ascent, paint a nuanced picture of an investment landscape driven by both fundamental performance and perceived market positioning.
As the tech IPO window tentatively reopens, SpaceX’s monumental listing will serve as a bellwether. Its success or challenges will undoubtedly influence the timing and reception of other high-profile tech debuts, particularly those in the highly anticipated AI sector. The battle for investor capital and market attention will intensify, making strategic timing and a compelling value proposition more critical than ever for companies contemplating the leap to the public markets. The insights gleaned from the secondary market, with its immediate reflection of investor demand and sentiment, offer a crucial prelude to these much-anticipated public market spectacles.
Further insights from this interview with Glen Anderson are available in the upcoming episode of the StrictlyVC Download podcast, which releases every Tuesday. Recent episodes have featured discussions with Whoop CEO Will Ahmed and investor Bill Gurley.
