Glen Anderson has been a prominent figure in brokering private company shares since 2010. At that time, institutional investors focused on the late-stage private market were few, a number he now estimates to be in the thousands, reflecting significant market expansion.
As president of Rainmaker Securities, an investment bank exclusively dedicated to private securities markets and facilitating transactions for approximately 1,000 stocks, Anderson possesses an unparalleled view of a monumental period in the secondary market's history. He identifies three key players currently dominating this narrative: Anthropic, OpenAI, and SpaceX.
His core insight is that the underlying market dynamics are considerably more intricate than commonly portrayed in headlines.
Anderson's assessment of Anthropic aligns with recent Bloomberg reports, indicating an almost insatiable demand for the company's shares. Bloomberg cited Ken Smythe, founder and CEO of Next Round Capital, who revealed that buyers had expressed readiness to deploy $2 billion in cash into Anthropic. This contrasts sharply with the approximate $600 million worth of OpenAI shares that investors are struggling to sell.
Rainmaker Securities is witnessing a similar trend. Anderson remarked to TechCrunch yesterday, "The hardest stock to source in our marketplace is Anthropic. There's just no sellers."
Anderson posits that a significant driver behind this escalated demand was Anthropic's highly publicized dispute with the Department of Defense. What initially appeared to be a setback for the company ultimately transformed into an unexpected advantage.
"The app got more popular, people rallied around the company as kind of a hero, taking on big government," he explained. "I think it amplified the story and made it even more differentiated from OpenAI."
This differentiation is gaining increasing importance for investors operating in a market that, for years, favored broad bets across multiple players. While Anderson acknowledges that many institutional investors still desire exposure to both Anthropic and OpenAI, stating "The jury’s still out" on which AI model will ultimately prevail, the momentum in the secondary market has distinctly shifted.
This shift does not imply a collapse for OpenAI. Anderson advises against a simplistic, binary interpretation of the current market landscape.
"I wouldn’t say it’s a one-or-the-other conversation," he clarified.
However, the palpable excitement is missing. Anderson conceded, "It’s not nearly as vibrant a market as Anthropic right now."
Regarding valuation, Anderson generally corroborated Bloomberg's report that OpenAI shares are trading on the secondary market at a valuation implying $765 billion for the company. This represents a noticeable discount compared to its recent primary-round valuation of $852 billion. While operating from memory, Anderson stated the Bloomberg figure was "in the right range."
OpenAI itself has actively sought to exert greater control over secondary trading. An OpenAI spokesperson informed Bloomberg that "People should be extremely cautious of any firm that purports to have access to OpenAI equity, including through an SPV," emphasizing that the company has established authorized, fee-free channels through banks to counteract what it described as a high-fee broker model.
Notably, banks such as Morgan Stanley and Goldman Sachs have reportedly begun offering OpenAI shares to their high-net-worth clients without charging carry fees, according to Bloomberg. Conversely, Goldman Sachs is applying its standard carry fees—typically 15% to 20% of profits—for clients seeking exposure to Anthropic.
Standing apart from the fluctuating sentiments around these powerful AI brands is SpaceX. Anderson characterizes it as one of the rare entities within Rainmaker's purview that entirely avoided the severe market correction that impacted much of the private market between 2022 and 2024, a period where many private companies saw their share values plummet by 60% to 70% from their peaks following rapid prior appreciation.
The aerospace and satellite giant has "been pretty much consistently up and to the right," Anderson noted.
Anderson, who naturally has a vested interest in promoting the company and its early investors, attributes SpaceX's sustained success to its management's disciplined pricing strategy, refraining from maximizing every last dollar in each funding round or tender offer.
"A lot of companies will fall for the temptation to maximize the price of their stock in every round," he stated. "The problem is that that doesn't leave any room for error."
In contrast, SpaceX adopted a conservative approach, "not getting too greedy," which has resulted in extraordinary returns for early investors. Anderson remarked, "You can imagine if someone got in in 2015 what kind of gain they’re sitting on right now."
To elaborate: SpaceX was valued at approximately $12 billion in 2015 when Google and Fidelity jointly invested $1 billion. An investor entering at that valuation would now be realizing a gain exceeding 100x, as the company is valued at over $1 trillion in anticipation of its planned IPO.
That IPO now appears imminent. SpaceX confidentially filed this week for an initial public offering, paving the way for what could be one of the largest market debuts ever. Elon Musk is reportedly aiming to raise between $50 billion and $75 billion, potentially by June. Only Saudi Aramco's 2019 debut, which valued the energy giant at $1.7 trillion, comes close in scale.
Unsurprisingly, this rumored filing has already altered the dynamics of the secondary market for SpaceX shares, according to Anderson.
"Today, I saw a flood of SpaceX investors coming to me saying, 'Can you give me SpaceX?'" he observed. "It's been a very active buy side." However, supply is dwindling. As a company approaches an IPO, existing shareholders have less incentive to sell, anticipating the impending liquidity event.
This scenario presents a more challenging outlook for OpenAI and Anthropic. Both companies are reportedly exploring their own public offerings and have indicated potential moves this year. Yet, by filing first, SpaceX is poised to significantly test the market's appetite. Anderson suggests that any company following will face a disadvantage.
"SpaceX is going to soak up a lot of liquidity," he stated plainly. "There’s only so much money out there allocated to IPOs." The first mover secures the available capital; subsequent entrants will likely encounter increased scrutiny and potentially fewer investment funds.
This dynamic is common across various industry sectors, and even the highly-regarded AI companies are not entirely immune, despite the current attention they receive. Launching an IPO too early means you become the one testing market receptivity. Waiting for another to go first, however, might mean the largest investment checks have already been committed.
Further insights from our interview with Anderson will be available in the upcoming episode of the StrictlyVC Download podcast, released every Tuesday. In the interim, explore recent episodes featuring Whoop CEO Will Ahmed and investor Bill Gurley.
The Editorial Staff at AIChief is a team of professional content writers with extensive experience in AI and marketing. Founded in 2025, AIChief has quickly grown into the largest free AI resource hub in the industry.