Glen Anderson began facilitating trades in private company shares in 2010, a time when only a handful of institutional investors focused on the late-stage private market. He now observes there are thousands. As president of Rainmaker Securities, an investment bank specializing in private securities markets and handling transactions for about 1,000 stocks, Anderson has a prime view of a particularly tense and significant period for the secondary market. Currently, he points to three central players shaping the narrative: Anthropic, OpenAI, and SpaceX. The reality, he suggests, is more nuanced than simple headlines convey.

Anderson's assessment of Anthropic aligns with recent reports: demand for its shares has reached an extraordinary level. He notes that buyers have indicated having billions in capital ready to invest in Anthropic, while a substantial block of OpenAI shares seeking buyers has struggled to find takers. From his vantage point at Rainmaker, the issue is clear: "There’s just no sellers."

EMBED_PLACEHOLDER_0

Anderson believes one factor that supercharged this demand was Anthropic's very public disagreement with the Department of Defense. What initially appeared to be negative publicity ultimately benefited the company. "The app got more popular, people rallied around the company as kind of a hero, taking on big government," he said. This event, in his view, amplified Anthropic's story and helped distinguish it further from OpenAI.

This growing distinction is crucial for investors in a market where the previous strategy was often to invest broadly across the sector. Anderson notes that many institutional investors still seek exposure to both Anthropic and OpenAI, acknowledging that "the jury’s still out" on which AI model will ultimately prevail. However, the momentum in the secondary market has visibly shifted.

This shift does not imply OpenAI has collapsed. Anderson resists an oversimplified, binary reading of the situation, stating, "I wouldn’t say it’s a one-or-the-other conversation." Yet, he acknowledges the comparative lack of excitement, saying, "It’s not nearly as vibrant a market as Anthropic right now." On valuation, he broadly confirmed that OpenAI's secondary market shares are trading at a level implying a valuation around $765 billion, representing a noticeable discount to its latest primary-round valuation of $852 billion.

OpenAI has actively sought more control over secondary trading. A company spokesperson warned investors to be "extremely cautious" of firms claiming access to its equity, highlighting that the company has established authorized, no-fee channels through specific banks to counter a high-fee broker model. Notably, major banks have reportedly begun offering OpenAI shares to wealthy clients without charging certain fees, while maintaining their standard fees for clients seeking access to Anthropic shares.

Amid these shifting sentiments around AI giants, SpaceX occupies a unique position. Anderson describes it as one of the few major names that avoided the severe correction that impacted much of the private market between 2022 and 2024, a period when many companies saw share prices drop 60% to 70% from their peaks. The aerospace company's trajectory has "been pretty much consistently up and to the right," Anderson said.

Anderson, who has a professional interest in the company's success, credits SpaceX's management with disciplined pricing, avoiding the temptation to maximize valuation in every funding round. "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." In contrast, SpaceX played it conservatively by "not getting too greedy," which has resulted in enormous gains for early investors.

To illustrate, SpaceX was valued at roughly $12 billion in 2015 when Google and Fidelity invested. An investor from that era is now sitting on a gain exceeding 100 times their initial investment, with the company valued at over $1 trillion ahead of its planned IPO.

That IPO now appears imminent. SpaceX filed confidentially for an initial public offering this week, setting the stage for what could be one of the largest market debuts in history. The offering, reportedly aiming to raise between $50 billion and $75 billion, would be rivaled only by Saudi Aramco's 2019 debut.

Unsurprisingly, this filing has already altered the dynamics for SpaceX shares on the secondary market. "Today, I saw a flood of SpaceX investors coming to me saying, ‘Can you give me SpaceX,'" Anderson noted. "It’s been a very active buy side." However, the supply of shares is dwindling as shareholders, anticipating the near-term liquidity of the IPO, hold onto their stakes.

This creates a more challenging landscape for OpenAI and Anthropic, both of which are reportedly exploring their own public offerings this year. Anderson suggests that SpaceX, by filing first, will test the market's appetite in a major way and put later filers at a potential disadvantage. "SpaceX is going to soak up a lot of liquidity," he stated. "There’s only so much money out there allocated to IPOs." The first mover accesses capital first, while those who follow may face greater scrutiny and competition for remaining funds—a dynamic from which even high-profile AI companies are not immune.

You can hear more from our interview with Glen Anderson in the upcoming episode of the StrictlyVC Download podcast, released every Tuesday. In the meantime, explore recent episodes featuring guests like Whoop CEO Will Ahmed and investor Bill Gurley.