Glen Anderson has watched the private Technology markets evolve for 16 years. When he started brokering trades in private company shares back in 2010, institutional investors focused on late-stage private companies could literally be counted on two hands. Today, there are thousands. As president of Rainmaker Securities, an investment bank facilitating roughly 1,000 private stock transactions, Anderson has one of the best views in the room right now. And what he’s seeing in the secondary market is telling a story that’s far more complicated than the AI hype might suggest.
According to Bloomberg reporting, the narrative centers on three main characters: Anthropic, OpenAI, and SpaceX. But the dynamics between them have shifted in ways that reveal something deeper about how investors are starting to think about AI’s future.
Anthropic’s Moment
Demand for Anthropic shares has become almost insatiable. Bloomberg quoted Next Round Capital founder and CEO Ken Smythe saying that buyers had indicated they had $2 billion ready to deploy into Anthropic, even as roughly $600 million in OpenAI shares sit unwanted on the shelf. Anderson’s experience at Rainmaker mirrors this exactly. “The hardest stock to source in our marketplace is Anthropic,” he told TechCrunch. “There’s just no sellers.”
What turbocharged this demand might surprise you. Part of it traces back to Anthropic’s public standoff with the Department of Defense. What initially looked like a PR nightmare actually became a gift. Anderson’s analysis is sharp here: “The app got more popular, people rallied around the company as kind of a hero, taking on big government. I think it amplified the story and made it even more differentiated from OpenAI.”
That differentiation matters more than ever in a market where the prevailing logic for years was simply to bet on everyone. Many institutional investors still want exposure to both companies, but the momentum has clearly shifted. Anderson doesn’t sugarcoat it: the secondary market for OpenAI isn’t “nearly as vibrant” as Anthropic’s right now.
OpenAI’s Reality Check
This isn’t to say OpenAI has fallen off a cliff. Anderson pushes back against binary framing. “I wouldn’t say it’s a one-or-the-other conversation,” he said. But excitement has visibly cooled. According to Bloomberg reporting, OpenAI shares on the secondary market are trading as if the company were valued at $765 billion, a meaningful discount to its most recent $852 billion primary-round valuation.
OpenAI has tried to reassert control over secondary trading, with the company telling Bloomberg that investors should be “extremely cautious of any firm that purports to have access to OpenAI equity, including through an SPV.” The company established authorized channels through banks, offering shares without fees to counter high-fee broker models.
Yet Goldman Sachs is charging its customary carry, often 15% to 20% of profits, for clients seeking Anthropic exposure. For OpenAI, by contrast, Goldman and Morgan Stanley are offering shares to high-net-worth clients without charging carry fees. That’s a telling price war for a company that commanded absolute attention just months ago.
SpaceX Changes the Game
Then there’s SpaceX, which operates in an entirely different stratosphere. According to Anderson, it’s one of the only names in Rainmaker’s portfolio that never experienced the brutal correction that hit private markets between 2022 and 2024, when many companies saw shares fall 60% to 70% from their peaks. SpaceX has been “pretty much consistently up and to the right.”
Anderson credits the company’s management with disciplined pricing strategy. While many companies maximize their stock price in every funding round, SpaceX played it conservatively by “not getting too greedy.” The payoff has been staggering. Someone who got in at SpaceX’s 2015 valuation of roughly $12 billion is now sitting on a gain of more than 100x, with the company now valued at more than $1 trillion ahead of its planned IPO.
SpaceX filed confidentially for an IPO this week, setting the stage for what could be one of the largest market debuts in history. Elon Musk is reportedly aiming to raise between $50 billion and $75 billion, possibly in June. Only Saudi Aramco’s 2019 debut comes close in scale.
The IPO Sequencing Problem
This is where things get dicey for both AI companies. SpaceX’s filing has already changed secondary market dynamics. Anderson saw an immediate shift: “Today, I saw a flood of SpaceX investors coming to me saying, ‘Can you give me SpaceX?’ It’s been a very active buy side.” But supply is drying up. The closer a company gets to an IPO, the less incentive shareholders have to sell when liquidity is finally visible.
Anthropic and OpenAI are both reportedly exploring public offerings and signaling they could move this year. But SpaceX, by filing first, is about to test the market’s appetite in a major way. Anderson’s warning is blunt: “SpaceX is going to soak up a lot of liquidity. There’s only so much money out there allocated to IPOs.” The first mover gets to the trough first. Those who follow face both more scrutiny and potentially less capital.
It’s a dynamic that plays out across every sector and one from which even AI darlings aren’t immune, despite all the attention currently showered on them. Time your IPO too early and you’re the one testing market receptivity. Wait for someone else to go first, and you may find the biggest checks have already been written.
