Glen Anderson has been brokering trades in private company shares since 2010, back when the number of institutional investors focused on the late-stage private market could be counted on two hands. Today, he says, there are thousands.

As president of the investment bank Rainmaker Securities, whose focus includes private securities markets — it facilitates transactions in roughly 1,000 stocks — Anderson has a front-row seat to one of the most nail-biting moments in the history of the secondary market. And right now, he suggests, the narrative has three main characters: Anthropic, OpenAI, and SpaceX.

But the storyline is more complicated than the headlines suggest.

Anderson’s read on Anthropic is consistent with what Bloomberg reported earlier this week: demand for the company’s shares has become almost insatiable. Bloomberg quoted Ken Smythe, founder and CEO of Next Round Capital, saying that buyers had indicated to his outfit that they had $2 billion of cash ready to deploy into Anthropic, even as roughly $600 million in OpenAI shares that investors are trying to sell haven’t found takers.

Anderson sees something similar at Rainmaker. “The hardest stock to source in our marketplace is Anthropic,” he told TechCrunch yesterday afternoon from his Miami home. “There’s just no sellers.”

Part of what turbocharged that demand, Anderson argues, was Anthropic’s very public standoff with the Department of Defense — a turn of events that initially seemed like bad news for the company but has wound up becoming a gift.

“The app got more popular, people rallied around the company as kind of a hero, taking on big government,” he said. “I think it amplified the story and made it even more differentiated from OpenAI.”

That distinction is becoming increasingly meaningful to investors navigating a market where, for years, the prevailing logic was to bet on everyone. Anderson notes that many institutional investors still want exposure to both Anthropic and OpenAI. “The jury’s still out,” he said, on which AI model will ultimately win – but the momentum, at least in the secondary market, has shifted.

That doesn’t mean OpenAI has fallen off a cliff. Anderson pushes back slightly on a binary reading of the situation.

“I wouldn’t say it’s a one-or-the-other conversation,” he said.

But the excitement isn’t there. “It’s not nearly as vibrant a market as Anthropic right now,” he acknowledged.

On valuation, Anderson broadly confirmed Bloomberg’s reporting that OpenAI shares on the secondary market are trading as if the company were valued at $765 billion — an appreciable discount to the company’s newest $852 billion primary-round valuation. He cautioned that he was working from memory, but said the Bloomberg figure was “in the right range.”

OpenAI itself has tried to assert more control over secondary trading. “People should be extremely cautious of any firm that purports to have access to OpenAI equity, including through an SPV,” an OpenAI spokesperson told Bloomberg, noting the company had established authorized channels through banks, with no fees, to counter what it described as a high-fee broker model.

Perhaps tellingly — at least for now — banks including Morgan Stanley and Goldman Sachs have begun offering OpenAI shares to their high-net-worth clients without charging carry fees, according to Bloomberg. Goldman, meanwhile, is charging its customary carry – often 15% to 20% of profits – for clients seeking Anthropic exposure.

What none of this accounts for is SpaceX, which stands apart amid shifting sentiment around these other powerful brands. Anderson describes it as one of the only names in Rainmaker’s universe that never experienced the punishing correction that hit much of the private market between 2022 and 2024, a period when many private companies’ shares fell 60% to 70% from their peaks (after their valuations were run up just as fast).

The rocket and satellite behemoth has “been pretty much consistently up and to the right,” Anderson said.

Anderson, who, naturally, has an economic interest in flattering the company and its earlier backers, credits SpaceX’s management with disciplined pricing and not squeezing every last dollar out of 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 said. “The problem is that that doesn’t leave any room for error.”

SpaceX, by contrast, played it conservatively, by “not getting too greedy,” and the payoff for earlier investors has been enormous. “You can imagine if someone got in in 2015 what kind of gain they’re sitting on right now,” said Anderson.

To put a finer point on that comment: SpaceX was valued at roughly $12 billion in 2015, when Google and Fidelity jointly invested $1 billion in the company. Someone who got in at that price is now sitting on a gain of more than 100x, with the company valued at more than $1 trillion ahead of its planned IPO.

That IPO is now imminent, seemingly. SpaceX filed confidentially this week for an initial public offering, setting the stage for what could be one of the largest market debuts in history, with Elon Musk reportedly aiming to raise between $50 billion and $75 billion, possibly in June. Only Saudi Aramco’s 2019 debut, which valued the energy giant at $1.7 trillion, has come close.

Unsurprisingly, the rumored filing has already changed 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 noted. “It’s been a very active buy side.” But supply is drying up. The closer a company gets to an IPO, the less incentive existing shareholders have to sell because they can see the liquidity event on the horizon.

That’s where things get a little dicier for OpenAI and Anthropic. Both companies are reportedly exploring public offerings of their own and have signaled they could move this year. But SpaceX, by filing first, is about to test the market’s appetite in a major way, and Anderson suggested that whoever follows will be at a disadvantage.

“SpaceX is going to soak up a lot of liquidity,” he said flatly. “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 in every so-called vertical and from which the AI companies aren’t completely immune, despite the attention being showered on them right now. 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.

You can hear more of our interview with Anderson in the upcoming episode of the StrictlyVC Download podcast, which drops every Tuesday. In the meantime, check out recent episodes, including those with Whoop CEO Will Ahmed and investor Bill Gurley.