Glenn Anderson has been brokering private company stocks since 2010, at a time when institutional investors focused on the late-stage private market, which could be done with two hands. Today, they say, there are thousands.

As president of investment bank Rainmaker Securities, which focuses on private securities markets — it facilitates transactions in about 1,000 stocks — Anderson has had a front-row seat to one of the most nail-biting moments in secondary market history. And right now, he suggests, there are three main players in the narrative: Anthropic, OpenAI, and SpaceX.

But the story is more complicated than the headlines suggest.

Anderson’s reading on Anthropic is according to Bloomberg. Reported Earlier this week: Demand for the company’s shares has become nearly insatiable. Bloomberg quoted Next Round Capital founder and CEO Ken Smith as saying that buyers had indicated to his organization that they had $2 billion in cash ready to deploy to Anthropic, even as the roughly $600 million in OpenAI shares that investors are trying to sell have not found takers.

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

Part of the demand, Anderson says, was Anthropic’s public standoff with the Department of Defense — a turn of events that initially seemed like bad news for the company but has turned out to be a gift.

“The app became more popular, people rallied around the company as a hero, taking on big government,” he said. “I think it expanded the story and made it even more different from OpenAI.”

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

This does not mean that OpenAI has fallen off a cliff. Anderson pushes back a bit on the binary reading of the situation.

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

But Josh is not there. “It’s not as dynamic a market as Anthropic right now,” he acknowledged.

On the valuation, Andersen largely confirmed Bloomberg’s reporting that OpenAI’s shares in the secondary market are trading as if the company is worth $765 billion — a significant discount to the company’s new $852 billion primary round valuation. He cautioned that he was working from memory, but said Bloomberg’s personality was “right on the mark.”

OpenAI itself has sought to gain more control over secondary trading. “People should be extremely wary of any firm that intends to access OpenAI equity, including an SPV,” an OpenAI spokesperson told Bloomberg, adding that the company has established channels authorized through banks, without fees, to counter what it described as a high-fee broker model.

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

None of this is SpaceX, which stands out amid the shifting sentiment surrounding these other powerful brands. Anderson describes him as one of the only names in the Rainmaker’s Universe that never experienced the correction that punished much of the private market between 2022 and 2024, a period when shares of many private companies fell 60% to 70% from their peaks (while their prices rose just as quickly).

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

Anderson, who naturally has an economic interest in flattering the company and its former backers, credits SpaceX’s management with disciplined pricing and not squeezing every last dollar out of every funding round or tender offer.

“A lot of companies will be tempted to maximize their stock price every cycle,” he said. “The problem is that it leaves no room for error.”

SpaceX, by contrast, paid it conservatively, “not being too greedy,” and the payoff for earlier investors has been huge. “You can imagine what kind of leverage someone is getting right now if they get into 2015,” Anderson said.

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

That IPO is now imminent, apparently. SpaceX secretly filed for an initial public offering this week, setting the stage for what could be the biggest market debut in history, with Elon Musk reportedly aiming to raise between $50 billion and $75 billion 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 secondary market dynamics 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 buying side.” But supplies are drying up. The closer a company gets to an IPO, the less incentive existing shareholders have as they can see a liquidity event on the horizon.

This is where things get a little bumpy for OpenAI and Anthropic. Both companies are reportedly exploring their own public offerings and have indicated they could move this year. But SpaceX, by filing first, is about to test market appetite in a big way, and Anderson suggests that whoever follows will be at a disadvantage.

“SpaceX is going to take a lot of liquidity,” he said bluntly. “There’s only so much money earmarked for IPOs.” The first mover goes into the trough first. Followers face more scrutiny and potentially less capital.

It’s a dynamic that plays out in every so-called vertical and one that AI companies aren’t entirely immune to, despite the attention they’re getting right now. Time your IPO too early and you’re testing market acceptance. Wait for someone else to leave first, and you may find that the biggest checks have already been written.

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