Glen Anderson has been brokering deals in private equity since 2010, when the number of institutional investors focused on the late private market could be counted on two hands. Today, he says, there are thousands.
As president of investment bank Rainmaker Securities, whose focus includes private equity markets — it facilitates transactions in about 1,000 stocks — Anderson has a front-row seat to one of the most nail-biting moments in secondary market history. And right now, he suggests, the narrative has three protagonists: Anthropic, OpenAI and SpaceX.
But the story is more complicated than the headlines suggest.
Anderson’s reading on Anthropic is consistent with what Bloomberg reported earlier this week: Demand for the company’s stock has become nearly insatiable. Bloomberg quoted Ken Smythe, founder and CEO of Next Round Capital, as saying that buyers had indicated to his outfit that they had $2 billion in cash ready to deploy in Anthropic, although about $600 million in OpenAI shares that investors are trying to sell have not found takers.
Anderson sees something similar at Rainmaker. “The hardest stock to pick up on our marketplace is Anthropic,” he told TechCrunch yesterday afternoon from his home in Miami. “There are just no sellers.”
Part of what turbocharged that demand, Anderson argues, was Anthropic’s very public battle with the Department of Defense—an event that initially seemed like bad news for the company, but ended up being a godsend.
“The app became more popular, people rallied around the company as a sort of hero, taking on big government,” he said. “I think it reinforced the story and made it even more differentiated from OpenAI.”
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This distinction is becoming increasingly meaningful to investors navigating a market where the prevailing logic for years was to bet on everyone. Anderson notes 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 — but momentum, at least in the secondary market, has shifted.
This does not mean that OpenAI has fallen off a cliff. Anderson pushes back a bit on a binary reading of the situation.
“I wouldn’t say it’s an one-or-the-other conversation,” he said.
But the tension is not there. “It’s not nearly as vibrant a market as Anthropic right now,” he acknowledged.
In terms of valuation, Anderson broadly confirmed Bloomberg’s reporting that OpenAI shares in the secondary market are trading as if the company were valued at $765 billion — a noticeable discount from the company’s most recent primary round valuation of $852 billion. 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 wary of any company that purports to have access to OpenAI shares, including through an SPV,” an OpenAI spokesperson told Bloomberg, noting that the company had established authorized channels through banks, without fees, to counter what it described as a high-fee brokerage 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 carrying fees, according to Bloomberg. Goldman, meanwhile, charges its usual carry — often 15% to 20% of profits — to clients seeking anthropic exposure.
What none of this accounts for is SpaceX, which stands out amid shifting sentiment around these other strong 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 driven up just as quickly).
The rocket and satellite giant has “been pretty consistently up and to the right,” Anderson said.
Anderson, who obviously has a financial 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.
“Many companies will succumb to the temptation to maximize the price of their shares in each round,” he said. “The problem is that it leaves no room for error.”
SpaceX, on the other hand, played it conservative by “not getting too greedy,” and the payoff for early investors has been huge. “You can imagine if someone came into 2015 what kind of gain they’re sitting on right now,” 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 got in at that price is now sitting on a gain of more than 100x, valuing the company at more than $1 trillion ahead of the planned IPO.
That IPO is now imminent, apparently. SpaceX filed confidentially this week for an initial public offering, setting the stage for what could be one of the biggest market debuts in history, with Elon Musk reportedly aiming to raise between $50 billion and $75 billion, possibly by June. Only Saudi Aramco’s 2019 debut, which valued the energy giant at $1.7 trillion, has come close.
Not surprisingly, 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 and saying, ‘Can you give me SpaceX?'” he noted. “It’s been a very active buying side.” But the 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.
This is where things get a little more difficult for OpenAI and Anthropic. Both companies are reportedly exploring their own public offerings and have signaled they could move this year. But SpaceX, by filing first, is testing the market’s appetite in a bigger way, and Anderson suggested that whoever follows will be at a disadvantage.
“SpaceX is going to soak up a lot of cash,” he said flatly. “There’s only so much money out there that’s allocated to IPOs.” 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 one that AI companies aren’t entirely immune to, despite the attention showered on them right now. Time your IPO too soon and you are the one testing the market’s receptivity. Wait for someone else to go first and you may find that the biggest checks have already been written.
You can hear more of our interview with Anderson on the upcoming episode of the StrictlyVC Download podcast, released every Tuesday. In the meantime, watch the latest episodes, including those with Whoop CEO Will Ahmed and investor Bill Gurley.