Glen Anderson has been brokering trades in private equity since 2010, when the number of institutional investors focusing on late-stage private equity could be counted on two hands. Today, he says, there are thousands.
As chairman of investment bank Rainmaker Securities, which focuses exclusively on private equity markets and facilitates trades in about 1,000 stocks, Anderson has a front-row seat to one of the most tragic moments in the history of the secondary market. And right now, he suggests, the narrative has three main characters: Anthropic, OpenAI and SpaceX.
The result: the story is more complicated than the titles suggest.
Anderson’s reading of Anthropic is consistent with Bloomberg’s was mentioned earlier this week: demand for the company’s stock has become nearly insatiable. Bloomberg cited Ken Smythe, founder and CEO of Next Round Capital, as saying that the buyers had indicated to his outfit that they had $2 billion in cash ready to use on Anthropic, even as some $600 million in OpenAI shares that investors are trying to sell have not found buyers.
Anderson sees something similar in Rainmaker. “The most difficult stock in our market is Anthropic,” he told TechCrunch yesterday afternoon from his home in Miami. “There are just no sellers.”
Part of what paid for that demand, Anderson argues, was Anthropic’s very public confrontation with the Department of Defense—a turn of events that initially seemed like bad news for the company, but ended up being a gift.
“The app became more popular, people rallied around the company as a hero, taking on big government,” he said. “I think it enhanced the story and made it even more diverse than OpenAI.”
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This distinction is becoming increasingly important for 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 is still out,” he said, on which AI model will ultimately win — but the dynamic, at least in the secondary market, has changed.
This is not to say that OpenAI fell off a cliff. Anderson pushes back slightly on a binary reading of the situation.
“I wouldn’t say it’s an one-way conversation,” he said.
But the excitement is not there. “It’s not nearly as vibrant a market as Anthropic right now,” he acknowledged.
As for the valuation, Anderson broadly confirmed Bloomberg’s report that OpenAI’s shares in the secondary market are trading as if they were valued at $765 billion — a marked discount to the company’s most recent $852 billion valuation in a seed round. He cautioned that he was working from memory, but said Bloomberg’s number was “in the right range.”
OpenAI itself has tried to assert more control over secondary transactions. “People should be extremely wary of any company that claims to have access to OpenAI shares, including through SPVs,” an OpenAI spokesperson told Bloomberg, noting that the company had set up authorized channels through banks, commission-free, to counter what it described as a high-commission 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 transfer fees, according to Bloomberg. Goldman, meanwhile, charges its usual fee—often 15% to 20% of profits—for clients seeking exposure to Anthropic.
What’s not due to any of this is SpaceX, which stands out amid shifting sentiment around these other powerhouse brands. Anderson describes it as one of the only names in the Rainmaker universe that never experienced the punitive correction that hit much of the private market between 2022 and 2024, a period in which shares of many private companies fell 60% to 70% from their highs (after their valuations did just as quickly).
The missile and satellite behemoth “was almost steadily up and to the right,” Anderson said.
Anderson, who, of course, has a financial interest in flattering the company and its past backers, credits SpaceX management with disciplined pricing and not squeezing every last dollar out of every funding round or offering.
“Many companies will be tempted to maximize their share price in each round,” he said. “The problem is that this leaves no room for error.”
SpaceX, by contrast, played it safe, “didn’t get too greedy,” and the payoff for early investors was huge. “You can imagine if someone went into 2015 what kind of profit they’re sitting on right now,” Anderson said.
To put a better perspective on this 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 at more than 100x earnings, with the company valued at more than $1 trillion ahead of its planned IPO.
That IPO is now imminent, apparently. SpaceX filed confidentially this week for an initial public offering, setting the stage for one of the biggest 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, came close.
Not surprisingly, 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?’ noted. “It was a very active buy side.” But the offer is running out. 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 tighter for OpenAI and Anthropic. Both companies are reportedly exploring their own public offerings and have signaled they could move forward this year. But SpaceX, by filing first, is about to test market appetite in a big way, and Anderson suggested that whoever follows will be at a disadvantage.
“SpaceX is going to absorb a lot of liquidity,” he said flatly. “There’s only so much money out there that goes into IPOs.” The first mover reaches 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 industry, and one that AI companies aren’t entirely immune to, despite the attention they’re currently receiving. Time your IPO too early and you’re the one testing market 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 in his upcoming episode Download StrictlyVC podcast, which drops every Tuesday. In the meantime, check out recent episodes, including those with Whoop CEO Will Ahmed and investor Bill Gurley.
