The Round Is the New IPO

The IPO window spent September doing its best impression of a revolving door. On September 12, Sam Altman told Fortune there would be no OpenAI listing this year. A week later, The Wall Street Journal reported Anthropic had slid from October to November. If you were waiting for the opening bell to tell you what these companies are worth, pull up a chair.

The private market stopped waiting for the bell and started ringing its own, roughly every four months.

OpenAI is the cleanest example. Three days after declining the public market, it had investors float a round at $1.2 trillion against March's $852 billion. No formal talks, per CNBC, and some of it was pitched as a way for employees to sell. That is the tell. The round is doing the IPO's job: price discovery, employee liquidity and a fresh mark for every LP's book, delivered in a term sheet on a calendar the company controls.

Elana Gold, who writes The Cap Table, put a name on it this month: the funding cycle is compressing, with valuations resetting every four to five months. Her headline example is Cognition, $26 billion to $48 billion in four months. I would add one line. When the anchor moves that often, "discount to last round" has a shelf life shorter than most investment committee calendars.

Everyone I talk to says demand is up, and prices with it. At the front of the line, that is right. Caplight has OpenAI up 4.2% over 30 days, trading 3.3% above the March round on about $610 million of volume. Carta reports tender value on its platform up 200% in the first half, a four-year high.

Step one row back and the heat fades. Forge has the median secondary trade slipping from par in June to a 7% discount in July, with buy-side interest falling from 57% of indications to 48%. The back of the line is being repriced by acquirers: Miro went to Bending Spoons at about $1.8 billion of equity value, against a $17.5 billion peak.

So the distinction for this issue: the market is not hot. The front of the line is, and it is pricing the next round rather than the last one. Run OpenAI that way. A 3.3% premium to March looks rich. Against the $1.2 trillion investors floated, the same trade is roughly a 27% discount, if that round ever prices near the number.

Now the names, and my read on each. Some of this is reported. Some of it is what I am hearing. I will tell you which is which.

Stripe. Nothing announced. But the rumblings I am hearing from the back end of the street say a round or tender is coming, and I believe them. My rule of thumb, and it has held up well: when demand for a name picks up with no news attached, there is usually a round, a tender or something like it being built behind the scenes. Forge had Stripe at $72.45 a share in early September, about 16% over February's $62.47 tender price, on no announcement at all. Stripe has run a tender or buyback at least once a year, $159 billion being the latest, and with no IPO on the calendar the bid is behaving like it knows the next one is close. Add a $53 billion offer for PayPal that came and went this summer, and you have a company that is clearly thinking about what its own stock is worth.

Legora. The most interesting print of the month, and not because it is the biggest. Legora extended its Series D in April at $5.6 billion, with Nvidia's venture arm and Atlassian coming in, and was reportedly out looking for more than $10 billion in August. Five weeks later, Bloomberg had it talking about $300 million at roughly $8.5 billion pre-money. That is still a 50% step-up in six months. It is also the market declining the first ask, which is what a functioning market is supposed to do. Harvey, its closest competitor, closed this month at $15.5 billion. The gap between the two is now close to 2x, and legal AI buyers will spend the next year arguing about whether it deserves to be.

Thinking Machines. A $12 billion seed round in July 2025, now reportedly in talks at $40 billion or more with Accel leading and Nvidia discussing a piece. The price is a bet on the team and the roadmap more than on revenue, which makes it the hardest mark on this list to underwrite.

Full disclosure, since you will ask: Prince Capital has access to both Legora and Thinking Machines, through a GP we work with directly. That is also why everything I have cited on these two is public reporting and not our terms. If either one is on your list, reach out.

Ramp. $32 billion last November, $44 billion in June, early talks around $60 billion in September. Three marks in ten months. If you bought Ramp paper at a discount to the November round, congratulations: you bought it at a discount to a number that no longer exists.

Shield AI. $12.7 billion in March, reportedly talking at $20 billion or more now. At midyear, 92% of defense tech order flow on Nasdaq Private Market sat on the buy side.

Erebor. The bank opened in February on a $4.35 billion mark and was reported this summer in talks at $8 billion to $9.5 billion. From what I am hearing, it is back at the table. A regulated bank doubling in six months is not a sentence I expected to write in 2026. We will have access to this round as well, so if Erebor is on your list, let us know.

Databricks. The reference point for all of it: asked for $1 billion in August, was shown $15 billion, took $5 billion at $190 billion. Every founder on this list has that number taped to the wall, and the Fed's first hike since 2023 on September 16 did not appear to loosen the tape.

What to do with this. If you screen on discount to last round, add two columns: the date of that round, and what has been reported since. A premium to a stale round can be a discount to the next one. A deep discount to a stale round can be the market telling you the next round is not coming. And treat the IPO date as a variable: anything underwritten to a 2026 print for the big AI names needs a 2027 case at a 4% policy rate.

So tell me: which name are you being shown above its last round, and by how much? And if you are hearing what I am hearing on Stripe, I want to compare notes. Reply at info@theprincecg.com or message me on LinkedIn.

Prince Capital prices this queue weekly across our secondaries practice. If you are sizing an entry against a round that has not been announced yet, or holding stale paper that needs a real bid, we welcome the conversation. Reach out at info@theprincecg.com.

Prince Capital is a family office private investment firm. Views expressed are the author's own and include market commentary that has not been independently confirmed. Prince Capital may hold or arrange positions in companies discussed. This material is for informational purposes only and does not constitute an offer to sell or a solicitation to buy any security.