Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

Key takeaways

• OpenAI raised a staggering $122 billion round in February 2026 at an $852 billion valuation and about $694 per share, led by SoftBank, Nvidia, and Amazon, up 181% from its March 2025 round.
• Secondary units trade near $714.35, only about 3% above the last round price, up 165% over twelve months, at an $881 billion market cap.
• Run-rate revenue crossed $20 billion by the end of 2025, up 3x year over year. That puts the secondary at roughly 44x.
• Here is the surprise: on a revenue-multiple basis, OpenAI is cheaper than Anthropic, which trades near 70x on a smaller run rate.
• OpenAI does not allow direct stock transfers, so access is indirect only, through SPVs or forward purchase contracts, and the compute bill is enormous.

OpenAI is the company that put AI in front of everyone, and its numbers have gone somewhere frankly hard to comprehend. Revenue tripled year over year to more than $20 billion in run-rate by the end of 2025. The February 2026 round pulled in $122 billion, which is not a round so much as the GDP of a small country. And the secondary market has bid units up 165% in a year.

The interesting thing is not that OpenAI is expensive. It is that, measured against its closest rival, it might be the more reasonably priced of the two AI giants. That is a strange sentence to write about a company worth nearly $900 billion, so let's actually do the math and see if it holds up.

What the Numbers Actually Say

Entry price versus the last round. The February 2026 round priced at roughly $694 per share and an $852 billion valuation. Secondary units sit near $714.35, about 3% above that. That is one of the tightest premiums you will see, which tells you the secondary is trading essentially in line with where SoftBank, Nvidia, and Amazon just put in serious money. Worth noting: that round was itself a 181% jump from the $300 billion valuation just eleven months earlier. The repricing here has been violent, and you are stepping in right at the top of it.

Trailing multiple. The market cap is about $881 billion. OpenAI's run-rate revenue crossed $20 billion by the end of 2025, a figure its own CFO has confirmed, growing roughly 3x year over year. That works out to about 44x run-rate revenue. Rich, yes. But hold that number, because the comparison is the whole point. Our note on why the multiple you pay drives your return is the frame to keep in mind here.

Peer comparison. Anthropic, the other AI heavyweight accredited investors are weighing right now, trades near 70x on a $14 billion run rate. OpenAI has more revenue and a lower valuation, so it lands at a lower multiple. That inversion surprised me a little. The market is paying a bigger premium for Anthropic's growth rate and its scarcity on the secondary, while OpenAI, despite being the bigger business, gets the more grounded number. Neither is cheap against public software comps, which trade far below both. But relative to each other, OpenAI is the value play, if 44x can ever be called value.

Forward multiple. OpenAI projects revenue more than doubling to around $29 billion in 2026, then climbing toward $100 billion by 2027 or 2028 depending on whose projection you believe. On the 2026 figure, the forward multiple drops to about 30x. On the aggressive out-year numbers, today's price looks cheap. Those projections are the bull case, and they assume a market that keeps expanding at a pace no software category has sustained before.

Revenue trajectory and the compute problem. The top line is astonishing: $2 billion in 2023, $6 billion in 2024, over $20 billion in 2025. But here is the part that should keep you honest. OpenAI burned about $2.5 billion in cash in the first half of 2025 alone, and its losses are projected to triple toward $14 billion in 2026. Sam Altman has talked about roughly $1.4 trillion in data-center commitments over the next eight years. Read that number again. Even the company's own aggressive revenue projections do not obviously cover that kind of infrastructure bill, and OpenAI does not expect to turn a profit until around 2029. So you are buying the fastest revenue story in tech, strapped to one of the largest capital commitments in corporate history.

Profitability. There is none, and there is not projected to be for years. This is a growth-at-all-costs machine betting that scale and continued model leadership eventually justify the spend. That can work. It is also the single biggest risk in the story, and it is not priced like a risk at 44x.

The Demand Side

Notice reports demand outstripping supply by 1.5 to 1. Positive, but notably cooler than Anthropic's 2.9 to 1. The secondary has also been choppy, with units pulling back 13% in the first quarter of 2026 before recovering. So the enthusiasm is real but not frantic, and the price has shown it can wobble.

This is the supply-and-demand lens our very own Hustle Fund GP, Elizabeth Yin, brings to every valuation. As she puts it, price comes down to the supply of a tranche of shares against the demand from investors chasing it. A 1.5-to-1 ratio is healthy demand, not a stampede, which is part of why OpenAI trades at a tighter premium to its last round than Anthropic does. The lesson holds either way: underwrite the business, not the length of the line behind you, because that line can shorten fast.

The Moat Question

AI is the most hyped market on earth, so the fair question is whether OpenAI is genuinely differentiated or just the biggest name in a crowded field. The honest answer is that it has the largest consumer distribution in the category by a wide margin, hundreds of millions of weekly users, and a brand that became a verb. That is a real moat, and it separates OpenAI from the pack of companies that are mostly unicorns built on hype rather than durable advantage.

The bear case is that frontier model performance is converging, competitors are extremely well funded, and consumer attention is fickle. At 44x, with a $1.4 trillion infrastructure bet underneath it, you need the distribution advantage to translate into durable pricing power. That is the bet, plain and simple.

How You Would Actually Buy It (And Why That Matters)

OpenAI does not allow direct stock transfers. You cannot hold shares in your own name. Access runs through a vehicle, and the two common ones are special purpose vehicles and forward purchase contracts. Our SPV strategy guide covers how these pool capital into a single late-stage position. Two risks matter more than any other, and they get sharper in a name this large and this sought after.

Risk one: forward purchase contracts are synthetic exposure. A forward is not a share. It is a contract in which a current holder promises to deliver shares or their value to you later, usually at an exit. You are not on the cap table. You hold a promise. If the seller defaults, or OpenAI blocks the transfer, or the seller's own arrangement collapses, you become an unsecured creditor of a counterparty rather than an owner of the company. With no IPO date and a complicated corporate structure, that counterparty risk can sit unresolved for years. Know exactly who stands behind any forward before you commit.

Risk two: second and third-layer SPVs stack fees and hide your cost basis. In a name everyone wants, the vehicle you are offered is often not the one holding the stock. It is an SPV that bought into another SPV that holds a forward that references the shares. Every layer adds a management fee and carry, and every layer makes your true entry price murkier. On a company already at 44x, a couple of extra layers can quietly push your effective multiple higher without you seeing it. Ask how many layers separate your check from the actual shares and what each charges. Bring the same discipline you would to protective terms on any deal, and plan your exit and liquidity before you enter, because you may be holding a long time.

What Has to Go Right, and What Has to Go Wrong

Bull case: revenue keeps compounding toward the $100 billion projections, the distribution moat holds, the infrastructure spend eventually pays for itself, and OpenAI lists at a valuation that makes today's $881 billion look early. Given the trajectory, not impossible.

Bear case: growth slows from historic to merely great, the $1.4 trillion compute bill becomes an anchor, losses balloon as projected, the multiple compresses, and your 3% premium to a February round evaporates while the indirect structure clips your upside with fees. Very possible, and largely unpriced at 44x.

The honest read is that OpenAI is the more reasonably valued of the two AI titans, which is not the same as reasonably valued. It is a bet on the biggest brand in AI outrunning the biggest capital commitment in AI.

The Bottom Line

OpenAI is a genuinely historic company, and relative to Anthropic it is the cheaper way to own the AI frontier on the secondary. That relative value is real. It just sits on top of a spending commitment so large that even the bulls admit the revenue has to keep compounding at a historic pace to justify it. Entering at 44x, about 3% above a fresh mega-round, through an indirect structure that takes its cut, is a decision to make with clear eyes rather than a reflex.

This is exactly the kind of deal where a serious community earns its keep, because separating confirmed revenue from projections, and seeing the fee load buried in a stack of SPVs, is what gets missed in a frenzy. That is a big part of why Angel Squad exists. It is a community of more than 2,500 investors across 50-plus countries who have collectively put over $30 million into 70-plus startups, with a strict no-a-holes policy and access to the top 1% of deal flow. Hustle Fund is an early-stage fund, but Squad members see the full spectrum, from pre-seed through pre-IPO names of this caliber, with the context to actually vet the numbers and the structure before wiring. Learn more at hustlefund.vc/squad.

Frequently Asked Questions

What is OpenAI's current valuation? OpenAI was valued at $852 billion in its February 2026 round. On the secondary market, Notice puts its real-time market cap near $881 billion as of early June 2026, reflecting demand modestly above the last round price.

What is OpenAI's secondary share price? Secondary units trade near $714.35 as of early June 2026, about 3% above the roughly $694 last round price. That figure is an algorithmic consensus from secondary activity and reference data, not a guaranteed execution price.

How much revenue does OpenAI generate? OpenAI crossed $20 billion in run-rate revenue by the end of 2025, up 3x year over year, a figure confirmed by its own CFO. It projects revenue more than doubling toward $29 billion in 2026.

Is OpenAI profitable? No. OpenAI burned billions in cash in 2025, projects losses tripling toward $14 billion in 2026, and does not expect to turn a profit until around 2029. It has also signaled roughly $1.4 trillion in data-center commitments.

How does OpenAI compare to Anthropic on price? OpenAI trades at roughly 44x run-rate revenue versus Anthropic near 70x. OpenAI has more revenue and a lower valuation, so it is the cheaper of the two on a multiple basis, though both are expensive against public comps.

Can I buy OpenAI stock directly? No. OpenAI does not permit direct stock transfers. Accredited investors access it indirectly through special purpose vehicles or forward purchase contracts, each carrying fees and counterparty considerations.