OpenAI Misses Key Revenue & User Targets: What It Means for the Most Anticipated IPO in History
The company behind ChatGPT, arguably the most consequential tech company of the decade, has just revealed something that’s sending ripples through venture capital offices, Wall Street trading desks, and Reddit investing forums alike.
OpenAI missed its own internal revenue and user growth targets. The company didn’t hit the 1-billion-weekly-active-user milestone for ChatGPT by the end of 2025. And this year, it’s already fallen short of monthly revenue targets multiple times, while burning through cash at a rate that makes even crypto winter look frugal.
Oh, and all of this is happening right as the company is sprinting toward what could be the largest IPO in human history — a listing that might value OpenAI anywhere from $850 billion to $1 trillion.
So… what does this actually mean? For the company, for the AI industry, and, honestly, for you, whether you’re an investor, a tech worker, or just someone trying to figure out if it’s time to care about AI stock?
The Breaking Point: What Actually Happened
On April 27, 2026, the Wall Street Journal dropped a report that wiped some of the mystique off the world’s highest-valued AI company. Citing unnamed people familiar with the matter, the WSJ revealed two things OpenAI would rather you not focus on:
- ChatGPT didn’t reach 1 billion weekly active users by the end of 2025, a milestone the company had been gunning for internally but never publicly announced.
- OpenAI missed its 2025 ChatGPT revenue target — and also failed to hit monthly revenue goals multiple times in early 2026.
Now, to be fair, ChatGPT still has roughly 900 million weekly active users — an insanely large number by any standard except the one OpenAI set for itself. Roughly 50 million of those are paying individual subscribers, and 9 million are business accounts.
But here’s the thing about internal targets: when you miss them, investors notice. And when you’re about to ask public market investors to price your company at nearly a trillion dollars, missing your own milestones isn’t just embarrassing, it’s expensive.
The stock market, unlike venture capital, doesn’t grade on a curve.
The Competition That Caught OpenAI Off Guard
So what went wrong? Two words: Google Gemini and Anthropic Claude.
Google Gemini’s surge
According to multiple reports, Google’s Gemini AI platform grew explosively in late 2025, eating directly into ChatGPT’s market share for consumer-facing AI. It turns out that when Google integrates an AI model into Search, YouTube, Gmail, and Android, you know, four products with billions of users, people start using it.
That’s not a technology story. That’s a distribution story.
Anthropic’s enterprise takeover
The more surprising, and, frankly, more concerning, threat comes from Anthropic. Remember how OpenAI was supposed to own enterprise AI? Well…
As of March 2026, Anthropic’s Claude reached 30.6% enterprise market share, closing within 4.6 percentage points of OpenAI’s 35.2%. In some sectors (information, finance, insurance, professional services), Anthropic has already pulled ahead.
In coding specifically? Claude Code holds a dominant 54% market share among developers, more than double OpenAI’s Codex at 21%.
This isn’t a slow erosion. It’s a reshuffling happening in real time. Anthropic did something smart: they focused on enterprise trust and developer experience from day one, while OpenAI was busy trying to be everything to everyone.
The $600 Billion Elephant in the Server Room
Now we need to talk about what might be the single most important number in this entire story, and it’s not a user count or a revenue figure.
It’s $600 billion.
That’s the rough total of OpenAI’s long-term compute spending commitments, contracts CEO Sam Altman spearheaded last year to lock down data center capacity for years to come. Some estimates put the full infrastructure pipeline as high as $1.4 trillion over the next eight years, though OpenAI has since walked that number back.
Here’s the logic behind it, and to be fair, it’s not crazy:
Altman has argued, for years, that the single biggest thing holding back AI progress is compute scarcity. If you don’t have enough GPUs and data centers, you can’t train bigger models, and you can’t serve inference to billions of users. So he went on what you might call a compute-buying spree, signing massive contracts with data center operators and chip suppliers.
The problem? These contracts don’t pause when revenue slows down.
CFO Sarah Friar’s warning
This is where the tension gets real. According to the WSJ report, CFO Sarah Friar has told other senior leaders that if OpenAI’s revenue doesn’t grow fast enough, the company may struggle to pay for those compute contracts.
Let that sink in. The CFO of a company valued at $852 billion is worried about making payments on its infrastructure bills.
And she’s not wrong to worry. Deutsche Bank estimates OpenAI could accumulate $143 billion in negative free cash flow between 2024 and 2029 before turning profitable. Even after raising $122 billion in the largest funding round in Silicon Valley history, a staggering sum, the company’s own projections suggest that money could be gone within three years.
The board has now started scrutinizing Altman’s compute deals more aggressively, asking questions they probably should have been asking from the start.
The Leadership Tension No One’s Talking About
If you read between the lines of the WSJ report, there’s a deeper story here, and it’s about two very different philosophies colliding inside one company at the worst possible time.
Sam Altman is, at his core, a founder-visionary. He believes the AI revolution is winner-take-most, and that whoever builds the biggest compute infrastructure first will have an insurmountable advantage. His instinct is always to push forward, more GPUs, bigger models, faster timelines.
Sarah Friar is a former investment banker and Wall Street veteran. Her job is to make sure the company doesn’t fly too close to the sun. She’s been privately pushing for more cost discipline, stronger internal controls, and a more measured approach to the IPO timeline.
The WSJ report suggests Friar has told the board that OpenAI is not yet ready to meet the rigorous disclosure and compliance standards required of a public company. Altman, meanwhile, is said to prefer a more aggressive IPO schedule, viewing going public as a way to lock in capital and momentum before competitors can pull ahead.
The two issued a joint statement calling any suggestion of rift “ridiculous,” saying they are “totally aligned on buying as much compute as we can and working hard on it together every day.”
Which… is exactly what you’d expect two senior executives to say publicly, regardless of what’s happening behind closed doors.
IPO Timeline: Slipping or Still on Track?
Officially, OpenAI has been aiming for a Q4 2026 IPO on the Nasdaq, targeting a valuation between $850 billion and $1 trillion. The company has hired a chief accounting officer, a head of investor relations, and begun informal talks with Wall Street banks.
Unofficially? There are reasons to doubt that timeline.
- Friar herself has privately expressed that 2027 might be more realistic.
- The company’s second-in-command, Fidji Simo, recently went on unexpected medical leave, creating questions about leadership stability at a critical moment.
- And then there’s the Elon Musk lawsuit.
The Musk factor
On April 27, 2026, literally the day the WSJ report dropped, Elon Musk’s lawsuit against OpenAI went to trial. Musk is seeking up to $134 billion in damages and asking the court to remove Altman as CEO, reverse OpenAI’s conversion to a for-profit entity, and restore its original nonprofit status.
That’s not a sideshow. That’s an existential threat to the entire IPO. If Musk wins any significant portion of his case, the for-profit restructuring that made an IPO legally possible could be unwound. IPOs don’t happen under those conditions.
Even the uncertainty itself is damaging. Secondary market trading in OpenAI shares has reportedly cooled, with some investors getting nervous about what the trial could mean for the company’s path to going public.
The Bull vs. Bear Case for OpenAI’s IPO
If you’re trying to figure out whether OpenAI is a generational buying opportunity or a cautionary tale in the making, you’re not alone. Here’s how to think about both sides.
🟢 The Bull Case
- GPT-5.5 is really, really good. The latest model, released just days ago, topped multiple industry benchmarks, particularly in coding and agentic tasks, and is deeply integrated with Codex, OpenAI’s developer platform.
- The enterprise business is growing fast. Nearly half of OpenAI’s 2026 revenue is expected to come from enterprise customers, a much stickier, more predictable revenue stream than consumer subscriptions.
- Advertising is a new, untapped revenue stream. ChatGPT has started running ads on free tiers, and while it’s early, ad revenue gives OpenAI a second way to monetize that massive free user base.
- $122 billion in the bank. The war chest is enormous by any standard, even if it won’t last forever.
- Retail investor access is coming. OpenAI has said it will reserve IPO shares for individual investors, a rare move for a mega-cap listing, and demand could be enormous.
🔴 The Bear Case
- The valuation math doesn’t work in traditional terms. At $850 billion on roughly $25 billion in annualized revenue, OpenAI trades at ~34x sales. Mature SaaS companies trade at 5-10x. Even Snowflake at its 2021 peak topped out around 50-80x, and its margins were much better.
- Cash burn is accelerating, not decelerating. Annual losses could hit $57 billion by 2027. The company may not reach profitability until 2029 or 2030.
- Competition is intensifying on every front. Google has distribution. Anthropic has enterprise trust. DeepSeek is proving that open-source models can compete at a fraction of the cost. Meta is giving away powerful models for free.
- Subscriber churn is a persistent problem. ChatGPT’s defection rate remains a headache, users try it, get excited, and then drift away.
- The Musk lawsuit is a genuine wildcard. Even if OpenAI ultimately prevails, litigation uncertainty tends to depress IPO valuations.
What This Means for You
Maybe you’re an accredited investor. Maybe you’re a retail investor who’s been watching the AI space from the sidelines. Or maybe you just work in tech and want to know where things are heading.
Here’s what I think you should keep in mind:
If you’re considering investing in the OpenAI IPO:
- Wait for the S-1 filing. That’s the SEC document where OpenAI will have to disclose real financials, revenue breakdown, margins, cash burn, risk factors. Everything else until then is speculation.
- Compare OpenAI’s numbers head-to-head with Anthropic’s (which may file its own S-1 around the same time).
- Watch for revenue diversification. A company reliant on one product (ChatGPT) with one major cost driver (compute) is inherently riskier than one with multiple, independent revenue engines.
- Pay attention to the leadership question. A pre-IPO company with visible tension between its CEO and CFO is not ideal.
If you want exposure before the IPO:
- The ARK Venture Fund (ARKVX) holds OpenAI shares as ~11% of its portfolio.
- Robinhood recently launched a closed-end fund with pre-IPO stakes in OpenAI and other private AI companies.
- AngelList’s USVC Fund now allows non-accredited investors to buy into a basket of AI startups (including OpenAI) for as little as $500.
But, and this matters, pre-IPO shares come with their own risks: limited liquidity, valuation opacity, and no guarantee of a successful public listing.
If you just want to understand the AI industry: The OpenAI story is really a story about every AI company right now. They’re all making the same bet: spend enormous amounts of money now, build infrastructure that competitors can’t match, and trust that revenue will eventually catch up to the spending.
It’s not a crazy bet. But it’s also not guaranteed to pay off. And OpenAI’s stumbles are the first major signal that reality might be more complicated than the hype suggests.