Sam Altman is betting that waiting for the perfect valuation is worth the risk, even as OpenAI's IPO timeline stretches and competitors move faster. The OpenAI CEO has drawn a firm line at a $1 trillion valuation for the company's initial public offering, according to reports, and is willing to delay the listing until 2027 rather than accept a lower price. This high-stakes gamble comes as Anthropic, OpenAI's closest rival, has already filed confidential IPO paperwork with a $96.5 billion valuation and may reach public markets first.

Why Is OpenAI's IPO Taking So Long?

OpenAI confidentially filed its S-1 paperwork in early June 2026, but the company has not yet launched investor roadshows or tested market pricing. According to people familiar with the matter, there was already an internal understanding when the filing occurred that the process "might take a while". Altman's insistence on a $1 trillion valuation has created a standoff: advisors have presented two paths, either wait for market conditions that support that figure or go public now at a discount. Altman has shown no willingness to compromise on the number.

The caution reflects a sobering lesson from SpaceX's recent public debut. Elon Musk's company priced its IPO at a staggering $1.77 trillion valuation but subsequently saw its stock fall from a high of $202 to $153, dipping below the offering price. Investment bankers are now using SpaceX's performance as a cautionary tale when advising clients. If SpaceX, with its proven scarcity value in physical-world infrastructure, could not hold a trillion-dollar-plus valuation, the argument goes, OpenAI may face an even steeper challenge in convincing public markets that its digital-world dominance justifies a similar premium.

What Makes OpenAI's Valuation Challenge Different From SpaceX?

Market analysts point to a fundamental distinction between the two companies. SpaceX sells scarcity in the physical realm through reusable rocket technology, yet it was still punished by public markets. OpenAI sells substitutability in the digital realm. ChatGPT has 900 million weekly active users and generates roughly $2 billion in monthly revenue, but that private-market valuation of $852 billion remains untested in the harsh light of quarterly earnings disclosures.

The company's financial picture is complex. OpenAI generated roughly $13 billion in revenue in 2025, with monthly revenue now running at about $2 billion. However, spending on data center construction, AI talent wars, and enterprise sales expansion is climbing on an even steeper curve. The company has raised $12.2 billion in private funding to fuel this effort, and remaining private allows OpenAI to avoid the quarterly scrutiny of public markets while preserving operational flexibility.

How Could Anthropic's IPO Change the Game?

Complicating OpenAI's calculus is Anthropic's faster timeline. The company confidentially filed its own S-1 on June 1 with a valuation set at $96.5 billion, more than $10 billion above OpenAI's last private round. According to Bloomberg, OpenAI internally expects Anthropic to reach the public markets first. Anthropic's timeline is reportedly more compressed, with the company at one point considering completing its listing as early as October 2026.

If Anthropic debuts first, its initial trading performance will serve as the first public-market benchmark for the entire AI industry. A strong showing could validate the lofty valuations across the sector; a weak one could reinforce the SpaceX narrative and further complicate OpenAI's path to $1 trillion. The uncertainty is already rippling through related markets. SoftBank Group, which is expected to have committed approximately $65 billion to OpenAI by October, saw its shares drop more than 12% over two days. Japanese memory-chip maker Kioxia also fell 12%, as the company had briefly topped the Nikkei 225 by market capitalization as a direct beneficiary of AI infrastructure spending.

What Are the Market Signals About OpenAI's IPO Timeline?

Prediction markets are reflecting growing skepticism about a near-term OpenAI listing. On Kalshi, traders now assign just a 59% probability that OpenAI will officially announce an IPO before March 2027, and 73% by June 2027. Only about one-third of contracts are betting on any action within 2026.

The market is left to piece together a valuation picture from indirect signals: SoftBank's stock swings, SpaceX's market pricing, Kioxia's supply-chain dynamics, and Anthropic's financing trajectory. It is an incomplete and unstable model, assembled from fragmented market signals. STARTRADER, a global multi-asset brokerage, has launched pre-IPO contracts for difference (CFD) products on OpenAI and Anthropic, giving traders a direct route to wager on the valuations of both companies before they hit traditional exchanges. The products, trading under the symbols OPENAIUSD and ANTHUSD, went live on June 29 and offer 5x leverage with round-the-clock access seven days a week.

How to Assess OpenAI's IPO Strategy and Valuation Prospects

• Monitor Anthropic's Performance: If Anthropic reaches public markets first, its stock performance will set the benchmark for AI company valuations and directly influence how investors view OpenAI's $1 trillion ask.
• Track Financial Metrics: OpenAI's monthly revenue of $2 billion and annual spending trajectory will become public once the S-1 process fully activates, allowing a genuine reassessment of what has been called "the most expensive startup in history."
• Watch Market Sentiment: Prediction market odds on Kalshi and related platforms provide real-time signals about investor confidence in a near-term OpenAI listing, with current odds suggesting skepticism about 2026 action.
• Observe Related Stock Movements: SoftBank and Kioxia share prices serve as indirect indicators of market expectations around OpenAI's IPO timeline and the broader AI infrastructure investment cycle.

Altman is betting that time is on his side. He wants the market to see not just growth but irreversible embeddedness, a world where Claude's rise looks like a temporary challenge, where GPT-5 demonstrates a generational leap, and where consecutive quarters of record revenue gradually erase the shadow cast by SpaceX. The $1 trillion narrative, analysts note, is not merely symbolic. In Silicon Valley, valuation is a form of power: it influences talent acquisition, cloud-computing bargaining power, and survival elasticity amid global tech competition and geopolitical risk.