OpenAI is accelerating preparations for a fourth-quarter initial public offering, positioning itself to outpace rival Anthropic in the dash to become the first major generative-AI company to list on public markets. The ChatGPT maker, valued at $500 billion following recent funding, has initiated informal talks with Wall Street banks and bolstered its finance team with hires including Ajmere Dale as chief accounting officer and Cynthia Gaylor as corporate business finance officer, according to The Wall Street Journal .

Executives at OpenAI have voiced private worries that Anthropic, backed by Amazon and Google, could beat them to the punch amid intensifying rivalry. This push comes as both firms grapple with soaring compute costs and ambitious infrastructure builds, with OpenAI committing to at least 10 gigawatts of Nvidia systems over a decade and Anthropic securing $30 billion in Azure capacity plus up to one gigawatt.

OpenAI’s Valuation Surge and Funding Frenzy

Recent reports highlight OpenAI’s pursuit of massive private capital ahead of any listing, with discussions for up to $100 billion from Nvidia, Microsoft, Amazon, and SoftBank, potentially lifting its valuation to $730 billion or higher. Runtime News notes this round aims to address investor concerns over cash burn, quoting The Information: “If this extraordinary funding round comes together, it would calm investors worried about the company’s cash burn.” Meanwhile, Anthropic eyes $350 billion in funding talks, doubling from $183 billion in months, per The New York Times .

Anthropic hired law firm Wilson Sonsini in December to kick off IPO groundwork and has held early discussions with investment banks, signaling a potential 2026 debut. The firm projects $20-26 billion in annualized revenue run rate next year, with 80% from enterprise API customers across 300,000 business accounts, including $1 billion from Claude Code alone.

OpenAI, projecting $30 billion in 2026 revenue against $14 billion losses, relies more on consumer usage from ChatGPT’s 800 million weekly active users. Its path to profitability stretches to 2029 or later, contrasting Anthropic’s cash flow positive target by 2028.

Rivals Gear Up Amid Market Scrutiny

The IPO race extends beyond these two, with SpaceX eyeing a 2026 listing at $800 billion valuation after telling investors it plans to go public within 12 months barring disruptions, as reported by multiple outlets including CNBC . Combined, these firms could test public market appetite for nearly $2 trillion in value, dwarfing 2025 U.S. IPO proceeds.

Analysts question if investors will stomach the valuations. Renaissance Capital’s Nick Einhorn told Gizmodo that household names like these could draw interest despite economic headwinds like tariffs or elections. Yet, enterprise software stocks have plunged amid AI cost fears, with Microsoft’s capex hitting $37.5 billion and Amazon laying off thousands at AWS.

MarketWatch and Benzinga echo the WSJ on OpenAI’s timeline, while Sherwood News flags Amazon’s potential $50 billion stake in OpenAI’s pre-IPO raise.

Enterprise Traction Fuels Anthropic’s Edge

Anthropic’s enterprise focus, with Claude favored for coding and research, positions it as a steadier bet. X posts from insiders like @aakashgupta note its 39x ARR multiple at $350 billion versus OpenAI’s similar ratio on consumer-heavy revenue. Kalshi markets peg a 50% chance of OpenAI listing in 2026, per @StockMKTNewz.

Broader skepticism emerges on X, with @xpasky arguing OpenAI lacks a moat against Google and Anthropic’s superior post-training, calling its capex a potential “pyramid scheme.” @PPLXfinance highlights the trio’s $1.5 trillion combined value prepping for IPOs.

OpenAI’s restructuring to a public benefit corporation, retaining nonprofit oversight with a $130 billion stake, resolved a $40 billion SoftBank deal but drew lawsuits from Elon Musk and scrutiny from California’s attorney general.

Investor Tests and Infrastructure Gambles

Public markets will demand clarity on profitability beyond enterprise deals and compute management. AInvest details Nvidia’s $100 billion OpenAI commitment for 10 gigawatts versus Anthropic’s smaller scale, projecting AI infrastructure from $90 billion in 2026 to $465 billion by 2033.

Runtime News captures Wall Street’s AI reckoning, with Ben Reitzes of Melius Research noting Anthropic’s rapid innovations like Claude Cowork embarrassing incumbents. Microsoft’s Azure grew 39%, yet stocks like ServiceNow fell 11% on cost fears.

As Q4 approaches, OpenAI’s finance expansion signals seriousness, but volatility, midterm elections, or unreadiness could delay. The first AI IPO will set the tone for the sector’s public verdict.