Anthropic's journey to the public markets has hit a significant milestone.

According to a report from The Information on Wednesday, Anthropic is evaluating a plan that would permit certain existing shareholders to offload a portion of their stakes during the IPO itself. Simultaneously, the company is exploring the implementation of a lock-up period extending beyond the standard 180 days, a move designed to balance the liquidity needs of early backers and employees with the goal of managing post-listing stock supply and curbing price volatility.

The report indicates that Anthropic intends to publicly unveil its IPO prospectus after the U.S. Labor Day holiday on September 7th, with a subsequent investor day slated for mid-September to brief prospective investors and research analysts. The current target window for the listing is late September or early October, though the final timetable remains subject to change.

Market anticipation for Anthropic's near-term listing is also intensifying. The official social media account for the prediction market Polymarket posted on Thursday during U.S. trading hours, complete with a chart, indicating that market participants now assign an 86% probability to Anthropic completing its IPO before October.

Allowing Existing Shareholders to Sell in the IPO

The Information's report reveals that Anthropic is considering a structure where some current shareholders would directly sell shares as part of the IPO offering. This would mean the IPO could consist of both newly issued company shares and secondary shares from existing holders.

It remains unclear what the final size of such a secondary offering would be, or which specific shareholders would be eligible to participate.

Should this plan materialize, Anthropic would diverge from the approach taken by some of this year's major tech IPOs. The Information previously noted that both SpaceX and Cerebras did not permit existing shareholders to sell stock during their IPO phases, whereas recent large-scale tech listings like CoreWeave and Figma did incorporate secondary share sales.

For Anthropic, allowing some early shareholders to cash out at the IPO stage would help unlock the substantial paper gains accumulated by early investors and employees. The company's valuation has skyrocketed over the past two years, reaching approximately $96.5 billion during its latest funding round in May.

However, insider selling during the IPO phase could also send a negative signal to the market, with investors potentially interpreting it as early shareholders seeking to realize gains just as the company goes public. Consequently, Anthropic is simultaneously weighing stricter lock-up arrangements to mitigate post-listing selling pressure.

Lock-Up Period Could Exceed 180 Days

According to The Information, Anthropic is considering imposing a lock-up period exceeding 180 days on at least a portion of its shareholders.

The 180-day period is a conventional lock-up term in traditional IPOs, primarily designed to prevent insiders and early investors from flooding the market with shares immediately after listing, which could negatively impact the stock price.

By allowing some shareholders to sell at the IPO while subjecting the remaining shares to a longer lock-up, Anthropic could spread the stock supply across different timeframes, thereby reducing the risk of concentrated selling pressure both at the outset and when the lock-up expires.

This is particularly critical for Anthropic. As one of the world's highest-valued AI startups, the scale of its IPO and the level of market attention it garners are likely to far exceed that of a typical tech company. A mass exodus of early investors shortly after listing could significantly amplify stock price swings.

The Information has also reported that Anthropic is considering requiring employees to sell shares through pre-arranged trading plans rather than relying solely on post-earnings trading windows. This arrangement would also assist the company in managing insider stock transactions more orderly after going public.

Prospectus Expected After Labor Day

Regarding the IPO timeline, The Information states that Anthropic plans to publicly release its prospectus after the U.S. Labor Day holiday and hold an investor day in mid-September.

Under the current plan, the company could complete its IPO by late September or early October.

Shay Boloor of Futurum Equities also believes Anthropic's IPO filing could be made public as early as September, with a potential listing at the end of that month. Data released by Polymarket's official account on Wednesday shows the market currently places an 86% probability on Anthropic completing its IPO before October.

If Anthropic proceeds according to this schedule, its prospectus will become a major focal point for the market in the coming weeks. At that juncture, specifics regarding the company's revenue growth, profitability, compute investments, equity structure, and IPO size will provide more direct evidence for the market to assess its ultimate valuation.

Market Bets on Trillion-Dollar Valuation

The immense attention on Anthropic's IPO stems partly from its potential to become one of the largest technology listings in history.

Yahoo Finance previously cited broad market expectations that Anthropic's listing valuation could reach around $1 trillion. The Information has also reported that bankers involved in the IPO preparations have discussed a valuation of approximately $1.5 trillion, with some insiders suggesting it could even reach $2 trillion.

These valuation projections are underpinned by market bets on Anthropic's future revenue trajectory.

A Reuters report from August 15th indicated that Anthropic's IPO valuation is partly contingent on its 2028 revenue forecasts, with the company projecting annual revenue in the range of $190 billion to $200 billion by that year. As of May this year, Anthropic's annualized revenue stood at approximately $47 billion.

If these projections are ultimately included in the prospectus, the capital markets will need to determine whether Anthropic can sustain its exceptionally high revenue growth over the next two years and whether its massive compute investments can translate into sufficient commercial returns.

Therefore, with the prospectus potentially appearing after Labor Day, Anthropic's highly anticipated AI mega-IPO is transitioning from private market valuation discussions to the pricing phase in the public capital markets.