OpenAI’s $6B Secondary: The Largest Employee Liquidity Event in Tech History

How a $500 billion valuation is creating more non-founder wealth than any tech transaction ever

The Numbers Are Just … Insane.  And Unprecedented.

OpenAI is preparing to sell around $6 billion in stock as part of a secondary sale that would value the company at roughly $500 billion.

But here’s what the headlines missed—this isn’t just another funding round. This is the largest non-founder employee wealth creation event in tech history. Full stop.

Massive M&A deals like Google’s proposed $23 billion Wiz acquisition might move more total dollars. But even if Wiz employees owned 15% of the company (which would be extraordinarily high), that’s $3.45 billion in employee liquidity assuming it was all sold in the deal (which it never is). OpenAI’s $6 billion secondary is nearly double that—and it’s going entirely to employees and former employees, all in one shot.

But wait—what about public company employee wealth? NVIDIA offers perhaps the closest comparison. NVIDIA’s stock-based compensation for the twelve months ending April 30, 2025 was $11.791B, and in the last year, stock-based compensation has jumped more than five times the previous year, up to $4.4 BILLION.

However, there’s a critical difference: NVIDIA’s stock compensation vests over time and employees sell throughout the year based on individual vesting schedules. Nearly 11 million shares have been sold by Nvidia executives and directors in 2024, the most in a year since at least 2020 after adjusting for stock splits, totaling more than $1 billion in shares over the last year.

OpenAI’s $6B is concentrated liquidity—all happening at once, all available immediately to employees. That’s unprecedented scale and timing.

To put this in perspective: The largest IPO of 2024 was Lineage’s $4.8 billion listing, and the U.S. saw 109 IPOs in H1 2025, raising $17.1 billion total. OpenAI’s single secondary sale is larger than the biggest IPO of the year and represents more than one-third of the entire first-half IPO market.

A Brand New World for Employee Equity

The Scale is Unprecedented for Tech Employees

When ServiceTitan went public in December 2024, it was celebrated as one of the year’s biggest tech debuts. The ServiceTitan IPO sold 8.8 million shares at $71 each, raising about $625 million at a $7.6 billion valuation.  That’s roughly 10% of what OpenAI employees are getting in liquidity from just one secondary sale.

Even the largest M&A deals rarely create this much employee wealth. Take the Wiz acquisition at $32 billion—even with generous employee ownership assumptions (say 15%), that’s $4.8 billion in total employee value.  Assuming employees completely cash out.  If they selling say half their shares (still high), that would be $2.4 billion.  For selling the entire company.

NVIDIA, with its legendary stock run-up, provides an interesting comparison. NVIDIA’s annual stock-based compensation hit $4.737B in 2025, and insiders have sold over $1.8 billion in stock in 2024 alone. But that’s spread across 29,600 employees over an entire year through vesting schedules.

OpenAI’s single secondary exceeds NVIDIA’s entire annual stock compensation expense and provides immediate liquidity rather than vesting over time. This likely isn’t their last liquidity event before IPO either.

But it goes deeper than raw dollars. By allowing employees with at least two years of tenure to sell shares, the company addresses a key vulnerability: the risk of losing AI experts to rivals like Meta, which has lured away key figures such as Shengjia Zhao, co-creator of ChatGPT.

The Revenue Foundation is Real

This isn’t ZIRP-era speculation. Annual recurring revenue (ARR) has surged to a stunning $12 billion in July 2025, up from $10 billion in June, with projections of $20 billion by year-end. That’s $20B ARR—most SaaS companies would kill for $200M ARR.

The enterprise traction is equally impressive: enterprise adoption of ChatGPT, now serving 5 million paid business users—a 67% increase in six months.

The Liquidity Strategy Every Late-Stage Founder Needs To Study

Secondary Sales as Talent Retention

Here’s what OpenAI understood that most SaaS companies miss: in a talent war, liquidity is your secret weapon. This approach mirrors trends in the broader tech sector, where private companies increasingly use secondary markets to provide liquidity without the volatility of public markets.

Think about your own cap table. How many of your best engineers have been at the company for 3+ years with zero liquidity? How many are getting calls from competitors offering cash compensation that dwarfs their equity upside?

The New Playbook: Primary + Secondary

The deal also reflects a shift in capital allocation priorities. While OpenAI’s $40 billion primary funding round (led by SoftBank) focuses on infrastructure and R&D, the secondary sale targets employee retention. This dual-track strategy—raising capital for growth while rewarding contributors—aligns with the AI sector’s broader move toward pragmatic value creation.

This is brilliant strategic thinking:

• Primary round: Fund growth and operations
• Secondary sale: Retain talent and provide liquidity
• Result: Best of both worlds without IPO complexity

Employee Liquidity Comparison: The Numbers Don’t Lie

Let’s put OpenAI’s $6B secondary in context with a table comparing estimated employee liquidity from recent major tech events:

Note: Employee liquidity estimates based on typical equity ownership ranges, public filings, and industry analysis. NVIDIA figure represents annual stock compensation expense, not immediate liquidity.

Key Takeaways:

1. OpenAI’s per-employee liquidity ($3M) is 12x higher than Reddit’s IPO
2. Even compared to massive M&A deals, OpenAI delivers more total employee value
3. NVIDIA’s $11.8B is spread over 30K employees and vests over time—OpenAI’s is immediate
4. No other single liquidity event comes close to $6B in employee value

The Math That Makes Competing For Top AI Talent … Tough

Let’s trace OpenAI’s valuation journey:

• March 2024: $40 billion round at a $300 billion valuation
• August 2025: Secondary at $500 billion valuation

That’s a 67% increase in 5 months. On a $300 billion base. The absolute dollar increase ($200B) is larger than the total valuation of most unicorns.

Competitive Moat in Numbers

OpenAI’s valuation dwarfs that of peers. Anthropic, its closest rival, is valued at $61.5 billion as of March 2025, while xAI (Elon Musk’s venture) sits at $80 billion.

OpenAI is now worth more than 6x its closest competitor. In SaaS terms, that’s like Salesforce being worth 6x ServiceNow, HubSpot, and Workday combined.

What This Means for Your Scale-Up / Start-Up

Talent Competition Just Got Nuclear

Every AI engineer who was considering your Series B startup just got a reality check. OpenAI employees with 2+ years tenure could be looking at life-changing liquidity events. Your equity compensation packages need an immediate audit.

The New Liquidity Standard

The employee share sale underscores how private companies are using secondary transactions not only to reward early workers but also to establish updated valuations in a competitive capital market.

This isn’t just an OpenAI thing. Stripe has done multiple employee tender offers. Canva, valued at $32 billion, has provided secondary liquidity. The new standard for top-tier talent is: “Show me the liquidity.”

Revenue Multiples Reset

At $500B valuation and $20B projected ARR, OpenAI trades at 25x revenue. That’s somewhat rich even for a growth company, but it reflects the market’s belief in AI’s transformative potential.

For comparison, most public B2B companies trade at 5-15x revenue. The premium for AI integration and market dominance is real and substantial.

The Strategic Implications

Infrastructure as Competitive Advantage

Strategically, OpenAI’s Stargate Project—a $500 billion initiative with SoftBank and Oracle—positions it as a cornerstone of U.S. AI infrastructure. This project, which includes $100 billion in immediate funding and 100,000+ job creation, aligns with national security and economic priorities.

When your company becomes critical national infrastructure, traditional valuation metrics go out the window.

The IPO Question

Microsoft remains OpenAI’s largest backer, with a multiyear partnership that has integrated the startup’s technology into its products and cloud platform. OpenAI is also considering a corporate restructuring that would move it away from its current capped-profit model, a step that could pave the way for an eventual IPO.

The secondary sales at this scale suggest IPO preparation. But why go public when you can create more employee value privately?

The Bottom Line

OpenAI’s $6 billion secondary isn’t just a financial transaction—it’s rewriting the rules for employee wealth creation in tech. This is more non-founder employee liquidity than any M&A deal, IPO, or previous secondary sale in history.

Key Takeaways:

1. Liquidity is the new equity: $6B in employee liquidity sets a new bar that even massive M&A deals struggle to match for non-founder employees
2. Secondary sales at scale: This exceeds the employee value creation from most $20B+ acquisitions and represents a new category of wealth distribution
3. Revenue quality matters: $20B ARR provides the foundation for a $500B valuation—growth without revenue is dead
4. Strategic thinking wins: Primary rounds fund growth, secondaries retain talent, and the combination creates sustainable competitive advantage

For founders, the question isn’t whether AI will disrupt your business model. It’s whether you’re thinking big enough about talent retention and employee value creation in an AI-dominated landscape.

The companies that figure out how to provide meaningful liquidity to employees—whether through secondaries, tender offers, or creative equity structures—will win the talent war. The ones that don’t will watch their best people join companies that understand the new rules of the game.

OpenAI just wrote the playbook. The question is: how can you compete at this level?  The answers are as confusing as the times we live in now.