OpenAI Courts Private Equity with 17.5% Guaranteed Return on Enterprise Joint Venture Preferred Stakes

OpenAI is approaching private equity firms with an offer that includes a guaranteed minimum return of 17.5 percent on preferred equity stakes in its new enterprise joint venture.

The terms, first reported by Reuters, are more generous than rival Anthropic’s structurally similar joint venture pitch, which includes no equivalent financial guarantee.

OpenAI’s proposal carries a pre-money valuation of roughly $10 billion, with sponsors collectively committing around $4 billion. TPG is the anchor investor, with Advent International, Bain Capital, and Brookfield Asset Management joining as co-founding participants.

Anthropic has held discussions with Blackstone, Hellman & Friedman, and Permira for its own vehicle.

Both companies are targeting buyout firms as enterprise distribution channels via access to portfolio companies. A multi-sponsor partnership model allows the providers to sign up hundreds of companies at once and bypasses typical deal-by-deal enterprise sales cycles.

The hope is that there is some level of enduring product stickiness once one provider’s models are customized and embedded into workflows.

OpenAI’s terms also include additional sweeteners beyond the headline return: seniority over other joint venture partners, downside protection, and early access to models not yet in public release. The venture expects to generate revenue from implementation services, revenue-sharing on deployed products, and co-ownership of newly created tools.

Several additional firms are in discussions for smaller stakes without board seats or lead roles.

But not every firm is biting. Thoma Bravo, after internal discussions led by managing partner Orlando Bravo, declined to participate in either venture.

Bravo questioned the long-term profit profile of both structures, noting that many Thoma Bravo portfolio companies are already deploying AI tools without the intermediation of a formal joint venture.

At least one other firm reached the same conclusion independently, says Reuters.

The guaranteed return has also raised eyebrows and fuelled concerns over OpenAI’s financial health.

The company’s annualized revenue crossed $20 billion in 2025, a 233 percent year-over-year increase, but internal projections show $14 billion in losses in 2026 alone, with profitability not expected until 2029.

Making matters worse is OpenAI’s relative stagnation.

Anthropic’s enterprise market share grew from 18 percent to 29 percent in 2025, with eight of the Fortune 10 counted as customers, according to Menlo Ventures data. The company raised a $30 billion Series G at a $380 billion valuation in February 2026 and has lifted its internal 2026 revenue target to as much as $18 billion. Where OpenAI is paying for enterprise access, Anthropic’s pitch rests on a product track record already in place.

That’s led to internal reorganization at OpenAI and plans to shed non-core activities to refocus on the enterprise market.

Starting its consolidation push, the firm announced this week it is shutting down its Sora video generation product and backing out of a related $1 billion video deal with Disney.