The Dealflow by Founders Capital - Edition 22

Key News and Trends

OpenAI’s valuation goes vertical. Fresh off an $8.3B raise from investors including Dragoneer, Blackstone, and T. Rowe Price, OpenAI is now reportedly targeting a $500B valuation through a multi-billion-dollar secondary sale of employee shares. Thrive Capital and other existing investors are leading the discussions, with the sale designed to retain talent amid poaching pressure from Meta. Microsoft, which holds a major strategic stake, is said to be negotiating for a third of OpenAI’s equity. The ChatGPT-maker also announced it has reached 700 million weekly active users and is preparing to release GPT-5. Read more here and here

Dead Funds, No Exit. Private equity LPs are demanding liquidity, but an estimated $1.5 trillion is now trapped in aging “zombie funds” that can’t exit portfolio companies or raise new capital. These funds, often past their original timelines, persist in limbo, frustrating investors eager for returns. As GPs stretch holding periods and avoid markdowns, LPs are increasingly considering secondary sales or demanding more flexible alternatives. The squeeze is real, and dry powder doesn’t equal deployable cash. Read more here

SoftBank rides the AI wave. Riding Nvidia and Coupang gains, SoftBank swung to a ¥422B Q1 profit. Despite delays to its $500B Stargate project with OpenAI, Son remains all-in on AI infrastructure. Read more here

Teneo gets the royal treatment. Liechtenstein’s LGT Capital took a minority stake in CEO advisory firm Teneo, valuing it at $2.3B and giving CVC a partial exit amid ongoing market consolidation. Read more here

Founder’s Take: Dead Funds, No Exit

There’s a growing tension in private equity, and it’s coming from LPs stuck in decade-old funds with no clear exit in sight. These so-called “zombie funds” aren’t delivering returns, but they’re not winding down either. Investors are left in limbo, watching their capital sit idle while GPs push out timelines and avoid tough calls.

This is exactly why we built Founders Capital as a deal-by-deal platform. Instead of locking investors into long-term blind pools, we give them the flexibility to choose the deals they want, when they want them. That means no waiting around, no surprises, and no capital trapped in funds that have lost their momentum.

As more investors rethink how and where they allocate, we believe control and transparency are no longer optional, they’re essential.

Top Venture Deals

OpenAI – Multi-Billion Dollar Secondary at $500B Valuation (Thrive Capital, Existing Investors)

• OpenAI is in early talks to conduct a secondary share sale allowing current and former employees to cash out at a $500B valuation, up from $300B just months ago. The deal, expected to be in the billions, comes on the heels of an $8.3B primary raise and would mark one of the most valuable liquidity events in private tech history. Thrive Capital and other existing backers are said to be leading interest. Read more here

Rillet – $70M Series B (Andreessen Horowitz, ICONIQ)

• San Francisco-based Rillet, which offers AI-powered accounting automation integrating with platforms like Salesforce and Stripe, raised $70 million in a Series B. The round brings its total funding past $100 million and was led by Andreessen Horowitz and ICONIQ. The company also saw strong investor confidence from Sequoia, Oak HC/FT, and FOG Ventures, as it accelerates product development amid a doubling of ARR in just 12 weeks.  Read more here

Chai Discovery – $70M Funding Round (Menlo Ventures, DST Global, Thrive Capital, OpenAI)

• Substack, the San Francisco-based newsletter and social platform, has raised a $100M Series C at a $1.1B valuation. The round was led by BOND and The Chernin Group, with Andreessen Horowitz, Rich Paul, and Jens Grede also participating. The eight-year-old startup now boasts over 5 million paid subscriptions and plans to use the funding to expand tools and global reach. Read more here.

Upcoming Public Offerings

Carro

• Singapore-based Carro, Southeast Asia’s largest online used-car marketplace, is preparing for a US IPO as early as 2026, targeting a raise of up to $500M at a valuation north of $3B. If successful, it would mark the region’s largest listing in the US since Sea Group’s 2017 debut and establish Carro as the first major AI-driven automotive platform from Singapore to go public in New York. Backed by Temasek and SoftBank, the company is on track to hit $100M EBITDA by March 2026. Read more here

Firefly Aerospace

• Firefly Aerospace is set to debut on Nasdaq under the ticker FLY, pricing its IPO between $41 and $43 per share. The raise could bring in up to $868 million, elevating the company’s valuation to approximately $6.3 billion, following its landmark Blue Ghost lunar lander mission and a robust contract pipeline. Read more here

See you in the next edition,
The Founders Capital Team