The Dealflow by Founders Capital - Edition 35

Key News and Trends

Anthropic’s $70B Ambition: The AI Firm Turning Cash Flow Positive

Anthropic expects to generate $70B in revenue and $17B in cash flow by 2028. The forecast reflects explosive enterprise demand, with clients like Microsoft, Deloitte, and Cognizant driving adoption of Claude for regulated industries. Revenue is on track to hit $9B ARR by end-2025 and $26B in 2026. The company’s gross margins are projected to climb from –94% to 77% by 2028, a staggering operational turnaround. Read more here

OpenAI x Amazon: $38B Cloud Pact Powers the AI Arms Race

OpenAI has inked a $38B, seven-year cloud deal with Amazon Web Services, marking its first-ever partnership with the cloud giant. The agreement gives OpenAI access to AWS infrastructure. This latest deal brings OpenAI’s total cloud commitments to nearly $600B, underscoring the new era of compute nationalism, where AI powerhouses secure resources like oil rights. Amazon, under pressure to catch up with Microsoft and Google, now gains a crucial foothold in OpenAI’s trillion-dollar compute empire. Read more here

Sequoia Shifts the Guard: Alfred Lin and Pat Grady Take the Helm

Sequoia Capital has announced a leadership transition as veteran Roelof Botha steps down, passing stewardship to Alfred Lin and Pat Grady. Botha, who guided Sequoia through the pandemic, FTX’s collapse, and the firm’s reorganisation into a master fund, will remain as a general partner and adviser. Lin, known for early bets on Airbnb and DoorDash, will lead early-stage investing, while Grady, who backed Zoom, Snowflake, and OpenAI, will oversee late-stage strategy. The handover marks a new chapter for the world’s most influential venture firm, a generational baton pass in Silicon Valley’s oldest dynasty. Read more here

Google’s $32B Wiz Deal Clears U.S. Antitrust Review

Google’s $32 billion acquisition of Wiz has officially cleared U.S. Department of Justice antitrust review, paving the way for one of the largest cybersecurity M&A deals in history. Wiz, founded by ex-Microsoft executives, turned down a $23B offer in 2024 before agreeing to the higher valuation earlier this year. The acquisition is expected to close in early 2026, solidifying Google’s role as the default AI-era infrastructure provider, owning not just compute, but the security rails that guard it. Read more here

Founder’s Take: Anthropic's $70 billion ambition

Anthropic's $70 billion ambition. They're the AI firm turning cash flow positive. They forecast $70 billion in revenue and $17 billion in cash flow by 2028. The enterprise is exploding in demand - Microsoft, Deloitte, Cognizant, are all pushing Claude into regulated industries. Their ARR trajectory is pretty insane. They've gone from ~$1 billion to an expected $9 billion in 2025 and are projecting $26 billion for 2026. Their growth margins are one of the fastest operating turnarounds in modern-day tech. 

While OpenAI continues to invest heavily in compute and product expansion, Anthropic appears focused on building a more immediately sustainable enterprise model. The narrative is evolving - frontier AI isn’t just about R&D; it’s showing strong commercial potential. The real money in AI may not be in consumer apps, but in verticalized enterprise deployment across high-compliance sectors like insurance, healthcare, finance, legal, and defence.

Top Venture Deals

Ripple: $500M Growth Round (Fortress Investment Group, Citadel Securities, Pantera Capital)

• Ripple, the digital assets and infrastructure firm behind XRP, has raised $500M at a $40B valuation, led by Fortress, Citadel Securities, and Pantera Capital. The round follows six acquisitions in two years as Ripple expands beyond payments into crypto custody, prime brokerage, and corporate treasury management. With its own USD-backed stablecoin now live and institutional demand surging under the GENIUS Act, Ripple is positioning itself as the bridge between traditional finance and on-chain liquidity. Read more here

Whatnot: $225M Series D (CapitalG, DST Global)

• Los Angeles–based Whatnot, the livestream shopping platform dubbed “QVC for the TikTok era,” has raised $225M at an $11.5B valuation, led by CapitalG and DST Global, with Sequoia and Alkeon joining the round. The company has doubled its gross merchandise value to $6B, operating across nine markets and averaging 80+ minutes of daily engagement per user. With over $968M total funding and a fast-expanding creator network, Whatnot is cementing itself as the social-commerce infrastructure for Gen Z retail. Read more here

Crusoe: $120M Employee Stock Sale at $13B Valuation

• Crusoe Energy Systems, the clean-energy AI data centre operator, is conducting a $120M secondary sale valuing the company at $13B, up 30% from its recent $10B Series E. The Denver-based firm, which powers data centres for Oracle and OpenAI, has raised nearly $4B to date. Its 1.2GW Texas campus, now partially live, highlights Crusoe’s evolution from flared-gas mitigation startup to “Neocloud” infrastructure provider, the clean compute layer of the AI economy. Read more here

Upcoming Public Offerings

OpenAI

• Despite market speculation, OpenAI CFO Sarah Friar told The Wall Street Journal that an IPO is “not on the cards” for now, dampening expectations of a trillion-dollar near-term listing. Friar emphasised the company’s focus on R&D and infrastructure expansion, noting that OpenAI could reach break-even quickly but wants government support for data-centre investments before going public. The remarks follow OpenAI’s corporate restructuring and multi-billion cloud deals with Microsoft, Amazon, and Google. Read more here

Gloo Holdings

• Faith-focused technology firm Gloo Holdings has filed for a U.S. IPO targeting a $900M valuation, planning to raise up to $109M by offering 9.1M shares priced between $10–12 each. The Boulder, Colorado, based company develops digital tools for churches and religious organisations, including AI chatbots and virtual assistants that deliver “safe search” features and Bible-based responses. Former Intel CEO Pat Gelsinger joined earlier this year as Head of Technology and Executive Chairman, tasked with scaling Gloo’s AI infrastructure. Read more here

See you in the next edition,
The Founders Capital Team

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