Enterprise Weekly #527: Defensibility in AI, New Agentic Systems Drop, and More
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In the age of AI, defensibility remains the big question for many startups.
This week, news surfaced that AI coding giant Cursor is operating with negative gross margins despite doing more than $500M in annualized revenue.
To put their challenging unit economics in perspective, every time developers use Cursor to generate code, the company pays the piper. In this case, it’s consistently footing a large bill to Anthropic and the company’s costs are greatly exceeding the $20 monthly subscription for its Pro plan.
This comes at an interesting time where Anthropic’s Claude Code is gaining traction and even instituted weekly rate limits for Claude Pro and Max.
While both Cursor and Claude Code are experiencing tremendous usage, power users are driving disproportionate compute costs for both companies. These customers pay the same subscription price as everyone else, but use the product so heavily that it throws the unit economics out of balance.
Reading between the lines, Cursor’s outsourcing its LLM capabilities, arguably the most valuable part of their product, to its biggest competitor, putting themselves in a very tricky situation. As the code editing space heats up, we’re wondering if Cursor can build their own model that competes with Anthropic, or if they’ll forever be at the mercy of the research lab overlords.
Whether you’re Cursor or Anthropic, delivering AI at scale is far from cheap and growth comes at a cost. Sooner rather than later, this will have to be reflected in prices. Cursor’s existential risk of relying on third-party models comes at a cost, while Anthropic needs to spend a significant amount on compute to serve that inference. OpenAI has notably 15x’d their compute since 2024, and Sam Altman has said that they’re planning on doubling compute in the next few months.
That being said, innovation in the infrastructure layer has always helped bring improvements in efficiency and democratize use-cases that were previously cost-prohibitive. Speaking of agentic infrastructure, our teammates Priyanka and Proby just released the July edition of their State of Agentic Systems newsletter, where they dive into advancements in context engineering, agent planning and delegation, and model training. Give it a read!
📚 Read more news:
WSJ: OpenAI’s Rocky GPT-5 Rollout Shows Struggle to Remain Undisputed AI Leader
TechCrunch: Perplexity’s bid for Google Chrome could be just the beginning
VentureBeat: Gartner: GPT-5 is here, but the infrastructure to support true agentic AI isn’t (yet)
Bloomberg: CoreWeave IPO Investors Sitting on Big Gains Get Chance to Sell
WIRED: Inside Dylan Field’s Big IPO—and His Even Bigger Plans for Figma
🧵 Read more threads:
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Technology: Digital Identity Verification
Funding: $744.4M from Work-Bench, Accel, Scale Venture Partners, Flint Capital, T. Rowe Price, and others
🌟 Company of the Week 🌟
Mako raises $8.5M led by M13
Infrastructure / Dev Tools - Seed - New York, NY
Founders: Waleed Atallah, Łukasz Dudziak
Uno Platform raises $2.5M led by AQC Capital and Desjardins Capital
Infrastructure / Dev Tools • Seed • Montreal, Canada
Cuttable raises $4.5M led by Square Peg
Sales / Marketing • Seed • Melbourne, Australia
Archestra raises $3.3M led by Concept Ventures
Infrastructure / Dev Tools • Pre-Seed • London, UK
Infinity Loop raises $5M led by Glasswing Ventures and TIAA Ventures
Future of Work • Seed • New York, NY
Dealops raises $7M led by Pear VC and General Catalyst
Sales / Marketing • Seed • San Francisco, CA
Thread raises $8M led by Integr8d Capital
Future of Work • Seed • New York, NY
Create raises $8.5M led by Bessemer Venture Partners
Infrastructure / Dev Tools • Seed & Series A • San Francisco, CA
Evertune raises $15M led by Felicis Ventures
Sales / Marketing • Series A • New York, NY
Certivity raises $15.5M led by Almaz Capital and UVC Partners
Risk / Security • Series A • Munich, Germany
Casap raises $25M led by Emergence Capital
Risk / Security • Series A • San Francisco, CA
GoodShip raises $25M led by Greenfield Partners
Future of Work • Series B • Bellevue, WA
Protege raises $25M led by Footwork
Data / AI / Machine Learning • Series A • New York, NY
Kustomer raises $30M led by Norwest
Sales / Marketing • Series B • New York, NY
Profound raises $35M led by Sequoia Capital
Sales / Marketing • Series B • New York, NY
Squint raises $40M led by The Westly Group and TCV
Future of Work • Series B • San Jose, CA
XOPS raises $40M led by Activant Capital and FPV Ventures
Future Of Work • Seed • Pleasanton, CA
1Kosmos raises $57M led by Forgepoint Capital and Oquirrh Ventures
Risk / Security • Series B • Iselin, NJ
Titan raises $74M led by General Catalyst
Future of Work • Venture • New York, NY
Celestial AI raises $255M led by VentureTech Alliance and Samsung Catalyst Fund
Data / AI / Machine Learning • Series C • Santa Clara, CA
Laurel raises an Undisclosed Amount led by Workday Ventures
Collaboration / Productivity • Series C • San Francisco, CA
SentinelOne acquires Prompt Security for an Undisclosed Amount
Risk / Security • Acquisition • New York, NY
Anthropic acquires Humanloop for an Undisclosed Amount
Infrastructure / Dev Tools • Acquisition • San Francisco, CA




