Enterprise Weekly #526: OpenAI is Finally Open, GPT-5 Lands, and More
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Ten years after launching with the name “OpenAI,” the foundation model giant has finally lived up to its name, releasing not one, but two open weight models.
On Tuesday, OpenAI unveiled gpt-oss-120b and gpt-oss-20b, both delivering state-of-the-art performance at a surprisingly low price point. The 120B model matches or exceeds o4-mini on coding, general problem solving, and tool calling while running efficiently on a single 80GB GPU. The 20B variant performs similarly to o3-mini and runs on just 16GB of memory, putting on-device inference and local deployments squarely within reach.
But open source wasn’t OpenAI’s only drop this week. On Thursday, the long-awaited GPT-5 hit the public. While the benchmarks are impressive, what really stands out is the reception from application-layer builders:
Cursor: “It not only catches tricky, deeply-hidden bugs but can also run long, multi-turn background agents to see complex tasks through to the finish — the kinds of problems that used to leave other models stuck.”
Vercel: “It’s the best frontend AI model, hitting top performance across both the aesthetic sense and the code quality, putting it in a category of its own.”
Notion: “Rapid responses, especially in low reasoning mode, make GPT-5 an ideal model when you need complex tasks solved in one shot.”
The common thread? Tool calling. In GPT-5, tools aren’t just external utilities—they’re woven into the model’s reasoning. It can even call multiple tools in parallel, dramatically reducing latency and enabling long-horizon, multi-step workflows that simply weren’t possible before.
This leap makes GPT-5 more agentic than any prior release, pushing use cases beyond one-shot Q&A toward persistent systems that can run for hours and get more done. It also raises a new frontier for builders: designing the right interfaces, context-engineering strategies, and cost-performance tradeoffs to unlock the model’s full potential.
Our takeaway? The gap between open and closed models is narrowing fast. The most agentic systems yet are about to come online. The opportunity for founders? Combine this new infra with a sharp product and build what wasn’t possible last week. Happy hacking 💪
🎉 Lastly, help us celebrate our portfolio company Authzed’s 5th birthday!
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RSVP here to discover how to build the secure, scalable, AI-ready systems of the future.
📚 Read more news:
WSJ: OpenAI Unveils GPT-5, Its Latest and Most Powerful Model, After Two-Year Wait
VentureBeat: New ‘persona vectors’ from Anthropic let you decode and direct an LLM’s personality
TechCrunch: Perplexity Accused of Scraping Websites That Explicitly Blocked AI Scraping
Bloomberg: How DeepSeek and Open-Source Models Are Shaking Up AI
WIRED: A Single Poisoned Document Could Leak ‘Secret’ Data Via ChatGPT
🧵 Read more threads:
🎙️Jessica Lin: The Truth About Product-Led Growth and How This Company Got It Right, with David Dorman (VP Growth, Grafana Labs)
Jon Lehr: Insights from Conversation with Head of Compliance at Global Bank
Company: GovWell
Role: Software Engineer
Technology: Modern Software for Local Government
Funding: $5.5M from Work-Bench and Bienville Capital
🌟 Company of the Week 🌟
Resolvd AI raises $1.6M led by Spice Capital
Future of Work - Pre-Seed - New York, NY
Founder: Ananth Manivannan
Joinable Labs raises $2M led by Aethir, ASI, Zero Gravity, and Others
Data / AI / Machine Learning • Seed • San Francisco, CA
WiseBee raises $2.5M led by Frontline Ventures and BrightCap Ventures
Risk / Security • Pre-Seed • New York, NY
Cafeteria raises $3M led by Marquee Ventures, Listen Ventures, and Thayer Investment Partners
Sales / Marketing • Venture • Los Angeles, CA
Approov raises $6.7M led by Maven Capital Partners
Risk / Security • Series A • Edinburgh, Scotland
Qbeast raises $7.6M led by Peak XV's Surge
Infrastructure / Dev Tools • Seed • Bellevue, WA
Streamline AI raises $8.6M led by Blumberg Capital
Future of Work • Series A • Burlingame, CA
Kontext raises $10M led by M13
Sales / Marketing • Seed • San Francisco, CA
OLarry raises $10M led by TTV Capital
Future of Work • Series A • San Jose, CA
Vendict raises $10M led by Moneta Ventures and JAL Ventures
Risk / Security • Series A • New York, NY
Kotoba Technologies raises $11.8M led by Globis Capital Partners and Boost Capital
Future of Work • Seed • Seattle, WA
D-Tools raises $12M led by StellarIQ
Collaboration / Productivity • Series C • Concord, CA
Docyt raises $12M led by Pivot Investment Partners
Collaboration / Productivity • Series B • Santa Clara, CA
OpenMind raises $20M led by Pantera Capital
Future of Work • Series A • San Francisco, CA
Tavily raises $20M led by Insight Partners and Alpha Wave Global
Collaboration / Productivity • Series A • New York, NY
Kustomer raises $30M led by Norwest
Sales / Marketing • Series B • Short Hills, NJ
Pantomath raises $30M led by General Catalyst
Data / AI / Machine Learning • Series B • Cincinnati, OH
Fundamental Research Labs raises $33M led by Prosus Ventures
Data / AI / Machine Learning • Series A • San Francisco, CA
Lorikeet raises $35M led by QED Investors
Collaboration / Productivity • Series A • Surry Hills, Australia
Lyric raises $43.5M led by Insight Partners
Future of Work • Series B • Sunnyvale, CA
Rillet raises $70M led by a16z and ICONIQ
Collaboration / Productivity • Series B • New York, NY
Clay raises $100M led by CapitalG
Sales / Marketing • Series C • New York, NY
Decart raises $100M led by Benchmark, Sequoia Capital, and Zeev Ventures
Data / AI / Machine Learning • Series B • San Francisco, CA
Blue J raises $122M led by Oak HC/FT and Sapphire Ventures
Future of Work • Series D • Toronto, Canada
Cloudera acquires Taikun for an Undisclosed Amount
Infrastructure / Dev Tools • Acquisition • Miami, FL
Cloud Software Group acquires Arctera for an Undisclosed Amount
Data / AI / Machine Learning • Acquisition • Pleasanton, CA
Upwork acquires Bubty and Ascen for an Undisclosed Amount
HR Tech • Acquisition • The Hague, The Netherlands / Boston, MA