😸 Claude vs ChatGPT

gm legends, happy Monday.

OpenAI and Anthropic both launched yesterday. GPT-5.5 wants to be the smartest model. Claude Connectors wants to make AI even more useful. Buried under all of that: a font app that is making me feel happy again.

P.S. The Pitch by Deel London is tomorrow — rolling applications still open for Tel Aviv, Singapore, and Dubai.

GPT-5.5 is OpenAI's latest model — they're billing it as the smartest one yet and, notably, the most intuitive to use.

🔥 Our Take: the "most intuitive" framing is the interesting part. every model release is "smarter" — that's table stakes now. saying it's more intuitive is admitting that previous ones required you to know how to use them well to get good results. if that gap actually closed, that matters more than the benchmark numbers.

Makers — last call to apply for The Pitch by Deel NYC! Get in the running for $1M+ in SAFE funding.

The application deadline has been temporarily extended — so if you missed the original cutoff, you've got one more shot.

What's at stake: up to 100 regional winners each receive $50K in SAFE funding, and up to 10 grand finale winners take home $1M+. Plus a dedicated Product Hunt x The Pitch by Deel leaderboard for every event.

Remaining dates: New York – May 5 | Tel Aviv – May 7 | Singapore – May 12 | Dubai – May 14

DigitalOcean Deploy is a one-day event focused on what happens when AI hits production. Latency, throughput, cost per token, reliability — all the things that show up the second something hits production.

There will be a fireside chat with NVIDIA’s Kari Briski on agentic AI. Teams from Character, Workato, VAST Data, Arcee, and the vLLM ecosystem will be there breaking down how they are actually running inference at scale plus a first look at what DigitalOcean is building next.

April 28 in San Francisco. Free to attend.

Claude Connectors integrates Claude with 200+ apps — Spotify, Instacart, Uber, TripAdvisor and more — so you can book, order, and plan without leaving the conversation.

🔥 Our Take: OpenAI is betting on a smarter model. Anthropic is betting on a more connected one. Claude Connectors isn't about answering questions better — it's about Claude doing things on your behalf. that's a fundamentally different product than a chatbot, and it launched the same day as GPT-5.5, which makes the contrast pretty hard to miss.

Pica is a fully native Mac app for managing fonts — organize collections, test color themes and logos, and watch folders for font changes. built by Josh Puckett.

🔥 Our Take: two AI labs launched today and then there's this — a small, precise, beautiful utility that just does one thing well. no AI, no integrations, no platform play. I keep coming back to it. font management sounds boring until you've lost an hour hunting for a typeface you know you have somewhere.