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Welcome to the Friday edition of our newsletter. We spend Fridays going deeper into tools and trends related to generative AI (and Tuesdays sharing news updates).

There's a saying in photography: the best camera is the one you have with you. Not because it's the fanciest. Because you actually have it.

AI tools work the same way now. They've all gotten genuinely capable. So the AI tool you're already using is likely your best choice. There's no single "right" answer.

But if you are choosing for the first time, or switching, here's what matters. Need a quick reference? Download this guide.

The case for it: Claude is the writing and reasoning specialist. It tends to produce the cleanest prose, handles long documents without losing the thread, and is strong at coding and careful, nuanced analysis. Its flagship model is Claude Opus 4.8, with Sonnet 4.6 as the balanced workhorse and Haiku 4.5 for fast, cheap tasks. If your work is heavy on writing, editing, document analysis, or building things, this is the one that feels most like a sharp collaborator rather than an autocomplete.

Key features: Projects (organized workspaces with persistent context), Artifacts (live documents, code, and apps it builds for you), Skills (instructions that Claude loads as needed), Claude Code for developers, Cowork for multi-step knowledge work, web search, memory across chats, and connectors to tools like Gmail and Google Drive.

Pricing: Free tier (Sonnet 4.6); Pro at $20/month or $17/month billed annually; Max at $100/month and $200/month for heavy users; Team at $25/seat/month annually ($30 monthly); Enterprise is custom.

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The case for it: ChatGPT is the most versatile all-rounder and has the biggest ecosystem. GPT-5.5 launched April 23, 2026, and is the current flagship across paid tiers. It bundles strong text and image generation in a single subscription, plus has a large library of custom GPTs users can access for free. If you want one tool that does a bit of everything and you value the deepest feature set and integrations, this is the safe default.

Key features: Deep Research, the Codex coding agent, Agent Mode, custom GPTs, ChatGPT Images 2.0, memory, and advanced voice.

Pricing: Free ($0, GPT-5.3, with ads in the US); Go at $8/month; Plus at $20/month; Pro at $100/month and $200/month; Business at roughly $20–30/seat (minimum 2 users); Enterprise custom. Note that the US Free and Go tiers now show ads.

The case for it: Gemini wins if you live inside Google Workspace. Its key differentiator is native integration with Gmail, Docs, Sheets, Slides, and Drive. It also has one of the largest context windows and a genuinely generous free tier. Google AI Pro includes Gemini 3.1 Pro with a 1M-token context window, and Gemini 3.5 Flash launched at I/O in May 2026 with Gemini 3.5 Pro rolling out in June. Strong multimodal and video generation round it out.

Key features: Workspace integration, the 1M-token context window, Deep Research, NotebookLM, Veo video generation, image generation (Nano Banana), and Gems (custom assistants).

Pricing: Free tier; Google AI Plus at $7.99/month; Google AI Pro at $19.99/month; Google AI Ultra now starting at $99.99/month (cut from $249.99), with a top tier at $200/month.

The case for it: Copilot's advantage isn't the model — it's where it lives. It's embedded directly in Word, Excel, PowerPoint, Outlook, and Teams, and grounded in your organization's actual data through Microsoft Graph, so it understands your emails, documents, meetings, and files. It's powered by OpenAI's GPT models under the hood (as well as Claude). If your team runs on Microsoft 365 and you want AI working inside your real documents and inbox rather than in a separate chat window, this is the pick.

Key features: AI inside the Office apps (drafting, formula-building, slide generation, inbox triage), org-data grounding via Microsoft Graph, and agentic drafting that pulls from your own files.

Pricing: Copilot Chat is free for users with an eligible Microsoft 365 subscription; Copilot Pro is $20/month for individuals; Microsoft 365 Copilot Business runs about $18–25/seat for organizations up to 300 users; the enterprise add-on is $30/user/month. Remember the Copilot license is an add-on — you pay for it on top of a qualifying Microsoft 365 plan.

The case for it: Grok's edge is real-time information and a looser personality. At $30/month it's pitched on its native real-time X (Twitter) integration, access to live social media trends, and a more conversational, less filtered style. It includes DeepSearch for cited multi-source research and Grok Imagine for image and video generation. If you track breaking news, social trends, or current events, the live X data is the standout. The current models are Grok 4, 4.1, and 4.3, with Grok 4 Heavy on the top tier.

Key features: Real-time X/Twitter search, DeepSearch, Big Brain extended reasoning, Grok Imagine (image/video), voice mode, and a large context window.

Pricing: Free tier; X Premium at $8/month; SuperGrok Lite at $10/month; SuperGrok at $30/month ($300/year); X Premium+ at $40/month; SuperGrok Heavy at $300/month. One privacy note: free and individual consumer plans may use your conversations for model training, while Business and Enterprise plans don't by default.

The case for it: Perplexity is the research and fact-finding specialist. It's an AI search and answer engine (not a general-purpose assistant) and the most purpose-built option if you want transparent source citations and footnoted answers. The Pro plan lets you choose among top models like GPT-5 and Claude Opus, and includes the Comet browser agent. If a big part of your day is "find me accurate, current, sourced information," nothing else here is as focused.

Key features: Cited real-time web answers, model selection, the Comet AI browser (now free), Labs for reports and dashboards, Deep Research, and Perplexity Computer on the Max tier.

Pricing: Free at $0; Pro at $20/month ($200/year); Max at $200/month; Education Pro at $10/month for verified students; Enterprise Pro at $40/seat; Enterprise Max at $325/seat. Worth knowing: data may be used for training on the Free and Pro tiers.

Writing, editing, deep reasoning, or coding → Claude. It's the strongest at long-form prose and careful analysis.

One do-everything tool, plus image generation → ChatGPT. Widest feature set and ecosystem in a single subscription.

You live in Gmail, Docs, and Sheets → Gemini. The Workspace integration and 1M-token context are the differentiators.

Your company runs on Microsoft 365 → Copilot. AI inside your real Word/Excel/Outlook files, grounded in your org's data.

Real-time news, social trends, current events → Grok. Live X data is its unique advantage — useful for trend-spotting.

Research with sources you can verify → Perplexity. Cited answers make fact-checking fast.