ChatGPT Ads Are Coming. Here's My Take.

Hi everyone,

I'm writing this from Bodrum on a grey, windy day, the kind of weather that makes you want to stay inside with your laptop and a hot cup of Turkish tea.

Last week I wrote about Claude Cowork and why I think it's a big deal. This week, I want to share my take on the news and some tools I'm excited about.

Let's get into it.

OpenAI announced they're testing ads in the free version of ChatGPT for US users. They're also launching a new $8/month "Go" tier.

Some people are treating this as big news. But honestly? Ads were inevitable.

OpenAI has hundreds of millions of free users, and those servers cost money.

Here's the thing:

If you're reading this newsletter and still only using free AI tools for your work, please just pay for something.

If you can justify $14-15 a month for Netflix, you can pay $20 a month for a tool that makes you smarter and more productive.

Free AI is fine for casual questions, but if you're serious about working with AI, you need to pay for it. The free tiers are limited. The paid tools are where the real value is.

For what it's worth, I just canceled my ChatGPT Pro subscription ($200/month) and downgraded to Plus because I wasn't using the Pro features enough to justify the cost. My team is also considering switching from ChatGPT for Teams to Claude for Teams.

Something interesting happened this month. OpenAI and Anthropic both launched healthcare features within days of each other.

An whopping 230 million people ask ChatGPT health questions every week.

My wife often uses ChatGPT for health stuff, I recently heard her asking about an eyelid cream: "Is this safe? What are the side effects?"

Me? I never ask Claude about health. Claude and I, we work. We cook together, metaphorically speaking, building systems and organizing projects.

The way I think about it: ChatGPT is my buddy. Claude is my colleague.

ChatGPT is great for consumer questions. Personal stuff. Health, travel, general curiosity. Claude is for power users who want to build systems and think through complex problems.

Both are valid. They just serve different purposes.

Anthropic is raising $25 billion at a $350 billion valuation. That's more than double their valuation from four months ago.

What this tells me: AI is moving faster than any of us expected.

When Claude Code came out, I thought "okay, this is interesting." Then Cowork dropped and I thought "wait, already?" I didn't expect to have a tool that does 80% of what I want to do, this fast.

As I write this, I have 5 different Claude Code tabs open, each working on different tasks. I dictate to Claude Code using Aqua Voice. It's become central to how I work.

The fundraise just confirms that Anthropic isn't going anywhere. If you've been hesitant to invest time in Claude, don't be.

Remember when I talked about MCP (Model Context Protocol)? It's Anthropic's way of connecting AI to external tools.

OpenAI and Microsoft have now embraced MCP. Anthropic donated it to the Linux Foundation. This is becoming the standard for how AI connects to everything.

I think of MCP like USB-C. (I just upgraded to iPhone 17 with USB-C, so this analogy is fresh in my mind.) Before USB-C, every device had a different cable. Now there's one standard that works everywhere.

MCP is that for AI. One protocol that lets AI tools connect to any service.

My three main MCPs:

If you're not using Claude Code yet, think about connectors in general. ChatGPT has its own connectors for Google Drive, Gmail, Calendar. The principle is the same: let AI access your actual tools.

Big update: Cowork is now available on the $20/month Claude Pro plan. Not just Max anymore.

I've been using it to dig through 170GB of old data from Rewind AI (that app that recorded everything on your screen). I'm hoping they add team collaboration features soon.

If you haven't tried Cowork yet and you have Claude Pro, go experiment with it.

I mentioned Jace in a previous newsletter. It's replacing Superhuman for me. I'm getting happier with it every week.

It connects to Notion, Google Drive, Slack, and answers emails with full context. The killer feature: it reads PDFs in emails and extracts what I need.

This is a new one. Lightfield is a CRM built for solo founders and founder-led sales.

I've been testing it and the team is incredibly responsive. I gave them feedback and they built the features I asked for in two days. That's the kind of company I love working with.

If you're a solo founder doing your own sales, check it out.

Even if you're not technical, spend some time learning about connectors. Whether that's MCP for Claude, connectors for ChatGPT, or integrations through tools like Zapier.

The future of working with AI is connected AI. The models that have access to your actual data and tools are far more useful than chatbots in isolation.

I'm working on a Claude Code workshop. If you're interested in learning how I use Claude Code for real work, reply to this email and let me know.

I'm also planning a special edition newsletter about the systems I've built. How I organize my work, how I work with AI throughout my day, the actual workflows behind what I do.

Stay tuned.

The common thread this week: AI is maturing from experimental to essential. The companies using free tools will fall behind. The ones investing in connected, capable AI will pull ahead.

Thanks for reading. I read and reply to every email.

Tim

P.S. Please do reply if you're interested in the Claude Code workshop. I want to see if there's enough interest before I put it together.