Trawling for Problems with Cleo (and OpenClaw)
My foray into OpenClaw
👋 I was late to the OpenClaw just built “my personal executive assistant” game because I delayed getting a MacMini (when I could have!), and I thought the M5 hardware refresh would come sooner. So I bit the bullet and bought a 14” MacBook Pro M5 instead. Last night I set up OpenClaw.
Here are my first impressions and setup. 🐎
🌟 First impression
Super cool setting it up and then watching my agent, “Cleo,” hatch. It was easy (more below), and I have everything working from Telegram, but I have yet to do anything that I truly can’t do in Claude already. I know there’s a lot more I can enable, but I’m being cautious before I hand over the car keys to Cleo, as it were. 🔑 It’s fun to see that I can tailor every aspect of her personality (she’s supposed to be like a foal).
It’s also amazing that I can connect Cleo to so many different products and models (eventually). Cleo has a lot of potential, but she’s very much the foal I described when I set up her personality. The OpenClaw command line (CLI) reminds me a bit of Claude Code.
Cleo’s MacBook has no personal data and is not signed into any of my accounts yet.
🧪 Test 1: Talk to Cleo from my phone
Connect Cleo on my MacBook to Telegram and be able to talk to her from my iPhone. Works perfectly, and it’s amazing to think I’m communicating with her at home while I’m out and about in the world on my phone. 📱 That said, because she’s powered by Claude, I know a lot of the work is actually happening in the cloud and Cleo (sorry, my little girl) is but an intermediary. When I install my own models locally, this will no longer be true, but then again, I won’t have the same capability as Claude’s state-of-the-art (SOTA) models.
🧪 Test 2: Calendar management
I granted Cleo’s Gmail account access to my GCal and our Child Care Calendar. 📅 Cleo uses web tools to successfully manage our calendars. While this is very cool, I can do this today without burning so many tokens via direct calendar access in Claude. Which raises the question: why does she need tool use to access my GCal at all? 🤔 Direct integration is faster, and more efficient than having Cleo wade around on my computer.
🛠️ Setup
💻 Hardware: 14” MacBook Pro M5
🔒 VPN: Tailscale. Works like a charm no matter where I am! It’s almost hard to believe that Tailscale gives such awesome capability away. (Shh, don’t tell them! 🤫)
🖥️ Screen sharing: Mac Screen Sharing. I remote desktop into my MacBook from anywhere as long as I’m on my VPN.
💬 Messaging client: Telegram. I chose not to go the WA it could run afoul of WA’s rules, so I just didn’t want to go there and then be locked out of WA. Telegram works like a charm and was designed as a messaging client that handles bots. It’s fun being able to talk to my MacBook from my iPhone.
🔑 Accounts: I’ve set up dedicated Apple and Gmail accounts just for Cleo, and granted her read access to the calendars I mentioned above.
🤖 AI: I pay for the $200 Claude Max plan, so why not start there? Well, I can tell you why not: simple requests burn through hundreds of thousands of tokens. I’m not near my limit, however this feels inefficient compared to how Claude Code manages token “spend.” I use a Cleo-dedicated API key I generated in the Claude Console. I chose this over direct auth because I was having issues with the browser auth.
🌐 Browser: Cleo is using Chrome and is signed into her Gmail account (but notably not mine or anyone else’s! 🙅).
⚙ Set up instructions: I used Claire Vo’s excellent article on Lenny’s Newsletter for guidance, the in-product command line prompts, and Claude Code to help debug issues.
What’s next? I’m open to ideas, but I will probably try a brain transplant where I run an open source AI model instead of Claude. Share your ideas. I don’t yet feel as though I have a single, vexing problem I can point Cleo-at. But I am going to continue to fiddle and I hope that changes. Excited to learn more.


