How I work from anywhere with a multi-machine setup

Summary

Kun Chen describes a multi-machine workflow for software development and AI agents. He uses a MacBook Pro as his main interactive computer, an always-on Mac mini for remote work, and an iPhone to connect while away.

Machines and workflow

• MacBook Pro (M5, 24 GB): Chen’s primary workstation. He prefers working directly on the laptop rather than using it as a thin client to the Mac mini. Local interaction avoids SSH latency, which can disrupt keyboard-driven work in Neovim, and keeps most tools available when he is away from home.
• Mac mini (M4, 64 GB): A headless, always-on machine for background work. Chen uses a separate administrator account for agent-managed tasks to isolate them from his personal account.
• Laptop agents: A command can keep the laptop running with its lid closed, allowing its agents to continue working when he needs to carry it.

Setting up the headless Mac

The initial setup requires briefly connecting a monitor, keyboard, and mouse. After that, the Mac can be managed remotely.

The tutorial’s initial steps are to:

1. Create a separate administrator account for agent-managed work.
2. Enable Remote Login and allow that account to connect through SSH.
3. Ensure the machines share a local network and note the Mac’s hostname.

For a Mac mini intended to restart and operate unattended, Chen recommends disabling FileVault, enabling automatic login for the dedicated account, preventing sleep, disabling hard-disk sleep, enabling wake for network access, and configuring the Mac to start when power is connected.

He also suggests using an AI coding agent to perform the setup with a “headless” skill or repository, so the agent retains context for future maintenance.

Remote networking and terminal management

• Tailscale creates a private network connecting devices across different locations and networks. Devices can reach one another through Tailscale IP addresses or names, including when a phone or laptop is away from the home network. Chen says the free tier meets his personal needs.
• Herdr is presented as a modern alternative to tmux for managing terminal sessions, tabs, and panes. It can connect to remote machines and display their sessions alongside local ones, allowing multiple machines to be controlled from one terminal interface.

Agent orchestration

FirstMate is Chen’s main agent orchestrator. He runs it on his laptop to coordinate agents across machines.

A remote SecondMate is another FirstMate instance running on a different machine, such as the Mac mini. FirstMate can assign it project work, which it then coordinates locally. This keeps remote agents working even when the laptop—and its FirstMate—is offline. When the laptop returns, Chen can review their progress and continue.

Working from an iPhone

Chen connects to his machines from his phone using the Tailscale app and an SSH client. He demonstrates his app, Ship, connecting to an existing terminal session, making the same terminal-based workflow accessible from his phone.

Ship’s main feature is a draggable dial of terminal actions, designed to reduce reliance on the mobile keyboard and support one-handed use. It can trigger saved commands and voice input. Chen says voice input is transcribed on-device without a subscription. He also demonstrates receiving an agent-generated report with an interactive visual artifact.

Ship is available on iOS, with Android planned.

Guides and demonstrations

• Headless Mac setup: Account isolation, SSH access, unattended startup and power settings, and optional agent-assisted setup.
• Tailscale setup: Adding devices to a private network for remote access.
• Herdr demonstration: Connecting to and managing terminal sessions on multiple machines.
• FirstMate demonstration: Creating a remote SecondMate and delegating project work.
• Phone SSH demonstration: Accessing a computer’s terminal session and using Ship’s dial and voice-input features.

The video is a workflow tutorial rather than a formal product review. Chen discusses trade-offs—especially local responsiveness versus the Mac mini’s always-on availability—and presents Herdr, FirstMate, Tailscale, and Ship as parts of his personal setup.

Main speaker/source: Kun Chen, presenting his own setup and demonstrations.