Happy Valley

ShogunAI vs sideOS

ShogunAI and sideOS are both AI assistants tools. ShogunAI is aimed at freelancers and small businesses, while sideOS is aimed at freelancers and developers.

ShogunAI

Mac assistant that remembers your work and drafts in your voice

sideOS

Voice-driven Mac agent in the notch with local dictation and meetings

PricingPaid · $62Paid
Starting price$62/moNot published
Free planNoNo
Free trial7 days—
Built forFreelancers, Small businessesFreelancers, Developers, Small businesses
Platformsmacosmacos
CountryJP—
Rating——

Choose ShogunAI if

Consultants, founders and managers on Apple silicon Macs who want one searchable memory of their work and drafting in their own voice.

  • Strong privacy controls: exclusions, pause and time-range deletion
  • Uses your own AI provider or installed CLIs
  • Nothing is sent without your approval

Look elsewhere if: Windows users or anyone who only needs meeting notes or a fast launcher (Granola, Raycast).

Choose sideOS if

Mac professionals who want a private voice agent, dictation and meeting notes in one app they pay for once.

  • One-time licence with all future updates and no subscription
  • No account and no sideOS server between you and the model
  • Dictation and meeting transcription stay on the Mac

Look elsewhere if: Windows or mobile users and teams that need shared meeting notes or admin controls (Granola, Raycast).

ShogunAI vs sideOS pricing

ShogunAI

  • Standard$62/moPassive capture, recall, cross-app search; $49/mo yearly
  • Pro$124/moMemory in other AI tools, action approval; $99/mo yearly

sideOS

  • Lifetime licence$89.90One-time; one Mac at a time, every future update included
  • AI model usageVariesPaid to your own provider, about 2 to 5 cents per command

ShogunAI · Key features

  • Passive capture of your work with sources kept
  • Ask questions across mail, meetings and notes
  • Hold right Option to draft text in your own voice in any app
  • Live meeting notes with recap and next steps, no audio stored
  • Two-way live translation and voice dictation
  • Daily brief with schedule, priorities and meeting prep

Cons

  • Mac only, Apple silicon and macOS 14 or newer
  • High price for a personal tool
  • AI provider costs are paid separately

sideOS · Key features

  • Hold-to-talk agent that reads the screen, clicks, types and runs AppleScript
  • On-device dictation into any app in 62 languages at no extra cost
  • Meeting recording for Zoom, Meet and Teams with on-device Whisper and speakers
  • Background tasks with web search, file access and approved shell commands
  • Reminders that can complete a task before they fire
  • One-click MCP connections for Gmail, Calendar, Notion, Slack and GitHub

Cons

  • Apple Silicon Macs with macOS 14 or later only
  • Agent use adds API costs unless you run a local model
  • No free trial or refund window stated on the site

ShogunAI vs sideOS: FAQ

Do ShogunAI and sideOS have a free plan?

ShogunAI has no free plan, a 7-day free trial. sideOS has no free plan.

Not sure yet?