Happy Valley

Akiflow vs sideOS

Akiflow and sideOS are both personal productivity tools. Akiflow is aimed at freelancers and small businesses, while sideOS is aimed at freelancers and developers.

Akiflow

Command-bar task and time-blocking planner

sideOS

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

PricingPaid · $34Paid
Starting price$34/moNot published
Free planNoNo
Free trial7 days—
Built forFreelancers, Small businessesFreelancers, Developers, Small businesses
Platformsmacos, windows, ios, android, webmacos
CountryIT · 2020—
Rating——

Choose Akiflow if

Power users juggling tasks across many tools.

  • Consolidates scattered tasks
  • Keyboard-first speed
  • Strong integrations

Look elsewhere if: Casual to-do users.

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).

Akiflow vs sideOS pricing

Akiflow

  • Pro$34/mo$19/mo billed annually; tasks, calendar, AI assistant Aki
  • Believer (2-year)$14.90/mo$357.60 paid upfront for 2 years of Pro
  • TeamCustomSet up with sales

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

Akiflow · Key features

  • Universal task inbox from many tools
  • Time blocking on calendar
  • Command bar for quick actions
  • Rituals for daily planning
  • Booking links
  • AI assistant

Cons

  • Expensive
  • No free plan
  • Learning curve

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

Akiflow vs sideOS: FAQ

Do Akiflow and sideOS have a free plan?

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

Not sure yet?