Typeless vs Wispr Flow
Two cloud dictation apps with almost the same pitch. They differ on price, retention policy and how far the free plan goes. Holdkey is in the third column because it is the different answer to the same question: what if the voice never left your PC? Facts from public pages, September 2026.
| Typeless | Wispr Flow | Holdkey | |
|---|---|---|---|
| Headline | Speak, don't type | Don't type, just speak | Don't type it. Say it. |
| Runs | Cloud, zero data retention | Cloud | On your PC, fully offline |
| Platforms | Mac, Windows, iOS, Android | Mac, Windows, iPhone, Android | Windows |
| Free plan | Free download; limits on the pricing page | 2,000 words a week on desktop | Raw unlimited; Clean 2,000 words a week |
| Paid | See typeless.com/pricing | $15/mo, $12/mo annual | $8/mo, $69/yr, $99 lifetime (first 150) |
| Compliance | ISO 27001, GDPR, HIPAA | SOC 2 Type II, ISO 27001, HIPAA-ready | Nothing leaves the machine, so nothing to certify |
| Sync | Encrypted across devices | Dictionary and snippets synced | None; one PC |
What actually separates them
Both send your audio to a server and delete it afterwards; both work in every app; both sync across devices. Typeless leads with zero retention and certifications, Wispr Flow with polish and a larger user base. If your choice is between the two, try both free plans for a week and pick the one whose cleanup matches how you talk.
If the deciding factor is that your voice should not go to a server at all, or you want it to work on a plane, or you live in a terminal on Windows, neither is built for that. Holdkey is. Typeless vs Holdkey · Wispr Flow vs Holdkey.