Dayheld vs Letterly

Dayheld is a voice-first journal for iPhone, allowing adults to record or type entries and search them by word or date. Optional AI adds reflections, follow-up questions, weekly insights, Life in Review and cited recall; Ask answers from matching entries and links to those entries, while version 1 does not promise meaning-only search. Apple transcribes supported English locales on the device, and Dayheld says recordings are never uploaded for transcription. Users can import a Day One JSON export or dated text and Markdown files; imported entries are excluded from AI processing. Journal and memory records are encrypted with a Keychain-held key, and optional iCloud sync sends encrypted records instead of readable text or audio. Optional AI sends selected readable journal-derived text through Dayheld’s proxy to OpenAI, excluding audio. The Free plan costs nothing; Premium costs $9.99 a month, billed monthly in the U.S. The app requires iOS 17.0 or later and is iPhone-only.

Letterly turns speech into text for messages, emails, notes, meeting summaries, journal entries, social posts, and other writing. Users can dictate inside apps such as Gmail, Slack, and Notion, or upload audio and video for transcription. Recordings can run up to 90 minutes, and speech is automatically detected across more than 90 languages, including when languages change mid-sentence. Users can select ready-made rewrite styles or create their own. Letterly can record offline, and Zapier and webhooks can send notes to other apps. Its MCP connects notes with Claude, ChatGPT, Cursor, Perplexity, Gemini CLI, Codex, VS Code, Windsurf, and Claude Code. Letterly says user words are not used to train AI; its DPA specifies encryption in transit and at rest, access controls, and regular security testing. Users can delete recordings and transcriptions through the app. It is available on Android, iOS, macOS, web, and Windows. In-app PRO prices include $19.99 a month, $89.99 a year, and $249.99, paid once.