An iMessage Executive Assistant

I sit down with Flo, founder of Lindy, to get a live demo of their new product, Lindy Assistant, an AI executive assistant that lives in iMessage and works proactively across email, calendar, Slack, Notion, and 100-plus other tools. Flo walks me through a real day of his own Lindy usage, showing how it drafts email replies, prepares meeting briefs, updates CRMs, and handles calendar changes without being asked. We compare Lindy to OpenClaw and Claude's ecosystem, talk pricing, edge-case power users, and where Lindy goes over the next five years.

Try the ultimate AI assistant: https://startup-ideas-pod.link/lindy

Timestamps

00:00 – Intro

01:09 – What Lindy Assistant is and why Flo built it

02:27 – The daily morning brief

05:16 – Setup: two steps, two minutes, out of the box

05:53 – Get the most out of Lindy Assistant

09:42 – My three assistant use cases: research, scheduling, and sales leads

15:51 – Lindy vs. OpenClaw

17:57 – Lindy vs. Claude ecosystem

19:51 – Where Lindy goes over the next five years

23:42 – Integrations overview (100-plus tools)

24:42 – What Lindy does well and what it does not replace

26:52 – Pricing: starts at $49/month

27:15 – How power users are using Lindy

28:18 – Voice memos, incoming phone calls, and outbound calls

30:00 – How to use Lindy alongside a human executive assistant

Key Points

• Lindy Assistant lives in iMessage, connects to email, calendar, Slack, Notion, and 100-plus other apps, and acts proactively without being prompted.

• Setup takes two minutes: provide a phone number and connect a Google account, and Lindy ingests existing email and tool data immediately.

• Lindy pre-drafts email replies, preps meeting briefs, updates CRMs after calls, flags billing issues, and reschedules dinners at closed restaurants — all without user initiation.

• The voice and tone of the assistant took extensive prompt engineering; the lowercase, casual register is intentional and difficult to achieve with current models.

• Lindy targets the "chief everything officer" — the overwhelmed founder or executive — rather than developers or power users who want a fully programmable agent.

• Pricing starts at $49/month for 90-plus percent of users; heavy users can exceed that and are prompted to upgrade.

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Lindy: https://www.lindy.ai