How I use iMessage and AI to run my life

4w ago

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. Numbered Section Summaries 1. The Morning Brief and Proactive Email Triage Each morning, Lindy sends a summary over iMessage: weather, meetings on the calendar, a count of overnight emails triaged, and pre-drafted replies. Flo demonstrates a real example where Lindy caught a restaurant closure, proposed a nearby alternative, and confirmed a meeting with Joshua — all before Flo opened Gmail or his calendar. 2. Human-Sounding Tone as a Product Differentiator The lowercase, conversational register, including the occasional profanity when something goes wrong — required significant prompt engineering. Flo notes that model defaults are effectively baked into model weights, making it genuinely hard to get consistent tonal results. This attention to voice is one of Lindy's clearest differentiators from generic AI chat tools. 3. Live Meeting Intelligence and Post-Meeting Actions During a live in-meeting demo, Flo shows Lindy sending a summary to a teammate who was absent, creating a Google Doc of failure modes discussed, and posting it to Slack, all triggered by a quick iMessage during the meeting itself. 4. Research, Scheduling, and Sales — Covering My Three Use Cases I walk through the three things my current human assistant handles: research, scheduling, and inbound sales lead follow-up. Flo maps each directly to Lindy capabilities — pre-meeting research briefs pull from the public web and private meeting history; scheduling finds mutual availability and sends invites; and CRM integrations mean inbound leads can trigger immediate, context-aware outreach. 5. Lindy vs. OpenClaw vs. Claude Flo frames OpenClaw as Linux — extremely powerful, self-modifying, and suited to technical users comfortable with the risk. He fram