970 - Using your Voice To Complete Complex Workflows On Your Computer w/ Connor Waslo (Caddy)

About this episode

Mat Sherman interviews Connor Waslo about Caddy, a voice interface for productivity, discussing its origin, challenges, and future in the AI landscape.

Mat Sherman catches up with Connor Waslo, co-founder/CEO of Caddy , a desktop voice interface that keeps you in flow by turning spoken intent into real work across tools like Linear, Slack, Calendar, Gmail, and Notion. Connor shares the origin story with cofounder Rajiv, hard pivots, and craft standards for their private beta. They compare SF’s tech gravity with New York, reflect on learnings from Loom through acquisition, and talk about how YC’s time pressure reshapes execution from September to Demo Day. You’ll hear concrete use cases—function-key capture, automatic screenshots and tickets, calendar creation—plus takes on context, tone, and why video + AI is earlier, better, and scarier than most realize. They close with founder routines, community, and a billboard-ready reminder: who you work with matters most. Time Stamps: 00:00 Introduction and Backstory: How Mat and Connor First Met 01:05 What Caddy Is and How It Works 03:15 The Origin Story: Loom Pain Points, Prototypes, and Pivot Hell 05:41 Lessons From Loom and Transitioning to Founder Life 08:25 Moving to SF for Y Combinator 09:53 SF vs. NYC: Tech Density and Culture 12:49 Inside YC: Speed, Pressure, and…

People in this episode

Host: Mat Sherman

Guest: Connor Waslo

Topics covered

• voice interface
• entrepreneurship
• AI
• product development
• founder experiences

Keywords

• Caddy
• voice interface
• Y Combinator
• Loom
• tech culture
• private beta
• AI workflows
• founder routines
• context and tone
• future of work

Mentioned in this episode

Products: Caddy, Linear, Slack, Calendar, Gmail, Notion

Books & works: A Day in the Life of a YC Founder

Places: SF, New York, NYC, YC

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