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 Company-Building

15:12 Building in a Fast-Moving AI World

16:59 Current Use Cases, Private Beta, and Product Direction

19:52 Long-Term Vision: Context, Tone, and the Future of Work

26:07 What’s Emerging in SF: AI Video and New Frontiers

28:15 A Day in the Life of a YC Founder

32:05 Launch Plans: Waitlist, Beta Access, and Community

34:00 The Billboard Question: Connor’s Final Message

36:08 Closing Thoughts

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