Uploaded August 2026 | Updated September 2026, 1 week ago
Outset (YC W23) is building an AI customer research platform used by companies like Google, Microsoft, and Nestlé. Its AI interviewers have now conducted millions of conversations, giving companies the scale and speed of a survey with the depth of a one-on-one interview.
In this founder fireside, Outset co-founder and CEO Aaron Cannon sits down with YC's Harj Taggar to talk about building a product before the market was ready for it, how they helped create the category of AI-moderated research, and what comes next.
Aaron shares how they're expanding beyond interviews with Outset's new Simulations Lab and Digital Twins, which let companies simulate their customers and get feedback on everything from messaging and pricing to new products.
Apply to Y Combinator: ycombinator.com/apply
Work at a startup: ycombinator.com/jobs
Chapters:
00:00 — Intro
00:24 — What Outset Does
01:18 — Building a Category Before the Market Was Ready
06:31 — Landing the First Enterprise Customer
08:14 — How Better AI Models Changed the Product
12:57 — When the Market Finally Caught Up
14:45 — From AI Interviews to Customer Simulations
19:40 — Aaron’s Path to Becoming a Founder
Outset (YC W23) is building an AI customer research platform used by companies like Google, Microsoft, and Nestlé. Its AI interviewers have now conducted millions of conversations, giving companies the scale and speed of a survey with the depth of a one-on-one interview.
In this founder fireside, Outset co-founder and CEO Aaron Cannon sits down with YC's Harj Taggar to talk about building a product before the market was ready for it, how they helped create the category of AI-moderated research, and what comes next.
Aaron shares how they're expanding beyond interviews with Outset's new Simulations Lab and Digital Twins, which let companies simulate their customers and get feedback on everything from messaging and pricing to new products.
Apply to Y Combinator: ycombinator.com/apply
Work at a startup: ycombinator.com/jobs
Chapters:
00:00 — Intro
00:24 — What Outset Does
01:18 — Building a Category Before the Market Was Ready
06:31 — Landing the First Enterprise Customer
08:14 — How Better AI Models Changed the Product
12:57 — When the Market Finally Caught Up
14:45 — From AI Interviews to Customer Simulations
19:40 — Aaron’s Path to Becoming a Founder
