Get five people talking about your product - iterative feedback with Ben Vinegar
Shownotes
If you ship features and never hear what users actually said, this episode is for you. Kent talks with Ben Vinegar - co-founder of Modem, formerly founding engineer and VPE at Sentry - about aggregating feedback, eliminating adoption barriers, and keeping human judgment in the loop as AI speeds up shipping.
They cover FreshBooks-era product engineering, Modem's approach to capturing feedback across Slack, Discord, GitHub, and support tools, and why five real conversations beat a median LLM opinion.
- (00:00) - Meet Ben Vinegar
- (01:29) - Career startup guy
- (03:48) - What Modem is for
- (06:59) - Building products for builders
- (12:58) - Aggregating feedback at scale
- (15:26) - FreshBooks and early product loops
- (21:34) - Onboarding and getting users unstuck
- (25:06) - Emerging technology at Sentry
- (27:59) - Buy a laundromat - go deep on users
- (33:56) - Support culture and intentionality
- (39:35) - Human connection in the feedback loop
- (42:27) - Hunk and accelerating taste with AI
- (45:12) - Human judgment vs median products
- (49:43) - Homework: five people talking
Ben Vinegar calls himself a career startup guy - early at FreshBooks, Disqus, and Sentry (first five people through ~400 employees), then head of product engineering, VPE, and VP of emerging technology. He founded Modem (modem.dev) to give product engineers faster access to what users are saying so they can iterate.
The through-line is closed-loop feedback. Successful products Ben has worked on followed make-a-change, get-it-in-front-of-users, adjust, repeat. Modem aggregates signals from Slack Connect, Discord, GitHub issues, Intercom, Zendesk, and similar channels so teams are not hunting screenshots in five tools.
They talk adoption barriers, FreshBooks' support culture, and why human judgment still differentiates when agents can ship median products. Ben's Hunk terminal diff tool story shows taste accelerating with AI: he built what he needed as a "norm core" Mac user who wanted agents running while he closed the laptop. Extreme product bets rarely come from averaged LLM taste.
Homework from Ben, sharpened by Kent: get five people to try your software - and talk with them about their experience using it.
Homework
- Pick something you shipped (or are about to ship).
- Get five people to try it.
- Talk with those five people about their experience using your software - not just whether they clicked install.
Resources
Guest: Ben Vinegar
Host: Kent C. Dodds
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