#309: A Deeper Look at Circle Eclipse with Circle CEO Sid Yadav
Episode description
Sid Yadav is the CEO and co-founder of Circle, a community platform trusted by creators like Jay and thousands of others to build membership businesses. Today, Circle has ~280 employees and has raised around $30 million.
Before Circle, he was the third hire at Teachable, where he helped build the infrastructure for the creator economy before the term even existed. He spent four years as a tech blogger, writing about startups five to ten times a day, and was one of the first people to ever cover YouTube—back when it was a dating platform!
- The one thing Sid says separates successful communities from the rest
- Circle Eclipse: what it is (AI partner + connective tissue + Discover marketplace) and why 80 of 100 engineers have been on it for 4 months
- The “course as wrong abstraction” insight: why Sid saw self-paced courses heading toward terminal decline as early as 2018
By the end of this episode, you will understand why the most successful community businesses aren’t built around content — they’re built around a specific transformation.
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Full transcript and show notes
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TIMESTAMPS
(00:00) Introduction
(01:44) Teachable origin story: the “I don’t want to play Tinder with you” email that started it all
(06:18) Tech blogger at Mashable — and the story of being first to write about YouTube
(09:15) ~280 employees, $30M raised — the scale of Circle today
(12:52) Why self-paced courses are in terminal decline (the leading indicators Sid saw in 2018)
(17:16) The “course as the wrong abstraction” moment — community as the right container
(22:00) Circle Eclipse: the three major updates launching
(24:00) The connective tissue opportunity: one plus one must equal ten
(33:19) Admin dashboard evolution — where Circle AI lives for returning users
(35:30) The morning brief: five recommended next steps, then you’re good for the day
(38:50) The biggest bet in Circle’s history: 80 engineers, 4 months, Spain offsite
(40:00) Member-side AI agents and where they’re heading
(43:24) Discover: from supply-side listing directory to the first real marketplace for transformations
(48:00) The promise: Discover will never market inside your community — ever
(51:55) Sid’s #1 recommendation: define your transformation
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RECOMMENDED NEXT EPISODE
#295: Community Building Trends for 2026 with Becky Pierson Davidson
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