Episode 1 Trailer - Inner Circle

What this episode covers

This week, we're launching Inner Circle, a podcast built for founders and operators who want the unfiltered version of what it takes to build.First up is Sterling Douglass, co-founder and CEO of Chowly.He didn't leave a job he hated. He left one he actually loved.Comfort wasn't the problem. Boredom was.Sterling started as an actuary, moved into startups, and eventually built Chowly after realizing the best ideas don't come from chasing solutions, but from listening to customers. But it wasn't all smooth sailing.Lawsuits with competitors. Co-founder issues. Near acquisitions. Deals falling apart.Over the last decade, he's lived through the startup montage most people only see on Silicon Valley.

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Frequently Asked Questions

How long is this episode of Inner Circle?

This episode is 1 minute long.

When was this Inner Circle episode published?

This episode was published on May 26, 2026.

What is this episode about?

This week, we're launching Inner Circle, a podcast built for founders and operators who want the unfiltered version of what it takes to build.First up is Sterling Douglass, co-founder and CEO of Chowly.He didn't leave a job he hated. He left one he...

Can I download this Inner Circle episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.