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Caveday

Caveday is for anyone who struggles to focus. Do deep work in guided sessions with others.

Visit community on Circle →

Teardown

How this community works

Pricing
$18 a monthAbove the personal development median of $15.
Size
1,320 membersBigger than 80% of the personal development communities indexed here.
Revenue ceiling
$23,760 a monthIf every member paid the listed price. Free tiers, discounts and churn are not visible from outside.
Platform
Circle
Category
Personal Development
Last verified
15 October 2026

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About Caveday

Caveday is for anyone who struggles to focus. Do deep work in guided sessions with others.

Why you should join: Daily facilitated focus sessions with goal sharing, sprints, breaks and planning workshops built on body doubling. Membership is $18 a month.

Tiers and products

Notes

Teardown notes

The one-liner

A paid deep-work membership built on live, guided focus sessions.

What they actually sell

Caveday is run by Jeremy Redleaf. Its own pitch: "Live, guided deep-work sessions with peer accountability and expert facilitation." The public offer sits at $18 a month. The offer is easy to understand in one read, which is half the job of a sales page.

Who pays and why

People who struggle to focus alone. The pull is getting meaningful work done with others. They pay for facilitated focus sessions offered nearly 20 hours a day, planning workshops, Solo Caves and peer check-ins. The emotional pull is being around people chasing the same thing, which matters as much as any single lesson. Caveday gives them one place to bring that problem every week.

Where the members come from

Jeremy Redleaf's name is on the Circle page, so members most likely arrive through Jeremy Redleaf's existing work and audience rather than cold traffic. The community reads as the home base for people already following that work. Jeremy Redleaf stays the visible face of the brand on the page.

What's holding it back

Members who build a solid focus habit may feel they no longer need the room, so Caveday has to keep giving reasons to stay, like cohorts and goal events.

Steal this

Sell guided sessions at set times, so the calendar does the motivating.

Would this work in another niche?

Yes for any habit that benefits from company, like exercise. Weak for solo hobbies.

Written 15 October 2026

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